# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_17A
_database_code_depnum_ccdc_archive 'CCDC 1840501'
_audit_update_record             
;
2018-04-28 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;
_audit_creation_date             2018-03-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
(3'aR,6'R,6'aR,7R)-2',2'-dimethyl-octahydro-3'aH-spiro[[1,2,3]triazolo[4,3-c][1,4]oxazine-7,4'-furo[3,4-d][1,3]dioxol]-6'-ylmethanol
_chemical_formula_moiety         'C12 H17 N3 O5'
_chemical_formula_sum            'C12 H17 N3 O5'
_chemical_formula_weight         283.28
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H17N3O5

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.596(5)
_cell_length_b                   8.066(5)
_cell_length_c                   24.761(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1317.4(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4772
_cell_measurement_temperature    150.00(14)
_cell_measurement_theta_max      29.2134
_cell_measurement_theta_min      3.0079
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            13779
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.280
_diffrn_reflns_theta_min         3.014
_diffrn_ambient_temperature      150.00(14)
_diffrn_detector_area_resol_mean 16.2086
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -62.00   45.00   1.0000   17.2300
omega____ theta____ kappa____ phi______ frames
    -      -17.7198   19.0000    0.0000 107

#__ type_ start__ end____ width___ exp.time_
  2 omega  -37.00    2.00   1.0000   17.2300
omega____ theta____ kappa____ phi______ frames
    -      -17.7198   77.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
  3 omega  -86.00  -60.00   1.0000   17.2300
omega____ theta____ kappa____ phi______ frames
    -      -17.7198 -178.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -90.00    8.00   1.0000   17.2300
omega____ theta____ kappa____ phi______ frames
    -      -17.7198  -38.0000 -180.0000 98

#__ type_ start__ end____ width___ exp.time_
  5 omega  -94.00  -46.00   1.0000   17.2300
omega____ theta____ kappa____ phi______ frames
    -      -17.7198 -178.0000   90.0000 48

#__ type_ start__ end____ width___ exp.time_
  6 omega  -87.00    4.00   1.0000   17.2300
omega____ theta____ kappa____ phi______ frames
    -      -17.7198  -57.0000  -30.0000 91

#__ type_ start__ end____ width___ exp.time_
  7 omega   -4.00   61.00   1.0000   17.2300
omega____ theta____ kappa____ phi______ frames
    -       18.6573  -99.0000   90.0000 65

#__ type_ start__ end____ width___ exp.time_
  8 omega  -22.00   27.00   1.0000   17.2300
omega____ theta____ kappa____ phi______ frames
    -       18.6573   97.0000  158.0000 49
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1041648000
_diffrn_orient_matrix_UB_12      0.0085633000
_diffrn_orient_matrix_UB_13      0.0065570000
_diffrn_orient_matrix_UB_21      -0.0267111000
_diffrn_orient_matrix_UB_22      0.0294099000
_diffrn_orient_matrix_UB_23      0.0260245000
_diffrn_orient_matrix_UB_31      0.0013976000
_diffrn_orient_matrix_UB_32      -0.0825056000
_diffrn_orient_matrix_UB_33      0.0099328000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.844
_reflns_number_gt                2860
_reflns_number_total             3179
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_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    'SIR97 (Burla et al., 2007)'
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1004 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.091
_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)+(0.0315P)²+0.2114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0816
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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 0.5639(2) 0.08053(18) 0.62539(6) 0.0177(3) Uani 1 1 d . . . . .
O5 O 0.8527(3) -0.2952(2) 0.59669(7) 0.0266(4) Uani 1 1 d . . . . .
O4 O 0.4835(2) -0.17915(19) 0.71581(6) 0.0207(4) Uani 1 1 d . . . . .
O2 O 0.3205(3) 0.37634(19) 0.62376(7) 0.0260(4) Uani 1 1 d . . . . .
O3 O 0.1807(2) -0.0664(2) 0.69530(6) 0.0230(4) Uani 1 1 d . . . . .
N1 N 0.2877(3) 0.0958(2) 0.56506(7) 0.0188(4) Uani 1 1 d . . . . .
N2 N 0.2993(3) -0.0296(2) 0.52913(8) 0.0217(4) Uani 1 1 d . . . . .
N3 N 0.2484(3) 0.0330(2) 0.48217(7) 0.0229(4) Uani 1 1 d . . . . .
C4 C 0.6475(3) -0.0832(3) 0.63441(9) 0.0170(5) Uani 1 1 d . . . . .
C1 C 0.3498(3) 0.0768(3) 0.62210(8) 0.0173(5) Uani 1 1 d . . . . .
C12 C 0.2726(4) -0.0875(3) 0.78818(10) 0.0256(5) Uani 1 1 d . . . . .
C5 C 0.7358(4) -0.1536(3) 0.58253(10) 0.0221(5) Uani 1 1 d . . . . .
C9 C 0.2068(4) 0.1972(3) 0.48814(10) 0.0245(5) Uani 1 1 d . . . . .
