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

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

data_exp_51_auto
_database_code_depnum_ccdc_archive 'CCDC 2265194'
loop_
_audit_author_name
_audit_author_address
'Jian-He Cao'
;Northwest Normal University
China
;
_audit_update_record             
;
2023-05-24 deposited with the CCDC.	2023-10-19 downloaded from the CCDC.
;
_audit_creation_date             2022-01-04
_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         'C22 H15 N3 O2'
_chemical_formula_sum            'C22 H15 N3 O2'
_chemical_formula_weight         353.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.7255(2)
_cell_length_b                   19.0167(4)
_cell_length_c                   8.36520(18)
_cell_angle_alpha                90
_cell_angle_beta                 105.134(2)
_cell_angle_gamma                90
_cell_volume                     1800.58(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8452
_cell_measurement_temperature    295.77(10)
_cell_measurement_theta_max      76.9540
_cell_measurement_theta_min      2.3290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11937
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.300
_diffrn_reflns_theta_min         4.546
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.77(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     60.00 105.00   0.50    0.05    --   47.57  28.00  93.00   90
  2  ω     97.00 133.00   0.50    0.05    --  107.75  28.00  93.00   72
  3  ω     98.00 175.00   0.50    0.05    --  107.75  37.00-180.00  154
  4  ω     38.00  63.00   0.50    0.05    --  107.75 -57.00 150.00   50
  5  ω     37.00  63.00   0.50    0.05    --  107.75 -77.00 120.00   52
  6  ω     78.00 103.00   0.50    0.05    --  107.75 -77.00 120.00   50
  7  ω     35.00  60.00   0.50    0.05    --  107.75 -57.00 -30.00   50
  8  ω    -18.00  30.00   0.50    0.05    --   47.57 -28.00 -67.00   96
  9  ω     35.00  60.00   0.50    0.05    --  107.75 -57.00  30.00   50
 10  ω     35.00  61.00   0.50    0.05    --  107.75 -57.00-120.00   52
 11  ω     53.00  79.00   0.50    0.05    --  107.75 -77.00-180.00   52
 12  ω     35.00  60.00   0.50    0.05    --  107.75 -57.00-150.00   50
 13  ω    -93.00 -26.00   0.50    0.05    --  -47.57 125.00-120.00  134
 14  ω    -74.00 -28.00   0.50    0.05    -- -100.00  77.00 -90.00   92
 15  ω   -109.00 -62.00   0.50    0.05    -- -100.00  77.00  60.00   94
 16  ω    -67.00 -28.00   0.50    0.05    -- -100.00  57.00  30.00   78
 17  ω    -69.00 -36.00   0.50    0.05    -- -100.00  57.00  90.00   66
 18  ω    -68.00 -33.00   0.50    0.05    -- -100.00  57.00   0.00   70
 19  ω    -69.00 -28.00   0.50    0.05    -- -100.00  57.00 -90.00   82
 20  ω    -62.00 -36.00   0.50    0.05    -- -100.00  57.00-120.00   52
 21  ω   -174.00 -99.00   0.50    0.05    -- -100.00 -28.00 -67.00  150
 22  ω   -122.00 -50.00   0.50    0.05    --  -47.57 -28.00 -67.00  144
 23  ω     35.00 109.00   0.50    0.05    --  107.75-125.00-180.00  148
 24  ω    -31.00  26.00   0.50    0.05    --  -47.57  28.00  93.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0859237000
_diffrn_orient_matrix_UB_12      0.0291464000
_diffrn_orient_matrix_UB_13      0.0950422000
_diffrn_orient_matrix_UB_21      -0.0969373000
_diffrn_orient_matrix_UB_22      0.0065094000
_diffrn_orient_matrix_UB_23      -0.1638925000
_diffrn_orient_matrix_UB_31      -0.0417105000
_diffrn_orient_matrix_UB_32      -0.0753075000
_diffrn_orient_matrix_UB_33      0.0226308000
_diffrn_radiation_monochromator  mirror
_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_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3236
_reflns_number_total             3640
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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         0.219
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3640
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0488
_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)+(0.0754P)²+0.2758P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1331
_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:
 C2(H2), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_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 0.35210(7) 0.66826(5) 0.68244(11) 0.0427(2) Uani 1 1 d . . . . .
