# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_r20211207c
_database_code_depnum_ccdc_archive 'CCDC 2132379'
loop_
_audit_author_name
_audit_author_address
'Yunxia Li'
;Taiyuan University of Technology
China
;
_audit_update_record             
;
2022-01-04 deposited with the CCDC.	2022-07-08 downloaded from the CCDC.
;
_audit_creation_date             2021-12-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H14 O5'
_chemical_formula_sum            'C13 H14 O5'
_chemical_formula_weight         250.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      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                   8.4627(5)
_cell_length_b                   8.5873(4)
_cell_length_c                   9.3807(7)
_cell_angle_alpha                79.025(5)
_cell_angle_beta                 66.995(6)
_cell_angle_gamma                77.883(5)
_cell_volume                     609.05(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5307
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.8490
_cell_measurement_theta_min      2.3570
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.896
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9172
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.909
_diffrn_reflns_theta_min         2.376
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0270801000
_diffrn_orient_matrix_UB_12      -0.0156394000
_diffrn_orient_matrix_UB_13      -0.0578646000
_diffrn_orient_matrix_UB_21      -0.0727021000
_diffrn_orient_matrix_UB_22      -0.0310362000
_diffrn_orient_matrix_UB_23      0.0591418000
_diffrn_orient_matrix_UB_31      -0.0496301000
_diffrn_orient_matrix_UB_32      0.0776795000
_diffrn_orient_matrix_UB_33      0.0010657000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3072
_reflns_number_total             4079
_reflns_odcompleteness_completeness 99.76
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.339
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.052(11)
_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   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         4079
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.045
_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)+(0.0629P)²+0.0802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1370
_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:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C)
;
_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 0.99355(10) -0.00541(10) 0.18270(9) 0.0292(2) Uani 1 1 d . . . . .
O2 O 0.34606(11) 0.54493(10) 0.27262(10) 0.0327(2) Uani 1 1 d . . . . .
O3 O 0.29181(10) 0.42966(9) 0.52202(9) 0.02618(19) Uani 1 1 d . . . . .
O4 O -0.15404(11) 0.76600(10) 0.66780(9) 0.0321(2) Uani 1 1 d . . . . .
O5 O -0.18265(10) 0.66895(10) 0.91538(9) 0.0286(2) Uani 1 1 d . . . . .
C1 C 1.04212(17) -0.12517(15) 0.29326(14) 0.0331(3) Uani 1 1 d . . . . .
H1A H 1.151492 -0.191352 0.238877 0.050 Uiso 1 1 calc GR . . . .
H1B H 0.951024 -0.193111 0.346070 0.050 Uiso 1 1 calc GR . . . .
H1C H 1.057081 -0.072984 0.370459 0.050 Uiso 1 1 calc GR . . . .
C2 C 0.84287(14) 0.09576(12) 0.23727(12) 0.0225(2) Uani 1 1 d . . . . .
C3 C 0.80557(14) 0.21458(13) 0.12539(12) 0.0245(2) Uani 1 1 d . . . . .
H3 H 0.882952 0.218969 0.019658 0.029 Uiso 1 1 calc R . . . .
C4 C 0.65715(14) 0.32489(13) 0.16832(12) 0.0236(2) Uani 1 1 d . . . . .
H4 H 0.632290 0.405441 0.092070 0.028 Uiso 1 1 calc R . . . .
C5 C 0.54218(13) 0.31917(12) 0.32411(12) 0.0219(2) Uani 1 1 d . . . . .
C6 C 0.57972(14) 0.19954(13) 0.43393(12) 0.0245(2) Uani 1 1 d . . . . .
H6 H 0.501664 0.194607 0.539441 0.029 Uiso 1 1 calc R . . . .
C7 C 0.72900(14) 0.08726(13) 0.39236(12) 0.0242(2) Uani 1 1 d . . . . .
H7 H 0.753249 0.005902 0.468322 0.029 Uiso 1 1 calc R . . . .
C8 C 0.38796(13) 0.44196(13) 0.36311(12) 0.0241(2) Uani 1 1 d . . . . .
C9 C 0.14571(14) 0.54141(13) 0.57012(13) 0.0249(2) Uani 1 1 d . . . . .
H9 H 0.114848 0.618431 0.494501 0.030 Uiso 1 1 calc R . . . .
C10 C 0.04689(14) 0.54430(13) 0.71943(13) 0.0254(2) Uani 1 1 d . . . . .
