# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_xiaoj_1108
_database_code_depnum_ccdc_archive 'CCDC 2153449'
loop_
_audit_author_name
_audit_author_address
'Ya-Wen Wang'
;Southwest Jiaotong University
China
;
_audit_update_record             
;
2022-02-20 deposited with the CCDC.	2022-05-31 downloaded from the CCDC.
;
_audit_creation_date             2017-11-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H16 O6'
_chemical_formula_sum            'C21 H16 O6'
_chemical_formula_weight         364.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.52(17)
_cell_length_b                   8.28(2)
_cell_length_c                   17.87(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.8(8)
_cell_angle_gamma                90.00
_cell_volume                     1633(26)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    533
_cell_measurement_temperature    293.02(10)
_cell_measurement_theta_max      20.0800
_cell_measurement_theta_min      3.4750
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.1175
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5663
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.42
_diffrn_ambient_temperature      293.02(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -11.00   22.00   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000    0.0000 22

#__ type_ start__ end____ width___ exp.time_
  2 omega   -5.00   83.50   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000 -120.0000 59

#__ type_ start__ end____ width___ exp.time_
  3 omega   -9.00   91.50   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000  150.0000 67
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0160254000
_diffrn_orient_matrix_UB_12      -0.0025599000
_diffrn_orient_matrix_UB_13      -0.0363283000
_diffrn_orient_matrix_UB_21      -0.0609387000
_diffrn_orient_matrix_UB_22      0.0073659000
_diffrn_orient_matrix_UB_23      -0.0224708000
_diffrn_orient_matrix_UB_31      0.0058432000
_diffrn_orient_matrix_UB_32      0.0841701000
_diffrn_orient_matrix_UB_33      0.0008776000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1262
_reflns_number_total             3177
_reflns_odcompleteness_completeness 97.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1794
_refine_ls_R_factor_gt           0.0752
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0586P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1575
_refine_ls_wR_factor_ref         0.2213
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B), C20(H20A,H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.0451(3) 0.2734(4) 0.6811(2) 0.0794(11) Uani 1 d . . .
O2 O -0.0061(4) 0.0809(4) 0.2050(2) 0.0829(11) Uani 1 d . . .
O3 O 0.1847(4) 0.0500(4) 0.2732(2) 0.0834(12) Uani 1 d . . .
O4 O 0.1723(3) 0.1647(4) 0.59879(19) 0.0668(10) Uani 1 d . . .
O5 O 0.5977(3) 0.2483(4) 0.5258(3) 0.0887(12) Uani 1 d . . .
O6 O 0.5028(3) 0.1019(4) 0.6028(2) 0.0707(10) Uani 1 d . . .
C1 C 0.0665(4) 0.2306(5) 0.5526(3) 0.0554(13) Uani 1 d . . .
C2 C -0.0047(5) 0.2875(5) 0.5998(3) 0.0616(14) Uani 1 d . . .
C3 C -0.1133(5) 0.3513(5) 0.5629(4) 0.0706(16) Uani 1 d . . .
H3 H -0.1610 0.3940 0.5921 0.085 Uiso 1 calc . . R
C4 C -0.1566(5) 0.3544(5) 0.4791(3) 0.0678(15) Uani 1 d . . .
H4 H -0.2333 0.3964 0.4556 0.081 Uiso 1 calc . . R
C5 C -0.0893(4) 0.2976(5) 0.4317(3) 0.0584(13) Uani 1 d . . .
C6 C -0.1392(5) 0.2924(6) 0.3427(3) 0.0767(16) Uani 1 d . . .
H6A H -0.2263 0.2775 0.3290 0.092 Uiso 1 calc . . R
H6B H -0.1241 0.3959 0.3219 0.092 Uiso 1 calc . . R
C7 C -0.0883(5) 0.1669(6) 0.3056(3) 0.0678(14) Uani 1 d . . .
H7 H -0.1185 0.0659 0.3217 0.081 Uiso 1 calc . . R
C8 C -0.1120(5) 0.1508(6) 0.2173(3) 0.0772(16) Uani 1 d . . .