O2 O 0.32849(8) 0.49236(5) 0.80580(12) 0.0487(3) Uani 1 1 d . . . . .
N1 N 0.69072(11) 0.64523(7) 0.9911(2) 0.0634(4) Uani 1 1 d . . . . .
N2 N 0.78778(11) 0.64173(8) 1.0947(2) 0.0661(4) Uani 1 1 d . . . . .
N3 N 0.87379(14) 0.63132(11) 1.1873(3) 0.0968(6) Uani 1 1 d . . . . .
C1 C 0.45047(10) 0.65705(7) 0.80860(15) 0.0392(3) Uani 1 1 d . . . . .
C2 C 0.45689(11) 0.59229(7) 0.87589(16) 0.0420(3) Uani 1 1 d . . . . .
H2 H 0.516809 0.575893 0.964124 0.050 Uiso 1 1 calc R . . . .
C3 C 0.26832(11) 0.58030(7) 0.48107(15) 0.0419(3) Uani 1 1 d . . . . .
C4 C 0.28168(10) 0.60410(6) 0.65809(15) 0.0378(3) Uani 1 1 d . . . . .
C5 C 0.35598(11) 0.55325(6) 0.78850(15) 0.0381(3) Uani 1 1 d . . . . .
C6 C 0.52877(11) 0.71833(7) 0.84642(16) 0.0427(3) Uani 1 1 d . . . . .
C7 C 0.64655(12) 0.71305(7) 0.94045(18) 0.0478(3) Uani 1 1 d . . . . .
C8 C 0.16413(10) 0.61835(7) 0.69737(15) 0.0411(3) Uani 1 1 d . . . . .
C9 C 0.48563(14) 0.78461(7) 0.7891(2) 0.0538(4) Uani 1 1 d . . . . .
H9 H 0.408077 0.788938 0.725323 0.065 Uiso 1 1 calc R . . . .
C10 C 0.33538(13) 0.52616(9) 0.44312(19) 0.0563(4) Uani 1 1 d . . . . .
H10 H 0.389327 0.502721 0.527615 0.068 Uiso 1 1 calc R . . . .
C11 C 0.08214(13) 0.56421(9) 0.6751(2) 0.0553(4) Uani 1 1 d . . . . .
H11 H 0.099273 0.520833 0.635510 0.066 Uiso 1 1 calc R . . . .
C12 C 0.71632(14) 0.77303(9) 0.9747(2) 0.0616(4) Uani 1 1 d . . . . .
H12 H 0.794450 0.769401 1.036738 0.074 Uiso 1 1 calc R . . . .
C13 C 0.13741(14) 0.68208(8) 0.7570(2) 0.0564(4) Uani 1 1 d . . . . .
H13 H 0.191779 0.718716 0.773305 0.068 Uiso 1 1 calc R . . . .
C14 C 0.67096(16) 0.83761(9) 0.9179(3) 0.0697(5) Uani 1 1 d . . . . .
H14 H 0.718348 0.877441 0.942268 0.084 Uiso 1 1 calc R . . . .
C15 C 0.55542(16) 0.84371(8) 0.8248(2) 0.0666(5) Uani 1 1 d . . . . .
H15 H 0.524885 0.887514 0.786519 0.080 Uiso 1 1 calc R . . . .
C16 C 0.18943(16) 0.61421(10) 0.35270(19) 0.0653(4) Uani 1 1 d . . . . .
H16 H 0.143230 0.650663 0.375605 0.078 Uiso 1 1 calc R . . . .
C17 C 0.02916(15) 0.69162(10) 0.7928(2) 0.0690(5) Uani 1 1 d . . . . .
H17 H 0.011484 0.734782 0.832773 0.083 Uiso 1 1 calc R . . . .
