# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_37-cr-20250707a_auto
_database_code_depnum_ccdc_archive 'CCDC 2489427'
loop_
_audit_author_name
_audit_author_address
'Dengke Ma'
;Capital Medical University
China
;
_audit_update_record             
;
2025-09-18 deposited with the CCDC.	2026-06-05 downloaded from the CCDC.
;
_audit_creation_date             2025-07-08
_audit_creation_method           
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H23 N O2'
_chemical_formula_sum            'C26 H23 N O2'
_chemical_formula_weight         381.45
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.5186(2)
_cell_length_b                   10.6730(2)
_cell_length_c                   19.8595(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2017.57(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8051
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.3080
_cell_measurement_theta_min      4.6590
_shelx_estimated_absorpt_T_max   0.918
_shelx_estimated_absorpt_T_min   0.886
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.103a (Rigaku Oxford Diffraction, 2025)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.130
_diffrn_reflns_theta_min         4.453
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     27.00  53.00   0.50    0.15    --   53.94 -87.00  18.00   52
  2  ω     60.00  85.00   0.50    0.15    --   53.94  42.00  10.00   50
  3  ω     -4.00  21.00   0.50    0.15    --   53.94 -42.00-142.00   50
  4  ω    -32.00  -7.00   0.50    0.15    --  -54.64  87.00 136.00   50
  5  ω   -108.00 -83.00   0.50    0.15    --  -54.64 -42.00-142.00   50
  6  ω     76.00 102.00   0.50    0.15    --   62.12  42.00  10.00   52
  7  ω     44.00  70.00   0.50    0.15    --   62.12 -87.00  18.00   52
  8  ω      8.00  65.00   0.50    0.15    --   62.12-103.00 124.00  114
  9  ω    -72.00 -47.00   0.50    0.15    --  -63.54 103.00-133.00   50
 10  ω   -117.00 -92.00   0.50    0.15    --  -63.54 -42.00-142.00   50
 11  ω    -61.00 -33.00   0.50    0.15    --  -77.65  87.00 136.00   56
 12  ω    -64.00 -39.00   0.50    0.15    --  -77.65 103.00-133.00   50
 13  ω   -134.00 -79.00   0.50    0.15    --  -77.65 -42.00-142.00  110
 14  ω     40.00  87.00   0.50    0.15    --   93.58-103.00 124.00   94
 15  ω     60.00  89.00   0.50    0.15    --   93.58 -87.00  18.00   58
 16  ω     95.00 125.00   0.50    0.15    --   93.58  42.00  10.00   60
 17  ω    108.00 139.00   0.50    0.15    --   93.58 103.00-133.00   62
 18  ω      0.00  25.00   0.50    0.15    --   53.94 -45.00 -60.00   50
 19  ω    -32.00  -6.00   0.50    0.15    --  -54.64  45.00 150.00   52
 20  ω    -32.00  -7.00   0.50    0.15    --  -63.54  45.00-150.00   50
 21  ω    -32.00  -7.00   0.50    0.15    --  -63.54  45.00 -60.00   50
 22  ω    -32.00  -7.00   0.50    0.15    --  -63.54  45.00 150.00   50
 23  ω   -122.00 -90.00   0.50    0.15    --  -77.65 -61.00 -30.00   64
 24  ω   -129.00 -86.00   0.50    0.15    --  -77.65 -61.00 120.00   86
 25  ω   -123.00 -87.00   0.50    0.15    --  -77.65 -61.00  60.00   72
 26  ω    103.00 145.00   0.50    0.15    --   93.58 111.00 -30.00   84
 27  ω     43.00  68.00   0.50    0.15    --   93.58 -94.00  30.00   50
 28  ω     46.00  91.00   0.50    0.15    --   93.58 -94.00 150.00   90
 29  ω     40.00  65.00   0.50    0.15    --   93.58-111.00  60.00   50
 30  ω    119.00 144.00   0.50    0.15    --   93.58 111.00 -90.00   50
 31  ω     46.00  74.00   0.50    0.15    --   93.58-111.00 150.00   56
 32  ω    112.00 141.00   0.50    0.15    --   93.58  61.00-120.00   58
 33  ω     46.00  71.00   0.50    0.15    --   93.58-111.00-120.00   50
 34  ω     51.00  90.00   0.50    0.15    --   93.58 -94.00-180.00   78
 35  ω     95.00 143.00   0.50    0.15    --   93.58  61.00-180.00   96
 36  ω     97.00 142.00   0.50    0.15    --   93.58  45.00 -30.00   90
 37  ω    111.00 145.00   0.50    0.15    --   93.58 111.00  30.00   68
 38  ω    114.00 140.00   0.50    0.15    --   93.58 111.00-120.00   52
 39  ω     95.00 120.00   0.50    0.15    --   93.58  61.00  60.00   50
 40  ω    107.00 147.00   0.50    0.15    --   93.58 111.00  60.00   80
 41  ω    108.00 151.00   0.50    0.15    --   93.58  45.00 120.00   86
 42  ω     45.00  70.00   0.50    0.15    --   93.58 -94.00  60.00   50
 43  ω     96.00 122.00   0.50    0.15    --   93.58  45.00  90.00   52
 44  ω     47.00  93.00   0.50    0.15    --   93.58 -94.00 -60.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, SynergyCustom DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1549082000
_diffrn_orient_matrix_UB_12      -0.0289742000
_diffrn_orient_matrix_UB_13      -0.0161893000
_diffrn_orient_matrix_UB_21      0.0127498000
_diffrn_orient_matrix_UB_22      -0.1261157000
_diffrn_orient_matrix_UB_23      0.0372337000
_diffrn_orient_matrix_UB_31      -0.0450752000
_diffrn_orient_matrix_UB_32      0.0639106000
_diffrn_orient_matrix_UB_33      0.0661178000
_diffrn_oxdiff_digest_od_ed      
;

;
_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         0.733
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                4031
_reflns_number_total             4147
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.44.103a (Rigaku OD, 2025)'
_computing_data_collection       
'CrysAlisPro system (CCD 44.103a 64-bit (release 31-03-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.44.103a (Rigaku OD, 2025)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1661 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(8)
_refine_ls_extinction_coef       0.0042(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0289
_refine_ls_restrained_S_all      1.069
_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)+(0.0432P)²+0.2950P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0774
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10),
 C11(H11), C12(H12), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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 0.76404(12) 0.74961(10) 0.34979(5) 0.0197(2) Uani 1 1 d . . . . .
O2 O 0.77178(12) 0.92853(11) 0.40854(6) 0.0252(3) Uani 1 1 d . . . . .
N1 N 0.59375(15) 0.66438(14) 0.56095(7) 0.0239(3) Uani 1 1 d . . . . .
H1 H 0.565614 0.682566 0.602014 0.029 Uiso 1 1 calc R U . . .
C1 C 0.80289(17) 0.53612(15) 0.31822(8) 0.0189(3) Uani 1 1 d . . . . .
C2 C 0.84929(18) 0.42369(16) 0.34607(8) 0.0219(3) Uani 1 1 d . . . . .
H2 H 0.815454 0.397953 0.388893 0.026 Uiso 1 1 calc R U . . .
C3 C 0.94503(19) 0.34877(17) 0.31150(9) 0.0248(4) Uani 1 1 d . . . . .
H3 H 0.975610 0.271905 0.330647 0.030 Uiso 1 1 calc R U . . .
C4 C 0.99571(18) 0.38609(17) 0.24928(9) 0.0241(4) Uani 1 1 d . . . . .
H4 H 1.063465 0.336478 0.226415 0.029 Uiso 1 1 calc R U . . .
C5 C 0.94709(17) 0.49617(17) 0.22057(8) 0.0234(4) Uani 1 1 d . . . . .
H5 H 0.980824 0.521402 0.177637 0.028 Uiso 1 1 calc R U . . .
C6 C 0.84950(17) 0.56973(16) 0.25409(8) 0.0211(3) Uani 1 1 d . . . . .
H6 H 0.814167 0.643421 0.233285 0.025 Uiso 1 1 calc R U . . .
C7 C 0.55784(17) 0.62627(15) 0.32218(7) 0.0182(3) Uani 1 1 d . . . . .
C8 C 0.49688(18) 0.51494(16) 0.29956(8) 0.0214(3) Uani 1 1 d . . . . .
H8 H 0.547880 0.438683 0.302890 0.026 Uiso 1 1 calc R U . . .
C9 C 0.36266(18) 0.51443(17) 0.27229(9) 0.0254(4) Uani 1 1 d . . . . .
H9 H 0.322082 0.437927 0.257466 0.031 Uiso 1 1 calc R U . . .
C10 C 0.28764(18) 0.62522(17) 0.26662(9) 0.0263(4) Uani 1 1 d . . . . .
H10 H 0.195948 0.625020 0.247719 0.032 Uiso 1 1 calc R U . . .
C11 C 0.34724(18) 0.73614(17) 0.28867(9) 0.0244(4) Uani 1 1 d . . . . .
H11 H 0.296029 0.812237 0.285040 0.029 Uiso 1 1 calc R U . . .
C12 C 0.48177(17) 0.73687(16) 0.31614(8) 0.0213(3) Uani 1 1 d . . . . .
