# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_ljt-10b
_database_code_depnum_ccdc_archive 'CCDC 2363816'
loop_
_audit_author_name
_audit_author_address
Rigaku
;Jinan University
China
;
_audit_update_record             
;
2024-06-19 deposited with the CCDC.	2024-09-09 downloaded from the CCDC.
;
_audit_creation_date             2024-05-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 O4'
_chemical_formula_sum            'C15 H16 O4'
_chemical_formula_weight         260.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.7545(2)
_cell_length_b                   8.7863(2)
_cell_length_c                   15.2338(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.718(2)
_cell_angle_gamma                90
_cell_volume                     1296.66(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3269
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.9850
_cell_measurement_theta_min      2.8840
_shelx_estimated_absorpt_T_max   0.911
_shelx_estimated_absorpt_T_min   0.897
_exptl_absorpt_coefficient_mu    0.794
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4915
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.722
_diffrn_reflns_theta_min         5.125
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  34.00   1.00    1.00    --  -40.73  38.00 150.00   42
  2  ω    -65.00 -39.00   1.00    1.00    --  -40.73  38.00 150.00   26
  3  ω   -108.00 -60.00   1.00    1.00    --  -40.73 -38.00  90.00   48
  4  ω     26.00  97.00   1.00    1.00    --   40.73-125.00  30.00   71
  5  ω     34.00  96.00   1.00    1.00    --   40.73-125.00 150.00   62
  6  ω     54.00 135.00   1.00    1.00    --  107.58 -30.00  30.00   81
  7  ω    108.00 171.00   1.00    1.00    --  107.58  45.00  60.00   63
  8  ω    101.00 167.00   1.00    1.00    --  107.58 125.00 120.00   66
  9  ω    140.00 169.00   1.00    1.00    --  107.58 125.00-180.00   29
 10  ω     86.00 176.00   1.00    1.00    --  107.58  61.00-180.00   90
 11  ω     36.00  89.00   1.00    1.00    --  107.58 -95.00 -90.00   53
 12  ω     25.00  62.00   1.00    1.00    --  107.58 -95.00 -30.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0410359000
_diffrn_orient_matrix_UB_12      0.1395507000
_diffrn_orient_matrix_UB_13      -0.0582995000
_diffrn_orient_matrix_UB_21      0.1320205000
_diffrn_orient_matrix_UB_22      -0.0184275000
_diffrn_orient_matrix_UB_23      -0.0454292000
_diffrn_orient_matrix_UB_31      -0.0784958000
_diffrn_orient_matrix_UB_32      -0.1045153000
_diffrn_orient_matrix_UB_33      -0.0701015000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2271
_reflns_number_total             2536
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2536
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.055
_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)+(0.0617P)²+0.1944P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1071
_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.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C10(H10A,H10B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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
O4 O 0.79797(10) 0.49035(11) 0.74639(6) 0.0328(2) Uani 1 1 d . . . . .
H4 H 0.843201 0.563628 0.766624 0.049 Uiso 1 1 calc R U . . .
O3 O 0.57005(9) 0.54675(10) 0.84216(5) 0.0291(2) Uani 1 1 d . . . . .
O2 O 0.54867(10) 0.24309(10) 0.68769(6) 0.0373(3) Uani 1 1 d . . . . .
O1 O 0.25178(10) 0.73775(12) 0.54146(6) 0.0383(3) Uani 1 1 d . . . . .
C4 C 0.46338(12) 0.49827(14) 0.70146(8) 0.0275(3) Uani 1 1 d . . . . .
C15 C 0.77016(12) 0.39243(14) 0.81664(7) 0.0263(3) Uani 1 1 d . . . . .
H15 H 0.795028 0.289036 0.800286 0.032 Uiso 1 1 calc R U . . .
C5 C 0.48531(12) 0.59985(14) 0.77109(8) 0.0267(3) Uani 1 1 d . . . . .
C9 C 0.61346(12) 0.39369(14) 0.82101(7) 0.0255(3) Uani 1 1 d . . . . .
C8 C 0.54077(12) 0.36232(14) 0.72816(8) 0.0278(3) Uani 1 1 d . . . . .
C2 C 0.32705(12) 0.68010(15) 0.61529(8) 0.0298(3) Uani 1 1 d . . . . .
C14 C 0.85872(13) 0.43133(15) 0.90246(8) 0.0300(3) Uani 1 1 d . . . . .
H14A H 0.828717 0.528445 0.923723 0.036 Uiso 1 1 calc R U . . .
H14B H 0.953711 0.442784 0.890547 0.036 Uiso 1 1 calc R U . . .
C3 C 0.38363(13) 0.53653(15) 0.62202(8) 0.0299(3) Uani 1 1 d . . . . .
H3 H 0.369464 0.467485 0.575570 0.036 Uiso 1 1 calc R U . . .
C10 C 0.56244(13) 0.27953(15) 0.88603(8) 0.0310(3) Uani 1 1 d . . . . .
H10A H 0.462792 0.272095 0.874005 0.037 Uiso 1 1 calc R U . . .
H10B H 0.600315 0.180262 0.874874 0.037 Uiso 1 1 calc R U . . .
C6 C 0.42482(13) 0.74351(15) 0.76609(9) 0.0312(3) Uani 1 1 d . . . . .
H6 H 0.436945 0.811059 0.813361 0.037 Uiso 1 1 calc R U . . .
C7 C 0.34602(13) 0.78141(15) 0.68789(9) 0.0326(3) Uani 1 1 d . . . . .
H7 H 0.304087 0.876567 0.682773 0.039 Uiso 1 1 calc R U . . .
C11 C 0.59883(14) 0.31691(16) 0.98226(8) 0.0350(3) Uani 1 1 d . . . . .
H11 H 0.526955 0.333988 1.016135 0.042 Uiso 1 1 calc R U . . .
C12 C 0.72698(15) 0.32704(17) 1.02182(8) 0.0371(3) Uani 1 1 d . . . . .
H12 H 0.739221 0.344530 1.082446 0.045 Uiso 1 1 calc R U . . .
C13 C 0.85322(14) 0.31218(17) 0.97533(8) 0.0357(3) Uani 1 1 d . . . . .
H13A H 0.855093 0.211363 0.949544 0.043 Uiso 1 1 calc R U . . .
H13B H 0.934500 0.322667 1.018107 0.043 Uiso 1 1 calc R U . . .
C1 C 0.23366(16) 0.64110(19) 0.46577(9) 0.0428(4) Uani 1 1 d . . . . .
H1A H 0.181695 0.552784 0.478745 0.064 Uiso 1 1 calc R U . . .
H1B H 0.322299 0.610217 0.450575 0.064 Uiso 1 1 calc R U . . .
H1C H 0.184799 0.695242 0.417050 0.064 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 H4 0.8200 . ?
O4 C15 1.4237(14) . ?
O3 C5 1.3652(14) . ?
O3 C9 1.4573(14) . ?
O2 C8 1.2226(15) . ?
O1 C2 1.3666(14) . ?
O1 C1 1.4262(17) . ?
C4 C5 1.3836(17) . ?
C4 C8 1.4458(17) . ?
C4 C3 1.4009(17) . ?
C15 H15 0.9800 . ?
C15 C9 1.5377(16) . ?
C15 C14 1.5193(16) . ?
C5 C6 1.3917(17) . ?
C9 C8 1.5313(15) . ?
C9 C10 1.5331(17) . ?
C2 C3 1.3759(18) . ?
C2 C7 1.4148(18) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.5313(17) . ?
C3 H3 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.5037(18) . ?
C6 H6 0.9300 . ?
C6 C7 1.3808(18) . ?
C7 H7 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.326(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.496(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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
C15 O4 H4 109.5 . . ?
C5 O3 C9 107.74(9) . . ?
C2 O1 C1 116.65(11) . . ?
C5 C4 C8 106.76(10) . . ?
C5 C4 C3 121.87(11) . . ?
C3 C4 C8 131.32(11) . . ?
O4 C15 H15 107.1 . . ?
O4 C15 C9 107.82(9) . . ?
O4 C15 C14 111.82(10) . . ?
C9 C15 H15 107.1 . . ?
C14 C15 H15 107.1 . . ?
C14 C15 C9 115.41(10) . . ?
O3 C5 C4 114.36(11) . . ?
O3 C5 C6 124.53(11) . . ?
C4 C5 C6 121.10(11) . . ?
O3 C9 C15 109.40(9) . . ?
O3 C9 C8 104.78(9) . . ?
O3 C9 C10 109.65(9) . . ?
C8 C9 C15 108.30(9) . . ?
C8 C9 C10 109.20(10) . . ?
C10 C9 C15 115.01(10) . . ?
O2 C8 C4 128.88(11) . . ?
O2 C8 C9 124.78(11) . . ?
C4 C8 C9 106.34(10) . . ?
