# Electronic Supplementary Material (ESI) for ChemComm.
# 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_k11008-jjw-b-tpg72
_database_code_depnum_ccdc_archive 'CCDC 2226529'
loop_
_audit_author_name
_audit_author_address
CCDC
;Kaohsiung Medical University Taiwan
Taiwan
;
_audit_update_record             
;
2022-12-14 deposited with the CCDC.	2023-04-11 downloaded from the CCDC.
;
_audit_creation_date             2021-08-06
_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         '2(C24 H16 Cl N O)'
_chemical_formula_sum            'C48 H32 Cl2 N2 O2'
_chemical_formula_weight         739.65
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   8.2282(3)
_cell_length_b                   14.8841(7)
_cell_length_c                   14.9762(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.424(3)
_cell_angle_gamma                90
_cell_volume                     1797.79(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15194
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9060
_cell_measurement_theta_min      1.9610
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23138
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.948
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  51.00   0.50   13.27    --   10.60 -32.00  61.00  260
  2  ω    -30.00 100.00   0.50   13.27    --   10.60  32.00-139.00  260
  3  ω   -100.00  20.00   0.50   13.27    --  -10.90 -32.00  61.00  240
  4  ω    -11.00  14.00   0.50   13.27    --  -10.90  32.00-139.00   50
  5  ω     -8.00 100.00   0.50   13.27    --   10.60  77.00 -60.00  216
  6  ω    -11.00  20.00   0.50   13.27    --   10.60  77.00-180.00   62
  7  ω      9.00  36.00   0.50   13.27    --   10.60 -77.00 -30.00   54
  8  ω    -17.00 100.00   0.50   13.27    --   10.60  82.00-120.00  234
  9  ω    -71.00 -35.00   0.50   13.27    --   10.60 -77.00 -30.00   72
 10  ω     12.00  79.00   0.50   13.27    --  -10.90  77.00 -90.00  134
 11  ω    -33.00  -6.00   0.50   13.27    --  -10.90  77.00 -90.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0042984000
_diffrn_orient_matrix_UB_12      0.0159078000
_diffrn_orient_matrix_UB_13      -0.0450410000
_diffrn_orient_matrix_UB_21      -0.0846892000
_diffrn_orient_matrix_UB_22      -0.0127052000
_diffrn_orient_matrix_UB_23      -0.0113882000
_diffrn_orient_matrix_UB_31      -0.0233858000
_diffrn_orient_matrix_UB_32      0.0430830000
_diffrn_orient_matrix_UB_33      0.0132998000
_diffrn_oxdiff_digest_frames     
;
0177c279a00187cf79c48285598fac73ff00025e8e8
;
_diffrn_oxdiff_digest_hkl        
;
01b66f3e0175365cf159f19185a52e704f44b3
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2786
_reflns_number_total             3163
_reflns_odcompleteness_completeness 98.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3163
_refine_ls_number_restraints     768
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      0.962
_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)+(0.0284P)²+1.3304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0863
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim N1
\\sim O1 \\sim Cl1: within 3.8A with sigma of 0.01 and sigma for terminal atoms
of 0.02
3.a Ternary CH refined with riding coordinates:
 C10(H10), C17(H17), C24(H24)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), 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
Cl1 Cl 0.28501(5) 0.33452(4) 0.32637(3) 0.03544(15) Uani 1 1 d . U . . .
O1 O 0.56694(13) 0.32476(8) 0.77597(7) 0.0207(3) Uani 1 1 d . U . . .
N1 N 1.00563(19) 0.26609(11) 0.62495(11) 0.0310(4) Uani 1 1 d . U . . .
C1 C 0.6610(2) 0.35303(11) 0.71276(11) 0.0195(4) Uani 1 1 d . U . . .
C2 C 0.56741(19) 0.35138(11) 0.61716(11) 0.0197(4) Uani 1 1 d . U . . .
C3 C 0.4209(2) 0.30215(12) 0.59550(12) 0.0243(4) Uani 1 1 d . U . . .
H3 H 0.381610 0.271873 0.641258 0.029 Uiso 1 1 calc R . . . .
C4 C 0.3332(2) 0.29778(13) 0.50663(12) 0.0271(4) Uani 1 1 d . U . . .
H4 H 0.235373 0.264857 0.492649 0.032 Uiso 1 1 calc R . . . .
C5 C 0.3922(2) 0.34275(12) 0.43891(12) 0.0242(4) Uani 1 1 d . U . . .
C6 C 0.5357(2) 0.39340(12) 0.45846(11) 0.0234(4) Uani 1 1 d . U . . .
H6 H 0.573254 0.424371 0.412540 0.028 Uiso 1 1 calc R . . . .
C7 C 0.6228(2) 0.39721(11) 0.54768(11) 0.0213(4) Uani 1 1 d . U . . .
H7 H 0.719686 0.430910 0.561402 0.026 Uiso 1 1 calc R . . . .
C8 C 0.83796(19) 0.31597(11) 0.74513(11) 0.0193(3) Uani 1 1 d . U . . .
C9 C 0.9331(2) 0.28653(12) 0.67966(12) 0.0217(4) Uani 1 1 d . U . . .
C10 C 0.8337(2) 0.26309(11) 0.83178(11) 0.0200(4) Uani 1 1 d . U . . .
H10 H 0.935266 0.274275 0.877007 0.024 Uiso 1 1 calc R . . . .
C11 C 0.80981(19) 0.16329(12) 0.81630(11) 0.0199(4) Uani 1 1 d . U . . .
C12 C 0.9002(2) 0.10262(12) 0.87801(12) 0.0222(4) Uani 1 1 d . U . . .
H12 H 0.978266 0.123992 0.926990 0.027 Uiso 1 1 calc R . . . .
C13 C 0.8748(2) 0.01064(12) 0.86696(12) 0.0260(4) Uani 1 1 d . U . . .
H13 H 0.936217 -0.029116 0.908293 0.031 Uiso 1 1 calc R . . . .
C14 C 0.7581(2) -0.02205(12) 0.79448(12) 0.0269(4) Uani 1 1 d . U . . .
H14 H 0.741309 -0.083617 0.787086 0.032 Uiso 1 1 calc R . . . .
C15 C 0.6667(2) 0.03727(12) 0.73327(12) 0.0264(4) Uani 1 1 d . U . . .
H15 H 0.587299 0.015610 0.685079 0.032 Uiso 1 1 calc R . . . .
C16 C 0.6933(2) 0.12908(12) 0.74363(11) 0.0236(4) Uani 1 1 d . U . . .
H16 H 0.632673 0.168416 0.701528 0.028 Uiso 1 1 calc R . . . .
C17 C 0.6837(2) 0.31049(12) 0.86143(11) 0.0213(4) Uani 1 1 d . U . . .
H17 H 0.635843 0.273347 0.903702 0.026 Uiso 1 1 calc R . . . .
C18 C 0.7343(2) 0.40095(12) 0.90065(11) 0.0223(4) Uani 1 1 d . U . . .
C19 C 0.7169(2) 0.43259(13) 0.98528(12) 0.0278(4) Uani 1 1 d . U . . .
H19 H 0.671176 0.396162 1.024334 0.033 Uiso 1 1 calc R . . . .
C20 C 0.7685(2) 0.51926(13) 1.01116(13) 0.0324(4) Uani 1 1 d . U . . .
H20 H 0.755944 0.541280 1.067520 0.039 Uiso 1 1 calc R . . . .
C21 C 0.8384(2) 0.57300(13) 0.95340(13) 0.0309(4) Uani 1 1 d . U . . .
H21 H 0.874807 0.630449 0.971914 0.037 Uiso 1 1 calc R . . . .
C22 C 0.8548(2) 0.54213(12) 0.86822(12) 0.0255(4) Uani 1 1 d . U . . .
H22 H 0.901477 0.578612 0.829591 0.031 Uiso 1 1 calc R . . . .
C23 C 0.8008(2) 0.45622(12) 0.84136(11) 0.0211(4) Uani 1 1 d . U . . .
