# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a20210181_csa637
_database_code_depnum_ccdc_archive 'CCDC 2107402'
loop_
_audit_author_name
_audit_author_address
'Leire San Felices'
;Universidad el Pais Vasco
Spain
;
_audit_update_record             
;
2021-09-03 deposited with the CCDC.	2021-12-15 downloaded from the CCDC.
;

_audit_creation_date             2021-09-02T11:13:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C23 H20 N S, C F3 O3 S, C H3 O0.5'
_chemical_formula_sum            'C25 H23 F3 N O3.50 S2'
_chemical_formula_weight         514.56

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1139(10)
_cell_length_b                   11.7059(12)
_cell_length_c                   12.6851(14)
_cell_angle_alpha                109.356(9)
_cell_angle_beta                 100.318(9)
_cell_angle_gamma                106.611(9)
_cell_volume                     1166.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.01(10)
_cell_measurement_reflns_used    1117
_cell_measurement_theta_min      1.778
_cell_measurement_theta_max      22.896

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.407
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.058
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_F_000             534
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 -11 4 0.1756
-11 11 -4 0.0378
3 14 -5 0.1991
11 -11 4 0.0259
-1 1 16 0.0297
1 -1 -16 0.0281


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (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_correction_T_min  0.931
_exptl_absorpt_correction_T_max  0.985

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_ambient_temperature      150.01(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_source_voltage           50
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 16.2439
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0774428
_diffrn_orient_matrix_ub_12      0.0025471
_diffrn_orient_matrix_ub_13      0.0254227
_diffrn_orient_matrix_ub_21      -0.0109703
_diffrn_orient_matrix_ub_22      0.0211172
_diffrn_orient_matrix_ub_23      0.0562561
_diffrn_orient_matrix_ub_31      -0.0338311
_diffrn_orient_matrix_ub_32      -0.065836
_diffrn_orient_matrix_ub_33      -0.0074961
_diffrn_measurement_device       'four-circleκ-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.2095
_diffrn_reflns_number            7751
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.785
_diffrn_reflns_theta_max         26.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.949
_reflns_Friedel_coverage         0
_reflns_number_total             4588
_reflns_number_gt                2749
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00 -63.00   1.00    9.00    --  -23.50-155.00-133.00   26
  2  ω    -93.00 -67.00   1.00    9.00    --  -23.50 -57.00 -90.00   26
  3  ω    -54.00  38.00   1.00    9.00    --   24.74 -77.00  60.00   92
  4  ω     42.00 116.00   1.00    9.00    --   24.74-178.00-120.00   74
  5  ω    -55.00  66.00   1.00    9.00    --   24.74 -77.00 -60.00  121
  6  ω    -55.00  66.00   1.00    9.00    --   24.74 -77.00-180.00  121
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The ethanol molecule of crystallization present in the structure present
 s a disorder in the oxygen atom in two positions at 50% each.
  
 shelx_SHELXL_version_number            2018/3
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0346P)²+0.2450P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4588
_refine_ls_number_parameters     343
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0679
_refine_ls_wR_factor_ref         0.1502
_refine_ls_wR_factor_gt          0.1186
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.08

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.81135(12) 0.59001(10) 0.56342(9) 0.0261(3) Uani 1 1 d . . . . .
S1A S 0.02180(13) 0.79836(10) 0.26868(9) 0.0275(3) Uani 1 1 d . . . . .
F1A F 0.3248(3) 0.8473(3) 0.3622(2) 0.0532(8) Uani 1 1 d . . . . .
F2A F 0.1635(3) 0.6588(2) 0.3366(2) 0.0408(7) Uani 1 1 d . . . . .
F3A F 0.2212(4) 0.6920(3) 0.1909(2) 0.0573(8) Uani 1 1 d . . . . .
O1A O 0.0167(4) 0.8553(3) 0.3866(2) 0.0390(8) Uani 1 1 d . . . . .
O2A O -0.1106(4) 0.6791(3) 0.1940(3) 0.0452(9) Uani 1 1 d . . . . .
O3A O 0.0693(4) 0.8889(3) 0.2159(2) 0.0364(8) Uani 1 1 d . . . . .
