# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20190724_B_cyclo2_nakanish
_database_code_depnum_ccdc_archive 'CCDC 1943176'
loop_
_audit_author_name
_audit_author_address
'Keisuke Nakanishi'
;Department of Applied Chemistry, Faculty of Science and Engineering
Japan
;
_audit_update_record             
;
2019-07-25 deposited with the CCDC.	2019-12-10 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C20 H26 O3 S'
_chemical_formula_moiety         'C20 H26 O3 S'
_chemical_formula_weight         346.48
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.14999(13)
_cell_length_b                   12.6963(2)
_cell_length_c                   20.1516(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1829.33(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21350
_cell_measurement_theta_min      3.48
_cell_measurement_theta_max      68.27
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744.00
_exptl_absorpt_coefficient_mu    1.683
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.387
_exptl_absorpt_correction_T_max  0.603

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            20894
_diffrn_reflns_av_R_equivalents  0.0901
_diffrn_reflns_theta_max         68.178
_diffrn_reflns_theta_min         4.116
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3213
_reflns_number_gt                3191
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.688
_reflns_Friedel_fraction_max     0.932
_reflns_Friedel_fraction_full    0.935

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0967
_refine_ls_wR_factor_gt          0.0965
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3213
_refine_ls_number_parameters     217
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0629P)²+0.6196P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.52
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1296 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.078(10)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.53218(8) 0.41656(4) 0.36930(3) 0.01837(17) Uani 1 1 d . . . . .
O2 O 0.5852(3) 0.52462(14) 0.38010(9) 0.0253(4) Uani 1 1 d . . . . .
O3 O 0.6505(3) 0.33528(16) 0.39601(9) 0.0270(4) Uani 1 1 d . . . . .
O4 O 0.3091(3) 0.20675(14) 0.38362(9) 0.0281(4) Uani 1 1 d . . . . .
C5 C 0.2415(4) 0.2827(2) 0.41013(12) 0.0204(5) Uani 1 1 d . . . . .
C6 C 0.5524(4) 0.4827(2) 0.24048(13) 0.0229(5) Uani 1 1 d . . . . .
H6 H 0.5768 0.5491 0.2579 0.027 Uiso 1 1 calc R U . . .
C7 C 0.5161(3) 0.39817(19) 0.28245(12) 0.0185(5) Uani 1 1 d . . . . .
C8 C 0.0957(5) 0.3808(2) 0.49881(15) 0.0314(7) Uani 1 1 d . . . . .
H8A H -0.0281 0.4080 0.5085 0.038 Uiso 1 1 calc R U . . .
H8B H 0.1597 0.3677 0.5404 0.038 Uiso 1 1 calc R U . . .
C9 C 0.1380(4) 0.4715(2) 0.38748(13) 0.0234(6) Uani 1 1 d . . . . .
H9 H 0.0195 0.4353 0.3786 0.028 Uiso 1 1 calc R U . . .
C10 C 0.3046(4) 0.39566(19) 0.40154(12) 0.0184(5) Uani 1 1 d . . . . .
C11 C 0.2055(4) 0.4598(2) 0.45708(14) 0.0258(6) Uani 1 1 d . . . . .
C12 C 0.5519(4) 0.4670(2) 0.17230(13) 0.0272(6) Uani 1 1 d . . . . .
H12 H 0.5787 0.5227 0.1439 0.033 Uiso 1 1 calc R U . . .
C13 C 0.1587(4) 0.5766(2) 0.35085(15) 0.0278(6) Uani 1 1 d . . . . .
H13 H 0.2847 0.5798 0.3318 0.033 Uiso 1 1 calc R U . . .
C14 C 0.5119(4) 0.3692(2) 0.14688(14) 0.0302(7) Uani 1 1 d . . . . .
H14 H 0.5121 0.3590 0.1012 0.036 Uiso 1 1 calc R U . . .
C15 C 0.4759(4) 0.2992(2) 0.25666(13) 0.0278(6) Uani 1 1 d . . . . .
H15 H 0.4522 0.2428 0.2849 0.033 Uiso 1 1 calc R U . . .
C16 C 0.1404(5) 0.6649(2) 0.40265(18) 0.0429(9) Uani 1 1 d . . . . .
H16A H 0.1502 0.7327 0.3807 0.051 Uiso 1 1 calc R U . . .