H10 H 0.073226 0.467476 0.797459 0.031 Uiso 1 1 calc R . . . .
C11 C -0.10517(14) 0.67051(13) 0.76055(12) 0.0241(2) Uani 1 1 d . . . . .
C12 C -0.33092(16) 0.79280(17) 0.96930(14) 0.0352(3) Uani 1 1 d . . . . .
H12A H -0.435879 0.761389 0.966975 0.042 Uiso 1 1 calc R . . . .
H12B H -0.309162 0.895143 0.900735 0.042 Uiso 1 1 calc R . . . .
C13 C -0.35706(17) 0.81246(16) 1.13110(15) 0.0365(3) Uani 1 1 d . . . . .
H13A H -0.252102 0.842424 1.132327 0.055 Uiso 1 1 calc GR . . . .
H13B H -0.380738 0.711183 1.198402 0.055 Uiso 1 1 calc GR . . . .
H13C H -0.455620 0.896775 1.169448 0.055 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4324(13) . ?
O1 C2 1.3553(13) . ?
O2 C8 1.2025(13) . ?
O3 C8 1.3869(13) . ?
O3 C9 1.3725(13) . ?
O4 C11 1.2114(12) . ?
O5 C11 1.3385(13) . ?
O5 C12 1.4526(14) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.3993(14) . ?
C2 C7 1.3942(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.3739(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.4022(14) . ?
C5 C6 1.3905(14) . ?
C5 C8 1.4646(14) . ?
C6 H6 0.9500 . ?
C6 C7 1.3872(15) . ?
C7 H7 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.3232(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.4714(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.4835(17) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C2 O1 C1 117.62(9) . . ?
C9 O3 C8 116.20(8) . . ?
C11 O5 C12 115.96(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 . . ?
O1 C2 C3 115.18(9) . . ?
O1 C2 C7 124.47(9) . . ?
C7 C2 C3 120.35(10) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.06(10) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.33(9) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C8 117.75(9) . . ?
C6 C5 C4 119.08(10) . . ?
C6 C5 C8 123.16(9) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.25(10) . . ?
C7 C6 H6 119.4 . . ?
C2 C7 H7 120.5 . . ?
C6 C7 C2 118.91(9) . . ?
C6 C7 H7 120.5 . . ?
O2 C8 O3 121.93(10) . . ?
O2 C8 C5 126.08(10) . . ?
O3 C8 C5 111.97(9) . . ?
O3 C9 H9 119.3 . . ?
C10 C9 O3 121.49(10) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 121.1 . . ?
C9 C10 C11 117.75(10) . . ?
C11 C10 H10 121.1 . . ?
O4 C11 O5 123.63(10) . . ?
O4 C11 C10 125.13(10) . . ?
O5 C11 C10 111.23(9) . . ?
O5 C12 H12A 110.1 . . ?
O5 C12 H12B 110.1 . . ?
O5 C12 C13 108.02(9) . . ?
H12A C12 H12B 108.4 . . ?
C13 C12 H12A 110.1 . . ?
C13 C12 H12B 110.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -179.17(10) . . . . ?
O1 C2 C7 C6 179.13(10) . . . . ?
O3 C9 C10 C11 178.72(9) . . . . ?
C1 O1 C2 C3 177.37(10) . . . . ?
C1 O1 C2 C7 -2.56(16) . . . . ?
C2 C3 C4 C5 -0.05(16) . . . . ?
C3 C2 C7 C6 -0.80(16) . . . . ?
C3 C4 C5 C6 -0.61(16) . . . . ?
C3 C4 C5 C8 178.82(9) . . . . ?
C4 C5 C6 C7 0.57(16) . . . . ?
C4 C5 C8 O2 3.08(17) . . . . ?
C4 C5 C8 O3 -175.78(9) . . . . ?
C5 C6 C7 C2 0.13(16) . . . . ?
C6 C5 C8 O2 -177.52(11) . . . . ?
C6 C5 C8 O3 3.63(15) . . . . ?
C7 C2 C3 C4 0.76(16) . . . . ?
C8 O3 C9 C10 -177.96(10) . . . . ?
C8 C5 C6 C7 -178.83(10) . . . . ?
C9 O3 C8 O2 0.21(15) . . . . ?
C9 O3 C8 C5 179.13(8) . . . . ?
C9 C10 C11 O4 5.14(17) . . . . ?
C9 C10 C11 O5 -173.76(10) . . . . ?
C11 O5 C12 C13 -158.93(10) . . . . ?
