# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_15
_database_code_depnum_ccdc_archive 'CCDC 1962767'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2019-10-31 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;

_audit_creation_date             2017-04-03T14:45:38-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C19 H27 N O3 S'
_chemical_formula_sum            'C19 H27 N O3 S'
_chemical_formula_weight         349.47

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.5390(3)
_cell_length_b                   15.4431(4)
_cell_length_c                   11.3497(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.2140(10)
_cell_angle_gamma                90
_cell_volume                     1782.48(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8852
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      31.32

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             752

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

_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.545
_exptl_absorpt_correction_T_max  0.6481

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

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_number            21884
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         31.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.947
_reflns_Friedel_coverage         0
_reflns_number_total             5620
_reflns_number_gt                4768
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   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)+(0.0600P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5620
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.045
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1025
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.065

#----------------------------------------------------------------------------#
#                   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 0.33692(2) 0.08204(2) 0.38650(2) 0.01374(7) Uani 1 1 d . . . . .
O1 O 0.21999(7) 0.13402(5) 0.36629(7) 0.01815(16) Uani 1 1 d . . . . .
O2 O 0.44346(7) 0.09917(5) 0.49403(7) 0.01810(16) Uani 1 1 d . . . . .
O3 O 0.57296(9) 0.13374(6) -0.02509(8) 0.02516(18) Uani 1 1 d . . . . .
N1 N 0.30081(8) -0.01844(6) 0.39666(8) 0.01477(17) Uani 1 1 d . . . . .
C1 C 0.18545(9) -0.06481(6) 0.31817(9) 0.01274(17) Uani 1 1 d . . . . .
C2 C 0.21670(10) -0.16179(6) 0.33615(10) 0.01568(19) Uani 1 1 d . . . . .
C3 C 0.10134(10) -0.21661(7) 0.26164(10) 0.01719(19) Uani 1 1 d . . . . .
C4 C -0.02201(10) -0.19482(7) 0.30387(10) 0.01717(19) Uani 1 1 d . . . . .
C5 C -0.05607(10) -0.09814(7) 0.28817(10) 0.01540(18) Uani 1 1 d . . . . .
C6 C 0.06244(10) -0.04549(6) 0.36206(9) 0.01436(18) Uani 1 1 d . . . . .
C7 C 0.15955(10) -0.04199(7) 0.18201(10) 0.01681(19) Uani 1 1 d . . . . .
C8 C 0.04201(11) -0.09528(7) 0.10854(10) 0.0181(2) Uani 1 1 d . . . . .
C9 C 0.07422(11) -0.19188(7) 0.12640(10) 0.0198(2) Uani 1 1 d . . . . .
C10 C -0.08027(10) -0.07437(7) 0.15254(10) 0.0177(2) Uani 1 1 d . . . . .
C11 C 0.13360(13) -0.31287(8) 0.27910(13) 0.0275(3) Uani 1 1 d . . . . .
C12 C -0.17634(11) -0.07826(8) 0.33446(12) 0.0237(2) Uani 1 1 d . . . . .
