# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_20190363
_database_code_depnum_ccdc_archive 'CCDC 2502854'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2025-11-14 deposited with the CCDC.	2026-02-02 downloaded from the CCDC.
;
_audit_creation_date             2019-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 O4'
_chemical_formula_sum            'C21 H16 O4'
_chemical_formula_weight         332.34
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4F3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.8673(6)
_cell_length_b                   11.3115(6)
_cell_length_c                   13.3163(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1636.92(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2334
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9220
_cell_measurement_theta_min      5.1160
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.863
_exptl_absorpt_coefficient_mu    0.761
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 1.001
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6198
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         5.130
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.001
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -73.00  -40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
  2 omega    6.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -44.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
  4 omega   -1.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000 -180.0000 66

#__ type_ start__ end____ width___ exp.time_
  5 omega   73.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000 -180.0000 35

#__ type_ start__ end____ width___ exp.time_
  6 omega   63.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 47

#__ type_ start__ end____ width___ exp.time_
  7 omega   41.00   75.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
  8 omega   42.00  100.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 58

#__ type_ start__ end____ width___ exp.time_
  9 omega   63.00  147.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
 10 omega  125.00  166.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 41

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   77.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 39

#__ type_ start__ end____ width___ exp.time_
 12 omega   45.00   71.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   73.00   99.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega  -87.00  -52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   30.0000 35

#__ type_ start__ end____ width___ exp.time_
 15 omega   61.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   32.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 17 omega  -34.00   -6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000  120.0000 28

#__ type_ start__ end____ width___ exp.time_
 18 omega   40.00   69.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 29

#__ type_ start__ end____ width___ exp.time_
 19 omega   53.00  104.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 51

#__ type_ start__ end____ width___ exp.time_
 20 omega   45.00   76.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 31

#__ type_ start__ end____ width___ exp.time_
 21 omega   56.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 35