O1 C2 C3 124.98(11) . . ?
O1 C2 C7 114.75(11) . . ?
C3 C2 C7 120.26(11) . . ?
C15 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C15 C14 C13 113.92(10) . . ?
H14A C14 H14B 107.7 . . ?
C13 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
C4 C3 H3 121.3 . . ?
C2 C3 C4 117.50(11) . . ?
C2 C3 H3 121.3 . . ?
C9 C10 H10A 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 C9 115.44(11) . . ?
C11 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C5 C6 H6 121.4 . . ?
C7 C6 C5 117.10(12) . . ?
C7 C6 H6 121.4 . . ?
C2 C7 H7 119.0 . . ?
C6 C7 C2 122.10(12) . . ?
C6 C7 H7 119.0 . . ?
C10 C11 H11 118.0 . . ?
C12 C11 C10 124.08(12) . . ?
C12 C11 H11 118.0 . . ?
C11 C12 H12 117.9 . . ?
C11 C12 C13 124.29(11) . . ?
C13 C12 H12 117.9 . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C12 C13 C14 112.58(11) . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
O4 C15 C9 O3 -63.03(11) . . . . ?
O4 C15 C9 C8 50.64(12) . . . . ?
O4 C15 C9 C10 173.08(9) . . . . ?
O4 C15 C14 C13 -169.06(10) . . . . ?
O3 C5 C6 C7 177.53(11) . . . . ?
O3 C9 C8 O2 -178.24(12) . . . . ?
O3 C9 C8 C4 1.04(12) . . . . ?
O3 C9 C10 C11 -52.31(14) . . . . ?
O1 C2 C3 C4 177.10(12) . . . . ?
O1 C2 C7 C6 -176.98(12) . . . . ?
C4 C5 C6 C7 -1.98(18) . . . . ?
C15 C9 C8 O2 65.08(16) . . . . ?
C15 C9 C8 C4 -115.65(11) . . . . ?
C15 C9 C10 C11 71.45(14) . . . . ?
C15 C14 C13 C12 -80.09(14) . . . . ?
C5 O3 C9 C15 114.99(10) . . . . ?
C5 O3 C9 C8 -0.93(12) . . . . ?
C5 O3 C9 C10 -118.01(10) . . . . ?
C5 C4 C8 O2 178.47(13) . . . . ?
C5 C4 C8 C9 -0.77(13) . . . . ?
C5 C4 C3 C2 -0.01(19) . . . . ?
C5 C6 C7 C2 -0.23(19) . . . . ?
C9 O3 C5 C4 0.50(14) . . . . ?
C9 O3 C5 C6 -179.04(11) . . . . ?
C9 C15 C14 C13 67.21(15) . . . . ?
C9 C10 C11 C12 -62.01(19) . . . . ?
C8 C4 C5 O3 0.20(15) . . . . ?
C8 C4 C5 C6 179.75(11) . . . . ?
C8 C4 C3 C2 -176.93(13) . . . . ?
C8 C9 C10 C11 -166.59(11) . . . . ?
C14 C15 C9 O3 62.78(13) . . . . ?
C14 C15 C9 C8 176.44(10) . . . . ?
C14 C15 C9 C10 -61.12(14) . . . . ?
C3 C4 C5 O3 -177.39(11) . . . . ?
C3 C4 C5 C6 2.17(19) . . . . ?
C3 C4 C8 O2 -4.3(2) . . . . ?
C3 C4 C8 C9 176.50(13) . . . . ?
C3 C2 C7 C6 2.4(2) . . . . ?
C10 C9 C8 O2 -60.84(16) . . . . ?
C10 C9 C8 C4 118.43(11) . . . . ?
C10 C11 C12 C13 3.9(2) . . . . ?
C7 C2 C3 C4 -2.18(19) . . . . ?
C11 C12 C13 C14 59.36(19) . . . . ?
C1 O1 C2 C3 -1.18(19) . . . . ?
C1 O1 C2 C7 178.14(12) . . . . ?

_olex2_date_sample_data_collection 2022-09-22
_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 1.376
_oxdiff_exptl_absorpt_empirical_full_min 0.672
####################################################################### 
# 
# 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_hyj-2-30-b2
_database_code_depnum_ccdc_archive 'CCDC 2363819'
loop_
_audit_author_name
_audit_author_address
Rigaku
;Jinan University
China
;
_audit_update_record             
;
2024-06-19 deposited with the CCDC.	2024-09-09 downloaded from the CCDC.
;
_audit_creation_date             2024-05-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 F3 O7 S'
_chemical_formula_sum            'C16 H13 F3 O7 S'
_chemical_formula_weight         406.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   10.7585(10)
_cell_length_b                   14.0755(16)
_cell_length_c                   11.0794(11)
_cell_angle_alpha                90
_cell_angle_beta                 100.732(9)
_cell_angle_gamma                90
_cell_volume                     1648.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2882
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.7550
_cell_measurement_theta_min      5.1430
_shelx_estimated_absorpt_T_max   0.793
_shelx_estimated_absorpt_T_min   0.727
_exptl_absorpt_coefficient_mu    2.436
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33220
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.14
_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  0.0625
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5943
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.583
_diffrn_reflns_theta_max         66.583
_diffrn_reflns_theta_min         5.136
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     17.00  86.00   1.00    1.00    --   40.92  37.00 120.00   69
  2  ω    150.00 178.00   1.00    2.27    --  107.58 125.00 150.00   28
  3  ω     94.00 168.00   1.00    2.27    --  107.58 125.00   0.00   74
  4  ω     82.00 178.00   1.00    2.27    --  107.58  45.00-180.00   96
  5  ω     67.00  94.00   1.00    2.27    --  107.58 -45.00 -90.00   27
  6  ω     35.00  62.00   1.00    2.27    --  107.58 -45.00 -90.00   27
  7  ω     22.00  50.00   1.00    1.00    --   40.92 -99.00-120.00   28
  8  ω     47.00  87.00   1.00    1.00    --   40.92-125.00-180.00   40
  9  ω     28.00 101.00   1.00    1.00    --   40.92  37.00-180.00   73
 10  ω     79.00 106.00   1.00    2.27    --  107.58 -94.00  90.00   27
 11  ω     65.00 104.00   1.00    2.27    --  107.58 -94.00 150.00   39
 12  ω     28.00  63.00   1.00    2.27    --  107.58 -94.00 150.00   35
 13  ω     26.00  61.00   1.00    2.27    --  107.58 -94.00  90.00   35
 14  ω     69.00 141.00   1.00    2.27    --  107.58  15.00 150.00   72
 15  ω   -113.00 -73.00   1.00    1.00    --  -40.92 -37.00-120.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0477290000
_diffrn_orient_matrix_UB_12      0.0786229000
_diffrn_orient_matrix_UB_13      0.0767285000
_diffrn_orient_matrix_UB_21      -0.0295656000
_diffrn_orient_matrix_UB_22      -0.0753337000
_diffrn_orient_matrix_UB_23      0.0914982000
_diffrn_orient_matrix_UB_31      0.1343464000
_diffrn_orient_matrix_UB_32      0.0115931000
_diffrn_orient_matrix_UB_33      0.0761289000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2301
_reflns_number_total             2900
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2900
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0759
_refine_ls_restrained_S_all      1.062
_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)+(0.1600P)²+0.2944P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2127
_refine_ls_wR_factor_ref         0.2404
_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:
 C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C13(H13)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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
S1 S 0.20905(8) 0.58363(7) 0.05543(8) 0.0400(4) Uani 1 1 d . . . . .
F1 F 0.3378(3) 0.4478(2) -0.0233(4) 0.0786(9) Uani 1 1 d . . . . .
F2 F 0.2353(3) 0.5365(3) -0.1637(2) 0.0784(10) Uani 1 1 d . . . . .
F3 F 0.1364(3) 0.4349(2) -0.0727(3) 0.0735(9) Uani 1 1 d . . . . .
O1 O 0.3874(3) 0.6259(2) 0.6728(2) 0.0462(7) Uani 1 1 d . . . . .
O2 O 0.5795(2) 0.7094(2) 0.2501(2) 0.0426(7) Uani 1 1 d . . . . .
O3 O 0.2599(2) 0.78526(19) 0.2136(2) 0.0341(6) Uani 1 1 d . . . . .
O4 O 0.2243(2) 0.9266(2) 0.0194(3) 0.0435(7) Uani 1 1 d . . . . .
O5 O 0.3411(2) 0.63337(19) 0.0683(2) 0.0380(6) Uani 1 1 d . . . . .
O6 O 0.2062(4) 0.5322(3) 0.1646(3) 0.0691(10) Uani 1 1 d . . . . .
O7 O 0.1093(2) 0.6423(3) -0.0003(4) 0.0626(9) Uani 1 1 d . . . . .