H12 H 0.521932 0.813595 0.330888 0.026 Uiso 1 1 calc R U . . .
C13 C 0.70282(17) 0.62345(15) 0.35501(8) 0.0180(3) Uani 1 1 d . . . . .
C14 C 0.74416(16) 0.81747(15) 0.40855(8) 0.0201(3) Uani 1 1 d . . . . .
C15 C 0.69371(17) 0.73276(15) 0.45931(8) 0.0201(3) Uani 1 1 d . . . . .
C16 C 0.69591(17) 0.60214(15) 0.43243(8) 0.0184(3) Uani 1 1 d . . . . .
H16 H 0.785318 0.561202 0.447100 0.022 Uiso 1 1 calc R U . . .
C17 C 0.57326(17) 0.52860(16) 0.46178(8) 0.0209(3) Uani 1 1 d . . . . .
H17A H 0.576578 0.440629 0.446054 0.025 Uiso 1 1 calc R U . . .
H17B H 0.483149 0.565933 0.447040 0.025 Uiso 1 1 calc R U . . .
C18 C 0.58485(17) 0.53337(16) 0.53899(8) 0.0216(3) Uani 1 1 d . . . . .
H18 H 0.496341 0.497348 0.557989 0.026 Uiso 1 1 calc R U . . .
C19 C 0.64252(17) 0.75913(16) 0.52206(8) 0.0221(3) Uani 1 1 d . . . . .
C20 C 0.6365(2) 0.88816(17) 0.55221(9) 0.0290(4) Uani 1 1 d . . . . .
H20A H 0.542285 0.903303 0.570426 0.044 Uiso 1 1 calc R U . . .
H20B H 0.657247 0.950509 0.517380 0.044 Uiso 1 1 calc R U . . .
H20C H 0.705862 0.894819 0.588478 0.044 Uiso 1 1 calc R U . . .
C21 C 0.70653(18) 0.45414(16) 0.56437(8) 0.0214(3) Uani 1 1 d . . . . .
C22 C 0.6896(2) 0.32476(18) 0.56869(9) 0.0290(4) Uani 1 1 d . . . . .
H22 H 0.602708 0.288121 0.555869 0.035 Uiso 1 1 calc R U . . .
C23 C 0.7976(2) 0.24867(18) 0.59139(10) 0.0365(4) Uani 1 1 d . . . . .
H23 H 0.784148 0.160643 0.594306 0.044 Uiso 1 1 calc R U . . .
C24 C 0.9254(2) 0.30087(18) 0.60985(10) 0.0323(4) Uani 1 1 d . . . . .
H24 H 0.999334 0.248926 0.625801 0.039 Uiso 1 1 calc R U . . .
C25 C 0.9446(2) 0.42918(17) 0.60490(9) 0.0279(4) Uani 1 1 d . . . . .
H25 H 1.032306 0.465301 0.616897 0.033 Uiso 1 1 calc R U . . .
C26 C 0.83588(18) 0.50508(17) 0.58243(8) 0.0244(4) Uani 1 1 d . . . . .
H26 H 0.849885 0.593022 0.579321 0.029 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.4708(18) . ?
O1 C14 1.3863(19) . ?
O2 C14 1.214(2) . ?
N1 H1 0.8800 . ?
N1 C18 1.467(2) . ?
N1 C19 1.354(2) . ?
C1 C2 1.393(2) . ?
C1 C6 1.396(2) . ?
C1 C13 1.520(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.397(2) . ?
C7 C12 1.390(2) . ?
C7 C13 1.527(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.392(2) . ?
C12 H12 0.9500 . ?
C13 C16 1.556(2) . ?
C14 C15 1.437(2) . ?
C15 C16 1.493(2) . ?
C15 C19 1.367(2) . ?
C16 H16 1.0000 . ?
C16 C17 1.523(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.538(2) . ?
C18 H18 1.0000 . ?
C18 C21 1.520(2) . ?
C19 C20 1.503(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.393(2) . ?
C21 C26 1.393(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.385(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.387(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.385(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.388(3) . ?
C26 H26 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
C14 O1 C13 111.40(11) . . ?
C18 N1 H1 117.9 . . ?
C19 N1 H1 117.9 . . ?
C19 N1 C18 124.18(13) . . ?
C2 C1 C6 118.87(15) . . ?
C2 C1 C13 122.42(14) . . ?
C6 C1 C13 118.71(15) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.40(16) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.16(17) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.65(16) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.42(15) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.37(16) . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C13 119.75(14) . . ?
C12 C7 C8 118.58(15) . . ?
C12 C7 C13 121.64(14) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.76(16) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.18(17) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.53(16) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.40(16) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 120.55(16) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
O1 C13 C1 106.22(12) . . ?
O1 C13 C7 108.06(12) . . ?
O1 C13 C16 102.72(12) . . ?
C1 C13 C7 111.92(13) . . ?
C1 C13 C16 114.33(13) . . ?
C7 C13 C16 112.76(13) . . ?
O1 C14 C15 107.91(13) . . ?
O2 C14 O1 118.71(15) . . ?
O2 C14 C15 133.38(16) . . ?
C14 C15 C16 109.39(13) . . ?
C19 C15 C14 128.98(16) . . ?
C19 C15 C16 121.54(15) . . ?
C13 C16 H16 108.4 . . ?
C15 C16 C13 102.56(12) . . ?
C15 C16 H16 108.4 . . ?
C15 C16 C17 109.50(13) . . ?
C17 C16 C13 119.08(13) . . ?
C17 C16 H16 108.4 . . ?
C16 C17 H17A 110.1 . . ?
C16 C17 H17B 110.1 . . ?
C16 C17 C18 108.03(13) . . ?
H17A C17 H17B 108.4 . . ?
C18 C17 H17A 110.1 . . ?
C18 C17 H17B 110.1 . . ?
N1 C18 C17 109.39(13) . . ?
N1 C18 H18 107.6 . . ?
N1 C18 C21 112.81(14) . . ?
C17 C18 H18 107.6 . . ?
C21 C18 C17 111.52(13) . . ?
C21 C18 H18 107.6 . . ?
N1 C19 C15 119.22(15) . . ?
N1 C19 C20 116.35(14) . . ?
C15 C19 C20 124.43(16) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C18 118.95(16) . . ?
C22 C21 C26 118.24(16) . . ?
C26 C21 C18 122.80(15) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 C21 121.04(18) . . ?
C23 C22 H22 119.5 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.08(18) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 120.2 . . ?
C25 C24 C23 119.58(18) . . ?
C25 C24 H24 120.2 . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.12(18) . . ?
C26 C25 H25 119.9 . . ?
C21 C26 H26 119.5 . . ?
C25 C26 C21 120.93(16) . . ?
C25 C26 H26 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 C13 C16 C15 23.67(15) . . . . ?
O1 C13 C16 C17 144.68(14) . . . . ?
O1 C14 C15 C16 5.92(18) . . . . ?
O1 C14 C15 C19 -170.65(16) . . . . ?
O2 C14 C15 C16 -173.00(18) . . . . ?
O2 C14 C15 C19 10.4(3) . . . . ?
N1 C18 C21 C22 157.57(14) . . . . ?
N1 C18 C21 C26 -23.7(2) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C1 C13 C16 C15 138.27(13) . . . . ?
C1 C13 C16 C17 -100.72(17) . . . . ?
C2 C1 C6 C5 -4.0(2) . . . . ?
C2 C1 C13 O1 131.89(15) . . . . ?
C2 C1 C13 C7 -110.40(17) . . . . ?
C2 C1 C13 C16 19.4(2) . . . . ?
C2 C3 C4 C5 -2.2(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C1 2.3(2) . . . . ?
C6 C1 C2 C3 2.6(2) . . . . ?
C6 C1 C13 O1 -48.35(18) . . . . ?
C6 C1 C13 C7 69.36(18) . . . . ?
C6 C1 C13 C16 -160.88(14) . . . . ?
C7 C8 C9 C10 0.6(2) . . . . ?
C7 C13 C16 C15 -92.39(15) . . . . ?
C7 C13 C16 C17 28.6(2) . . . . ?
C8 C7 C12 C11 0.6(2) . . . . ?
C8 C7 C13 O1 158.32(13) . . . . ?
C8 C7 C13 C1 41.71(19) . . . . ?
C8 C7 C13 C16 -88.85(17) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 C7 -0.4(2) . . . . ?
C12 C7 C8 C9 -0.7(2) . . . . ?
C12 C7 C13 O1 -23.96(19) . . . . ?
C12 C7 C13 C1 -140.56(15) . . . . ?
C12 C7 C13 C16 88.87(18) . . . . ?
C13 O1 C14 O2 -170.03(14) . . . . ?
C13 O1 C14 C15 10.86(17) . . . . ?
C13 C1 C2 C3 -177.67(15) . . . . ?
C13 C1 C6 C5 176.25(15) . . . . ?
C13 C7 C8 C9 177.12(14) . . . . ?
C13 C7 C12 C11 -177.18(14) . . . . ?
C13 C16 C17 C18 -174.33(13) . . . . ?
C14 O1 C13 C1 -142.44(12) . . . . ?