N1 N 0.4576(4) 0.2444(3) 0.4247(3) 0.0196(7) Uani 1 1 d . . . . .
C1 C 0.8566(5) 0.5741(4) 0.4345(3) 0.0269(10) Uani 1 1 d . . . . .
H1 H 0.940131 0.639553 0.428118 0.032 Uiso 1 1 calc R . . . .
C2 C 0.7614(5) 0.4589(4) 0.3421(3) 0.0250(10) Uani 1 1 d . . . . .
H2 H 0.769938 0.434073 0.264889 0.03 Uiso 1 1 calc R . . . .
C3 C 0.6490(5) 0.3825(4) 0.3780(3) 0.0204(9) Uani 1 1 d . . . . .
C4 C 0.5163(5) 0.2486(4) 0.3196(3) 0.0216(9) Uani 1 1 d . . . . .
C5 C 0.3351(5) 0.1456(4) 0.4197(4) 0.0251(10) Uani 1 1 d . . . . .
H5 H 0.280039 0.070067 0.348625 0.03 Uiso 1 1 calc R . . . .
C6 C 0.2895(5) 0.1547(4) 0.5191(4) 0.0292(10) Uani 1 1 d . . . . .
H6 H 0.203132 0.084839 0.517425 0.035 Uiso 1 1 calc R . . . .
C7 C 0.3708(5) 0.2668(4) 0.6221(3) 0.0277(10) Uani 1 1 d . . . . .
H7 H 0.339552 0.273396 0.690747 0.033 Uiso 1 1 calc R . . . .
C8 C 0.4970(5) 0.3687(4) 0.6251(3) 0.0237(9) Uani 1 1 d . . . . .
H8 H 0.552407 0.445606 0.695049 0.028 Uiso 1 1 calc R . . . .
C9 C 0.5407(5) 0.3563(4) 0.5241(3) 0.0204(9) Uani 1 1 d . . . . .
C10 C 0.6595(5) 0.4395(4) 0.4934(3) 0.0209(9) Uani 1 1 d . . . . .
C11 C 0.5758(5) 0.1371(4) 0.2764(3) 0.0227(9) Uani 1 1 d . . . . .
C12 C 0.7161(5) 0.1420(4) 0.3460(3) 0.0281(10) Uani 1 1 d . . . . .
H12 H 0.771692 0.213448 0.419819 0.034 Uiso 1 1 calc R . . . .
C13 C 0.7757(5) 0.0446(4) 0.3093(4) 0.0292(10) Uani 1 1 d . . . . .
H13 H 0.872339 0.049792 0.357188 0.035 Uiso 1 1 calc R . . . .
C14 C 0.6940(5) -0.0608(4) 0.2022(4) 0.0334(11) Uani 1 1 d . . . . .
H14 H 0.734276 -0.128266 0.176217 0.04 Uiso 1 1 calc R . . . .
C15 C 0.5539(6) -0.0668(4) 0.1339(4) 0.0397(12) Uani 1 1 d . . . . .
H15 H 0.496842 -0.139463 0.061001 0.048 Uiso 1 1 calc R . . . .
C16 C 0.4950(5) 0.0321(4) 0.1703(4) 0.0340(11) Uani 1 1 d . . . . .
H16 H 0.398882 0.027275 0.121925 0.041 Uiso 1 1 calc R . . . .
C17 C 0.3818(5) 0.2420(4) 0.2306(3) 0.0219(9) Uani 1 1 d . . . . .
C18 C 0.2694(5) 0.2355(4) 0.1616(3) 0.0233(9) Uani 1 1 d . . . . .
C19 C 0.1278(5) 0.2273(4) 0.0781(3) 0.0253(10) Uani 1 1 d . . . . .
H19 H 0.13254 0.185701 -0.003283 0.03 Uiso 1 1 calc R . . . .
C20 C -0.0335(5) 0.1461(4) 0.0879(4) 0.0394(12) Uani 1 1 d D . . . .