H8A H -0.1818 0.0823 0.1954 0.093 Uiso 1 calc . . R
H8B H -0.1275 0.2559 0.1926 0.093 Uiso 1 calc . . R
C9 C 0.0874(6) 0.0933(6) 0.2737(3) 0.0658(14) Uani 1 d . . .
C10 C 0.0413(5) 0.1580(5) 0.3375(3) 0.0570(12) Uani 1 d . . .
C11 C 0.1024(4) 0.2000(5) 0.4146(3) 0.0525(12) Uani 1 d . . .
C12 C 0.0293(4) 0.2393(5) 0.4688(3) 0.0517(12) Uani 1 d . . .
C13 C -0.0229(6) 0.3316(7) 0.7316(3) 0.096(2) Uani 1 d . . .
H13A H -0.0976 0.2728 0.7215 0.144 Uiso 1 calc . . GR
H13B H -0.0400 0.4444 0.7219 0.144 Uiso 1 calc . . GR
H13C H 0.0236 0.3166 0.7852 0.144 Uiso 1 calc . . GR
C14 C 0.2326(4) 0.2190(5) 0.4409(3) 0.0494(12) Uani 1 d . . .
C15 C 0.2925(5) 0.3087(5) 0.3969(3) 0.0593(13) Uani 1 d . . .
H15 H 0.2480 0.3554 0.3501 0.071 Uiso 1 calc . . R
C16 C 0.4144(5) 0.3284(6) 0.4216(3) 0.0650(14) Uani 1 d . . .
H16 H 0.4544 0.3898 0.3932 0.078 Uiso 1 calc . . R
C17 C 0.4774(4) 0.2531(5) 0.4912(3) 0.0615(14) Uani 1 d . . .
C18 C 0.4196(5) 0.1637(5) 0.5368(3) 0.0564(12) Uani 1 d . . .
C19 C 0.2997(4) 0.1447(5) 0.5132(3) 0.0493(11) Uani 1 d . . .
C20 C 0.2334(4) 0.0558(5) 0.5611(3) 0.0615(13) Uani 1 d . . .
H20A H 0.1749 -0.0169 0.5277 0.074 Uiso 1 calc . . R
H20B H 0.2905 -0.0086 0.6003 0.074 Uiso 1 calc . . R
C21 C 0.6153(5) 0.1655(7) 0.5999(3) 0.0759(16) Uani 1 d . . .
H21A H 0.6737 0.0790 0.6048 0.091 Uiso 1 calc . . R
H21B H 0.6462 0.2404 0.6428 0.091 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.404(13) . ?
O1 C13 1.440(13) . ?
O2 C8 1.424(17) . ?
O2 C9 1.384(17) . ?
O3 C9 1.181(17) . ?
O4 C1 1.373(17) . ?
O4 C20 1.427(10) . ?
O5 C17 1.35(2) . ?
O5 C21 1.453(10) . ?
O6 C18 1.386(14) . ?
O6 C21 1.414(18) . ?
C1 C2 1.416(13) . ?
C1 C12 1.435(12) . ?
C2 C3 1.343(18) . ?
C3 H3 0.9300 . ?
C3 C4 1.435(13) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(13) . ?
C5 C6 1.526(14) . ?
C5 C12 1.421(19) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.445(9) . ?
C7 H7 0.9800 . ?
C7 C8 1.527(12) . ?
C7 C10 1.44(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.488(11) . ?
C10 C11 1.399(13) . ?
C11 C12 1.491(14) . ?
C11 C14 1.45(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.400(11) . ?
C14 C19 1.437(13) . ?
C15 H15 0.9300 . ?
C15 C16 1.36(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.394(12) . ?
C17 C18 1.403(11) . ?
C18 C19 1.33(2) . ?
C19 C20 1.496(12) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?

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 C13 119.1(8) . . ?
C9 O2 C8 108.4(9) . . ?
C1 O4 C20 116.2(7) . . ?
C17 O5 C21 106.7(8) . . ?
C18 O6 C21 104.4(9) . . ?
O4 C1 C2 110.0(9) . . ?