H16B H 0.0182 0.6609 0.4234 0.051 Uiso 1 1 calc R U . . .
C17 C 0.4714(5) 0.2855(2) 0.18861(14) 0.0321(6) Uani 1 1 d . . . . .
H17 H 0.4411 0.2201 0.1708 0.038 Uiso 1 1 calc R U . . .
C18 C 0.0813(4) 0.2796(2) 0.45875(15) 0.0267(6) Uani 1 1 d . . . . .
H18A H 0.0916 0.2186 0.4875 0.032 Uiso 1 1 calc R U . . .
H18B H -0.0374 0.2763 0.4355 0.032 Uiso 1 1 calc R U . . .
C19 C 0.0161(4) 0.5826(2) 0.29379(17) 0.0380(8) Uani 1 1 d . . . . .
H19 H -0.1092 0.5755 0.3130 0.046 Uiso 1 1 calc R U . . .
C20 C 0.2907(6) 0.6566(2) 0.45558(17) 0.0430(9) Uani 1 1 d . . . . .
H20A H 0.2797 0.7160 0.4855 0.052 Uiso 1 1 calc R U . . .
H20B H 0.4125 0.6605 0.4345 0.052 Uiso 1 1 calc R U . . .
C21 C 0.2788(6) 0.5543(2) 0.49591(15) 0.0395(8) Uani 1 1 d . . . . .
H21 H 0.1818 0.5682 0.5291 0.047 Uiso 1 1 calc R U . . .
C22 C 0.0433(5) 0.4934(3) 0.24414(17) 0.0470(9) Uani 1 1 d . . . . .
H22A H 0.0378 0.4270 0.2669 0.056 Uiso 1 1 calc R U . . .
H22B H -0.0536 0.4962 0.2112 0.056 Uiso 1 1 calc R U . . .
H22C H 0.1630 0.5007 0.2230 0.056 Uiso 1 1 calc R U . . .
C23 C 0.4544(7) 0.5332(3) 0.53652(17) 0.0521(10) Uani 1 1 d . . . . .
H23A H 0.4908 0.5964 0.5592 0.062 Uiso 1 1 calc R U . . .
H23B H 0.4295 0.4788 0.5684 0.062 Uiso 1 1 calc R U . . .
H23C H 0.5535 0.5112 0.5076 0.062 Uiso 1 1 calc R U . . .
C24 C 0.0249(7) 0.6882(3) 0.2576(2) 0.0697(14) Uani 1 1 d . . . . .
H24A H 0.0078 0.7444 0.2888 0.084 Uiso 1 1 calc R U . . .
H24B H 0.1446 0.6954 0.2364 0.084 Uiso 1 1 calc R U . . .
H24C H -0.0720 0.6910 0.2246 0.084 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/6 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O3 1.439(2) . ?
S1 O2 1.4399(18) . ?
S1 C10 1.772(3) . ?
S1 C7 1.769(3) . ?
O4 C5 1.204(3) . ?
C5 C18 1.508(4) . ?
C5 C10 1.513(3) . ?
C6 C12 1.388(4) . ?
C6 C7 1.391(3) . ?
C6 H6 0.9300 . ?
C7 C15 1.390(4) . ?
C8 C11 1.526(4) . ?
C8 C18 1.521(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C11 1.491(4) . ?
C9 C13 1.533(3) . ?
C9 C10 1.558(4) . ?
C9 H9 0.9800 . ?
C10 C11 1.555(3) . ?
C11 C21 1.525(4) . ?
C12 C14 1.373(4) . ?
C12 H12 0.9300 . ?
C13 C19 1.539(4) . ?
C13 C16 1.537(4) . ?
C13 H13 0.9800 . ?
C14 C17 1.386(4) . ?
C14 H14 0.9300 . ?
C15 C17 1.383(4) . ?
C15 H15 0.9300 . ?
C16 C20 1.518(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C22 1.524(5) . ?
C19 C24 1.527(4) . ?
C19 H19 0.9800 . ?
C20 C21 1.535(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C23 1.522(6) . ?
C21 H21 0.9800 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O2 118.16(12) . . ?
O3 S1 C10 107.18(12) . . ?
O2 S1 C10 109.21(12) . . ?
O3 S1 C7 108.27(11) . . ?