C13 C 0.40122(10) 0.09660(6) 0.25895(10) 0.01518(19) Uani 1 1 d . . . . .
C14 C 0.35095(10) 0.16099(7) 0.17437(10) 0.0180(2) Uani 1 1 d . . . . .
C15 C 0.40643(11) 0.17640(7) 0.07752(10) 0.0194(2) Uani 1 1 d . . . . .
C16 C 0.51082(11) 0.12504(7) 0.06515(10) 0.0184(2) Uani 1 1 d . . . . .
C17 C 0.55969(11) 0.05904(7) 0.14961(11) 0.0209(2) Uani 1 1 d . . . . .
C18 C 0.50642(11) 0.04512(7) 0.24677(11) 0.0191(2) Uani 1 1 d . . . . .
C19 C 0.52536(14) 0.19976(9) -0.11375(12) 0.0277(3) Uani 1 1 d . . . . .
H1 H 0.3738(17) -0.0480(12) 0.4326(16) 0.031(4) Uiso 1 1 d . . . . .
H2 H 0.2311(14) -0.1768(10) 0.4243(14) 0.021(4) Uiso 1 1 d . . . . .
H3 H 0.2972(16) -0.1751(11) 0.3120(14) 0.028(4) Uiso 1 1 d . . . . .
H4 H -0.0979(14) -0.2283(10) 0.2564(14) 0.020(3) Uiso 1 1 d . . . . .
H5 H -0.0067(16) -0.2111(11) 0.3896(15) 0.029(4) Uiso 1 1 d . . . . .
H6 H 0.0407(15) 0.0160(10) 0.3543(14) 0.023(4) Uiso 1 1 d . . . . .
H7 H 0.0815(14) -0.0613(10) 0.4489(14) 0.021(4) Uiso 1 1 d . . . . .
H8 H 0.2384(15) -0.0528(10) 0.1512(15) 0.026(4) Uiso 1 1 d . . . . .
H9 H 0.1398(15) 0.0194(10) 0.1702(14) 0.023(4) Uiso 1 1 d . . . . .
H10 H 0.0237(17) -0.0823(11) 0.0207(16) 0.034(5) Uiso 1 1 d . . . . .
H11 H 0.1523(16) -0.2043(10) 0.0953(15) 0.027(4) Uiso 1 1 d . . . . .
H12 H 0.0020(16) -0.2271(11) 0.0790(15) 0.029(4) Uiso 1 1 d . . . . .
H13 H -0.1554(15) -0.1067(10) 0.1055(14) 0.023(4) Uiso 1 1 d . . . . .
H14 H -0.1045(14) -0.0106(10) 0.1388(14) 0.023(4) Uiso 1 1 d . . . . .
H15 H 0.1545(18) -0.3297(12) 0.3683(17) 0.040(5) Uiso 1 1 d . . . . .
H16 H 0.0573(17) -0.3497(11) 0.2329(16) 0.035(4) Uiso 1 1 d . . . . .
H17 H 0.2115(17) -0.3264(12) 0.2449(16) 0.037(5) Uiso 1 1 d . . . . .
H18 H -0.1977(18) -0.0140(13) 0.3298(18) 0.045(5) Uiso 1 1 d . . . . .
H19 H -0.2546(17) -0.1101(11) 0.2883(16) 0.033(4) Uiso 1 1 d . . . . .
H20 H -0.1621(18) -0.0975(12) 0.4170(18) 0.037(5) Uiso 1 1 d . . . . .
H21 H 0.2774(14) 0.1944(10) 0.1836(14) 0.021(4) Uiso 1 1 d . . . . .
H22 H 0.3728(15) 0.2204(10) 0.0239(15) 0.026(4) Uiso 1 1 d . . . . .
H23 H 0.6291(16) 0.0217(10) 0.1350(15) 0.028(4) Uiso 1 1 d . . . . .
H24 H 0.5396(15) 0.0012(11) 0.3053(15) 0.028(4) Uiso 1 1 d . . . . .
H25 H 0.5808(17) 0.1964(12) -0.1694(17) 0.039(5) Uiso 1 1 d . . . . .
H26 H 0.4349(18) 0.1905(11) -0.1522(16) 0.034(4) Uiso 1 1 d . . . . .
H27 H 0.5393(17) 0.2576(12) -0.0740(16) 0.037(5) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 O1 1.4379(8) . ?
S1 O2 1.4495(8) . ?
S1 N1 1.6090(9) . ?
S1 C13 1.7664(11) . ?
O3 C16 1.3594(13) . ?
O3 C19 1.4278(15) . ?
N1 C1 1.4887(12) . ?
N1 H1 0.895(18) . ?
C1 C6 1.5352(14) . ?
C1 C2 1.5354(14) . ?
C1 C7 1.5381(14) . ?
C2 C3 1.5397(14) . ?
C2 H2 0.999(15) . ?
C2 H3 0.979(16) . ?
C3 C11 1.5261(15) . ?
C3 C9 1.5341(16) . ?
C3 C4 1.5361(15) . ?
C4 C5 1.5351(15) . ?
C4 H4 0.986(15) . ?
C4 H5 0.977(16) . ?
C5 C12 1.5252(15) . ?
C5 C10 1.5372(15) . ?
C5 C6 1.5410(14) . ?
C6 H6 0.975(16) . ?
C6 H7 0.983(16) . ?
C7 C8 1.5378(15) . ?
C7 H8 0.997(16) . ?
C7 H9 0.973(16) . ?
C8 C9 1.5316(16) . ?
C8 C10 1.5337(16) . ?
C8 H10 0.985(17) . ?
C9 H11 0.995(16) . ?
C9 H12 0.975(16) . ?
C10 H13 0.969(15) . ?
C10 H14 1.019(15) . ?
C11 H15 1.012(19) . ?
C11 H16 1.012(17) . ?
