# Electronic Supplementary Material (ESI) for Green 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_eggpr2104
_database_code_depnum_ccdc_archive 'CCDC 2258232'
loop_
_audit_author_name
_audit_author_address
CCDC
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2023-04-23 deposited with the CCDC.	2023-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C24 H15 N O'
_chemical_formula_sum            'C24 H15 N O'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         333.37

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.2536(11)
_cell_length_b                   7.8538(6)
_cell_length_c                   17.2655(15)
_cell_angle_alpha                90
_cell_angle_beta                 92.428(4)
_cell_angle_gamma                90
_cell_volume                     1660.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6246
_cell_measurement_theta_min      3.081
_cell_measurement_theta_max      26.208
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7889
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29403
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.082
_diffrn_reflns_theta_max         26.453
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3399
_reflns_number_gt                2495
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1101P)²+0.1688P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3399
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1668
_refine_ls_wR_factor_gt          0.1440
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
O O 0.29046(12) 0.17950(17) 0.80756(8) 0.0295(3) Uani 1 1 d . . . . .
H0A H 0.362(2) 0.185(3) 0.8191(15) 0.049(7) Uiso 1 1 d . . . . .
N N 0.47659(15) -0.1689(3) 1.14878(10) 0.0424(5) Uani 1 1 d . . . . .
C1 C 0.30012(15) -0.1053(2) 0.86730(11) 0.0259(4) Uani 1 1 d . . . . .
C2 C 0.30717(16) -0.2215(2) 0.80804(11) 0.0309(4) Uani 1 1 d . . . . .
H2A H 0.2750 -0.1987 0.7581 0.037 Uiso 1 1 calc R U . . .
C3 C 0.36318(18) -0.3747(3) 0.82331(12) 0.0346(5) Uani 1 1 d . . . . .
H3A H 0.3684 -0.4573 0.7834 0.042 Uiso 1 1 calc R U . . .
C4 C 0.41065(17) -0.4061(2) 0.89586(12) 0.0343(5) Uani 1 1 d . . . . .
H4A H 0.4487 -0.5100 0.9052 0.041 Uiso 1 1 calc R U . . .
C5 C 0.40361(16) -0.2882(2) 0.95555(12) 0.0318(5) Uani 1 1 d . . . . .
H5A H 0.4361 -0.3107 1.0054 0.038 Uiso 1 1 calc R U . . .
C6 C 0.34815(15) -0.1368(2) 0.94066(11) 0.0260(4) Uani 1 1 d . . . . .
C7 C 0.32808(14) 0.0137(2) 0.98924(11) 0.0253(4) Uani 1 1 d . . . . .
C8 C 0.36015(15) 0.0473(3) 1.06777(11) 0.0293(4) Uani 1 1 d . . . . .
C9 C 0.33127(16) 0.2004(3) 1.10100(11) 0.0336(5) Uani 1 1 d . . . . .
H9A H 0.3545 0.2240 1.1531 0.040 Uiso 1 1 calc R U . . .
C10 C 0.26823(17) 0.3216(2) 1.05918(12) 0.0328(5) Uani 1 1 d . . . . .
C11 C 0.2336(2) 0.4740(3) 1.09432(13) 0.0414(5) Uani 1 1 d . . . . .
H11A H 0.2571 0.4992 1.1462 0.050 Uiso 1 1 calc R U . . .
C12 C 0.1666(2) 0.5852(3) 1.05418(15) 0.0484(6) Uani 1 1 d . . . . .
H12A H 0.1423 0.6857 1.0788 0.058 Uiso 1 1 calc R U . . .
C13 C 0.1335(2) 0.5518(3) 0.97666(15) 0.0424(6) Uani 1 1 d . . . . .
H13A H 0.0865 0.6299 0.9496 0.051 Uiso 1 1 calc R U . . .
C14 C 0.16750(17) 0.4093(2) 0.93983(13) 0.0333(5) Uani 1 1 d . . . . .
H14A H 0.1458 0.3908 0.8870 0.040 Uiso 1 1 calc R U . . .
C15 C 0.23499(15) 0.2886(2) 0.97953(11) 0.0277(4) Uani 1 1 d . . . . .
C16 C 0.26871(15) 0.1330(2) 0.94688(11) 0.0261(4) Uani 1 1 d . . . . .
C17 C 0.24452(15) 0.0698(2) 0.86392(10) 0.0259(4) Uani 1 1 d . . . . .
C18 C 0.12286(15) 0.0552(2) 0.84466(11) 0.0255(4) Uani 1 1 d . . . . .
C19 C 0.07712(16) 0.1136(2) 0.77443(11) 0.0308(4) Uani 1 1 d . . . . .
H19A H 0.1224 0.1643 0.7375 0.037 Uiso 1 1 calc R U . . .
C20 C -0.03498(17) 0.0978(3) 0.75803(12) 0.0358(5) Uani 1 1 d . . . . .
H20A H -0.0657 0.1397 0.7103 0.043 Uiso 1 1 calc R U . . .
C21 C -0.10155(17) 0.0220(3) 0.81047(13) 0.0350(5) Uani 1 1 d . . . . .
H21A H -0.1776 0.0100 0.7988 0.042 Uiso 1 1 calc R U . . .
C22 C -0.05610(17) -0.0365(2) 0.88051(12) 0.0327(5) Uani 1 1 d . . . . .
H22A H -0.1014 -0.0888 0.9169 0.039 Uiso 1 1 calc R U . . .
C23 C 0.05446(16) -0.0193(2) 0.89771(11) 0.0297(4) Uani 1 1 d . . . . .
H23A H 0.0843 -0.0586 0.9462 0.036 Uiso 1 1 calc R U . . .
C24 C 0.42440(17) -0.0733(3) 1.11295(11) 0.0337(5) 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
O C17 1.433(2) . ?