O2 S1 C7 107.00(12) . . ?
C10 S1 C7 106.46(12) . . ?
O4 C5 C18 124.9(2) . . ?
O4 C5 C10 126.1(2) . . ?
C18 C5 C10 109.0(2) . . ?
C12 C6 C7 119.3(2) . . ?
C12 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C15 C7 C6 120.6(2) . . ?
C15 C7 S1 120.17(19) . . ?
C6 C7 S1 119.2(2) . . ?
C11 C8 C18 107.3(2) . . ?
C11 C8 H8A 110.3 . . ?
C18 C8 H8A 110.3 . . ?
C11 C8 H8B 110.3 . . ?
C18 C8 H8B 110.3 . . ?
H8A C8 H8B 108.5 . . ?
C11 C9 C13 120.5(2) . . ?
C11 C9 C10 61.30(17) . . ?
C13 C9 C10 123.5(2) . . ?
C11 C9 H9 113.9 . . ?
C13 C9 H9 113.9 . . ?
C10 C9 H9 113.9 . . ?
C5 C10 C11 106.2(2) . . ?
C5 C10 C9 112.2(2) . . ?
C11 C10 C9 57.22(17) . . ?
C5 C10 S1 117.23(18) . . ?
C11 C10 S1 127.16(19) . . ?
C9 C10 S1 122.90(18) . . ?
C9 C11 C8 114.7(3) . . ?
C9 C11 C21 121.1(2) . . ?
C8 C11 C21 114.3(2) . . ?
C9 C11 C10 61.48(17) . . ?
C8 C11 C10 106.7(2) . . ?
C21 C11 C10 128.6(3) . . ?
C14 C12 C6 120.0(2) . . ?
C14 C12 H12 120.0 . . ?
C6 C12 H12 120.0 . . ?
C9 C13 C19 109.8(2) . . ?
C9 C13 C16 107.5(2) . . ?
C19 C13 C16 114.5(2) . . ?
C9 C13 H13 108.3 . . ?
C19 C13 H13 108.3 . . ?
C16 C13 H13 108.3 . . ?
C12 C14 C17 120.7(3) . . ?
C12 C14 H14 119.7 . . ?
C17 C14 H14 119.7 . . ?
C7 C15 C17 119.3(2) . . ?
C7 C15 H15 120.4 . . ?
C17 C15 H15 120.4 . . ?
C20 C16 C13 111.4(2) . . ?
C20 C16 H16A 109.3 . . ?
C13 C16 H16A 109.3 . . ?
C20 C16 H16B 109.3 . . ?
C13 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C15 C17 C14 120.0(3) . . ?
C15 C17 H17 120.0 . . ?
C14 C17 H17 120.0 . . ?
C5 C18 C8 105.7(2) . . ?
C5 C18 H18A 110.6 . . ?
C8 C18 H18A 110.6 . . ?
C5 C18 H18B 110.6 . . ?
C8 C18 H18B 110.6 . . ?
H18A C18 H18B 108.7 . . ?
C22 C19 C24 109.5(3) . . ?
C22 C19 C13 111.7(2) . . ?
C24 C19 C13 111.9(3) . . ?
C22 C19 H19 107.9 . . ?
C24 C19 H19 107.9 . . ?
C13 C19 H19 107.9 . . ?
C16 C20 C21 113.1(3) . . ?
C16 C20 H20A 109.0 . . ?
C21 C20 H20A 109.0 . . ?
C16 C20 H20B 109.0 . . ?
C21 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C11 C21 C20 114.4(3) . . ?
C11 C21 C23 114.9(3) . . ?
C20 C21 C23 112.8(3) . . ?
C11 C21 H21 104.4 . . ?
C20 C21 H21 104.4 . . ?
C23 C21 H21 104.4 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C6 C7 C15 -1.3(4) . . . . ?
C12 C6 C7 S1 175.8(2) . . . . ?
O3 S1 C7 C15 48.5(3) . . . . ?
O2 S1 C7 C15 176.8(2) . . . . ?
C10 S1 C7 C15 -66.5(2) . . . . ?
O3 S1 C7 C6 -128.7(2) . . . . ?
O2 S1 C7 C6 -0.3(2) . . . . ?
C10 S1 C7 C6 116.4(2) . . . . ?