C18 C -0.05127(14) 0.63849(11) 0.7700(2) 0.0667(5) Uani 1 1 d . . . . .
H18 H -0.123610 0.645401 0.793803 0.080 Uiso 1 1 calc R . . . .
C19 C -0.02511(14) 0.57470(11) 0.7116(2) 0.0666(5) Uani 1 1 d . . . . .
H19 H -0.079804 0.538267 0.696546 0.080 Uiso 1 1 calc R . . . .
C20 C 0.24459(19) 0.54052(14) 0.1544(2) 0.0818(6) Uani 1 1 d . . . . .
H20 H 0.236276 0.527089 0.045084 0.098 Uiso 1 1 calc R . . . .
C21 C 0.32265(16) 0.50658(12) 0.2796(2) 0.0745(5) Uani 1 1 d . . . . .
H21 H 0.367895 0.469910 0.255417 0.089 Uiso 1 1 calc R . . . .
C22 C 0.1786(2) 0.59444(13) 0.1905(2) 0.0861(6) Uani 1 1 d . . . . .
H22 H 0.125786 0.618087 0.105031 0.103 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 1.3616(14) . ?
O1 C4 1.4575(14) . ?
O2 C5 1.2206(15) . ?
N1 N2 1.2392(18) . ?
N1 C7 1.4131(19) . ?
N2 N3 1.117(2) . ?
C1 C2 1.3479(18) . ?
C1 C6 1.4661(17) . ?
C2 C5 1.4261(17) . ?
C3 C4 1.5169(17) . ?
C3 C10 1.382(2) . ?
C3 C16 1.381(2) . ?
C4 C5 1.5452(16) . ?
C4 C8 1.5225(17) . ?
C6 C7 1.4031(19) . ?
C6 C9 1.3958(19) . ?
C7 C12 1.389(2) . ?
C8 C11 1.3875(19) . ?
C8 C13 1.378(2) . ?
C9 C15 1.376(2) . ?
C10 C21 1.387(2) . ?
C11 C19 1.384(2) . ?
C12 C14 1.373(2) . ?
C13 C17 1.390(2) . ?
C14 C15 1.380(3) . ?
C16 C22 1.382(3) . ?
C17 C18 1.361(3) . ?
C18 C19 1.372(3) . ?
C20 C21 1.360(3) . ?
C20 C22 1.365(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C4 108.15(9) . . ?
N2 N1 C7 117.16(13) . . ?
N3 N2 N1 172.9(2) . . ?
O1 C1 C6 113.51(11) . . ?
C2 C1 O1 114.23(11) . . ?
C2 C1 C6 132.26(12) . . ?
C1 C2 C5 108.25(11) . . ?
C10 C3 C4 121.77(12) . . ?
C16 C3 C4 119.83(13) . . ?
C16 C3 C10 118.37(14) . . ?
O1 C4 C3 107.25(10) . . ?
O1 C4 C5 103.34(9) . . ?
O1 C4 C8 109.42(10) . . ?
C3 C4 C5 113.46(10) . . ?
C3 C4 C8 113.28(10) . . ?
C8 C4 C5 109.53(10) . . ?
O2 C5 C2 129.98(12) . . ?
O2 C5 C4 124.03(11) . . ?
C2 C5 C4 105.99(10) . . ?
C7 C6 C1 122.24(12) . . ?
C9 C6 C1 119.56(12) . . ?
C9 C6 C7 118.20(12) . . ?
C6 C7 N1 117.60(12) . . ?
C12 C7 N1 122.52(13) . . ?
C12 C7 C6 119.83(13) . . ?
C11 C8 C4 118.26(12) . . ?
C13 C8 C4 122.62(12) . . ?
C13 C8 C11 119.11(13) . . ?
C15 C9 C6 121.41(14) . . ?
C3 C10 C21 120.35(16) . . ?
C19 C11 C8 120.06(15) . . ?
C14 C12 C7 120.59(15) . . ?
C8 C13 C17 119.97(15) . . ?
C12 C14 C15 120.34(14) . . ?
C9 C15 C14 119.63(15) . . ?
