# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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 
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data_cu_20180628_0m
_database_code_depnum_ccdc_archive 'CCDC 1873121'
loop_
_audit_author_name
_audit_author_address
'Wen-Dao Chu'
;China West Normal University
China
;
_audit_update_record             
;
2018-10-13 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;
_audit_creation_date             2018-10-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H22 N2 O9 S'
_chemical_formula_sum            'C24 H22 N2 O9 S'
_chemical_formula_weight         514.49
_chemical_absolute_configuration S,R,S
_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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   12.2161(5)
_cell_length_b                   12.5468(5)
_cell_length_c                   16.7879(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2573.13(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7678
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      59.799
_cell_measurement_theta_min      4.399
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.925
_exptl_absorpt_coefficient_mu    1.589
_exptl_absorpt_correction_T_max  0.7520
_exptl_absorpt_correction_T_min  0.6391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1193 before and 0.0675 after correction. The Ratio of minimum to maximum transmission is 0.8499. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1518
_diffrn_reflns_av_unetI/netI     0.0734
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17634
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        61.306
_diffrn_reflns_theta_max         61.306
_diffrn_reflns_theta_min         4.399
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3282
_reflns_number_total             3955
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
;
 Flack x determined using 1184 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       0.0065(7)
_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   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         3955
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0704P)²+0.3943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1531
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C13, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 S1, O2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
Uanis(C14) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C12(H12)
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C20(H20), C22(H22), C23(H23),
 C24(H24)
4.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B)
4.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.12977(11) 0.59857(13) 0.32712(12) 0.0770(5) Uani 1 1 d . U . . .
O1 O 0.0965(4) 0.5268(5) 0.2689(5) 0.142(3) Uani 1 1 d . . . . .
O2 O 0.0973(4) 0.5805(5) 0.4077(4) 0.1125(18) Uani 1 1 d . U . . .
O3 O 0.0827(3) 0.7106(4) 0.3015(3) 0.0730(11) Uani 1 1 d . . . . .
O4 O 0.6250(3) 0.4331(3) 0.2951(3) 0.0700(11) Uani 1 1 d . . . . .
O5 O 0.7541(3) 0.5113(3) 0.3682(3) 0.0749(11) Uani 1 1 d . . . . .
O6 O 0.6619(3) 0.7969(3) 0.3198(3) 0.0646(10) Uani 1 1 d . . . . .
O7 O 0.7362(3) 0.6728(3) 0.2428(2) 0.0686(11) Uani 1 1 d . . . . .
O8 O 0.5584(8) 0.8708(5) 0.0684(4) 0.142(3) Uani 1 1 d . . . . .
O9 O 0.4894(11) 0.7954(6) -0.0341(5) 0.194(4) Uani 1 1 d . . . . .
N1 N 0.2627(3) 0.6132(3) 0.3227(3) 0.0592(11) Uani 1 1 d . . . . .
N2 N 0.5129(7) 0.7976(6) 0.0366(4) 0.110(2) Uani 1 1 d . . . . .
C1 C 0.1304(4) 0.8009(4) 0.3343(3) 0.0579(13) Uani 1 1 d . . . . .
C2 C 0.0674(4) 0.8907(5) 0.3415(4) 0.0707(17) Uani 1 1 d . . . . .
H2 H -0.006058 0.889306 0.326943 0.085 Uiso 1 1 calc R . . . .
C3 C 0.1127(5) 0.9811(6) 0.3699(4) 0.0793(19) Uani 1 1 d . . . . .
H3 H 0.069953 1.042071 0.374792 0.095 Uiso 1 1 calc R . . . .
C4 C 0.2227(5) 0.9844(5) 0.3921(4) 0.0735(17) Uani 1 1 d . . . . .
H4 H 0.252835 1.046595 0.412724 0.088 Uiso 1 1 calc R . . . .
C5 C 0.2862(4) 0.8943(4) 0.3832(3) 0.0591(13) Uani 1 1 d . . . . .
H5 H 0.359697 0.896479 0.397525 0.071 Uiso 1 1 calc R . . . .
C6 C 0.2419(4) 0.7998(4) 0.3530(3) 0.0467(11) Uani 1 1 d . . . . .
C7 C 0.3053(3) 0.7043(4) 0.3392(3) 0.0440(10) Uani 1 1 d . . . . .
C8 C 0.4285(3) 0.7087(4) 0.3429(3) 0.0429(10) Uani 1 1 d . . . . .
