# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_cxy-d-15
_database_code_depnum_ccdc_archive 'CCDC 2002620'
loop_
_audit_author_name
_audit_author_address
'Xiong-Li Liu'
;guizhou university
China
;
_audit_update_record             
;
2020-05-08 deposited with the CCDC.	2021-06-03 downloaded from the CCDC.
;
_audit_creation_date             2019-12-13
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H21 N O5'
_chemical_formula_sum            'C21 H21 N O5'
_chemical_formula_weight         367.39
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   21.9574(10)
_cell_length_b                   5.9872(3)
_cell_length_c                   14.5153(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.023(5)
_cell_angle_gamma                90
_cell_volume                     1907.05(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3054
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.2450
_cell_measurement_theta_min      3.5520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52559
_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    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6212
_diffrn_reflns_point_group_measured_fraction_full 0.875
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.445
_diffrn_reflns_theta_min         3.593
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  11.00   1.00    1.00    --  -40.98 107.00  26.00   26
  2  ω    -79.00 -35.00   1.00    1.00    --  -40.98 107.00  26.00   44
  3  ω   -111.00 -27.00   1.00    1.00    --  -40.98 -38.00-120.00   84
  4  ω   -113.00 -17.00   1.00    1.00    --  -40.98 -57.00 150.00   96
  5  ω     33.00 102.00   1.00    2.00    --  106.95 -95.00 -90.00   69
  6  ω     33.00  89.00   1.00    1.60    --  106.95 -95.00-150.00   56
  7  ω     74.00 178.00   1.00    1.60    --  106.95  15.00 -60.00  104
  8  ω    111.00 178.00   1.00    1.60    --  106.95 125.00  90.00   67
  9  ω     89.00 177.00   1.00    1.60    --  106.95  45.00-180.00   88
 10  ω     52.00  88.00   1.00    1.60    --  106.95 -95.00  90.00   36
 11  ω    -89.00 -28.00   1.00    1.60    --  -42.52 -77.00   0.00   61
 12  ω     69.00 107.00   1.00    1.60    --   42.68 178.00-180.00   38
 13  ω     81.00 121.00   1.00    1.60    --   42.68 178.00 -30.00   40
 14  ω   -116.00 -91.00   1.00    1.26    --  -41.23 -77.00 -60.00   25
 15  ω    -49.00 -23.00   1.00    1.26    --  -41.23 -77.00 -60.00   26
 16  ω     20.00  46.00   1.00    1.26    --   41.23  57.00   0.00   26
 17  ω     30.00  56.00   1.00    1.26    --   41.23  38.00 -30.00   26
 18  ω      6.00  48.00   1.00    1.26    --   41.23 -99.00-150.00   42
 19  ω     15.00  40.00   1.00    1.26    --   41.23  57.00  30.00   25
 20  ω     79.00 105.00   1.00    1.67    --  106.95  61.00 -30.00   26
 21  ω    149.00 175.00   1.00    1.67    --  106.95  77.00 -90.00   26
 22  ω     83.00 124.00   1.00    1.67    --  106.95  45.00  30.00   41
 23  ω     74.00 100.00   1.00    1.67    --  106.95  77.00 -60.00   26
 24  ω     78.00 103.00   1.00    1.67    --  106.95  61.00  30.00   25
 25  ω     80.00 106.00   1.00    1.67    --  106.95  61.00-120.00   26
;
_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      -0.0568181000
_diffrn_orient_matrix_UB_12      -0.0504642000
_diffrn_orient_matrix_UB_13      0.0556543000
_diffrn_orient_matrix_UB_21      -0.0408738000
_diffrn_orient_matrix_UB_22      0.0369300000
_diffrn_orient_matrix_UB_23      -0.0871767000
_diffrn_orient_matrix_UB_31      0.0054418000
_diffrn_orient_matrix_UB_32      -0.2495692000
_diffrn_orient_matrix_UB_33      -0.0241643000
_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         0.556
_reflns_Friedel_fraction_full    0.721
_reflns_Friedel_fraction_max     0.666
_reflns_number_gt                2747
_reflns_number_total             3225
_reflns_odcompleteness_completeness 100.00
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 870 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(15)
_refine_ls_extinction_coef       0.0023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3225
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0636
_refine_ls_restrained_S_all      1.083
_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)+(0.0908P)²+0.9578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1766
_refine_ls_wR_factor_ref         0.1874
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C13(H13), C9(H9), C11(H11), C8(H8), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C19(H19), C15(H15), C16(H16), C18(H18), C17(H17), C1(H1), C2(H2)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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
O2 O 0.42840(12) 0.5282(5) 0.36699(18) 0.0657(7) Uani 1 1 d . . . . .
C12 C 0.33999(17) 0.3886(7) 0.5214(3) 0.0666(10) Uani 1 1 d . . . . .
H12 H 0.340278 0.549812 0.509686 0.080 Uiso 1 1 calc R U . . .
C5 C 0.43240(17) 0.5903(9) 0.2773(3) 0.0705(12) Uani 1 1 d . . . . .
C13 C 0.40161(18) 0.3025(7) 0.4881(3) 0.0680(11) Uani 1 1 d . . . . .
H13 H 0.433383 0.400058 0.514909 0.082 Uiso 1 1 calc R U . . .
N1 N 0.4142(3) 0.0729(10) 0.5225(5) 0.123(2) Uani 1 1 d . . . . .
C4 C 0.4701(2) 0.7676(9) 0.2600(3) 0.0824(14) Uani 1 1 d . . . . .
H4 H 0.491859 0.835640 0.308393 0.099 Uiso 1 1 calc R U . . .