C14 O1 C13 C7 97.31(14) . . . . ?
C14 O1 C13 C16 -22.07(16) . . . . ?
C14 C15 C16 C13 -18.75(17) . . . . ?
C14 C15 C16 C17 -146.13(13) . . . . ?
C14 C15 C19 N1 176.77(16) . . . . ?
C14 C15 C19 C20 -3.5(3) . . . . ?
C15 C16 C17 C18 -56.89(17) . . . . ?
C16 C15 C19 N1 0.6(2) . . . . ?
C16 C15 C19 C20 -179.71(15) . . . . ?
C16 C17 C18 N1 54.21(17) . . . . ?
C16 C17 C18 C21 -71.27(17) . . . . ?
C17 C18 C21 C22 -78.86(18) . . . . ?
C17 C18 C21 C26 99.89(18) . . . . ?
C18 N1 C19 C15 -3.3(2) . . . . ?
C18 N1 C19 C20 176.91(15) . . . . ?
C18 C21 C22 C23 179.87(16) . . . . ?
C18 C21 C26 C25 -179.51(15) . . . . ?
C19 N1 C18 C17 -25.3(2) . . . . ?
C19 N1 C18 C21 99.47(18) . . . . ?
C19 C15 C16 C13 158.13(15) . . . . ?
C19 C15 C16 C17 30.7(2) . . . . ?
C21 C22 C23 C24 -0.4(3) . . . . ?
C22 C21 C26 C25 -0.8(2) . . . . ?
C22 C23 C24 C25 -0.5(3) . . . . ?
C23 C24 C25 C26 0.8(3) . . . . ?
C24 C25 C26 C21 -0.2(3) . . . . ?
C26 C21 C22 C23 1.1(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.214 0.691 0.072 18.4 1.7 ?
2 0.286 0.309 0.572 18.4 1.7 ?
3 0.714 0.809 0.928 18.4 1.8 ?
4 0.786 0.191 0.428 18.4 1.7 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 2.992
_oxdiff_exptl_absorpt_empirical_full_min 0.179
####################################################################### 
# 
# 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_37-cr-20250813g_auto
_database_code_depnum_ccdc_archive 'CCDC 2489426'
_audit_update_record             
;
2025-09-19 deposited with the CCDC.	2026-06-05 downloaded from the CCDC.
;
_audit_creation_date             2025-08-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H22 F3 N O5, 1[C6H14]'
_chemical_formula_sum            'C31 H36 F3 N O5'
_chemical_formula_weight         559.61
_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'
F F 0.0727 0.0534 '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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   17.3043(5)
_cell_length_b                   17.6614(5)
_cell_length_c                   9.1942(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.026(2)
_cell_angle_gamma                90
_cell_volume                     2808.16(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10772
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.1470
_cell_measurement_theta_min      3.5700
_shelx_estimated_absorpt_T_max   0.904
_shelx_estimated_absorpt_T_min   0.796
_exptl_absorpt_coefficient_mu    0.854
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.103a (Rigaku Oxford Diffraction, 2025)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            25997
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.938
_diffrn_reflns_theta_min         3.577
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00 -16.00   0.50    0.07    --  -54.64  61.00 150.00   74
  2  ω    -54.00 -28.00   0.50    0.07    --  -77.65  61.00 120.00   52
  3  ω    -45.00 -12.00   0.50    0.07    --  -63.54  61.00 -30.00   66
  4  ω    -53.00 -28.00   0.50    0.07    --  -77.65  61.00-150.00   50
  5  ω    -54.00 -25.00   0.50    0.07    --  -77.65  61.00-180.00   58
  6  ω    -32.00  -6.00   0.50    0.07    --  -63.54  45.00-150.00   52
  7  ω    -32.00  -6.00   0.50    0.07    --  -63.54  45.00-180.00   52
  8  ω    -32.00  -6.00   0.50    0.07    --  -63.54  45.00 -60.00   52
  9  ω    -32.00  -7.00   0.50    0.07    --  -63.54  45.00 -30.00   50
 10  ω    -32.00  -6.00   0.50    0.07    --  -63.54  45.00   0.00   52
 11  ω    -32.00  -6.00   0.50    0.07    --  -63.54  45.00  30.00   52
 12  ω    -32.00  -6.00   0.50    0.07    --  -63.54  45.00  90.00   52
 13  ω    -54.00 -28.00   0.50    0.07    --  -77.65  61.00 150.00   52
 14  ω     16.00  50.00   0.50    0.07    --   62.12 -77.00   0.00   68
 15  ω     40.00  65.00   0.50    0.07    --   93.58-111.00  30.00   50
 16  ω     47.00  78.00   0.50    0.07    --   93.58-111.00 150.00   62
 17  ω     20.00  45.00   0.50    0.07    --   53.94 -61.00  60.00   50
 18  ω     43.00  70.00   0.50    0.07    --   93.58-111.00   0.00   54
 19  ω     41.00  67.00   0.50    0.07    --   93.58-111.00 -30.00   52
 20  ω     40.00  65.00   0.50    0.07    --   93.58-111.00  60.00   50
 21  ω     -3.00  22.00   0.50    0.07    --   53.94 -45.00 -60.00   50
 22  ω      4.00  29.00   0.50    0.07    --   53.94-103.00 -82.00   50
 23  ω     15.00  45.00   0.50    0.07    --   62.12-103.00 -82.00   60
 24  ω     53.00  84.00   0.50    0.07    --   62.12-103.00 -82.00   62
 25  ω     40.00  68.00   0.50    0.07    --   93.58-111.00-150.00   56
 26  ω     40.00  68.00   0.50    0.07    --   93.58-111.00-180.00   56
 27  ω     43.00  93.00   0.50    0.07    --   93.58 -94.00-120.00  100
 28  ω     64.00  90.00   0.50    0.07    --   93.58-103.00 -82.00   52
 29  ω     67.00  93.00   0.50    0.07    --   93.58 -94.00-180.00   52
 30  ω     43.00  93.00   0.50    0.07    --   93.58 -94.00 -60.00  100
 31  ω     52.00  93.00   0.50    0.07    --   93.58 -94.00-150.00   82
 32  ω     43.00  93.00   0.50    0.07    --   93.58 -94.00 -30.00  100
 33  ω     44.00  91.00   0.50    0.07    --   93.58 -94.00 -90.00   94
 34  ω     44.00  70.00   0.50    0.07    --   93.58 -94.00   0.00   52
 35  ω     47.00  93.00   0.50    0.07    --   93.58 -94.00  30.00   92
 36  ω     43.00  93.00   0.50    0.07    --   93.58 -94.00  60.00  100
 37  ω     66.00  92.00   0.50    0.07    --   93.58 -94.00 120.00   52
 38  ω     60.00  91.00   0.50    0.07    --   97.75 -90.00 148.54   62
 39  ω     49.00  93.00   0.50    0.07    --   97.75 -89.00  86.42   88
 40  ω     54.00  79.00   0.50    0.07    --   97.75 -91.00  60.28   50
 41  ω     64.00  92.00   0.50    0.07    --   97.75 -91.00   6.34   56
 42  ω     48.00  93.00   0.50    0.07    --   97.75 -92.00 -82.46   90
 43  ω     53.00  80.00   0.50    0.07    --   93.58  15.00 120.00   54
 44  ω     95.00 141.00   0.50    0.07    --   93.58  61.00 150.00   92
 45  ω     95.00 120.00   0.50    0.07    --   93.58  61.00  60.00   50
 46  ω    117.00 146.00   0.50    0.07    --   93.58  61.00   0.00   58
 47  ω     95.00 120.00   0.50    0.07    --   93.58  61.00 -30.00   50
 48  ω     98.00 129.00   0.50    0.07    --   93.58  61.00 -90.00   62
 49  ω     95.00 146.00   0.50    0.07    --   93.58  61.00-120.00  102
 50  ω    103.00 139.00   0.50    0.07    --   93.58  61.00-150.00   72
 51  ω     96.00 121.00   0.50    0.07    --   93.58  45.00-120.00   50
 52  ω    103.00 128.00   0.50    0.07    --   93.58  45.00  60.00   50
 53  ω     91.00 151.00   0.50    0.07    --   93.58  30.00 120.00  120
 54  ω     91.00 116.00   0.50    0.07    --   93.58  30.00 150.00   50
 55  ω    121.00 147.00   0.50    0.07    --   93.58  30.00 150.00   52
 56  ω     94.00 119.00   0.50    0.07    --   93.58  15.00 120.00   50
 57  ω     76.00 111.00   0.50    0.07    --   53.94  45.00  90.00   70
 58  ω    113.00 146.00   0.50    0.07    --   93.58 103.00  18.00   66
 59  ω    116.00 142.00   0.50    0.07    --   93.58 111.00 120.00   52