H8 H 0.452275 0.775171 0.317650 0.052 Uiso 1 1 calc R . . . .
C9 C 0.4738(4) 0.7073(4) 0.4299(3) 0.0531(12) Uani 1 1 d . . . . .
H9 H 0.492627 0.780164 0.445718 0.064 Uiso 1 1 calc R . . . .
C10 C 0.5801(4) 0.6399(4) 0.4247(3) 0.0532(12) Uani 1 1 d . . . . .
H10A H 0.640896 0.678899 0.447790 0.064 Uiso 1 1 calc R . . . .
H10B H 0.571166 0.573764 0.453989 0.064 Uiso 1 1 calc R . . . .
C11 C 0.6028(3) 0.6163(4) 0.3368(3) 0.0449(11) Uani 1 1 d . . . . .
C12 C 0.4855(3) 0.6157(3) 0.3002(3) 0.0432(11) Uani 1 1 d . . . . .
H12 H 0.449948 0.550191 0.318666 0.052 Uiso 1 1 calc R . . . .
C13 C 0.3970(5) 0.6619(8) 0.4889(4) 0.093(2) Uani 1 1 d . U . . .
H13 H 0.374965 0.591686 0.481145 0.111 Uiso 1 1 calc R . . . .
C15 C 0.6600(4) 0.5093(4) 0.3283(3) 0.0504(12) Uani 1 1 d . . . . .
C16 C 0.8178(7) 0.4142(6) 0.3700(5) 0.101(3) Uani 1 1 d . . . . .
H16A H 0.863177 0.410621 0.323342 0.152 Uiso 1 1 calc GR . . . .
H16B H 0.769448 0.353900 0.370999 0.152 Uiso 1 1 calc GR . . . .
H16C H 0.863056 0.413619 0.416696 0.152 Uiso 1 1 calc GR . . . .
C17 C 0.6705(4) 0.7060(4) 0.3001(3) 0.0473(11) Uani 1 1 d . . . . .
C18 C 0.7996(7) 0.7557(6) 0.2034(6) 0.099(3) Uani 1 1 d . . . . .
H18A H 0.836850 0.725922 0.158206 0.148 Uiso 1 1 calc GR . . . .
H18B H 0.852250 0.784447 0.239945 0.148 Uiso 1 1 calc GR . . . .
H18C H 0.751360 0.811435 0.185876 0.148 Uiso 1 1 calc GR . . . .
C19 C 0.4743(4) 0.6174(3) 0.2101(3) 0.0447(11) Uani 1 1 d . . . . .
C20 C 0.4990(4) 0.7072(4) 0.1650(3) 0.0544(12) Uani 1 1 d . . . . .
H20 H 0.525119 0.768994 0.188919 0.065 Uiso 1 1 calc R . . . .
C21 C 0.4836(5) 0.7020(5) 0.0836(4) 0.0680(15) Uani 1 1 d . . . . .
C22 C 0.4438(6) 0.6144(5) 0.0454(4) 0.0784(18) Uani 1 1 d . . . . .
H22 H 0.434871 0.614064 -0.009569 0.094 Uiso 1 1 calc R . . . .
C23 C 0.4174(6) 0.5267(5) 0.0904(4) 0.0738(17) Uani 1 1 d . . . . .
H23 H 0.388672 0.466161 0.066172 0.089 Uiso 1 1 calc R . . . .
C24 C 0.4337(4) 0.5290(4) 0.1718(3) 0.0574(13) Uani 1 1 d . . . . .
H24 H 0.416695 0.468786 0.201617 0.069 Uiso 1 1 calc R . . . .
C14 C 0.3582(7) 0.7104(11) 0.5494(5) 0.147(4) Uani 1 1 d . U . . .
H14A H 0.378005 0.780691 0.559479 0.177 Uiso 1 1 calc R . . . .
H14B H 0.310147 0.675429 0.583550 0.177 Uiso 1 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
S1 O1 1.390(6) . ?
S1 O2 1.427(6) . ?
S1 O3 1.579(5) . ?
S1 N1 1.636(4) . ?
O3 C1 1.388(7) . ?
O4 C15 1.187(6) . ?
O5 C15 1.330(7) . ?
O5 C16 1.446(7) . ?
O6 C17 1.191(6) . ?
O7 C17 1.321(6) . ?
O7 C18 1.456(8) . ?
O8 N2 1.199(10) . ?