C24 C 0.8012(2) 0.41757(11) 0.75044(11) 0.0201(4) Uani 1 1 d . U . . .
H24 H 0.840330 0.456574 0.706386 0.024 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
Cl1 C5 1.7448(17) . ?
O1 C1 1.4010(19) . ?
O1 C17 1.4557(19) . ?
N1 C9 1.146(2) . ?
C1 C2 1.486(2) . ?
C1 C8 1.542(2) . ?
C1 C24 1.521(2) . ?
C2 C3 1.393(2) . ?
C2 C7 1.394(2) . ?
C3 C4 1.384(2) . ?
C4 C5 1.381(3) . ?
C5 C6 1.383(3) . ?
C6 C7 1.387(2) . ?
C8 C9 1.439(2) . ?
C8 C10 1.524(2) . ?
C8 C24 1.547(2) . ?
C10 C11 1.510(2) . ?
C10 C17 1.561(2) . ?
C11 C12 1.397(2) . ?
C11 C16 1.396(2) . ?
C12 C13 1.390(3) . ?
C13 C14 1.387(3) . ?
C14 C15 1.383(3) . ?
C15 C16 1.388(3) . ?
C17 C18 1.495(2) . ?
C18 C19 1.386(2) . ?
C18 C23 1.399(2) . ?
C19 C20 1.389(3) . ?
C20 C21 1.384(3) . ?
C21 C22 1.387(3) . ?
C22 C23 1.387(2) . ?
C23 C24 1.479(2) . ?

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 C17 106.32(12) . . ?
O1 C1 C2 113.32(13) . . ?
O1 C1 C8 107.08(13) . . ?
O1 C1 C24 114.76(13) . . ?
C2 C1 C8 125.03(14) . . ?
C2 C1 C24 125.33(14) . . ?
C24 C1 C8 60.67(11) . . ?
C3 C2 C1 119.52(15) . . ?
C3 C2 C7 118.64(15) . . ?
C7 C2 C1 121.84(15) . . ?
C4 C3 C2 120.73(16) . . ?
C5 C4 C3 119.42(17) . . ?
C4 C5 Cl1 119.45(14) . . ?
C4 C5 C6 121.22(16) . . ?
C6 C5 Cl1 119.32(13) . . ?
C5 C6 C7 118.87(16) . . ?
C6 C7 C2 121.10(16) . . ?
C1 C8 C24 58.98(10) . . ?
C9 C8 C1 120.12(14) . . ?
C9 C8 C10 122.02(14) . . ?
C9 C8 C24 118.11(14) . . ?
C10 C8 C1 105.84(13) . . ?
C10 C8 C24 115.04(13) . . ?
N1 C9 C8 176.92(19) . . ?
C8 C10 C17 99.29(13) . . ?
C11 C10 C8 113.67(14) . . ?
C11 C10 C17 113.70(13) . . ?
C12 C11 C10 119.88(15) . . ?
C16 C11 C10 121.79(15) . . ?
C16 C11 C12 118.27(16) . . ?
C13 C12 C11 120.67(16) . . ?
C14 C13 C12 120.22(17) . . ?
C15 C14 C13 119.73(17) . . ?
C14 C15 C16 120.10(17) . . ?
C15 C16 C11 121.01(16) . . ?
O1 C17 C10 103.73(12) . . ?
O1 C17 C18 107.34(13) . . ?
C18 C17 C10 110.15(14) . . ?
C19 C18 C17 126.46(16) . . ?
C19 C18 C23 120.33(16) . . ?
C23 C18 C17 113.19(15) . . ?
C18 C19 C20 119.32(17) . . ?
C21 C20 C19 120.27(17) . . ?
C20 C21 C22 120.76(18) . . ?
C23 C22 C21 119.20(17) . . ?
C18 C23 C24 115.35(15) . . ?
C22 C23 C18 120.09(16) . . ?
C22 C23 C24 124.51(16) . . ?
C1 C24 C8 60.35(11) . . ?
C23 C24 C1 116.59(14) . . ?
C23 C24 C8 117.63(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.861
_oxdiff_exptl_absorpt_empirical_full_min 0.673
####################################################################### 
# 
# 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_k11012-jjw-a(tpg77)
_database_code_depnum_ccdc_archive 'CCDC 2226532'
loop_
_audit_author_name
_audit_author_address
CCDC
;Kaohsiung Medical University Taiwan
Taiwan
;
_audit_update_record             
;
2022-12-14 deposited with the CCDC.	2023-04-11 downloaded from the CCDC.
;
_audit_creation_date             2021-12-09
_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         'C32 H30 O4'
_chemical_formula_sum            'C32 H30 O4'
_chemical_formula_weight         478.56
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C31 H26 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.1917(2)
_cell_length_b                   13.3905(2)
_cell_length_c                   24.2721(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.782(2)
_cell_angle_gamma                90
_cell_volume                     5064.17(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    37374
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9840
_cell_measurement_theta_min      1.7610
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            54661
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.744
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  41.00   0.50   19.71    --   10.60 -57.00-120.00  240
  2  ω    -17.00 100.00   0.50   19.71    --   10.60  82.00 -30.00  234
  3  ω    -17.00 100.00   0.50   19.71    --   10.60  82.00  30.00  234
  4  ω    -20.00 100.00   0.50   19.71    --   10.60  57.00 -30.00  240
  5  ω    -79.00  36.00   0.50   19.71    --   10.60 -77.00  30.00  230
  6  ω    -17.00 100.00   0.50   19.71    --   10.60  82.00  90.00  234
  7  ω    -79.00  36.00   0.50   19.71    --   10.60 -77.00-120.00  230
  8  ω    -17.00 100.00   0.50   19.71    --   10.60  82.00   0.00  234
  9  ω    -15.00 100.00   0.50   19.71    --   10.60  77.00-150.00  230
 10  ω    -79.00  37.00   0.50   19.71    --   10.60 -78.00 -14.58  232
 11  ω    -79.00 -12.00   0.50   19.71    --   10.60 -57.00 150.00  134
 12  ω    -79.00  41.00   0.50   19.71    --   10.60 -57.00  90.00  240
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0288734000
_diffrn_orient_matrix_UB_12      -0.0409245000
_diffrn_orient_matrix_UB_13      -0.0055466000
_diffrn_orient_matrix_UB_21      -0.0351104000
_diffrn_orient_matrix_UB_22      0.0335787000
_diffrn_orient_matrix_UB_23      -0.0047259000
_diffrn_orient_matrix_UB_31      -0.0016963000
_diffrn_orient_matrix_UB_32      0.0023188000
_diffrn_orient_matrix_UB_33      -0.0294943000
_diffrn_oxdiff_digest_frames     
;
011d7210b4cd1e8a2debd7f42fe4e05f6400025bde8
;
_diffrn_oxdiff_digest_hkl        
;
012da98eb092effc7eda5fdbdf7c1f32705513
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4063
_reflns_number_total             4459
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4459
_refine_ls_number_restraints     1014
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.011
_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)+(0.0445P)²+3.1670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0897
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim O1
\\sim O2 \\sim O3 \\sim O4: within 3.8A with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14),
 C15(H15), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C26(H26), C28(H28)
3.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
;
_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 0.28752(5) 0.29882(6) 0.30669(4) 0.0302(2) Uani 1 1 d . U . . .
O2 O 0.61973(6) 0.56536(6) 0.45110(4) 0.0298(2) Uani 1 1 d . U . . .
O3 O 0.80628(6) 0.52367(7) 0.33310(4) 0.0364(2) Uani 1 1 d . U . . .
O4 O 0.59843(5) 0.26909(6) 0.34492(4) 0.0274(2) Uani 1 1 d . U . . .
C1 C 0.29385(7) 0.33838(8) 0.35297(5) 0.0238(2) Uani 1 1 d . U . . .
C2 C 0.21647(7) 0.38352(9) 0.36561(5) 0.0258(3) Uani 1 1 d . U . . .
C3 C 0.22072(9) 0.45606(11) 0.40709(6) 0.0410(3) Uani 1 1 d . U . . .