#__ type_ start__ end____ width___ exp.time_
 22 omega   74.00   99.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 23 omega  137.00  163.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega   57.00   83.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000   30.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0454049000
_diffrn_orient_matrix_UB_12      0.0279111000
_diffrn_orient_matrix_UB_13      0.1069556000
_diffrn_orient_matrix_UB_21      0.0128010000
_diffrn_orient_matrix_UB_22      0.1314669000
_diffrn_orient_matrix_UB_23      -0.0283069000
_diffrn_orient_matrix_UB_31      -0.1337004000
_diffrn_orient_matrix_UB_32      0.0221124000
_diffrn_orient_matrix_UB_33      0.0337359000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2508
_reflns_number_total             2921
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 905 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_coef       0.0066(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2921
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.046
_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)+(0.0619P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1158
_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.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8476(3) 0.4637(3) 0.3040(3) 0.0528(7) Uani 1 1 d . . . . .
C2 C 0.8229(3) 0.5552(3) 0.3754(3) 0.0479(7) Uani 1 1 d . . . . .
C3 C 0.8776(3) 0.6622(2) 0.3636(2) 0.0452(6) Uani 1 1 d . . . . .
C4 C 0.9537(3) 0.6873(3) 0.2794(3) 0.0503(7) Uani 1 1 d . . . . .
H4 H 0.9913 0.7607 0.2724 0.060 Uiso 1 1 calc R . . . .
C5 C 0.9697(3) 0.6030(3) 0.2107(3) 0.0548(8) Uani 1 1 d . . . . .
C6 C 1.0408(4) 0.6135(4) 0.1158(3) 0.0730(10) Uani 1 1 d . . . . .
H6A H 1.0901 0.5439 0.1066 0.110 Uiso 1 1 calc GR . . . .
H6B H 1.0933 0.6816 0.1192 0.110 Uiso 1 1 calc GR . . . .
H6C H 0.9850 0.6218 0.0604 0.110 Uiso 1 1 calc GR . . . .
C7 C 0.8706(3) 0.5652(3) 0.6126(3) 0.0557(8) Uani 1 1 d . . . . .
C8 C 0.9349(3) 0.5294(4) 0.6970(3) 0.0668(9) Uani 1 1 d . . . . .
H8 H 0.9731 0.5848 0.7382 0.080 Uiso 1 1 calc R . . . .
C9 C 0.9415(4) 0.4094(5) 0.7193(4) 0.0822(13) Uani 1 1 d . . . . .
H9 H 0.9854 0.3843 0.7753 0.099 Uiso 1 1 calc R . . . .
C10 C 0.8839(4) 0.3280(4) 0.6592(4) 0.0814(13) Uani 1 1 d . . . . .
H10 H 0.8886 0.2480 0.6748 0.098 Uiso 1 1 calc R . . . .
C11 C 0.8190(3) 0.3646(4) 0.5757(3) 0.0677(10) Uani 1 1 d . . . . .
H11 H 0.7802 0.3089 0.5352 0.081 Uiso 1 1 calc R . . . .
C12 C 0.8113(3) 0.4835(3) 0.5516(3) 0.0555(8) Uani 1 1 d . . . . .
C13 C 0.7396(3) 0.5313(3) 0.4628(3) 0.0514(7) Uani 1 1 d . . . . .
H13 H 0.6745 0.4758 0.4435 0.062 Uiso 1 1 calc R . . . .
C14 C 0.6836(3) 0.6494(3) 0.4958(2) 0.0502(7) Uani 1 1 d . . . . .
H14A H 0.6330 0.6819 0.4425 0.060 Uiso 1 1 calc R . . . .
H14B H 0.6326 0.6384 0.5548 0.060 Uiso 1 1 calc R . . . .
C15 C 0.7893(3) 0.7323(3) 0.5192(2) 0.0481(7) Uani 1 1 d . . . . .
C16 C 0.7477(3) 0.8536(3) 0.5518(2) 0.0479(7) Uani 1 1 d . . . . .
C17 C 0.7603(3) 0.8916(3) 0.6498(3) 0.0609(8) Uani 1 1 d . . . . .
H17 H 0.7957 0.8426 0.6979 0.073 Uiso 1 1 calc R . . . .
C18 C 0.7192(4) 1.0045(4) 0.6760(3) 0.0764(12) Uani 1 1 d . . . . .
H18 H 0.7297 1.0313 0.7415 0.092 Uiso 1 1 calc R . . . .
C19 C 0.6635(4) 1.0764(3) 0.6065(3) 0.0703(10) Uani 1 1 d . . . . .
H19 H 0.6366 1.1514 0.6249 0.084 Uiso 1 1 calc R . . . .
C20 C 0.6477(4) 1.0370(3) 0.5100(3) 0.0692(10) Uani 1 1 d . . . . .
H20 H 0.6082 1.0847 0.4630 0.083 Uiso 1 1 calc R . . . .
C21 C 0.6904(3) 0.9270(3) 0.4825(3) 0.0597(8) Uani 1 1 d . . . . .
H21 H 0.6806 0.9014 0.4166 0.072 Uiso 1 1 calc R . . . .
O1 O 0.9186(2) 0.4937(2) 0.22114(19) 0.0583(6) Uani 1 1 d . . . . .
O2 O 0.8115(3) 0.3623(2) 0.3079(2) 0.0685(7) Uani 1 1 d . . . . .
O3 O 0.86312(19) 0.75293(19) 0.42943(17) 0.0524(5) Uani 1 1 d . . . . .
O4 O 0.8694(2) 0.6859(2) 0.59353(19) 0.0590(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.431(4) . ?
C1 O1 1.389(4) . ?
C1 O2 1.213(4) . ?
C2 C3 1.357(4) . ?
C2 C13 1.500(5) . ?
C3 C4 1.422(5) . ?
C3 O3 1.359(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.332(5) . ?
C5 C6 1.486(5) . ?
C5 O1 1.363(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.384(5) . ?
C7 C12 1.388(5) . ?
C7 O4 1.388(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.391(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.370(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(5) . ?
C12 C13 1.516(5) . ?
C13 H13 0.9800 . ?
C13 C14 1.532(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.515(4) . ?
C15 C16 1.508(4) . ?
C15 O3 1.459(4) . ?
C15 O4 1.418(4) . ?
C16 C17 1.381(5) . ?
C16 C21 1.389(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.397(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.373(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.372(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.378(5) . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 117.1(3) . . ?
O2 C1 C2 126.5(3) . . ?
O2 C1 O1 116.4(3) . . ?
C1 C2 C13 119.9(3) . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 C13 121.0(3) . . ?
C2 C3 C4 121.6(3) . . ?
C2 C3 O3 123.3(3) . . ?
O3 C3 C4 115.2(3) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.4(3) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C6 126.5(3) . . ?
C4 C5 O1 121.7(3) . . ?
O1 C5 C6 111.8(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 121.0(3) . . ?
C8 C7 O4 116.1(3) . . ?
C12 C7 O4 122.9(3) . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 119.0(4) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.5(4) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.1(4) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.5(4) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 C13 117.2(3) . . ?
C11 C12 C7 118.9(4) . . ?
C11 C12 C13 123.9(3) . . ?
C2 C13 C12 111.1(2) . . ?
C2 C13 H13 110.3 . . ?
C2 C13 C14 107.7(2) . . ?
C12 C13 H13 110.3 . . ?
C12 C13 C14 107.0(3) . . ?
C14 C13 H13 110.3 . . ?
C13 C14 H14A 110.3 . . ?
C13 C14 H14B 110.3 . . ?
H14A C14 H14B 108.5 . . ?
C15 C14 C13 107.3(2) . . ?
C15 C14 H14A 110.3 . . ?
C15 C14 H14B 110.3 . . ?
C16 C15 C14 113.2(2) . . ?
O3 C15 C14 110.3(3) . . ?
O3 C15 C16 104.8(2) . . ?
O4 C15 C14 112.3(3) . . ?
O4 C15 C16 108.6(3) . . ?
O4 C15 O3 107.1(2) . . ?
C17 C16 C15 121.7(3) . . ?
C17 C16 C21 119.1(3) . . ?
C21 C16 C15 119.1(3) . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.3(4) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 120.9(4) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.7(4) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.0(4) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 H21 119.5 . . ?
C20 C21 C16 121.0(4) . . ?
C20 C21 H21 119.5 . . ?
C5 O1 C1 121.9(3) . . ?
C3 O3 C15 118.1(2) . . ?
C7 O4 C15 119.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 3.3(4) . . . . ?
C1 C2 C3 O3 -177.6(3) . . . . ?
C1 C2 C13 C12 88.9(3) . . . . ?
C1 C2 C13 C14 -154.3(3) . . . . ?
C2 C1 O1 C5 4.2(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C2 C3 O3 C15 2.7(4) . . . . ?