O4 C1 C12 126.4(7) . . ?
C2 C1 C12 123.6(8) . . ?
O1 C2 C1 116.9(9) . . ?
C3 C2 O1 125.8(8) . . ?
C3 C2 C1 117.2(9) . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.9(8) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 118.5 . . ?
C5 C4 C3 123.0(8) . . ?
C5 C4 H4 118.5 . . ?
C4 C5 C6 122.5(8) . . ?
C4 C5 C12 117.5(9) . . ?
C12 C5 C6 120.0(8) . . ?
C5 C6 H6A 108.6 . . ?
C5 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 C5 114.7(6) . . ?
C7 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
C6 C7 H7 104.8 . . ?
C6 C7 C8 124.2(6) . . ?
C8 C7 H7 104.8 . . ?
C10 C7 C6 111.6(7) . . ?
C10 C7 H7 104.8 . . ?
C10 C7 C8 105.0(9) . . ?
O2 C8 C7 106.8(8) . . ?
O2 C8 H8A 110.4 . . ?
O2 C8 H8B 110.4 . . ?
C7 C8 H8A 110.4 . . ?
C7 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
O2 C9 C10 110.3(9) . . ?
O3 C9 O2 117.9(9) . . ?
O3 C9 C10 131.7(8) . . ?
C7 C10 C9 106.0(9) . . ?
C11 C10 C7 123.1(8) . . ?
C11 C10 C9 130.9(8) . . ?
C10 C11 C12 118.4(9) . . ?
C10 C11 C14 121.8(8) . . ?
C14 C11 C12 119.5(9) . . ?
C1 C12 C11 127.7(8) . . ?
C5 C12 C1 117.6(8) . . ?
C5 C12 C11 114.7(9) . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C11 120.6(8) . . ?
C15 C14 C19 120.5(9) . . ?
C19 C14 C11 119.0(7) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.9(8) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 121.3 . . ?
C15 C16 C17 117.5(8) . . ?
C17 C16 H16 121.3 . . ?
O5 C17 C16 128.7(7) . . ?
O5 C17 C18 108.5(9) . . ?
C16 C17 C18 122.8(9) . . ?
O6 C18 C17 111.2(9) . . ?
C19 C18 O6 128.7(7) . . ?
C19 C18 C17 120.0(8) . . ?
C14 C19 C20 119.6(9) . . ?
C18 C19 C14 118.3(8) . . ?
C18 C19 C20 122.0(8) . . ?
O4 C20 C19 111.2(6) . . ?
O4 C20 H20A 109.4 . . ?
O4 C20 H20B 109.4 . . ?
C19 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
O5 C21 H21A 109.9 . . ?
O5 C21 H21B 109.9 . . ?
O6 C21 O5 108.7(8) . . ?
O6 C21 H21A 109.9 . . ?
O6 C21 H21B 109.9 . . ?
H21A C21 H21B 108.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -177.9(4) . . . . ?
O2 C9 C10 C7 6.3(5) . . . . ?
O2 C9 C10 C11 -175.6(4) . . . . ?
O3 C9 C10 C7 -171.6(6) . . . . ?
O3 C9 C10 C11 6.4(9) . . . . ?
O4 C1 C2 O1 2.5(5) . . . . ?
O4 C1 C2 C3 -178.0(4) . . . . ?
O4 C1 C12 C5 173.7(4) . . . . ?
O4 C1 C12 C11 -8.8(7) . . . . ?
O5 C17 C18 O6 1.1(5) . . . . ?
O5 C17 C18 C19 -177.3(4) . . . . ?
O6 C18 C19 C14 -178.7(4) . . . . ?
O6 C18 C19 C20 4.2(7) . . . . ?
C1 O4 C20 C19 77.0(8) . . . . ?
C1 C2 C3 C4 2.7(7) . . . . ?
C2 C1 C12 C5 -4.8(6) . . . . ?
C2 C1 C12 C11 172.7(4) . . . . ?
C2 C3 C4 C5 -2.0(7) . . . . ?
C3 C4 C5 C6 176.3(4) . . . . ?
