# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1038059'
_audit_update_record             
;
2014-12-06 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;

_audit_creation_date             2014-12-06T15:40:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
N-(3'-acetyl-17-oxospiro[19-norandrost-4-ene-3,2'-[1,3,4]-thiadiazoline]-5'-yl)acetamide
_chemical_name_common            
N-(3'-acetyl-17-oxospiro[19-norandrost-4-ene-3,2'-[1,3,4]-thiadiazoline]-5'-yl)acetamide
_chemical_formula_structural     'C23 H31 N3 O3 S'
_chemical_formula_moiety         'C23 H31 N3 O3 S'
_chemical_formula_sum            'C23 H31 N3 O3 S'
_chemical_formula_weight         429.57
_chemical_melting_point          468
_chemical_compound_source        synthetic
_chemical_absolute_configuration rm

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

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'I 4'
_symmetry_space_group_name_Hall  'I 4'
_symmetry_Int_Tables_number      79
_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.
;
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z'
'y, -x, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'

_cell_length_a                   21.9810(3)
_cell_length_b                   21.9810(3)
_cell_length_c                   10.9904(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5310.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6189
_cell_measurement_theta_min      3.81
_cell_measurement_theta_max      28.449

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    1.075
_exptl_crystal_F_000             1840

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

_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;  Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm using CrysAlisPro 
 (Agilent Technologies, 2014).
;
_exptl_absorpt_correction_T_min  0.97466
_exptl_absorpt_correction_T_max  1

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

_diffrn_source                   'fine focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) (Agilent Technologies)'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Sapphire3 (Agilent Technologies)'
_diffrn_detector_area_resol_mean 16.328
_diffrn_orient_matrix_ub_11      0.0218708
_diffrn_orient_matrix_ub_12      0.0188137
_diffrn_orient_matrix_ub_13      0.028911
_diffrn_orient_matrix_ub_21      0.0231871
_diffrn_orient_matrix_ub_22      -0.0211092
_diffrn_orient_matrix_ub_23      -0.0152089
_diffrn_orient_matrix_ub_31      0.0050224
_diffrn_orient_matrix_ub_32      0.0155421
_diffrn_orient_matrix_ub_33      -0.0556679
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Gemini S (Agilent Technologies)'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'glass fiber'
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_number            15692
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.342
_diffrn_reflns_theta_max         29.119
_diffrn_reflns_theta_full        26.32
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.902
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.86
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.814
_reflns_Friedel_coverage         0.816
_reflns_number_total             6161
_reflns_number_gt                4874
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'

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

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   mixed

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0940P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6161
_refine_ls_number_parameters     278
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1486
_refine_ls_wR_factor_gt          0.1386
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Absolute structure was assigned to match known absolute configuration 
 of the steroid core.

 Flack x = 0.05(12) determined by conventional TWIN/BASF refinement 
 (Flack, 1983).

 Flack x = 0.03(3) determined using post-refinement Parsons quotient 
 method (1931 quotients) (Parsons, Flack and Wagner, 2013) 

 Hooft y = 0.04(3) determined using 2769 Bijvoet pairs (9 outliers) 
 (Hooft, Stravera and Spek, 2008) using optimized Student's t-probability
 plot (ν = 99, corr. coeff. = 0.999) (Hooft, Stravera and Spek, 2009)
;
_refine_ls_abs_structure_Flack   0.05(12)
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.079

# SQUEEZE RESULTS
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material 168
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.116 278 24 dmso
2 0.000 0.500 -0.004 316 36 dmso
3 0.500 0.000 -0.005 316 36 dmso
4 0.500 0.500 0.384 278 24 dmso
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?