C2 C13 C14 C15 -56.7(3) . . . . ?
C3 C2 C13 C12 -89.8(3) . . . . ?
C3 C2 C13 C14 27.0(4) . . . . ?
C3 C4 C5 C6 177.2(3) . . . . ?
C3 C4 C5 O1 -2.1(5) . . . . ?
C4 C3 O3 C15 -178.1(2) . . . . ?
C4 C5 O1 C1 -0.4(5) . . . . ?
C6 C5 O1 C1 -179.8(3) . . . . ?
C7 C8 C9 C10 -0.8(6) . . . . ?
C7 C12 C13 C2 82.3(4) . . . . ?
C7 C12 C13 C14 -35.0(4) . . . . ?
C8 C7 C12 C11 -1.0(5) . . . . ?
C8 C7 C12 C13 178.0(3) . . . . ?
C8 C7 O4 C15 -169.3(3) . . . . ?
C8 C9 C10 C11 0.3(7) . . . . ?
C9 C10 C11 C12 0.0(6) . . . . ?
C10 C11 C12 C7 0.4(5) . . . . ?
C10 C11 C12 C13 -178.5(3) . . . . ?
C11 C12 C13 C2 -98.7(4) . . . . ?
C11 C12 C13 C14 143.9(3) . . . . ?
C12 C7 C8 C9 1.2(5) . . . . ?
C12 C7 O4 C15 10.6(5) . . . . ?
C12 C13 C14 C15 62.8(3) . . . . ?
C13 C2 C3 C4 -178.0(3) . . . . ?
C13 C2 C3 O3 1.2(4) . . . . ?
C13 C14 C15 C16 179.3(3) . . . . ?
C13 C14 C15 O3 62.3(3) . . . . ?
C13 C14 C15 O4 -57.1(3) . . . . ?
C14 C15 C16 C17 109.0(3) . . . . ?
C14 C15 C16 C21 -68.1(4) . . . . ?
C14 C15 O3 C3 -35.2(3) . . . . ?
C14 C15 O4 C7 20.4(4) . . . . ?
C15 C16 C17 C18 -179.4(3) . . . . ?
C15 C16 C21 C20 178.1(3) . . . . ?
C16 C15 O3 C3 -157.4(2) . . . . ?
C16 C15 O4 C7 146.5(3) . . . . ?
C16 C17 C18 C19 1.9(6) . . . . ?
C17 C16 C21 C20 0.9(5) . . . . ?
C17 C18 C19 C20 0.1(6) . . . . ?
C18 C19 C20 C21 -1.6(6) . . . . ?
C19 C20 C21 C16 1.1(6) . . . . ?
C21 C16 C17 C18 -2.4(5) . . . . ?
O1 C1 C2 C3 -5.5(4) . . . . ?
O1 C1 C2 C13 175.7(3) . . . . ?
O2 C1 C2 C3 175.4(3) . . . . ?
O2 C1 C2 C13 -3.3(5) . . . . ?
O2 C1 O1 C5 -176.7(3) . . . . ?
O3 C3 C4 C5 -178.6(3) . . . . ?
O3 C15 C16 C17 -130.7(3) . . . . ?
O3 C15 C16 C21 52.2(3) . . . . ?
O3 C15 O4 C7 -100.8(3) . . . . ?
O4 C7 C8 C9 -178.8(3) . . . . ?
O4 C7 C12 C11 179.0(3) . . . . ?
O4 C7 C12 C13 -2.0(5) . . . . ?
O4 C15 C16 C17 -16.5(4) . . . . ?
O4 C15 C16 C21 166.4(3) . . . . ?
O4 C15 O3 C3 87.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_zy_168
_database_code_depnum_ccdc_archive 'CCDC 2522871'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2026-01-14 deposited with the CCDC.	2026-02-02 downloaded from the CCDC.
;
_audit_creation_date             2026-01-10
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 Cl O3'
_chemical_formula_sum            'C21 H19 Cl O3'
_chemical_formula_weight         354.81
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N S P Cl'
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'
Cl Cl 0.3639 0.7018 '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        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   11.2354(5)
_cell_length_b                   5.1466(2)
_cell_length_c                   30.3740(12)
_cell_angle_alpha                90
_cell_angle_beta                 97.699(4)
_cell_angle_gamma                90
_cell_volume                     1740.52(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5670
_cell_measurement_temperature    100.08(14)
_cell_measurement_theta_max      72.3190
_cell_measurement_theta_min      4.0620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.129a (Rigaku Oxford Diffraction, 2025)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.15
_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  0.0709
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            8907
_diffrn_reflns_point_group_measured_fraction_full 0.831
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_theta_full        66.601
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_min         4.045
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.08(14)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.979
_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     61.00 103.00   0.50    0.08    --   61.92  15.00-120.00   84
  2  ω     57.00  99.00   0.50    0.08    --   61.92  15.00 -30.00   84
  3  ω     59.00  97.00   0.50    0.08    --   61.92  15.00   0.00   76
  4  ω     54.00  89.00   0.50    0.08    --   61.92  15.00 -60.00   70
  5  ω     62.00  87.00   0.50    0.08    --   61.92  15.00  30.00   50
  6  ω     75.00 100.00   0.50    0.08    --   71.24  15.00   0.00   50
  7  ω     60.00  96.00   0.50    0.08    --   61.92  15.00  60.00   72
  8  ω     75.00 103.00   0.50    0.08    --   74.15  15.00 120.00   56
  9  ω     58.00  86.00   0.50    0.08    --   61.92  15.00 150.00   56
 10  ω     72.00 110.00   0.50    0.08    --   74.15  15.00 150.00   76
 11  ω     59.00  85.00   0.50    0.08    --   61.92  15.00 120.00   52
 12  ω     60.00  96.00   0.50    0.08    --   61.92  15.00  90.00   72
 13  ω     85.00 111.00   0.50    0.08    --   74.15  15.00 -60.00   52
 14  ω     77.00 115.00   0.50    0.08    --   74.15  15.00 -90.00   76
 15  ω     63.00 109.00   0.50    0.08    --   71.24  15.00-120.00   92
 16  ω     80.00 114.00   0.50    0.08    --   74.15  15.00-180.00   68
 17  ω     73.00 107.00   0.50    0.08    --   74.15  15.00  30.00   68
 18  ω     35.00  82.00   0.50    0.08    --   74.15-125.00  90.00   94
 19  ω     24.00  75.00   0.50    0.08    --   61.92-125.00 150.00  102
 20  ω     49.00  80.00   0.50    0.08    --   61.92-125.00   0.00   62
 21  ω     46.00  78.00   0.50    0.08    --   61.92-125.00  60.00   64
 22  ω     39.00  71.00   0.50    0.08    --   61.92-125.00 -60.00   64
 23  ω     44.00  77.00   0.50    0.08    --   61.92-125.00-120.00   66
 24  ω     23.00  80.00   0.50    0.08    --   61.92-125.00-150.00  114
 25  ω     28.00  53.00   0.50    0.08    --   61.92-125.00-180.00   50
 26  ω     33.00  58.00   0.50    0.08    --   71.24-125.00-120.00   50
 27  ω     64.00  89.00   0.50    0.08    --   71.24-125.00-120.00   50
 28  ω     53.00  87.00   0.50    0.08    --   71.24-125.00   0.00   68
 29  ω     36.00  92.00   0.50    0.08    --   74.15-125.00  60.00  112
 30  ω     36.00  65.00   0.50    0.08    --   61.92-125.00  90.00   58
 31  ω     48.00  89.00   0.50    0.08    --   71.24-125.00 120.00   82
 32  ω     58.00  92.00   0.50    0.08    --   74.15-125.00 150.00   68
 33  ω     37.00  92.00   0.50    0.08    --   74.15-125.00 -30.00  110
 34  ω     46.00  92.00   0.50    0.08    --   74.15-125.00 -60.00   92
 35  ω     50.00  92.00   0.50    0.08    --   74.15-125.00 -90.00   84
 36  ω     59.00  85.00   0.50    0.08    --   74.15-125.00-150.00   52
 37  ω     39.00  81.00   0.50    0.08    --   74.15-125.00-180.00   84
 38  ω     46.00  72.00   0.50    0.08    --   74.15-125.00  30.00   52
 39  ω     66.00  91.00   0.50    0.08    --   74.15-125.00 120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, SynergyCustom 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      0.1341983500
_diffrn_orient_matrix_UB_12      0.0732205500
_diffrn_orient_matrix_UB_13      0.0068050500
_diffrn_orient_matrix_UB_21      0.0021584000
_diffrn_orient_matrix_UB_22      -0.0147465000
_diffrn_orient_matrix_UB_23      -0.0505337000
_diffrn_orient_matrix_UB_31      -0.0338886000
_diffrn_orient_matrix_UB_32      0.2897968000
_diffrn_orient_matrix_UB_33      -0.0042994000
_diffrn_oxdiff_digest_od_ed      
;