 60  ω    107.00 142.00   0.50    0.07    --   93.58 111.00  60.00   70
 61  ω    109.00 138.00   0.50    0.07    --   93.58 111.00 150.00   58
 62  ω    109.00 134.00   0.50    0.07    --   93.58 111.00 -60.00   50
 63  ω    115.00 140.00   0.50    0.07    --   93.58 111.00-120.00   50
 64  ω    117.00 147.00   0.50    0.07    --   93.58 111.00-150.00   60
 65  ω    110.00 136.00   0.50    0.07    --   93.58 111.00 -90.00   52
 66  ω    122.00 147.00   0.50    0.07    --   93.58 111.00 -30.00   50
 67  ω    115.00 141.00   0.50    0.07    --   93.58 111.00  90.00   52
 68  ω    -92.00 -63.00   0.50    0.07    --  -82.00  91.00  96.02   58
 69  ω    -93.00 -58.00   0.50    0.07    --  -82.00  98.00  29.99   70
 70  ω    -82.00 -57.00   0.50    0.07    --  -77.65 103.00  18.00   50
 71  ω    -55.00 -12.00   0.50    0.07    --  -63.54 103.00  18.00   86
 72  ω    -40.00 -15.00   0.50    0.07    --  -54.64 103.00  18.00   50
 73  ω    -92.00 -66.00   0.50    0.07    --  -82.00  93.00   0.88   52
 74  ω    -92.00 -53.00   0.50    0.07    --  -77.65 111.00 -90.00   78
 75  ω    -91.00 -59.00   0.50    0.07    --  -82.00  97.00-153.33   64
 76  ω    -55.00 -30.00   0.50    0.07    --  -82.00  97.00-153.33   50
 77  ω   -133.00 -97.00   0.50    0.07    --  -77.65 -45.00 -90.00   72
 78  ω   -131.00-103.00   0.50    0.07    --  -77.65 -61.00-150.00   56
 79  ω   -129.00 -89.00   0.50    0.07    --  -77.65 -61.00-180.00   80
 80  ω   -122.00 -81.00   0.50    0.07    --  -77.65 -45.00-150.00   82
 81  ω   -110.00 -85.00   0.50    0.07    --  -82.00 -56.00 -50.47   50
 82  ω   -120.00 -72.00   0.50    0.07    --  -66.00 -50.00 -56.32   96
 83  ω   -126.00-100.00   0.50    0.07    --  -77.65 -61.00 150.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, SynergyCustom DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0505761000
_diffrn_orient_matrix_UB_12      -0.0710689000
_diffrn_orient_matrix_UB_13      -0.0167853000
_diffrn_orient_matrix_UB_21      0.0537313000
_diffrn_orient_matrix_UB_22      0.0444824000
_diffrn_orient_matrix_UB_23      -0.0992225000
_diffrn_orient_matrix_UB_31      0.0499441000
_diffrn_orient_matrix_UB_32      0.0240491000
_diffrn_orient_matrix_UB_33      0.1340480000
_diffrn_oxdiff_digest_hkl        
;
43c81c66059044315e495d49ebab8fee865c78
;
_diffrn_oxdiff_digest_od_ed      
;

;
_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         0.890
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                5288
_reflns_number_total             5763
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.44.103a (Rigaku OD, 2025)'
_computing_data_collection       
'CrysAlisPro system (CCD 44.103a 64-bit (release 31-03-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.44.103a (Rigaku OD, 2025)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 2294 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         5763
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+0.3613P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1003
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C7-C14 \\sim C7-C14A
 with sigma of 0.02
3. Others
 Sof(C14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=
 Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=1-FVAR(1)
 Sof(C14)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(C18)=
 Sof(H18)=Sof(C19)=Sof(H19)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C6(H6), C8(H8)
4.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C9(H9A,H9B), C12(H12A,H12B)
4.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25), C15A(H15A), C16A(H16A), C17A(H17A), C18A(H18A),
 C19A(H19A)
4.d Fitted hexagon refined as free rotating group:
 C14(C15,C16,C17,C18,C19), C14A(C15A,C16A,C17A,C18A,C19A)
4.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
4.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
F1 F 0.73523(9) 0.57958(11) -0.18857(15) 0.0522(4) Uani 1 1 d . . . . .
F2 F 0.76746(9) 0.56355(10) 0.03837(16) 0.0483(4) Uani 1 1 d . . . . .
F3 F 0.73213(10) 0.67391(10) -0.04043(18) 0.0535(4) Uani 1 1 d . . . . .
O1 O 0.58374(11) 0.61474(10) -0.12373(17) 0.0400(4) Uani 1 1 d . . . . .
H1 H 0.593187 0.598525 -0.207138 0.060 Uiso 1 1 calc R U . . .
O2 O 0.62636(11) 0.45157(11) -0.12422(17) 0.0418(4) Uani 1 1 d . . . . .
O3 O 0.66553(10) 0.36541(11) 0.22912(18) 0.0416(4) Uani 1 1 d . . . . .
O4 O 0.58900(11) 0.55629(10) 0.60296(16) 0.0385(4) Uani 1 1 d . . . . .
O5 O 0.60350(10) 0.64486(9) 0.42950(16) 0.0361(4) Uani 1 1 d . . . . .
N1 N 0.60760(12) 0.47231(11) 0.1190(2) 0.0344(4) Uani 1 1 d . . . . .
C1 C 0.63442(14) 0.58019(14) -0.0200(2) 0.0345(5) Uani 1 1 d . . . . .
C2 C 0.62338(14) 0.49381(14) -0.0202(2) 0.0342(5) Uani 1 1 d . . . . .
C3 C 0.60909(14) 0.53191(14) 0.2184(2) 0.0327(5) Uani 1 1 d . . . . .
C4 C 0.61560(15) 0.60479(14) 0.1352(2) 0.0365(5) Uani 1 1 d . . . . .
H4A H 0.657381 0.636952 0.177976 0.044 Uiso 1 1 calc R U . . .
H4B H 0.566374 0.633342 0.135285 0.044 Uiso 1 1 calc R U . . .
C5 C 0.60311(14) 0.51620(13) 0.3615(3) 0.0327(5) Uani 1 1 d . . . . .
C6 C 0.59622(14) 0.43327(13) 0.4038(2) 0.0333(5) Uani 1 1 d . . . . .
H6 H 0.577457 0.427650 0.504853 0.040 Uiso 1 1 calc R U . . .
C7 C 0.67084(14) 0.38679(14) 0.3826(2) 0.0357(5) Uani 1 1 d D . . . .
C8 C 0.59592(15) 0.39397(14) 0.1671(3) 0.0365(5) Uani 1 1 d . . . . .
H8 H 0.575786 0.361225 0.085475 0.044 Uiso 1 1 calc R U . . .
C9 C 0.54115(14) 0.39524(14) 0.2923(2) 0.0356(5) Uani 1 1 d . . . . .
H9A H 0.525928 0.343734 0.322656 0.043 Uiso 1 1 calc R U . . .
H9B H 0.494449 0.426120 0.270225 0.043 Uiso 1 1 calc R U . . .
C10 C 0.71741(16) 0.59951(15) -0.0533(3) 0.0409(6) Uani 1 1 d . . . . .
C11 C 0.59865(14) 0.57305(13) 0.4754(2) 0.0332(5) Uani 1 1 d . . . . .
C12 C 0.60024(16) 0.70325(13) 0.5419(3) 0.0381(5) Uani 1 1 d . . . . .
H12A H 0.643366 0.696961 0.614492 0.046 Uiso 1 1 calc R U . . .
H12B H 0.550783 0.700265 0.592509 0.046 Uiso 1 1 calc R U . . .
C13 C 0.60682(17) 0.77834(15) 0.4638(3) 0.0449(6) Uani 1 1 d . . . . .
H13A H 0.565341 0.782502 0.388881 0.067 Uiso 1 1 calc R U . . .
H13B H 0.657049 0.781354 0.418156 0.067 Uiso 1 1 calc R U . . .
H13C H 0.602334 0.819774 0.533924 0.067 Uiso 1 1 calc R U . . .
C14 C 0.7464(3) 0.4306(3) 0.4214(9) 0.0383(15) Uani 0.75(2) 1 d DG . P A 1
C15 C 0.7637(2) 0.4553(3) 0.5623(10) 0.0438(14) Uani 0.75(2) 1 d G . P A 1
H15 H 0.727283 0.448700 0.636061 0.053 Uiso 0.75(2) 1 calc R U P A 1
C16 C 0.8344(2) 0.4898(3) 0.5952(13) 0.056(2) Uani 0.75(2) 1 d G . P A 1
H16 H 0.846277 0.506714 0.691529 0.068 Uiso 0.75(2) 1 calc R U P A 1
C17 C 0.88779(18) 0.4995(2) 0.4873(15) 0.069(3) Uani 0.75(2) 1 d G . P A 1
H17 H 0.936098 0.523070 0.509770 0.083 Uiso 0.75(2) 1 calc R U P A 1
C18 C 0.8705(3) 0.4748(3) 0.3463(13) 0.060(2) Uani 0.75(2) 1 d G . P A 1
H18 H 0.906925 0.481412 0.272542 0.072 Uiso 0.75(2) 1 calc R U P A 1
C19 C 0.7998(3) 0.4403(3) 0.3134(10) 0.0502(17) Uani 0.75(2) 1 d G . P A 1
H19 H 0.787931 0.423399 0.217072 0.060 Uiso 0.75(2) 1 calc R U P A 1
C20 C 0.67316(14) 0.31373(14) 0.4727(3) 0.0354(5) Uani 1 1 d . . . . .