C12 O5 C11 O4 -1.17(16) . . . . ?
C12 O5 C11 C10 177.75(9) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.202
_oxdiff_exptl_absorpt_empirical_full_min 0.678
####################################################################### 
# 
# 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_xray_0116_auto
_database_code_depnum_ccdc_archive 'CCDC 2143069'
loop_
_audit_author_name
_audit_author_address
'Yunxia Li'
;Taiyuan University of Technology
China
;
_audit_update_record             
;
2022-01-19 deposited with the CCDC.	2022-07-08 downloaded from the CCDC.
;
_audit_creation_date             2022-01-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H17 Cl O6'
_chemical_formula_sum            'C17 H17 Cl O6'
_chemical_formula_weight         352.75
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      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                   7.7704(5)
_cell_length_b                   10.7352(7)
_cell_length_c                   10.8707(7)
_cell_angle_alpha                91.269(5)
_cell_angle_beta                 97.889(5)
_cell_angle_gamma                90.643(5)
_cell_volume                     897.90(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4188
_cell_measurement_temperature    300.85(10)
_cell_measurement_theta_max      28.1480
_cell_measurement_theta_min      1.8950
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.793
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12562
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.793
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.907
_diffrn_reflns_theta_min         1.892
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.85(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.793
_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  23.00   1.00    0.51    --    3.79 -67.00  50.00   90
  2  ω    -17.00  33.00   1.00    0.51    --    3.79 -99.00 -30.00   50
  3  ω    -42.00 -16.00   1.00    0.51    --    3.79 -37.00-180.00   26
  4  ω    -15.00  69.00   1.00    0.51    --    3.79  67.00-175.00   84
  5  ω    -18.00  26.00   1.00    0.51    --   -6.53 -99.00-120.00   44
  6  ω    -18.00  26.00   1.00    0.51    --   -6.53 -99.00  30.00   44
  7  ω    -18.00  17.00   1.00    0.51    --   -6.53 -99.00  90.00   35
  8  ω      1.00  26.00   1.00    0.51    --   -6.53 -99.00 120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0060426000
_diffrn_orient_matrix_UB_12      0.0233629000
_diffrn_orient_matrix_UB_13      0.0619878000
_diffrn_orient_matrix_UB_21      0.0641856000
_diffrn_orient_matrix_UB_22      -0.0446862000
_diffrn_orient_matrix_UB_23      0.0190346000
_diffrn_orient_matrix_UB_31      0.0658542000
_diffrn_orient_matrix_UB_32      0.0427341000
_diffrn_orient_matrix_UB_33      -0.0115577000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2501
_reflns_number_total             4507
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4507
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.051
_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)+(0.0722P)²+0.0646P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1583
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C16') \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17') \\sim Ueq, Uanis(C17)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: C16(0.65) H16A(0.65) H16B(0.65) C17(0.6) H17A(0.6) H17B(0.6)
 H17C(0.6) C16'(0.35) H16C(0.35) H16D(0.35) C17'(0.4) H17D(0.4) H17E(0.4)
 H17F(0.4)
4.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C16(H16A,H16B), C16'(H16C,H16D)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8)
4.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C17(H17A,H17B,H17C), C17'(H17D,H17E,H17F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.02985(11) 0.90898(6) 0.66473(8) 0.1223(3) Uani 1 1 d . . . . .
O1 O 0.3224(2) 0.35561(13) 0.56888(12) 0.0879(5) Uani 1 1 d . . . . .
O2 O 0.31254(15) 0.44106(10) 0.38153(10) 0.0599(3) Uani 1 1 d . . . . .
O3 O 0.47391(19) 0.11932(11) 0.23934(13) 0.0775(4) Uani 1 1 d . . . . .
O4 O 0.5040(2) 0.20680(13) 0.05923(13) 0.0883(5) Uani 1 1 d . . . . .
O5 O 0.1817(2) 0.47317(17) -0.06962(14) 0.1056(6) Uani 1 1 d . . . . .
O6 O 0.1270(2) 0.29777(14) 0.02546(14) 0.0876(4) Uani 1 1 d . . . . .
C1 C 0.2133(2) 0.56066(15) 0.54005(14) 0.0551(4) Uani 1 1 d . . . . .
C2 C 0.1890(3) 0.65999(18) 0.46154(17) 0.0751(5) Uani 1 1 d . . . . .
H2 H 0.221861 0.654055 0.382542 0.090 Uiso 1 1 calc R U . . .