C11 H17 1.018(18) . ?
C12 H18 1.02(2) . ?
C12 H19 0.984(18) . ?
C12 H20 0.956(19) . ?
C13 C14 1.3872(14) . ?
C13 C18 1.4003(14) . ?
C14 C15 1.3943(15) . ?
C14 H21 0.959(15) . ?
C15 C16 1.3928(15) . ?
C15 H22 0.919(16) . ?
C16 C17 1.4014(16) . ?
C17 C18 1.3793(16) . ?
C17 H23 0.979(17) . ?
C18 H24 0.950(16) . ?
C19 H25 0.968(18) . ?
C19 H26 0.949(17) . ?
C19 H27 0.994(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 118.33(5) . . ?
O1 S1 N1 109.94(5) . . ?
O2 S1 N1 105.14(5) . . ?
O1 S1 C13 107.18(5) . . ?
O2 S1 C13 106.73(5) . . ?
N1 S1 C13 109.29(5) . . ?
C16 O3 C19 116.87(9) . . ?
C1 N1 S1 126.33(7) . . ?
C1 N1 H1 119.8(11) . . ?
S1 N1 H1 109.5(11) . . ?
N1 C1 C6 109.81(8) . . ?
N1 C1 C2 106.06(8) . . ?
C6 C1 C2 108.45(8) . . ?
N1 C1 C7 113.13(8) . . ?
C6 C1 C7 109.82(8) . . ?
C2 C1 C7 109.41(8) . . ?
C1 C2 C3 110.64(8) . . ?
C1 C2 H2 109.3(9) . . ?
C3 C2 H2 108.2(9) . . ?
C1 C2 H3 109.8(10) . . ?
C3 C2 H3 110.3(10) . . ?
H2 C2 H3 108.5(13) . . ?
C11 C3 C9 110.43(9) . . ?
C11 C3 C4 110.54(9) . . ?
C9 C3 C4 107.88(9) . . ?
C11 C3 C2 110.33(9) . . ?
C9 C3 C2 109.00(9) . . ?
C4 C3 C2 108.61(8) . . ?
C5 C4 C3 111.60(8) . . ?
C5 C4 H4 108.4(9) . . ?
C3 C4 H4 110.3(9) . . ?
C5 C4 H5 109.8(10) . . ?
C3 C4 H5 108.8(9) . . ?
H4 C4 H5 107.9(13) . . ?
C12 C5 C4 110.24(9) . . ?
C12 C5 C10 111.25(9) . . ?
C4 C5 C10 108.71(9) . . ?
C12 C5 C6 109.54(9) . . ?
C4 C5 C6 108.58(8) . . ?
C10 C5 C6 108.47(8) . . ?
C1 C6 C5 110.72(8) . . ?
C1 C6 H6 111.0(9) . . ?
C5 C6 H6 109.1(9) . . ?
C1 C6 H7 108.0(9) . . ?
C5 C6 H7 109.8(9) . . ?
H6 C6 H7 108.3(13) . . ?
C8 C7 C1 109.12(8) . . ?
C8 C7 H8 110.3(9) . . ?
C1 C7 H8 111.7(9) . . ?
C8 C7 H9 109.5(9) . . ?
C1 C7 H9 109.7(9) . . ?
H8 C7 H9 106.4(13) . . ?
C9 C8 C10 109.75(9) . . ?
C9 C8 C7 109.30(9) . . ?
C10 C8 C7 109.69(9) . . ?
C9 C8 H10 108.1(10) . . ?
C10 C8 H10 109.2(10) . . ?
C7 C8 H10 110.9(10) . . ?
C8 C9 C3 110.58(9) . . ?
C8 C9 H11 108.4(9) . . ?
C3 C9 H11 110.6(9) . . ?
C8 C9 H12 110.9(10) . . ?
C3 C9 H12 109.1(10) . . ?
H11 C9 H12 107.2(14) . . ?
C8 C10 C5 110.06(8) . . ?
C8 C10 H13 110.3(9) . . ?
C5 C10 H13 109.0(9) . . ?
C8 C10 H14 110.6(9) . . ?
C5 C10 H14 110.6(9) . . ?
H13 C10 H14 106.1(12) . . ?
C3 C11 H15 111.3(11) . . ?
C3 C11 H16 111.1(10) . . ?
H15 C11 H16 108.0(15) . . ?
C3 C11 H17 109.0(10) . . ?
H15 C11 H17 110.1(15) . . ?
H16 C11 H17 107.3(14) . . ?
C5 C12 H18 111.8(11) . . ?
C5 C12 H19 111.8(10) . . ?
H18 C12 H19 108.5(14) . . ?
C5 C12 H20 110.2(11) . . ?
H18 C12 H20 109.3(15) . . ?
H19 C12 H20 105.1(15) . . ?
C14 C13 C18 120.47(10) . . ?
C14 C13 S1 119.96(8) . . ?
C18 C13 S1 119.51(8) . . ?
C13 C14 C15 120.33(10) . . ?
C13 C14 H21 118.8(9) . . ?
C15 C14 H21 120.8(9) . . ?
C16 C15 C14 119.21(10) . . ?
C16 C15 H22 122.1(10) . . ?
C14 C15 H22 118.7(10) . . ?
O3 C16 C15 124.68(10) . . ?
O3 C16 C17 115.08(10) . . ?
C15 C16 C17 120.23(10) . . ?
C18 C17 C16 120.44(10) . . ?
C18 C17 H23 121.5(10) . . ?
C16 C17 H23 118.0(10) . . ?
C17 C18 C13 119.30(10) . . ?
C17 C18 H24 121.2(10) . . ?
C13 C18 H24 119.5(10) . . ?
O3 C19 H25 105.1(11) . . ?
O3 C19 H26 110.0(11) . . ?
H25 C19 H26 113.4(15) . . ?
O3 C19 H27 109.8(10) . . ?
H25 C19 H27 107.6(14) . . ?
H26 C19 H27 110.8(14) . . ?