C1 C 0.4067(3) 0.7105(3) 0.3636(3) 0.0332(8) Uani 1 1 d . . . . .
C2 C 0.4482(3) 0.6679(3) 0.4787(3) 0.0357(8) Uani 1 1 d . . . . .
H2 H 0.530846 0.642043 0.501263 0.043 Uiso 1 1 calc R U . . .
C3 C 0.3623(3) 0.6657(3) 0.5578(3) 0.0375(8) Uani 1 1 d . . . . .
C4 C 0.2410(3) 0.7052(3) 0.5236(3) 0.0413(9) Uani 1 1 d . . . . .
H4 H 0.185156 0.704046 0.580682 0.050 Uiso 1 1 calc R U . . .
C5 C 0.2005(3) 0.7455(3) 0.4095(4) 0.0382(8) Uani 1 1 d . . . . .
H5 H 0.117952 0.771382 0.386389 0.046 Uiso 1 1 calc R U . . .
C6 C 0.2864(3) 0.7465(3) 0.3303(3) 0.0328(8) Uani 1 1 d . . . . .
C7 C 0.4734(3) 0.7282(3) 0.2625(3) 0.0332(8) Uani 1 1 d . . . . .
C8 C 0.3776(3) 0.7856(3) 0.1655(3) 0.0328(8) Uani 1 1 d . . . . .
C9 C 0.4271(3) 0.8852(3) 0.1642(3) 0.0354(8) Uani 1 1 d . . . . .
H9A H 0.512225 0.882329 0.142534 0.042 Uiso 1 1 calc R U . . .
H9B H 0.437622 0.910834 0.248754 0.042 Uiso 1 1 calc R U . . .
C10 C 0.3485(3) 0.9550(3) 0.0786(3) 0.0400(9) Uani 1 1 d . . . . .
H10 H 0.356305 1.022801 0.105929 0.048 Uiso 1 1 calc R U . . .
C11 C 0.3196(3) 0.9409(3) -0.0546(3) 0.0402(9) Uani 1 1 d . . . . .
H11 H 0.309845 1.001092 -0.103429 0.048 Uiso 1 1 calc R U . . .
C12 C 0.3627(3) 0.8577(3) -0.1200(3) 0.0408(9) Uani 1 1 d . . . . .
H12A H 0.452670 0.868274 -0.124722 0.049 Uiso 1 1 calc R U . . .
H12B H 0.314427 0.858221 -0.205309 0.049 Uiso 1 1 calc R U . . .
C13 C 0.3519(3) 0.7603(3) -0.0691(3) 0.0379(8) Uani 1 1 d . . . . .
H13 H 0.342466 0.710371 -0.127835 0.046 Uiso 1 1 calc R U . . .
C14 C 0.3537(3) 0.7333(3) 0.0461(3) 0.0312(7) Uani 1 1 d . . . . .
C15 C 0.2313(4) 0.4951(3) -0.0575(4) 0.0519(10) Uani 1 1 d . . . . .
C16 C 0.4939(4) 0.5643(3) 0.7003(4) 0.0470(10) Uani 1 1 d . . . . .
H16A H 0.496310 0.535158 0.780992 0.070 Uiso 1 1 calc R U . . .
H16B H 0.571576 0.600946 0.701211 0.070 Uiso 1 1 calc R U . . .
H16C H 0.487191 0.514577 0.637554 0.070 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O5 1.567(3) . ?
S1 O6 1.415(3) . ?
S1 O7 1.403(3) . ?
S1 C15 1.813(5) . ?
F1 C15 1.318(6) . ?
F2 C15 1.321(5) . ?
F3 C15 1.313(5) . ?
O1 C3 1.372(4) . ?
O1 C16 1.424(5) . ?
O2 C7 1.204(4) . ?
O3 C6 1.383(4) . ?
O3 C8 1.463(4) . ?
O4 C10 1.431(5) . ?
O4 C11 1.441(4) . ?
O5 C14 1.439(4) . ?
C1 C2 1.405(5) . ?
C1 C6 1.375(5) . ?
C1 C7 1.460(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(5) . ?
C3 C4 1.404(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(5) . ?
C7 C8 1.569(5) . ?
C8 C9 1.501(5) . ?
C8 C14 1.494(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.510(5) . ?
C10 H10 1.0000 . ?
C10 C11 1.464(5) . ?
C11 H11 1.0000 . ?
C11 C12 1.495(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.495(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.329(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
O5 S1 C15 97.83(17) . . ?
O6 S1 O5 108.35(18) . . ?
O6 S1 C15 105.3(2) . . ?
O7 S1 O5 112.54(17) . . ?
O7 S1 O6 122.8(2) . . ?
O7 S1 C15 106.8(2) . . ?
C3 O1 C16 117.2(3) . . ?
C6 O3 C8 107.5(2) . . ?
C10 O4 C11 61.3(2) . . ?
C14 O5 S1 122.3(2) . . ?
C2 C1 C7 130.6(3) . . ?
C6 C1 C2 121.7(3) . . ?
C6 C1 C7 107.7(3) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 C1 116.5(3) . . ?
C3 C2 H2 121.7 . . ?
O1 C3 C2 123.9(3) . . ?
O1 C3 C4 115.1(3) . . ?
C2 C3 C4 121.1(3) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 C3 121.9(3) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 H5 121.6 . . ?
C4 C5 C6 116.7(3) . . ?
C6 C5 H5 121.6 . . ?
O3 C6 C5 123.3(3) . . ?
C1 C6 O3 114.6(3) . . ?
C1 C6 C5 122.1(3) . . ?
O2 C7 C1 131.5(3) . . ?
O2 C7 C8 123.4(3) . . ?
C1 C7 C8 105.0(3) . . ?
O3 C8 C7 104.6(2) . . ?
O3 C8 C9 109.8(3) . . ?
O3 C8 C14 107.7(3) . . ?
C9 C8 C7 107.4(3) . . ?
C14 C8 C7 109.6(3) . . ?
C14 C8 C9 117.1(3) . . ?
C8 C9 H9A 108.0 . . ?
C8 C9 H9B 108.0 . . ?
C8 C9 C10 117.1(3) . . ?
H9A C9 H9B 107.3 . . ?
C10 C9 H9A 108.0 . . ?
C10 C9 H9B 108.0 . . ?
O4 C10 C9 118.2(3) . . ?
O4 C10 H10 115.1 . . ?
O4 C10 C11 59.7(2) . . ?
C9 C10 H10 115.1 . . ?
C11 C10 C9 122.3(3) . . ?
C11 C10 H10 115.1 . . ?
O4 C11 C10 59.0(2) . . ?
O4 C11 H11 114.3 . . ?
O4 C11 C12 118.9(3) . . ?
C10 C11 H11 114.3 . . ?
C10 C11 C12 124.6(3) . . ?
C12 C11 H11 114.3 . . ?
C11 C12 H12A 107.6 . . ?
C11 C12 H12B 107.6 . . ?
C11 C12 C13 118.9(3) . . ?
H12A C12 H12B 107.0 . . ?
C13 C12 H12A 107.6 . . ?
C13 C12 H12B 107.6 . . ?
C12 C13 H13 115.2 . . ?
C14 C13 C12 129.5(3) . . ?
C14 C13 H13 115.2 . . ?
O5 C14 C8 109.7(3) . . ?
C13 C14 O5 117.3(3) . . ?
C13 C14 C8 132.8(4) . . ?
F1 C15 S1 111.6(3) . . ?
F1 C15 F2 107.9(4) . . ?
F2 C15 S1 110.0(3) . . ?
F3 C15 S1 109.5(3) . . ?
F3 C15 F1 108.9(4) . . ?
F3 C15 F2 108.9(4) . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
S1 O5 C14 C8 99.0(3) . . . . ?
S1 O5 C14 C13 -85.8(3) . . . . ?
O1 C3 C4 C5 -178.3(4) . . . . ?
O2 C7 C8 O3 176.0(4) . . . . ?
O2 C7 C8 C9 -67.4(4) . . . . ?
O2 C7 C8 C14 60.8(5) . . . . ?
O3 C8 C9 C10 -65.7(4) . . . . ?
O3 C8 C14 O5 -71.6(3) . . . . ?
O3 C8 C14 C13 114.2(4) . . . . ?
O4 C10 C11 C12 -105.7(4) . . . . ?
O4 C11 C12 C13 -25.9(5) . . . . ?
O5 S1 C15 F1 51.3(3) . . . . ?
O5 S1 C15 F2 -68.4(3) . . . . ?
O5 S1 C15 F3 172.0(3) . . . . ?
O6 S1 O5 C14 -128.2(3) . . . . ?
O6 S1 C15 F1 -60.3(4) . . . . ?
O6 S1 C15 F2 -180.0(3) . . . . ?
O6 S1 C15 F3 60.4(4) . . . . ?