H3 H 0.275018 0.476547 0.430699 0.049 Uiso 1 1 calc R . . . .
C4 C 0.14655(10) 0.49896(13) 0.41445(7) 0.0512(4) Uani 1 1 d . U . . .
H4 H 0.150297 0.549921 0.442254 0.061 Uiso 1 1 calc R . . . .
C5 C 0.06740(9) 0.46785(12) 0.38152(7) 0.0446(4) Uani 1 1 d . U . . .
H5 H 0.016567 0.496860 0.386828 0.054 Uiso 1 1 calc R . . . .
C6 C 0.06213(8) 0.39467(12) 0.34092(6) 0.0424(3) Uani 1 1 d . U . . .
H6 H 0.007555 0.372540 0.318551 0.051 Uiso 1 1 calc R . . . .
C7 C 0.13599(8) 0.35321(10) 0.33256(6) 0.0332(3) Uani 1 1 d . U . . .
H7 H 0.131775 0.303545 0.303980 0.040 Uiso 1 1 calc R . . . .
C8 C 0.38013(7) 0.33792(8) 0.39810(5) 0.0225(2) Uani 1 1 d . U . . .
H8 H 0.375891 0.378311 0.431882 0.027 Uiso 1 1 calc R . . . .
C9 C 0.45101(7) 0.38127(8) 0.37392(5) 0.0216(2) Uani 1 1 d . U . . .
H9 H 0.458238 0.335903 0.342835 0.026 Uiso 1 1 calc R . . . .
C10 C 0.53668(7) 0.38350(8) 0.42160(5) 0.0215(2) Uani 1 1 d . U . . .
H10 H 0.530166 0.437539 0.448547 0.026 Uiso 1 1 calc R . . . .
C11 C 0.55503(7) 0.28844(8) 0.45738(5) 0.0215(2) Uani 1 1 d . U . . .
C12 C 0.63596(7) 0.27418(9) 0.49514(5) 0.0251(3) Uani 1 1 d . U . . .
H12 H 0.680091 0.321301 0.495837 0.030 Uiso 1 1 calc R . . . .
C13 C 0.65348(8) 0.19290(10) 0.53165(5) 0.0284(3) Uani 1 1 d . U . . .
H13 H 0.709397 0.184024 0.556603 0.034 Uiso 1 1 calc R . . . .
C14 C 0.58938(8) 0.12448(9) 0.53178(5) 0.0289(3) Uani 1 1 d . U . . .
H14 H 0.600649 0.069085 0.557182 0.035 Uiso 1 1 calc R . . . .
C15 C 0.50878(8) 0.13782(9) 0.49447(5) 0.0269(3) Uani 1 1 d . U . . .
H15 H 0.464735 0.090954 0.494478 0.032 Uiso 1 1 calc R . . . .
C16 C 0.49080(7) 0.21859(8) 0.45685(5) 0.0231(2) Uani 1 1 d . U . . .
C17 C 0.40206(7) 0.22951(9) 0.41665(5) 0.0264(3) Uani 1 1 d . U . . .
H17A H 0.359446 0.204206 0.435757 0.032 Uiso 1 1 calc R . . . .
H17B H 0.397834 0.188016 0.382238 0.032 Uiso 1 1 calc R . . . .
C18 C 0.42828(7) 0.48427(8) 0.34851(5) 0.0227(2) Uani 1 1 d . U . . .
C19 C 0.41346(8) 0.56399(9) 0.38126(5) 0.0310(3) Uani 1 1 d . U . . .
H19 H 0.419646 0.554670 0.420979 0.037 Uiso 1 1 calc R . . . .
C20 C 0.38980(9) 0.65680(10) 0.35686(6) 0.0391(3) Uani 1 1 d . U . . .
H20 H 0.380016 0.710532 0.379861 0.047 Uiso 1 1 calc R . . . .
C21 C 0.38044(10) 0.67133(10) 0.29930(6) 0.0411(3) Uani 1 1 d . U . . .
H21 H 0.362768 0.734491 0.282342 0.049 Uiso 1 1 calc R . . . .
C22 C 0.39682(10) 0.59383(10) 0.26640(6) 0.0413(3) Uani 1 1 d . U . . .
H22 H 0.391945 0.603966 0.226903 0.050 Uiso 1 1 calc R . . . .
C23 C 0.42038(8) 0.50121(9) 0.29099(5) 0.0311(3) Uani 1 1 d . U . . .
H23 H 0.431351 0.448170 0.267962 0.037 Uiso 1 1 calc R . . . .
C24 C 0.60992(7) 0.41618(8) 0.39802(5) 0.0218(2) Uani 1 1 d . U . . .
C25 C 0.64935(7) 0.50932(9) 0.41302(5) 0.0248(3) Uani 1 1 d . U . . .
C26 C 0.71456(8) 0.54273(9) 0.39079(5) 0.0289(3) Uani 1 1 d . U . . .
H26 H 0.740829 0.605678 0.402004 0.035 Uiso 1 1 calc R . . . .
C27 C 0.74109(7) 0.48367(9) 0.35215(5) 0.0274(3) Uani 1 1 d . U . . .
C28 C 0.70396(7) 0.39133(9) 0.33531(5) 0.0249(3) Uani 1 1 d . U . . .
H28 H 0.722279 0.351250 0.308550 0.030 Uiso 1 1 calc R . . . .
C29 C 0.63895(7) 0.35899(8) 0.35879(5) 0.0224(2) Uani 1 1 d . U . . .
C30 C 0.63169(12) 0.67016(10) 0.44974(7) 0.0507(4) Uani 1 1 d . U . . .
H30A H 0.594343 0.703548 0.469725 0.076 Uiso 1 1 calc GR . . . .
H30B H 0.617260 0.692919 0.409881 0.076 Uiso 1 1 calc GR . . . .
H30C H 0.691716 0.686434 0.468665 0.076 Uiso 1 1 calc GR . . . .
C31 C 0.82447(9) 0.47911(11) 0.28485(7) 0.0409(3) Uani 1 1 d . U . . .
H31A H 0.772336 0.478286 0.252810 0.061 Uiso 1 1 calc GR . . . .
H31B H 0.844524 0.410526 0.294232 0.061 Uiso 1 1 calc GR . . . .
H31C H 0.869142 0.517642 0.274097 0.061 Uiso 1 1 calc GR . . . .
C32 C 0.62565(9) 0.20577(10) 0.30600(6) 0.0364(3) Uani 1 1 d . U . . .
H32A H 0.618554 0.240694 0.269527 0.055 Uiso 1 1 calc GR . . . .
H32B H 0.590907 0.144760 0.299597 0.055 Uiso 1 1 calc GR . . . .
H32C H 0.686205 0.188309 0.322124 0.055 Uiso 1 1 calc GR . . . .


_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 1.2207(14) . ?
O2 C25 1.3742(14) . ?
O2 C30 1.4182(16) . ?
O3 C27 1.3713(14) . ?
O3 C31 1.4148(16) . ?
O4 C29 1.3684(14) . ?
O4 C32 1.4256(15) . ?
C1 C2 1.4961(16) . ?
C1 C8 1.5229(15) . ?
C2 C3 1.3873(18) . ?
C2 C7 1.3920(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.378(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.376(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.3825(19) . ?
C7 H7 0.9500 . ?
C8 H8 1.0000 . ?
C8 C9 1.5380(15) . ?
C8 C17 1.5326(16) . ?
C9 H9 1.0000 . ?
C9 C10 1.5463(15) . ?
C9 C18 1.5148(16) . ?
C10 H10 1.0000 . ?
C10 C11 1.5238(15) . ?
C10 C24 1.5148(15) . ?
C11 C12 1.3930(16) . ?
C11 C16 1.3963(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.3833(17) . ?
C13 H13 0.9500 . ?
C13 C14 1.3849(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.3828(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.3942(17) . ?
C16 C17 1.5083(16) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.3903(17) . ?
C18 C23 1.3854(17) . ?
C19 H19 0.9500 . ?
C19 C20 1.3851(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.378(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.378(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.3843(19) . ?
C23 H23 0.9500 . ?