C3 C4 C5 C12 -2.2(7) . . . . ?
C4 C5 C6 C7 -151.4(5) . . . . ?
C4 C5 C12 C1 5.3(6) . . . . ?
C4 C5 C12 C11 -172.5(4) . . . . ?
C5 C6 C7 C8 -172.0(5) . . . . ?
C5 C6 C7 C10 -44.8(8) . . . . ?
C6 C5 C12 C1 -173.3(4) . . . . ?
C6 C5 C12 C11 9.0(6) . . . . ?
C6 C7 C8 O2 149.1(5) . . . . ?
C6 C7 C10 C9 -152.1(4) . . . . ?
C6 C7 C10 C11 29.6(7) . . . . ?
C7 C10 C11 C12 6.7(7) . . . . ?
C7 C10 C11 C14 -168.2(5) . . . . ?
C8 O2 C9 O3 -175.6(5) . . . . ?
C8 O2 C9 C10 6.1(5) . . . . ?
C8 C7 C10 C9 -15.1(5) . . . . ?
C8 C7 C10 C11 166.6(4) . . . . ?
C9 O2 C8 C7 -15.5(5) . . . . ?
C9 C10 C11 C12 -171.1(4) . . . . ?
C9 C10 C11 C14 14.0(8) . . . . ?
C10 C7 C8 O2 19.2(6) . . . . ?
C10 C11 C12 C1 156.5(5) . . . . ?
C10 C11 C12 C5 -26.0(6) . . . . ?
C10 C11 C14 C15 46.9(7) . . . . ?
C10 C11 C14 C19 -133.3(5) . . . . ?
C11 C14 C15 C16 179.3(4) . . . . ?
C11 C14 C19 C18 -179.8(4) . . . . ?
C11 C14 C19 C20 -2.6(6) . . . . ?
C12 C1 C2 O1 -178.8(4) . . . . ?
C12 C1 C2 C3 0.7(7) . . . . ?
C12 C5 C6 C7 27.0(7) . . . . ?
C12 C11 C14 C15 -127.9(5) . . . . ?
C12 C11 C14 C19 51.9(6) . . . . ?
C13 O1 C2 C1 179.1(4) . . . . ?
C13 O1 C2 C3 -0.3(7) . . . . ?
C14 C11 C12 C1 -28.5(7) . . . . ?
C14 C11 C12 C5 149.0(5) . . . . ?
C14 C15 C16 C17 1.4(7) . . . . ?
C14 C19 C20 O4 -73.0(7) . . . . ?
C15 C14 C19 C18 0.0(6) . . . . ?
C15 C14 C19 C20 177.2(4) . . . . ?
C15 C16 C17 O5 176.7(5) . . . . ?
C15 C16 C17 C18 -2.0(7) . . . . ?
C16 C17 C18 O6 -180.0(4) . . . . ?
C16 C17 C18 C19 1.5(7) . . . . ?
C17 O5 C21 O6 8.2(5) . . . . ?
C17 C18 C19 C14 -0.5(6) . . . . ?
C17 C18 C19 C20 -177.6(4) . . . . ?
C18 O6 C21 O5 -7.3(5) . . . . ?
C18 C19 C20 O4 104.1(6) . . . . ?
C19 C14 C15 C16 -0.5(6) . . . . ?
C20 O4 C1 C2 159.5(4) . . . . ?
C20 O4 C1 C12 -19.1(6) . . . . ?
C21 O5 C17 C16 175.6(5) . . . . ?
C21 O5 C17 C18 -5.6(5) . . . . ?
C21 O6 C18 C17 3.9(5) . . . . ?
C21 O6 C18 C19 -177.7(5) . . . . ?

_olex2_date_sample_data_collection 2017-11-10
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_wangxh_0531
_database_code_depnum_ccdc_archive 'CCDC 2153450'
loop_
_audit_author_name
_audit_author_address
'Ya-Wen Wang'
;Southwest Jiaotong University
China
;
_audit_update_record             
;
2022-02-20 deposited with the CCDC.	2022-05-31 downloaded from the CCDC.