C10 C 0.2778(4) -0.1714(3) 0.73402(9) 0.0199(5) Uani 1 1 d . . . . .
C6 C 0.2634(4) 0.2276(3) 0.65121(10) 0.0219(5) Uani 1 1 d . . . . .
C2 C 0.2791(3) -0.0917(3) 0.64475(8) 0.0182(5) Uani 1 1 d . . . . .
C8 C 0.2324(4) 0.2391(3) 0.54116(10) 0.0216(5) Uani 1 1 d . . . . .
C3 C 0.4759(3) -0.1851(3) 0.65829(9) 0.0173(4) Uani 1 1 d . . . . .
C11 C 0.1822(5) -0.3411(3) 0.73378(12) 0.0344(7) Uani 1 1 d . . . . .
C7 C 0.2115(5) 0.3930(3) 0.57457(11) 0.0331(6) Uani 1 1 d . . . . .
H6A H 0.319(4) 0.232(3) 0.6864(10) 0.011(6) Uiso 1 1 d . . . . .
H3 H 0.480(3) -0.296(3) 0.6457(8) 0.010(5) Uiso 1 1 d . . . . .
H4 H 0.756(4) -0.072(3) 0.6607(9) 0.013(6) Uiso 1 1 d . . . . .
H5A H 0.629(4) -0.179(3) 0.5571(10) 0.023(7) Uiso 1 1 d . . . . .
H2 H 0.193(4) -0.146(3) 0.6197(10) 0.019(6) Uiso 1 1 d . . . . .
H7A H 0.266(4) 0.491(4) 0.5566(11) 0.039(8) Uiso 1 1 d . . . . .
H7B H 0.065(5) 0.408(4) 0.5820(12) 0.042(8) Uiso 1 1 d . . . . .
H12A H 0.334(4) -0.155(3) 0.8156(10) 0.025(7) Uiso 1 1 d . . . . .
H11A H 0.052(5) -0.331(3) 0.7460(12) 0.039(8) Uiso 1 1 d . . . . .
H12B H 0.340(4) 0.019(3) 0.7867(11) 0.031(7) Uiso 1 1 d . . . . .
H5B H 0.825(4) -0.067(3) 0.5649(10) 0.024(6) Uiso 1 1 d . . . . .
H12C H 0.133(5) -0.073(3) 0.8004(11) 0.033(7) Uiso 1 1 d . . . . .
H6B H 0.112(4) 0.223(3) 0.6530(10) 0.025(7) Uiso 1 1 d . . . . .
H9 H 0.170(4) 0.261(3) 0.4586(11) 0.026(7) Uiso 1 1 d . . . . .
H11B H 0.183(5) -0.388(4) 0.6974(13) 0.048(9) Uiso 1 1 d . . . . .
H5 H 0.811(5) -0.375(4) 0.5737(13) 0.055(10) Uiso 1 1 d . . . . .
H11C H 0.261(5) -0.420(4) 0.7589(13) 0.061(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.448(3) . ?
O1 C1 1.415(3) . ?
O5 C5 1.422(3) . ?
O4 C10 1.431(3) . ?
O4 C3 1.426(3) . ?
O2 C6 1.429(3) . ?
O2 C7 1.421(3) . ?
O3 C10 1.431(3) . ?
O3 C2 1.424(3) . ?
N1 N2 1.349(3) . ?
N1 C1 1.478(3) . ?
N1 C8 1.349(3) . ?
N2 N3 1.311(3) . ?
N3 C9 1.361(3) . ?
C4 C5 1.520(3) . ?
C4 C3 1.518(3) . ?
C1 C6 1.524(3) . ?
C1 C2 1.543(3) . ?
C12 C10 1.503(3) . ?
C9 C8 1.366(3) . ?
C10 C11 1.507(4) . ?
C2 C3 1.538(3) . ?
C8 C7 1.498(3) . ?

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
C1 O1 C4 111.70(17) . . ?
C3 O4 C10 106.45(16) . . ?
C7 O2 C6 110.7(2) . . ?
C2 O3 C10 107.47(17) . . ?
N2 N1 C1 122.47(18) . . ?
N2 N1 C8 111.63(18) . . ?
C8 N1 C1 125.62(19) . . ?
N3 N2 N1 106.35(17) . . ?
N2 N3 C9 109.28(19) . . ?
O1 C4 C5 110.85(18) . . ?
O1 C4 C3 105.65(18) . . ?
C3 C4 C5 114.35(19) . . ?
O1 C1 N1 109.22(17) . . ?
O1 C1 C6 109.21(19) . . ?
O1 C1 C2 107.41(19) . . ?
N1 C1 C6 105.42(18) . . ?
N1 C1 C2 110.78(18) . . ?
C6 C1 C2 114.72(19) . . ?
O5 C5 C4 107.42(19) . . ?
N3 C9 C8 108.7(2) . . ?
O4 C10 C12 108.84(19) . . ?
O4 C10 C11 110.9(2) . . ?
O3 C10 O4 103.83(17) . . ?
O3 C10 C12 108.7(2) . . ?
O3 C10 C11 110.3(2) . . ?