O4 C5 C10 C11 -167.6(3) . . . . ?
C18 C5 C10 C11 11.3(3) . . . . ?
O4 C5 C10 C9 131.8(3) . . . . ?
C18 C5 C10 C9 -49.4(3) . . . . ?
O4 C5 C10 S1 -18.7(4) . . . . ?
C18 C5 C10 S1 160.16(18) . . . . ?
C11 C9 C10 C5 95.4(2) . . . . ?
C13 C9 C10 C5 -155.2(2) . . . . ?
C13 C9 C10 C11 109.4(3) . . . . ?
C11 C9 C10 S1 -116.1(2) . . . . ?
C13 C9 C10 S1 -6.6(4) . . . . ?
O3 S1 C10 C5 -36.6(2) . . . . ?
O2 S1 C10 C5 -165.68(18) . . . . ?
C7 S1 C10 C5 79.1(2) . . . . ?
O3 S1 C10 C11 104.9(2) . . . . ?
O2 S1 C10 C11 -24.2(3) . . . . ?
C7 S1 C10 C11 -139.4(2) . . . . ?
O3 S1 C10 C9 176.3(2) . . . . ?
O2 S1 C10 C9 47.2(2) . . . . ?
C7 S1 C10 C9 -68.0(2) . . . . ?
C13 C9 C11 C8 149.7(2) . . . . ?
C10 C9 C11 C8 -96.3(2) . . . . ?
C13 C9 C11 C21 6.1(4) . . . . ?
C10 C9 C11 C21 120.1(3) . . . . ?
C13 C9 C11 C10 -114.0(3) . . . . ?
C18 C8 C11 C9 49.7(3) . . . . ?
C18 C8 C11 C21 -164.2(3) . . . . ?
C18 C8 C11 C10 -16.1(3) . . . . ?
C5 C10 C11 C9 -106.4(2) . . . . ?
S1 C10 C11 C9 108.8(2) . . . . ?
C5 C10 C11 C8 3.1(3) . . . . ?
C9 C10 C11 C8 109.4(3) . . . . ?
S1 C10 C11 C8 -141.7(2) . . . . ?
C5 C10 C11 C21 145.1(3) . . . . ?
C9 C10 C11 C21 -108.5(3) . . . . ?
S1 C10 C11 C21 0.3(4) . . . . ?
C7 C6 C12 C14 1.4(4) . . . . ?
C11 C9 C13 C19 -157.8(3) . . . . ?
C10 C9 C13 C19 128.3(3) . . . . ?
C11 C9 C13 C16 -32.7(3) . . . . ?
C10 C9 C13 C16 -106.6(3) . . . . ?
C6 C12 C14 C17 0.1(5) . . . . ?
C6 C7 C15 C17 -0.3(4) . . . . ?
S1 C7 C15 C17 -177.4(2) . . . . ?
C9 C13 C16 C20 60.3(3) . . . . ?
C19 C13 C16 C20 -177.5(3) . . . . ?
C7 C15 C17 C14 1.8(5) . . . . ?
C12 C14 C17 C15 -1.8(5) . . . . ?
O4 C5 C18 C8 157.7(3) . . . . ?
C10 C5 C18 C8 -21.2(3) . . . . ?
C11 C8 C18 C5 22.9(3) . . . . ?
C9 C13 C19 C22 -59.5(3) . . . . ?
C16 C13 C19 C22 179.6(3) . . . . ?
C9 C13 C19 C24 177.4(3) . . . . ?
C16 C13 C19 C24 56.5(4) . . . . ?
C13 C16 C20 C21 -62.4(3) . . . . ?
C9 C11 C21 C20 -4.7(4) . . . . ?
C8 C11 C21 C20 -148.4(3) . . . . ?
C10 C11 C21 C20 71.9(4) . . . . ?
C9 C11 C21 C23 -137.5(3) . . . . ?
C8 C11 C21 C23 78.8(4) . . . . ?
C10 C11 C21 C23 -60.9(4) . . . . ?
C16 C20 C21 C11 31.9(4) . . . . ?