C24 C25 1.4034(16) . ?
C24 C29 1.3992(16) . ?
C25 C26 1.3842(17) . ?
C26 H26 0.9500 . ?
C26 C27 1.3815(18) . ?
C27 C28 1.3870(17) . ?
C28 H28 0.9500 . ?
C28 C29 1.3953(16) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 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
C25 O2 C30 116.73(10) . . ?
C27 O3 C31 117.84(10) . . ?
C29 O4 C32 118.18(9) . . ?
O1 C1 C2 119.91(10) . . ?
O1 C1 C8 119.42(10) . . ?
C2 C1 C8 120.64(10) . . ?
C3 C2 C1 123.56(11) . . ?
C3 C2 C7 118.43(11) . . ?
C7 C2 C1 117.97(11) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.67(13) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.13(14) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.84(13) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.23(13) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.66(13) . . ?
C6 C7 H7 119.7 . . ?
C1 C8 H8 109.5 . . ?
C1 C8 C9 110.96(9) . . ?
C1 C8 C17 108.00(9) . . ?
C9 C8 H8 109.5 . . ?
C17 C8 H8 109.5 . . ?
C17 C8 C9 109.40(9) . . ?
C8 C9 H9 108.1 . . ?
C8 C9 C10 109.40(9) . . ?
C10 C9 H9 108.1 . . ?
C18 C9 C8 112.04(9) . . ?
C18 C9 H9 108.1 . . ?
C18 C9 C10 110.88(9) . . ?
C9 C10 H10 105.7 . . ?
C11 C10 C9 113.99(9) . . ?
C11 C10 H10 105.7 . . ?
C24 C10 C9 110.96(9) . . ?
C24 C10 H10 105.7 . . ?
C24 C10 C11 113.91(9) . . ?
C12 C11 C10 119.49(10) . . ?
C12 C11 C16 118.63(11) . . ?
C16 C11 C10 121.67(10) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.45(11) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 119.92(11) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.17(11) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.39(11) . . ?
C16 C15 H15 119.3 . . ?
C11 C16 C17 121.13(10) . . ?
C15 C16 C11 119.43(11) . . ?
C15 C16 C17 119.44(10) . . ?
C8 C17 H17A 109.1 . . ?
C8 C17 H17B 109.1 . . ?
C16 C17 C8 112.69(9) . . ?
C16 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C19 C18 C9 121.79(10) . . ?
C23 C18 C9 120.33(11) . . ?
C23 C18 C19 117.87(11) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.00(12) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.11(13) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.72(12) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 119.91(12) . . ?
C23 C22 H22 120.0 . . ?
C18 C23 H23 119.3 . . ?
C22 C23 C18 121.35(12) . . ?
C22 C23 H23 119.3 . . ?
C25 C24 C10 120.42(10) . . ?
C29 C24 C10 122.79(10) . . ?
C29 C24 C25 116.72(10) . . ?
O2 C25 C24 116.26(10) . . ?
O2 C25 C26 121.90(10) . . ?
C26 C25 C24 121.84(11) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 C25 119.38(11) . . ?
C27 C26 H26 120.3 . . ?
O3 C27 C26 114.54(10) . . ?
O3 C27 C28 124.08(11) . . ?
C26 C27 C28 121.37(11) . . ?
C27 C28 H28 121.0 . . ?
C27 C28 C29 118.09(11) . . ?
C29 C28 H28 121.0 . . ?
O4 C29 C24 114.92(10) . . ?
O4 C29 C28 122.49(10) . . ?
C28 C29 C24 122.59(10) . . ?
O2 C30 H30A 109.5 . . ?
O2 C30 H30B 109.5 . . ?
O2 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O3 C31 H31A 109.5 . . ?
O3 C31 H31B 109.5 . . ?
O3 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O4 C32 H32A 109.5 . . ?
O4 C32 H32B 109.5 . . ?
O4 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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 C1 C2 C3 -158.32(13) . . . . ?
O1 C1 C2 C7 19.49(17) . . . . ?
O1 C1 C8 C9 53.97(14) . . . . ?
O1 C1 C8 C17 -65.94(14) . . . . ?
O2 C25 C26 C27 -179.27(11) . . . . ?
O3 C27 C28 C29 179.00(11) . . . . ?
C1 C2 C3 C4 176.28(14) . . . . ?
C1 C2 C7 C6 -177.83(12) . . . . ?
C1 C8 C9 C10 177.73(9) . . . . ?
C1 C8 C9 C18 54.35(12) . . . . ?
C1 C8 C17 C16 173.93(9) . . . . ?
C2 C1 C8 C9 -128.21(11) . . . . ?
C2 C1 C8 C17 111.88(11) . . . . ?
C2 C3 C4 C5 1.8(3) . . . . ?
C3 C2 C7 C6 0.1(2) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C5 C6 C7 C2 1.1(2) . . . . ?
C7 C2 C3 C4 -1.5(2) . . . . ?
C8 C1 C2 C3 23.87(18) . . . . ?
C8 C1 C2 C7 -158.32(11) . . . . ?
C8 C9 C10 C11 44.20(12) . . . . ?
C8 C9 C10 C24 174.41(9) . . . . ?
C8 C9 C18 C19 60.42(14) . . . . ?
C8 C9 C18 C23 -118.59(12) . . . . ?
C9 C8 C17 C16 53.05(13) . . . . ?
C9 C10 C11 C12 169.33(10) . . . . ?
C9 C10 C11 C16 -15.97(15) . . . . ?
C9 C10 C24 C25 110.53(11) . . . . ?
C9 C10 C24 C29 -66.37(13) . . . . ?
C9 C18 C19 C20 -177.72(11) . . . . ?
C9 C18 C23 C22 177.78(12) . . . . ?
C10 C9 C18 C19 -62.13(14) . . . . ?
C10 C9 C18 C23 118.87(11) . . . . ?
C10 C11 C12 C13 174.88(10) . . . . ?
C10 C11 C16 C15 -173.75(10) . . . . ?
C10 C11 C16 C17 5.69(17) . . . . ?
C10 C24 C25 O2 2.24(15) . . . . ?
C10 C24 C25 C26 -177.91(11) . . . . ?
C10 C24 C29 O4 -2.48(15) . . . . ?
C10 C24 C29 C28 177.18(10) . . . . ?
C11 C10 C24 C25 -119.23(11) . . . . ?
C11 C10 C24 C29 63.88(14) . . . . ?
C11 C12 C13 C14 -1.07(18) . . . . ?
C11 C16 C17 C8 -24.48(16) . . . . ?
C12 C11 C16 C15 0.99(17) . . . . ?
C12 C11 C16 C17 -179.57(11) . . . . ?
C12 C13 C14 C15 1.06(18) . . . . ?
C13 C14 C15 C16 -0.03(18) . . . . ?
C14 C15 C16 C11 -1.00(18) . . . . ?
C14 C15 C16 C17 179.55(11) . . . . ?
C15 C16 C17 C8 154.96(11) . . . . ?
C16 C11 C12 C13 0.03(17) . . . . ?
C17 C8 C9 C10 -63.21(11) . . . . ?
C17 C8 C9 C18 173.42(9) . . . . ?
C18 C9 C10 C11 168.26(9) . . . . ?
C18 C9 C10 C24 -61.53(12) . . . . ?
C18 C19 C20 C21 0.1(2) . . . . ?
C19 C18 C23 C22 -1.27(18) . . . . ?
C19 C20 C21 C22 -1.6(2) . . . . ?
C20 C21 C22 C23 1.7(2) . . . . ?
C21 C22 C23 C18 -0.2(2) . . . . ?
C23 C18 C19 C20 1.32(18) . . . . ?
C24 C10 C11 C12 40.60(14) . . . . ?
C24 C10 C11 C16 -144.70(11) . . . . ?
C24 C25 C26 C27 0.89(18) . . . . ?
C25 C24 C29 O4 -179.49(9) . . . . ?
C25 C24 C29 C28 0.18(16) . . . . ?
C25 C26 C27 O3 -179.68(11) . . . . ?