O H0A 0.89(3) . ?
N C24 1.149(3) . ?
C1 C2 1.376(3) . ?
C1 C6 1.396(3) . ?
C1 C17 1.535(2) . ?
C2 C3 1.405(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.381(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.391(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.388(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.476(3) . ?
C7 C16 1.377(3) . ?
C7 C8 1.420(3) . ?
C8 C9 1.384(3) . ?
C8 C24 1.440(3) . ?
C9 C10 1.406(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.415(3) . ?
C10 C15 1.441(3) . ?
C11 C12 1.367(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.407(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.361(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.416(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.415(3) . ?
C16 C17 1.533(3) . ?
C17 C18 1.518(3) . ?
C18 C19 1.392(3) . ?
C18 C23 1.396(3) . ?
C19 C20 1.396(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.379(3) . ?
C20 H20A 0.9500 . ?
C21 C22 1.388(3) . ?
C21 H21A 0.9500 . ?
C22 C23 1.381(3) . ?
C22 H22A 0.9500 . ?
C23 H23A 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
C17 O H0A 106.9(16) . . ?
C2 C1 C6 121.30(17) . . ?
C2 C1 C17 127.42(17) . . ?
C6 C1 C17 111.27(16) . . ?
C1 C2 C3 118.29(18) . . ?
C1 C2 H2A 120.9 . . ?
C3 C2 H2A 120.9 . . ?
C4 C3 C2 120.47(19) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C5 C4 C3 121.06(18) . . ?
C5 C4 H4A 119.5 . . ?
C3 C4 H4A 119.5 . . ?
C6 C5 C4 118.58(18) . . ?
C6 C5 H5A 120.7 . . ?
C4 C5 H5A 120.7 . . ?
C5 C6 C1 120.28(18) . . ?
C5 C6 C7 132.27(18) . . ?
C1 C6 C7 107.44(16) . . ?
C16 C7 C8 119.92(17) . . ?
C16 C7 C6 109.87(16) . . ?
C8 C7 C6 130.20(17) . . ?
C9 C8 C7 119.47(18) . . ?
C9 C8 C24 119.36(18) . . ?
C7 C8 C24 121.15(18) . . ?
C8 C9 C10 121.31(18) . . ?
C8 C9 H9A 119.3 . . ?
C10 C9 H9A 119.3 . . ?
C9 C10 C11 121.4(2) . . ?
C9 C10 C15 119.68(18) . . ?
C11 C10 C15 118.9(2) . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11A 119.8 . . ?
C10 C11 H11A 119.8 . . ?
C11 C12 C13 120.4(2) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C14 C13 C12 121.0(2) . . ?
C14 C13 H13A 119.5 . . ?
C12 C13 H13A 119.5 . . ?
C13 C14 C15 120.6(2) . . ?
C13 C14 H14A 119.7 . . ?
C15 C14 H14A 119.7 . . ?
C16 C15 C14 124.06(18) . . ?
C16 C15 C10 117.38(17) . . ?
C14 C15 C10 118.51(18) . . ?
C7 C16 C15 122.19(17) . . ?
C7 C16 C17 110.68(16) . . ?
C15 C16 C17 127.11(17) . . ?
O C17 C18 107.89(14) . . ?
O C17 C16 111.99(14) . . ?
C18 C17 C16 112.24(15) . . ?
O C17 C1 112.21(15) . . ?
C18 C17 C1 111.76(15) . . ?
C16 C17 C1 100.74(14) . . ?
C19 C18 C23 118.61(18) . . ?
C19 C18 C17 121.43(17) . . ?
C23 C18 C17 119.96(16) . . ?
C18 C19 C20 120.26(19) . . ?
C18 C19 H19A 119.9 . . ?
C20 C19 H19A 119.9 . . ?
C21 C20 C19 120.62(19) . . ?
C21 C20 H20A 119.7 . . ?
C19 C20 H20A 119.7 . . ?
C20 C21 C22 119.22(19) . . ?
C20 C21 H21A 120.4 . . ?
C22 C21 H21A 120.4 . . ?
C23 C22 C21 120.58(19) . . ?
C23 C22 H22A 119.7 . . ?
C21 C22 H22A 119.7 . . ?
C22 C23 C18 120.71(18) . . ?
C22 C23 H23A 119.6 . . ?
C18 C23 H23A 119.6 . . ?
N C24 C8 179.3(2) . . ?

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
C6 C1 C2 C3 0.7(3) . . . . ?
C17 C1 C2 C3 179.31(18) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C4 C5 C6 C7 -178.39(19) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C17 C1 C6 C5 -179.41(16) . . . . ?
C2 C1 C6 C7 178.46(17) . . . . ?
C17 C1 C6 C7 -0.3(2) . . . . ?
C5 C6 C7 C16 179.40(19) . . . . ?
C1 C6 C7 C16 0.5(2) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C1 C6 C7 C8 -179.41(18) . . . . ?
C16 C7 C8 C9 0.0(3) . . . . ?
C6 C7 C8 C9 179.86(18) . . . . ?
C16 C7 C8 C24 -178.55(17) . . . . ?
C6 C7 C8 C24 1.3(3) . . . . ?
C7 C8 C9 C10 1.7(3) . . . . ?
C24 C8 C9 C10 -179.72(18) . . . . ?
C8 C9 C10 C11 176.51(18) . . . . ?
C8 C9 C10 C15 -1.6(3) . . . . ?
C9 C10 C11 C12 -175.8(2) . . . . ?
C15 C10 C11 C12 2.3(3) . . . . ?
C10 C11 C12 C13 -1.7(3) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C13 C14 C15 1.8(3) . . . . ?
C13 C14 C15 C16 176.22(19) . . . . ?
C13 C14 C15 C10 -1.1(3) . . . . ?