C21 C 0.65738(17) 0.31488(15) 0.6208(3) 0.0423(6) Uani 1 1 d . . . . .
H21 H 0.641061 0.360547 0.664812 0.051 Uiso 1 1 calc R U . . .
C22 C 0.6655(2) 0.24913(18) 0.7039(3) 0.0522(7) Uani 1 1 d . . . . .
H22 H 0.654655 0.250258 0.804461 0.063 Uiso 1 1 calc R U . . .
C23 C 0.68942(18) 0.18218(16) 0.6410(3) 0.0479(6) Uani 1 1 d . . . . .
H23 H 0.694883 0.137490 0.697933 0.057 Uiso 1 1 calc R U . . .
C24 C 0.70515(16) 0.18099(14) 0.4954(3) 0.0416(6) Uani 1 1 d . . . . .
H24 H 0.721286 0.135133 0.451849 0.050 Uiso 1 1 calc R U . . .
C25 C 0.69769(15) 0.24625(14) 0.4113(3) 0.0384(5) Uani 1 1 d . . . . .
H25 H 0.709426 0.244720 0.311228 0.046 Uiso 1 1 calc R U . . .
C14A C 0.7484(7) 0.4282(10) 0.3828(16) 0.033(4) Uani 0.25(2) 1 d DG . P A 2
C15A C 0.7731(9) 0.4610(9) 0.5139(16) 0.035(3) Uani 0.25(2) 1 d G . P A 2
H15A H 0.739945 0.461358 0.594015 0.042 Uiso 0.25(2) 1 calc R U P A 2
C16A C 0.8463(10) 0.4932(6) 0.5276(19) 0.037(4) Uani 0.25(2) 1 d G . P A 2
H16A H 0.863154 0.515573 0.617130 0.045 Uiso 0.25(2) 1 calc R U P A 2
C17A C 0.8948(8) 0.4926(9) 0.410(2) 0.043(4) Uani 0.25(2) 1 d G . P A 2
H17A H 0.944847 0.514594 0.419688 0.052 Uiso 0.25(2) 1 calc R U P A 2
C18A C 0.8702(7) 0.4598(11) 0.2793(19) 0.052(5) Uani 0.25(2) 1 d G . P A 2
H18A H 0.903332 0.459400 0.199128 0.062 Uiso 0.25(2) 1 calc R U P A 2
C19A C 0.7970(8) 0.4276(11) 0.2656(15) 0.050(4) Uani 0.25(2) 1 d G . P A 2
H19A H 0.780123 0.405186 0.176009 0.060 Uiso 0.25(2) 1 calc R U P A 2


_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
F1 C10 1.339(3) . ?
F2 C10 1.346(3) . ?
F3 C10 1.343(3) . ?
O1 H1 0.8400 . ?
O1 C1 1.411(3) . ?
O2 C2 1.215(3) . ?
O3 C7 1.460(3) . ?
O3 C8 1.408(3) . ?
O4 C11 1.227(3) . ?
O5 C11 1.340(3) . ?
O5 C12 1.462(3) . ?
N1 C2 1.372(3) . ?
N1 C3 1.394(3) . ?
N1 C8 1.469(3) . ?
C1 C2 1.538(3) . ?
C1 C4 1.537(3) . ?
C1 C10 1.518(4) . ?
C3 C4 1.504(3) . ?
C3 C5 1.352(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.521(3) . ?
C5 C11 1.455(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.548(3) . ?
C6 C9 1.530(3) . ?
C7 C14 1.550(5) . ?
C7 C20 1.533(3) . ?
C7 C14A 1.529(10) . ?
C8 H8 1.0000 . ?
C8 C9 1.517(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.514(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.3900 . ?
C14 C19 1.3900 . ?
C15 H15 0.9500 . ?
C15 C16 1.3900 . ?
C16 H16 0.9500 . ?
C16 C17 1.3900 . ?
C17 H17 0.9500 . ?
C17 C18 1.3900 . ?
C18 H18 0.9500 . ?
C18 C19 1.3900 . ?
C19 H19 0.9500 . ?
C20 C21 1.398(3) . ?
C20 C25 1.391(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.395(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.386(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.375(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.391(3) . ?
C25 H25 0.9500 . ?
C14A C15A 1.3900 . ?
C14A C19A 1.3900 . ?
C15A H15A 0.9500 . ?
C15A C16A 1.3900 . ?
C16A H16A 0.9500 . ?
C16A C17A 1.3900 . ?
C17A H17A 0.9500 . ?
C17A C18A 1.3900 . ?
C18A H18A 0.9500 . ?
C18A C19A 1.3900 . ?
C19A H19A 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
C1 O1 H1 109.5 . . ?
C8 O3 C7 108.82(18) . . ?
C11 O5 C12 116.13(17) . . ?
C2 N1 C3 113.78(19) . . ?
C2 N1 C8 125.12(19) . . ?
C3 N1 C8 120.93(18) . . ?
O1 C1 C2 110.72(19) . . ?
O1 C1 C4 111.0(2) . . ?
O1 C1 C10 109.63(19) . . ?
C4 C1 C2 104.56(19) . . ?
C10 C1 C2 109.9(2) . . ?
C10 C1 C4 110.91(19) . . ?
O2 C2 N1 125.4(2) . . ?
O2 C2 C1 127.0(2) . . ?
N1 C2 C1 107.59(19) . . ?
N1 C3 C4 108.21(18) . . ?
C5 C3 N1 118.9(2) . . ?
C5 C3 C4 132.9(2) . . ?
C1 C4 H4A 110.8 . . ?
C1 C4 H4B 110.8 . . ?
C3 C4 C1 104.6(2) . . ?
C3 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
C3 C5 C6 117.1(2) . . ?
C3 C5 C11 124.5(2) . . ?
C11 C5 C6 118.29(19) . . ?
C5 C6 H6 111.3 . . ?
C5 C6 C7 113.9(2) . . ?
C5 C6 C9 107.70(18) . . ?
C7 C6 H6 111.3 . . ?
C9 C6 H6 111.3 . . ?
C9 C6 C7 100.68(19) . . ?
O3 C7 C6 103.56(18) . . ?
O3 C7 C14 112.0(3) . . ?
O3 C7 C20 107.71(19) . . ?
O3 C7 C14A 98.6(6) . . ?
C6 C7 C14 114.0(3) . . ?
C20 C7 C6 112.6(2) . . ?
C20 C7 C14 106.9(3) . . ?
C14A C7 C6 118.9(7) . . ?
C14A C7 C20 113.3(7) . . ?
O3 C8 N1 109.5(2) . . ?
O3 C8 H8 111.6 . . ?
O3 C8 C9 104.25(18) . . ?
N1 C8 H8 111.6 . . ?
N1 C8 C9 108.1(2) . . ?
C9 C8 H8 111.6 . . ?
C6 C9 H9A 112.3 . . ?
C6 C9 H9B 112.3 . . ?
C8 C9 C6 97.12(19) . . ?
C8 C9 H9A 112.3 . . ?
C8 C9 H9B 112.3 . . ?
H9A C9 H9B 109.9 . . ?
F1 C10 F2 107.1(2) . . ?
F1 C10 F3 106.9(2) . . ?
F1 C10 C1 112.3(2) . . ?
F2 C10 C1 111.1(2) . . ?
F3 C10 F2 106.9(2) . . ?
F3 C10 C1 112.3(2) . . ?
O4 C11 O5 122.8(2) . . ?
O4 C11 C5 122.3(2) . . ?
O5 C11 C5 114.88(19) . . ?
O5 C12 H12A 110.5 . . ?
O5 C12 H12B 110.5 . . ?
O5 C12 C13 106.11(19) . . ?
H12A C12 H12B 108.7 . . ?
C13 C12 H12A 110.5 . . ?
C13 C12 H12B 110.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C7 121.6(3) . . ?
C15 C14 C19 120.0 . . ?
C19 C14 C7 118.3(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18 120.0 . . ?
C14 C19 H19 120.0 . . ?
C18 C19 C14 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C7 120.8(2) . . ?
C25 C20 C7 120.3(2) . . ?
C25 C20 C21 118.7(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.2(2) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.5(2) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.3 . . ?
C24 C23 C22 119.4(2) . . ?
C24 C23 H23 120.3 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.7(2) . . ?
C25 C24 H24 119.7 . . ?
C20 C25 C24 120.5(2) . . ?
C20 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C15A C14A C7 116.3(8) . . ?
C15A C14A C19A 120.0 . . ?
C19A C14A C7 123.4(8) . . ?
C14A C15A H15A 120.0 . . ?
C14A C15A C16A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C15A C16A C17A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C16A C17A H17A 120.0 . . ?
C18A C17A C16A 120.0 . . ?
C18A C17A H17A 120.0 . . ?
C17A C18A H18A 120.0 . . ?
C19A C18A C17A 120.0 . . ?
C19A C18A H18A 120.0 . . ?
C14A C19A H19A 120.0 . . ?
C18A C19A C14A 120.0 . . ?
C18A C19A H19A 120.0 . . ?

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 O2 54.2(3) . . . . ?
O1 C1 C2 N1 -124.4(2) . . . . ?