C3 C 0.1163(3) 0.7678(2) 0.4999(2) 0.0920(7) Uani 1 1 d . . . . .
H3 H 0.099656 0.835089 0.447370 0.110 Uiso 1 1 calc R U . . .
C4 C 0.0683(3) 0.77472(18) 0.6175(2) 0.0763(5) Uani 1 1 d . . . . .
C5 C 0.0934(3) 0.6789(2) 0.69687(17) 0.0732(5) Uani 1 1 d . . . . .
H5 H 0.062174 0.685885 0.776299 0.088 Uiso 1 1 calc R U . . .
C6 C 0.1659(2) 0.57110(18) 0.65784(15) 0.0636(5) Uani 1 1 d . . . . .
H6 H 0.183152 0.504568 0.711290 0.076 Uiso 1 1 calc R U . . .
C7 C 0.2870(2) 0.44217(16) 0.50333(15) 0.0579(4) Uani 1 1 d . . . . .
C8 C 0.3749(2) 0.33479(15) 0.33256(15) 0.0555(4) Uani 1 1 d . . . . .
H8 H 0.406576 0.267918 0.383333 0.067 Uiso 1 1 calc R U . . .
C9 C 0.3900(2) 0.32749(15) 0.21277(14) 0.0536(4) Uani 1 1 d . . . . .
C10 C 0.4614(2) 0.21329(16) 0.16078(16) 0.0615(4) Uani 1 1 d . . . . .
C11 C 0.5441(4) 0.00444(19) 0.1974(3) 0.0990(7) Uani 1 1 d . . . . .
H11A H 0.660473 0.018691 0.177243 0.119 Uiso 1 1 calc R U . . .
H11B H 0.471749 -0.028217 0.123652 0.119 Uiso 1 1 calc R U . . .
C12 C 0.5482(5) -0.0844(3) 0.2990(3) 0.1467(13) Uani 1 1 d . . . . .
H12A H 0.589289 -0.163261 0.272655 0.220 Uiso 1 1 calc R U . . .
H12B H 0.433244 -0.094884 0.320628 0.220 Uiso 1 1 calc R U . . .
H12C H 0.624596 -0.052948 0.370121 0.220 Uiso 1 1 calc R U . . .
C13 C 0.3445(2) 0.42972(16) 0.12595(14) 0.0576(4) Uani 1 1 d . . . . .
C14 C 0.4160(3) 0.54198(19) 0.1414(2) 0.0717(5) Uani 1 1 d . . . . .
C15 C 0.2125(3) 0.4048(2) 0.01584(16) 0.0710(5) Uani 1 1 d . . . . .
C16 C 0.0152(8) 0.2661(8) -0.0908(6) 0.105(2) Uani 0.65 1 d . U P A 1
H16A H 0.083839 0.256085 -0.158426 0.126 Uiso 0.65 1 calc R U P A 1
H16B H -0.069260 0.330744 -0.111563 0.126 Uiso 0.65 1 calc R U P A 1
C17 C -0.0725(10) 0.1474(7) -0.0685(7) 0.155(3) Uani 0.6 1 d . U P A 1
H17A H -0.160631 0.127900 -0.137331 0.232 Uiso 0.6 1 calc R U P A 1
H17B H -0.124913 0.155298 0.006219 0.232 Uiso 0.6 1 calc R U P A 1
H17C H 0.011088 0.081863 -0.059934 0.232 Uiso 0.6 1 calc R U P A 1
C16' C -0.0439(18) 0.2558(15) -0.0526(11) 0.103(4) Uani 0.35 1 d . U P A 2
H16C H -0.116691 0.206446 -0.005946 0.123 Uiso 0.35 1 calc R U P A 2
H16D H -0.109029 0.324882 -0.090421 0.123 Uiso 0.35 1 calc R U P A 2
C17' C 0.0365(16) 0.1805(10) -0.1427(11) 0.156(4) Uani 0.4 1 d . U P A 2
H17D H -0.052254 0.145659 -0.204391 0.234 Uiso 0.4 1 calc R U P A 2
H17E H 0.101044 0.114494 -0.100742 0.234 Uiso 0.4 1 calc R U P A 2
H17F H 0.113516 0.232155 -0.182115 0.234 Uiso 0.4 1 calc R U P A 2
H14A H 0.377(2) 0.6067(18) 0.0795(19) 0.077(6) Uiso 1 1 d . . . . .
H14B H 0.502(3) 0.562(2) 0.217(2) 0.094(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.738(2) . ?