C12 C10 C11 113.8(2) . . ?
O2 C6 C1 110.25(19) . . ?
O3 C2 C1 109.34(18) . . ?
O3 C2 C3 105.25(17) . . ?
C3 C2 C1 104.82(18) . . ?
N1 C8 C9 104.1(2) . . ?
N1 C8 C7 119.5(2) . . ?
C9 C8 C7 136.4(2) . . ?
O4 C3 C4 110.17(18) . . ?
O4 C3 C2 103.34(17) . . ?
C4 C3 C2 106.21(18) . . ?
O2 C7 C8 110.4(2) . . ?

_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_28B
_database_code_depnum_ccdc_archive 'CCDC 1840502'
_audit_update_record             
;
2018-04-28 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;
_audit_creation_date             2018-04-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
((6R,7S,8R)-7,8-dihydroxy-6-(hydroxymethyl)-5-oxa-2-azaspiro[3.4]octan-2-yl)(λ³-oxidaneylidyne)(p-tolyl)-λ⁷-sulfanone
_chemical_formula_moiety         'C14 H19 N O6 S'
_chemical_formula_sum            'C14 H19 N O6 S'
_chemical_formula_weight         329.37
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H19 N1 O6 S1'
_chemical_oxdiff_usercomment     ADI-7(2)-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 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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.1956(3)
_cell_length_b                   5.6323(2)
_cell_length_c                   20.3477(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.524(2)
_cell_angle_gamma                90
_cell_volume                     1511.74(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16846
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      70.1930
_cell_measurement_theta_min      3.3480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.180
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             700
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 1 0.0200
-1 0 -1 0.0200
1 0 -1 0.0250
-1 0 1 0.0250
0 1 0 0.0650
0 -1 0 0.0650

_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.04
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9991 0.0019 1.0014 0.1346 0.0313 -0.0270
-0.9991 -0.0019 -1.0014 -0.1346 -0.0313 0.0270
0.9994 -0.0001 -1.0033 0.0267 0.1350 -0.0015
-0.9994 0.0001 1.0033 -0.0267 -0.1350 0.0015
-0.0007 0.9980 -0.0020 0.0563 -0.0080 0.2670
0.0007 -0.9980 0.0020 -0.0563 0.0080 -0.2670

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14940
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.559
_diffrn_reflns_theta_min         3.350
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00  94.00   0.50    2.00    --    5.00  12.00 -98.00  356
  2  ω   -179.00  -1.00   0.50    2.00    --  -90.00  12.00 -98.00  356
  3  ω    -89.00  89.00   0.50    0.50    --    0.00  60.00  30.00  356
  4  ω    -84.00  94.00   0.50    2.00    --    5.00  14.00 150.00  356
  5  ω    -84.00  94.00   0.50    2.00    --    5.00  29.00 -30.00  356
  6  ω    -72.00   2.00   0.50    2.00    --    5.00  43.00  60.00  148
  7  ω    -34.00  -6.00   0.50    2.00    --    5.00  60.00  60.00   56
  8  ω    -32.00  -1.00   0.50    2.00    --  -90.00  43.00 150.00   62
  9  ω   -160.00-134.00   0.50    2.00    --  -90.00  60.00 150.00   52
 10  ω   -162.00-136.00   0.50    2.00    --  -90.00  43.00 150.00   52
 11  ω    -27.00  -1.00   0.50    2.00    --  -90.00  60.00 150.00   52
 12  ω   -179.00-133.00   0.50    2.00    --  -90.00  43.00  90.00   92
 13  ω    -26.00  -1.00   0.50    2.00    --  -90.00  60.00 120.00   50
 14  ω    -27.00  -1.00   0.50    2.00    --  -90.00  60.00  90.00   52
 15  ω    -35.00  -1.00   0.50    2.00    --  -90.00  43.00-180.00   68
 16  ω    -26.00  -1.00   0.50    2.00    --  -90.00  60.00-180.00   50
 17  ω    -52.00  -2.00   0.50    2.00    --  -90.00  60.00-150.00  100
 18  ω    -43.00  -1.00   0.50    2.00    --  -90.00  43.00 120.00   84
 19  ω   -105.00 -40.00   0.50    2.00    --  -90.00  43.00-180.00  130
 20  ω    -26.00  -1.00   0.50    2.00    --  -90.00  57.00 150.00   50
 21  ω   -144.00-110.00   0.50    2.00    --  -90.00  43.00-180.00   68
 22  ω   -178.00-129.00   0.50    2.00    --  -90.00  60.00-180.00   98
 23  ω    -27.00  -1.00   0.50    2.00    --  -90.00  57.00-180.00   52