O7 S1 O5 C14 10.8(3) . . . . ?
O7 S1 C15 F1 167.7(3) . . . . ?
O7 S1 C15 F2 48.0(3) . . . . ?
O7 S1 C15 F3 -71.6(4) . . . . ?
C1 C2 C3 O1 179.3(3) . . . . ?
C1 C2 C3 C4 -0.7(6) . . . . ?
C1 C7 C8 O3 -6.7(4) . . . . ?
C1 C7 C8 C9 110.0(3) . . . . ?
C1 C7 C8 C14 -121.9(3) . . . . ?
C2 C1 C6 O3 -179.5(3) . . . . ?
C2 C1 C6 C5 2.0(6) . . . . ?
C2 C1 C7 O2 1.8(7) . . . . ?
C2 C1 C7 C8 -175.3(4) . . . . ?
C2 C3 C4 C5 1.7(6) . . . . ?
C3 C4 C5 C6 -0.9(6) . . . . ?
C4 C5 C6 O3 -179.4(3) . . . . ?
C4 C5 C6 C1 -0.9(6) . . . . ?
C6 O3 C8 C7 7.9(3) . . . . ?
C6 O3 C8 C9 -107.1(3) . . . . ?
C6 O3 C8 C14 124.4(3) . . . . ?
C6 C1 C2 C3 -1.1(5) . . . . ?
C6 C1 C7 O2 -179.9(4) . . . . ?
C6 C1 C7 C8 3.1(4) . . . . ?
C7 C1 C2 C3 177.0(4) . . . . ?
C7 C1 C6 O3 2.0(4) . . . . ?
C7 C1 C6 C5 -176.5(3) . . . . ?
C7 C8 C9 C10 -178.9(3) . . . . ?
C7 C8 C14 O5 41.6(3) . . . . ?
C7 C8 C14 C13 -132.6(4) . . . . ?
C8 O3 C6 C1 -6.6(4) . . . . ?
C8 O3 C6 C5 171.9(3) . . . . ?
C8 C9 C10 O4 9.5(5) . . . . ?
C8 C9 C10 C11 -60.6(5) . . . . ?
C9 C8 C14 O5 164.1(3) . . . . ?
C9 C8 C14 C13 -10.0(5) . . . . ?
C9 C10 C11 O4 106.1(4) . . . . ?
C9 C10 C11 C12 0.4(6) . . . . ?
C10 O4 C11 C12 115.2(4) . . . . ?
C10 C11 C12 C13 44.6(5) . . . . ?
C11 O4 C10 C9 -112.9(4) . . . . ?
C11 C12 C13 C14 -27.6(5) . . . . ?
C12 C13 C14 O5 180.0(3) . . . . ?
C12 C13 C14 C8 -6.2(6) . . . . ?
C14 C8 C9 C10 57.4(4) . . . . ?
C15 S1 O5 C14 122.7(3) . . . . ?
C16 O1 C3 C2 -15.6(5) . . . . ?
C16 O1 C3 C4 164.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.766
_oxdiff_exptl_absorpt_empirical_full_min 0.383
####################################################################### 
# 
# 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_a44
_database_code_depnum_ccdc_archive 'CCDC 2363817'
loop_
_audit_author_name
_audit_author_address
Rigaku
;Jinan University
China
;
_audit_update_record             
;
2024-06-19 deposited with the CCDC.	2024-09-09 downloaded from the CCDC.
;
_audit_creation_date             2024-05-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 O4'
_chemical_formula_sum            'C15 H14 O4'
_chemical_formula_weight         258.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.3842(8)
_cell_length_b                   9.3169(9)
_cell_length_c                   10.2980(11)
_cell_angle_alpha                71.253(10)
_cell_angle_beta                 70.522(10)
_cell_angle_gamma                76.976(9)
_cell_volume                     626.93(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1906
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.8090
_cell_measurement_theta_min      4.7380
_shelx_estimated_absorpt_T_max   0.908
_shelx_estimated_absorpt_T_min   0.866
_exptl_absorpt_coefficient_mu    0.821
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3925
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.951
_diffrn_reflns_theta_min         4.728
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00  27.00   1.00    1.00    --  -39.98  57.00  60.00   94
  2  ω     37.00 114.00   1.00    1.00    --   39.98  38.00 150.00   77
  3  ω     80.00 133.00   1.00    1.02    --  108.20  30.00  60.00   53
  4  ω     96.00 176.00   1.00    1.02    --  108.20  30.00  90.00   80
  5  ω    131.00 171.00   1.00    1.02    --  108.20 125.00   0.00   40
  6  ω    149.00 176.00   1.00    1.02    --  108.20 125.00 -90.00   27
  7  ω     99.00 124.00   1.00    1.02    --  108.20 125.00 -90.00   25
  8  ω     32.00 134.00   1.00    1.02    --  108.20 -30.00  60.00  102
  9  ω     81.00 122.00   1.00    1.02    --  108.20 -77.00  30.00   41
 10  ω     70.00 131.00   1.00    1.02    --  108.20 -61.00 -30.00   61
 11  ω     55.00 120.00   1.00    1.02    --  108.20 -30.00-120.00   65
 12  ω     49.00 107.00   1.00    1.02    --  108.20 -94.00   0.00   58
 13  ω     43.00 121.00   1.00    1.02    --  108.20-125.00-120.00   78
 14  ω     46.00  87.00   1.00    1.00    --   39.98-125.00-180.00   41
 15  ω     27.00  96.00   1.00    1.02    --  108.20 -94.00 -60.00   69
 16  ω     46.00 109.00   1.00    1.02    --  108.20 -30.00 150.00   63
 17  ω    -82.00 -31.00   1.00    1.00    --  -39.98 -38.00 150.00   51
 18  ω   -110.00  -9.00   1.00    1.00    --  -39.98 -77.00 -90.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0934584000
_diffrn_orient_matrix_UB_12      0.0942925000
_diffrn_orient_matrix_UB_13      0.1098774000
_diffrn_orient_matrix_UB_21      -0.2025367000
_diffrn_orient_matrix_UB_22      -0.0108971000
_diffrn_orient_matrix_UB_23      -0.0050396000
_diffrn_orient_matrix_UB_31      -0.0094219000
_diffrn_orient_matrix_UB_32      -0.1484081000
_diffrn_orient_matrix_UB_33      0.1225999000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2006
_reflns_number_total             2432
_reflns_odcompleteness_completeness 99.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2432
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.135
_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)+(0.0426P)²+0.3651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1315
_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 Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C2(H2), C13(H13), C12(H12)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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 0.9228(2) 0.87877(16) 0.41746(16) 0.0341(4) Uani 1 1 d . . . . .
O3 O 0.7147(2) 0.66721(18) 0.28703(17) 0.0394(4) Uani 1 1 d . . . . .
O4 O 0.2260(2) 0.75367(18) 0.81428(17) 0.0400(4) Uani 1 1 d . . . . .
O2 O 1.1462(2) 0.61035(18) 0.46174(17) 0.0419(4) Uani 1 1 d . . . . .
C5 C 0.6440(3) 0.7635(2) 0.4947(2) 0.0295(4) Uani 1 1 d . . . . .
C7 C 0.7548(3) 0.7284(2) 0.3599(2) 0.0306(4) Uani 1 1 d . . . . .
C1 C 0.3969(3) 0.7808(2) 0.7088(2) 0.0316(5) Uani 1 1 d . . . . .
C9 C 1.1051(3) 0.6498(2) 0.3506(2) 0.0323(5) Uani 1 1 d . . . . .
C6 C 0.4629(3) 0.7269(2) 0.5892(2) 0.0313(5) Uani 1 1 d . . . . .
H6 H 0.390927 0.668755 0.571683 0.038 Uiso 1 1 calc R U . . .
C14 C 1.0115(3) 0.8861(2) 0.1662(2) 0.0344(5) Uani 1 1 d . . . . .
H14A H 0.997278 0.833252 0.103631 0.041 Uiso 1 1 calc R U . . .
H14B H 0.925805 0.982116 0.156226 0.041 Uiso 1 1 calc R U . . .
C3 C 0.6823(3) 0.9092(2) 0.6381(2) 0.0333(5) Uani 1 1 d . . . . .
H3 H 0.752787 0.970208 0.653481 0.040 Uiso 1 1 calc R U . . .
C2 C 0.5055(3) 0.8721(2) 0.7322(2) 0.0341(5) Uani 1 1 d . . . . .
H2 H 0.456637 0.908188 0.813257 0.041 Uiso 1 1 calc R U . . .
C8 C 0.9507(3) 0.7890(2) 0.3204(2) 0.0323(5) Uani 1 1 d . . . . .
C13 C 1.2181(3) 0.9188(3) 0.1200(2) 0.0371(5) Uani 1 1 d . . . . .
H13 H 1.236906 1.020453 0.096333 0.045 Uiso 1 1 calc R U . . .