H20A H -0.09769 0.072899 0.011178 0.047 Uiso 0.612(18) 1 calc R . P A 1
H20B H -0.011525 0.109212 0.146108 0.047 Uiso 0.612(18) 1 calc R . P A 1
H20C H -0.081153 0.056425 0.025764 0.047 Uiso 0.388(18) 1 calc R . P A 2
H20D H -0.020828 0.142525 0.165756 0.047 Uiso 0.388(18) 1 calc R . P A 2
C21 C -0.1237(9) 0.2291(6) 0.1237(9) 0.034(2) Uani 0.612(18) 1 d D U P A 1
H21A H -0.09752 0.270092 0.210098 0.041 Uiso 0.612(18) 1 calc R . P A 1
H21B H -0.240993 0.180061 0.088538 0.041 Uiso 0.612(18) 1 calc R . P A 1
C22 C -0.0649(9) 0.3274(11) 0.0755(10) 0.040(3) Uani 0.612(18) 1 d D U P A 1
H22A H -0.086342 0.406663 0.114972 0.048 Uiso 0.612(18) 1 calc R . P A 1
H22B H -0.120855 0.291381 -0.0095 0.048 Uiso 0.612(18) 1 calc R . P A 1
C23 C 0.1156(5) 0.3612(4) 0.0969(4) 0.0340(11) Uani 1 1 d D . . . .
H23A H 0.177701 0.426978 0.177465 0.041 Uiso 0.612(18) 1 calc R . P A 1
H23B H 0.152901 0.393629 0.039795 0.041 Uiso 0.612(18) 1 calc R . P A 1
H23C H 0.203033 0.429093 0.167547 0.041 Uiso 0.388(18) 1 calc R . P A 2
H23D H 0.132071 0.381337 0.028978 0.041 Uiso 0.388(18) 1 calc R . P A 2
C1A C 0.1907(5) 0.7460(4) 0.2888(4) 0.0300(10) Uani 1 1 d . . . . .
C21B C -0.1306(14) 0.2279(10) 0.0702(17) 0.047(4) Uani 0.388(18) 1 d D U P A 2
H21C H -0.18878 0.192917 -0.01433 0.056 Uiso 0.388(18) 1 calc R . P A 2
H21D H -0.212117 0.217928 0.112109 0.056 Uiso 0.388(18) 1 calc R . P A 2
C22B C -0.0365(13) 0.3677(12) 0.1106(16) 0.045(4) Uani 0.388(18) 1 d D U P A 2
H22C H -0.082268 0.406113 0.060646 0.053 Uiso 0.388(18) 1 calc R . P A 2
H22D H -0.027107 0.417211 0.193324 0.053 Uiso 0.388(18) 1 calc R . P A 2
O1D O 0.5834(9) 0.4839(7) 0.1166(7) 0.0622(13) Uani 0.5 1 d D . P B 1
C1D C 0.5159(8) 0.4439(5) 0.0098(6) 0.0622(13) Uani 1 1 d D . . . .
H1DA H 0.421(3) 0.382(4) -0.002(4) 0.071(18) Uiso 1 1 d D . . . .
H1DB H 0.561(8) 0.411(6) -0.045(6) 0.23(5) Uiso 1 1 d D . . . .
H1D H 0.65(2) 0.565(7) 0.161(4) 0.279 Uiso 0.5 1 d DR . P C 1
H1DC H 0.582(7) 0.465(11) 0.081(4) 0.279 Uiso 0.5 1 d DR . P D 2



#----------------------------------------------------------------------------#
#                   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 C1 1.722(4) . ?
S1 C10 1.714(4) . ?
S1A O1A 1.437(3) . ?
S1A O2A 1.433(3) . ?
S1A O3A 1.438(3) . ?
S1A C1A 1.820(4) . ?
F1A C1A 1.342(5) . ?
F2A C1A 1.339(5) . ?
F3A C1A 1.313(4) . ?
N1 C4 1.533(5) . ?
N1 C5 1.333(5) . ?
N1 C9 1.369(5) . ?
C1 H1 0.95 . ?
C1 C2 1.365(5) . ?
C2 H2 0.95 . ?
C2 C3 1.403(5) . ?
C3 C4 1.515(5) . ?
C3 C10 1.364(5) . ?