C9 C10 C15 C16 -0.3(3) . . . . ?
C11 C10 C15 C16 -178.39(17) . . . . ?
C9 C10 C15 C14 177.23(18) . . . . ?
C11 C10 C15 C14 -0.9(3) . . . . ?
C8 C7 C16 C15 -1.9(3) . . . . ?
C6 C7 C16 C15 178.24(16) . . . . ?
C8 C7 C16 C17 179.47(15) . . . . ?
C6 C7 C16 C17 -0.4(2) . . . . ?
C14 C15 C16 C7 -175.36(18) . . . . ?
C10 C15 C16 C7 2.0(3) . . . . ?
C14 C15 C16 C17 3.1(3) . . . . ?
C10 C15 C16 C17 -179.58(16) . . . . ?
C7 C16 C17 O -119.22(17) . . . . ?
C15 C16 C17 O 62.2(2) . . . . ?
C7 C16 C17 C18 119.24(17) . . . . ?
C15 C16 C17 C18 -59.4(2) . . . . ?
C7 C16 C17 C1 0.22(19) . . . . ?
C15 C16 C17 C1 -178.37(18) . . . . ?
C2 C1 C17 O -59.3(2) . . . . ?
C6 C1 C17 O 119.37(17) . . . . ?
C2 C1 C17 C18 62.0(2) . . . . ?
C6 C1 C17 C18 -119.28(17) . . . . ?
C2 C1 C17 C16 -178.63(18) . . . . ?
C6 C1 C17 C16 0.09(19) . . . . ?
O C17 C18 C19 11.8(2) . . . . ?
C16 C17 C18 C19 135.70(18) . . . . ?
C1 C17 C18 C19 -111.97(19) . . . . ?
O C17 C18 C23 -168.68(16) . . . . ?
C16 C17 C18 C23 -44.8(2) . . . . ?
C1 C17 C18 C23 67.5(2) . . . . ?
C23 C18 C19 C20 0.2(3) . . . . ?
C17 C18 C19 C20 179.69(17) . . . . ?
C18 C19 C20 C21 -1.0(3) . . . . ?
C19 C20 C21 C22 0.9(3) . . . . ?
C20 C21 C22 C23 0.0(3) . . . . ?
C21 C22 C23 C18 -0.8(3) . . . . ?
C19 C18 C23 C22 0.7(3) . . . . ?
C17 C18 C23 C22 -178.79(17) . . . . ?

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.064

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/c
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_k11009-jjw-g(egd-14)
_database_code_depnum_ccdc_archive 'CCDC 2258237'
loop_
_audit_author_name
_audit_author_address
CCDC
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2023-04-23 deposited with the CCDC.	2023-11-17 downloaded from the CCDC.
;
_audit_creation_date             2021-09-14
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 N O'
_chemical_formula_sum            'C21 H15 N O'
_chemical_formula_weight         297.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H15 N O'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7518(2)
_cell_length_b                   9.3697(2)
_cell_length_c                   10.0504(2)
_cell_angle_alpha                107.912(2)
_cell_angle_beta                 94.173(2)
_cell_angle_gamma                100.409(2)
_cell_volume                     764.01(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    30988
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9780
_cell_measurement_theta_min      2.1400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_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       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            48092
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.150
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  36.00   0.50    6.61    --   10.60 -63.00  84.00  230
  2  ω    -15.00 100.00   0.50    6.61    --   10.60  63.00-138.00  230
  3  ω    -36.00  78.00   0.50    6.61    --  -10.90  63.00-138.00  228
  4  ω   -100.00  14.00   0.50    6.61    --  -10.90 -63.00  84.00  228
  5  ω    -79.00  41.00   0.50    6.61    --   10.60 -57.00  30.00  240
  6  ω    -15.00 100.00   0.50    6.61    --   10.60  77.00-120.00  230
  7  ω    -17.00 100.00   0.50    6.61    --   10.60  82.00  90.00  234
  8  ω    -15.00 100.00   0.50    6.61    --   10.60  77.00 -60.00  230
  9  ω   -100.00  17.00   0.50    6.61    --  -10.90 -82.00  30.00  234
 10  ω    -38.00  78.00   0.50    6.61    --  -10.90  82.00 -35.95  232
 11  ω   -100.00  17.00   0.50    6.61    --  -10.90 -82.00 -60.00  234
 12  ω    -38.00  79.00   0.50    6.61    --  -10.90  82.00 -90.00  234
 13  ω   -100.00  17.00   0.50    6.61    --  -10.90 -82.00-150.00  234
 14  ω   -100.00  15.00   0.50    6.61    --  -10.90 -77.00 -30.00  230
 15  ω    -79.00  38.00   0.50    6.61    --   10.60 -82.00  30.00  234
 16  ω    -79.00  38.00   0.50    6.61    --   10.60 -82.00  90.00  234
 17  ω    -79.00  38.00   0.50    6.61    --   10.60 -82.00 150.00  234
 18  ω    -79.00  38.00   0.50    6.61    --   10.60 -82.00   0.00  234
 19  ω    -79.00  38.00   0.50    6.61    --   10.60 -82.00-120.00  234
 20  ω    -79.00  37.00   0.50    6.61    --   10.60 -80.00 -48.90  232
 21  ω    -79.00  38.00   0.50    6.61    --   10.60 -82.00-150.00  234
 22  ω    -79.00  41.00   0.50    6.61    --   10.60 -57.00-120.00  240