C3 C16 C22 120.54(18) . . ?
C18 C17 C13 120.75(16) . . ?
C17 C18 C19 119.69(15) . . ?
C18 C19 C11 120.43(16) . . ?
C21 C20 C22 119.52(17) . . ?
C20 C21 C10 120.61(19) . . ?
C20 C22 C16 120.60(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 4.092
_oxdiff_exptl_absorpt_empirical_full_min 0.533
####################################################################### 
# 
# 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_caojianhe-huang-0507_auto
_database_code_depnum_ccdc_archive 'CCDC 2265196'
loop_
_audit_author_name
_audit_author_address
'Jian-He Cao'
;Northwest Normal University
China
;
_audit_update_record             
;
2023-05-24 deposited with the CCDC.	2023-10-19 downloaded from the CCDC.
;
_audit_creation_date             2022-07-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 O2'
_chemical_formula_sum            'C22 H16 O2'
_chemical_formula_weight         312.35
_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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.4368(3)
_cell_length_b                   6.67839(14)
_cell_length_c                   22.2255(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.647(2)
_cell_angle_gamma                90
_cell_volume                     1696.87(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7697
_cell_measurement_temperature    303.93(10)
_cell_measurement_theta_max      74.6870
_cell_measurement_theta_min      1.9840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10857
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.059
_diffrn_reflns_theta_min         3.980
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      303.93(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.946
_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  44.00   0.50    0.05    --   46.32 -37.00-120.00   96
  2  ω     32.00  60.00   0.50    0.05    --  104.25 -77.00-180.00   56
  3  ω     64.00  90.00   0.50    0.05    --  104.25 -77.00-180.00   52
  4  ω    -25.00   1.00   0.50    0.05    --   46.32 -10.00   1.00   52
  5  ω     59.00 119.00   0.50    0.05    --   46.32  10.00 175.00  120
  6  ω     94.00 158.00   0.50    0.05    --  104.25  10.00 175.00  128
  7  ω     32.00  94.00   0.50    0.05    --  104.25 -94.00 -90.00  124
  8  ω     37.00 103.00   0.50    0.05    --  104.25 -94.00-150.00  132
  9  ω     38.00  70.00   0.50    0.05    --  104.25 -94.00  90.00   64
 10  ω    -40.00  26.00   0.50    0.05    --  -46.32  37.00 150.00  132
 11  ω    -22.00   3.00   0.50    0.05    --  -46.32  10.00 175.00   50
 12  ω    -67.00 -29.00   0.50    0.05    -- -102.00  61.00  90.00   76
 13  ω    -69.00 -44.00   0.50    0.05    -- -102.00  61.00   0.00   50
 14  ω    -66.00 -30.00   0.50    0.05    -- -102.00  61.00-120.00   72
 15  ω    -63.00 -37.00   0.50    0.05    -- -102.00 125.00 -60.00   52
 16  ω   -112.00 -68.00   0.50    0.05    -- -102.00 125.00 -60.00   88
 17  ω   -116.00 -34.00   0.50    0.05    --  -46.32 -10.00   1.00  164
 18  ω   -174.00 -85.00   0.50    0.05    -- -102.00 -61.00 -60.00  178
 19  ω   -147.00 -85.00   0.50    0.05    -- -102.00 -10.00   1.00  124
 20  ω   -138.00 -85.00   0.50    0.05    -- -102.00 -61.00 120.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0500821000
_diffrn_orient_matrix_UB_12      0.0004649000
_diffrn_orient_matrix_UB_13      0.0635746000
_diffrn_orient_matrix_UB_21      0.1237111000
_diffrn_orient_matrix_UB_22      -0.0343678000
_diffrn_orient_matrix_UB_23      0.0273344000
_diffrn_orient_matrix_UB_31      0.0187500000
_diffrn_orient_matrix_UB_32      0.2281025000
_diffrn_orient_matrix_UB_33      0.0040069000
_diffrn_radiation_monochromator  mirror
_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_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2776
_reflns_number_total             3353
_reflns_odcompleteness_completeness 99.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.109
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.031
_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     217
_refine_ls_number_reflns         3353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.067
_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)+(0.0637P)²+0.1194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1196
_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:
 C2(H2), C3(H3), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13),
 C15(H15), C16(H16), 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 0.63744(9) 0.18348(16) 0.34015(4) 0.0811(3) Uani 1 1 d . . . . .