C4 C 0.7497(3) 0.8515(2) 0.5201(2) 0.0304(4) Uani 1 1 d . . . . .
C12 C 1.3752(3) 0.8158(3) 0.1099(2) 0.0374(5) Uani 1 1 d . . . . .
H12 H 1.492507 0.854219 0.080453 0.045 Uiso 1 1 calc R U . . .
C10 C 1.2015(3) 0.5751(2) 0.2310(2) 0.0356(5) Uani 1 1 d . . . . .
H10A H 1.115452 0.591601 0.172524 0.043 Uiso 1 1 calc R U . . .
H10B H 1.231925 0.465819 0.269422 0.043 Uiso 1 1 calc R U . . .
C11 C 1.3891(3) 0.6458(3) 0.1397(3) 0.0400(5) Uani 1 1 d . . . . .
H11A H 1.488858 0.598017 0.187874 0.048 Uiso 1 1 calc R U . . .
H11B H 1.431185 0.620407 0.049011 0.048 Uiso 1 1 calc R U . . .
C15 C 0.0986(3) 0.6787(3) 0.7883(3) 0.0498(6) Uani 1 1 d . . . . .
H15A H 0.067064 0.737104 0.701260 0.075 Uiso 1 1 calc R U . . .
H15B H -0.017959 0.669832 0.866336 0.075 Uiso 1 1 calc R U . . .
H15C H 0.160731 0.578557 0.779663 0.075 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.436(2) . ?
O1 C4 1.374(2) . ?
O3 C7 1.215(2) . ?
O4 C1 1.375(3) . ?
O4 C15 1.425(3) . ?
O2 C9 1.203(3) . ?
C5 C7 1.455(3) . ?
C5 C6 1.406(3) . ?
C5 C4 1.382(3) . ?
C7 C8 1.551(3) . ?
C1 C6 1.376(3) . ?
C1 C2 1.412(3) . ?
C9 C8 1.546(3) . ?
C9 C10 1.501(3) . ?
C6 H6 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C8 1.525(3) . ?
C14 C13 1.509(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.381(3) . ?
C3 C4 1.382(3) . ?
C2 H2 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.326(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.499(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.543(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C8 107.12(15) . . ?
C1 O4 C15 116.53(18) . . ?
C6 C5 C7 131.78(18) . . ?
C4 C5 C7 106.84(18) . . ?
C4 C5 C6 121.36(19) . . ?
O3 C7 C5 131.40(19) . . ?
O3 C7 C8 123.96(19) . . ?
C5 C7 C8 104.64(16) . . ?
O4 C1 C6 125.25(19) . . ?
O4 C1 C2 113.89(19) . . ?
C6 C1 C2 120.87(19) . . ?
O2 C9 C8 120.7(2) . . ?
O2 C9 C10 123.9(2) . . ?
C10 C9 C8 115.37(18) . . ?
C5 C6 H6 121.5 . . ?
C1 C6 C5 117.05(18) . . ?
C1 C6 H6 121.5 . . ?
H14A C14 H14B 107.8 . . ?
C8 C14 H14A 109.1 . . ?
C8 C14 H14B 109.1 . . ?
C13 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C13 C14 C8 112.63(18) . . ?
C2 C3 H3 121.5 . . ?
C2 C3 C4 116.91(19) . . ?
C4 C3 H3 121.5 . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.8(2) . . ?
C3 C2 H2 119.1 . . ?
O1 C8 C7 105.54(16) . . ?
O1 C8 C9 108.60(16) . . ?
O1 C8 C14 110.24(17) . . ?
C9 C8 C7 107.84(16) . . ?
C14 C8 C7 113.01(17) . . ?
C14 C8 C9 111.34(17) . . ?
C14 C13 H13 117.0 . . ?
C12 C13 C14 126.0(2) . . ?
C12 C13 H13 117.0 . . ?
O1 C4 C5 114.57(18) . . ?
O1 C4 C3 123.45(18) . . ?
C5 C4 C3 122.0(2) . . ?
C13 C12 H12 115.7 . . ?
C13 C12 C11 128.7(2) . . ?
C11 C12 H12 115.7 . . ?
C9 C10 H10A 110.0 . . ?
C9 C10 H10B 110.0 . . ?
C9 C10 C11 108.38(17) . . ?
H10A C10 H10B 108.4 . . ?
C11 C10 H10A 110.0 . . ?
C11 C10 H10B 110.0 . . ?
C12 C11 C10 116.06(18) . . ?
C12 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
C10 C11 H11A 108.3 . . ?
C10 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O3 C7 C8 O1 168.49(18) . . . . ?
O3 C7 C8 C9 -75.6(2) . . . . ?
O3 C7 C8 C14 47.9(3) . . . . ?
O4 C1 C6 C5 -178.47(18) . . . . ?
O4 C1 C2 C3 179.14(18) . . . . ?
O2 C9 C8 O1 17.9(3) . . . . ?
O2 C9 C8 C7 -96.0(2) . . . . ?
O2 C9 C8 C14 139.5(2) . . . . ?
O2 C9 C10 C11 -84.2(2) . . . . ?
C5 C7 C8 O1 -11.1(2) . . . . ?
C5 C7 C8 C9 104.88(18) . . . . ?
C5 C7 C8 C14 -131.61(18) . . . . ?
C7 C5 C6 C1 -179.1(2) . . . . ?
C7 C5 C4 O1 -0.8(2) . . . . ?
C7 C5 C4 C3 177.87(18) . . . . ?
C9 C10 C11 C12 -41.9(3) . . . . ?
C6 C5 C7 O3 6.2(4) . . . . ?
C6 C5 C7 C8 -174.3(2) . . . . ?
C6 C5 C4 O1 -179.40(17) . . . . ?
C6 C5 C4 C3 -0.8(3) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C14 C13 C12 C11 0.5(4) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
C2 C3 C4 O1 179.97(18) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C8 O1 C4 C5 -6.7(2) . . . . ?
C8 O1 C4 C3 174.69(19) . . . . ?
C8 C9 C10 C11 93.3(2) . . . . ?
C8 C14 C13 C12 63.6(3) . . . . ?
C13 C14 C8 O1 73.4(2) . . . . ?
C13 C14 C8 C7 -168.81(17) . . . . ?
C13 C14 C8 C9 -47.2(2) . . . . ?
C13 C12 C11 C10 -18.2(4) . . . . ?
C4 O1 C8 C7 10.7(2) . . . . ?
C4 O1 C8 C9 -104.71(18) . . . . ?
C4 O1 C8 C14 133.06(17) . . . . ?
C4 C5 C7 O3 -172.3(2) . . . . ?
C4 C5 C7 C8 7.3(2) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C4 C3 C2 C1 -0.6(3) . . . . ?
C10 C9 C8 O1 -159.76(17) . . . . ?
C10 C9 C8 C7 86.3(2) . . . . ?
C10 C9 C8 C14 -38.2(2) . . . . ?
C15 O4 C1 C6 -7.6(3) . . . . ?
C15 O4 C1 C2 172.38(19) . . . . ?

_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 1.352
_oxdiff_exptl_absorpt_empirical_full_min 0.599
####################################################################### 
# 
# 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_hxj-2-30-b1
_database_code_depnum_ccdc_archive 'CCDC 2363818'
loop_
_audit_author_name
_audit_author_address
Rigaku
;Jinan University
China
;
_audit_update_record             
;
2024-06-19 deposited with the CCDC.	2024-09-09 downloaded from the CCDC.
;
_audit_creation_date             2024-05-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 F3 O7 S'
_chemical_formula_sum            'C16 H13 F3 O7 S'
_chemical_formula_weight         406.32
_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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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                   10.8244(6)
_cell_length_b                   14.0485(7)
_cell_length_c                   11.0895(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.020(6)
_cell_angle_gamma                90
_cell_volume                     1655.24(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3498
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      29.0880
_cell_measurement_theta_min      2.7950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.04783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6755
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.367
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_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    -68.00  28.00   1.00    1.34    --  -11.27 -19.00  60.00   96
  2  ω    -75.00  13.00   1.00    1.34    --  -11.27 -38.00   0.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0628720000
_diffrn_orient_matrix_UB_12      -0.0169507000
_diffrn_orient_matrix_UB_13      0.0105083000
_diffrn_orient_matrix_UB_21      0.0048354000
_diffrn_orient_matrix_UB_22      0.0130772000
_diffrn_orient_matrix_UB_23      -0.0607485000
_diffrn_orient_matrix_UB_31      0.0219677000
_diffrn_orient_matrix_UB_32      0.0456869000
_diffrn_orient_matrix_UB_33      0.0212030000
_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              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2493
_reflns_number_total             2909
_reflns_odcompleteness_completeness 99.92
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2909
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.032
_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)+(0.0475P)²+0.4227P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0962
_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:
 C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C13(H13)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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
S1 S 0.93838(5) 0.57991(3) 0.78748(4) 0.02607(16) Uani 1 1 d . . . . .