 23  ω    -38.00  78.00   0.50    6.61    --  -10.90  81.00-104.47  232
 24  ω    -38.00  79.00   0.50    6.61    --  -10.90  82.00  60.00  234
 25  ω    -37.00  78.00   0.50    6.61    --  -10.90  78.00 153.01  230
 26  ω    -79.00  37.00   0.50    6.61    --   10.60 -79.00 161.52  232
 27  ω    -15.00 100.00   0.50    6.61    --   10.60  77.00 150.00  230
 28  ω    -79.00  38.00   0.50    6.61    --   10.60 -82.00 120.00  234
 29  ω    -79.00  36.00   0.50    6.61    --   10.60 -77.00-180.00  230
 30  ω    -79.00  36.00   0.50    6.61    --   10.60 -77.00-150.00  230
 31  ω    -79.00  41.00   0.50    6.61    --   10.60 -57.00-150.00  240
 32  ω    -38.00  79.00   0.50    6.61    --  -10.90  82.00   0.00  234
 33  ω    -38.00  79.00   0.50    6.61    --  -10.90  82.00  30.00  234
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0537491000
_diffrn_orient_matrix_UB_12      0.0172277000
_diffrn_orient_matrix_UB_13      0.0491042000
_diffrn_orient_matrix_UB_21      -0.0406574000
_diffrn_orient_matrix_UB_22      -0.0779243000
_diffrn_orient_matrix_UB_23      -0.0252748000
_diffrn_orient_matrix_UB_31      0.0487680000
_diffrn_orient_matrix_UB_32      -0.0162518000
_diffrn_orient_matrix_UB_33      0.0505620000
_diffrn_oxdiff_digest_frames     
;
01c735430b3d3c59db58308228bcb56f170002516e4
;
_diffrn_oxdiff_digest_hkl        
;
01b91becf5f380bd4105d3f0b5aa269d0125e4
;
_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              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2484
_reflns_number_total             2683
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2683
_refine_ls_number_restraints     684
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      0.972
_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)+(0.0473P)²+0.2477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0945
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim N1 \\sim O1: within 3.8A with
sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
;
_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
O1 O 0.46953(10) 0.06572(9) 0.36189(9) 0.0249(2) Uani 1 1 d . U . . .
N1 N 0.76968(13) 0.70689(12) 0.20681(11) 0.0279(3) Uani 1 1 d . U . . .
C1 C 0.60020(14) 0.04223(13) 0.37230(12) 0.0211(3) Uani 1 1 d . U . . .
H1 H 0.609109 -0.059430 0.352164 0.025 Uiso 1 1 calc R . . . .
C2 C 0.74694(13) 0.16017(13) 0.41406(12) 0.0203(3) Uani 1 1 d . U . . .
C3 C 0.88883(14) 0.10542(14) 0.35232(14) 0.0257(3) Uani 1 1 d . U . . .
H3A H 0.871069 0.002703 0.284652 0.031 Uiso 1 1 calc R . . . .
H3B H 0.969235 0.180403 0.334173 0.031 Uiso 1 1 calc R . . . .
C4 C 0.87378(14) 0.11990(14) 0.50152(14) 0.0260(3) Uani 1 1 d . U . . .
H4A H 0.944814 0.203803 0.574057 0.031 Uiso 1 1 calc R . . . .
H4B H 0.846613 0.026038 0.524518 0.031 Uiso 1 1 calc R . . . .
C5 C 0.73329(13) 0.32456(13) 0.44567(12) 0.0185(3) Uani 1 1 d . U . . .
C6 C 0.69562(13) 0.40389(13) 0.58188(12) 0.0189(3) Uani 1 1 d . U . . .
C7 C 0.66917(13) 0.33388(14) 0.68712(13) 0.0224(3) Uani 1 1 d . U . . .
H7 H 0.673616 0.231176 0.667762 0.027 Uiso 1 1 calc R . . . .
C8 C 0.63714(14) 0.41509(15) 0.81698(13) 0.0254(3) Uani 1 1 d . U . . .
H8 H 0.621076 0.367005 0.884652 0.030 Uiso 1 1 calc R . . . .
C9 C 0.62827(14) 0.57043(15) 0.84915(13) 0.0266(3) Uani 1 1 d . U . . .
H9 H 0.606536 0.624450 0.937580 0.032 Uiso 1 1 calc R . . . .
C10 C 0.65166(14) 0.64137(14) 0.75012(13) 0.0236(3) Uani 1 1 d . U . . .
H10 H 0.645329 0.743822 0.771418 0.028 Uiso 1 1 calc R . . . .
C11 C 0.68543(13) 0.56082(13) 0.61550(12) 0.0199(3) Uani 1 1 d . U . . .
C12 C 0.70817(13) 0.63384(13) 0.51301(12) 0.0199(3) Uani 1 1 d . U . . .
H12 H 0.700503 0.735889 0.533687 0.024 Uiso 1 1 calc R . . . .
C13 C 0.74159(13) 0.55514(13) 0.38279(12) 0.0192(3) Uani 1 1 d . U . . .
C14 C 0.75752(13) 0.63523(13) 0.28117(12) 0.0207(3) Uani 1 1 d . U . . .
C15 C 0.75479(12) 0.39795(13) 0.34608(12) 0.0184(3) Uani 1 1 d . U . . .
C16 C 0.79075(13) 0.32106(13) 0.20175(12) 0.0196(3) Uani 1 1 d . U . . .
C17 C 0.68861(14) 0.19028(13) 0.11021(13) 0.0239(3) Uani 1 1 d . U . . .
H17 H 0.595574 0.151444 0.138320 0.029 Uiso 1 1 calc R . . . .
C18 C 0.72443(16) 0.11759(15) -0.02231(14) 0.0299(3) Uani 1 1 d . U . . .
H18 H 0.655425 0.030181 -0.082515 0.036 Uiso 1 1 calc R . . . .
C19 C 0.86218(16) 0.17411(16) -0.06576(14) 0.0310(3) Uani 1 1 d . U . . .
H19 H 0.886589 0.124342 -0.154406 0.037 Uiso 1 1 calc R . . . .