C25 C26 C27 C28 -0.26(18) . . . . ?
C26 C27 C28 C29 -0.36(17) . . . . ?
C27 C28 C29 O4 -179.96(10) . . . . ?
C27 C28 C29 C24 0.40(17) . . . . ?
C29 C24 C25 O2 179.32(10) . . . . ?
C29 C24 C25 C26 -0.83(17) . . . . ?
C30 O2 C25 C24 -155.65(12) . . . . ?
C30 O2 C25 C26 24.50(17) . . . . ?
C31 O3 C27 C26 -166.60(12) . . . . ?
C31 O3 C27 C28 13.99(18) . . . . ?
C32 O4 C29 C24 -178.83(10) . . . . ?
C32 O4 C29 C28 1.51(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.562
_oxdiff_exptl_absorpt_empirical_full_min 0.516
####################################################################### 
# 
# 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_k11102-jjw-e
_database_code_depnum_ccdc_archive 'CCDC 2226531'
loop_
_audit_author_name
_audit_author_address
CCDC
;Kaohsiung Medical University Taiwan
Taiwan
;
_audit_update_record             
;
2022-12-14 deposited with the CCDC.	2023-04-11 downloaded from the CCDC.
;
_audit_creation_date             2022-03-01
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H21 N O'
_chemical_formula_sum            'C24 H21 N O'
_chemical_formula_weight         339.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H20 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   7.5385(2)
_cell_length_b                   12.8334(3)
_cell_length_c                   18.9919(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.438(2)
_cell_angle_gamma                90
_cell_volume                     1817.47(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12634
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.6700
_cell_measurement_theta_min      1.9190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27316
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.922
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00 100.00   0.50   12.39    --   10.60  19.00  90.00  358
  2  ω    -15.00 100.00   0.50   12.39    --   10.60  77.00 150.00  230
  3  ω    -15.00 100.00   0.50   12.39    --   10.60  77.00-120.00  230
  4  ω    -38.00  79.00   0.50   12.39    --  -10.90  82.00-150.00  234
  5  ω   -100.00  27.00   0.50   12.39    --  -10.90 -38.00 -90.00  254
  6  ω    -79.00  41.00   0.50   12.39    --   10.60 -57.00  60.00  240
  7  ω    -79.00   3.00   0.50   12.39    --   10.60 -82.00 -60.00  164
  8  ω    -79.00  41.00   0.50   12.39    --   10.60 -57.00 -30.00  240
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0620240000
_diffrn_orient_matrix_UB_12      0.0395196000
_diffrn_orient_matrix_UB_13      -0.0057853000
_diffrn_orient_matrix_UB_21      0.0358588000
_diffrn_orient_matrix_UB_22      -0.0009759000
_diffrn_orient_matrix_UB_23      0.0366861000
_diffrn_orient_matrix_UB_31      0.0625565000
_diffrn_orient_matrix_UB_32      -0.0386182000
_diffrn_orient_matrix_UB_33      -0.0068480000
_diffrn_oxdiff_digest_frames     
;
01e8a69df20e635989a5ff55b2860eb29b00025f2dd
;
_diffrn_oxdiff_digest_hkl        
;
01410a02ba765701aa4b14ba712bf0056cbd8f
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2621
_reflns_number_total             3202
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.077
_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)+(0.0541P)²+0.5352P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1124
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
O1 \\sim N1: within 3.8A with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21),
 C22(H22), C23(H23), C24(H24)
;
_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 0.45948(13) 0.77617(8) 0.70436(5) 0.0305(3) Uani 1 1 d . U . . .
N1 N 0.2783(2) 0.51354(12) 0.85687(8) 0.0442(4) Uani 1 1 d . U . . .
C1 C 0.3035(2) 0.73924(12) 0.65338(8) 0.0280(4) Uani 1 1 d . . . . .
C2 C 0.21847(19) 0.65038(12) 0.69172(8) 0.0273(4) Uani 1 1 d . . . . .
H2 H 0.220629 0.584635 0.665612 0.033 Uiso 1 1 calc R . . . .
C3 C 0.02178(19) 0.68430(12) 0.69701(8) 0.0279(4) Uani 1 1 d . . . . .
H3 H 0.008747 0.691218 0.747382 0.033 Uiso 1 1 calc R . . . .
C4 C 0.0115(2) 0.79129(12) 0.66375(8) 0.0316(4) Uani 1 1 d . . . . .
H4 H -0.091975 0.831742 0.658491 0.038 Uiso 1 1 calc R . . . .
C5 C 0.1628(2) 0.82259(12) 0.64267(8) 0.0296(4) Uani 1 1 d . . . . .
C6 C 0.2069(2) 0.92080(13) 0.60616(9) 0.0375(4) Uani 1 1 d . . . . .
H6A H 0.295077 0.960513 0.637554 0.045 Uiso 1 1 calc R . . . .
H6B H 0.099774 0.963116 0.595214 0.045 Uiso 1 1 calc R . . . .
C7 C 0.2812(2) 0.89469(14) 0.53725(9) 0.0417(4) Uani 1 1 d . . . . .
H7A H 0.184981 0.867989 0.502380 0.050 Uiso 1 1 calc R . . . .
H7B H 0.326397 0.957809 0.518112 0.050 Uiso 1 1 calc R . . . .
C8 C 0.4317(2) 0.81402(15) 0.54966(9) 0.0406(4) Uani 1 1 d . . . . .
H8A H 0.468847 0.796294 0.504364 0.049 Uiso 1 1 calc R . . . .
H8B H 0.533952 0.844364 0.579608 0.049 Uiso 1 1 calc R . . . .
C9 C 0.3755(2) 0.71481(13) 0.58475(8) 0.0337(4) Uani 1 1 d . . . . .
H9A H 0.283803 0.679264 0.552284 0.040 Uiso 1 1 calc R . . . .
H9B H 0.477857 0.668576 0.594790 0.040 Uiso 1 1 calc R . . . .
C10 C 0.3411(2) 0.64555(12) 0.76205(8) 0.0278(3) Uani 1 1 d . . . . .
C11 C 0.4714(2) 0.71827(12) 0.76434(8) 0.0269(3) Uani 1 1 d . . . . .
C12 C 0.62553(19) 0.74419(12) 0.81846(8) 0.0267(3) Uani 1 1 d . . . . .
C13 C 0.7435(2) 0.82234(12) 0.80358(8) 0.0291(4) Uani 1 1 d . . . . .
H13 H 0.720484 0.859334 0.761111 0.035 Uiso 1 1 calc R . . . .
C14 C 0.8949(2) 0.84490(13) 0.85201(8) 0.0337(4) Uani 1 1 d . . . . .
H14 H 0.973370 0.896833 0.841872 0.040 Uiso 1 1 calc R . . . .
C15 C 0.9292(2) 0.79053(13) 0.91509(9) 0.0361(4) Uani 1 1 d . . . . .
H15 H 1.031844 0.805044 0.947090 0.043 Uiso 1 1 calc R . . . .
C16 C 0.8112(2) 0.71435(13) 0.93095(9) 0.0369(4) Uani 1 1 d . . . . .
H16 H 0.833737 0.678689 0.973967 0.044 Uiso 1 1 calc R . . . .
C17 C 0.6598(2) 0.69108(13) 0.88294(8) 0.0316(4) Uani 1 1 d . . . . .
H17 H 0.580802 0.639879 0.893804 0.038 Uiso 1 1 calc R . . . .
C18 C 0.3114(2) 0.57372(13) 0.81570(8) 0.0319(4) Uani 1 1 d . . . . .
C19 C -0.11717(19) 0.60735(12) 0.66241(8) 0.0279(3) Uani 1 1 d . . . . .
C20 C -0.2157(2) 0.54751(13) 0.70407(9) 0.0335(4) Uani 1 1 d . . . . .
H20 H -0.200540 0.557577 0.753078 0.040 Uiso 1 1 calc R . . . .
C21 C -0.3362(2) 0.47295(14) 0.67318(10) 0.0409(4) Uani 1 1 d . . . . .