;
_audit_creation_date             2017-06-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H19 Br O6'
_chemical_formula_sum            'C21 H19 Br O6'
_chemical_formula_weight         447.27
_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'
Br Br -0.2901 2.4595 '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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.6456(9)
_cell_length_b                   8.944(3)
_cell_length_c                   13.8908(19)
_cell_angle_alpha                98.172(17)
_cell_angle_beta                 100.703(11)
_cell_angle_gamma                94.856(16)
_cell_volume                     917.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    747
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.6030
_cell_measurement_theta_min      3.6990
_exptl_absorpt_coefficient_mu    2.277
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.618
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.1274
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5735
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.37
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -2.00   24.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000  120.0000 13

#__ type_ start__ end____ width___ exp.time_
  2 omega  -32.00   10.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055   57.0000  -30.0000 21

#__ type_ start__ end____ width___ exp.time_
  3 omega   -6.00   24.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000  -90.0000 15

#__ type_ start__ end____ width___ exp.time_
  4 omega   -1.00   91.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  150.0000 46

#__ type_ start__ end____ width___ exp.time_
  5 omega  -30.00   46.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000 -150.0000 38

#__ type_ start__ end____ width___ exp.time_
  6 omega  -48.00   46.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000    0.0000 47

#__ type_ start__ end____ width___ exp.time_
  7 omega  -48.00  -22.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -77.0000  120.0000 13
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0084001000
_diffrn_orient_matrix_UB_12      -0.0788143000
_diffrn_orient_matrix_UB_13      -0.0029846000
_diffrn_orient_matrix_UB_21      0.0003019000
_diffrn_orient_matrix_UB_22      0.0053599000
_diffrn_orient_matrix_UB_23      0.0514705000
_diffrn_orient_matrix_UB_31      -0.0946633000
_diffrn_orient_matrix_UB_32      -0.0162203000
_diffrn_orient_matrix_UB_33      -0.0106993000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1957
_reflns_number_total             3599
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3599
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1389
_refine_ls_R_factor_gt           0.0698
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0495P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1670
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C10(H10A,H10B), C14(H14A,H14B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 0.16048(9) 0.68810(9) 0.52317(5) 0.0600(3) Uani 1 d . . .
O1 O -0.3164(6) 0.8589(7) -0.0868(4) 0.0777(17) Uani 1 d . . .
O2 O -0.1565(7) 0.7995(6) -0.2014(3) 0.0677(15) Uani 1 d . . .
O3 O 0.3726(5) 0.5743(5) 0.3153(3) 0.0506(12) Uani 1 d . . .
O4 O 0.0689(4) 0.6879(4) 0.2483(3) 0.0336(10) Uani 1 d . . .
O5 O -0.2361(5) 0.9570(5) 0.2570(3) 0.0470(12) Uani 1 d . . .
O6 O -0.4693(5) 0.9744(5) 0.3406(3) 0.0528(13) Uani 1 d . . .
C1 C -0.0096(10) 0.7109(10) -0.2141(5) 0.066(2) Uani 1 d . . .
H1A H 0.0810 0.7699 -0.2380 0.079 Uiso 1 calc . . R
H1B H -0.0528 0.6197 -0.2624 0.079 Uiso 1 calc . . R
C2 C 0.0705(8) 0.6685(9) -0.1135(4) 0.0538(19) Uani 1 d . . .
H2 H 0.0819 0.5593 -0.1224 0.065 Uiso 1 calc . . R
C3 C 0.2470(8) 0.7527(9) -0.0643(5) 0.057(2) Uani 1 d . . .
H3A H 0.2409 0.8613 -0.0600 0.068 Uiso 1 calc . . R
H3B H 0.3370 0.7252 -0.1024 0.068 Uiso 1 calc . . R
C4 C 0.2962(7) 0.7120(8) 0.0388(4) 0.0434(17) Uani 1 d . . .
C5 C 0.4569(8) 0.6593(8) 0.0748(5) 0.0529(19) Uani 1 d . . .