O9 N2 1.222(10) . ?
N1 C7 1.286(7) . ?
N2 C21 1.479(9) . ?
C1 C2 1.370(8) . ?
C1 C6 1.398(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.349(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.395(10) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(8) . ?
C6 C7 1.445(7) . ?
C7 C8 1.507(6) . ?
C8 H8 0.9800 . ?
C8 C9 1.561(7) . ?
C8 C12 1.537(6) . ?
C9 H9 0.9800 . ?
C9 C10 1.552(7) . ?
C9 C13 1.478(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.531(7) . ?
C11 C12 1.559(6) . ?
C11 C15 1.520(7) . ?
C11 C17 1.526(7) . ?
C12 H12 0.9800 . ?
C12 C19 1.518(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.276(11) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.391(7) . ?
C19 C24 1.375(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(8) . ?
C21 C22 1.361(9) . ?
C22 H22 0.9300 . ?
C22 C23 1.373(10) . ?
C23 H23 0.9300 . ?
C23 C24 1.381(9) . ?
C24 H24 0.9300 . ?
C14 H14A 0.9300 . ?
C14 H14B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 118.8(5) . . ?
O1 S1 O3 106.2(4) . . ?
O1 S1 N1 109.3(3) . . ?
O2 S1 O3 107.4(3) . . ?
O2 S1 N1 109.7(3) . . ?
O3 S1 N1 104.5(2) . . ?
C1 O3 S1 117.7(3) . . ?
C15 O5 C16 117.4(5) . . ?
C17 O7 C18 115.4(4) . . ?
C7 N1 S1 119.4(4) . . ?
O8 N2 O9 123.9(8) . . ?
O8 N2 C21 119.8(6) . . ?
O9 N2 C21 116.3(8) . . ?
O3 C1 C6 119.4(5) . . ?
C2 C1 O3 118.0(5) . . ?
C2 C1 C6 122.4(5) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.5(5) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.0(5) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.3(7) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.1(5) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C7 119.6(5) . . ?
C5 C6 C1 116.7(5) . . ?
C5 C6 C7 123.7(4) . . ?
N1 C7 C6 123.7(4) . . ?
N1 C7 C8 116.4(4) . . ?
C6 C7 C8 119.8(4) . . ?
C7 C8 H8 108.0 . . ?
C7 C8 C9 113.1(4) . . ?
C7 C8 C12 113.9(4) . . ?
C9 C8 H8 108.0 . . ?
C12 C8 H8 108.0 . . ?
C12 C8 C9 105.5(4) . . ?
C8 C9 H9 109.1 . . ?
C10 C9 C8 104.5(4) . . ?
C10 C9 H9 109.1 . . ?
C13 C9 C8 113.9(4) . . ?
C13 C9 H9 109.1 . . ?
C13 C9 C10 111.0(5) . . ?
C9 C10 H10A 110.1 . . ?
C9 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
C11 C10 C9 108.1(4) . . ?
C11 C10 H10A 110.1 . . ?
C11 C10 H10B 110.1 . . ?
C10 C11 C12 102.4(4) . . ?
C15 C11 C10 110.1(4) . . ?
C15 C11 C12 112.4(4) . . ?
C15 C11 C17 111.4(4) . . ?
C17 C11 C10 110.2(4) . . ?
C17 C11 C12 110.1(4) . . ?
C8 C12 C11 103.2(4) . . ?
C8 C12 H12 106.7 . . ?
C11 C12 H12 106.7 . . ?
C19 C12 C8 114.4(4) . . ?
C19 C12 C11 118.4(4) . . ?
C19 C12 H12 106.7 . . ?
C9 C13 H13 117.1 . . ?
C14 C13 C9 125.9(10) . . ?
C14 C13 H13 117.1 . . ?
O4 C15 O5 124.2(5) . . ?
O4 C15 C11 126.2(4) . . ?
O5 C15 C11 109.5(4) . . ?
O5 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
O5 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O6 C17 O7 123.9(5) . . ?
O6 C17 C11 123.1(4) . . ?
O7 C17 C11 113.0(4) . . ?
O7 C18 H18A 109.5 . . ?
O7 C18 H18B 109.5 . . ?
O7 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C12 122.3(4) . . ?
C24 C19 C12 119.2(4) . . ?
C24 C19 C20 118.4(5) . . ?
C19 C20 H20 120.9 . . ?
C21 C20 C19 118.1(5) . . ?