C4 C11 1.527(5) . ?
C4 C17 1.475(5) . ?
C5 H5 0.95 . ?
C5 C6 1.378(5) . ?
C6 H6 0.95 . ?
C6 C7 1.392(5) . ?
C7 H7 0.95 . ?
C7 C8 1.385(5) . ?
C8 H8 0.95 . ?
C8 C9 1.383(5) . ?
C9 C10 1.439(5) . ?
C11 C12 1.392(5) . ?
C11 C16 1.377(5) . ?
C12 H12 0.95 . ?
C12 C13 1.380(5) . ?
C13 H13 0.95 . ?
C13 C14 1.387(5) . ?
C14 H14 0.95 . ?
C14 C15 1.378(6) . ?
C15 H15 0.95 . ?
C15 C16 1.390(6) . ?
C16 H16 0.95 . ?
C17 C18 1.188(5) . ?
C18 C19 1.472(5) . ?
C19 H19 1 . ?
C19 C20 1.557(6) . ?
C19 C23 1.546(5) . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?
C20 H20C 0.99 . ?
C20 H20D 0.99 . ?
C20 C21 1.457(7) . ?
C20 C21B 1.519(9) . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
C21 C22 1.488(8) . ?
C22 H22A 0.99 . ?
C22 H22B 0.99 . ?
C22 C23 1.527(7) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C23 H23C 0.99 . ?
C23 H23D 0.99 . ?
C23 C22B 1.448(9) . ?
C21B H21C 0.99 . ?
C21B H21D 0.99 . ?
C21B C22B 1.469(9) . ?
C22B H22C 0.99 . ?
C22B H22D 0.99 . ?
O1D C1D 1.245(9) . ?
O1D H1D 0.891(10) . ?
C1D C1D 1.510(12) 2_665 ?
C1D H1DA 0.906(10) . ?
C1D H1DB 0.903(10) . ?
C1D H1DC 0.903(10) . ?

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
C10 S1 C1 90.09(19) . . ?
O1A S1A O3A 115.28(18) . . ?
O1A S1A C1A 102.43(19) . . ?
O2A S1A O1A 114.79(19) . . ?
O2A S1A O3A 115.17(18) . . ?
O2A S1A C1A 103.3(2) . . ?
O3A S1A C1A 103.4(2) . . ?
C5 N1 C4 124.1(3) . . ?
C5 N1 C9 123.3(3) . . ?
C9 N1 C4 112.5(3) . . ?
S1 C1 H1 123.1 . . ?
C2 C1 S1 113.9(3) . . ?
C2 C1 H1 123.1 . . ?
C1 C2 H2 125 . . ?
C1 C2 C3 110.1(4) . . ?
C3 C2 H2 125 . . ?
C2 C3 C4 135.4(3) . . ?
C10 C3 C2 114.2(4) . . ?
C10 C3 C4 110.3(3) . . ?
C3 C4 N1 99.3(3) . . ?
C3 C4 C11 113.9(3) . . ?
C11 C4 N1 109.0(3) . . ?
C17 C4 N1 107.3(3) . . ?
C17 C4 C3 112.4(3) . . ?
C17 C4 C11 113.7(3) . . ?
N1 C5 H5 120.5 . . ?
N1 C5 C6 119.0(4) . . ?
C6 C5 H5 120.5 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.6(4) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.4(4) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.7 . . ?
C9 C8 C7 118.6(4) . . ?
C9 C8 H8 120.7 . . ?
N1 C9 C8 119.1(4) . . ?
N1 C9 C10 106.5(3) . . ?
C8 C9 C10 134.4(4) . . ?
C3 C10 S1 111.8(3) . . ?
C3 C10 C9 111.3(3) . . ?
C9 C10 S1 136.9(3) . . ?
C12 C11 C4 119.1(3) . . ?
C16 C11 C4 121.9(4) . . ?
C16 C11 C12 119.0(4) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.0(4) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.8(4) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.3(4) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.9(4) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 C15 120.0(4) . . ?
C11 C16 H16 120 . . ?
C15 C16 H16 120 . . ?
C18 C17 C4 177.3(4) . . ?