H21 H -0.401638 0.433713 0.701551 0.049 Uiso 1 1 calc R . . . .
C22 C -0.3594(2) 0.45689(14) 0.60063(10) 0.0436(5) Uani 1 1 d . . . . .
H22 H -0.439077 0.406352 0.580104 0.052 Uiso 1 1 calc R . . . .
C23 C -0.2633(2) 0.51643(13) 0.55842(9) 0.0399(4) Uani 1 1 d . . . . .
H23 H -0.279087 0.506170 0.509419 0.048 Uiso 1 1 calc R . . . .
C24 C -0.1434(2) 0.59145(13) 0.58925(8) 0.0333(4) Uani 1 1 d . . . . .
H24 H -0.079919 0.631459 0.560595 0.040 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 1.4867(17) . ?
O1 C11 1.3520(18) . ?
N1 C18 1.152(2) . ?
C1 C2 1.542(2) . ?
C1 C5 1.499(2) . ?
C1 C9 1.516(2) . ?
C2 H2 0.9800 . ?
C2 C3 1.563(2) . ?
C2 C10 1.510(2) . ?
C3 H3 0.9800 . ?
C3 C4 1.509(2) . ?
C3 C19 1.517(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.326(2) . ?
C5 C6 1.499(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.534(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.528(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.526(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.351(2) . ?
C10 C18 1.416(2) . ?
C11 C12 1.472(2) . ?
C12 C13 1.396(2) . ?
C12 C17 1.392(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(2) . ?
C17 H17 0.9300 . ?
C19 C20 1.393(2) . ?
C19 C24 1.389(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.389(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.379(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.386(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.390(2) . ?
C24 H24 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
C11 O1 C1 108.79(11) . . ?
O1 C1 C2 105.78(11) . . ?
O1 C1 C5 109.70(12) . . ?
O1 C1 C9 106.09(12) . . ?
C5 C1 C2 104.88(12) . . ?
C5 C1 C9 111.49(13) . . ?
C9 C1 C2 118.61(13) . . ?
C1 C2 H2 111.0 . . ?
C1 C2 C3 106.76(12) . . ?
C3 C2 H2 111.0 . . ?
C10 C2 C1 101.84(12) . . ?
C10 C2 H2 111.0 . . ?
C10 C2 C3 114.71(12) . . ?
C2 C3 H3 108.7 . . ?
C4 C3 C2 102.57(12) . . ?
C4 C3 H3 108.7 . . ?
C4 C3 C19 114.91(12) . . ?
C19 C3 C2 113.09(12) . . ?
C19 C3 H3 108.7 . . ?
C3 C4 H4 122.9 . . ?
C5 C4 C3 114.11(14) . . ?
C5 C4 H4 122.9 . . ?
C1 C5 C6 117.53(14) . . ?
C4 C5 C1 111.47(14) . . ?
C4 C5 C6 130.80(15) . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C5 C6 C7 110.14(14) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 C6 111.84(14) . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C7 112.65(14) . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C1 C9 C8 111.12(14) . . ?
C1 C9 H9A 109.4 . . ?
C1 C9 H9B 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C2 110.36(13) . . ?
C11 C10 C18 128.11(14) . . ?
C18 C10 C2 121.51(13) . . ?
O1 C11 C12 114.35(13) . . ?
C10 C11 O1 113.22(13) . . ?
C10 C11 C12 132.40(14) . . ?
C13 C12 C11 118.80(13) . . ?
C17 C12 C11 121.94(14) . . ?
C17 C12 C13 119.22(14) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.13(15) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.14(15) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.15(15) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.18(15) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 H17 119.9 . . ?
C16 C17 C12 120.14(15) . . ?
C16 C17 H17 119.9 . . ?
N1 C18 C10 176.01(16) . . ?
C20 C19 C3 120.31(14) . . ?
C24 C19 C3 121.09(14) . . ?
C24 C19 C20 118.54(15) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.69(16) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.26(17) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.70(16) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.06(16) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 C23 120.75(16) . . ?
C19 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 119.81(12) . . . . ?
O1 C1 C2 C10 -0.80(14) . . . . ?
O1 C1 C5 C4 -117.90(14) . . . . ?
O1 C1 C5 C6 66.69(16) . . . . ?
O1 C1 C9 C8 -68.73(16) . . . . ?
O1 C11 C12 C13 -0.86(19) . . . . ?
O1 C11 C12 C17 -178.94(13) . . . . ?
C1 O1 C11 C10 -0.69(17) . . . . ?
C1 O1 C11 C12 177.67(12) . . . . ?
C1 C2 C3 C4 -1.94(14) . . . . ?
C1 C2 C3 C19 122.41(13) . . . . ?
C1 C2 C10 C11 0.44(16) . . . . ?
C1 C2 C10 C18 179.29(14) . . . . ?
C1 C5 C6 C7 49.66(18) . . . . ?
C2 C1 C5 C4 -4.69(17) . . . . ?
C2 C1 C5 C6 179.90(12) . . . . ?
C2 C1 C9 C8 172.59(13) . . . . ?
C2 C3 C4 C5 -1.00(17) . . . . ?
C2 C3 C19 C20 110.26(16) . . . . ?
C2 C3 C19 C24 -66.77(18) . . . . ?
C2 C10 C11 O1 0.14(18) . . . . ?
C2 C10 C11 C12 -177.84(15) . . . . ?
C3 C2 C10 C11 -114.45(15) . . . . ?
C3 C2 C10 C18 64.40(19) . . . . ?
C3 C4 C5 C1 3.68(19) . . . . ?
C3 C4 C5 C6 178.30(15) . . . . ?
C3 C19 C20 C21 -176.55(14) . . . . ?
C3 C19 C24 C23 176.16(14) . . . . ?
C4 C3 C19 C20 -132.42(15) . . . . ?
C4 C3 C19 C24 50.5(2) . . . . ?
C4 C5 C6 C7 -124.69(18) . . . . ?
C5 C1 C2 C3 3.87(15) . . . . ?
C5 C1 C2 C10 -116.74(12) . . . . ?
C5 C1 C9 C8 50.65(17) . . . . ?
C5 C6 C7 C8 -50.10(19) . . . . ?
C6 C7 C8 C9 54.84(19) . . . . ?
C7 C8 C9 C1 -54.70(18) . . . . ?
C9 C1 C2 C3 -121.35(14) . . . . ?
C9 C1 C2 C10 118.04(14) . . . . ?
C9 C1 C5 C4 124.88(15) . . . . ?
C9 C1 C5 C6 -50.53(18) . . . . ?
C10 C2 C3 C4 110.05(14) . . . . ?
C10 C2 C3 C19 -125.60(14) . . . . ?
C10 C11 C12 C13 177.10(16) . . . . ?
C10 C11 C12 C17 -1.0(3) . . . . ?
C11 O1 C1 C2 0.93(15) . . . . ?
C11 O1 C1 C5 113.55(13) . . . . ?
C11 O1 C1 C9 -125.90(13) . . . . ?
C11 C12 C13 C14 -176.74(14) . . . . ?
C11 C12 C17 C16 176.76(14) . . . . ?
C12 C13 C14 C15 -0.2(2) . . . . ?
C13 C12 C17 C16 -1.3(2) . . . . ?
C13 C14 C15 C16 -1.1(2) . . . . ?
C14 C15 C16 C17 1.2(3) . . . . ?
C15 C16 C17 C12 0.0(2) . . . . ?
C17 C12 C13 C14 1.4(2) . . . . ?
C18 C10 C11 O1 -178.61(14) . . . . ?
C18 C10 C11 C12 3.4(3) . . . . ?
C19 C3 C4 C5 -124.13(15) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C20 C19 C24 C23 -0.9(2) . . . . ?
C20 C21 C22 C23 -0.8(3) . . . . ?
C21 C22 C23 C24 0.4(2) . . . . ?
C22 C23 C24 C19 0.4(2) . . . . ?