O2 O 0.65287(9) 0.23647(18) 0.48136(4) 0.0865(3) Uani 1 1 d . . . . .
C1 C 0.38025(10) 0.33270(18) 0.40264(5) 0.0538(3) Uani 1 1 d . . . . .
C2 C 0.09722(13) 0.0732(3) 0.43749(6) 0.0778(4) Uani 1 1 d . . . . .
H2 H 0.070744 -0.054711 0.446536 0.093 Uiso 1 1 calc R U . . .
C3 C 0.17392(11) 0.4484(2) 0.40793(6) 0.0684(3) Uani 1 1 d . . . . .
H3 H 0.198734 0.575347 0.396748 0.082 Uiso 1 1 calc R U . . .
C4 C 0.40515(9) 0.46408(18) 0.35078(5) 0.0541(3) Uani 1 1 d . . . . .
C5 C 0.47266(15) 0.7722(3) 0.30914(10) 0.0969(6) Uani 1 1 d . . . . .
H5 H 0.505684 0.898390 0.314650 0.116 Uiso 1 1 calc R U . . .
C6 C 0.72740(9) 0.48617(19) 0.37189(5) 0.0561(3) Uani 1 1 d . . . . .
C7 C 0.85507(13) 0.8301(3) 0.35205(7) 0.0795(4) Uani 1 1 d . . . . .
H7 H 0.896384 0.947274 0.344987 0.095 Uiso 1 1 calc R U . . .
C8 C 0.46224(11) 0.2558(2) 0.44057(5) 0.0619(3) Uani 1 1 d . . . . .
H8 H 0.434557 0.181697 0.472593 0.074 Uiso 1 1 calc R U . . .
C9 C 0.01947(12) 0.2294(3) 0.43428(6) 0.0798(4) Uani 1 1 d . . . . .
H9 H -0.059032 0.208010 0.442016 0.096 Uiso 1 1 calc R U . . .
C10 C 0.73738(10) 0.6329(2) 0.41591(5) 0.0630(3) Uani 1 1 d . . . . .
H10 H 0.701460 0.614986 0.452536 0.076 Uiso 1 1 calc R U . . .
C11 C 0.80013(12) 0.8046(2) 0.40568(6) 0.0741(4) Uani 1 1 d . . . . .
H11 H 0.805370 0.903544 0.435083 0.089 Uiso 1 1 calc R U . . .
C12 C 0.25416(10) 0.29317(19) 0.41264(5) 0.0558(3) Uani 1 1 d . . . . .
C13 C 0.21461(12) 0.1040(2) 0.42740(5) 0.0650(3) Uani 1 1 d . . . . .
H13 H 0.266971 -0.002307 0.430539 0.078 Uiso 1 1 calc R U . . .
C14 C 0.65051(10) 0.3119(2) 0.37863(5) 0.0594(3) Uani 1 1 d . . . . .
C15 C 0.84927(13) 0.6834(3) 0.30890(6) 0.0795(4) Uani 1 1 d . . . . .
H15 H 0.888658 0.699711 0.273197 0.095 Uiso 1 1 calc R U . . .
C16 C 0.37309(12) 0.4022(2) 0.29289(6) 0.0710(4) Uani 1 1 d . . . . .
H16 H 0.338219 0.277705 0.286923 0.085 Uiso 1 1 calc R U . . .
C17 C 0.39286(15) 0.5250(3) 0.24422(6) 0.0915(5) Uani 1 1 d . . . . .
H17 H 0.371975 0.482269 0.205564 0.110 Uiso 1 1 calc R U . . .
C18 C 0.78541(11) 0.5125(2) 0.31824(5) 0.0691(4) Uani 1 1 d . . . . .