 24  ω    -33.00  -1.00   0.50    2.00    --  -90.00  57.00-150.00   64
 25  ω    -28.00  -1.00   0.50    2.00    --  -90.00  57.00 120.00   54
 26  ω    -28.00  -2.00   0.50    2.00    --  -90.00  60.00-120.00   52
 27  ω    -27.00  -1.00   0.50    2.00    --  -90.00  57.00  90.00   52
 28  ω    -45.00 -19.00   0.50    2.00    --  -90.00  29.00 -60.00   52
 29  ω   -179.00  -4.00   0.50    2.00    --  -90.00  43.00-150.00  350
 30  ω   -175.00-127.00   0.50    2.00    --  -90.00  29.00 -60.00   96
 31  ω    -27.00  -1.00   0.50    2.00    --  -90.00  43.00  90.00   52
 32  ω    -34.00  -1.00   0.50    2.00    --  -90.00  57.00-120.00   66
 33  ω   -151.00-108.00   0.50    2.00    --  -90.00  60.00-150.00   86
 34  ω   -179.00  -2.00   0.50    2.00    --  -90.00  60.00 -90.00  354
 35  ω   -178.00  -1.00   0.50    2.00    --  -90.00  29.00 150.00  354
 36  ω   -178.00 -90.00   0.50    2.00    --  -90.00  60.00 120.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0807173000
_diffrn_orient_matrix_UB_12      0.0565296000
_diffrn_orient_matrix_UB_13      0.0538019000
_diffrn_orient_matrix_UB_21      0.0831918000
_diffrn_orient_matrix_UB_22      -0.0080478000
_diffrn_orient_matrix_UB_23      -0.0516820000
_diffrn_orient_matrix_UB_31      -0.0145408000
_diffrn_orient_matrix_UB_32      0.2674677000
_diffrn_orient_matrix_UB_33      -0.0129814000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                14053
_reflns_number_total             14940
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_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    ?
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.020(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         14940
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0871P)²+0.8068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1497
_refine_special_details          'Refined as a 4-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.425(4)
 0.3540(16) 0.1066(9) 0.114(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Ternary CH refined with riding coordinates:
3.b Secondary CH2 refined with riding coordinates:
3.c Aromatic/amide H refined with riding coordinates:
3.d Idealised Me refined as rotating group:
3.e Idealised tetrahedral OH refined as rotating group:

;
_atom_sites_solution_hydrogens   geom
_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
S1 S 0.17512(10) 0.0364(3) 0.16127(6) 0.0236(3) Uani 1 1 d . . . . .
S21 S 0.65190(11) -0.0414(3) 0.35293(6) 0.0250(3) Uani 1 1 d . . . . .
O1 O 0.1107(3) 0.1916(9) 0.19687(19) 0.0312(10) Uani 1 1 d . . . . .
O24 O 0.9846(4) -0.5258(10) 0.2778(2) 0.0386(11) Uani 1 1 d . . . . .
H24 H 1.040456 -0.568054 0.262783 0.058 Uiso 1 1 calc GR . . . .
O23 O 0.9598(3) -0.3141(9) 0.40550(17) 0.0293(10) Uani 1 1 d . . . . .
O3 O 0.4816(3) 0.2680(9) 0.09278(17) 0.0275(10) Uani 1 1 d . . . . .
O25 O 1.1735(3) -0.3365(10) 0.3081(2) 0.0387(12) Uani 1 1 d . . . . .
H25 H 1.182499 -0.307303 0.268160 0.058 Uiso 1 1 calc GR . . . .
O2 O 0.1674(3) -0.2167(8) 0.17115(19) 0.0285(9) Uani 1 1 d . . . . .
O21 O 0.5807(3) -0.1915(9) 0.31903(19) 0.0324(10) Uani 1 1 d . . . . .
O6 O 0.6039(4) 0.1228(10) -0.01709(19) 0.0402(13) Uani 1 1 d . . . . .
H6 H 0.563201 0.035824 -0.038531 0.060 Uiso 1 1 calc GR . . . .
O26 O 1.0951(4) -0.1733(10) 0.51383(19) 0.0400(12) Uani 1 1 d . . . . .
H26 H 1.082279 -0.059438 0.538916 0.060 Uiso 1 1 calc GR . . . .
O4 O 0.5328(4) 0.4979(10) 0.2131(2) 0.0418(12) Uani 1 1 d . . . . .
H4 H 0.556004 0.526264 0.251169 0.063 Uiso 1 1 calc GR . . . .
O5 O 0.7083(3) 0.2187(12) 0.1896(2) 0.0432(13) Uani 1 1 d . . . . .
H5 H 0.724247 0.153279 0.225479 0.065 Uiso 1 1 calc GR . . . .
O22 O 0.6425(3) 0.2119(9) 0.34688(19) 0.0315(10) Uani 1 1 d . . . . .
N21 N 0.7626(4) -0.1077(10) 0.3234(2) 0.0257(11) Uani 1 1 d . . . . .
N1 N 0.2915(4) 0.1047(10) 0.1821(2) 0.0239(11) Uani 1 1 d . . . . .
C6 C 0.1853(4) -0.0714(12) 0.0304(2) 0.0254(12) Uani 1 1 d . . . . .
H6A H 0.215587 -0.217041 0.043925 0.030 Uiso 1 1 calc R . . . .
C8 C 0.3361(5) 0.3407(12) 0.1657(3) 0.0269(13) Uani 1 1 d . . . . .