;
_diffrn_oxdiff_measurement_exp_name ZY_168.par
_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         0.511
_reflns_Friedel_fraction_full    0.641
_reflns_Friedel_fraction_max     0.641
_reflns_number_gt                2398
_reflns_number_total             2560
_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 1.171.44.129a (Rigaku OD, 2025)'
_computing_data_collection       
'CrysAlisPro system (CCD 44.129a 64-bit (release 14-11-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.44.129a (Rigaku OD, 2025)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.951
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.166
_refine_ls_abs_structure_details 
;
 Flack x determined using 721 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.43(3)
_refine_ls_extinction_coef       0.0044(10)
_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   1.658
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2560
_refine_ls_number_restraints     247
_refine_ls_R_factor_all          0.1275
_refine_ls_R_factor_gt           0.1242
_refine_ls_restrained_S_all      1.588
_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3376
_refine_ls_wR_factor_ref         0.3428
_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. Rigid body (RIGU) restrains
 Cl1, O1, O2, O3, C1, C2, H2, C3, C4, H4, C5, H5, C6, C10, C11, C12, H12, C13,
 H13, C14, H14A, H14B, H14C, C15, H15A, H15B, C16, C17, C18, H18A, H18B, C19,
 H19, C20, C21, C22, C23, C24, C25, C26, C27, C28
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.009
3. Others
 Sof(H22A)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27)=Sof(C28)=
 Sof(H28)=1-FVAR(1)
 Sof(H22)=Sof(C21)=Sof(H21)=Sof(C20)=Sof(H20)=Sof(C24)=Sof(H24)=Sof(C23)=
 Sof(H23)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C19(H19)
4.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C18(H18A,H18B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C12(H12), C13(H13), C22(H22), C22(H22A), C21(H21),
 C20(H20), C24(H24), C23(H23), C25(H25), C26(H26), C27(H27), C28(H28)
4.d Fitted hexagon refined as free rotating group:
 C22(C21,C20,C16,C24,C23)
4.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
4.f Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.42855(11) 0.6594(4) 0.14723(3) 0.0505(4) Uani 1 1 d . . . . .
O1 O 0.4068(3) 0.4735(8) 0.33656(11) 0.0355(8) Uani 1 1 d . . . . .
O2 O 0.5778(3) 0.5115(8) 0.38746(11) 0.0377(8) Uani 1 1 d . . . . .
O3 O 0.7804(3) 0.7545(8) 0.26791(10) 0.0357(8) Uani 1 1 d . . . . .
H3 H 0.764942 0.596014 0.263795 0.053 Uiso 1 1 calc R U . . .
C1 C 0.4963(4) 0.7184(10) 0.27976(14) 0.0292(8) Uani 1 1 d . . . . .
C2 C 0.4949(4) 0.7611(12) 0.23417(15) 0.0370(10) Uani 1 1 d . . . . .
H2 H 0.540818 0.899496 0.224430 0.044 Uiso 1 1 calc R U . . .
C3 C 0.4296(4) 0.6096(13) 0.20390(15) 0.0376(9) Uani 1 1 d . . . . .
C4 C 0.3652(5) 0.3940(12) 0.21715(15) 0.0374(9) Uani 1 1 d . . . . .
H4 H 0.325683 0.277769 0.195664 0.045 Uiso 1 1 calc R U . . .
C5 C 0.3605(5) 0.3547(11) 0.26223(15) 0.0342(10) Uani 1 1 d . . . . .
H5 H 0.314735 0.215150 0.271676 0.041 Uiso 1 1 calc R U . . .
C6 C 0.4213(4) 0.5158(11) 0.29268(15) 0.0305(8) Uani 1 1 d . . . . .
C10 C 0.6828(4) 0.7354(10) 0.33478(15) 0.0318(8) Uani 1 1 d . . . . .
C11 C 0.6814(4) 0.5684(11) 0.36765(15) 0.0337(8) Uani 1 1 d . . . . .
C12 C 0.7843(5) 0.4217(11) 0.39045(15) 0.0344(9) Uani 1 1 d . . . . .
H12 H 0.860988 0.457228 0.381893 0.041 Uiso 1 1 calc R U . . .
C13 C 0.7793(5) 0.2410(11) 0.42247(15) 0.0367(9) Uani 1 1 d . . . . .
H13 H 0.703426 0.206058 0.431763 0.044 Uiso 1 1 calc R U . . .
C14 C 0.8849(5) 0.0940(13) 0.44395(17) 0.0430(12) Uani 1 1 d . . . . .
H14A H 0.865062 -0.091320 0.444446 0.064 Uiso 1 1 calc R U . . .
H14B H 0.906735 0.156432 0.474447 0.064 Uiso 1 1 calc R U . . .
H14C H 0.952588 0.119787 0.427172 0.064 Uiso 1 1 calc R U . . .
C15 C 0.7947(4) 0.8097(11) 0.31448(15) 0.0330(10) Uani 1 1 d . . . . .
H15A H 0.810979 0.997362 0.319245 0.040 Uiso 1 1 calc R U . . .
H15B H 0.864523 0.711965 0.329511 0.040 Uiso 1 1 calc R U . . .
C17 C 0.4686(4) 0.6319(12) 0.37043(14) 0.0336(7) Uani 1 1 d . . . . .
C18 C 0.4904(5) 0.9048(11) 0.35421(16) 0.0368(9) Uani 1 1 d . . . . .
H18A H 0.533584 1.010587 0.378488 0.044 Uiso 1 1 calc R U . . .
H18B H 0.413263 0.991126 0.343368 0.044 Uiso 1 1 calc R U . . .
C19 C 0.5671(4) 0.8723(10) 0.31611(15) 0.0316(8) Uani 1 1 d . . . . .
H19 H 0.586223 1.047118 0.304526 0.038 Uiso 1 1 calc R U . . .