C21 C20 H20 120.9 . . ?
C20 C21 N2 117.2(6) . . ?
C22 C21 N2 119.3(6) . . ?
C22 C21 C20 123.6(6) . . ?
C21 C22 H22 120.9 . . ?
C21 C22 C23 118.2(6) . . ?
C23 C22 H22 120.9 . . ?
C22 C23 H23 120.2 . . ?
C22 C23 C24 119.5(6) . . ?
C24 C23 H23 120.2 . . ?
C19 C24 C23 122.2(5) . . ?
C19 C24 H24 118.9 . . ?
C23 C24 H24 118.9 . . ?
C13 C14 H14A 120.0 . . ?
C13 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 O3 C1 C2 -152.7(4) . . . . ?
S1 O3 C1 C6 32.1(6) . . . . ?
S1 N1 C7 C6 -7.3(7) . . . . ?
S1 N1 C7 C8 173.3(4) . . . . ?
O1 S1 O3 C1 -160.5(5) . . . . ?
O1 S1 N1 C7 146.2(6) . . . . ?
O2 S1 O3 C1 71.5(4) . . . . ?
O2 S1 N1 C7 -81.9(5) . . . . ?
O3 S1 N1 C7 32.9(5) . . . . ?
O3 C1 C2 C3 -177.1(5) . . . . ?
O3 C1 C6 C5 177.7(5) . . . . ?
O3 C1 C6 C7 -1.0(7) . . . . ?
O8 N2 C21 C20 7.5(11) . . . . ?
O8 N2 C21 C22 -172.3(8) . . . . ?
O9 N2 C21 C20 -173.4(9) . . . . ?
O9 N2 C21 C22 6.9(12) . . . . ?
N1 S1 O3 C1 -45.0(4) . . . . ?
N1 C7 C8 C9 -101.1(5) . . . . ?
N1 C7 C8 C12 19.3(7) . . . . ?
N2 C21 C22 C23 179.9(6) . . . . ?
C1 C2 C3 C4 -0.1(10) . . . . ?
C1 C6 C7 N1 -12.0(7) . . . . ?
C1 C6 C7 C8 167.4(4) . . . . ?
C2 C1 C6 C5 2.7(7) . . . . ?
C2 C1 C6 C7 -176.0(5) . . . . ?
C2 C3 C4 C5 1.4(10) . . . . ?
C3 C4 C5 C6 -0.6(9) . . . . ?
C4 C5 C6 C1 -1.4(7) . . . . ?
C4 C5 C6 C7 177.3(5) . . . . ?
C5 C6 C7 N1 169.4(5) . . . . ?
C5 C6 C7 C8 -11.3(7) . . . . ?
C6 C1 C2 C3 -2.1(9) . . . . ?
C6 C7 C8 C9 79.4(6) . . . . ?
C6 C7 C8 C12 -160.1(4) . . . . ?
C7 C8 C9 C10 143.4(4) . . . . ?
C7 C8 C9 C13 22.1(7) . . . . ?
C7 C8 C12 C11 -161.0(4) . . . . ?
C7 C8 C12 C19 69.0(5) . . . . ?
C8 C9 C10 C11 7.2(5) . . . . ?
C8 C9 C13 C14 -120.0(7) . . . . ?
C8 C12 C19 C20 51.1(6) . . . . ?
C8 C12 C19 C24 -125.9(4) . . . . ?
C9 C8 C12 C11 -36.4(5) . . . . ?
C9 C8 C12 C19 -166.4(4) . . . . ?
C9 C10 C11 C12 -29.2(5) . . . . ?
C9 C10 C11 C15 -148.9(4) . . . . ?
C9 C10 C11 C17 87.9(5) . . . . ?
C10 C9 C13 C14 122.3(8) . . . . ?
C10 C11 C12 C8 40.0(5) . . . . ?
C10 C11 C12 C19 167.6(4) . . . . ?
C10 C11 C15 O4 116.7(6) . . . . ?
C10 C11 C15 O5 -59.7(5) . . . . ?
C10 C11 C17 O6 -33.5(6) . . . . ?
C10 C11 C17 O7 148.8(4) . . . . ?
C11 C12 C19 C20 -71.0(6) . . . . ?
C11 C12 C19 C24 112.1(5) . . . . ?
C12 C8 C9 C10 18.2(5) . . . . ?
C12 C8 C9 C13 -103.1(6) . . . . ?