#----------------------------------------------------------------------------#
#                   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'
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 0.82419(3) 0.73301(3) 0.50506(9) 0.0425(2) Uani 1 1 d . . . . .
H H 0.9773(19) 0.7552(18) 0.510(4) 0.052(10) Uiso 1 1 d . . . . .
N N 0.94870(12) 0.73399(12) 0.5073(4) 0.0485(6) Uani 1 1 d . . . . .
O1 O 0.3942(2) 0.6515(3) 0.6435(5) 0.148(2) Uani 1 1 d . . . . .
O2 O 0.90735(15) 0.64129(13) 0.5013(6) 0.1073(13) Uani 1 1 d . . . . .
O3 O 0.78331(11) 0.93408(11) 0.4915(4) 0.0746(9) Uani 1 1 d . . . . .
N4' N 0.89881(10) 0.82530(11) 0.5007(3) 0.0461(6) Uani 1 1 d . . . . .
N3' N 0.84039(11) 0.85034(11) 0.4975(4) 0.0465(6) Uani 1 1 d . . . . .
C1 C 0.70396(15) 0.78039(18) 0.6576(3) 0.0471(8) Uani 1 1 d . . . . .
H1A H 0.6887 0.7843 0.74 0.057 Uiso 1 1 calc R U . . .
H1B H 0.7132 0.7378 0.6435 0.057 Uiso 1 1 calc R U . . .
C20 C 0.95227(17) 0.67305(16) 0.5050(6) 0.0715(11) Uani 1 1 d . . . . .
C2 C 0.76132(16) 0.81707(17) 0.6452(3) 0.0471(8) Uani 1 1 d . . . . .
H2A H 0.7906 0.8041 0.7059 0.057 Uiso 1 1 calc R U . . .
H2B H 0.7524 0.8598 0.6589 0.057 Uiso 1 1 calc R U . . .
C3 C 0.78811(13) 0.80881(13) 0.5190(3) 0.0392(7) Uani 1 1 d . . . . .
C4 C 0.74025(15) 0.81536(14) 0.4227(3) 0.0399(7) Uani 1 1 d . . . . .
H4 H 0.753 0.8219 0.3431 0.048 Uiso 1 1 calc R U . . .
C5 C 0.68111(15) 0.81251(15) 0.4435(3) 0.0382(7) Uani 1 1 d . . . . .
C6 C 0.63558(16) 0.82392(17) 0.3424(3) 0.0478(8) Uani 1 1 d . . . . .
H6A H 0.6564 0.8218 0.2647 0.057 Uiso 1 1 calc R U . . .
H6B H 0.6191 0.8646 0.351 0.057 Uiso 1 1 calc R U . . .
C7 C 0.58332(16) 0.77825(19) 0.3428(3) 0.0521(9) Uani 1 1 d . . . . .
H7A H 0.5532 0.7903 0.2829 0.063 Uiso 1 1 calc R U . . .
H7B H 0.5986 0.7384 0.3204 0.063 Uiso 1 1 calc R U . . .
C8 C 0.55365(15) 0.77471(15) 0.4671(3) 0.0435(8) Uani 1 1 d . . . . .
H8 H 0.5387 0.8153 0.4886 0.052 Uiso 1 1 calc R U . . .
C9 C 0.60133(13) 0.75542(15) 0.5627(3) 0.0396(7) Uani 1 1 d . . . . .
H9 H 0.6182 0.7165 0.5355 0.048 Uiso 1 1 calc R U . . .
C10 C 0.65468(14) 0.80064(15) 0.5687(3) 0.0398(7) Uani 1 1 d . . . . .
H10 H 0.6384 0.8393 0.5987 0.048 Uiso 1 1 calc R U . . .
C11 C 0.57394(16) 0.7445(2) 0.6893(3) 0.0551(9) Uani 1 1 d . . . . .
H11A H 0.6048 0.7265 0.7411 0.066 Uiso 1 1 calc R U . . .
H11B H 0.5628 0.7835 0.7244 0.066 Uiso 1 1 calc R U . . .
C12 C 0.51813(18) 0.7034(2) 0.6888(4) 0.0634(10) Uani 1 1 d . . . . .
H12A H 0.53 0.6623 0.6674 0.076 Uiso 1 1 calc R U . . .
H12B H 0.5002 0.7025 0.7694 0.076 Uiso 1 1 calc R U . . .
C13 C 0.47215(18) 0.7266(2) 0.5986(4) 0.0630(10) Uani 1 1 d . . . . .
C14 C 0.50074(16) 0.73098(18) 0.4720(3) 0.0538(9) Uani 1 1 d . . . . .