C22 C 0.2580(3) 0.6210(8) 0.47866(10) 0.0563(7) Uani 1 1 d G . . . .
H22 H 0.210975 0.620387 0.502436 0.068 Uiso 0.494(5) 1 calc R U P A 1
H22A H 0.240184 0.622154 0.508368 0.068 Uiso 0.506(5) 1 calc R U P A 2
C21 C 0.3826(3) 0.6204(11) 0.48756(11) 0.057(3) Uani 0.494(5) 1 d G . P A 1
H21 H 0.420765 0.619389 0.517425 0.068 Uiso 0.494(5) 1 calc R U P A 1
C20 C 0.4513(3) 0.6214(14) 0.45277(15) 0.067(4) Uani 0.494(5) 1 d G . P A 1
H20 H 0.536513 0.620961 0.458859 0.080 Uiso 0.494(5) 1 calc R U P A 1
C16 C 0.3955(4) 0.6229(14) 0.40908(13) 0.0340(6) Uani 1 1 d G . . A .
C24 C 0.2709(4) 0.6235(12) 0.40018(10) 0.040(2) Uani 0.494(5) 1 d G . P A 1
H24 H 0.232682 0.624529 0.370314 0.048 Uiso 0.494(5) 1 calc R U P A 1
C23 C 0.2021(3) 0.6226(11) 0.43497(11) 0.046(2) Uani 0.494(5) 1 d G . P A 1
H23 H 0.116932 0.622957 0.428880 0.055 Uiso 0.494(5) 1 calc R U P A 1
C25 C 0.3393(9) 0.853(2) 0.4235(3) 0.0351(10) Uani 0.506(5) 1 d . . P A 2
H25 H 0.353753 1.013947 0.410012 0.042 Uiso 0.506(5) 1 calc R U P A 2
C26 C 0.2663(11) 0.849(3) 0.4557(3) 0.0453(11) Uani 0.506(5) 1 d . . P A 2
H26 H 0.222372 0.998395 0.462089 0.054 Uiso 0.506(5) 1 calc R U P A 2
C27 C 0.2765(10) 0.387(3) 0.4569(3) 0.0421(11) Uani 0.506(5) 1 d . . P A 2
H27 H 0.239067 0.229256 0.463993 0.050 Uiso 0.506(5) 1 calc R U P A 2
C28 C 0.3536(9) 0.397(2) 0.4241(3) 0.0353(10) Uani 0.506(5) 1 d . . P A 2
H28 H 0.377473 0.238690 0.411826 0.042 Uiso 0.506(5) 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
Cl1 C3 1.739(5) . ?
O1 C6 1.382(6) . ?
O1 C17 1.419(6) . ?
O2 C11 1.411(6) . ?
O2 C17 1.409(6) . ?
O3 H3 0.8400 . ?
O3 C15 1.431(5) . ?
C1 C2 1.400(6) . ?
C1 C6 1.428(7) . ?
C1 C19 1.498(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.346(7) . ?
C3 C4 1.412(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.357(7) . ?
C10 C11 1.319(7) . ?
C10 C15 1.522(7) . ?
C10 C19 1.520(7) . ?
C11 C12 1.474(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.353(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.483(8) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C17 C18 1.519(8) . ?
C17 C16 1.521(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.542(7) . ?
C19 H19 1.0000 . ?
C22 H22 0.9500 . ?
C22 H22A 0.9500 . ?
C22 C21 1.3900 . ?
C22 C23 1.3900 . ?
C22 C26 1.373(14) . ?
C22 C27 1.405(13) . ?
C21 H21 0.9500 . ?
C21 C20 1.3900 . ?
C20 H20 0.9500 . ?
C20 C16 1.3900 . ?
C16 C24 1.3900 . ?
C16 C25 1.436(13) . ?
C16 C28 1.354(13) . ?
C24 H24 0.9500 . ?
C24 C23 1.3900 . ?
C23 H23 0.9500 . ?
C25 H25 0.9500 . ?
C25 C26 1.357(15) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C27 C28 1.407(15) . ?
C28 H28 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
C6 O1 C17 119.9(4) . . ?
C17 O2 C11 118.6(4) . . ?
C15 O3 H3 109.5 . . ?
C2 C1 C6 117.2(4) . . ?
C2 C1 C19 125.5(5) . . ?
C6 C1 C19 117.3(4) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(5) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 Cl1 121.4(4) . . ?
C2 C3 C4 120.9(4) . . ?
C4 C3 Cl1 117.5(4) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.8(5) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(5) . . ?
C6 C5 H5 120.0 . . ?
O1 C6 C1 122.0(4) . . ?
C5 C6 O1 116.6(5) . . ?
C5 C6 C1 121.4(4) . . ?
C11 C10 C15 124.4(4) . . ?
C11 C10 C19 119.2(5) . . ?
C15 C10 C19 116.4(4) . . ?
O2 C11 C12 109.5(4) . . ?
C10 C11 O2 123.5(5) . . ?
C10 C11 C12 127.0(5) . . ?
C11 C12 H12 117.1 . . ?
C13 C12 C11 125.7(5) . . ?
C13 C12 H12 117.1 . . ?
C12 C13 H13 118.0 . . ?
C12 C13 C14 124.0(5) . . ?
C14 C13 H13 118.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 C10 111.2(4) . . ?
O3 C15 H15A 109.4 . . ?
O3 C15 H15B 109.4 . . ?
C10 C15 H15A 109.4 . . ?
C10 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
O1 C17 C18 112.4(4) . . ?
O1 C17 C16 106.2(4) . . ?
O2 C17 O1 109.3(4) . . ?
O2 C17 C18 110.8(4) . . ?
O2 C17 C16 103.7(4) . . ?
C18 C17 C16 113.9(5) . . ?
C17 C18 H18A 110.6 . . ?
C17 C18 H18B 110.6 . . ?
C17 C18 C19 105.9(4) . . ?
H18A C18 H18B 108.7 . . ?
C19 C18 H18A 110.6 . . ?
C19 C18 H18B 110.6 . . ?
C1 C19 C10 111.9(4) . . ?
C1 C19 C18 108.4(4) . . ?
C1 C19 H19 109.6 . . ?
C10 C19 C18 107.8(4) . . ?
C10 C19 H19 109.6 . . ?
C18 C19 H19 109.6 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0 . . ?
C23 C22 H22 120.0 . . ?
C26 C22 H22A 121.0 . . ?
C26 C22 C27 118.0(7) . . ?
C27 C22 H22A 121.0 . . ?
C22 C21 H21 120.0 . . ?
C22 C21 C20 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C20 H20 120.0 . . ?
C16 C20 C21 120.0 . . ?
C16 C20 H20 120.0 . . ?