C14 C 0.33713(19) 0.3655(7) 0.6250(3) 0.0687(11) Uani 1 1 d . . . . .
C9 C 0.40761(18) 0.3084(8) 0.3832(3) 0.0720(12) Uani 1 1 d . . . . .
H9 H 0.440000 0.204288 0.367174 0.086 Uiso 1 1 calc R U . . .
C19 C 0.3613(2) 0.5308(8) 0.6811(3) 0.0834(13) Uani 1 1 d . . . . .
H19 H 0.378589 0.656334 0.654809 0.100 Uiso 1 1 calc R U . . .
O4 O 0.3850(4) -0.0743(8) 0.4901(6) 0.202(4) Uani 1 1 d . . . . .
C15 C 0.3115(2) 0.1823(9) 0.6669(4) 0.0882(15) Uani 1 1 d . . . . .
H15 H 0.295110 0.067634 0.630644 0.106 Uiso 1 1 calc R U . . .
C16 C 0.3100(3) 0.1673(10) 0.7612(4) 0.107(2) Uani 1 1 d . . . . .
H16 H 0.292512 0.043003 0.788088 0.128 Uiso 1 1 calc R U . . .
C3 C 0.4759(3) 0.8460(13) 0.1705(4) 0.113(2) Uani 1 1 d . . . . .
O1 O 0.3232(2) 0.229(2) 0.1680(4) 0.243(5) Uani 1 1 d . . . . .
O5 O 0.4530(3) 0.0573(13) 0.5866(6) 0.199(4) Uani 1 1 d . . . . .
C6 C 0.39991(19) 0.4868(15) 0.2070(3) 0.112(3) Uani 1 1 d . . . . .
C18 C 0.3604(3) 0.5133(11) 0.7756(4) 0.1012(17) Uani 1 1 d . . . . .
H18 H 0.377812 0.624596 0.812651 0.121 Uiso 1 1 calc R U . . .
C17 C 0.3336(3) 0.3308(11) 0.8150(4) 0.1040(19) Uani 1 1 d . . . . .
H17 H 0.331885 0.320408 0.878773 0.125 Uiso 1 1 calc R U . . .
C11 C 0.2851(2) 0.2996(14) 0.4662(4) 0.104(2) Uani 1 1 d . . . . .
H11 H 0.282980 0.136985 0.473201 0.124 Uiso 1 1 calc R U . . .
C8 C 0.3503(2) 0.2461(13) 0.3272(4) 0.109(2) Uani 1 1 d . . . . .
H8 H 0.345184 0.083670 0.330125 0.131 Uiso 1 1 calc R U . . .
C7 C 0.3566(2) 0.3115(19) 0.2283(4) 0.148(4) Uani 1 1 d . . . . .
C1 C 0.4071(3) 0.562(2) 0.1167(4) 0.161(4) Uani 1 1 d . . . . .
H1 H 0.385999 0.491257 0.068365 0.193 Uiso 1 1 calc R U . . .
C20 C 0.2259(2) 0.406(2) 0.4999(4) 0.148(4) Uani 1 1 d . . . . .
H20A H 0.216338 0.343953 0.558586 0.221 Uiso 1 1 calc R U . . .
H20B H 0.193122 0.376287 0.456082 0.221 Uiso 1 1 calc R U . . .
H20C H 0.231367 0.564669 0.505912 0.221 Uiso 1 1 calc R U . . .
C2 C 0.4439(3) 0.734(2) 0.0985(4) 0.161(4) Uani 1 1 d . . . . .
H2 H 0.448272 0.779893 0.037860 0.193 Uiso 1 1 calc R U . . .
C21 C 0.5183(4) 1.0392(14) 0.1536(5) 0.155(3) Uani 1 1 d . . . . .
H21A H 0.534673 1.093928 0.211506 0.233 Uiso 1 1 calc R U . . .
H21B H 0.496189 1.156619 0.122211 0.233 Uiso 1 1 calc R U . . .
H21C H 0.550989 0.989986 0.116368 0.233 Uiso 1 1 calc R U . . .
O3 O 0.2943(2) 0.5893(16) 0.3460(4) 0.154(3) Uani 1 1 d . . . . .
H3 H 0.259750 0.639046 0.337946 0.230 Uiso 1 1 calc R U . . .
C10 C 0.2913(3) 0.359(2) 0.3633(5) 0.142(4) Uani 1 1 d . . . . .
H10 H 0.255997 0.297795 0.328567 0.171 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
O2 C5 1.360(5) . ?
O2 C9 1.415(5) . ?
C12 H12 0.9800 . ?
C12 C13 1.542(5) . ?
C12 C14 1.513(6) . ?
C12 C11 1.520(6) . ?
C5 C4 1.375(7) . ?
C5 C6 1.372(7) . ?
C13 H13 0.9800 . ?
C13 N1 1.485(7) . ?
C13 C9 1.532(6) . ?
N1 O4 1.178(10) . ?
N1 O5 1.242(10) . ?
C4 H4 0.9300 . ?
C4 C3 1.391(7) . ?
C14 C19 1.377(7) . ?
C14 C15 1.383(6) . ?
C9 H9 0.9800 . ?
C9 C8 1.520(6) . ?
C19 H19 0.9300 . ?
C19 C18 1.376(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.374(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.345(9) . ?
C3 C2 1.408(12) . ?
C3 C21 1.511(11) . ?
O1 C7 1.227(7) . ?
C6 C7 1.456(11) . ?
C6 C1 1.401(9) . ?
C18 H18 0.9300 . ?