O1 C1 C4 C3 128.9(2) . . . . ?
O1 C1 C10 F1 -56.3(3) . . . . ?
O1 C1 C10 F2 -176.17(19) . . . . ?
O1 C1 C10 F3 64.2(2) . . . . ?
O3 C7 C14 C15 -179.0(3) . . . . ?
O3 C7 C14 C19 -3.4(4) . . . . ?
O3 C7 C20 C21 -162.6(2) . . . . ?
O3 C7 C20 C25 23.0(3) . . . . ?
O3 C7 C14A C15A 177.3(8) . . . . ?
O3 C7 C14A C19A -9.2(10) . . . . ?
O3 C8 C9 C6 47.6(2) . . . . ?
N1 C3 C4 C1 -11.2(2) . . . . ?
N1 C3 C5 C6 0.8(3) . . . . ?
N1 C3 C5 C11 -175.7(2) . . . . ?
N1 C8 C9 C6 -68.9(2) . . . . ?
C2 N1 C3 C4 8.9(3) . . . . ?
C2 N1 C3 C5 -172.6(2) . . . . ?
C2 N1 C8 O3 96.6(3) . . . . ?
C2 N1 C8 C9 -150.3(2) . . . . ?
C2 C1 C4 C3 9.5(2) . . . . ?
C2 C1 C10 F1 65.6(3) . . . . ?
C2 C1 C10 F2 -54.2(3) . . . . ?
C2 C1 C10 F3 -173.88(19) . . . . ?
C3 N1 C2 O2 178.9(2) . . . . ?
C3 N1 C2 C1 -2.4(3) . . . . ?
C3 N1 C8 O3 -78.4(3) . . . . ?
C3 N1 C8 C9 34.6(3) . . . . ?
C3 C5 C6 C7 69.0(3) . . . . ?
C3 C5 C6 C9 -41.7(3) . . . . ?
C3 C5 C11 O4 175.9(2) . . . . ?
C3 C5 C11 O5 -2.1(3) . . . . ?
C4 C1 C2 O2 173.8(2) . . . . ?
C4 C1 C2 N1 -4.8(3) . . . . ?
C4 C1 C10 F1 -179.2(2) . . . . ?
C4 C1 C10 F2 60.9(3) . . . . ?
C4 C1 C10 F3 -58.7(2) . . . . ?
C4 C3 C5 C6 179.0(2) . . . . ?
C4 C3 C5 C11 2.5(4) . . . . ?
C5 C3 C4 C1 170.5(3) . . . . ?
C5 C6 C7 O3 -84.2(2) . . . . ?
C5 C6 C7 C14 37.8(4) . . . . ?
C5 C6 C7 C20 159.76(18) . . . . ?
C5 C6 C7 C14A 23.9(7) . . . . ?
C5 C6 C9 C8 73.1(2) . . . . ?
C6 C5 C11 O4 -0.6(3) . . . . ?
C6 C5 C11 O5 -178.6(2) . . . . ?
C6 C7 C14 C15 63.8(4) . . . . ?
C6 C7 C14 C19 -120.6(3) . . . . ?
C6 C7 C20 C21 -49.1(3) . . . . ?
C6 C7 C20 C25 136.6(2) . . . . ?
C6 C7 C14A C15A 66.6(10) . . . . ?
C6 C7 C14A C19A -120.0(8) . . . . ?
C7 O3 C8 N1 85.8(2) . . . . ?
C7 O3 C8 C9 -29.7(2) . . . . ?
C7 C6 C9 C8 -46.4(2) . . . . ?
C7 C14 C15 C16 175.5(5) . . . . ?
C7 C14 C19 C18 -175.7(5) . . . . ?
C7 C20 C21 C22 -175.0(3) . . . . ?
C7 C20 C25 C24 175.4(2) . . . . ?
C7 C14A C15A C16A 173.7(14) . . . . ?
C7 C14A C19A C18A -173.2(15) . . . . ?
C8 O3 C7 C6 -1.1(2) . . . . ?
C8 O3 C7 C14 -124.4(3) . . . . ?
C8 O3 C7 C20 118.3(2) . . . . ?
C8 O3 C7 C14A -123.7(8) . . . . ?
C8 N1 C2 O2 3.6(4) . . . . ?
C8 N1 C2 C1 -177.7(2) . . . . ?
C8 N1 C3 C4 -175.6(2) . . . . ?
C8 N1 C3 C5 3.0(3) . . . . ?
C9 C6 C7 O3 30.8(2) . . . . ?
C9 C6 C7 C14 152.8(3) . . . . ?
C9 C6 C7 C20 -85.3(2) . . . . ?
C9 C6 C7 C14A 138.8(7) . . . . ?
C10 C1 C2 O2 -67.0(3) . . . . ?
C10 C1 C2 N1 114.3(2) . . . . ?
C10 C1 C4 C3 -108.9(2) . . . . ?
C11 O5 C12 C13 180.0(2) . . . . ?
C11 C5 C6 C7 -114.2(2) . . . . ?
C11 C5 C6 C9 135.0(2) . . . . ?
C12 O5 C11 O4 2.8(3) . . . . ?
C12 O5 C11 C5 -179.2(2) . . . . ?
C14 C7 C20 C21 76.8(4) . . . . ?
C14 C7 C20 C25 -97.5(4) . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C14 C19 C18 0.0 . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C17 C18 C19 C14 0.0 . . . . ?
C19 C14 C15 C16 0.0 . . . . ?
C20 C7 C14 C15 -61.3(4) . . . . ?
C20 C7 C14 C19 114.3(3) . . . . ?
C20 C7 C14A C15A -69.1(10) . . . . ?
C20 C7 C14A C19A 104.4(9) . . . . ?
C20 C21 C22 C23 0.1(5) . . . . ?
C21 C20 C25 C24 1.0(4) . . . . ?
C21 C22 C23 C24 0.1(5) . . . . ?
C22 C23 C24 C25 0.3(4) . . . . ?
C23 C24 C25 C20 -0.8(4) . . . . ?
C25 C20 C21 C22 -0.6(4) . . . . ?
C14A C7 C20 C21 89.4(7) . . . . ?
C14A C7 C20 C25 -85.0(7) . . . . ?
C14A C15A C16A C17A 0.0 . . . . ?
C15A C14A C19A C18A 0.0 . . . . ?
C15A C16A C17A C18A 0.0 . . . . ?
C16A C17A C18A C19A 0.0 . . . . ?
C17A C18A C19A C14A 0.0 . . . . ?
C19A C14A C15A C16A 0.0 . . . . ?

_platon_squeeze_details          ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.491 -0.002 400 106 '2 C6H14'
2 0.500 0.991 0.985 400 106 '2 C6H14'

_platon_squeeze_void_probe_radius 1.20
_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 3.463
_oxdiff_exptl_absorpt_empirical_full_min 0.456
####################################################################### 
# 
# 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_37-cr-20250707b_auto
_database_code_depnum_ccdc_archive 'CCDC 2489425'
loop_
_audit_author_name
_audit_author_address
'Dengke Ma'
;Capital Medical University
China
;
_audit_update_record             
;
2025-09-18 deposited with the CCDC.	2026-06-05 downloaded from the CCDC.