H18 H 0.780922 0.414145 0.288641 0.083 Uiso 1 1 calc R U . . .
C19 C 0.05766(12) 0.4164(3) 0.41969(7) 0.0787(4) Uani 1 1 d . . . . .
H19 H 0.005078 0.522585 0.417667 0.094 Uiso 1 1 calc R U . . .
C20 C 0.45429(12) 0.6509(2) 0.35849(7) 0.0709(4) Uani 1 1 d . . . . .
H20 H 0.475193 0.695668 0.396933 0.085 Uiso 1 1 calc R U . . .
C21 C 0.44273(16) 0.7082(3) 0.25257(9) 0.1024(6) Uani 1 1 d . . . . .
H21 H 0.456422 0.789858 0.219617 0.123 Uiso 1 1 calc R U . . .
C22 C 0.58911(11) 0.2739(2) 0.43787(5) 0.0620(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
O1 C14 1.2175(15) . ?
O2 C22 1.2198(14) . ?
C1 C4 1.4826(15) . ?
C1 C8 1.3446(16) . ?
C1 C12 1.4890(16) . ?
C2 H2 0.9300 . ?
C2 C9 1.371(2) . ?
C2 C13 1.3830(19) . ?
C3 H3 0.9300 . ?
C3 C12 1.3866(18) . ?
C3 C19 1.3791(19) . ?
C4 C16 1.3905(17) . ?
C4 C20 1.3770(18) . ?
C5 H5 0.9300 . ?
C5 C20 1.385(2) . ?
C5 C21 1.362(3) . ?
C6 C10 1.3869(17) . ?
C6 C14 1.4688(18) . ?
C6 C18 1.3923(16) . ?
C7 H7 0.9300 . ?
C7 C11 1.374(2) . ?
C7 C15 1.371(2) . ?
C8 H8 0.9300 . ?
C8 C22 1.4590(18) . ?
C9 H9 0.9300 . ?
C9 C19 1.365(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.3846(17) . ?
C13 H13 0.9300 . ?
C14 C22 1.5310(17) . ?
C15 H15 0.9300 . ?
C15 C18 1.374(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(2) . ?
C17 H17 0.9300 . ?
C17 C21 1.360(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
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
C4 C1 C12 115.43(9) . . ?
C8 C1 C4 124.56(10) . . ?
C8 C1 C12 119.98(10) . . ?
C9 C2 H2 119.7 . . ?
C9 C2 C13 120.62(14) . . ?
C13 C2 H2 119.7 . . ?
C12 C3 H3 119.7 . . ?
C19 C3 H3 119.7 . . ?
C19 C3 C12 120.62(13) . . ?
C16 C4 C1 119.47(11) . . ?
C20 C4 C1 121.76(11) . . ?
C20 C4 C16 118.70(12) . . ?
C20 C5 H5 119.7 . . ?
C21 C5 H5 119.7 . . ?
C21 C5 C20 120.50(16) . . ?
C10 C6 C14 121.67(11) . . ?
C10 C6 C18 118.91(12) . . ?
C18 C6 C14 119.26(11) . . ?
C11 C7 H7 119.9 . . ?
C15 C7 H7 119.9 . . ?
C15 C7 C11 120.29(14) . . ?
C1 C8 H8 115.9 . . ?
C1 C8 C22 128.24(11) . . ?
C22 C8 H8 115.9 . . ?
C2 C9 H9 120.1 . . ?
C19 C9 C2 119.80(13) . . ?
C19 C9 H9 120.1 . . ?
C6 C10 H10 119.8 . . ?
C11 C10 C6 120.35(12) . . ?
C11 C10 H10 119.8 . . ?
C7 C11 C10 120.02(14) . . ?
C7 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C3 C12 C1 119.86(11) . . ?
C13 C12 C1 121.43(11) . . ?
C13 C12 C3 118.70(11) . . ?
C2 C13 C12 119.96(13) . . ?
C2 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
O1 C14 C6 123.25(11) . . ?
O1 C14 C22 115.93(12) . . ?