C18 C17 1.375(8) . ?
C17 H17 0.9300 . ?
C11 H11 0.9800 . ?
C11 C20 1.544(8) . ?
C11 C10 1.547(10) . ?
C8 H8 0.9800 . ?
C8 C7 1.499(9) . ?
C8 C10 1.568(10) . ?
C1 H1 0.9300 . ?
C1 C2 1.340(15) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C2 H2 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
O3 H3 0.8200 . ?
O3 C10 1.404(12) . ?
C10 H10 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
C5 O2 C9 116.5(4) . . ?
C13 C12 H12 105.3 . . ?
C14 C12 H12 105.3 . . ?
C14 C12 C13 110.4(4) . . ?
C14 C12 C11 115.6(4) . . ?
C11 C12 H12 105.3 . . ?
C11 C12 C13 113.9(4) . . ?
O2 C5 C4 116.5(4) . . ?
O2 C5 C6 122.6(5) . . ?
C6 C5 C4 120.9(5) . . ?
C12 C13 H13 107.2 . . ?
N1 C13 C12 111.0(3) . . ?
N1 C13 H13 107.2 . . ?
N1 C13 C9 109.5(4) . . ?
C9 C13 C12 114.3(4) . . ?
C9 C13 H13 107.2 . . ?
O4 N1 C13 117.8(8) . . ?
O4 N1 O5 126.3(7) . . ?
O5 N1 C13 115.8(7) . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C3 120.5(6) . . ?
C3 C4 H4 119.8 . . ?
C19 C14 C12 119.6(4) . . ?
C19 C14 C15 117.6(4) . . ?
C15 C14 C12 122.8(4) . . ?
O2 C9 C13 103.1(3) . . ?
O2 C9 H9 108.1 . . ?
O2 C9 C8 113.9(5) . . ?
C13 C9 H9 108.1 . . ?
C8 C9 C13 115.3(3) . . ?
C8 C9 H9 108.1 . . ?
C14 C19 H19 119.5 . . ?
C18 C19 C14 121.1(5) . . ?
C18 C19 H19 119.5 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.0(5) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.6(5) . . ?
C17 C16 H16 119.7 . . ?
C4 C3 C2 118.2(7) . . ?
C4 C3 C21 119.1(7) . . ?
C2 C3 C21 122.6(7) . . ?
C5 C6 C7 119.6(5) . . ?
C5 C6 C1 118.5(7) . . ?
C1 C6 C7 121.8(6) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 C19 119.8(6) . . ?
C17 C18 H18 120.1 . . ?
C16 C17 C18 119.9(6) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C12 C11 H11 109.5 . . ?
C12 C11 C20 110.4(5) . . ?
C12 C11 C10 109.5(4) . . ?
C20 C11 H11 109.5 . . ?
C20 C11 C10 108.3(6) . . ?
C10 C11 H11 109.5 . . ?
C9 C8 H8 108.4 . . ?
C9 C8 C10 113.2(4) . . ?
C7 C8 C9 110.2(4) . . ?
C7 C8 H8 108.4 . . ?
C7 C8 C10 108.2(7) . . ?
C10 C8 H8 108.4 . . ?
O1 C7 C6 121.2(7) . . ?
O1 C7 C8 120.3(7) . . ?
C6 C7 C8 118.3(5) . . ?
C6 C1 H1 119.3 . . ?
C2 C1 C6 121.4(7) . . ?
C2 C1 H1 119.3 . . ?
C11 C20 H20A 109.5 . . ?
C11 C20 H20B 109.5 . . ?
C11 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C3 C2 H2 119.8 . . ?
C1 C2 C3 120.5(6) . . ?
C1 C2 H2 119.8 . . ?
C3 C21 H21A 109.5 . . ?
C3 C21 H21B 109.5 . . ?
C3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C10 O3 H3 109.5 . . ?
C11 C10 C8 109.0(8) . . ?
C11 C10 H10 108.4 . . ?
C8 C10 H10 108.4 . . ?
O3 C10 C11 113.8(7) . . ?
O3 C10 C8 108.6(6) . . ?
O3 C10 H10 108.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C5 C4 C3 -178.5(4) . . . . ?
O2 C5 C6 C7 3.5(9) . . . . ?
O2 C5 C6 C1 -179.8(6) . . . . ?
O2 C9 C8 C7 47.2(7) . . . . ?
O2 C9 C8 C10 -74.2(8) . . . . ?
C12 C13 N1 O4 71.4(6) . . . . ?
C12 C13 N1 O5 -105.1(6) . . . . ?
C12 C13 C9 O2 86.1(4) . . . . ?
C12 C13 C9 C8 -38.6(6) . . . . ?
C12 C14 C19 C18 -178.9(5) . . . . ?
C12 C14 C15 C16 179.8(5) . . . . ?
C12 C11 C10 C8 61.1(9) . . . . ?
C12 C11 C10 O3 -60.3(8) . . . . ?
C5 O2 C9 C13 -173.8(3) . . . . ?
C5 O2 C9 C8 -48.2(4) . . . . ?
C5 C4 C3 C2 -2.1(9) . . . . ?
C5 C4 C3 C21 -179.2(5) . . . . ?
C5 C6 C7 O1 173.8(8) . . . . ?
C5 C6 C7 C8 -1.5(11) . . . . ?
C5 C6 C1 C2 -1.3(12) . . . . ?
C13 C12 C14 C19 85.0(5) . . . . ?
C13 C12 C14 C15 -94.3(5) . . . . ?
C13 C12 C11 C20 -176.2(6) . . . . ?