H5 H 0.5452 0.6556 0.0370 0.064 Uiso 1 calc . . R
C6 C 0.4876(7) 0.6120(8) 0.1669(5) 0.0494(18) Uani 1 d . . .
H6 H 0.5954 0.5757 0.1899 0.059 Uiso 1 calc . . R
C7 C 0.3587(7) 0.6189(8) 0.2241(4) 0.0404(16) Uani 1 d . . .
C8 C 0.1991(7) 0.6788(7) 0.1901(4) 0.0327(14) Uani 1 d . . .
C9 C 0.1661(7) 0.7201(8) 0.0973(4) 0.0404(16) Uani 1 d . . .
C10 C -0.0082(7) 0.7772(8) 0.0526(4) 0.0477(18) Uani 1 d . . .
H10A H -0.0976 0.7575 0.0919 0.057 Uiso 1 calc . . R
H10B H 0.0116 0.8861 0.0542 0.057 Uiso 1 calc . . R
C11 C -0.0761(8) 0.6999(8) -0.0525(4) 0.0491(18) Uani 1 d . . .
H11 H -0.1457 0.6030 -0.0518 0.059 Uiso 1 calc . . R
C12 C -0.1974(9) 0.7969(9) -0.1116(6) 0.058(2) Uani 1 d . . .
C13 C 0.5140(9) 0.4859(8) 0.3428(5) 0.067(2) Uani 1 d . . .
H13A H 0.4998 0.3945 0.2952 0.101 Uiso 1 calc . . GR
H13B H 0.5109 0.4600 0.4073 0.101 Uiso 1 calc . . GR
H13C H 0.6267 0.5433 0.3446 0.101 Uiso 1 calc . . GR
C14 C 0.1032(7) 0.8267(7) 0.3192(4) 0.0363(15) Uani 1 d . . .
H14A H 0.1079 0.9138 0.2850 0.044 Uiso 1 calc . . R
H14B H 0.2173 0.8296 0.3641 0.044 Uiso 1 calc . . R
C15 C -0.0449(7) 0.8316(7) 0.3761(4) 0.0327(14) Uani 1 d . . .
C16 C -0.0426(7) 0.7796(7) 0.4666(5) 0.0375(15) Uani 1 d . . .
C17 C -0.1804(8) 0.7886(8) 0.5172(5) 0.0457(17) Uani 1 d . . .
H17 H -0.1721 0.7506 0.5766 0.055 Uiso 1 calc . . R
C18 C -0.3316(8) 0.8536(8) 0.4805(5) 0.0479(18) Uani 1 d . . .
H18 H -0.4248 0.8620 0.5148 0.057 Uiso 1 calc . . R
C19 C -0.3387(7) 0.9049(7) 0.3920(5) 0.0378(15) Uani 1 d . . .
C20 C -0.4110(7) 1.0067(8) 0.2538(5) 0.0461(17) Uani 1 d . . .
H20A H -0.4051 1.1150 0.2518 0.055 Uiso 1 calc . . R
H20B H -0.4938 0.9536 0.1950 0.055 Uiso 1 calc . . R
C21 C -0.1988(7) 0.8941(7) 0.3426(4) 0.0356(15) Uani 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
Br1 C16 1.909(6) . ?
O1 C12 1.184(8) . ?
O2 C1 1.451(8) . ?
O2 C12 1.344(8) . ?
O3 C7 1.370(7) . ?
O3 C13 1.420(7) . ?
O4 C8 1.395(6) . ?
O4 C14 1.442(6) . ?
O5 C20 1.439(6) . ?
O5 C21 1.379(7) . ?
O6 C19 1.363(7) . ?
O6 C20 1.419(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.532(8) . ?
C2 H2 0.9800 . ?
C2 C3 1.481(8) . ?
C2 C11 1.546(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.515(8) . ?
C4 C5 1.386(8) . ?
C4 C9 1.397(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.376(8) . ?
C7 C8 1.403(7) . ?
C8 C9 1.374(8) . ?
C9 C10 1.523(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.500(8) . ?
C11 H11 0.9800 . ?
C11 C12 1.530(9) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.497(7) . ?
C15 C16 1.398(8) . ?