C16 C20 C21 C23 165.8(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2014/6


####################################################################### 
# 
# 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_20190716_E_cyclo_nakanishi
_database_code_depnum_ccdc_archive 'CCDC 1943181'
loop_
_audit_author_name
_audit_author_address
'Keisuke Nakanishi'
;Department of Applied Chemistry, Faculty of Science and Engineering
Japan
;
_audit_update_record             
;
2019-07-25 deposited with the CCDC.	2019-12-10 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C20 H26 O3 S'
_chemical_formula_moiety         'C20 H26 O3 S'
_chemical_formula_weight         346.48
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      hexagonal
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           'P 61'
_space_group_IT_number           169
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -Y,+X-Y,1/3+Z
3 -X+Y,-X,2/3+Z
4 -X,-Y,1/2+Z
5 +Y,-X+Y,5/6+Z
6 +X-Y,+X,1/6+Z
#------------------------------------------------------------------------------
_cell_length_a                   8.0090(4)
_cell_length_b                   8.0090(4)
_cell_length_c                   49.0398(13)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                120.0000
_cell_volume                     2724.2(2)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    25268
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      68.15
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.700
_exptl_crystal_size_min          0.600
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1116.00
_exptl_absorpt_coefficient_mu    1.696
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.197
_exptl_absorpt_correction_T_max  0.362

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            31493
_diffrn_reflns_av_R_equivalents  0.0857
_diffrn_reflns_theta_max         68.205
_diffrn_reflns_theta_min         5.412
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_limit_l_max       58
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3339
_reflns_number_gt                3325
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.973
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0903
_refine_ls_wR_factor_gt          0.0902
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3339
_refine_ls_number_parameters     217
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0590P)²+0.1987P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.51
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1622 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.031(6)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.45540(9) 0.28503(9) 0.48775(2) 0.02037(17) Uani 1 1 d . . . . .
O2 O 0.3249(3) 0.2271(3) 0.51048(4) 0.0281(4) Uani 1 1 d . . . . .
O3 O 0.5492(3) 0.4826(3) 0.47908(4) 0.0318(5) Uani 1 1 d . . . . .
O4 O 0.8067(3) 0.3718(3) 0.45196(4) 0.0373(5) Uani 1 1 d . . . . .
C5 C 0.3256(4) 0.1379(4) 0.45966(5) 0.0243(6) Uani 1 1 d . . . . .
C6 C 0.7754(4) 0.2631(4) 0.47074(5) 0.0233(5) Uani 1 1 d . . . . .
C7 C 0.3300(5) -0.2941(4) 0.51420(6) 0.0327(6) Uani 1 1 d . . . . .
H7A H 0.2219 -0.3728 0.5257 0.039 Uiso 1 1 calc R U . . .
H7B H 0.2848 -0.2889 0.4963 0.039 Uiso 1 1 calc R U . . .
H7C H 0.4128 -0.3485 0.5132 0.039 Uiso 1 1 calc R U . . .
C8 C 0.7335(4) 0.2419(4) 0.52169(5) 0.0192(5) Uani 1 1 d . . . . .
H8 H 0.8731 0.2943 0.5206 0.023 Uiso 1 1 calc R U . . .
C9 C 0.4423(4) -0.0901(4) 0.52600(5) 0.0233(5) Uani 1 1 d . . . . .
H9 H 0.3550 -0.0376 0.5266 0.028 Uiso 1 1 calc R U . . .
C10 C 0.6411(4) 0.1083(4) 0.56753(5) 0.0282(6) Uani 1 1 d . . . . .
H10A H 0.7671 0.1231 0.5709 0.034 Uiso 1 1 calc R U . . .
H10B H 0.5884 0.1173 0.5849 0.034 Uiso 1 1 calc R U . . .
C11 C 0.6651(4) 0.2752(4) 0.54901(5) 0.0204(5) Uani 1 1 d . . . . .
H11 H 0.5392 0.2657 0.5466 0.025 Uiso 1 1 calc R U . . .
C12 C 0.6165(4) 0.0461(4) 0.50922(5) 0.0190(5) Uani 1 1 d . . . . .
C13 C 0.6349(4) 0.2226(3) 0.49375(4) 0.0167(5) Uani 1 1 d . . . . .
C14 C 0.1136(6) -0.0892(5) 0.41664(8) 0.0453(9) Uani 1 1 d . . . . .
H14 H 0.0416 -0.1647 0.4020 0.054 Uiso 1 1 calc R U . . .