C20 C16 C17 121.0(3) . . ?
C20 C16 C24 120.0 . . ?
C24 C16 C17 118.9(3) . . ?
C25 C16 C17 121.0(6) . . ?
C28 C16 C17 122.2(7) . . ?
C28 C16 C25 114.6(7) . . ?
C16 C24 H24 120.0 . . ?
C16 C24 C23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23 120.0 . . ?
C16 C25 H25 118.7 . . ?
C26 C25 C16 122.7(10) . . ?
C26 C25 H25 118.7 . . ?
C22 C26 H26 121.0 . . ?
C25 C26 C22 117.9(11) . . ?
C25 C26 H26 121.0 . . ?
C22 C27 H27 121.8 . . ?
C28 C27 C22 116.3(10) . . ?
C28 C27 H27 121.8 . . ?
C16 C28 C27 123.1(10) . . ?
C16 C28 H28 118.4 . . ?
C27 C28 H28 118.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C3 C4 C5 -177.6(4) . . . . ?
O1 C17 C18 C19 -60.2(5) . . . . ?
O1 C17 C16 C20 143.3(3) . . . . ?
O1 C17 C16 C24 -38.5(6) . . . . ?
O1 C17 C16 C25 -115.8(7) . . . . ?
O1 C17 C16 C28 46.8(7) . . . . ?
O2 C11 C12 C13 6.0(7) . . . . ?
O2 C17 C18 C19 62.4(5) . . . . ?
O2 C17 C16 C20 28.1(6) . . . . ?
O2 C17 C16 C24 -153.7(4) . . . . ?
O2 C17 C16 C25 129.1(6) . . . . ?
O2 C17 C16 C28 -68.4(7) . . . . ?
C1 C2 C3 Cl1 -179.4(4) . . . . ?
C1 C2 C3 C4 -3.3(8) . . . . ?
C2 C1 C6 O1 -173.6(5) . . . . ?
C2 C1 C6 C5 6.4(7) . . . . ?
C2 C1 C19 C10 -99.2(6) . . . . ?
C2 C1 C19 C18 142.0(5) . . . . ?
C2 C3 C4 C5 6.2(8) . . . . ?
C3 C4 C5 C6 -2.7(8) . . . . ?
C4 C5 C6 O1 176.4(5) . . . . ?
C4 C5 C6 C1 -3.6(8) . . . . ?
C6 O1 C17 O2 -93.5(5) . . . . ?
C6 O1 C17 C18 30.0(6) . . . . ?
C6 O1 C17 C16 155.3(4) . . . . ?
C6 C1 C2 C3 -2.9(8) . . . . ?
C6 C1 C19 C10 82.7(5) . . . . ?
C6 C1 C19 C18 -36.1(6) . . . . ?
C10 C11 C12 C13 -176.2(5) . . . . ?
C11 O2 C17 O1 90.2(5) . . . . ?
C11 O2 C17 C18 -34.2(6) . . . . ?
C11 O2 C17 C16 -156.8(5) . . . . ?
C11 C10 C15 O3 121.7(5) . . . . ?
C11 C10 C19 C1 -88.0(6) . . . . ?
C11 C10 C19 C18 31.1(6) . . . . ?
C11 C12 C13 C14 178.8(5) . . . . ?
C15 C10 C11 O2 176.8(5) . . . . ?
C15 C10 C11 C12 -0.7(9) . . . . ?
C15 C10 C19 C1 93.8(5) . . . . ?
C15 C10 C19 C18 -147.1(4) . . . . ?
C17 O1 C6 C1 -0.8(7) . . . . ?
C17 O1 C6 C5 179.3(5) . . . . ?
C17 O2 C11 C10 2.3(7) . . . . ?
C17 O2 C11 C12 -179.8(4) . . . . ?
C17 C18 C19 C1 62.0(5) . . . . ?
C17 C18 C19 C10 -59.4(5) . . . . ?
C17 C16 C24 C23 -178.2(5) . . . . ?
C17 C16 C25 C26 175.1(8) . . . . ?
C17 C16 C28 C27 -173.8(8) . . . . ?
C18 C17 C16 C20 -92.5(5) . . . . ?
C18 C17 C16 C24 85.7(5) . . . . ?
C18 C17 C16 C25 8.5(8) . . . . ?
C18 C17 C16 C28 171.0(6) . . . . ?
C19 C1 C2 C3 179.0(5) . . . . ?
C19 C1 C6 O1 4.7(7) . . . . ?
C19 C1 C6 C5 -175.3(5) . . . . ?
C19 C10 C11 O2 -1.2(8) . . . . ?
C19 C10 C11 C12 -178.8(5) . . . . ?
C19 C10 C15 O3 -60.2(6) . . . . ?
C22 C21 C20 C16 0.0 . . . . ?
C22 C27 C28 C16 -9.1(14) . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C21 C20 C16 C17 178.2(5) . . . . ?
C21 C20 C16 C24 0.0 . . . . ?
C20 C16 C24 C23 0.0 . . . . ?
C16 C17 C18 C19 178.9(4) . . . . ?
C16 C24 C23 C22 0.0 . . . . ?
C16 C25 C26 C22 7.9(15) . . . . ?
C23 C22 C21 C20 0.0 . . . . ?
C25 C16 C28 C27 -10.2(12) . . . . ?
C26 C22 C27 C28 28.9(12) . . . . ?
C27 C22 C26 C25 -28.3(13) . . . . ?
C28 C16 C25 C26 11.3(12) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.858
_oxdiff_exptl_absorpt_empirical_full_min 0.553
####################################################################### 
# 
# 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_201905122
_database_code_depnum_ccdc_archive 'CCDC 2502855'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2025-11-14 deposited with the CCDC.	2026-02-02 downloaded from the CCDC.
;
_audit_creation_date             2019-05-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 O4'
_chemical_formula_sum            'C21 H14 O4'
_chemical_formula_weight         330.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.4615(3)
_cell_length_b                   7.4413(3)
_cell_length_c                   22.9597(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.165(3)
_cell_angle_gamma                90
_cell_volume                     1603.87(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2098
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.1940
_cell_measurement_theta_min      4.8650
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.879
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            6385
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.781
_diffrn_reflns_theta_min         3.881
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -36.00   -4.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  113.0000 -168.0000 32