C20 C 0.96347(15) 0.30536(16) 0.02375(14) 0.0291(3) Uani 1 1 d . U . . .
H20 H 1.055732 0.344593 -0.005239 0.035 Uiso 1 1 calc R . . . .
C21 C 0.92796(14) 0.37804(14) 0.15570(13) 0.0232(3) Uani 1 1 d . U . . .
H21 H 0.996550 0.466395 0.214851 0.028 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2062(14) . ?
N1 C14 1.1468(16) . ?
C1 H1 0.9300 . ?
C1 C2 1.4731(16) . ?
C2 C3 1.5287(16) . ?
C2 C4 1.5364(17) . ?
C2 C5 1.5029(16) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.4813(19) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.4366(16) . ?
C5 C15 1.3835(16) . ?
C6 C7 1.4178(17) . ?
C6 C11 1.4248(16) . ?
C7 H7 0.9300 . ?
C7 C8 1.3713(17) . ?
C8 H8 0.9300 . ?
C8 C9 1.4085(18) . ?
C9 H9 0.9300 . ?
C9 C10 1.3645(18) . ?
C10 H10 0.9300 . ?
C10 C11 1.4136(16) . ?
C11 C12 1.4082(17) . ?
C12 H12 0.9300 . ?
C12 C13 1.3719(16) . ?
C13 C14 1.4422(16) . ?
C13 C15 1.4325(16) . ?
C15 C16 1.4925(15) . ?
C16 C17 1.3921(16) . ?
C16 C21 1.3938(16) . ?
C17 H17 0.9300 . ?
C17 C18 1.3842(17) . ?
C18 H18 0.9300 . ?
C18 C19 1.3830(19) . ?
C19 H19 0.9300 . ?
C19 C20 1.3845(19) . ?
C20 H20 0.9300 . ?
C20 C21 1.3784(17) . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 H1 117.1 . . ?
O1 C1 C2 125.83(11) . . ?
C2 C1 H1 117.1 . . ?
C1 C2 C3 114.55(10) . . ?
C1 C2 C4 112.81(10) . . ?
C1 C2 C5 117.31(10) . . ?
C3 C2 C4 57.80(8) . . ?
C5 C2 C3 120.98(10) . . ?
C5 C2 C4 119.85(10) . . ?
C2 C3 H3A 117.6 . . ?
C2 C3 H3B 117.6 . . ?
H3A C3 H3B 114.7 . . ?
C4 C3 C2 61.36(8) . . ?
C4 C3 H3A 117.6 . . ?
C4 C3 H3B 117.6 . . ?
C2 C4 H4A 117.7 . . ?
C2 C4 H4B 117.7 . . ?
C3 C4 C2 60.84(8) . . ?
C3 C4 H4A 117.7 . . ?
C3 C4 H4B 117.7 . . ?
H4A C4 H4B 114.8 . . ?
C6 C5 C2 118.35(10) . . ?
C15 C5 C2 121.13(10) . . ?
C15 C5 C6 120.51(10) . . ?
C7 C6 C5 123.08(11) . . ?
C7 C6 C11 117.51(10) . . ?
C11 C6 C5 119.41(10) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.10(11) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.83(11) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.77(11) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.71(11) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C6 120.09(11) . . ?
C12 C11 C6 119.29(10) . . ?
C12 C11 C10 120.62(11) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.30(10) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C14 117.33(10) . . ?
C12 C13 C15 121.89(11) . . ?
C15 C13 C14 120.74(10) . . ?
N1 C14 C13 175.82(12) . . ?
C5 C15 C13 118.57(10) . . ?
C5 C15 C16 123.14(10) . . ?
C13 C15 C16 118.29(10) . . ?
C17 C16 C15 120.85(10) . . ?
C17 C16 C21 118.40(11) . . ?
C21 C16 C15 120.75(10) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.53(11) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.43(12) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.48(12) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.20(12) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 H21 119.5 . . ?
C20 C21 C16 120.96(11) . . ?
C20 C21 H21 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -151.21(12) . . . . ?
O1 C1 C2 C4 145.11(12) . . . . ?
O1 C1 C2 C5 -0.45(18) . . . . ?
C1 C2 C3 C4 -102.47(11) . . . . ?
C1 C2 C4 C3 105.54(11) . . . . ?
C1 C2 C5 C6 80.46(13) . . . . ?
C1 C2 C5 C15 -98.91(13) . . . . ?
C2 C5 C6 C7 -0.68(16) . . . . ?
C2 C5 C6 C11 178.62(10) . . . . ?
C2 C5 C15 C13 -179.48(10) . . . . ?
C2 C5 C15 C16 0.69(17) . . . . ?
C3 C2 C5 C6 -130.74(12) . . . . ?
C3 C2 C5 C15 49.88(16) . . . . ?
C4 C2 C5 C6 -62.59(14) . . . . ?
C4 C2 C5 C15 118.04(12) . . . . ?
C5 C2 C3 C4 107.94(12) . . . . ?
C5 C2 C4 C3 -109.87(12) . . . . ?
C5 C6 C7 C8 178.44(10) . . . . ?
C5 C6 C11 C10 -178.70(10) . . . . ?
C5 C6 C11 C12 1.77(16) . . . . ?
C5 C15 C16 C17 59.04(16) . . . . ?
C5 C15 C16 C21 -120.59(13) . . . . ?
C6 C5 C15 C13 1.16(16) . . . . ?
C6 C5 C15 C16 -178.67(10) . . . . ?
C6 C7 C8 C9 0.55(18) . . . . ?
C6 C11 C12 C13 -0.76(17) . . . . ?
C7 C6 C11 C10 0.65(16) . . . . ?
C7 C6 C11 C12 -178.88(10) . . . . ?
C7 C8 C9 C10 0.04(18) . . . . ?
C8 C9 C10 C11 -0.27(18) . . . . ?