C15 C21 1.377(7) . ?
C16 C17 1.373(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.366(8) . ?
C19 C21 1.377(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?

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
C12 O2 C1 111.1(6) . . ?
C7 O3 C13 116.2(5) . . ?
C8 O4 C14 111.2(4) . . ?
C21 O5 C20 105.8(4) . . ?
C19 O6 C20 107.1(4) . . ?
O2 C1 H1A 110.1 . . ?
O2 C1 H1B 110.1 . . ?
O2 C1 C2 108.2(5) . . ?
H1A C1 H1B 108.4 . . ?
C2 C1 H1A 110.1 . . ?
C2 C1 H1B 110.1 . . ?
C1 C2 H2 108.8 . . ?
C1 C2 C11 102.8(5) . . ?
C3 C2 C1 115.0(6) . . ?
C3 C2 H2 108.8 . . ?
C3 C2 C11 112.3(5) . . ?
C11 C2 H2 108.8 . . ?
C2 C3 H3A 110.0 . . ?
C2 C3 H3B 110.0 . . ?
C2 C3 C4 108.3(6) . . ?
H3A C3 H3B 108.4 . . ?
C4 C3 H3A 110.0 . . ?
C4 C3 H3B 110.0 . . ?
C5 C4 C3 123.7(6) . . ?
C5 C4 C9 119.0(6) . . ?
C9 C4 C3 117.2(5) . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(6) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.1(6) . . ?
C7 C6 H6 120.0 . . ?
O3 C7 C6 125.5(5) . . ?
O3 C7 C8 115.1(5) . . ?
C6 C7 C8 119.4(6) . . ?
O4 C8 C7 119.7(5) . . ?
C9 C8 O4 119.9(5) . . ?
C9 C8 C7 120.3(5) . . ?
C4 C9 C10 116.3(5) . . ?
C8 C9 C4 120.2(5) . . ?
C8 C9 C10 123.5(5) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 C9 110.9(5) . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C2 C11 H11 108.6 . . ?
C10 C11 C2 115.1(5) . . ?
C10 C11 H11 108.6 . . ?
C10 C11 C12 111.3(6) . . ?
C12 C11 C2 104.6(5) . . ?
C12 C11 H11 108.6 . . ?
O1 C12 O2 122.2(7) . . ?
O1 C12 C11 127.2(7) . . ?
O2 C12 C11 110.6(6) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 H14A 110.0 . . ?
O4 C14 H14B 110.0 . . ?
O4 C14 C15 108.3(4) . . ?
H14A C14 H14B 108.4 . . ?
C15 C14 H14A 110.0 . . ?
C15 C14 H14B 110.0 . . ?
C16 C15 C14 125.5(5) . . ?
C21 C15 C14 121.0(5) . . ?
C21 C15 C16 113.5(5) . . ?
C15 C16 Br1 118.9(4) . . ?
C17 C16 Br1 117.5(5) . . ?
C17 C16 C15 123.6(5) . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.6(6) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 121.3 . . ?
C19 C18 C17 117.4(6) . . ?
C19 C18 H18 121.3 . . ?
O6 C19 C18 129.3(5) . . ?
O6 C19 C21 109.8(5) . . ?
C18 C19 C21 120.9(5) . . ?
O5 C20 H20A 110.2 . . ?
O5 C20 H20B 110.2 . . ?
O6 C20 O5 107.5(4) . . ?
O6 C20 H20A 110.2 . . ?
O6 C20 H20B 110.2 . . ?
H20A C20 H20B 108.5 . . ?
C15 C21 O5 126.2(5) . . ?
C19 C21 O5 109.7(5) . . ?
C19 C21 C15 124.1(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
Br1 C16 C17 C18 179.9(5) . . . . ?
O2 C1 C2 C3 -106.7(7) . . . . ?
O2 C1 C2 C11 15.8(7) . . . . ?
O3 C7 C8 O4 -0.5(8) . . . . ?
O3 C7 C8 C9 -176.6(6) . . . . ?
O4 C8 C9 C4 179.7(5) . . . . ?