#__ type_ start__ end____ width___ exp.time_
  2 omega  -69.00  -42.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  113.0000 -168.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -45.00    8.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
  4 omega  -38.00  -12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   12.00   39.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   46.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  120.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega   27.00   99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -150.0000 72

#__ type_ start__ end____ width___ exp.time_
  8 omega   -1.00   35.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
  9 omega  -36.00   16.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000   90.0000 52

#__ type_ start__ end____ width___ exp.time_
 10 omega   57.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 48

#__ type_ start__ end____ width___ exp.time_
 11 omega   40.00   73.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 33

#__ type_ start__ end____ width___ exp.time_
 12 omega   39.00   70.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 31

#__ type_ start__ end____ width___ exp.time_
 13 omega   39.00   88.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 49

#__ type_ start__ end____ width___ exp.time_
 14 omega   76.00  106.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
 15 omega   69.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 46

#__ type_ start__ end____ width___ exp.time_
 16 omega   41.00  100.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 59

#__ type_ start__ end____ width___ exp.time_
 17 omega   45.00   77.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
 18 omega   38.00   64.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   48.00   74.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   91.00  162.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 71

#__ type_ start__ end____ width___ exp.time_
 21 omega   50.00   83.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
 22 omega   93.00  157.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   90.0000 64

#__ type_ start__ end____ width___ exp.time_
 23 omega  119.00  168.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0047590000
_diffrn_orient_matrix_UB_12      -0.1180519000
_diffrn_orient_matrix_UB_13      -0.0548212000
_diffrn_orient_matrix_UB_21      -0.0112281000
_diffrn_orient_matrix_UB_22      -0.1698267000
_diffrn_orient_matrix_UB_23      0.0375348000
_diffrn_orient_matrix_UB_31      -0.1636768000
_diffrn_orient_matrix_UB_32      0.0081515000
_diffrn_orient_matrix_UB_33      -0.0126350000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2338
_reflns_number_total             3019
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.205
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3019
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.025
_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)+(0.0774P)²+0.1056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1411
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C13(H13), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7322(2) 0.1999(3) 0.50753(9) 0.0529(5) Uani 1 1 d . . . . .
H1 H 0.7795 0.2252 0.5446 0.063 Uiso 1 1 calc R . . . .
C2 C 0.8080(2) 0.1367(3) 0.46402(11) 0.0636(6) Uani 1 1 d . . . . .
H2 H 0.9059 0.1201 0.4721 0.076 Uiso 1 1 calc R . . . .
C3 C 0.7394(3) 0.0979(3) 0.40862(10) 0.0654(6) Uani 1 1 d . . . . .
H3 H 0.7915 0.0552 0.3797 0.078 Uiso 1 1 calc R . . . .
C4 C 0.5949(2) 0.1221(3) 0.39612(9) 0.0584(5) Uani 1 1 d . . . . .
H4 H 0.5482 0.0964 0.3590 0.070 Uiso 1 1 calc R . . . .
C5 C 0.5201(2) 0.1858(2) 0.44026(8) 0.0461(4) Uani 1 1 d . . . . .
C6 C 0.58459(17) 0.2262(2) 0.49630(8) 0.0412(4) Uani 1 1 d . . . . .
C7 C 0.49498(16) 0.2920(2) 0.53959(7) 0.0373(4) Uani 1 1 d . . . . .
C8 C 0.34814(17) 0.3091(2) 0.52180(7) 0.0394(4) Uani 1 1 d . . . . .
C9 C 0.28817(19) 0.2693(3) 0.46204(8) 0.0495(4) Uani 1 1 d . . . . .
C10 C 0.25687(16) 0.3649(2) 0.56243(8) 0.0415(4) Uani 1 1 d . . . . .
C11 C 0.31066(16) 0.4028(2) 0.62056(7) 0.0394(4) Uani 1 1 d . . . . .
C12 C 0.45825(16) 0.3905(2) 0.63740(7) 0.0377(4) Uani 1 1 d . . . . .
C13 C 0.54790(16) 0.3350(2) 0.59712(7) 0.0398(4) Uani 1 1 d . . . . .
H13 H 0.6453 0.3266 0.6090 0.048 Uiso 1 1 calc R . . . .
C14 C 0.21248(18) 0.4679(3) 0.66305(8) 0.0479(4) Uani 1 1 d . . . . .
C15 C 0.0863(3) 0.3543(4) 0.67271(12) 0.0823(8) Uani 1 1 d . . . . .
H15A H 0.1159 0.2612 0.7005 0.123 Uiso 1 1 calc GR . . . .
H15B H 0.0468 0.3011 0.6362 0.123 Uiso 1 1 calc GR . . . .
H15C H 0.0156 0.4279 0.6876 0.123 Uiso 1 1 calc GR . . . .
C16 C 0.52352(17) 0.4282(2) 0.69858(7) 0.0398(4) Uani 1 1 d . . . . .
C17 C 0.63905(19) 0.5428(3) 0.70879(8) 0.0504(4) Uani 1 1 d . . . . .
H17 H 0.6726 0.6014 0.6775 0.060 Uiso 1 1 calc R . . . .
C18 C 0.7052(2) 0.5710(3) 0.76543(9) 0.0603(5) Uani 1 1 d . . . . .
H18 H 0.7819 0.6497 0.7720 0.072 Uiso 1 1 calc R . . . .
C19 C 0.6577(2) 0.4829(3) 0.81207(8) 0.0563(5) Uani 1 1 d . . . . .
H19 H 0.7028 0.5012 0.8500 0.068 Uiso 1 1 calc R . . . .
C20 C 0.5430(2) 0.3674(3) 0.80233(8) 0.0524(5) Uani 1 1 d . . . . .
H20 H 0.5112 0.3072 0.8337 0.063 Uiso 1 1 calc R . . . .
C21 C 0.47549(18) 0.3412(3) 0.74612(8) 0.0460(4) Uani 1 1 d . . . . .
H21 H 0.3973 0.2648 0.7399 0.055 Uiso 1 1 calc R . . . .
O1 O 0.37508(14) 0.2073(2) 0.42420(5) 0.0540(4) Uani 1 1 d . . . . .
O2 O 0.16301(15) 0.2878(3) 0.44261(6) 0.0724(5) Uani 1 1 d . . . . .
O3 O 0.11600(12) 0.3868(2) 0.54619(6) 0.0584(4) Uani 1 1 d . . . . .
H3A H 0.0978 0.3696 0.5108 0.088 Uiso 1 1 calc GR . . . .
O4 O 0.24031(15) 0.6044(2) 0.69030(7) 0.0624(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.383(3) . ?
C1 C6 1.402(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(2) . ?
C5 C6 1.386(3) . ?
C5 O1 1.385(2) . ?
C6 C7 1.468(2) . ?
C7 C8 1.404(2) . ?
C7 C13 1.390(2) . ?
C8 C9 1.449(2) . ?
C8 C10 1.410(2) . ?
C9 O1 1.350(2) . ?
C9 O2 1.220(2) . ?
C10 C11 1.396(2) . ?
C10 O3 1.3484(19) . ?
C11 C12 1.405(2) . ?
C11 C14 1.509(2) . ?
C12 C13 1.393(2) . ?
C12 C16 1.489(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.501(3) . ?
C14 O4 1.205(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.383(2) . ?
C16 C21 1.393(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.378(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.380(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.381(2) . ?
C21 H21 0.9300 . ?
O3 H3A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.7 . . ?
C2 C1 C6 120.6(2) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.32(18) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.5(2) . . ?
C5 C4 H4 120.8 . . ?
C6 C5 C4 123.06(18) . . ?
O1 C5 C4 115.03(17) . . ?
O1 C5 C6 121.91(15) . . ?
C1 C6 C7 124.61(17) . . ?
C5 C6 C1 116.96(17) . . ?
C5 C6 C7 118.43(15) . . ?
C8 C7 C6 117.86(15) . . ?
C13 C7 C6 123.36(14) . . ?
C13 C7 C8 118.78(14) . . ?
C7 C8 C9 120.89(15) . . ?
C7 C8 C10 119.97(15) . . ?
C10 C8 C9 119.13(15) . . ?
O1 C9 C8 118.78(15) . . ?
O2 C9 C8 124.82(17) . . ?
O2 C9 O1 116.41(16) . . ?
C11 C10 C8 120.75(14) . . ?
O3 C10 C8 121.22(16) . . ?
O3 C10 C11 118.01(15) . . ?
C10 C11 C12 118.76(14) . . ?
C10 C11 C14 120.17(14) . . ?
C12 C11 C14 120.93(15) . . ?
C11 C12 C16 121.91(14) . . ?
C13 C12 C11 120.21(15) . . ?
C13 C12 C16 117.83(14) . . ?
C7 C13 C12 121.46(14) . . ?
C7 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C15 C14 C11 118.65(18) . . ?
O4 C14 C11 119.63(16) . . ?
O4 C14 C15 121.63(18) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C12 120.14(15) . . ?
C17 C16 C21 118.81(16) . . ?
C21 C16 C12 120.94(15) . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.43(17) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.30(18) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.74(17) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.14(17) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.56(17) . . ?
C20 C21 H21 119.7 . . ?
C9 O1 C5 122.08(14) . . ?
C10 O3 H3A 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A O2 0.82 1.85 2.581(2) 146.8 .