H8A H 0.338704 0.453745 0.202973 0.032 Uiso 1 1 calc R . . . .
H8B H 0.305734 0.415085 0.125764 0.032 Uiso 1 1 calc R . . . .
C33 C 1.0680(4) -0.2790(12) 0.4012(3) 0.0249(12) Uani 1 1 d . . . . .
H33 H 1.104059 -0.430857 0.411943 0.030 Uiso 1 1 calc R . . . .
C34 C 1.1031(5) -0.0883(13) 0.4483(3) 0.0306(14) Uani 1 1 d . . . . .
H34A H 1.174340 -0.045521 0.439822 0.037 Uiso 1 1 calc R . . . .
H34B H 1.060783 0.055514 0.442104 0.037 Uiso 1 1 calc R . . . .
C28 C 0.8055(5) -0.3533(12) 0.3337(3) 0.0285(13) Uani 1 1 d . . . . .
H28A H 0.800878 -0.455248 0.294080 0.034 Uiso 1 1 calc R . . . .
H28B H 0.779033 -0.436329 0.372518 0.034 Uiso 1 1 calc R . . . .
C7 C 0.1704(4) -0.0204(13) -0.0358(3) 0.0294(14) Uani 1 1 d . . . . .
H7 H 0.190865 -0.132287 -0.067766 0.035 Uiso 1 1 calc R . . . .
C4 C 0.1101(5) 0.3086(13) 0.0574(3) 0.0280(13) Uani 1 1 d . . . . .
H4A H 0.090008 0.421022 0.089335 0.034 Uiso 1 1 calc R . . . .
C9 C 0.3804(4) -0.0267(12) 0.1557(3) 0.0277(13) Uani 1 1 d . . . . .
H9A H 0.367589 -0.098012 0.111831 0.033 Uiso 1 1 calc R . . . .
H9B H 0.410814 -0.143541 0.186780 0.033 Uiso 1 1 calc R . . . .
C10 C 0.4367(4) 0.2132(12) 0.1542(2) 0.0242(12) Uani 1 1 d . . . . .
C30 C 0.9104(4) -0.2398(12) 0.3456(2) 0.0243(13) Uani 1 1 d . . . . .
C27 C 0.6029(5) -0.3856(13) 0.5223(3) 0.0314(14) Uani 1 1 d . . . . .
H27 H 0.574260 -0.532032 0.535661 0.038 Uiso 1 1 calc R . . . .
C3 C 0.0953(5) 0.3550(13) -0.0090(3) 0.0292(13) Uani 1 1 d . . . . .
H3 H 0.063734 0.499250 -0.022455 0.035 Uiso 1 1 calc R . . . .
C24 C 0.6872(4) 0.0435(13) 0.4837(3) 0.0273(12) Uani 1 1 d . . . . .
H24A H 0.715998 0.190008 0.470523 0.033 Uiso 1 1 calc R . . . .
C31 C 0.9882(5) -0.2830(13) 0.2934(3) 0.0277(13) Uani 1 1 d . . . . .
H31 H 0.974813 -0.182173 0.253674 0.033 Uiso 1 1 calc R . . . .
C25 C 0.6499(4) -0.1157(12) 0.4370(3) 0.0242(12) Uani 1 1 d . . . . .
C5 C 0.1551(4) 0.0944(12) 0.0768(3) 0.0234(12) Uani 1 1 d . . . . .
C14 C 0.6167(5) 0.0326(14) 0.0480(3) 0.0319(14) Uani 1 1 d . . . . .
H14A H 0.687940 -0.017243 0.055634 0.038 Uiso 1 1 calc R . . . .
H14B H 0.572763 -0.108204 0.053501 0.038 Uiso 1 1 calc R . . . .
C23 C 0.6819(5) -0.0137(13) 0.5498(3) 0.0320(15) Uani 1 1 d . . . . .
H23 H 0.707245 0.094965 0.581959 0.038 Uiso 1 1 calc R . . . .
C32 C 1.0868(5) -0.2109(13) 0.3294(3) 0.0277(13) Uani 1 1 d . . . . .
H32 H 1.097801 -0.035853 0.325591 0.033 Uiso 1 1 calc R . . . .
C22 C 0.6401(5) -0.2271(13) 0.5698(3) 0.0307(14) Uani 1 1 d . . . . .
C2 C 0.1258(5) 0.1933(13) -0.0563(3) 0.0298(14) Uani 1 1 d . . . . .
C26 C 0.6073(4) -0.3323(13) 0.4558(3) 0.0293(13) Uani 1 1 d . . . . .
H26A H 0.581762 -0.440743 0.423649 0.035 Uiso 1 1 calc R . . . .
C12 C 0.6102(4) 0.1417(14) 0.1686(3) 0.0302(14) Uani 1 1 d . . . . .
H12 H 0.606347 -0.035257 0.171395 0.036 Uiso 1 1 calc R . . . .
C13 C 0.5895(4) 0.2204(12) 0.0973(3) 0.0257(12) Uani 1 1 d . . . . .