C13 C12 C11 C10 -56.9(8) . . . . ?
C13 C9 C8 C7 166.0(6) . . . . ?
C13 C9 C8 C10 44.7(9) . . . . ?
N1 C13 C9 O2 -148.6(4) . . . . ?
N1 C13 C9 C8 86.7(6) . . . . ?
C4 C5 C6 C7 -175.0(6) . . . . ?
C4 C5 C6 C1 1.6(9) . . . . ?
C4 C3 C2 C1 2.4(12) . . . . ?
C14 C12 C13 N1 52.7(6) . . . . ?
C14 C12 C13 C9 177.1(4) . . . . ?
C14 C12 C11 C20 54.4(7) . . . . ?
C14 C12 C11 C10 173.6(6) . . . . ?
C14 C19 C18 C17 -1.6(9) . . . . ?
C14 C15 C16 C17 -0.2(9) . . . . ?
C9 O2 C5 C4 -159.3(4) . . . . ?
C9 O2 C5 C6 22.1(6) . . . . ?
C9 C13 N1 O4 -55.7(6) . . . . ?
C9 C13 N1 O5 127.7(6) . . . . ?
C9 C8 C7 O1 161.8(9) . . . . ?
C9 C8 C7 C6 -22.9(10) . . . . ?
C9 C8 C10 C11 -55.7(10) . . . . ?
C9 C8 C10 O3 68.8(9) . . . . ?
C19 C14 C15 C16 0.4(8) . . . . ?
C19 C18 C17 C16 1.8(10) . . . . ?
C15 C14 C19 C18 0.4(7) . . . . ?
C15 C16 C17 C18 -1.0(10) . . . . ?
C6 C5 C4 C3 0.1(7) . . . . ?
C6 C1 C2 C3 -0.7(14) . . . . ?
C11 C12 C13 N1 -79.3(7) . . . . ?
C11 C12 C13 C9 45.1(6) . . . . ?
C11 C12 C14 C19 -143.8(5) . . . . ?
C11 C12 C14 C15 36.8(6) . . . . ?
C7 C6 C1 C2 175.2(8) . . . . ?
C7 C8 C10 C11 -178.2(6) . . . . ?
C7 C8 C10 O3 -53.7(7) . . . . ?
C1 C6 C7 O1 -2.7(13) . . . . ?
C1 C6 C7 C8 -178.0(8) . . . . ?
C20 C11 C10 C8 -178.4(7) . . . . ?
C20 C11 C10 O3 60.2(7) . . . . ?
C21 C3 C2 C1 179.4(8) . . . . ?
C10 C8 C7 O1 -74.0(11) . . . . ?
C10 C8 C7 C6 101.4(8) . . . . ?

_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 2.000
_oxdiff_exptl_absorpt_empirical_full_min 0.515
####################################################################### 
# 
# 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_17-15
_database_code_depnum_ccdc_archive 'CCDC 2084001'
loop_
_audit_author_name
_audit_author_address
ghgh
;de
China
;
_audit_update_record             
;
2021-05-16 deposited with the CCDC.	2021-06-03 downloaded from the CCDC.
;
_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C36 H20 Br4 O8)'
_chemical_formula_sum            'C18 H10 Br2 O4'
_chemical_formula_weight         450.08
_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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   12.5529(7)
_cell_length_b                   6.6080(5)
_cell_length_c                   19.3655(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1606.36(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1689
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      72.0060
_cell_measurement_theta_min      4.1760
_shelx_estimated_absorpt_T_max   0.589
_shelx_estimated_absorpt_T_min   0.459
_exptl_absorpt_coefficient_mu    6.584
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51563
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.861
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3861
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.537
_diffrn_reflns_theta_min         4.197
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -86.00 -46.00   1.00    1.00    --  -40.73 125.00 -60.00   40
  2  ω   -113.00 -19.00   1.00    1.00    --  -40.73 -38.00  60.00   94
  3  ω   -113.00 -80.00   1.00    1.00    --  -40.73 -38.00 -30.00   33
  4  ω     35.00  88.00   1.00    1.06    --  107.58 -94.00 -30.00   53
  5  ω     35.00 133.00   1.00    1.06    --  107.58 -45.00   0.00   98
  6  ω     97.00 132.00   1.00    1.06    --  107.58 -30.00  90.00   35
  7  ω     88.00 122.00   1.00    1.06    --  107.58-125.00 120.00   34
  8  ω     34.00  61.00   1.00    1.06    --  107.58 -30.00  90.00   27
  9  ω    115.00 142.00   1.00    1.06    --  107.58 125.00-150.00   27
;
_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      -0.0182566000
_diffrn_orient_matrix_UB_12      0.0546606000
_diffrn_orient_matrix_UB_13      -0.0884494000
_diffrn_orient_matrix_UB_21      -0.0539433000
_diffrn_orient_matrix_UB_22      0.0550355000
_diffrn_orient_matrix_UB_23      0.0839939000
_diffrn_orient_matrix_UB_31      0.2263486000
_diffrn_orient_matrix_UB_32      0.0174468000
_diffrn_orient_matrix_UB_33      0.0128964000
_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                1540
_reflns_number_total             1716
_reflns_odcompleteness_completeness 99.82
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.330
_refine_diff_density_min         -1.170
_refine_diff_density_rms         0.242
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1716
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0995
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1597P)²+12.8020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2587
_refine_ls_wR_factor_ref         0.2644
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: H1(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C2(H2), C13(H13), C15(H15), C9(H9), C17(H17), C14(H14), C4(H4)
3.b Tetrahedral OH refined with riding coordinates:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.09270(5) 0.250000 0.51881(3) 0.03815(19) Uani 1 2 d S T P . .