H14 H 0.5178 0.6907 0.455 0.065 Uiso 1 1 calc R U . . .
C15 C 0.4468(2) 0.7382(3) 0.3854(5) 0.0836(15) Uani 1 1 d . . . . .
H15A H 0.4573 0.7256 0.3034 0.1 Uiso 1 1 calc R U . . .
H15B H 0.4324 0.78 0.3836 0.1 Uiso 1 1 calc R U . . .
C16 C 0.3985(3) 0.6951(3) 0.4425(6) 0.0989(18) Uani 1 1 d . . . . .
H16A H 0.3585 0.7136 0.44 0.119 Uiso 1 1 calc R U . . .
H16B H 0.3971 0.6568 0.3989 0.119 Uiso 1 1 calc R U . . .
C17 C 0.4188(2) 0.6851(3) 0.5740(6) 0.0901(17) Uani 1 1 d . . . . .
C18 C 0.4428(2) 0.7870(3) 0.6423(6) 0.0917(17) Uani 1 1 d . . . . .
H18A H 0.41 0.7977 0.5889 0.138 Uiso 1 1 calc R U . . .
H18B H 0.4728 0.8187 0.6416 0.138 Uiso 1 1 calc R U . . .
H18C H 0.4275 0.7819 0.7235 0.138 Uiso 1 1 calc R U . . .
C5' C 0.89558(12) 0.76715(12) 0.5062(3) 0.0390(6) Uani 1 1 d . . . . .
C21 C 1.0162(2) 0.6489(2) 0.5082(10) 0.122(3) Uani 1 1 d . . . . .
H21A H 1.041 0.6714 0.4519 0.184 Uiso 1 1 calc R U . . .
H21B H 1.0162 0.6067 0.486 0.184 Uiso 1 1 calc R U . . .
H21C H 1.0324 0.6533 0.5889 0.184 Uiso 1 1 calc R U . . .
C22 C 0.83430(16) 0.91087(15) 0.4847(5) 0.0626(11) Uani 1 1 d . . . . .
C23 C 0.8903(2) 0.9470(2) 0.4567(7) 0.097(2) Uani 1 1 d . . . . .
H23A H 0.909 0.9314 0.3842 0.146 Uiso 1 1 calc R U . . .
H23B H 0.9183 0.9439 0.5234 0.146 Uiso 1 1 calc R U . . .
H23C H 0.8795 0.9889 0.4447 0.146 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   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' C5' 1.739(3) . y
S1' C3 1.852(3) . y
N C20 1.342(4) . y
N C5' 1.377(4) . y
N H 0.78(4) . ?
O1 C17 1.192(7) . y
O2 C20 1.210(5) . y
O3 C22 1.234(4) . y
N4' C5' 1.282(4) . y
N4' N3' 1.397(3) . y
N3' C22 1.345(4) . y
N3' C3 1.487(4) . y
C1 C2 1.503(5) . ?
C1 C10 1.525(5) . ?
C1 H1A 0.97 . ?
C1 H1B 0.97 . ?
C20 C21 1.503(6) . ?
C2 C3 1.517(5) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 C4 1.499(4) . ?
C4 C5 1.321(5) . y
C4 H4 0.93 . ?
C5 C10 1.515(4) . ?
C5 C6 1.517(4) . ?
C6 C7 1.526(5) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.516(5) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C14 1.510(5) . ?
C8 C9 1.544(4) . ?
C8 H8 0.98 . ?
C9 C11 1.535(5) . ?
C9 C10 1.539(4) . ?
C9 H9 0.98 . ?
C10 H10 0.98 . ?
C11 C12 1.524(6) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 C13 1.505(6) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C13 C17 1.510(6) . ?
C13 C14 1.529(6) . ?
C13 C18 1.553(7) . ?
C14 C15 1.530(6) . ?
C14 H14 0.98 . ?
C15 C16 1.554(7) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 C17 1.527(8) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C21 H21A 0.96 . ?
C21 H21B 0.96 . ?
C21 H21C 0.96 . ?
C22 C23 1.497(6) . ?
C23 H23A 0.96 . ?
C23 H23B 0.96 . ?
C23 H23C 0.96 . ?