C12 C11 C15 O4 3.2(8) . . . . ?
C12 C11 C15 O5 -173.2(4) . . . . ?
C12 C11 C17 O6 78.7(6) . . . . ?
C12 C11 C17 O7 -99.0(5) . . . . ?
C12 C19 C20 C21 -178.4(5) . . . . ?
C12 C19 C24 C23 177.4(5) . . . . ?
C13 C9 C10 C11 130.4(5) . . . . ?
C15 C11 C12 C8 158.1(4) . . . . ?
C15 C11 C12 C19 -74.3(5) . . . . ?
C15 C11 C17 O6 -156.0(5) . . . . ?
C15 C11 C17 O7 26.3(6) . . . . ?
C16 O5 C15 O4 0.8(9) . . . . ?
C16 O5 C15 C11 177.2(5) . . . . ?
C17 C11 C12 C8 -77.1(5) . . . . ?
C17 C11 C12 C19 50.5(5) . . . . ?
C17 C11 C15 O4 -120.8(6) . . . . ?
C17 C11 C15 O5 62.8(5) . . . . ?
C18 O7 C17 O6 -0.1(8) . . . . ?
C18 O7 C17 C11 177.5(6) . . . . ?
C19 C20 C21 N2 -178.6(5) . . . . ?
C19 C20 C21 C22 1.2(9) . . . . ?
C20 C19 C24 C23 0.3(8) . . . . ?
C20 C21 C22 C23 0.2(10) . . . . ?
C21 C22 C23 C24 -1.3(10) . . . . ?
C22 C23 C24 C19 1.0(9) . . . . ?
C24 C19 C20 C21 -1.4(7) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.202 0.659 0.070 47.4 3.6 ?
2 0.298 0.341 0.570 47.4 3.7 ?
3 0.702 -0.159 0.930 47.4 3.5 ?
4 0.798 0.159 0.430 47.4 3.7 ?

_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_cu_20180712_0m-auto
_database_code_depnum_ccdc_archive 'CCDC 1874838'
loop_
_audit_author_name
_audit_author_address
'Wen-Dao Chu'
;China West Normal University
China
;
_audit_update_record             
;
2018-10-23 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;
_audit_creation_date             2018-10-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H24 O6'
_chemical_formula_sum            'C24 H24 O6'
_chemical_formula_weight         408.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.3133(4)
_cell_length_b                   11.2328(4)
_cell_length_c                   19.0954(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.604(2)
_cell_angle_gamma                90
_cell_volume                     2181.14(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9854
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.51
_cell_measurement_theta_min      4.58
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.733
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23150
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.962
_diffrn_reflns_theta_min         4.584
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3778
_reflns_number_total             4191
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0677P)²+0.5650P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1372
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C22(H22)
2.d X=CH2 refined with riding coordinates:
 C23(H23A,H23B)
2.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.67477(11) 0.35271(10) 0.63756(8) 0.0665(3) Uani 1 1 d . . . . .
O2 O 0.41482(11) 0.37445(10) 0.54973(5) 0.0564(3) Uani 1 1 d . . . . .
O3 O 0.25877(12) 0.12757(10) 0.79326(7) 0.0635(3) Uani 1 1 d . . . . .
O4 O 0.05602(18) 0.06579(13) 0.84342(9) 0.0865(5) Uani 1 1 d . . . . .
H4 H 0.131(3) 0.061(3) 0.8301(18) 0.130 Uiso 1 1 d R . . . .
O5 O 0.60621(14) 0.17433(12) 0.66369(11) 0.0967(6) Uani 1 1 d . . . . .
O6 O 0.35000(14) 0.51403(11) 0.61908(8) 0.0754(4) Uani 1 1 d . . . . .
C1 C -0.14502(19) 0.3287(3) 0.84559(12) 0.0902(7) Uani 1 1 d . . . . .
H1 H -0.224857 0.349820 0.858647 0.108 Uiso 1 1 calc R . . . .
C2 C -0.0705(2) 0.4143(2) 0.82003(11) 0.0870(7) Uani 1 1 d . . . . .
H2 H -0.099295 0.492843 0.816268 0.104 Uiso 1 1 calc R . . . .
C3 C 0.04701(18) 0.38363(18) 0.80001(9) 0.0661(5) Uani 1 1 d . . . . .
H3 H 0.096712 0.441982 0.782277 0.079 Uiso 1 1 calc R . . . .