C15 C 0.8084(4) 0.4758(4) 0.56016(6) 0.0270(6) Uani 1 1 d . . . . .
H15 H 0.9349 0.4851 0.5615 0.032 Uiso 1 1 calc R U . . .
C16 C 0.5097(5) -0.0917(4) 0.55537(6) 0.0329(7) Uani 1 1 d . . . . .
H16A H 0.3970 -0.1597 0.5669 0.039 Uiso 1 1 calc R U . . .
H16B H 0.5779 -0.1634 0.5556 0.039 Uiso 1 1 calc R U . . .
C17 C 0.8673(4) 0.1388(4) 0.47447(6) 0.0284(6) Uani 1 1 d . . . . .
H17A H 0.9938 0.2127 0.4827 0.034 Uiso 1 1 calc R U . . .
H17B H 0.8809 0.0894 0.4571 0.034 Uiso 1 1 calc R U . . .
C18 C 0.8269(5) 0.6322(5) 0.54035(6) 0.0369(7) Uani 1 1 d . . . . .
H18A H 0.8609 0.6083 0.5226 0.044 Uiso 1 1 calc R U . . .
H18B H 0.7061 0.6300 0.5393 0.044 Uiso 1 1 calc R U . . .
H18C H 0.9252 0.7562 0.5467 0.044 Uiso 1 1 calc R U . . .
C19 C 0.3811(5) 0.2044(5) 0.43345(6) 0.0328(6) Uani 1 1 d . . . . .
H19 H 0.4882 0.3250 0.4303 0.039 Uiso 1 1 calc R U . . .
C20 C 0.0589(5) -0.1555(5) 0.44278(8) 0.0430(9) Uani 1 1 d . . . . .
H20 H -0.0490 -0.2758 0.4458 0.052 Uiso 1 1 calc R U . . .
C21 C 0.2745(6) 0.0884(5) 0.41187(6) 0.0419(8) Uani 1 1 d . . . . .
H21 H 0.3115 0.1305 0.3941 0.050 Uiso 1 1 calc R U . . .
C22 C 0.7315(4) -0.0268(4) 0.49320(5) 0.0266(6) Uani 1 1 d . . . . .
H22A H 0.8046 -0.0608 0.5055 0.032 Uiso 1 1 calc R U . . .
H22B H 0.6456 -0.1396 0.4825 0.032 Uiso 1 1 calc R U . . .
C23 C 0.7542(5) 0.5121(5) 0.58855(7) 0.0423(8) Uani 1 1 d . . . . .
H23A H 0.7430 0.4136 0.6008 0.051 Uiso 1 1 calc R U . . .
H23B H 0.8523 0.6359 0.5950 0.051 Uiso 1 1 calc R U . . .
H23C H 0.6333 0.5097 0.5876 0.051 Uiso 1 1 calc R U . . .
C24 C 0.1650(4) -0.0424(4) 0.46470(7) 0.0314(6) Uani 1 1 d . . . . .
H24 H 0.1295 -0.0863 0.4825 0.038 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/6 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O3 1.435(2) . ?
S1 O2 1.437(2) . ?
S1 C13 1.767(3) . ?
S1 C5 1.773(3) . ?
O4 C6 1.204(3) . ?
C5 C19 1.377(4) . ?
C5 C24 1.394(4) . ?
C6 C13 1.510(3) . ?
C6 C17 1.516(4) . ?
C7 C9 1.531(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C12 1.497(4) . ?
C8 C11 1.520(3) . ?
C8 C13 1.550(3) . ?
C8 H8 0.9800 . ?
C9 C12 1.514(3) . ?
C9 C16 1.541(4) . ?
C9 H9 0.9800 . ?
C10 C16 1.531(4) . ?
C10 C11 1.546(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C15 1.534(4) . ?
C11 H11 0.9800 . ?
C12 C22 1.532(3) . ?
C12 C13 1.544(3) . ?
C14 C20 1.373(6) . ?
C14 C21 1.381(6) . ?
C14 H14 0.9300 . ?
C15 C23 1.529(4) . ?
C15 C18 1.533(4) . ?
C15 H15 0.9800 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C22 1.530(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C21 1.385(4) . ?
C19 H19 0.9300 . ?
C20 C24 1.389(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24 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
O3 S1 O2 118.74(12) . . ?