O1 C7 1.195(2) . ?
O2 C7 1.3654(19) . ?
O2 C8 1.370(2) . ?
O3 C10 1.332(2) . ?
O3 C11 1.444(2) . ?
O4 C10 1.196(2) . ?
O5 C15 1.197(2) . ?
O6 C15 1.334(2) . ?
O6 C16 1.463(6) . ?
O6 C16' 1.532(15) . ?
C1 C2 1.379(2) . ?
C1 C6 1.383(2) . ?
C1 C7 1.470(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(3) . ?
C4 C5 1.356(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(3) . ?
C6 H6 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.324(2) . ?
C9 C10 1.484(2) . ?
C9 C13 1.478(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.473(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.319(3) . ?
C13 C15 1.483(3) . ?
C14 H14A 1.00(2) . ?
C14 H14B 1.00(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.479(10) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C16' H16C 0.9700 . ?
C16' H16D 0.9700 . ?
C16' C17' 1.466(16) . ?
C17' H17D 0.9600 . ?
C17' H17E 0.9600 . ?
C17' H17F 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
C7 O2 C8 118.29(12) . . ?
C10 O3 C11 116.90(16) . . ?
C15 O6 C16 110.6(3) . . ?
C15 O6 C16' 126.4(6) . . ?
C2 C1 C6 119.44(17) . . ?
C2 C1 C7 122.56(15) . . ?
C6 C1 C7 118.00(15) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.09(17) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.07(18) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 Cl1 119.28(17) . . ?
C5 C4 Cl1 118.89(16) . . ?
C5 C4 C3 121.83(19) . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.83(17) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.73(17) . . ?
C5 C6 H6 119.6 . . ?
O1 C7 O2 122.31(16) . . ?
O1 C7 C1 126.12(15) . . ?
O2 C7 C1 111.57(13) . . ?
O2 C8 H8 120.1 . . ?
C9 C8 O2 119.85(14) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C10 119.63(15) . . ?
C8 C9 C13 123.57(15) . . ?
C13 C9 C10 116.77(14) . . ?
O3 C10 C9 112.89(15) . . ?
O4 C10 O3 123.70(16) . . ?
O4 C10 C9 123.40(16) . . ?
O3 C11 H11A 110.2 . . ?
O3 C11 H11B 110.2 . . ?
O3 C11 C12 107.4(2) . . ?
H11A C11 H11B 108.5 . . ?
C12 C11 H11A 110.2 . . ?
C12 C11 H11B 110.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 C15 118.43(16) . . ?
C14 C13 C9 123.19(17) . . ?
C14 C13 C15 118.38(17) . . ?
C13 C14 H14A 118.5(11) . . ?
C13 C14 H14B 119.9(12) . . ?
H14A C14 H14B 121.6(17) . . ?
O5 C15 O6 123.70(19) . . ?
O5 C15 C13 124.8(2) . . ?
O6 C15 C13 111.46(15) . . ?
O6 C16 H16A 110.6 . . ?
O6 C16 H16B 110.6 . . ?
O6 C16 C17 105.6(5) . . ?
H16A C16 H16B 108.8 . . ?
C17 C16 H16A 110.6 . . ?
C17 C16 H16B 110.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O6 C16' H16C 112.6 . . ?
O6 C16' H16D 112.6 . . ?
H16C C16' H16D 110.1 . . ?
C17' C16' O6 95.8(9) . . ?
C17' C16' H16C 112.6 . . ?
C17' C16' H16D 112.6 . . ?
C16' C17' H17D 109.5 . . ?
C16' C17' H17E 109.5 . . ?
C16' C17' H17F 109.5 . . ?
H17D C17' H17E 109.5 . . ?
H17D C17' H17F 109.5 . . ?
H17E C17' H17F 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
Cl1 C4 C5 C6 177.90(15) . . . . ?
O2 C8 C9 C10 178.59(14) . . . . ?
O2 C8 C9 C13 0.7(3) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C2 C1 C7 O1 174.6(2) . . . . ?
C2 C1 C7 O2 -5.2(2) . . . . ?
C2 C3 C4 Cl1 -178.04(18) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C6 C1 C7 O1 -5.9(3) . . . . ?
C6 C1 C7 O2 174.32(14) . . . . ?
C7 O2 C8 C9 175.39(15) . . . . ?
C7 C1 C2 C3 178.70(19) . . . . ?
C7 C1 C6 C5 -178.87(16) . . . . ?