C24 C19 C20 C21 0.6(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 1.556
_oxdiff_exptl_absorpt_empirical_full_min 0.621
####################################################################### 
# 
# 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_k11008-jjw-o(nc-en-18)
_database_code_depnum_ccdc_archive 'CCDC 2226530'
loop_
_audit_author_name
_audit_author_address
CCDC
;Kaohsiung Medical University Taiwan
Taiwan
;
_audit_update_record             
;
2022-12-14 deposited with the CCDC.	2023-04-11 downloaded from the CCDC.
;
_audit_creation_date             2021-08-26
_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         'C23 H18 O'
_chemical_formula_sum            'C23 H18 O'
_chemical_formula_weight         310.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H18 N1 O1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   16.1546(3)
_cell_length_b                   5.92860(10)
_cell_length_c                   16.4487(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.338(2)
_cell_angle_gamma                90
_cell_volume                     1570.85(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16828
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9240
_cell_measurement_theta_min      2.4720
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27269
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.484
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  38.00   0.50   11.03    --   10.60 -82.00 -94.00  234
  2  ω    -17.00 100.00   0.50   11.03    --   10.60  82.00  27.00  234
  3  ω    -38.00  78.00   0.50   11.03    --  -10.90  82.00  27.00  232
  4  ω   -100.00  16.00   0.50   11.03    --  -10.90 -82.00 -94.00  232
  5  ω    -79.00  48.00   0.50   11.03    --   10.60 -38.00 -60.00  254
  6  ω    -79.00  41.00   0.50   11.03    --   10.60 -57.00  60.00  240
  7  ω    -79.00  38.00   0.50   11.03    --   10.60 -82.00-180.00  234
  8  ω    -15.00 100.00   0.50   11.03    --   10.60  77.00 -90.00  230
  9  ω    -15.00  72.00   0.50   11.03    --   10.60  77.00-180.00  174
 10  ω    -15.00 100.00   0.50   11.03    --   10.60  77.00 150.00  230
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0212841000
_diffrn_orient_matrix_UB_12      -0.0514697000
_diffrn_orient_matrix_UB_13      0.0312936000
_diffrn_orient_matrix_UB_21      -0.0385637000
_diffrn_orient_matrix_UB_22      0.0295785000
_diffrn_orient_matrix_UB_23      -0.0206831000
_diffrn_orient_matrix_UB_31      -0.0004451000
_diffrn_orient_matrix_UB_32      -0.1039763000
_diffrn_orient_matrix_UB_33      -0.0214124000
_diffrn_oxdiff_digest_frames     
;
01877b3f76c6044d93a986a1ba4eb9c474000255359
;
_diffrn_oxdiff_digest_hkl        
;
018b73adcdf211fece8f96464f5a9d99a74b0c
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2497
_reflns_number_total             2759
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2759
_refine_ls_number_restraints     684
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      0.990
_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)+(0.0468P)²+0.4433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0929
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim O1: within
3.8A with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1), C8(H8), C17(H17)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   mixed
_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 0.19984(5) 0.18139(14) 0.26571(5) 0.0191(2) Uani 1 1 d . U . . .
C1 C 0.27977(7) 0.1586(2) 0.31194(7) 0.0186(3) Uani 1 1 d . U . . .
H1 H 0.303461 0.003912 0.306617 0.022 Uiso 1 1 calc R . . . .
C2 C 0.26559(6) 0.2136(2) 0.39869(7) 0.0179(3) Uani 1 1 d . U . . .
C3 C 0.27876(7) 0.0685(2) 0.46441(7) 0.0206(3) Uani 1 1 d . U . . .
H3 H 0.304574 -0.073651 0.457834 0.025 Uiso 1 1 calc R . . . .
C4 C 0.25389(7) 0.1327(2) 0.53993(7) 0.0231(3) Uani 1 1 d . U . . .
H4 H 0.262380 0.033887 0.585258 0.028 Uiso 1 1 calc R . . . .
C5 C 0.21657(7) 0.3414(2) 0.54939(7) 0.0221(3) Uani 1 1 d . U . . .
H5 H 0.199192 0.383661 0.601156 0.026 Uiso 1 1 calc R . . . .
C6 C 0.20445(7) 0.4885(2) 0.48411(7) 0.0196(3) Uani 1 1 d . U . . .
H6 H 0.179441 0.631532 0.491156 0.023 Uiso 1 1 calc R . . . .
C7 C 0.22917(6) 0.4253(2) 0.40815(7) 0.0171(3) Uani 1 1 d . U . . .
C8 C 0.21355(7) 0.5573(2) 0.33260(7) 0.0173(3) Uani 1 1 d . U . . .
H8 H 0.186183 0.707475 0.337545 0.021 Uiso 1 1 calc R . . . .
C9 C 0.18786(7) 0.4172(2) 0.25565(7) 0.0180(3) Uani 1 1 d . U . . .
C10 C 0.11425(7) 0.4765(2) 0.20047(7) 0.0189(3) Uani 1 1 d . U . . .
C11 C 0.05167(7) 0.3179(2) 0.18395(7) 0.0227(3) Uani 1 1 d . U . . .
H11 H 0.055676 0.173417 0.208912 0.027 Uiso 1 1 calc R . . . .
C12 C -0.01651(7) 0.3708(2) 0.13106(8) 0.0279(3) Uani 1 1 d . U . . .
H12 H -0.058501 0.260919 0.119274 0.034 Uiso 1 1 calc R . . . .
C13 C -0.02414(8) 0.5811(2) 0.09534(8) 0.0282(3) Uani 1 1 d . U . . .
H13 H -0.071059 0.616137 0.059222 0.034 Uiso 1 1 calc R . . . .
C14 C 0.03725(8) 0.7405(2) 0.11265(8) 0.0278(3) Uani 1 1 d . U . . .
H14 H 0.032225 0.886067 0.088636 0.033 Uiso 1 1 calc R . . . .
C15 C 0.10615(7) 0.6888(2) 0.16494(7) 0.0241(3) Uani 1 1 d . U . . .
H15 H 0.148019 0.799165 0.176483 0.029 Uiso 1 1 calc R . . . .
C16 C 0.27126(7) 0.5295(2) 0.26310(7) 0.0176(3) Uani 1 1 d . U . . .
C17 C 0.33368(7) 0.3399(2) 0.27352(7) 0.0184(3) Uani 1 1 d . U . . .
H17 H 0.345759 0.286367 0.217996 0.022 Uiso 1 1 calc R . . . .
C18 C 0.41570(7) 0.3848(2) 0.32136(7) 0.0187(3) Uani 1 1 d . U . . .
C19 C 0.43293(7) 0.5848(2) 0.36289(7) 0.0225(3) Uani 1 1 d . U . . .
H19 H 0.391759 0.699342 0.362402 0.027 Uiso 1 1 calc R . . . .
C20 C 0.50958(8) 0.6203(2) 0.40525(8) 0.0283(3) Uani 1 1 d . U . . .
H20 H 0.520637 0.758819 0.433011 0.034 Uiso 1 1 calc R . . . .
C21 C 0.56975(8) 0.4541(2) 0.40701(8) 0.0309(3) Uani 1 1 d . U . . .
H21 H 0.622083 0.477512 0.436149 0.037 Uiso 1 1 calc R . . . .
C22 C 0.55317(7) 0.2534(3) 0.36604(8) 0.0307(3) Uani 1 1 d . U . . .
H22 H 0.594258 0.138558 0.367282 0.037 Uiso 1 1 calc R . . . .
C23 C 0.47693(7) 0.2187(2) 0.32314(8) 0.0245(3) Uani 1 1 d . U . . .
H23 H 0.466375 0.080839 0.294783 0.029 Uiso 1 1 calc R . . . .
H16 H 0.2827(8) 0.667(2) 0.2317(8) 0.020(3) Uiso 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 C1 1.4543(13) . ?
O1 C9 1.4191(15) . ?
C1 H1 1.0000 . ?
C1 C2 1.4981(16) . ?
C1 C17 1.5481(16) . ?
C2 C3 1.3854(17) . ?
C2 C7 1.4000(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.3874(17) . ?
C4 H4 0.9500 . ?
C4 C5 1.3905(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3857(17) . ?