O3 S1 C13 108.07(13) . . ?
O2 S1 C13 110.03(11) . . ?
O3 S1 C5 108.20(13) . . ?
O2 S1 C5 107.36(14) . . ?
C13 S1 C5 103.35(12) . . ?
C19 C5 C24 121.2(3) . . ?
C19 C5 S1 120.0(2) . . ?
C24 C5 S1 118.8(2) . . ?
O4 C6 C13 126.2(3) . . ?
O4 C6 C17 125.0(2) . . ?
C13 C6 C17 108.8(2) . . ?
C9 C7 H7A 109.5 . . ?
C9 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C9 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C12 C8 C11 116.9(2) . . ?
C12 C8 C13 60.89(15) . . ?
C11 C8 C13 125.9(2) . . ?
C12 C8 H8 114.1 . . ?
C11 C8 H8 114.1 . . ?
C13 C8 H8 114.1 . . ?
C12 C9 C7 113.7(2) . . ?
C12 C9 C16 108.3(2) . . ?
C7 C9 C16 111.5(2) . . ?
C12 C9 H9 107.7 . . ?
C7 C9 H9 107.7 . . ?
C16 C9 H9 107.7 . . ?
C16 C10 C11 113.5(2) . . ?
C16 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C16 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C8 C11 C15 110.6(2) . . ?
C8 C11 C10 105.4(2) . . ?
C15 C11 C10 113.6(2) . . ?
C8 C11 H11 109.0 . . ?
C15 C11 H11 109.0 . . ?
C10 C11 H11 109.0 . . ?
C8 C12 C9 113.7(2) . . ?
C8 C12 C22 115.4(2) . . ?
C9 C12 C22 121.1(2) . . ?
C8 C12 C13 61.25(15) . . ?
C9 C12 C13 123.9(2) . . ?
C22 C12 C13 107.25(19) . . ?
C6 C13 C12 106.5(2) . . ?
C6 C13 C8 110.6(2) . . ?
C12 C13 C8 57.86(15) . . ?
C6 C13 S1 116.02(17) . . ?
C12 C13 S1 128.45(19) . . ?
C8 C13 S1 124.40(17) . . ?
C20 C14 C21 120.6(3) . . ?
C20 C14 H14 119.7 . . ?
C21 C14 H14 119.7 . . ?
C23 C15 C18 110.0(3) . . ?
C23 C15 C11 112.9(3) . . ?
C18 C15 C11 110.2(2) . . ?
C23 C15 H15 107.8 . . ?
C18 C15 H15 107.8 . . ?
C11 C15 H15 107.8 . . ?
C10 C16 C9 114.6(2) . . ?
C10 C16 H16A 108.6 . . ?
C9 C16 H16A 108.6 . . ?
C10 C16 H16B 108.6 . . ?
C9 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C6 C17 C22 105.9(2) . . ?
C6 C17 H17A 110.6 . . ?
C22 C17 H17A 110.6 . . ?
C6 C17 H17B 110.6 . . ?
C22 C17 H17B 110.6 . . ?
H17A C17 H17B 108.7 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C5 C19 C21 118.8(3) . . ?
C5 C19 H19 120.6 . . ?
C21 C19 H19 120.6 . . ?
C14 C20 C24 119.9(3) . . ?
C14 C20 H20 120.1 . . ?
C24 C20 H20 120.1 . . ?
C19 C21 C14 120.4(3) . . ?
C19 C21 H21 119.8 . . ?
C14 C21 H21 119.8 . . ?
C17 C22 C12 106.2(2) . . ?
C17 C22 H22A 110.5 . . ?
C12 C22 H22A 110.5 . . ?
C17 C22 H22B 110.5 . . ?
C12 C22 H22B 110.5 . . ?
H22A C22 H22B 108.7 . . ?
C15 C23 H23A 109.5 . . ?
C15 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C15 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C24 C5 119.0(3) . . ?
C20 C24 H24 120.5 . . ?
C5 C24 H24 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 S1 C5 C19 24.5(3) . . . . ?
O2 S1 C5 C19 153.8(2) . . . . ?
C13 S1 C5 C19 -89.9(2) . . . . ?
O3 S1 C5 C24 -153.8(2) . . . . ?
O2 S1 C5 C24 -24.5(3) . . . . ?