C8 O2 C7 O1 2.5(3) . . . . ?
C8 O2 C7 C1 -177.68(13) . . . . ?
C8 C9 C10 O3 11.6(2) . . . . ?
C8 C9 C10 O4 -168.02(18) . . . . ?
C8 C9 C13 C14 58.0(3) . . . . ?
C8 C9 C13 C15 -122.30(18) . . . . ?
C9 C13 C15 O5 -169.19(18) . . . . ?
C9 C13 C15 O6 13.0(2) . . . . ?
C10 O3 C11 C12 179.1(2) . . . . ?
C10 C9 C13 C14 -119.98(19) . . . . ?
C10 C9 C13 C15 59.8(2) . . . . ?
C11 O3 C10 O4 0.4(3) . . . . ?
C11 O3 C10 C9 -179.30(17) . . . . ?
C13 C9 C10 O3 -170.34(15) . . . . ?
C13 C9 C10 O4 10.0(3) . . . . ?
C14 C13 C15 O5 10.6(3) . . . . ?
C14 C13 C15 O6 -167.28(17) . . . . ?
C15 O6 C16 C17 -179.7(6) . . . . ?
C15 O6 C16' C17' 96.4(10) . . . . ?
C16 O6 C15 O5 10.1(4) . . . . ?
C16 O6 C15 C13 -172.0(4) . . . . ?
C16' O6 C15 O5 -13.2(6) . . . . ?
C16' O6 C15 C13 164.6(6) . . . . ?

_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 1.839
_oxdiff_exptl_absorpt_empirical_full_min 0.403
####################################################################### 
# 
# 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_r20220103a
_database_code_depnum_ccdc_archive 'CCDC 2133581'
loop_
_audit_author_name
_audit_author_address
'Yunxia Li'
;Taiyuan University of Technology
China
;
_audit_update_record             
;
2022-01-10 deposited with the CCDC.	2022-07-08 downloaded from the CCDC.
;
_audit_creation_date             2022-01-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 F2 O5'
_chemical_formula_sum            'C19 H14 F2 O5'
_chemical_formula_weight         360.30
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   7.2621(2)
_cell_length_b                   14.5996(4)
_cell_length_c                   15.7127(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1665.92(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15364
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.8990
_cell_measurement_theta_min      1.9580
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23672
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.905
_diffrn_reflns_theta_min         2.593
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0166679000
_diffrn_orient_matrix_UB_12      0.0289934000
_diffrn_orient_matrix_UB_13      -0.0353756000
_diffrn_orient_matrix_UB_21      0.0081895000
_diffrn_orient_matrix_UB_22      -0.0380894000
_diffrn_orient_matrix_UB_23      -0.0277451000
_diffrn_orient_matrix_UB_31      -0.0959250000
_diffrn_orient_matrix_UB_32      -0.0083237000
_diffrn_orient_matrix_UB_33      0.0038535000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.903
_reflns_number_gt                5226
_reflns_number_total             5790
_reflns_odcompleteness_completeness 99.80
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.297
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 2177 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_ls_extinction_coef       0.015(2)
_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   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         5790
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.023
_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)+(0.0526P)²+0.1073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0965
_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:
 C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C12(H12), C13(H13), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.87123(18) 0.66118(10) 0.15831(9) 0.0456(3) Uani 1 1 d . . . . .
F2 F 0.87210(18) 0.33641(9) 0.50044(9) 0.0423(3) Uani 1 1 d . . . . .
O1 O 0.5837(2) 0.86167(8) 0.48641(8) 0.0301(3) Uani 1 1 d . . . . .
O2 O 0.53324(17) 0.71340(7) 0.52142(7) 0.0215(2) Uani 1 1 d . . . . .
O3 O 0.20817(17) 0.55720(8) 0.65253(9) 0.0277(3) Uani 1 1 d . . . . .
O4 O 0.3680(2) 0.65516(9) 0.80464(9) 0.0380(4) Uani 1 1 d . . . . .
O5 O 0.36402(19) 0.79908(8) 0.75366(8) 0.0265(3) Uani 1 1 d . . . . .
C1 C 0.7988(3) 0.68882(15) 0.23307(12) 0.0304(4) Uani 1 1 d . . . . .
C2 C 0.7832(3) 0.78164(14) 0.24724(11) 0.0287(4) Uani 1 1 d . . . . .
H2 H 0.818670 0.824766 0.205049 0.034 Uiso 1 1 calc R . . . .