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
C5' S1' C3 89.86(13) . . y
C20 N C5' 125.3(3) . . ?
C20 N H 123(3) . . ?
C5' N H 111(3) . . ?
C5' N4' N3' 110.1(2) . . ?
C22 N3' N4' 118.9(3) . . ?
C22 N3' C3 123.2(3) . . ?
N4' N3' C3 117.7(2) . . ?
C2 C1 C10 112.4(3) . . ?
C2 C1 H1A 109.1 . . ?
C10 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
C10 C1 H1B 109.1 . . ?
H1A C1 H1B 107.9 . . ?
O2 C20 N 121.9(3) . . ?
O2 C20 C21 124.1(4) . . ?
N C20 C21 113.9(4) . . ?
C1 C2 C3 110.2(3) . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
N3' C3 C4 111.8(3) . . ?
N3' C3 C2 111.8(3) . . ?
C4 C3 C2 111.2(3) . . y
N3' C3 S1' 102.01(17) . . y
C4 C3 S1' 109.2(2) . . ?
C2 C3 S1' 110.5(2) . . ?
C5 C4 C3 124.3(3) . . ?
C5 C4 H4 117.9 . . ?
C3 C4 H4 117.9 . . ?
C4 C5 C10 122.8(3) . . ?
C4 C5 C6 121.0(3) . . ?
C10 C5 C6 116.1(3) . . ?
C5 C6 C7 112.7(3) . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C6 111.2(3) . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108 . . ?
C14 C8 C7 113.3(3) . . ?
C14 C8 C9 108.9(3) . . ?
C7 C8 C9 109.6(3) . . ?
C14 C8 H8 108.3 . . ?
C7 C8 H8 108.3 . . ?
C9 C8 H8 108.3 . . ?
C11 C9 C10 111.2(3) . . ?
C11 C9 C8 113.2(3) . . ?
C10 C9 C8 111.6(3) . . ?
C11 C9 H9 106.8 . . ?
C10 C9 H9 106.8 . . ?
C8 C9 H9 106.8 . . ?
C5 C10 C1 111.1(2) . . ?
C5 C10 C9 111.4(2) . . ?
C1 C10 C9 112.3(3) . . ?
C5 C10 H10 107.2 . . ?
C1 C10 H10 107.2 . . ?
C9 C10 H10 107.2 . . ?
C12 C11 C9 113.9(3) . . ?
C12 C11 H11A 108.8 . . ?
C9 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C9 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 110.0(3) . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C12 C13 C17 115.9(4) . . ?
C12 C13 C14 110.2(3) . . ?
C17 C13 C14 101.2(4) . . ?
C12 C13 C18 111.3(4) . . ?
C17 C13 C18 104.4(4) . . ?
C14 C13 C18 113.4(4) . . ?
C8 C14 C13 112.9(3) . . ?
C8 C14 C15 120.6(3) . . ?
C13 C14 C15 104.7(3) . . ?
C8 C14 H14 105.9 . . ?
C13 C14 H14 105.9 . . ?
C15 C14 H14 105.9 . . ?
C14 C15 C16 102.3(4) . . ?
C14 C15 H15A 111.3 . . ?
C16 C15 H15A 111.3 . . ?
C14 C15 H15B 111.3 . . ?
C16 C15 H15B 111.3 . . ?
H15A C15 H15B 109.2 . . ?
C17 C16 C15 105.8(4) . . ?
C17 C16 H16A 110.6 . . ?
C15 C16 H16A 110.6 . . ?
C17 C16 H16B 110.6 . . ?
C15 C16 H16B 110.6 . . ?
H16A C16 H16B 108.7 . . ?
O1 C17 C13 127.6(6) . . ?
O1 C17 C16 124.4(5) . . ?
C13 C17 C16 108.0(4) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N4' C5' N 118.8(3) . . ?
N4' C5' S1' 118.7(2) . . ?
N C5' S1' 122.5(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O3 C22 N3' 119.6(3) . . ?
O3 C22 C23 122.7(3) . . ?
N3' C22 C23 117.7(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C5' N4' N3' C22 -176.3(4) . . . . y
C5' N4' N3' C3 8.8(5) . . . . ?
C5' N C20 O2 0.1(9) . . . . ?
C5' N C20 C21 -179.4(6) . . . . ?
C10 C1 C2 C3 -62.1(4) . . . . ?