C13 S1 C5 C24 91.7(2) . . . . ?
C12 C8 C11 C15 175.3(2) . . . . ?
C13 C8 C11 C15 -112.5(3) . . . . ?
C12 C8 C11 C10 52.1(3) . . . . ?
C13 C8 C11 C10 124.3(3) . . . . ?
C16 C10 C11 C8 -54.5(3) . . . . ?
C16 C10 C11 C15 -175.7(2) . . . . ?
C11 C8 C12 C9 1.0(3) . . . . ?
C13 C8 C12 C9 -117.1(2) . . . . ?
C11 C8 C12 C22 -145.4(2) . . . . ?
C13 C8 C12 C22 96.6(2) . . . . ?
C11 C8 C12 C13 118.0(2) . . . . ?
C7 C9 C12 C8 -176.3(2) . . . . ?
C16 C9 C12 C8 -51.8(3) . . . . ?
C7 C9 C12 C22 -32.0(3) . . . . ?
C16 C9 C12 C22 92.4(3) . . . . ?
C7 C9 C12 C13 113.5(3) . . . . ?
C16 C9 C12 C13 -122.1(3) . . . . ?
O4 C6 C13 C12 168.9(3) . . . . ?
C17 C6 C13 C12 -9.2(3) . . . . ?
O4 C6 C13 C8 -129.9(3) . . . . ?
C17 C6 C13 C8 52.1(3) . . . . ?
O4 C6 C13 S1 18.9(4) . . . . ?
C17 C6 C13 S1 -159.19(18) . . . . ?
C8 C12 C13 C6 104.3(2) . . . . ?
C9 C12 C13 C6 -155.1(2) . . . . ?
C22 C12 C13 C6 -5.6(3) . . . . ?
C9 C12 C13 C8 100.5(3) . . . . ?
C22 C12 C13 C8 -110.0(2) . . . . ?
C8 C12 C13 S1 -110.7(2) . . . . ?
C9 C12 C13 S1 -10.1(3) . . . . ?
C22 C12 C13 S1 139.4(2) . . . . ?
C12 C8 C13 C6 -97.0(2) . . . . ?
C11 C8 C13 C6 159.4(2) . . . . ?
C11 C8 C13 C12 -103.6(3) . . . . ?
C12 C8 C13 S1 117.4(2) . . . . ?
C11 C8 C13 S1 13.7(4) . . . . ?
O3 S1 C13 C6 -52.7(2) . . . . ?
O2 S1 C13 C6 176.20(19) . . . . ?
C5 S1 C13 C6 61.8(2) . . . . ?
O3 S1 C13 C12 165.0(2) . . . . ?
O2 S1 C13 C12 33.9(2) . . . . ?
C5 S1 C13 C12 -80.5(2) . . . . ?
O3 S1 C13 C8 91.3(2) . . . . ?
O2 S1 C13 C8 -39.8(2) . . . . ?
C5 S1 C13 C8 -154.2(2) . . . . ?
C8 C11 C15 C23 -176.0(2) . . . . ?
C10 C11 C15 C23 -57.7(3) . . . . ?
C8 C11 C15 C18 60.5(3) . . . . ?
C10 C11 C15 C18 178.8(2) . . . . ?
C11 C10 C16 C9 5.7(4) . . . . ?
C12 C9 C16 C10 48.1(3) . . . . ?
C7 C9 C16 C10 173.9(3) . . . . ?
O4 C6 C17 C22 -157.7(3) . . . . ?
C13 C6 C17 C22 20.4(3) . . . . ?
C24 C5 C19 C21 -0.2(4) . . . . ?
S1 C5 C19 C21 -178.5(2) . . . . ?
C21 C14 C20 C24 0.6(5) . . . . ?
C5 C19 C21 C14 1.1(5) . . . . ?
C20 C14 C21 C19 -1.3(5) . . . . ?
C6 C17 C22 C12 -23.5(3) . . . . ?
C8 C12 C22 C17 -47.7(3) . . . . ?
C9 C12 C22 C17 168.6(2) . . . . ?
C13 C12 C22 C17 18.1(3) . . . . ?
C14 C20 C24 C5 0.3(4) . . . . ?
C19 C5 C24 C20 -0.5(4) . . . . ?
S1 C5 C24 C20 177.8(2) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2014/6