C3 C 0.7141(2) 0.80987(12) 0.32484(11) 0.0240(3) Uani 1 1 d . . . . .
H3 H 0.702281 0.873419 0.336628 0.029 Uiso 1 1 calc R . . . .
C4 C 0.6616(2) 0.74570(11) 0.38604(10) 0.0203(3) Uani 1 1 d . . . . .
C5 C 0.6774(3) 0.65225(12) 0.36941(12) 0.0251(3) Uani 1 1 d . . . . .
H5 H 0.640904 0.608721 0.411070 0.030 Uiso 1 1 calc R . . . .
C6 C 0.7470(3) 0.62297(13) 0.29129(13) 0.0307(4) Uani 1 1 d . . . . .
H6 H 0.758421 0.559615 0.278560 0.037 Uiso 1 1 calc R . . . .
C7 C 0.5920(2) 0.78269(11) 0.46707(10) 0.0200(3) Uani 1 1 d . . . . .
C8 C 0.4878(2) 0.73972(10) 0.60250(10) 0.0194(3) Uani 1 1 d . . . . .
H8 H 0.507161 0.801299 0.619884 0.023 Uiso 1 1 calc R . . . .
C9 C 0.4166(2) 0.67933(10) 0.65720(11) 0.0194(3) Uani 1 1 d . . . . .
C10 C 0.3643(2) 0.58244(10) 0.63577(10) 0.0200(3) Uani 1 1 d . . . . .
C11 C 0.5012(2) 0.52008(10) 0.59648(10) 0.0201(3) Uani 1 1 d . . . . .
C12 C 0.6895(2) 0.53596(11) 0.60508(11) 0.0232(3) Uani 1 1 d . . . . .
H12 H 0.731385 0.589632 0.633255 0.028 Uiso 1 1 calc R . . . .
C13 C 0.8163(3) 0.47390(12) 0.57278(12) 0.0279(4) Uani 1 1 d . . . . .
H13 H 0.944874 0.483520 0.579245 0.034 Uiso 1 1 calc R . . . .
C14 C 0.7496(3) 0.39806(13) 0.53112(11) 0.0283(4) Uani 1 1 d . . . . .
C15 C 0.5644(3) 0.38020(13) 0.51998(13) 0.0316(4) Uani 1 1 d . . . . .
H15 H 0.523952 0.327252 0.490206 0.038 Uiso 1 1 calc R . . . .
C16 C 0.4391(3) 0.44231(12) 0.55379(12) 0.0270(3) Uani 1 1 d . . . . .
H16 H 0.310676 0.431719 0.547785 0.032 Uiso 1 1 calc R . . . .
C17 C 0.3788(2) 0.70794(11) 0.74609(11) 0.0221(3) Uani 1 1 d . . . . .
C18 C 0.3580(3) 0.83439(14) 0.84001(12) 0.0341(4) Uani 1 1 d . . . . .
H18A H 0.470861 0.816691 0.871276 0.041 Uiso 1 1 calc R . . . .
H18B H 0.250084 0.809226 0.870612 0.041 Uiso 1 1 calc R . . . .
C19 C 0.3442(5) 0.93577(15) 0.83426(17) 0.0530(7) Uani 1 1 d . . . . .
H19A H 0.445572 0.959349 0.799402 0.080 Uiso 1 1 calc GR . . . .
H19B H 0.351535 0.962241 0.891474 0.080 Uiso 1 1 calc GR . . . .
H19C H 0.226437 0.952556 0.808110 0.080 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.349(2) . ?
F2 C14 1.354(2) . ?
O1 C7 1.194(2) . ?
O2 C7 1.3908(19) . ?
O2 C8 1.3709(19) . ?
O3 C10 1.221(2) . ?
O4 C17 1.203(2) . ?
O5 C17 1.340(2) . ?
O5 C18 1.452(2) . ?
C1 C2 1.378(3) . ?
C1 C6 1.379(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.396(2) . ?
C4 C5 1.394(2) . ?
C4 C7 1.473(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(3) . ?
C6 H6 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.336(2) . ?
C9 C10 1.503(2) . ?
C9 C17 1.484(2) . ?
C10 C11 1.483(2) . ?
C11 C12 1.393(2) . ?
C11 C16 1.394(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.374(3) . ?
C14 C15 1.381(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(3) . ?
C16 H16 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.486(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C8 O2 C7 116.14(12) . . ?
C17 O5 C18 115.96(14) . . ?