C22 N3' C3 C4 55.4(5) . . . . ?
N4' N3' C3 C4 -129.9(3) . . . . ?
C22 N3' C3 C2 -70.0(5) . . . . ?
N4' N3' C3 C2 104.7(4) . . . . ?
C22 N3' C3 S1' 171.9(4) . . . . ?
N4' N3' C3 S1' -13.4(4) . . . . ?
C1 C2 C3 N3' 172.7(3) . . . . ?
C1 C2 C3 C4 47.0(4) . . . . ?
C1 C2 C3 S1' -74.4(3) . . . . ?
C5' S1' C3 N3' 10.8(3) . . . . ?
C5' S1' C3 C4 129.2(2) . . . . ?
C5' S1' C3 C2 -108.2(2) . . . . ?
N3' C3 C4 C5 -142.4(3) . . . . ?
C2 C3 C4 C5 -16.7(4) . . . . ?
S1' C3 C4 C5 105.5(3) . . . . ?
C3 C4 C5 C10 -1.5(5) . . . . y
C3 C4 C5 C6 175.8(3) . . . . ?
C4 C5 C6 C7 136.5(3) . . . . ?
C10 C5 C6 C7 -46.0(4) . . . . ?
C5 C6 C7 C8 52.5(4) . . . . ?
C6 C7 C8 C14 178.9(3) . . . . ?
C6 C7 C8 C9 -59.2(4) . . . . ?
C14 C8 C9 C11 -49.8(4) . . . . ?
C7 C8 C9 C11 -174.3(3) . . . . ?
C14 C8 C9 C10 -176.2(3) . . . . ?
C7 C8 C9 C10 59.3(4) . . . . ?
C4 C5 C10 C1 -11.3(5) . . . . ?
C6 C5 C10 C1 171.3(3) . . . . ?
C4 C5 C10 C9 -137.3(3) . . . . ?
C6 C5 C10 C9 45.3(4) . . . . ?
C2 C1 C10 C5 42.8(4) . . . . ?
C2 C1 C10 C9 168.3(3) . . . . ?
C11 C9 C10 C5 -178.9(3) . . . . ?
C8 C9 C10 C5 -51.4(4) . . . . ?
C11 C9 C10 C1 55.8(4) . . . . ?
C8 C9 C10 C1 -176.8(3) . . . . ?
C10 C9 C11 C12 176.1(3) . . . . ?
C8 C9 C11 C12 49.5(4) . . . . ?
C9 C11 C12 C13 -52.3(5) . . . . ?
C11 C12 C13 C17 170.9(4) . . . . ?
C11 C12 C13 C14 56.7(5) . . . . ?
C11 C12 C13 C18 -70.0(4) . . . . ?
C7 C8 C14 C13 178.6(3) . . . . ?
C9 C8 C14 C13 56.3(4) . . . . ?
C7 C8 C14 C15 -56.7(5) . . . . ?
C9 C8 C14 C15 -178.9(4) . . . . ?
C12 C13 C14 C8 -61.4(4) . . . . ?
C17 C13 C14 C8 175.4(3) . . . . ?
C18 C13 C14 C8 64.1(5) . . . . ?
C12 C13 C14 C15 165.5(4) . . . . ?
C17 C13 C14 C15 42.4(5) . . . . ?
C18 C13 C14 C15 -68.9(5) . . . . ?
C8 C14 C15 C16 -166.9(4) . . . . ?
C13 C14 C15 C16 -38.4(5) . . . . ?
C14 C15 C16 C17 19.3(7) . . . . ?
C12 C13 C17 O1 33.4(9) . . . . ?
C14 C13 C17 O1 152.6(7) . . . . ?
C18 C13 C17 O1 -89.4(8) . . . . ?
C12 C13 C17 C16 -148.9(5) . . . . ?
C14 C13 C17 C16 -29.7(6) . . . . ?
C18 C13 C17 C16 88.3(6) . . . . ?
C15 C16 C17 O1 -175.6(7) . . . . ?
C15 C16 C17 C13 6.7(7) . . . . ?
N3' N4' C5' N 178.5(3) . . . . y
N3' N4' C5' S1' 1.4(5) . . . . ?
C20 N C5' N4' -175.4(5) . . . . ?
C20 N C5' S1' 1.6(7) . . . . ?
C3 S1' C5' N4' -8.1(3) . . . . ?
C3 S1' C5' N 174.9(3) . . . . ?
N4' N3' C22 O3 -174.2(4) . . . . ?
C3 N3' C22 O3 0.4(7) . . . . ?
N4' N3' C22 C23 8.6(7) . . . . ?
C3 N3' C22 C23 -176.8(5) . . . . ?

#oooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooo#
#---------------------------- END OF CIF ------------------------------------#
#oooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooo#
# 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
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
_refine_special_details          SQUEEZE