Br2 Br 0.73318(6) 0.250000 0.13474(4) 0.0524(3) Uani 1 2 d S T P . .
O4 O 0.8821(3) 0.250000 0.4290(2) 0.0330(11) Uani 1 2 d S T P . .
O3 O 0.5599(3) 0.250000 0.3931(2) 0.0333(11) Uani 1 2 d S T P . .
O1 O 0.4082(4) 0.250000 0.7523(2) 0.0534(17) Uani 1 2 d S T P . .
H1 H 0.421719 0.133005 0.763325 0.080 Uiso 0.5 1 calc R U P . .
C5 C 0.2294(4) 0.250000 0.7123(3) 0.0229(13) Uani 1 2 d S T P . .
H5 H 0.205264 0.250000 0.757665 0.027 Uiso 1 2 calc R U P . .
O2 O 0.5556(3) 0.250000 0.6664(2) 0.0425(14) Uani 1 2 d S T P . .
C008 C 0.8445(5) 0.250000 0.3607(3) 0.0285(14) Uani 1 2 d S T P . .
C8 C 0.5362(4) 0.250000 0.5461(3) 0.0300(15) Uani 1 2 d S T P . .
H8 H 0.490989 0.250000 0.508070 0.036 Uiso 1 2 calc R U P . .
C10 C 0.7014(4) 0.250000 0.4741(3) 0.0258(14) Uani 1 2 d S T P . .
C11 C 0.6574(5) 0.250000 0.4050(3) 0.0316(15) Uani 1 2 d S T P . .
C2 C 0.3006(5) 0.250000 0.5762(3) 0.0285(14) Uani 1 2 d S T P . .
H2 H 0.323206 0.250000 0.530440 0.034 Uiso 1 2 calc R U P . .
C16 C 0.7786(5) 0.250000 0.2274(3) 0.0370(18) Uani 1 2 d S T P . .
C13 C 0.8105(5) 0.250000 0.4814(3) 0.0341(17) Uani 1 2 d S T P . .
H13 H 0.837374 0.250000 0.526155 0.041 Uiso 1 2 calc R U P . .
C6 C 0.3412(5) 0.250000 0.6978(3) 0.0344(16) Uani 1 2 d S T P . .
C7 C 0.4932(5) 0.250000 0.6163(3) 0.0356(17) Uani 1 2 d S T P . .
C3 C 0.1936(5) 0.250000 0.5909(3) 0.0326(16) Uani 1 2 d S T P . .
C15 C 0.8873(5) 0.250000 0.2417(3) 0.0392(18) Uani 1 2 d S T P . .
H15 H 0.936590 0.250000 0.205867 0.047 Uiso 1 2 calc R U P . .
C12 C 0.7371(5) 0.250000 0.3479(3) 0.0278(14) Uani 1 2 d S T P . .
C9 C 0.6424(4) 0.250000 0.5378(3) 0.0249(13) Uani 1 2 d S T P . .
H9 H 0.682739 0.250000 0.578066 0.030 Uiso 1 2 calc R U P . .
C1 C 0.3768(4) 0.250000 0.6301(3) 0.0287(15) Uani 1 2 d S T P . .
C17 C 0.7026(5) 0.250000 0.2792(3) 0.0329(16) Uani 1 2 d S T P . .
H17 H 0.630319 0.250000 0.268553 0.039 Uiso 1 2 calc R U P . .
C14 C 0.9216(6) 0.250000 0.3101(4) 0.0405(18) Uani 1 2 d S T P . .
H14 H 0.993718 0.250000 0.321113 0.049 Uiso 1 2 calc R U P . .
C4 C 0.1589(5) 0.250000 0.6589(3) 0.0380(17) Uani 1 2 d S T P . .
H4 H 0.086157 0.250000 0.668121 0.046 Uiso 1 2 calc R U P . .


_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
Br1 C3 1.886(6) . ?
Br2 C16 1.883(6) . ?
O4 C008 1.405(7) . ?
O4 C13 1.356(7) . ?
O3 C11 1.246(7) . ?
O1 H1 0.8200 . ?
O1 H1 0.8200 7_565 ?
O1 C6 1.349(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.430(8) . ?
C5 C4 1.362(9) . ?
O2 C7 1.246(8) . ?
C008 C12 1.371(8) . ?
C008 C14 1.378(10) . ?
C8 H8 0.9300 . ?
C8 C7 1.463(8) . ?
C8 C9 1.343(8) . ?
C10 C11 1.447(8) . ?
C10 C13 1.376(8) . ?
C10 C9 1.438(8) . ?
C11 C12 1.491(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.373(8) . ?
C2 C1 1.417(8) . ?
C16 C15 1.392(9) . ?
C16 C17 1.384(9) . ?
C13 H13 0.9300 . ?
C6 C1 1.384(8) . ?
C7 C1 1.485(8) . ?
C3 C4 1.386(9) . ?
C15 H15 0.9300 . ?
C15 C14 1.392(10) . ?
C12 C17 1.399(8) . ?
C9 H9 0.9300 . ?
C17 H17 0.9300 . ?
C14 H14 0.9300 . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O4 C008 118.9(5) . . ?
H1 O1 H1 141.1 . 7_565 ?
C6 O1 H1 109.5 . . ?
C6 O1 H1 109.468(2) . 7_565 ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.3(5) . . ?
C12 C008 O4 120.0(5) . . ?
C12 C008 C14 124.3(6) . . ?
C14 C008 O4 115.7(6) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C9 C8 C7 118.6(5) . . ?