F1 F 1.04121(17) 0.44501(10) 0.68050(16) 0.0722(5) Uani 1 1 d . . . . .
F2 F 1.07583(15) 0.43852(11) 0.87644(15) 0.0643(5) Uani 1 1 d . . . . .
F3 F 1.17223(13) 0.54084(12) 0.78542(16) 0.0695(5) Uani 1 1 d . . . . .
O1 O 0.75372(13) 0.71921(10) 0.41491(11) 0.0309(3) Uani 1 1 d . . . . .
O2 O 0.78747(12) 0.78232(9) 0.72937(11) 0.0225(3) Uani 1 1 d . . . . .
O3 O 1.03480(15) 1.00418(10) 0.64426(13) 0.0384(4) Uani 1 1 d . . . . .
O4 O 0.92757(12) 0.62640(8) 0.65743(11) 0.0247(3) Uani 1 1 d . . . . .
O5 O 0.83027(14) 0.52388(12) 0.78462(16) 0.0465(4) Uani 1 1 d . . . . .
O6 O 0.98290(17) 0.64386(10) 0.88308(13) 0.0462(4) Uani 1 1 d . . . . .
O7 O 0.32109(13) 0.62110(10) 0.59327(13) 0.0345(4) Uani 1 1 d . . . . .
C1 C 0.66866(17) 0.74460(12) 0.69948(17) 0.0207(4) Uani 1 1 d . . . . .
C2 C 0.58652(19) 0.73865(13) 0.78140(17) 0.0243(4) Uani 1 1 d . . . . .
H2 H 0.609129 0.762052 0.863020 0.029 Uiso 1 1 calc R U . . .
C3 C 0.47180(19) 0.69766(14) 0.73950(18) 0.0270(5) Uani 1 1 d . . . . .
H3 H 0.413332 0.693132 0.793149 0.032 Uiso 1 1 calc R U . . .
C4 C 0.43791(18) 0.66203(13) 0.61923(18) 0.0249(4) Uani 1 1 d . . . . .
C5 C 0.51839(18) 0.67004(13) 0.53757(17) 0.0230(4) Uani 1 1 d . . . . .
H5 H 0.495436 0.647540 0.455560 0.028 Uiso 1 1 calc R U . . .
C6 C 0.63563(17) 0.71276(12) 0.58029(16) 0.0203(4) Uani 1 1 d . . . . .
C7 C 0.74005(18) 0.73371(13) 0.51918(16) 0.0214(4) Uani 1 1 d . . . . .
C8 C 0.84076(17) 0.78279(13) 0.61788(16) 0.0202(4) Uani 1 1 d . . . . .
C9 C 0.85917(19) 0.88599(13) 0.58193(17) 0.0251(4) Uani 1 1 d . . . . .
H9A H 0.894420 0.887165 0.505882 0.030 Uiso 1 1 calc R U . . .
H9B H 0.776447 0.918379 0.564505 0.030 Uiso 1 1 calc R U . . .
C10 C 0.9459(2) 0.93920(13) 0.68158(19) 0.0277(5) Uani 1 1 d . . . . .
H10 H 0.909920 0.958578 0.754475 0.033 Uiso 1 1 calc R U . . .
C11 C 1.0805(2) 0.91780(13) 0.70469(19) 0.0297(5) Uani 1 1 d . . . . .
H11 H 1.125961 0.923995 0.791745 0.036 Uiso 1 1 calc R U . . .
C12 C 1.1296(2) 0.84394(14) 0.6287(2) 0.0316(5) Uani 1 1 d . . . . .
H12A H 1.222547 0.841676 0.652353 0.038 Uiso 1 1 calc R U . . .
H12B H 1.108035 0.862609 0.541155 0.038 Uiso 1 1 calc R U . . .
C13 C 1.07732(19) 0.74616(14) 0.64364(18) 0.0261(5) Uani 1 1 d . . . . .
H13 H 1.135524 0.694829 0.655291 0.031 Uiso 1 1 calc R U . . .
C14 C 0.95896(18) 0.72534(12) 0.64202(16) 0.0199(4) Uani 1 1 d . . . . .
C15 C 1.0653(2) 0.49672(16) 0.7818(2) 0.0415(6) Uani 1 1 d . . . . .
C16 C 0.2898(2) 0.56684(16) 0.48344(19) 0.0339(5) Uani 1 1 d . . . . .
H16A H 0.285226 0.608964 0.412278 0.051 Uiso 1 1 calc R U . . .
H16B H 0.208160 0.535872 0.480360 0.051 Uiso 1 1 calc R U . . .
H16C H 0.354546 0.518301 0.481985 0.051 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O4 1.5671(13) . ?
S1 O5 1.4056(15) . ?
S1 O6 1.4029(15) . ?
S1 C15 1.814(2) . ?
F1 C15 1.321(3) . ?
F2 C15 1.318(3) . ?
F3 C15 1.306(3) . ?
O1 C7 1.211(2) . ?
O2 C1 1.372(2) . ?
O2 C8 1.461(2) . ?
O3 C10 1.443(2) . ?
O3 C11 1.428(2) . ?
O4 C14 1.449(2) . ?
O7 C4 1.369(2) . ?
O7 C16 1.422(2) . ?
C1 C2 1.390(3) . ?
C1 C6 1.376(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.367(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.406(3) . ?
C4 C5 1.376(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.402(3) . ?
C6 C7 1.455(3) . ?
C7 C8 1.551(3) . ?
C8 C9 1.527(3) . ?
C8 C14 1.493(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.505(3) . ?
C10 H10 1.0000 . ?
C10 C11 1.461(3) . ?
C11 H11 1.0000 . ?
C11 C12 1.497(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.507(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.311(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
O4 S1 C15 99.22(9) . . ?
O5 S1 O4 107.29(9) . . ?
O5 S1 C15 105.75(11) . . ?
O6 S1 O4 112.52(8) . . ?
O6 S1 O5 122.68(11) . . ?
O6 S1 C15 106.60(11) . . ?
C1 O2 C8 107.51(13) . . ?
C11 O3 C10 61.18(13) . . ?
C14 O4 S1 122.04(11) . . ?
C4 O7 C16 117.68(15) . . ?
O2 C1 C2 123.55(17) . . ?
O2 C1 C6 114.65(16) . . ?
C6 C1 C2 121.80(18) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 C1 117.14(18) . . ?
C3 C2 H2 121.4 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.85(18) . . ?
C4 C3 H3 119.1 . . ?
O7 C4 C3 114.34(16) . . ?
O7 C4 C5 124.87(17) . . ?
C5 C4 C3 120.79(18) . . ?
C4 C5 H5 121.3 . . ?
C4 C5 C6 117.31(17) . . ?
C6 C5 H5 121.3 . . ?
C1 C6 C5 121.06(17) . . ?
C1 C6 C7 107.41(16) . . ?
C5 C6 C7 131.53(17) . . ?
O1 C7 C6 131.19(17) . . ?
O1 C7 C8 123.44(17) . . ?
C6 C7 C8 105.37(15) . . ?
O2 C8 C7 104.91(14) . . ?
O2 C8 C9 108.53(14) . . ?
O2 C8 C14 108.02(14) . . ?
C9 C8 C7 110.31(14) . . ?
C14 C8 C7 110.42(14) . . ?
C14 C8 C9 114.20(16) . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C8 111.97(15) . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
O3 C10 C9 117.40(16) . . ?
O3 C10 H10 116.3 . . ?
O3 C10 C11 58.91(13) . . ?
C9 C10 H10 116.3 . . ?
C11 C10 C9 119.20(17) . . ?
C11 C10 H10 116.3 . . ?
O3 C11 C10 59.91(13) . . ?
O3 C11 H11 116.2 . . ?
O3 C11 C12 116.97(17) . . ?
C10 C11 H11 116.2 . . ?
C10 C11 C12 119.57(17) . . ?
C12 C11 H11 116.2 . . ?
C11 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C11 C12 C13 112.88(17) . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C12 C13 H13 117.0 . . ?
C14 C13 C12 126.06(18) . . ?
C14 C13 H13 117.0 . . ?
O4 C14 C8 109.12(15) . . ?
C13 C14 O4 117.58(16) . . ?
C13 C14 C8 133.13(17) . . ?
F1 C15 S1 110.84(16) . . ?
F2 C15 S1 108.81(17) . . ?
F2 C15 F1 107.99(19) . . ?
F3 C15 S1 111.45(16) . . ?
F3 C15 F1 108.5(2) . . ?
F3 C15 F2 109.20(19) . . ?
O7 C16 H16A 109.5 . . ?
O7 C16 H16B 109.5 . . ?