C17 C18 C19 178.6(4) . . ?
C18 C19 H19 108.7 . . ?
C18 C19 C20 112.8(3) . . ?
C18 C19 C23 113.6(3) . . ?
C20 C19 H19 108.7 . . ?
C23 C19 H19 108.7 . . ?
C23 C19 C20 104.2(3) . . ?
C19 C20 H20A 109.7 . . ?
C19 C20 H20B 109.7 . . ?
C19 C20 H20C 111.9 . . ?
C19 C20 H20D 111.9 . . ?
H20A C20 H20B 108.2 . . ?
H20C C20 H20D 109.6 . . ?
C21 C20 C19 109.8(4) . . ?
C21 C20 H20A 109.7 . . ?
C21 C20 H20B 109.7 . . ?
C21B C20 C19 99.2(7) . . ?
C21B C20 H20C 111.9 . . ?
C21B C20 H20D 111.9 . . ?
C20 C21 H21A 111.6 . . ?
C20 C21 H21B 111.6 . . ?
C20 C21 C22 100.9(7) . . ?
H21A C21 H21B 109.4 . . ?
C22 C21 H21A 111.6 . . ?
C22 C21 H21B 111.6 . . ?
C21 C22 H22A 110.1 . . ?
C21 C22 H22B 110.1 . . ?
C21 C22 C23 108.0(6) . . ?
H22A C22 H22B 108.4 . . ?
C23 C22 H22A 110.1 . . ?
C23 C22 H22B 110.1 . . ?
C19 C23 H23A 111.5 . . ?
C19 C23 H23B 111.5 . . ?
C19 C23 H23C 108.8 . . ?
C19 C23 H23D 108.8 . . ?
C22 C23 C19 101.2(5) . . ?
C22 C23 H23A 111.5 . . ?
C22 C23 H23B 111.5 . . ?
H23A C23 H23B 109.3 . . ?
H23C C23 H23D 107.7 . . ?
C22B C23 C19 113.8(6) . . ?
C22B C23 H23C 108.8 . . ?
C22B C23 H23D 108.8 . . ?
F1A C1A S1A 110.7(3) . . ?
F2A C1A S1A 110.6(3) . . ?
F2A C1A F1A 106.9(3) . . ?
F3A C1A S1A 113.6(3) . . ?
F3A C1A F1A 107.5(4) . . ?
F3A C1A F2A 107.2(3) . . ?
C20 C21B H21C 108.5 . . ?
C20 C21B H21D 108.5 . . ?
H21C C21B H21D 107.5 . . ?
C22B C21B C20 115.1(9) . . ?
C22B C21B H21C 108.5 . . ?
C22B C21B H21D 108.5 . . ?
C23 C22B C21B 99.6(9) . . ?
C23 C22B H22C 111.9 . . ?
C23 C22B H22D 111.9 . . ?
C21B C22B H22C 111.9 . . ?
C21B C22B H22D 111.9 . . ?
H22C C22B H22D 109.6 . . ?
C1D O1D H1D 124.3(19) . . ?
O1D C1D C1D 106.8(7) . 2_665 ?
O1D C1D H1DA 103(3) . . ?
O1D C1D H1DB 123(7) . . ?
C1D C1D H1DA 109(4) 2_665 . ?
C1D C1D H1DB 106(7) 2_665 . ?
C1D C1D H1DC 115(8) 2_665 . ?
H1DA C1D H1DB 109(2) . . ?
H1DA C1D H1DC 109(3) . . ?
H1DB C1D H1DC 109(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 C3 0.2(5) . . . . ?
O1A S1A C1A F1A -57.7(3) . . . . ?
O1A S1A C1A F2A 60.6(3) . . . . ?
O1A S1A C1A F3A -178.8(3) . . . . ?
O2A S1A C1A F1A -177.2(3) . . . . ?
O2A S1A C1A F2A -58.9(3) . . . . ?
O2A S1A C1A F3A 61.7(4) . . . . ?
O3A S1A C1A F1A 62.5(3) . . . . ?
O3A S1A C1A F2A -179.2(3) . . . . ?
O3A S1A C1A F3A -58.7(3) . . . . ?