C13 C10 C11 118.3(5) . . ?
C13 C10 C9 115.1(5) . . ?
C9 C10 C11 126.6(5) . . ?
O3 C11 C10 123.1(5) . . ?
O3 C11 C12 121.4(5) . . ?
C10 C11 C12 115.5(5) . . ?
C3 C2 H2 119.8 . . ?
C3 C2 C1 120.5(5) . . ?
C1 C2 H2 119.8 . . ?
C15 C16 Br2 119.1(5) . . ?
C17 C16 Br2 118.8(5) . . ?
C17 C16 C15 122.1(6) . . ?
O4 C13 C10 125.6(5) . . ?
O4 C13 H13 117.2 . . ?
C10 C13 H13 117.2 . . ?
O1 C6 C5 117.2(5) . . ?
O1 C6 C1 122.6(5) . . ?
C1 C6 C5 120.2(5) . . ?
O2 C7 C8 119.4(5) . . ?
O2 C7 C1 118.6(6) . . ?
C8 C7 C1 122.0(5) . . ?
C2 C3 Br1 120.2(4) . . ?
C2 C3 C4 120.4(6) . . ?
C4 C3 Br1 119.4(5) . . ?
C16 C15 H15 120.2 . . ?
C16 C15 C14 119.5(6) . . ?
C14 C15 H15 120.2 . . ?
C008 C12 C11 121.7(5) . . ?
C008 C12 C17 118.4(6) . . ?
C17 C12 C11 119.9(5) . . ?
C8 C9 C10 127.9(5) . . ?
C8 C9 H9 116.1 . . ?
C10 C9 H9 116.1 . . ?
C2 C1 C7 122.1(5) . . ?
C6 C1 C2 118.7(5) . . ?
C6 C1 C7 119.2(5) . . ?
C16 C17 C12 118.4(6) . . ?
C16 C17 H17 120.8 . . ?
C12 C17 H17 120.8 . . ?
C008 C14 C15 117.3(7) . . ?
C008 C14 H14 121.3 . . ?
C15 C14 H14 121.3 . . ?
C5 C4 C3 121.1(6) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C3 C4 C5 180.000(1) . . . . ?
Br2 C16 C15 C14 180.000(1) . . . . ?
Br2 C16 C17 C12 180.000(1) . . . . ?
O4 C008 C12 C11 0.000(1) . . . . ?
O4 C008 C12 C17 180.000(1) . . . . ?
O4 C008 C14 C15 180.000(1) . . . . ?
O3 C11 C12 C008 180.000(1) . . . . ?
O3 C11 C12 C17 0.000(1) . . . . ?
O1 C6 C1 C2 180.000(2) . . . . ?
O1 C6 C1 C7 0.000(2) . . . . ?
C5 C6 C1 C2 0.000(2) . . . . ?
C5 C6 C1 C7 180.000(2) . . . . ?
O2 C7 C1 C2 180.000(2) . . . . ?
O2 C7 C1 C6 0.000(2) . . . . ?
C008 O4 C13 C10 0.000(1) . . . . ?
C008 C12 C17 C16 0.000(1) . . . . ?
C8 C7 C1 C2 0.000(2) . . . . ?
C8 C7 C1 C6 180.000(2) . . . . ?
C10 C11 C12 C008 0.000(1) . . . . ?
C10 C11 C12 C17 180.000(1) . . . . ?
C11 C10 C13 O4 0.000(1) . . . . ?
C11 C10 C9 C8 0.000(2) . . . . ?
C11 C12 C17 C16 180.000(1) . . . . ?
C2 C3 C4 C5 0.000(2) . . . . ?
C16 C15 C14 C008 0.000(1) . . . . ?
C13 O4 C008 C12 0.000(1) . . . . ?
C13 O4 C008 C14 180.000(1) . . . . ?
C13 C10 C11 O3 180.000(1) . . . . ?
C13 C10 C11 C12 0.000(1) . . . . ?
C13 C10 C9 C8 180.000(1) . . . . ?
C6 C5 C4 C3 0.000(2) . . . . ?
C7 C8 C9 C10 180.000(1) . . . . ?
C3 C2 C1 C6 0.000(2) . . . . ?
C3 C2 C1 C7 180.000(2) . . . . ?
C15 C16 C17 C12 0.000(1) . . . . ?
C12 C008 C14 C15 0.000(1) . . . . ?
C9 C8 C7 O2 0.000(2) . . . . ?
C9 C8 C7 C1 180.000(1) . . . . ?
C9 C10 C11 O3 0.000(1) . . . . ?
C9 C10 C11 C12 180.000(1) . . . . ?
C9 C10 C13 O4 180.000(1) . . . . ?
C1 C2 C3 Br1 180.000(1) . . . . ?
C1 C2 C3 C4 0.000(2) . . . . ?
C17 C16 C15 C14 0.000(1) . . . . ?
C14 C008 C12 C11 180.000(1) . . . . ?
C14 C008 C12 C17 0.000(1) . . . . ?
C4 C5 C6 O1 180.000(1) . . . . ?
C4 C5 C6 C1 0.000(2) . . . . ?

_olex2_date_sample_data_collection 2021-02-04
_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 1.699
_oxdiff_exptl_absorpt_empirical_full_min 0.714
####################################################################### 
# 
# 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_17-10
_database_code_depnum_ccdc_archive 'CCDC 2084000'
loop_
_audit_author_name
_audit_author_address
ghgh
;de
China
;
_audit_update_record             
;
2021-05-16 deposited with the CCDC.	2021-06-03 downloaded from the CCDC.