;
_audit_creation_date             2025-07-08
_audit_creation_method           
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H23 N O3'
_chemical_formula_sum            'C24 H23 N O3'
_chemical_formula_weight         373.43
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.19220(10)
_cell_length_b                   10.06450(10)
_cell_length_c                   20.9027(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1933.81(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7745
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.3590
_cell_measurement_theta_min      4.2240
_shelx_estimated_absorpt_T_max   0.877
_shelx_estimated_absorpt_T_min   0.844
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.103a (Rigaku Oxford Diffraction, 2025)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19020
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.009
_diffrn_reflns_theta_min         4.230
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00 -10.00   0.50    0.15    --  -63.54  61.00 -30.00   58
  2  ω    -48.00 -22.00   0.50    0.15    --  -63.54  61.00  65.00   52
  3  ω    -54.00 -29.00   0.50    0.15    --  -77.65  61.00  65.00   50
  4  ω    -77.00 -31.00   0.50    0.15    --  -77.65  77.00 120.00   92
  5  ω    -52.00 -27.00   0.50    0.15    --  -77.65  61.00 120.00   50
  6  ω    -40.00 -15.00   0.50    0.15    --  -63.54  59.00-104.00   50
  7  ω    -49.00 -24.00   0.50    0.15    --  -54.64  59.00-104.00   50
  8  ω    -51.00 -26.00   0.50    0.15    --  -77.65  59.00-104.00   50
  9  ω    -52.00 -27.00   0.50    0.15    --  -54.64  61.00  65.00   50
 10  ω    102.00 147.00   0.50    0.15    --   93.58  30.00  60.00   90
 11  ω    104.00 131.00   0.50    0.15    --   93.58  59.00-104.00   54
 12  ω    107.00 138.00   0.50    0.15    --   93.58  61.00-150.00   62
 13  ω     96.00 139.00   0.50    0.15    --   93.58  61.00 -90.00   86
 14  ω     98.00 124.00   0.50    0.15    --   93.58  61.00  65.00   52
 15  ω     95.00 143.00   0.50    0.15    --   93.58  61.00 120.00   96
 16  ω    116.00 141.00   0.50    0.15    --   93.58 111.00 150.00   50
 17  ω    103.00 128.00   0.50    0.15    --   93.58 125.00 129.00   50
 18  ω     96.00 144.00   0.50    0.15    --   93.58 111.00 120.00   96
 19  ω     98.00 147.00   0.50    0.15    --   93.58 111.00 -60.00   98
 20  ω     47.00  93.00   0.50    0.15    --   93.58 -94.00-120.00   92
 21  ω     48.00  89.00   0.50    0.15    --   93.58-111.00 -60.00   82
 22  ω     45.00  70.00   0.50    0.15    --   93.58-125.00  51.00   50
 23  ω     48.00  74.00   0.50    0.15    --   93.58-111.00  60.00   52
 24  ω     56.00  82.00   0.50    0.15    --   93.58 -94.00  90.00   52
 25  ω     55.00  80.00   0.50    0.15    --   93.58 -94.00 150.00   50
 26  ω     13.00  58.00   0.50    0.15    --   62.12-125.00  51.00   90
 27  ω     50.00  76.00   0.50    0.15    --   93.58 -94.00 120.00   52
 28  ω     11.00  36.00   0.50    0.15    --   53.94-125.00  51.00   50
 29  ω     49.00  75.00   0.50    0.15    --   93.58 -94.00   0.00   52
 30  ω     49.00  90.00   0.50    0.15    --   93.58 -94.00 -60.00   82
 31  ω     45.00  87.00   0.50    0.15    --   93.58 -94.00-150.00   84
 32  ω     55.00  84.00   0.50    0.15    --   93.58 -94.00-180.00   58
 33  ω      7.00  33.00   0.50    0.15    --   53.94 -61.00 -73.00   52
 34  ω      9.00  34.00   0.50    0.15    --   62.12 -61.00 -73.00   50
 35  ω      9.00  34.00   0.50    0.15    --   62.12 -59.00 115.00   50
 36  ω     10.00  44.00   0.50    0.15    --   62.12 -61.00 150.00   68
 37  ω      1.00  26.00   0.50    0.15    --   53.94 -59.00 115.00   50
 38  ω   -131.00-106.00   0.50    0.15    --  -77.65 -59.00 115.00   50
 39  ω   -131.00 -95.00   0.50    0.15    --  -77.65 -61.00  90.00   72
 40  ω   -130.00 -86.00   0.50    0.15    --  -77.65 -61.00 -30.00   88
 41  ω    -90.00 -52.00   0.50    0.15    --  -54.64 125.00 129.00   76
 42  ω    -99.00 -72.00   0.50    0.15    --  -63.54 125.00 129.00   54
 43  ω    -86.00 -61.00   0.50    0.15    --  -77.65 125.00 129.00   50
 44  ω    -58.00 -27.00   0.50    0.15    --  -63.54 125.00 129.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, SynergyCustom DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0002060000
_diffrn_orient_matrix_UB_12      -0.1068672000
_diffrn_orient_matrix_UB_13      -0.0527715000
_diffrn_orient_matrix_UB_21      0.1670339000
_diffrn_orient_matrix_UB_22      -0.0088669000
_diffrn_orient_matrix_UB_23      0.0043050000
_diffrn_orient_matrix_UB_31      -0.0137697000
_diffrn_orient_matrix_UB_32      -0.1092055000
_diffrn_orient_matrix_UB_33      0.0512773000
_diffrn_oxdiff_digest_od_ed      
;

;
_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         0.739
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                3961
_reflns_number_total             4009
_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 1.171.44.103a (Rigaku OD, 2025)'
_computing_data_collection       'CrysAlisPro 1.171.44.103a (Rigaku OD, 2025)'
_computing_data_reduction        'CrysAlisPro 1.171.44.103a (Rigaku OD, 2025)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1672 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_coef       0.0049(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4009
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0287
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²+0.4224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0744
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11),
 C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C24(H24A,H24B,H24C)
;
_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 0.57520(11) 0.62499(10) 0.60863(5) 0.0176(2) Uani 1 1 d . . . . .
O2 O 0.74635(12) 0.17246(10) 0.60464(5) 0.0191(2) Uani 1 1 d . . . . .
O3 O 0.67613(13) 0.14607(12) 0.70683(5) 0.0240(3) Uani 1 1 d . . . . .
N1 N 0.43262(14) 0.50206(14) 0.68182(6) 0.0190(3) Uani 1 1 d . . . . .
H1 H 0.380426 0.538958 0.712315 0.023 Uiso 1 1 calc R U . . .
C1 C 0.69544(16) 0.57645(15) 0.50838(7) 0.0169(3) Uani 1 1 d . . . . .
C2 C 0.61360(18) 0.68296(15) 0.48472(8) 0.0199(3) Uani 1 1 d . . . . .
H2 H 0.558285 0.735285 0.513695 0.024 Uiso 1 1 calc R U . . .
C3 C 0.61116(18) 0.71409(17) 0.42012(8) 0.0234(3) Uani 1 1 d . . . . .
H3 H 0.556414 0.788097 0.405418 0.028 Uiso 1 1 calc R U . . .
C4 C 0.68878(19) 0.63701(18) 0.37700(8) 0.0250(4) Uani 1 1 d . . . . .
H4 H 0.683384 0.654816 0.332428 0.030 Uiso 1 1 calc R U . . .
C5 C 0.77414(19) 0.53392(17) 0.39953(8) 0.0234(3) Uani 1 1 d . . . . .
H5 H 0.828922 0.482520 0.369987 0.028 Uiso 1 1 calc R U . . .
C6 C 0.78182(17) 0.50332(16) 0.46511(7) 0.0188(3) Uani 1 1 d . . . . .
C7 C 0.88130(18) 0.39632(16) 0.48333(8) 0.0205(3) Uani 1 1 d . . . . .
H7 H 0.906170 0.336308 0.449998 0.025 Uiso 1 1 calc R U . . .
C8 C 0.94238(18) 0.37068(16) 0.54019(8) 0.0202(3) Uani 1 1 d . . . . .
H8 H 1.002097 0.293701 0.541635 0.024 Uiso 1 1 calc R U . . .
C9 C 0.93049(16) 0.44392(15) 0.60029(7) 0.0186(3) Uani 1 1 d . . . . .
C10 C 1.04614(18) 0.42974(18) 0.64398(8) 0.0245(4) Uani 1 1 d . . . . .
H10 H 1.122386 0.369261 0.634324 0.029 Uiso 1 1 calc R U . . .
C11 C 1.05223(18) 0.5008(2) 0.70030(8) 0.0294(4) Uani 1 1 d . . . . .
H11 H 1.131399 0.489047 0.728962 0.035 Uiso 1 1 calc R U . . .
C12 C 0.94186(19) 0.58954(19) 0.71470(8) 0.0277(4) Uani 1 1 d . . . . .
H12 H 0.946870 0.641765 0.752488 0.033 Uiso 1 1 calc R U . . .
C13 C 0.82357(18) 0.60189(17) 0.67359(8) 0.0218(3) Uani 1 1 d . . . . .
H13 H 0.747349 0.661630 0.684289 0.026 Uiso 1 1 calc R U . . .
C14 C 0.81412(17) 0.52871(15) 0.61703(7) 0.0173(3) Uani 1 1 d . . . . .
C15 C 0.67432(16) 0.53217(14) 0.57809(7) 0.0155(3) Uani 1 1 d . . . . .
C16 C 0.43763(16) 0.56133(16) 0.61901(7) 0.0182(3) Uani 1 1 d . . . . .
H16 H 0.355452 0.625147 0.612804 0.022 Uiso 1 1 calc R U . . .
C17 C 0.43377(16) 0.45174(15) 0.56904(7) 0.0177(3) Uani 1 1 d . . . . .
H17A H 0.420666 0.487045 0.525206 0.021 Uiso 1 1 calc R U . . .
H17B H 0.357945 0.384557 0.578246 0.021 Uiso 1 1 calc R U . . .
C18 C 0.58773(16) 0.39774(15) 0.58006(7) 0.0149(3) Uani 1 1 d . . . . .
H18 H 0.618762 0.335479 0.545359 0.018 Uiso 1 1 calc R U . . .
C19 C 0.58987(16) 0.33176(15) 0.64575(7) 0.0153(3) Uani 1 1 d . . . . .
C20 C 0.50883(17) 0.38903(16) 0.69369(7) 0.0170(3) Uani 1 1 d . . . . .
C21 C 0.4930(2) 0.33791(18) 0.76085(8) 0.0242(4) Uani 1 1 d . . . . .
H21A H 0.433298 0.399753 0.785770 0.036 Uiso 1 1 calc R U . . .
H21B H 0.589371 0.330126 0.780578 0.036 Uiso 1 1 calc R U . . .
H21C H 0.446134 0.250479 0.760006 0.036 Uiso 1 1 calc R U . . .
C22 C 0.67127(16) 0.21042(15) 0.65718(7) 0.0160(3) Uani 1 1 d . . . . .
C23 C 0.82759(18) 0.04953(15) 0.60852(8) 0.0206(3) Uani 1 1 d . . . . .