O7 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
S1 O4 C14 C8 -99.13(15) . . . . ?
S1 O4 C14 C13 84.96(19) . . . . ?
O1 C7 C8 O2 -177.99(17) . . . . ?
O1 C7 C8 C9 65.3(2) . . . . ?
O1 C7 C8 C14 -61.8(2) . . . . ?
O2 C1 C2 C3 -178.80(16) . . . . ?
O2 C1 C6 C5 178.21(15) . . . . ?
O2 C1 C6 C7 -2.4(2) . . . . ?
O2 C8 C9 C10 59.5(2) . . . . ?
O2 C8 C14 O4 67.42(17) . . . . ?
O2 C8 C14 C13 -117.5(2) . . . . ?
O3 C10 C11 C12 -105.9(2) . . . . ?
O3 C11 C12 C13 -131.67(19) . . . . ?
O4 S1 C15 F1 -51.19(17) . . . . ?
O4 S1 C15 F2 -169.79(16) . . . . ?
O4 S1 C15 F3 69.74(18) . . . . ?
O5 S1 O4 C14 136.79(14) . . . . ?
O5 S1 C15 F1 59.83(19) . . . . ?
O5 S1 C15 F2 -58.77(19) . . . . ?
O5 S1 C15 F3 -179.25(16) . . . . ?
O6 S1 O4 C14 -1.05(17) . . . . ?
O6 S1 C15 F1 -168.14(15) . . . . ?
O6 S1 C15 F2 73.25(18) . . . . ?
O6 S1 C15 F3 -47.22(19) . . . . ?
O7 C4 C5 C6 -179.00(17) . . . . ?
C1 O2 C8 C7 -3.66(17) . . . . ?
C1 O2 C8 C9 114.24(15) . . . . ?
C1 O2 C8 C14 -121.45(14) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C1 C6 C7 O1 -179.8(2) . . . . ?
C1 C6 C7 C8 -0.08(18) . . . . ?
C2 C1 C6 C5 -2.0(3) . . . . ?
C2 C1 C6 C7 177.34(17) . . . . ?
C2 C3 C4 O7 178.36(17) . . . . ?
C2 C3 C4 C5 -2.1(3) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C4 C5 C6 C7 -178.71(18) . . . . ?
C5 C6 C7 O1 -0.5(3) . . . . ?
C5 C6 C7 C8 179.18(18) . . . . ?
C6 C1 C2 C3 1.4(3) . . . . ?
C6 C7 C8 O2 2.28(17) . . . . ?
C6 C7 C8 C9 -114.41(16) . . . . ?
C6 C7 C8 C14 118.42(16) . . . . ?
C7 C8 C9 C10 173.93(16) . . . . ?
C7 C8 C14 O4 -46.76(18) . . . . ?
C7 C8 C14 C13 128.3(2) . . . . ?
C8 O2 C1 C2 -175.79(16) . . . . ?
C8 O2 C1 C6 3.99(19) . . . . ?
C8 C9 C10 O3 140.02(17) . . . . ?
C8 C9 C10 C11 72.1(2) . . . . ?
C9 C8 C14 O4 -171.74(14) . . . . ?
C9 C8 C14 C13 3.3(3) . . . . ?
C9 C10 C11 O3 106.18(19) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 O3 C11 C12 110.2(2) . . . . ?
C10 C11 C12 C13 -62.7(2) . . . . ?
C11 O3 C10 C9 -109.21(19) . . . . ?
C11 C12 C13 C14 45.9(3) . . . . ?
C12 C13 C14 O4 179.69(17) . . . . ?
C12 C13 C14 C8 5.0(3) . . . . ?
C14 C8 C9 C10 -61.0(2) . . . . ?
C15 S1 O4 C14 -113.43(15) . . . . ?
C16 O7 C4 C3 -167.68(17) . . . . ?
C16 O7 C4 C5 12.8(3) . . . . ?

_olex2_date_sample_data_collection 2022-12-15
_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 17.419
_oxdiff_exptl_absorpt_empirical_full_min 0.696
####################################################################### 
# 
# 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_hyj-2-188-b2
_database_code_depnum_ccdc_archive 'CCDC 2363820'
loop_
_audit_author_name
_audit_author_address
Rigaku
;Jinan University
China
;
_audit_update_record             
;
2024-06-19 deposited with the CCDC.	2024-09-09 downloaded from the CCDC.
;
_audit_creation_date             2024-05-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H18 O6'
_chemical_formula_sum            'C17 H18 O6'
_chemical_formula_weight         318.31
_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'
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                   8.5810(6)
_cell_length_b                   7.0851(5)
_cell_length_c                   24.335(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.198(8)
_cell_angle_gamma                90
_cell_volume                     1467.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2867
_cell_measurement_temperature    150.01(14)
_cell_measurement_theta_max      29.3380
_cell_measurement_theta_min      2.7400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5629
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.392
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  50.00   1.00    3.26    --  -11.27  77.00  30.00   94
  2  ω     -7.00  69.00   1.00    3.26    --   11.90  77.00 -60.00   76
  3  ω     -2.00  38.00   1.00    8.00    --   11.90  57.00 -90.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0062735000
_diffrn_orient_matrix_UB_12      0.0997885000
_diffrn_orient_matrix_UB_13      0.0001753000
_diffrn_orient_matrix_UB_21      0.0281070000
_diffrn_orient_matrix_UB_22      -0.0021968000
_diffrn_orient_matrix_UB_23      0.0286728000
_diffrn_orient_matrix_UB_31      0.0781988000
_diffrn_orient_matrix_UB_32      -0.0071302000
_diffrn_orient_matrix_UB_33      -0.0064192000
_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              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2129
_reflns_number_total             2572
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2572
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0539
_refine_ls_restrained_S_all      1.055
_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)+(0.0775P)²+0.0061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1438
_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:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
;
_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
O1 O 0.51256(16) 1.0239(2) 0.62665(6) 0.0318(4) Uani 1 1 d . . . . .
O2 O 0.66997(14) 0.89808(18) 0.56958(6) 0.0251(4) Uani 1 1 d . . . . .
O3 O 0.09133(15) 0.3023(2) 0.60828(7) 0.0328(4) Uani 1 1 d . . . . .
O4 O 0.39641(13) 0.61983(18) 0.65436(5) 0.0186(3) Uani 1 1 d . . . . .
O5 O 0.65426(14) 0.46013(18) 0.56039(6) 0.0217(4) Uani 1 1 d . . . . .
O6 O 0.96342(15) 0.4532(2) 0.77518(6) 0.0304(4) Uani 1 1 d . . . . .
C1 C 0.4108(2) 0.7745(3) 0.56439(8) 0.0180(4) Uani 1 1 d . . . . .
H1 H 0.436142 0.746678 0.526205 0.022 Uiso 1 1 calc R U . . .
C2 C 0.2497(2) 0.8716(3) 0.55858(9) 0.0219(5) Uani 1 1 d . . . . .
H2A H 0.229575 0.915522 0.595665 0.026 Uiso 1 1 calc R U . . .
H2B H 0.254387 0.984729 0.534946 0.026 Uiso 1 1 calc R U . . .
C3 C 0.1119(2) 0.7511(3) 0.53428(9) 0.0233(5) Uani 1 1 d . . . . .
H3A H 0.143414 0.677358 0.502912 0.028 Uiso 1 1 calc R U . . .
H3B H 0.024373 0.834993 0.519448 0.028 Uiso 1 1 calc R U . . .
C4 C 0.0534(2) 0.6152(3) 0.57584(9) 0.0255(5) Uani 1 1 d . . . . .
H4A H 0.050151 0.683935 0.611107 0.031 Uiso 1 1 calc R U . . .
H4B H -0.055808 0.578921 0.561846 0.031 Uiso 1 1 calc R U . . .
C5 C 0.1469(2) 0.4385(3) 0.58805(8) 0.0208(5) Uani 1 1 d . . . . .
C6 C 0.3139(2) 0.4273(3) 0.57369(9) 0.0194(5) Uani 1 1 d . . . . .
H6A H 0.310021 0.427607 0.532858 0.023 Uiso 1 1 calc R U . . .
H6B H 0.359914 0.305310 0.587329 0.023 Uiso 1 1 calc R U . . .
C7 C 0.4237(2) 0.5865(3) 0.59730(8) 0.0178(4) Uani 1 1 d . . . . .
C8 C 0.5930(2) 0.5119(2) 0.60059(9) 0.0174(5) Uani 1 1 d . . . . .
C9 C 0.6530(2) 0.5138(2) 0.65867(8) 0.0175(4) Uani 1 1 d . . . . .
C10 C 0.5329(2) 0.5748(2) 0.68761(8) 0.0171(5) Uani 1 1 d . . . . .
C11 C 0.5519(2) 0.5864(3) 0.74489(8) 0.0205(5) Uani 1 1 d . . . . .