O4 C8 C9 C10 0.1(10) . . . . ?
O4 C14 C15 C16 93.1(6) . . . . ?
O4 C14 C15 C21 -88.5(7) . . . . ?
O6 C19 C21 O5 0.0(7) . . . . ?
O6 C19 C21 C15 179.0(6) . . . . ?
C1 O2 C12 O1 -178.1(7) . . . . ?
C1 O2 C12 C11 -0.5(8) . . . . ?
C1 C2 C3 C4 173.1(6) . . . . ?
C1 C2 C11 C10 -137.8(6) . . . . ?
C1 C2 C11 C12 -15.4(7) . . . . ?
C2 C3 C4 C5 126.9(7) . . . . ?
C2 C3 C4 C9 -49.1(8) . . . . ?
C2 C11 C12 O1 -172.0(8) . . . . ?
C2 C11 C12 O2 10.6(8) . . . . ?
C3 C2 C11 C10 -13.6(9) . . . . ?
C3 C2 C11 C12 108.8(6) . . . . ?
C3 C4 C5 C6 -174.6(6) . . . . ?
C3 C4 C9 C8 177.3(6) . . . . ?
C3 C4 C9 C10 -3.1(9) . . . . ?
C4 C5 C6 C7 -0.8(11) . . . . ?
C4 C9 C10 C11 46.7(8) . . . . ?
C5 C4 C9 C8 1.2(10) . . . . ?
C5 C4 C9 C10 -179.2(6) . . . . ?
C5 C6 C7 O3 179.3(6) . . . . ?
C5 C6 C7 C8 -2.2(10) . . . . ?
C6 C7 C8 O4 -179.2(5) . . . . ?
C6 C7 C8 C9 4.7(10) . . . . ?
C7 C8 C9 C4 -4.2(10) . . . . ?
C7 C8 C9 C10 176.3(6) . . . . ?
C8 O4 C14 C15 177.8(4) . . . . ?
C8 C9 C10 C11 -133.7(7) . . . . ?
C9 C4 C5 C6 1.3(11) . . . . ?
C9 C10 C11 C2 -37.1(8) . . . . ?
C9 C10 C11 C12 -155.8(6) . . . . ?
C10 C11 C12 O1 -47.1(10) . . . . ?
C10 C11 C12 O2 135.4(6) . . . . ?
C11 C2 C3 C4 56.0(8) . . . . ?
C12 O2 C1 C2 -10.1(8) . . . . ?
C13 O3 C7 C6 -13.7(9) . . . . ?
C13 O3 C7 C8 167.7(6) . . . . ?
C14 O4 C8 C7 86.1(7) . . . . ?
C14 O4 C8 C9 -97.7(6) . . . . ?
C14 C15 C16 Br1 -2.1(8) . . . . ?
C14 C15 C16 C17 178.9(6) . . . . ?
C14 C15 C21 O5 0.1(10) . . . . ?
C14 C15 C21 C19 -178.7(5) . . . . ?
C15 C16 C17 C18 -1.0(10) . . . . ?
C16 C15 C21 O5 178.6(6) . . . . ?
C16 C15 C21 C19 -0.2(9) . . . . ?
C16 C17 C18 C19 1.2(10) . . . . ?
C17 C18 C19 O6 -179.1(6) . . . . ?
C17 C18 C19 C21 -1.0(9) . . . . ?
C18 C19 C21 O5 -178.4(6) . . . . ?
C18 C19 C21 C15 0.5(10) . . . . ?
C19 O6 C20 O5 -1.6(7) . . . . ?
C20 O5 C21 C15 -179.9(6) . . . . ?
C20 O5 C21 C19 -1.0(7) . . . . ?
C20 O6 C19 C18 179.2(7) . . . . ?
C20 O6 C19 C21 1.0(7) . . . . ?
C21 O5 C20 O6 1.5(6) . . . . ?
C21 C15 C16 Br1 179.5(4) . . . . ?
C21 C15 C16 C17 0.4(9) . . . . ?

_olex2_date_sample_data_collection 2017-06-01
_olex2_submission_special_instructions 'No special instructions were received'