C6 C14 C22 120.65(11) . . ?
C7 C15 H15 119.9 . . ?
C7 C15 C18 120.19(13) . . ?
C18 C15 H15 119.9 . . ?
C4 C16 H16 119.9 . . ?
C17 C16 C4 120.23(15) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.8 . . ?
C21 C17 C16 120.30(16) . . ?
C21 C17 H17 119.8 . . ?
C6 C18 H18 119.9 . . ?
C15 C18 C6 120.18(13) . . ?
C15 C18 H18 119.9 . . ?
C3 C19 H19 119.9 . . ?
C9 C19 C3 120.24(14) . . ?
C9 C19 H19 119.9 . . ?
C4 C20 C5 120.16(15) . . ?
C4 C20 H20 119.9 . . ?
C5 C20 H20 119.9 . . ?
C5 C21 H21 120.0 . . ?
C17 C21 C5 120.09(14) . . ?
C17 C21 H21 120.0 . . ?
O2 C22 C8 121.53(12) . . ?
O2 C22 C14 115.91(11) . . ?
C8 C22 C14 122.03(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
O1 C14 C22 O2 110.21(15) . . . . ?
O1 C14 C22 C8 -61.52(17) . . . . ?
C1 C4 C16 C17 178.31(12) . . . . ?
C1 C4 C20 C5 -177.81(13) . . . . ?
C1 C8 C22 O2 163.41(14) . . . . ?
C1 C8 C22 C14 -25.3(2) . . . . ?
C1 C12 C13 C2 178.80(11) . . . . ?
C2 C9 C19 C3 0.3(2) . . . . ?
C3 C12 C13 C2 -0.39(18) . . . . ?
C4 C1 C8 C22 -3.4(2) . . . . ?
C4 C1 C12 C3 -42.93(15) . . . . ?
C4 C1 C12 C13 137.89(12) . . . . ?
C4 C16 C17 C21 -0.7(2) . . . . ?
C6 C10 C11 C7 -1.2(2) . . . . ?
C6 C14 C22 O2 -65.14(17) . . . . ?
C6 C14 C22 C8 123.13(13) . . . . ?
C7 C15 C18 C6 -0.8(2) . . . . ?
C8 C1 C4 C16 119.05(14) . . . . ?
C8 C1 C4 C20 -64.14(17) . . . . ?
C8 C1 C12 C3 135.09(13) . . . . ?
C8 C1 C12 C13 -44.09(17) . . . . ?
C9 C2 C13 C12 -1.4(2) . . . . ?
C10 C6 C14 O1 177.97(12) . . . . ?
C10 C6 C14 C22 -7.03(17) . . . . ?
C10 C6 C18 C15 -1.38(19) . . . . ?
C11 C7 C15 C18 2.0(2) . . . . ?
C12 C1 C4 C16 -63.03(15) . . . . ?
C12 C1 C4 C20 113.78(13) . . . . ?
C12 C1 C8 C22 178.72(12) . . . . ?
C12 C3 C19 C9 -2.1(2) . . . . ?
C13 C2 C9 C19 1.5(2) . . . . ?
C14 C6 C10 C11 -173.03(11) . . . . ?
C14 C6 C18 C15 174.10(12) . . . . ?
C15 C7 C11 C10 -1.0(2) . . . . ?
C16 C4 C20 C5 -1.0(2) . . . . ?
C16 C17 C21 C5 -0.5(3) . . . . ?
C18 C6 C10 C11 2.34(19) . . . . ?
C18 C6 C14 O1 2.62(18) . . . . ?
C18 C6 C14 C22 177.62(11) . . . . ?
C19 C3 C12 C1 -177.08(12) . . . . ?
C19 C3 C12 C13 2.12(19) . . . . ?
C20 C4 C16 C17 1.4(2) . . . . ?
C20 C5 C21 C17 0.9(3) . . . . ?
C21 C5 C20 C4 -0.2(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
;
_oxdiff_exptl_absorpt_empirical_full_max 3.970
_oxdiff_exptl_absorpt_empirical_full_min 0.390