N1 C4 C11 C12 -69.3(4) . . . . ?
N1 C4 C11 C16 111.0(4) . . . . ?
N1 C5 C6 C7 0.6(6) . . . . ?
N1 C9 C10 S1 -178.1(3) . . . . ?
N1 C9 C10 C3 1.1(5) . . . . ?
C1 S1 C10 C3 0.7(3) . . . . ?
C1 S1 C10 C9 179.9(5) . . . . ?
C1 C2 C3 C4 -178.9(4) . . . . ?
C1 C2 C3 C10 0.4(5) . . . . ?
C2 C3 C4 N1 179.4(4) . . . . ?
C2 C3 C4 C11 63.6(6) . . . . ?
C2 C3 C4 C17 -67.4(6) . . . . ?
C2 C3 C10 S1 -0.8(5) . . . . ?
C2 C3 C10 C9 179.8(3) . . . . ?
C3 C4 C11 C12 40.6(5) . . . . ?
C3 C4 C11 C16 -139.1(4) . . . . ?
C4 N1 C5 C6 -177.8(3) . . . . ?
C4 N1 C9 C8 177.6(3) . . . . ?
C4 N1 C9 C10 -1.1(4) . . . . ?
C4 C3 C10 S1 178.7(3) . . . . ?
C4 C3 C10 C9 -0.8(5) . . . . ?
C4 C11 C12 C13 -178.8(4) . . . . ?
C4 C11 C16 C15 179.5(4) . . . . ?
C5 N1 C4 C3 178.0(4) . . . . ?
C5 N1 C4 C11 -62.6(5) . . . . ?
C5 N1 C4 C17 60.9(5) . . . . ?
C5 N1 C9 C8 0.2(6) . . . . ?
C5 N1 C9 C10 -178.5(4) . . . . ?
C5 C6 C7 C8 -0.1(6) . . . . ?
C6 C7 C8 C9 -0.4(6) . . . . ?
C7 C8 C9 N1 0.3(6) . . . . ?
C7 C8 C9 C10 178.6(4) . . . . ?
C8 C9 C10 S1 3.5(8) . . . . ?
C8 C9 C10 C3 -177.2(4) . . . . ?
C9 N1 C4 C3 0.6(4) . . . . ?
C9 N1 C4 C11 120.0(3) . . . . ?
C9 N1 C4 C17 -116.5(3) . . . . ?
C9 N1 C5 C6 -0.7(6) . . . . ?
C10 S1 C1 C2 -0.5(3) . . . . ?
C10 C3 C4 N1 0.1(4) . . . . ?
C10 C3 C4 C11 -115.6(4) . . . . ?
C10 C3 C4 C17 113.3(4) . . . . ?
C11 C12 C13 C14 -0.8(6) . . . . ?
C12 C11 C16 C15 -0.2(6) . . . . ?
C12 C13 C14 C15 -0.1(7) . . . . ?
C13 C14 C15 C16 0.9(7) . . . . ?
C14 C15 C16 C11 -0.7(7) . . . . ?
C16 C11 C12 C13 1.0(6) . . . . ?
C17 C4 C11 C12 171.0(4) . . . . ?
C17 C4 C11 C16 -8.7(5) . . . . ?
C18 C19 C20 C21 117.0(6) . . . . ?
C18 C19 C20 C21B 141.3(8) . . . . ?
C18 C19 C23 C22 -140.4(5) . . . . ?
C18 C19 C23 C22B -126.1(9) . . . . ?
C19 C20 C21 C22 28.1(9) . . . . ?
C19 C20 C21B C22B -29.8(18) . . . . ?
C19 C23 C22B C21B -13.8(16) . . . . ?
C20 C19 C23 C22 -17.3(6) . . . . ?
C20 C19 C23 C22B -3.0(9) . . . . ?
C20 C21 C22 C23 -40.6(11) . . . . ?
C20 C21B C22B C23 28(2) . . . . ?
C21 C22 C23 C19 36.5(10) . . . . ?
C23 C19 C20 C21 -6.6(6) . . . . ?
C23 C19 C20 C21B 17.7(8) . . . . ?


# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