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
C1 C2 C3 C4 0.1(3) . . . . ?
C1 C6 C7 C8 -179.18(17) . . . . ?
C1 C6 C7 C13 -0.2(3) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C1 C6 C7 179.74(18) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C3 C4 C5 O1 179.74(18) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C4 C5 C6 C7 -179.74(17) . . . . ?
C4 C5 O1 C9 -179.49(18) . . . . ?
C5 C6 C7 C8 0.4(2) . . . . ?
C5 C6 C7 C13 179.38(16) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C6 C5 O1 C9 0.2(3) . . . . ?
C6 C7 C8 C9 -2.2(2) . . . . ?
C6 C7 C8 C10 177.49(15) . . . . ?
C6 C7 C13 C12 -177.54(15) . . . . ?
C7 C8 C9 O1 3.0(3) . . . . ?
C7 C8 C9 O2 -176.86(19) . . . . ?
C7 C8 C10 C11 -0.3(3) . . . . ?
C7 C8 C10 O3 178.31(16) . . . . ?
C8 C7 C13 C12 1.4(2) . . . . ?
C8 C9 O1 C5 -2.0(3) . . . . ?
C8 C10 C11 C12 2.2(3) . . . . ?
C8 C10 C11 C14 178.08(16) . . . . ?
C9 C8 C10 C11 179.40(16) . . . . ?
C9 C8 C10 O3 -2.0(3) . . . . ?
C10 C8 C9 O1 -176.69(16) . . . . ?
C10 C8 C9 O2 3.4(3) . . . . ?
C10 C11 C12 C13 -2.4(2) . . . . ?
C10 C11 C12 C16 -179.79(15) . . . . ?
C10 C11 C14 C15 56.8(3) . . . . ?
C10 C11 C14 O4 -126.6(2) . . . . ?
C11 C12 C13 C7 0.5(3) . . . . ?
C11 C12 C16 C17 -130.71(18) . . . . ?
C11 C12 C16 C21 53.2(2) . . . . ?
C12 C11 C14 C15 -127.4(2) . . . . ?
C12 C11 C14 O4 49.1(3) . . . . ?
C12 C16 C17 C18 -176.50(18) . . . . ?
C12 C16 C21 C20 175.45(17) . . . . ?
C13 C7 C8 C9 178.78(16) . . . . ?
C13 C7 C8 C10 -1.5(2) . . . . ?
C13 C12 C16 C17 51.8(2) . . . . ?
C13 C12 C16 C21 -124.28(18) . . . . ?
C14 C11 C12 C13 -178.16(16) . . . . ?
C14 C11 C12 C16 4.4(3) . . . . ?
C16 C12 C13 C7 178.07(15) . . . . ?
C16 C17 C18 C19 1.0(3) . . . . ?
C17 C16 C21 C20 -0.7(3) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 C16 1.1(3) . . . . ?
C21 C16 C17 C18 -0.3(3) . . . . ?
O1 C5 C6 C1 -179.73(16) . . . . ?
O1 C5 C6 C7 0.6(3) . . . . ?
O2 C9 O1 C5 177.93(18) . . . . ?
O3 C10 C11 C12 -176.42(16) . . . . ?
O3 C10 C11 C14 -0.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