H13 H 0.627944 0.369368 0.088372 0.031 Uiso 1 1 calc R . . . .
C29 C 0.8586(4) 0.0052(12) 0.3493(3) 0.0269(13) Uani 1 1 d . . . . .
H29A H 0.853935 0.068176 0.394576 0.032 Uiso 1 1 calc R . . . .
H29B H 0.887162 0.125271 0.319482 0.032 Uiso 1 1 calc R . . . .
C1 C 0.1104(6) 0.2449(17) -0.1286(3) 0.0434(18) Uani 1 1 d . . . . .
H1A H 0.173011 0.209996 -0.151535 0.065 Uiso 1 1 calc GR . . . .
H1B H 0.092856 0.412741 -0.134585 0.065 Uiso 1 1 calc GR . . . .
H1C H 0.055346 0.145624 -0.146521 0.065 Uiso 1 1 calc GR . . . .
C11 C 0.5215(5) 0.2518(13) 0.2048(3) 0.0297(14) Uani 1 1 d . . . . .
H11 H 0.508486 0.168790 0.247233 0.036 Uiso 1 1 calc R . . . .
C21 C 0.6356(6) -0.2858(18) 0.6421(3) 0.0473(19) Uani 1 1 d . . . . .
H21A H 0.589421 -0.175395 0.663444 0.071 Uiso 1 1 calc GR . . . .
H21B H 0.703541 -0.271223 0.662425 0.071 Uiso 1 1 calc GR . . . .
H21C H 0.611057 -0.448641 0.647437 0.071 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.430(4) . ?
S1 O2 1.444(5) . ?
S1 N1 1.629(5) . ?
S1 C5 1.763(5) . ?
S21 O21 1.428(4) . ?
S21 O22 1.437(5) . ?
S21 N21 1.637(5) . ?
S21 C25 1.763(6) . ?
O24 C31 1.404(9) . ?
O23 C33 1.446(7) . ?
O23 C30 1.430(7) . ?
O3 C10 1.431(6) . ?
O3 C13 1.449(7) . ?
O25 C32 1.422(7) . ?
O6 C14 1.424(7) . ?
O26 C34 1.423(7) . ?
O4 C11 1.404(9) . ?
O5 C12 1.420(7) . ?
N21 C28 1.507(8) . ?
N21 C29 1.502(7) . ?
N1 C8 1.495(8) . ?
N1 C9 1.498(7) . ?
C6 C7 1.386(7) . ?
C6 C5 1.393(8) . ?
C8 C10 1.532(8) . ?
C33 C34 1.505(9) . ?
C33 C32 1.536(7) . ?
C28 C30 1.538(9) . ?
C7 C2 1.398(10) . ?
C4 C3 1.384(8) . ?
C4 C5 1.397(9) . ?
C9 C10 1.542(9) . ?
C10 C11 1.517(8) . ?
C30 C31 1.517(8) . ?
C30 C29 1.542(9) . ?
C27 C22 1.394(9) . ?
C27 C26 1.389(9) . ?
C3 C2 1.392(9) . ?
C24 C25 1.386(8) . ?
C24 C23 1.387(8) . ?
C31 C32 1.531(8) . ?
C25 C26 1.401(10) . ?
C14 C13 1.509(8) . ?
C23 C22 1.388(10) . ?
C22 C21 1.512(8) . ?
C2 C1 1.508(8) . ?
C12 C13 1.533(8) . ?
C12 C11 1.531(9) . ?

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 119.2(3) . . ?
O1 S1 N1 107.0(3) . . ?
O1 S1 C5 107.8(3) . . ?
O2 S1 N1 105.5(3) . . ?
O2 S1 C5 108.0(3) . . ?
N1 S1 C5 109.1(2) . . ?
O21 S21 O22 119.5(3) . . ?
O21 S21 N21 105.7(3) . . ?
O21 S21 C25 107.6(3) . . ?
O22 S21 N21 105.7(3) . . ?
O22 S21 C25 108.4(3) . . ?
N21 S21 C25 109.8(3) . . ?
C30 O23 C33 109.7(4) . . ?
C10 O3 C13 109.4(4) . . ?
C28 N21 S21 119.6(4) . . ?
C29 N21 S21 121.9(4) . . ?
C29 N21 C28 91.7(4) . . ?
C8 N1 S1 121.7(4) . . ?
C8 N1 C9 92.4(4) . . ?
C9 N1 S1 122.1(4) . . ?
C7 C6 C5 118.9(6) . . ?
N1 C8 C10 88.0(5) . . ?
O23 C33 C34 110.2(5) . . ?
O23 C33 C32 106.1(4) . . ?
C34 C33 C32 111.9(5) . . ?
O26 C34 C33 109.1(6) . . ?
N21 C28 C30 88.5(5) . . ?
C6 C7 C2 121.0(6) . . ?
C3 C4 C5 119.1(6) . . ?
N1 C9 C10 87.5(5) . . ?
O3 C10 C8 114.4(5) . . ?
O3 C10 C9 114.7(5) . . ?