H11 H 0.468498 0.624394 0.764649 0.025 Uiso 1 1 calc R U . . .
C12 C 0.6982(2) 0.5399(3) 0.77187(9) 0.0239(5) Uani 1 1 d . . . . .
H12 H 0.715440 0.545598 0.811168 0.029 Uiso 1 1 calc R U . . .
C13 C 0.8229(2) 0.4842(3) 0.74270(8) 0.0210(5) Uani 1 1 d . . . . .
C14 C 0.8017(2) 0.4668(3) 0.68629(9) 0.0202(5) Uani 1 1 d . . . . .
H14 H 0.883994 0.424616 0.666597 0.024 Uiso 1 1 calc R U . . .
C15 C 1.0995(2) 0.4500(3) 0.74655(9) 0.0312(6) Uani 1 1 d . . . . .
H15A H 1.090411 0.345974 0.719795 0.047 Uiso 1 1 calc R U . . .
H15B H 1.193619 0.431926 0.773292 0.047 Uiso 1 1 calc R U . . .
H15C H 1.107515 0.569817 0.726996 0.047 Uiso 1 1 calc R U . . .
C16 C 0.5334(2) 0.9129(3) 0.59087(9) 0.0187(5) Uani 1 1 d . . . . .
C17 C 0.7951(2) 1.0203(3) 0.59473(9) 0.0275(5) Uani 1 1 d . . . . .
H17A H 0.886293 1.009065 0.574387 0.041 Uiso 1 1 calc R U . . .
H17B H 0.825027 0.982803 0.633380 0.041 Uiso 1 1 calc R U . . .
H17C H 0.758466 1.151403 0.593387 0.041 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C16 1.204(2) . ?
O2 C16 1.343(2) . ?
O2 C17 1.454(2) . ?
O3 C5 1.209(2) . ?
O4 C7 1.456(2) . ?
O4 C10 1.375(2) . ?
O5 C8 1.223(2) . ?
O6 C13 1.374(2) . ?
O6 C15 1.433(2) . ?
C1 H1 1.0000 . ?
C1 C2 1.535(2) . ?
C1 C7 1.551(3) . ?
C1 C16 1.521(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.518(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.526(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.497(3) . ?
C5 C6 1.519(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.534(3) . ?
C7 C8 1.539(2) . ?
C8 C9 1.442(3) . ?
C9 C10 1.388(3) . ?
C9 C14 1.406(3) . ?
C10 C11 1.386(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.412(3) . ?
C13 C14 1.368(3) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O2 C17 115.17(15) . . ?
C10 O4 C7 107.27(13) . . ?
C13 O6 C15 115.65(16) . . ?
C2 C1 H1 107.5 . . ?
C2 C1 C7 115.97(15) . . ?
C7 C1 H1 107.5 . . ?
C16 C1 H1 107.5 . . ?
C16 C1 C2 108.48(15) . . ?
C16 C1 C7 109.50(16) . . ?
C1 C2 H2A 108.4 . . ?
C1 C2 H2B 108.4 . . ?
H2A C2 H2B 107.4 . . ?
C3 C2 C1 115.61(15) . . ?
C3 C2 H2A 108.4 . . ?
C3 C2 H2B 108.4 . . ?
C2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C2 C3 C4 113.69(17) . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C3 C4 H4A 108.2 . . ?
C3 C4 H4B 108.2 . . ?
H4A C4 H4B 107.3 . . ?
C5 C4 C3 116.49(15) . . ?
C5 C4 H4A 108.2 . . ?
C5 C4 H4B 108.2 . . ?
O3 C5 C4 121.30(16) . . ?
O3 C5 C6 118.95(17) . . ?
C4 C5 C6 119.74(17) . . ?
C5 C6 H6A 108.4 . . ?
C5 C6 H6B 108.4 . . ?
C5 C6 C7 115.33(15) . . ?
H6A C6 H6B 107.5 . . ?
C7 C6 H6A 108.4 . . ?
C7 C6 H6B 108.4 . . ?
O4 C7 C1 110.11(15) . . ?
O4 C7 C6 108.18(14) . . ?
O4 C7 C8 105.64(15) . . ?
C6 C7 C1 115.93(16) . . ?
C6 C7 C8 107.34(14) . . ?
C8 C7 C1 109.13(15) . . ?
O5 C8 C7 123.99(18) . . ?
O5 C8 C9 130.52(17) . . ?
C9 C8 C7 105.47(16) . . ?
C10 C9 C8 107.66(16) . . ?
C10 C9 C14 121.23(19) . . ?
C14 C9 C8 131.11(18) . . ?
O4 C10 C9 113.92(17) . . ?
O4 C10 C11 124.26(16) . . ?
C11 C10 C9 121.82(17) . . ?
C10 C11 H11 121.6 . . ?
C12 C11 C10 116.73(18) . . ?
C12 C11 H11 121.6 . . ?
C11 C12 H12 119.1 . . ?
C11 C12 C13 121.9(2) . . ?
C13 C12 H12 119.1 . . ?
O6 C13 C12 114.90(18) . . ?
C14 C13 O6 124.03(17) . . ?
C14 C13 C12 121.06(18) . . ?
C9 C14 H14 121.4 . . ?
C13 C14 C9 117.20(18) . . ?
C13 C14 H14 121.4 . . ?
O6 C15 H15A 109.5 . . ?
O6 C15 H15B 109.5 . . ?
O6 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C16 O2 123.09(17) . . ?
O1 C16 C1 124.77(16) . . ?
O2 C16 C1 112.14(16) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O3 C5 C6 C7 -127.6(2) . . . . ?
O4 C7 C8 O5 176.46(15) . . . . ?
O4 C7 C8 C9 -2.00(18) . . . . ?
O4 C10 C11 C12 -178.53(16) . . . . ?
O5 C8 C9 C10 -176.16(18) . . . . ?
O5 C8 C9 C14 3.9(3) . . . . ?
O6 C13 C14 C9 -176.44(16) . . . . ?
C1 C2 C3 C4 79.5(2) . . . . ?
C1 C7 C8 O5 -65.2(2) . . . . ?
C1 C7 C8 C9 116.36(17) . . . . ?
C2 C1 C7 O4 -62.8(2) . . . . ?
C2 C1 C7 C6 60.4(2) . . . . ?
C2 C1 C7 C8 -178.31(16) . . . . ?
C2 C1 C16 O1 37.1(3) . . . . ?
C2 C1 C16 O2 -142.72(16) . . . . ?
C2 C3 C4 C5 -78.9(2) . . . . ?
C3 C4 C5 O3 -160.63(19) . . . . ?
C3 C4 C5 C6 18.0(3) . . . . ?
C4 C5 C6 C7 53.7(3) . . . . ?
C5 C6 C7 O4 42.8(2) . . . . ?
C5 C6 C7 C1 -81.4(2) . . . . ?
C5 C6 C7 C8 156.35(17) . . . . ?
C6 C7 C8 O5 61.2(2) . . . . ?
C6 C7 C8 C9 -117.26(17) . . . . ?
C7 O4 C10 C9 0.3(2) . . . . ?
C7 O4 C10 C11 -179.25(16) . . . . ?
C7 C1 C2 C3 -54.6(2) . . . . ?
C7 C1 C16 O1 -90.4(2) . . . . ?
C7 C1 C16 O2 89.82(19) . . . . ?
C7 C8 C9 C10 2.16(19) . . . . ?
C7 C8 C9 C14 -177.79(18) . . . . ?
C8 C9 C10 O4 -1.6(2) . . . . ?
C8 C9 C10 C11 177.92(17) . . . . ?
C8 C9 C14 C13 179.75(18) . . . . ?
C9 C10 C11 C12 2.0(3) . . . . ?
C10 O4 C7 C1 -116.60(15) . . . . ?
C10 O4 C7 C6 115.79(15) . . . . ?
C10 O4 C7 C8 1.11(18) . . . . ?
C10 C9 C14 C13 -0.2(3) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C11 C12 C13 O6 176.38(17) . . . . ?
C11 C12 C13 C14 -2.6(3) . . . . ?
C12 C13 C14 C9 2.5(3) . . . . ?
C14 C9 C10 O4 178.35(16) . . . . ?
C14 C9 C10 C11 -2.1(3) . . . . ?
C15 O6 C13 C12 -162.87(18) . . . . ?
C15 O6 C13 C14 16.1(3) . . . . ?
C16 C1 C2 C3 -178.26(17) . . . . ?
C16 C1 C7 O4 60.34(19) . . . . ?
C16 C1 C7 C6 -176.47(15) . . . . ?
C16 C1 C7 C8 -55.2(2) . . . . ?
C17 O2 C16 O1 2.9(3) . . . . ?
C17 O2 C16 C1 -177.31(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 8.785
_oxdiff_exptl_absorpt_empirical_full_min 0.471