C6 H6 0.9500 . ?
C6 C7 1.3915(16) . ?
C7 C8 1.4740(16) . ?
C8 H8 1.0000 . ?
C8 C9 1.5445(16) . ?
C8 C16 1.5376(15) . ?
C9 C10 1.4827(16) . ?
C9 C16 1.4996(15) . ?
C10 C11 1.3923(17) . ?
C10 C15 1.3894(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.3870(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.3836(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.3885(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.5112(16) . ?
C16 H16 0.990(14) . ?
C17 H17 1.0000 . ?
C17 C18 1.5126(16) . ?
C18 C19 1.3862(18) . ?
C18 C23 1.3947(17) . ?
C19 H19 0.9500 . ?
C19 C20 1.3901(17) . ?
C20 H20 0.9500 . ?
C20 C21 1.3829(19) . ?
C21 H21 0.9500 . ?
C21 C22 1.384(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.3877(18) . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C1 105.10(8) . . ?
O1 C1 H1 111.7 . . ?
O1 C1 C2 106.51(9) . . ?
O1 C1 C17 103.10(9) . . ?
C2 C1 H1 111.7 . . ?
C2 C1 C17 111.64(10) . . ?
C17 C1 H1 111.7 . . ?
C3 C2 C1 125.63(11) . . ?
C3 C2 C7 120.73(11) . . ?
C7 C2 C1 113.39(10) . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.37(12) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.12(11) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.69(11) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.54(11) . . ?
C7 C6 H6 120.2 . . ?
C2 C7 C8 115.39(10) . . ?
C6 C7 C2 119.53(11) . . ?
C6 C7 C8 124.86(11) . . ?
C7 C8 H8 116.9 . . ?
C7 C8 C9 115.06(10) . . ?
C7 C8 C16 119.68(10) . . ?
C9 C8 H8 116.9 . . ?
C16 C8 H8 116.9 . . ?
C16 C8 C9 58.23(7) . . ?
O1 C9 C8 114.11(9) . . ?
O1 C9 C10 113.65(10) . . ?
O1 C9 C16 108.32(9) . . ?
C10 C9 C8 121.82(10) . . ?
C10 C9 C16 128.22(10) . . ?
C16 C9 C8 60.66(7) . . ?
C11 C10 C9 119.74(11) . . ?
C15 C10 C9 121.20(11) . . ?
C15 C10 C11 119.06(11) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.00(12) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.84(12) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.34(12) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.34(13) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.41(12) . . ?
C14 C15 H15 119.8 . . ?
C8 C16 H16 116.6(7) . . ?
C9 C16 C8 61.12(7) . . ?
C9 C16 C17 105.45(10) . . ?
C9 C16 H16 121.7(7) . . ?
C17 C16 C8 115.61(10) . . ?
C17 C16 H16 121.5(7) . . ?
C1 C17 H17 107.9 . . ?
C16 C17 C1 99.89(9) . . ?
C16 C17 H17 107.9 . . ?
C16 C17 C18 118.60(10) . . ?
C18 C17 C1 114.06(9) . . ?
C18 C17 H17 107.9 . . ?
C19 C18 C17 122.85(10) . . ?
C19 C18 C23 118.56(11) . . ?
C23 C18 C17 118.59(11) . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 120.96(11) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.05(13) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.2 . . ?
C20 C21 C22 119.52(12) . . ?
C22 C21 H21 120.2 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.46(12) . . ?
C23 C22 H22 119.8 . . ?
C18 C23 H23 119.8 . . ?
C22 C23 C18 120.45(12) . . ?
C22 C23 H23 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 119.02(11) . . . . ?
O1 C1 C2 C7 -55.21(12) . . . . ?
O1 C1 C17 C16 40.85(10) . . . . ?
O1 C1 C17 C18 168.44(9) . . . . ?
O1 C9 C10 C11 19.24(15) . . . . ?
O1 C9 C10 C15 -161.02(10) . . . . ?
O1 C9 C16 C8 -107.91(10) . . . . ?
O1 C9 C16 C17 3.17(12) . . . . ?
C1 O1 C9 C8 -41.72(11) . . . . ?
C1 O1 C9 C10 172.52(9) . . . . ?
C1 O1 C9 C16 23.61(11) . . . . ?
C1 C2 C3 C4 -172.51(11) . . . . ?
C1 C2 C7 C6 173.26(10) . . . . ?
C1 C2 C7 C8 -1.60(13) . . . . ?
C1 C17 C18 C19 -110.60(13) . . . . ?
C1 C17 C18 C23 70.01(13) . . . . ?
C2 C1 C17 C16 -73.11(11) . . . . ?
C2 C1 C17 C18 54.48(13) . . . . ?
C2 C3 C4 C5 -0.37(17) . . . . ?
C2 C7 C8 C9 35.53(13) . . . . ?
C2 C7 C8 C16 -30.73(14) . . . . ?
C3 C2 C7 C6 -1.29(16) . . . . ?
C3 C2 C7 C8 -176.15(10) . . . . ?
C3 C4 C5 C6 -0.63(17) . . . . ?
C4 C5 C6 C7 0.67(17) . . . . ?
C5 C6 C7 C2 0.28(16) . . . . ?
C5 C6 C7 C8 174.62(10) . . . . ?
C6 C7 C8 C9 -139.01(11) . . . . ?
C6 C7 C8 C16 154.73(11) . . . . ?
C7 C2 C3 C4 1.33(17) . . . . ?
C7 C8 C9 O1 -12.45(13) . . . . ?
C7 C8 C9 C10 130.20(11) . . . . ?
C7 C8 C9 C16 -110.69(11) . . . . ?
C7 C8 C16 C9 102.73(12) . . . . ?
C7 C8 C16 C17 8.55(15) . . . . ?
C8 C9 C10 C11 -123.56(12) . . . . ?
C8 C9 C10 C15 56.17(15) . . . . ?
C8 C9 C16 C17 111.08(10) . . . . ?
C8 C16 C17 C1 38.56(12) . . . . ?
C8 C16 C17 C18 -85.94(12) . . . . ?
C9 O1 C1 C2 77.10(10) . . . . ?
C9 O1 C1 C17 -40.54(10) . . . . ?
C9 C8 C16 C17 -94.19(11) . . . . ?
C9 C10 C11 C12 -178.65(10) . . . . ?
C9 C10 C15 C14 179.23(11) . . . . ?
C9 C16 C17 C1 -26.40(11) . . . . ?
C9 C16 C17 C18 -150.90(10) . . . . ?
C10 C9 C16 C8 109.10(13) . . . . ?
C10 C9 C16 C17 -139.82(11) . . . . ?
C10 C11 C12 C13 -1.14(18) . . . . ?
C11 C10 C15 C14 -1.04(17) . . . . ?
C11 C12 C13 C14 0.07(19) . . . . ?
C12 C13 C14 C15 0.51(19) . . . . ?
C13 C14 C15 C10 -0.02(19) . . . . ?
C15 C10 C11 C12 1.61(17) . . . . ?
C16 C8 C9 O1 98.24(10) . . . . ?
C16 C8 C9 C10 -119.10(12) . . . . ?
C16 C9 C10 C11 160.64(11) . . . . ?
C16 C9 C10 C15 -19.62(18) . . . . ?
C16 C17 C18 C19 6.63(16) . . . . ?
C16 C17 C18 C23 -172.75(10) . . . . ?
C17 C1 C2 C3 -129.15(12) . . . . ?
C17 C1 C2 C7 56.62(12) . . . . ?
C17 C18 C19 C20 -179.15(11) . . . . ?
C17 C18 C23 C22 179.76(11) . . . . ?
C18 C19 C20 C21 -0.58(18) . . . . ?
C19 C18 C23 C22 0.35(17) . . . . ?
C19 C20 C21 C22 0.33(19) . . . . ?
C20 C21 C22 C23 0.25(19) . . . . ?
C21 C22 C23 C18 -0.59(19) . . . . ?
C23 C18 C19 C20 0.23(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.916
_oxdiff_exptl_absorpt_empirical_full_min 0.479