O3 C10 C11 104.3(5) . . ?
C8 C10 C9 89.3(5) . . ?
C11 C10 C8 117.1(5) . . ?
C11 C10 C9 117.3(5) . . ?
O23 C30 C28 113.7(5) . . ?
O23 C30 C31 104.3(5) . . ?
O23 C30 C29 114.4(5) . . ?
C28 C30 C29 89.0(4) . . ?
C31 C30 C28 116.5(5) . . ?
C31 C30 C29 119.1(5) . . ?
C26 C27 C22 120.9(6) . . ?
C4 C3 C2 121.0(6) . . ?
C25 C24 C23 119.2(6) . . ?
O24 C31 C30 107.1(5) . . ?
O24 C31 C32 112.9(5) . . ?
C30 C31 C32 101.8(4) . . ?
C24 C25 S21 119.8(5) . . ?
C24 C25 C26 121.0(5) . . ?
C26 C25 S21 119.2(4) . . ?
C6 C5 S1 119.9(5) . . ?
C6 C5 C4 121.0(5) . . ?
C4 C5 S1 119.1(4) . . ?
O6 C14 C13 110.1(6) . . ?
C24 C23 C22 121.0(6) . . ?
O25 C32 C33 108.5(5) . . ?
O25 C32 C31 113.7(5) . . ?
C31 C32 C33 103.4(5) . . ?
C27 C22 C21 120.8(6) . . ?
C23 C22 C27 119.2(5) . . ?
C23 C22 C21 120.0(6) . . ?
C7 C2 C1 120.1(6) . . ?
C3 C2 C7 119.0(5) . . ?
C3 C2 C1 120.9(7) . . ?
C27 C26 C25 118.7(6) . . ?
O5 C12 C13 109.6(5) . . ?
O5 C12 C11 115.7(5) . . ?
C11 C12 C13 102.7(5) . . ?
O3 C13 C14 109.7(5) . . ?
O3 C13 C12 105.3(4) . . ?
C14 C13 C12 112.8(6) . . ?
N21 C29 C30 88.5(5) . . ?
O4 C11 C10 107.3(5) . . ?
O4 C11 C12 112.2(6) . . ?
C10 C11 C12 100.0(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
S1 N1 C8 C10 -143.4(4) . . . . ?
S1 N1 C9 C10 143.0(4) . . . . ?
S21 N21 C28 C30 -140.2(4) . . . . ?
S21 N21 C29 C30 138.5(4) . . . . ?
S21 C25 C26 C27 -177.8(5) . . . . ?
O1 S1 N1 C8 -65.2(5) . . . . ?
O1 S1 N1 C9 178.3(4) . . . . ?
O1 S1 C5 C6 -162.1(5) . . . . ?
O1 S1 C5 C4 18.8(6) . . . . ?
O24 C31 C32 O25 35.4(7) . . . . ?
O24 C31 C32 C33 -82.0(6) . . . . ?
O23 C33 C34 O26 69.2(6) . . . . ?
O23 C33 C32 O25 -136.9(5) . . . . ?
O23 C33 C32 C31 -15.9(6) . . . . ?
O23 C30 C31 O24 80.5(6) . . . . ?
O23 C30 C31 C32 -38.3(6) . . . . ?
O23 C30 C29 N21 -127.0(5) . . . . ?
O3 C10 C11 O4 75.8(6) . . . . ?
O3 C10 C11 C12 -41.4(6) . . . . ?
O2 S1 N1 C8 166.9(4) . . . . ?
O2 S1 N1 C9 50.4(5) . . . . ?
O2 S1 C5 C6 -32.0(6) . . . . ?
O2 S1 C5 C4 148.8(5) . . . . ?
O21 S21 N21 C28 -63.8(5) . . . . ?
O21 S21 N21 C29 -176.9(4) . . . . ?
O21 S21 C25 C24 -160.6(5) . . . . ?
O21 S21 C25 C26 17.1(6) . . . . ?
O6 C14 C13 O3 67.8(6) . . . . ?
O6 C14 C13 C12 -175.1(5) . . . . ?
O5 C12 C13 O3 -146.8(5) . . . . ?
O5 C12 C13 C14 93.6(7) . . . . ?
O5 C12 C11 O4 44.6(7) . . . . ?
O5 C12 C11 C10 158.1(5) . . . . ?
O22 S21 N21 C28 168.6(4) . . . . ?
O22 S21 N21 C29 55.5(5) . . . . ?
O22 S21 C25 C24 -30.1(6) . . . . ?
O22 S21 C25 C26 147.6(5) . . . . ?
N21 S21 C25 C24 84.9(5) . . . . ?
N21 S21 C25 C26 -97.4(5) . . . . ?
N21 C28 C30 O23 127.6(5) . . . . ?
N21 C28 C30 C31 -111.0(5) . . . . ?
N21 C28 C30 C29 11.3(4) . . . . ?
N1 S1 C5 C6 82.1(5) . . . . ?
N1 S1 C5 C4 -97.0(5) . . . . ?
N1 C8 C10 O3 129.3(5) . . . . ?