C4 C 0.09350(14) 0.26610(14) 0.80576(7) 0.0502(3) Uani 1 1 d . . . . .
C5 C 0.21708(14) 0.23023(13) 0.78298(7) 0.0465(3) Uani 1 1 d . . . . .
C6 C 0.29515(14) 0.31617(12) 0.74551(7) 0.0453(3) Uani 1 1 d . . . . .
H6 H 0.235782 0.377640 0.722087 0.054 Uiso 1 1 calc R . . . .
C7 C 0.35999(13) 0.25250(12) 0.68968(7) 0.0427(3) Uani 1 1 d . . . . .
H7 H 0.407077 0.183746 0.713136 0.051 Uiso 1 1 calc R . . . .
C8 C 0.46695(13) 0.34349(12) 0.67367(7) 0.0438(3) Uani 1 1 d . . . . .
C9 C 0.58742(14) 0.27853(14) 0.65727(9) 0.0537(4) Uani 1 1 d . . . . .
C10 C 0.79423(19) 0.2985(2) 0.62258(16) 0.0907(7) Uani 1 1 d . . . . .
H10A H 0.833206 0.251295 0.662507 0.136 Uiso 1 1 calc GR . . . .
H10B H 0.854740 0.359515 0.613893 0.136 Uiso 1 1 calc GR . . . .
H10C H 0.774093 0.248588 0.581375 0.136 Uiso 1 1 calc GR . . . .
C11 C 0.3391(2) 0.4306(2) 0.48791(10) 0.0869(6) Uani 1 1 d . . . . .
H11A H 0.247102 0.416782 0.487587 0.130 Uiso 1 1 calc GR . . . .
H11B H 0.363854 0.397558 0.445700 0.130 Uiso 1 1 calc GR . . . .
H11C H 0.355968 0.514670 0.489446 0.130 Uiso 1 1 calc GR . . . .
C12 C 0.40629(14) 0.42280(12) 0.61212(8) 0.0465(3) Uani 1 1 d . . . . .
C13 C 0.26785(15) 0.20558(14) 0.62575(8) 0.0522(4) Uani 1 1 d . . . . .
C14 C 0.15110(17) 0.2628(2) 0.59770(10) 0.0735(5) Uani 1 1 d . . . . .
H14 H 0.124828 0.330200 0.619956 0.088 Uiso 1 1 calc R . . . .
C15 C 0.0739(2) 0.2196(3) 0.53663(12) 0.0979(8) Uani 1 1 d . . . . .
H15 H -0.003947 0.258417 0.518173 0.117 Uiso 1 1 calc R . . . .
C16 C 0.1105(3) 0.1211(3) 0.50328(12) 0.1020(9) Uani 1 1 d . . . . .
H16 H 0.058477 0.093612 0.461955 0.122 Uiso 1 1 calc R . . . .
C17 C 0.2241(3) 0.0625(2) 0.53065(12) 0.0944(8) Uani 1 1 d . . . . .
H17 H 0.248560 -0.005410 0.508184 0.113 Uiso 1 1 calc R . . . .
C18 C 0.3032(2) 0.10422(17) 0.59212(9) 0.0692(5) Uani 1 1 d . . . . .
H18 H 0.380094 0.063881 0.610631 0.083 Uiso 1 1 calc R . . . .
C19 C -0.1040(2) 0.2126(3) 0.85223(11) 0.0865(7) Uani 1 1 d . . . . .
H19 H -0.156642 0.155502 0.868890 0.104 Uiso 1 1 calc R . . . .
C20 C 0.01720(17) 0.17985(18) 0.83393(9) 0.0626(4) Uani 1 1 d . . . . .
C21 C 0.41144(15) 0.37745(13) 0.79490(8) 0.0513(4) Uani 1 1 d . . . . .
H21 H 0.378558 0.447552 0.816975 0.062 Uiso 1 1 calc R . . . .
C22 C 0.4818(2) 0.29844(19) 0.85143(10) 0.0732(5) Uani 1 1 d . . . . .
H22 H 0.517667 0.228278 0.837211 0.088 Uiso 1 1 calc R . . . .
C23 C 0.4970(3) 0.3203(3) 0.91923(13) 0.1301(13) Uani 1 1 d . . . . .
H23A H 0.462471 0.389586 0.935439 0.156 Uiso 1 1 calc R . . . .
H23B H 0.542235 0.266607 0.951474 0.156 Uiso 1 1 calc R . . . .