C9 C10 C11 C6 -0.09(17) . . . . ?
C9 C10 C11 C12 179.43(11) . . . . ?
C10 C11 C12 C13 179.71(10) . . . . ?
C11 C6 C7 C8 -0.88(17) . . . . ?
C11 C12 C13 C14 177.69(10) . . . . ?
C11 C12 C13 C15 -0.08(17) . . . . ?
C12 C13 C15 C5 -0.12(17) . . . . ?
C12 C13 C15 C16 179.72(10) . . . . ?
C13 C15 C16 C17 -120.80(12) . . . . ?
C13 C15 C16 C21 59.58(15) . . . . ?
C14 C13 C15 C5 -177.82(10) . . . . ?
C14 C13 C15 C16 2.02(16) . . . . ?
C15 C5 C6 C7 178.70(10) . . . . ?
C15 C5 C6 C11 -2.00(16) . . . . ?
C15 C16 C17 C18 -178.54(11) . . . . ?
C15 C16 C21 C20 178.46(11) . . . . ?
C16 C17 C18 C19 -0.1(2) . . . . ?
C17 C16 C21 C20 -1.18(18) . . . . ?
C17 C18 C19 C20 -0.8(2) . . . . ?
C18 C19 C20 C21 0.7(2) . . . . ?
C19 C20 C21 C16 0.29(19) . . . . ?
C21 C16 C17 C18 1.09(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 1.714
_oxdiff_exptl_absorpt_empirical_full_min 0.647
####################################################################### 
# 
# 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_k11001-jjw-f
_database_code_depnum_ccdc_archive 'CCDC 2258234'
loop_
_audit_author_name
_audit_author_address
CCDC
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2023-04-23 deposited with the CCDC.	2023-11-17 downloaded from the CCDC.
;
_audit_creation_date             2021-01-20
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H14 Cl N'
_chemical_formula_sum            'C24 H14 Cl N'
_chemical_formula_weight         351.81
_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'
Cl Cl 0.1484 0.1585 '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'

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

_cell_length_a                   11.5468(2)
_cell_length_b                   16.9648(2)
_cell_length_c                   8.6098(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.4760(10)
_cell_angle_gamma                90
_cell_volume                     1686.01(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    35323
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9600
_cell_measurement_theta_min      2.1280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            52299
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.092
_diffrn_reflns_theta_min         1.764
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00 100.00   0.50    8.24    --   10.60  82.00  30.00  234
  2  ω    -17.00 100.00   0.50    8.24    --   10.60  82.00  90.00  234
  3  ω    -15.00 100.00   0.50    8.24    --   10.60  77.00 -30.00  230
  4  ω    -17.00 100.00   0.50    8.24    --   10.60  82.00 120.00  234
  5  ω    -20.00 100.00   0.50    8.24    --   10.60  57.00  60.00  240
  6  ω    -17.00 100.00   0.50    8.24    --   10.60  82.00-180.00  234
  7  ω    -17.00 100.00   0.50    8.24    --   10.60  82.00 -90.00  234
  8  ω    -79.00  35.00   0.50    8.24    --   10.60 -71.00  36.84  228
  9  ω    -79.00  36.00   0.50    8.24    --   10.60 -77.00 -90.00  230
 10  ω   -100.00  20.00   0.50    8.24    --  -10.90 -57.00 150.00  240
 11  ω    -36.00  79.00   0.50    8.24    --  -10.90  77.00 -60.00  230
 12  ω   -100.00  17.00   0.50    8.24    --  -10.90 -82.00 120.00  234
 13  ω   -100.00  79.00   0.50    8.24    --  -10.90 -19.00-150.00  358
 14  ω    -79.00  41.00   0.50    8.24    --   10.60 -57.00 120.00  240
 15  ω    -38.00  76.00   0.50    8.24    --  -10.90  82.00-150.00  228
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0484213000
_diffrn_orient_matrix_UB_12      -0.0219083000
_diffrn_orient_matrix_UB_13      0.0248561000
_diffrn_orient_matrix_UB_21      -0.0359319000
_diffrn_orient_matrix_UB_22      0.0334923000
_diffrn_orient_matrix_UB_23      -0.0118344000
_diffrn_orient_matrix_UB_31      -0.0116581000
_diffrn_orient_matrix_UB_32      -0.0121060000
_diffrn_orient_matrix_UB_33      -0.0777207000
_diffrn_oxdiff_digest_frames     
;
01010fccb48567897a5b4b2ca2d9c7fb43000259346
;
_diffrn_oxdiff_digest_hkl        
;
014dda934a8c33b775dbcaf8d121ce08e245da
;
_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              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3298
_reflns_number_total             3598
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3598
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0318
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0414P)²+0.7849P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0851
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21)
;
_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
Cl1 Cl 0.16120(3) 0.66654(2) 0.78605(3) 0.02003(10) Uani 1 1 d . . . . .
N1 N 0.14981(13) 0.25747(8) 0.73398(18) 0.0404(3) Uani 1 1 d . . . . .
C1 C 0.27103(10) 0.59456(7) 0.73033(14) 0.0164(2) Uani 1 1 d . . . . .
C2 C 0.37567(10) 0.63635(7) 0.66450(14) 0.0165(2) Uani 1 1 d . . . . .
C3 C 0.41300(11) 0.71024(7) 0.71565(15) 0.0209(3) Uani 1 1 d . . . . .
H3 H 0.370471 0.737659 0.788326 0.025 Uiso 1 1 calc R . . . .
C4 C 0.51350(12) 0.74310(8) 0.65849(16) 0.0231(3) Uani 1 1 d . . . . .
H4 H 0.537467 0.792602 0.692818 0.028 Uiso 1 1 calc R . . . .
C5 C 0.57839(11) 0.70300(8) 0.55101(15) 0.0223(3) Uani 1 1 d . . . . .