;
_audit_creation_date             2021-02-03
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H12 O4'
_chemical_formula_sum            'C18 H12 O4'
_chemical_formula_weight         292.28
_chemical_absolute_configuration ?
_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      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                   23.3436(14)
_cell_length_b                   4.9735(3)
_cell_length_c                   11.5943(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1346.09(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1709
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.5240
_cell_measurement_theta_min      5.3470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.845
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55326
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2876
_diffrn_reflns_point_group_measured_fraction_full 0.715
_diffrn_reflns_point_group_measured_fraction_max 0.682
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.619
_diffrn_reflns_theta_min         3.787
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  34.00   1.00    1.00    --  -40.73  38.00 -60.00   50
  2  ω    -56.00 -22.00   1.00    1.00    --  -40.73  38.00 -60.00   34
  3  ω    -81.00 -13.00   1.00    1.00    --  -40.73 -57.00 -60.00   68
  4  ω   -102.00 -68.00   1.00    1.00    --  -40.73-137.00  52.00   34
  5  ω     66.00 105.00   1.00    1.70    --  107.58 -94.00  90.00   39
  6  ω     30.00  57.00   1.00    1.70    --  107.58 -94.00  90.00   27
  7  ω     30.00  77.00   1.00    1.70    --  107.58 -94.00  30.00   47
  8  ω     57.00 173.00   1.00    1.70    --  107.58  15.00 -30.00  116
;
_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      0.0069640000
_diffrn_orient_matrix_UB_12      -0.0810903000
_diffrn_orient_matrix_UB_13      -0.1274532000
_diffrn_orient_matrix_UB_21      0.0656587000
_diffrn_orient_matrix_UB_22      0.0125804000
_diffrn_orient_matrix_UB_23      0.0130304000
_diffrn_orient_matrix_UB_31      0.0008771000
_diffrn_orient_matrix_UB_32      -0.2985183000
_diffrn_orient_matrix_UB_33      0.0352009000
_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         0.353
_reflns_Friedel_fraction_full    0.398
_reflns_Friedel_fraction_max     0.375
_reflns_number_gt                1778
_reflns_number_total             1857
_reflns_odcompleteness_completeness 100.00
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         1857
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0348
_refine_ls_restrained_S_all      1.074
_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)+(0.0537P)²+0.0968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0900
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9(3)
 0.1(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C15(H15), C16(H16),
 C17(H17), C18(H18)
3.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.55567(9) 1.3871(4) 0.4020(2) 0.0385(5) Uani 1 1 d . . . . .
H1 H 0.581751 1.324255 0.363094 0.058 Uiso 1 1 calc R U . . .
O2 O 0.63773(9) 1.0716(4) 0.35227(19) 0.0346(4) Uani 1 1 d . . . . .
O3 O 0.73620(8) 0.2971(3) 0.59728(17) 0.0304(4) Uani 1 1 d . . . . .
O4 O 0.83043(8) 0.2209(3) 0.30189(16) 0.0265(4) Uani 1 1 d . . . . .
C1 C 0.58488(10) 1.0152(5) 0.5236(2) 0.0246(5) Uani 1 1 d . . . . .
C2 C 0.54859(11) 1.2367(5) 0.4981(3) 0.0299(6) Uani 1 1 d . . . . .
C3 C 0.50442(11) 1.3048(6) 0.5732(3) 0.0373(7) Uani 1 1 d . . . . .
H3 H 0.481060 1.451112 0.556359 0.045 Uiso 1 1 calc R U . . .
C4 C 0.49489(11) 1.1584(6) 0.6718(3) 0.0388(7) Uani 1 1 d . . . . .
H4 H 0.465491 1.207533 0.721649 0.047 Uiso 1 1 calc R U . . .
C5 C 0.52920(12) 0.9356(6) 0.6977(3) 0.0349(7) Uani 1 1 d . . . . .
H5 H 0.522272 0.833687 0.763488 0.042 Uiso 1 1 calc R U . . .
C6 C 0.57358(10) 0.8692(5) 0.6239(3) 0.0285(6) Uani 1 1 d . . . . .
H6 H 0.596654 0.722481 0.641712 0.034 Uiso 1 1 calc R U . . .
C7 C 0.63196(11) 0.9448(5) 0.4443(2) 0.0255(5) Uani 1 1 d . . . . .
C8 C 0.67250(10) 0.7261(5) 0.4737(2) 0.0243(5) Uani 1 1 d . . . . .
H8 H 0.670236 0.639008 0.544511 0.029 Uiso 1 1 calc R U . . .
C9 C 0.71239(10) 0.6560(5) 0.3966(2) 0.0234(5) Uani 1 1 d . . . . .
H9 H 0.712680 0.753974 0.328273 0.028 Uiso 1 1 calc R U . . .
C10 C 0.75564(10) 0.4443(4) 0.4064(2) 0.0213(5) Uani 1 1 d . . . . .
C11 C 0.78885(10) 0.4078(5) 0.3120(2) 0.0240(5) Uani 1 1 d . . . . .
H11 H 0.782514 0.520296 0.249185 0.029 Uiso 1 1 calc R U . . .
C12 C 0.76469(10) 0.2788(4) 0.5090(2) 0.0229(5) Uani 1 1 d . . . . .
C13 C 0.81195(10) 0.0807(4) 0.4973(2) 0.0218(5) Uani 1 1 d . . . . .
C14 C 0.84200(10) 0.0591(5) 0.3944(2) 0.0222(5) Uani 1 1 d . . . . .