F1 C1 C2 117.85(18) . . ?
F1 C1 C6 118.39(18) . . ?
C2 C1 C6 123.76(17) . . ?
C1 C2 H2 121.1 . . ?
C1 C2 C3 117.78(17) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.47(17) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C7 116.32(15) . . ?
C5 C4 C3 120.36(16) . . ?
C5 C4 C7 123.31(15) . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.65(17) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 117.97(17) . . ?
C1 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
O1 C7 O2 122.05(15) . . ?
O1 C7 C4 126.26(15) . . ?
O2 C7 C4 111.69(13) . . ?
O2 C8 H8 119.8 . . ?
C9 C8 O2 120.41(14) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 125.11(15) . . ?
C8 C9 C17 119.45(14) . . ?
C17 C9 C10 115.42(14) . . ?
O3 C10 C9 118.07(14) . . ?
O3 C10 C11 121.82(14) . . ?
C11 C10 C9 120.11(14) . . ?
C12 C11 C10 121.04(14) . . ?
C12 C11 C16 119.99(15) . . ?
C16 C11 C10 118.90(15) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.45(16) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 121.1 . . ?
C14 C13 C12 117.81(17) . . ?
C14 C13 H13 121.1 . . ?
F2 C14 C13 118.28(17) . . ?
F2 C14 C15 117.97(17) . . ?
C13 C14 C15 123.74(17) . . ?
C14 C15 H15 121.1 . . ?
C14 C15 C16 117.75(16) . . ?
C16 C15 H15 121.1 . . ?
C11 C16 H16 119.9 . . ?
C15 C16 C11 120.23(17) . . ?
C15 C16 H16 119.9 . . ?
O4 C17 O5 124.27(16) . . ?
O4 C17 C9 123.50(15) . . ?
O5 C17 C9 112.20(14) . . ?
O5 C18 H18A 110.2 . . ?
O5 C18 H18B 110.2 . . ?
O5 C18 C19 107.38(17) . . ?
H18A C18 H18B 108.5 . . ?
C19 C18 H18A 110.2 . . ?
C19 C18 H18B 110.2 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
F1 C1 C2 C3 -178.10(16) . . . . ?
F1 C1 C6 C5 178.13(16) . . . . ?
F2 C14 C15 C16 178.13(17) . . . . ?
O2 C8 C9 C10 -5.5(2) . . . . ?
O2 C8 C9 C17 176.40(13) . . . . ?
O3 C10 C11 C12 -156.70(16) . . . . ?
O3 C10 C11 C16 20.3(2) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C2 C3 C4 C7 179.23(16) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C3 C4 C7 O1 -3.4(3) . . . . ?
C3 C4 C7 O2 176.37(14) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C5 C4 C7 O1 176.15(18) . . . . ?
C5 C4 C7 O2 -4.1(2) . . . . ?
C6 C1 C2 C3 1.0(3) . . . . ?
C7 O2 C8 C9 174.81(15) . . . . ?
C7 C4 C5 C6 -179.17(17) . . . . ?
C8 O2 C7 O1 -8.2(2) . . . . ?
C8 O2 C7 C4 172.01(13) . . . . ?
C8 C9 C10 O3 -126.30(18) . . . . ?
C8 C9 C10 C11 54.5(2) . . . . ?
C8 C9 C17 O4 -157.13(18) . . . . ?
C8 C9 C17 O5 20.9(2) . . . . ?
C9 C10 C11 C12 22.5(2) . . . . ?
C9 C10 C11 C16 -160.51(15) . . . . ?
C10 C9 C17 O4 24.6(3) . . . . ?
C10 C9 C17 O5 -157.39(14) . . . . ?
C10 C11 C12 C13 175.77(16) . . . . ?
C10 C11 C16 C15 -176.80(16) . . . . ?
C11 C12 C13 C14 1.2(3) . . . . ?
C12 C11 C16 C15 0.3(3) . . . . ?
C12 C13 C14 F2 -179.05(16) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
C14 C15 C16 C11 0.7(3) . . . . ?
C16 C11 C12 C13 -1.2(2) . . . . ?
C17 O5 C18 C19 179.2(2) . . . . ?
C17 C9 C10 O3 51.9(2) . . . . ?
C17 C9 C10 C11 -127.31(16) . . . . ?
C18 O5 C17 O4 8.0(3) . . . . ?
C18 O5 C17 C9 -170.04(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.432
_oxdiff_exptl_absorpt_empirical_full_min 0.644