H5 H 0.645711 0.725256 0.513346 0.027 Uiso 1 1 calc R . . . .
C6 C 0.54197(11) 0.62933(8) 0.50012(15) 0.0220(3) Uani 1 1 d . . . . .
H6 H 0.585129 0.601940 0.428078 0.026 Uiso 1 1 calc R . . . .
C7 C 0.44139(11) 0.59628(7) 0.55619(14) 0.0185(3) Uani 1 1 d . . . . .
H7 H 0.417559 0.546871 0.521154 0.022 Uiso 1 1 calc R . . . .
C8 C 0.30171(10) 0.54485(7) 0.87268(14) 0.0182(3) Uani 1 1 d . . . . .
C9 C 0.35924(11) 0.56763(8) 1.00765(15) 0.0224(3) Uani 1 1 d . . . . .
H9 H 0.384245 0.619333 1.021423 0.027 Uiso 1 1 calc R . . . .
C10 C 0.37894(12) 0.51111(9) 1.12298(16) 0.0269(3) Uani 1 1 d . . . . .
H10 H 0.418091 0.525150 1.214591 0.032 Uiso 1 1 calc R . . . .
C11 C 0.34068(12) 0.43393(9) 1.10248(16) 0.0273(3) Uani 1 1 d . . . . .
H11 H 0.354236 0.397024 1.180732 0.033 Uiso 1 1 calc R . . . .
C12 C 0.28236(12) 0.41136(8) 0.96623(15) 0.0235(3) Uani 1 1 d . . . . .
H12 H 0.256385 0.359850 0.953032 0.028 Uiso 1 1 calc R . . . .
C13 C 0.26361(11) 0.46729(7) 0.85006(14) 0.0189(3) Uani 1 1 d . . . . .
C14 C 0.20857(10) 0.46203(7) 0.69394(14) 0.0169(2) Uani 1 1 d . . . . .
C15 C 0.15911(11) 0.39673(7) 0.61339(15) 0.0190(3) Uani 1 1 d . . . . .
C16 C 0.11681(11) 0.40659(7) 0.46357(15) 0.0200(3) Uani 1 1 d . . . . .
H16 H 0.085085 0.363662 0.410478 0.024 Uiso 1 1 calc R . . . .
C17 C 0.12074(10) 0.48075(7) 0.38908(14) 0.0179(3) Uani 1 1 d . . . . .
C18 C 0.07758(11) 0.49002(8) 0.23465(15) 0.0211(3) Uani 1 1 d . . . . .
H18 H 0.046037 0.446903 0.181988 0.025 Uiso 1 1 calc R . . . .
C19 C 0.08173(11) 0.56136(8) 0.16238(15) 0.0235(3) Uani 1 1 d . . . . .
H19 H 0.053172 0.566598 0.060918 0.028 Uiso 1 1 calc R . . . .
C20 C 0.12918(11) 0.62729(8) 0.24084(15) 0.0220(3) Uani 1 1 d . . . . .
H20 H 0.131806 0.675680 0.190302 0.026 Uiso 1 1 calc R . . . .
C21 C 0.17137(10) 0.62108(7) 0.39016(14) 0.0181(3) Uani 1 1 d . . . . .
H21 H 0.201796 0.665281 0.440377 0.022 Uiso 1 1 calc R . . . .
C22 C 0.16910(10) 0.54766(7) 0.46915(14) 0.0161(2) Uani 1 1 d . . . . .
C23 C 0.21264(10) 0.53497(7) 0.62249(14) 0.0161(2) Uani 1 1 d . . . . .
C24 C 0.15369(12) 0.31953(8) 0.68228(17) 0.0252(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
Cl1 C1 1.8333(12) . ?
N1 C24 1.1444(19) . ?
C1 C2 1.5229(16) . ?
C1 C8 1.5220(17) . ?
C1 C23 1.5186(16) . ?
C2 C3 1.3934(17) . ?
C2 C7 1.3943(17) . ?
C3 H3 0.9300 . ?
C3 C4 1.3888(18) . ?
C4 H4 0.9300 . ?
C4 C5 1.3843(19) . ?
C5 H5 0.9300 . ?
C5 C6 1.3862(19) . ?
C6 H6 0.9300 . ?
C6 C7 1.3875(18) . ?
C7 H7 0.9300 . ?
C8 C9 1.3788(18) . ?
C8 C13 1.3994(18) . ?
C9 H9 0.9300 . ?
C9 C10 1.3949(19) . ?
C10 H10 0.9300 . ?
C10 C11 1.392(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.391(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.3915(18) . ?
C13 C14 1.4747(17) . ?
C14 C15 1.4191(17) . ?
C14 C23 1.3832(16) . ?
C15 C16 1.3777(19) . ?
C15 C24 1.4397(17) . ?
C16 H16 0.9300 . ?
C16 C17 1.4134(17) . ?
C17 C18 1.4166(18) . ?
C17 C22 1.4338(17) . ?
C18 H18 0.9300 . ?
C18 C19 1.3622(19) . ?
C19 H19 0.9300 . ?
C19 C20 1.4102(19) . ?
C20 H20 0.9300 . ?
C20 C21 1.3671(18) . ?
C21 H21 0.9300 . ?
C21 C22 1.4197(17) . ?
C22 C23 1.4170(17) . ?

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 Cl1 110.37(8) . . ?
C8 C1 Cl1 107.85(8) . . ?
C8 C1 C2 112.78(10) . . ?
C23 C1 Cl1 107.71(8) . . ?
C23 C1 C2 115.24(10) . . ?
C23 C1 C8 102.36(10) . . ?
C3 C2 C1 122.90(11) . . ?
C3 C2 C7 118.73(11) . . ?
C7 C2 C1 118.21(11) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.24(12) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.74(12) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.30(12) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.28(12) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.70(11) . . ?