N1 C8 C10 C9 12.3(4) . . . . ?
N1 C8 C10 C11 -108.3(6) . . . . ?
N1 C9 C10 O3 -128.9(5) . . . . ?
N1 C9 C10 C8 -12.3(4) . . . . ?
N1 C9 C10 C11 108.1(5) . . . . ?
C6 C7 C2 C3 -0.6(9) . . . . ?
C6 C7 C2 C1 -180.0(6) . . . . ?
C8 N1 C9 C10 12.6(4) . . . . ?
C8 C10 C11 O4 -51.7(7) . . . . ?
C8 C10 C11 C12 -168.9(5) . . . . ?
C33 O23 C30 C28 157.6(5) . . . . ?
C33 O23 C30 C31 29.7(6) . . . . ?
C33 O23 C30 C29 -102.2(6) . . . . ?
C34 C33 C32 O25 102.8(6) . . . . ?
C34 C33 C32 C31 -136.2(5) . . . . ?
C28 N21 C29 C30 11.6(4) . . . . ?
C28 C30 C31 O24 -45.7(7) . . . . ?
C28 C30 C31 C32 -164.5(5) . . . . ?
C28 C30 C29 N21 -11.4(4) . . . . ?
C7 C6 C5 S1 -178.9(4) . . . . ?
C7 C6 C5 C4 0.2(9) . . . . ?
C4 C3 C2 C7 1.2(9) . . . . ?
C4 C3 C2 C1 -179.5(6) . . . . ?
C9 N1 C8 C10 -12.7(4) . . . . ?
C9 C10 C11 O4 -156.1(5) . . . . ?
C9 C10 C11 C12 86.7(6) . . . . ?
C10 O3 C13 C14 118.9(5) . . . . ?
C10 O3 C13 C12 -2.8(6) . . . . ?
C30 O23 C33 C34 112.9(5) . . . . ?
C30 O23 C33 C32 -8.4(7) . . . . ?
C30 C31 C32 O25 150.0(5) . . . . ?
C30 C31 C32 C33 32.5(6) . . . . ?
C3 C4 C5 S1 179.4(5) . . . . ?
C3 C4 C5 C6 0.3(9) . . . . ?
C24 C25 C26 C27 -0.1(9) . . . . ?
C24 C23 C22 C27 -0.1(9) . . . . ?
C24 C23 C22 C21 179.7(6) . . . . ?
C31 C30 C29 N21 108.7(5) . . . . ?
C25 S21 N21 C28 51.9(5) . . . . ?
C25 S21 N21 C29 -61.2(5) . . . . ?
C25 C24 C23 C22 0.1(9) . . . . ?
C5 S1 N1 C8 51.1(5) . . . . ?
C5 S1 N1 C9 -65.4(5) . . . . ?
C5 C6 C7 C2 -0.1(9) . . . . ?
C5 C4 C3 C2 -1.0(9) . . . . ?
C23 C24 C25 S21 177.7(4) . . . . ?
C23 C24 C25 C26 0.0(9) . . . . ?
C32 C33 C34 O26 -173.0(5) . . . . ?
C22 C27 C26 C25 0.1(9) . . . . ?
C26 C27 C22 C23 0.0(9) . . . . ?
C26 C27 C22 C21 -179.8(6) . . . . ?
C13 O3 C10 C8 157.4(5) . . . . ?
C13 O3 C10 C9 -101.5(6) . . . . ?
C13 O3 C10 C11 28.2(6) . . . . ?
C13 C12 C11 O4 -74.7(6) . . . . ?
C13 C12 C11 C10 38.8(6) . . . . ?
C29 N21 C28 C30 -11.6(4) . . . . ?
C29 C30 C31 O24 -150.5(5) . . . . ?
C29 C30 C31 C32 90.7(6) . . . . ?
C11 C12 C13 O3 -23.3(6) . . . . ?
C11 C12 C13 C14 -143.0(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.593
_oxdiff_exptl_absorpt_empirical_full_min 0.758
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               4
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.425(4) 332 25111 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.3540(16) 15367 10424 nmt 1.0003 0.0001 0.0341 -0.0002 -1.0002 0.0000
-0.0028 0.0004 -1.0000
3 0.1066(9) 11505 14115 nmt 1.0003 -0.0001 0.0146 -0.0001 -0.9996 0.0003
-0.0486 -0.0007 -1.0001
4 0.114(4) 238 25226 nmt 0.9992 0.0037 -0.0098 0.0005 0.9982 -0.0000 0.0235
-0.0053 1.0009

_twin_special_details            
;
Component 2 rotated by 179.9928° 
 around [1.00 -0.00 -0.00] (reciprocal) or [1.00 -0.00 0.02] (direct)
Component 3 rotated by -179.9914° 
 around [1.00 -0.00 -0.02] (reciprocal) or [1.00 -0.00 0.01] (direct)
Component 4 rotated by 0.8780° 
 around [-0.22 -0.94 0.27] (reciprocal) or [-0.04 -1.00 0.02] (direct)
;