H23A H 0.852381 0.030466 0.653688 0.025 Uiso 1 1 calc R U . . .
H23B H 0.919374 0.057916 0.584074 0.025 Uiso 1 1 calc R U . . .
C24 C 0.73735(19) -0.06298(16) 0.58144(9) 0.0253(4) Uani 1 1 d . . . . .
H24A H 0.708922 -0.041653 0.537436 0.038 Uiso 1 1 calc R U . . .
H24B H 0.649946 -0.075088 0.607648 0.038 Uiso 1 1 calc R U . . .
H24C H 0.794736 -0.145034 0.581704 0.038 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.4528(17) . ?
O1 C16 1.4342(19) . ?
O2 C22 1.3522(18) . ?
O2 C23 1.4475(17) . ?
O3 C22 1.2241(19) . ?
N1 H1 0.8800 . ?
N1 C16 1.443(2) . ?
N1 C20 1.359(2) . ?
C1 C2 1.400(2) . ?
C1 C6 1.411(2) . ?
C1 C15 1.536(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.407(2) . ?
C6 C7 1.463(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.340(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.461(2) . ?
C9 C10 1.409(2) . ?
C9 C14 1.412(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.391(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.396(2) . ?
C14 C15 1.522(2) . ?
C15 C18 1.570(2) . ?
C16 H16 1.0000 . ?
C16 C17 1.519(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.533(2) . ?
C18 H18 1.0000 . ?
C18 C19 1.5255(19) . ?
C19 C20 1.375(2) . ?
C19 C22 1.452(2) . ?
C20 C21 1.502(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.513(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
C16 O1 C15 109.40(11) . . ?
C22 O2 C23 117.34(12) . . ?
C16 N1 H1 120.1 . . ?
C20 N1 H1 120.1 . . ?
C20 N1 C16 119.73(13) . . ?
C2 C1 C6 118.39(14) . . ?
C2 C1 C15 119.30(13) . . ?
C6 C1 C15 121.87(13) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.72(15) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.89(16) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.34(15) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.63(15) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C7 124.67(14) . . ?
C5 C6 C1 118.84(15) . . ?
C5 C6 C7 116.49(14) . . ?
C6 C7 H7 115.3 . . ?
C8 C7 C6 129.39(15) . . ?
C8 C7 H7 115.3 . . ?
C7 C8 H8 115.3 . . ?
C7 C8 C9 129.39(15) . . ?
C9 C8 H8 115.3 . . ?
C10 C9 C8 116.74(14) . . ?
C10 C9 C14 118.18(15) . . ?
C14 C9 C8 125.07(14) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 C9 122.11(16) . . ?
C11 C10 H10 118.9 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.37(16) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.74(16) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.65(16) . . ?
C14 C13 H13 119.2 . . ?
C9 C14 C15 121.39(13) . . ?
C13 C14 C9 118.78(14) . . ?
C13 C14 C15 119.59(14) . . ?
O1 C15 C1 108.03(12) . . ?
O1 C15 C14 108.01(12) . . ?
O1 C15 C18 102.98(11) . . ?
C1 C15 C18 109.81(12) . . ?
C14 C15 C1 114.04(12) . . ?
C14 C15 C18 113.23(12) . . ?
O1 C16 N1 110.51(12) . . ?
O1 C16 H16 111.1 . . ?
O1 C16 C17 103.94(12) . . ?
N1 C16 H16 111.1 . . ?
N1 C16 C17 108.95(13) . . ?
C17 C16 H16 111.1 . . ?
C16 C17 H17A 112.2 . . ?
C16 C17 H17B 112.2 . . ?
C16 C17 C18 97.61(12) . . ?
H17A C17 H17B 109.8 . . ?
C18 C17 H17A 112.2 . . ?
C18 C17 H17B 112.2 . . ?
C15 C18 H18 112.1 . . ?
C17 C18 C15 99.12(12) . . ?
C17 C18 H18 112.1 . . ?
C19 C18 C15 113.09(12) . . ?
C19 C18 C17 107.54(12) . . ?
C19 C18 H18 112.1 . . ?
C20 C19 C18 117.81(13) . . ?
C20 C19 C22 120.78(13) . . ?
C22 C19 C18 121.39(13) . . ?
N1 C20 C19 119.80(14) . . ?
N1 C20 C21 114.06(14) . . ?
C19 C20 C21 126.14(14) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 C22 C19 111.53(12) . . ?
O3 C22 O2 121.37(14) . . ?
O3 C22 C19 127.10(14) . . ?
O2 C23 H23A 109.7 . . ?
O2 C23 H23B 109.7 . . ?
O2 C23 C24 109.62(13) . . ?
H23A C23 H23B 108.2 . . ?
C24 C23 H23A 109.7 . . ?
C24 C23 H23B 109.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C15 C18 C17 36.20(13) . . . . ?
O1 C15 C18 C19 -77.39(14) . . . . ?
O1 C16 C17 C18 46.30(13) . . . . ?
N1 C16 C17 C18 -71.54(14) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C1 C6 C7 C8 -21.0(3) . . . . ?
C1 C15 C18 C17 -78.68(14) . . . . ?
C1 C15 C18 C19 167.73(12) . . . . ?
C2 C1 C6 C5 -4.6(2) . . . . ?
C2 C1 C6 C7 175.14(15) . . . . ?
C2 C1 C15 O1 -5.27(18) . . . . ?
C2 C1 C15 C14 -125.37(15) . . . . ?
C2 C1 C15 C18 106.34(15) . . . . ?
C2 C3 C4 C5 -3.4(3) . . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
C4 C5 C6 C1 2.7(2) . . . . ?
C4 C5 C6 C7 -177.11(15) . . . . ?
C5 C6 C7 C8 158.76(17) . . . . ?
C6 C1 C2 C3 2.7(2) . . . . ?
C6 C1 C15 O1 -177.52(13) . . . . ?
C6 C1 C15 C14 62.39(18) . . . . ?
C6 C1 C15 C18 -65.90(18) . . . . ?
C6 C7 C8 C9 -1.7(3) . . . . ?
C7 C8 C9 C10 -154.98(18) . . . . ?
C7 C8 C9 C14 23.8(3) . . . . ?
C8 C9 C10 C11 175.44(16) . . . . ?
C8 C9 C14 C13 -174.15(15) . . . . ?
C8 C9 C14 C15 11.4(2) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C9 C14 C15 O1 178.04(13) . . . . ?
C9 C14 C15 C1 -61.86(18) . . . . ?
C9 C14 C15 C18 64.66(18) . . . . ?
C10 C9 C14 C13 4.6(2) . . . . ?
C10 C9 C14 C15 -169.78(14) . . . . ?
C10 C11 C12 C13 2.6(3) . . . . ?
C11 C12 C13 C14 -1.3(3) . . . . ?
C12 C13 C14 C9 -2.4(2) . . . . ?
C12 C13 C14 C15 172.14(15) . . . . ?
C13 C14 C15 O1 3.67(18) . . . . ?
C13 C14 C15 C1 123.77(15) . . . . ?
C13 C14 C15 C18 -109.70(16) . . . . ?
C14 C9 C10 C11 -3.4(2) . . . . ?
C14 C15 C18 C17 152.58(12) . . . . ?
C14 C15 C18 C19 38.99(17) . . . . ?
C15 O1 C16 N1 92.44(14) . . . . ?
C15 O1 C16 C17 -24.31(15) . . . . ?
C15 C1 C2 C3 -169.84(15) . . . . ?
C15 C1 C6 C5 167.71(14) . . . . ?
C15 C1 C6 C7 -12.5(2) . . . . ?
C15 C18 C19 C20 72.07(17) . . . . ?
C15 C18 C19 C22 -109.61(15) . . . . ?
C16 O1 C15 C1 108.30(13) . . . . ?
C16 O1 C15 C14 -127.89(12) . . . . ?
C16 O1 C15 C18 -7.85(15) . . . . ?
C16 N1 C20 C19 -0.2(2) . . . . ?
C16 N1 C20 C21 -179.65(14) . . . . ?
C16 C17 C18 C15 -49.14(13) . . . . ?
C16 C17 C18 C19 68.72(14) . . . . ?
C17 C18 C19 C20 -36.31(17) . . . . ?
C17 C18 C19 C22 142.01(14) . . . . ?
C18 C19 C20 N1 -1.2(2) . . . . ?
C18 C19 C20 C21 178.23(15) . . . . ?
C18 C19 C22 O2 3.31(19) . . . . ?
C18 C19 C22 O3 -176.78(15) . . . . ?
C20 N1 C16 O1 -73.82(17) . . . . ?
C20 N1 C16 C17 39.79(18) . . . . ?
C20 C19 C22 O2 -178.41(13) . . . . ?
C20 C19 C22 O3 1.5(2) . . . . ?
C22 O2 C23 C24 95.57(16) . . . . ?
C22 C19 C20 N1 -179.52(13) . . . . ?
C22 C19 C20 C21 -0.1(2) . . . . ?
C23 O2 C22 O3 2.7(2) . . . . ?
C23 O2 C22 C19 -177.42(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 2.968
_oxdiff_exptl_absorpt_empirical_full_min 0.470