C15 C 0.88568(11) -0.1296(5) 0.3783(2) 0.0264(5) Uani 1 1 d . . . . .
H15 H 0.904917 -0.141213 0.308280 0.032 Uiso 1 1 calc R U . . .
C16 C 0.89963(11) -0.2981(5) 0.4684(3) 0.0285(5) Uani 1 1 d . . . . .
H16 H 0.928612 -0.424644 0.459317 0.034 Uiso 1 1 calc R U . . .
C17 C 0.87045(11) -0.2798(5) 0.5733(2) 0.0280(6) Uani 1 1 d . . . . .
H17 H 0.880207 -0.393433 0.633881 0.034 Uiso 1 1 calc R U . . .
C18 C 0.82714(11) -0.0932(5) 0.5873(2) 0.0266(5) Uani 1 1 d . . . . .
H18 H 0.807831 -0.083017 0.657335 0.032 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 H1 0.8200 . ?
O1 C2 1.352(4) . ?
O2 C7 1.246(3) . ?
O3 C12 1.224(3) . ?
O4 C11 1.349(3) . ?
O4 C14 1.368(3) . ?
C1 C2 1.421(3) . ?
C1 C6 1.396(4) . ?
C1 C7 1.475(3) . ?
C2 C3 1.391(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.400(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.482(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.337(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.463(3) . ?
C10 C11 1.354(3) . ?
C10 C12 1.462(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.485(3) . ?
C13 C14 1.388(3) . ?
C13 C18 1.401(3) . ?
C14 C15 1.398(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.397(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(4) . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C11 O4 C14 118.6(2) . . ?
C2 C1 C7 119.9(2) . . ?
C6 C1 C2 117.6(2) . . ?
C6 C1 C7 122.5(2) . . ?
O1 C2 C1 121.8(2) . . ?
O1 C2 C3 118.1(2) . . ?
C3 C2 C1 120.1(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 H6 118.9 . . ?
C5 C6 C1 122.2(2) . . ?
C5 C6 H6 118.9 . . ?
O2 C7 C1 119.6(2) . . ?
O2 C7 C8 120.0(2) . . ?
C1 C7 C8 120.4(2) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.8(2) . . ?
C9 C8 H8 120.6 . . ?
C8 C9 H9 116.0 . . ?
C8 C9 C10 128.0(2) . . ?
C10 C9 H9 116.0 . . ?
C11 C10 C9 115.4(2) . . ?
C11 C10 C12 120.0(2) . . ?
C12 C10 C9 124.6(2) . . ?
O4 C11 C10 125.1(2) . . ?
O4 C11 H11 117.5 . . ?
C10 C11 H11 117.5 . . ?
O3 C12 C10 124.1(2) . . ?
O3 C12 C13 121.9(2) . . ?
C10 C12 C13 114.0(2) . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 C18 117.7(2) . . ?
C18 C13 C12 122.0(2) . . ?
O4 C14 C13 121.9(2) . . ?
O4 C14 C15 115.7(2) . . ?
C13 C14 C15 122.3(2) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 C14 118.7(2) . . ?
C16 C15 H15 120.7 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.3(2) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.8(2) . . ?
C17 C18 H18 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 179.6(2) . . . . ?
O2 C7 C8 C9 -4.6(4) . . . . ?
O3 C12 C13 C14 177.7(2) . . . . ?
O3 C12 C13 C18 -1.0(4) . . . . ?
O4 C14 C15 C16 179.7(2) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C1 C7 C8 C9 175.7(2) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
C2 C1 C7 O2 -3.8(4) . . . . ?
C2 C1 C7 C8 175.8(2) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 1.5(4) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
C6 C1 C2 O1 -178.9(2) . . . . ?
C6 C1 C2 C3 1.3(3) . . . . ?
C6 C1 C7 O2 175.4(2) . . . . ?
C6 C1 C7 C8 -5.0(4) . . . . ?
C7 C1 C2 O1 0.3(4) . . . . ?
C7 C1 C2 C3 -179.5(2) . . . . ?
C7 C1 C6 C5 -179.7(2) . . . . ?
C7 C8 C9 C10 -178.7(2) . . . . ?
C8 C9 C10 C11 176.6(2) . . . . ?
C8 C9 C10 C12 -3.8(4) . . . . ?
C9 C10 C11 O4 -178.7(2) . . . . ?
C9 C10 C12 O3 1.3(4) . . . . ?
C9 C10 C12 C13 -179.1(2) . . . . ?
C10 C12 C13 C14 -1.9(3) . . . . ?
C10 C12 C13 C18 179.4(2) . . . . ?
C11 O4 C14 C13 0.6(3) . . . . ?
C11 O4 C14 C15 -179.8(2) . . . . ?
C11 C10 C12 O3 -179.2(2) . . . . ?
C11 C10 C12 C13 0.4(3) . . . . ?
C12 C10 C11 O4 1.7(4) . . . . ?
C12 C13 C14 O4 1.5(3) . . . . ?
C12 C13 C14 C15 -178.1(2) . . . . ?
C12 C13 C18 C17 178.6(2) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C14 O4 C11 C10 -2.3(4) . . . . ?
C14 C13 C18 C17 -0.2(4) . . . . ?
C14 C15 C16 C17 0.1(4) . . . . ?
C15 C16 C17 C18 0.3(4) . . . . ?
C16 C17 C18 C13 -0.3(4) . . . . ?
C18 C13 C14 O4 -179.7(2) . . . . ?
C18 C13 C14 C15 0.7(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 1.398
_oxdiff_exptl_absorpt_empirical_full_min 0.477
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9(3)
2 0.1(3)