C6 C7 H7 119.7 . . ?
C9 C8 C1 128.35(12) . . ?
C9 C8 C13 121.59(12) . . ?
C13 C8 C1 110.06(11) . . ?
C8 C9 H9 120.9 . . ?
C8 C9 C10 118.25(13) . . ?
C10 C9 H9 120.9 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.74(13) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.73(12) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.6 . . ?
C11 C12 C13 118.78(13) . . ?
C13 C12 H12 120.6 . . ?
C8 C13 C14 108.08(11) . . ?
C12 C13 C8 119.90(12) . . ?
C12 C13 C14 132.02(12) . . ?
C15 C14 C13 130.63(11) . . ?
C23 C14 C13 109.42(11) . . ?
C23 C14 C15 119.92(11) . . ?
C14 C15 C24 122.01(12) . . ?
C16 C15 C14 119.43(11) . . ?
C16 C15 C24 118.55(12) . . ?
C15 C16 H16 119.4 . . ?
C15 C16 C17 121.21(11) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C18 120.68(11) . . ?
C16 C17 C22 120.21(11) . . ?
C18 C17 C22 119.12(11) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.78(12) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.24(12) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 120.93(12) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.51(11) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C17 118.42(11) . . ?
C23 C22 C17 116.88(11) . . ?
C23 C22 C21 124.69(11) . . ?
C14 C23 C1 110.07(10) . . ?
C14 C23 C22 122.34(11) . . ?
C22 C23 C1 127.57(11) . . ?
N1 C24 C15 178.53(16) . . ?

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
Cl1 C1 C2 C3 32.93(14) . . . . ?
Cl1 C1 C2 C7 -151.69(10) . . . . ?
Cl1 C1 C8 C9 -68.30(14) . . . . ?
Cl1 C1 C8 C13 112.39(10) . . . . ?
Cl1 C1 C23 C14 -112.58(10) . . . . ?
Cl1 C1 C23 C22 68.72(14) . . . . ?
C1 C2 C3 C4 175.74(12) . . . . ?
C1 C2 C7 C6 -175.68(11) . . . . ?
C1 C8 C9 C10 -179.31(12) . . . . ?
C1 C8 C13 C12 -179.84(11) . . . . ?
C1 C8 C13 C14 0.77(13) . . . . ?
C2 C1 C8 C9 53.83(16) . . . . ?
C2 C1 C8 C13 -125.48(11) . . . . ?
C2 C1 C23 C14 123.75(11) . . . . ?
C2 C1 C23 C22 -54.96(16) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C3 C2 C7 C6 -0.10(18) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C7 0.1(2) . . . . ?
C5 C6 C7 C2 -0.15(19) . . . . ?
C7 C2 C3 C4 0.38(19) . . . . ?
C8 C1 C2 C3 -87.78(14) . . . . ?
C8 C1 C2 C7 87.60(13) . . . . ?
C8 C1 C23 C14 0.97(12) . . . . ?
C8 C1 C23 C22 -177.74(11) . . . . ?
C8 C9 C10 C11 -0.47(19) . . . . ?
C8 C13 C14 C15 178.09(12) . . . . ?
C8 C13 C14 C23 -0.14(14) . . . . ?
C9 C8 C13 C12 0.78(19) . . . . ?
C9 C8 C13 C14 -178.60(11) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C10 C11 C12 C13 0.4(2) . . . . ?
C11 C12 C13 C8 -0.96(19) . . . . ?
C11 C12 C13 C14 178.25(12) . . . . ?
C12 C13 C14 C15 -1.2(2) . . . . ?
C12 C13 C14 C23 -179.41(13) . . . . ?
C13 C8 C9 C10 -0.06(18) . . . . ?
C13 C14 C15 C16 -177.27(12) . . . . ?
C13 C14 C15 C24 1.4(2) . . . . ?
C13 C14 C23 C1 -0.56(13) . . . . ?
C13 C14 C23 C22 178.23(10) . . . . ?
C14 C15 C16 C17 -0.62(18) . . . . ?
C15 C14 C23 C1 -179.01(10) . . . . ?
C15 C14 C23 C22 -0.22(18) . . . . ?
C15 C16 C17 C18 179.62(12) . . . . ?
C15 C16 C17 C22 -0.13(18) . . . . ?
C16 C17 C18 C19 -179.71(12) . . . . ?
C16 C17 C22 C21 -179.99(11) . . . . ?
C16 C17 C22 C23 0.68(17) . . . . ?
C17 C18 C19 C20 -0.1(2) . . . . ?
C17 C22 C23 C1 178.05(11) . . . . ?
C17 C22 C23 C14 -0.51(17) . . . . ?
C18 C17 C22 C21 0.26(17) . . . . ?
C18 C17 C22 C23 -179.08(11) . . . . ?
C18 C19 C20 C21 -0.2(2) . . . . ?
C19 C20 C21 C22 0.51(19) . . . . ?
C20 C21 C22 C17 -0.53(18) . . . . ?
C20 C21 C22 C23 178.74(12) . . . . ?
C21 C22 C23 C1 -1.23(19) . . . . ?
C21 C22 C23 C14 -179.79(11) . . . . ?
C22 C17 C18 C19 0.04(18) . . . . ?
C23 C1 C2 C3 155.19(11) . . . . ?
C23 C1 C2 C7 -29.43(15) . . . . ?
C23 C1 C8 C9 178.27(12) . . . . ?
C23 C1 C8 C13 -1.05(13) . . . . ?
C23 C14 C15 C16 0.80(18) . . . . ?
C23 C14 C15 C24 179.50(12) . . . . ?
C24 C15 C16 C17 -179.37(12) . . . . ?

_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 1.884
_oxdiff_exptl_absorpt_empirical_full_min 0.618