C24 C 0.50081(19) 0.41793(17) 0.74292(9) 0.0654(5) Uani 1 1 d . . . . .
H24A H 0.592271 0.406180 0.763821 0.078 Uiso 1 1 calc R . . . .
H24B H 0.487201 0.501912 0.732339 0.078 Uiso 1 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 C9 1.3270(18) . ?
O1 C10 1.445(2) . ?
O2 C11 1.447(2) . ?
O2 C12 1.3256(18) . ?
O3 C5 1.2350(18) . ?
O4 H4 0.85(3) . ?
O4 C20 1.346(3) . ?
O5 C9 1.189(2) . ?
O6 C12 1.1960(18) . ?
C1 H1 0.9300 . ?
C1 C2 1.371(4) . ?
C1 C19 1.370(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.403(2) . ?
C4 C5 1.470(2) . ?
C4 C20 1.410(2) . ?
C5 C6 1.5114(19) . ?
C6 H6 0.9800 . ?
C6 C7 1.5274(19) . ?
C6 C21 1.557(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.5708(18) . ?
C7 C13 1.5112(19) . ?
C8 C9 1.518(2) . ?
C8 C12 1.5236(19) . ?
C8 C24 1.554(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.391(3) . ?
C13 C18 1.386(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.361(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.369(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.394(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.402(3) . ?
C21 H21 0.9800 . ?
C21 C22 1.489(2) . ?
C21 C24 1.532(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.301(3) . ?
C23 H23A 0.9300 . ?
C23 H23B 0.9300 . ?
C24 H24A 0.9700 . ?
C24 H24B 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
C9 O1 C10 115.65(14) . . ?
C12 O2 C11 116.54(14) . . ?
C20 O4 H4 107(2) . . ?
C2 C1 H1 119.4 . . ?
C2 C1 C19 121.18(19) . . ?
C19 C1 H1 119.4 . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.3(2) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 122.46(14) . . ?
C3 C4 C20 118.12(15) . . ?
C20 C4 C5 119.41(15) . . ?
O3 C5 C4 120.33(13) . . ?
O3 C5 C6 118.21(13) . . ?
C4 C5 C6 121.45(13) . . ?
C5 C6 H6 108.9 . . ?
C5 C6 C7 111.18(11) . . ?
C5 C6 C21 114.39(12) . . ?
C7 C6 H6 108.9 . . ?
C7 C6 C21 104.31(11) . . ?
C21 C6 H6 108.9 . . ?
C6 C7 H7 106.9 . . ?
C6 C7 C8 103.57(11) . . ?
C8 C7 H7 106.9 . . ?
C13 C7 C6 115.95(12) . . ?
C13 C7 H7 106.9 . . ?
C13 C7 C8 115.92(11) . . ?
C9 C8 C7 110.66(11) . . ?
C9 C8 C12 111.52(11) . . ?
C9 C8 C24 111.02(13) . . ?
C12 C8 C7 108.62(11) . . ?
C12 C8 C24 110.29(13) . . ?
C24 C8 C7 104.47(11) . . ?
O1 C9 C8 111.99(12) . . ?
O5 C9 O1 122.72(15) . . ?
O5 C9 C8 125.22(14) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 C8 111.93(12) . . ?
O6 C12 O2 123.86(14) . . ?
O6 C12 C8 124.04(14) . . ?
C14 C13 C7 122.48(16) . . ?
C18 C13 C7 118.82(15) . . ?
C18 C13 C14 118.65(16) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 119.9(2) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 120.3(2) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C1 C19 H19 120.0 . . ?
C1 C19 C20 120.1(2) . . ?
C20 C19 H19 120.0 . . ?
O4 C20 C4 122.22(15) . . ?
O4 C20 C19 118.29(18) . . ?
C19 C20 C4 119.5(2) . . ?
C6 C21 H21 109.2 . . ?
C22 C21 C6 114.12(12) . . ?
C22 C21 H21 109.2 . . ?
C22 C21 C24 111.91(15) . . ?
C24 C21 C6 102.98(12) . . ?
C24 C21 H21 109.2 . . ?
C21 C22 H22 117.6 . . ?
C23 C22 C21 124.9(3) . . ?
C23 C22 H22 117.6 . . ?
C22 C23 H23A 120.0 . . ?
C22 C23 H23B 120.0 . . ?
H23A C23 H23B 120.0 . . ?
C8 C24 H24A 110.0 . . ?
C8 C24 H24B 110.0 . . ?
C21 C24 C8 108.52(12) . . ?
C21 C24 H24A 110.0 . . ?
C21 C24 H24B 110.0 . . ?
H24A C24 H24B 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
O3 C5 C6 C7 34.35(18) . . . . ?
O3 C5 C6 C21 -83.47(17) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C1 C19 C20 O4 177.82(19) . . . . ?
C1 C19 C20 C4 -2.8(3) . . . . ?
C2 C1 C19 C20 1.1(3) . . . . ?
C2 C3 C4 C5 178.34(17) . . . . ?
C2 C3 C4 C20 -1.0(3) . . . . ?
C3 C4 C5 O3 175.23(15) . . . . ?
C3 C4 C5 C6 -5.8(2) . . . . ?
C3 C4 C20 O4 -177.92(16) . . . . ?
C3 C4 C20 C19 2.7(2) . . . . ?
C4 C5 C6 C7 -144.62(13) . . . . ?
C4 C5 C6 C21 97.56(16) . . . . ?
C5 C4 C20 O4 2.7(2) . . . . ?
C5 C4 C20 C19 -176.68(15) . . . . ?
C5 C6 C7 C8 -163.66(11) . . . . ?
C5 C6 C7 C13 68.20(15) . . . . ?
C5 C6 C21 C22 37.60(19) . . . . ?
C5 C6 C21 C24 159.12(14) . . . . ?
C6 C7 C8 C9 146.11(12) . . . . ?
C6 C7 C8 C12 -91.15(13) . . . . ?
C6 C7 C8 C24 26.55(15) . . . . ?
C6 C7 C13 C14 33.3(2) . . . . ?
C6 C7 C13 C18 -149.25(14) . . . . ?
C6 C21 C22 C23 -122.7(2) . . . . ?
C6 C21 C24 C8 -20.49(18) . . . . ?
C7 C6 C21 C22 -84.07(16) . . . . ?
C7 C6 C21 C24 37.45(15) . . . . ?
C7 C8 C9 O1 174.58(12) . . . . ?
C7 C8 C9 O5 -8.4(2) . . . . ?
C7 C8 C12 O2 -86.29(14) . . . . ?
C7 C8 C12 O6 89.09(17) . . . . ?
C7 C8 C24 C21 -3.42(18) . . . . ?
C7 C13 C14 C15 176.37(17) . . . . ?
C7 C13 C18 C17 -176.35(17) . . . . ?
C8 C7 C13 C14 -88.52(18) . . . . ?
C8 C7 C13 C18 88.97(17) . . . . ?
C9 C8 C12 O2 35.93(16) . . . . ?
C9 C8 C12 O6 -148.69(15) . . . . ?
C9 C8 C24 C21 -122.74(15) . . . . ?
C10 O1 C9 O5 1.4(3) . . . . ?
C10 O1 C9 C8 178.55(16) . . . . ?
C11 O2 C12 O6 -6.7(2) . . . . ?
C11 O2 C12 C8 168.65(14) . . . . ?
C12 C8 C9 O1 53.54(17) . . . . ?
C12 C8 C9 O5 -129.4(2) . . . . ?
C12 C8 C24 C21 113.12(15) . . . . ?
C13 C7 C8 C9 -85.74(16) . . . . ?
C13 C7 C8 C12 37.00(16) . . . . ?
C13 C7 C8 C24 154.70(14) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C13 C18 C17 1.2(3) . . . . ?
C14 C15 C16 C17 0.9(4) . . . . ?
C15 C16 C17 C18 -0.8(4) . . . . ?
C16 C17 C18 C13 -0.3(3) . . . . ?
C18 C13 C14 C15 -1.1(3) . . . . ?
C19 C1 C2 C3 0.6(3) . . . . ?
C20 C4 C5 O3 -5.4(2) . . . . ?
C20 C4 C5 C6 173.55(14) . . . . ?
C21 C6 C7 C8 -39.89(13) . . . . ?
C21 C6 C7 C13 -168.03(12) . . . . ?
C22 C21 C24 C8 102.52(17) . . . . ?
C24 C8 C9 O1 -69.89(17) . . . . ?
C24 C8 C9 O5 107.2(2) . . . . ?
C24 C8 C12 O2 159.78(12) . . . . ?
C24 C8 C12 O6 -24.8(2) . . . . ?
C24 C21 C22 C23 120.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