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
O1 S1 N1 C1 42.31(10) . . . . ?
O2 S1 N1 C1 170.71(8) . . . . ?
C13 S1 N1 C1 -75.06(9) . . . . ?
S1 N1 C1 C6 -80.18(10) . . . . ?
S1 N1 C1 C2 162.84(8) . . . . ?
S1 N1 C1 C7 42.90(12) . . . . ?
N1 C1 C2 C3 178.28(8) . . . . ?
C6 C1 C2 C3 60.38(11) . . . . ?
C7 C1 C2 C3 -59.40(11) . . . . ?
C1 C2 C3 C11 179.51(9) . . . . ?
C1 C2 C3 C9 58.09(11) . . . . ?
C1 C2 C3 C4 -59.19(11) . . . . ?
C11 C3 C4 C5 179.57(9) . . . . ?
C9 C3 C4 C5 -59.60(11) . . . . ?
C2 C3 C4 C5 58.40(11) . . . . ?
C3 C4 C5 C12 -178.29(9) . . . . ?
C3 C4 C5 C10 59.53(11) . . . . ?
C3 C4 C5 C6 -58.29(11) . . . . ?
N1 C1 C6 C5 -175.80(8) . . . . ?
C2 C1 C6 C5 -60.33(11) . . . . ?
C7 C1 C6 C5 59.19(11) . . . . ?
C12 C5 C6 C1 179.50(9) . . . . ?
C4 C5 C6 C1 59.06(11) . . . . ?
C10 C5 C6 C1 -58.90(11) . . . . ?
N1 C1 C7 C8 178.07(8) . . . . ?
C6 C1 C7 C8 -58.85(11) . . . . ?
C2 C1 C7 C8 60.07(11) . . . . ?
C1 C7 C8 C9 -60.50(11) . . . . ?
C1 C7 C8 C10 59.87(11) . . . . ?
C10 C8 C9 C3 -60.01(11) . . . . ?
C7 C8 C9 C3 60.32(12) . . . . ?
C11 C3 C9 C8 -179.91(9) . . . . ?
C4 C3 C9 C8 59.19(11) . . . . ?
C2 C3 C9 C8 -58.56(11) . . . . ?
C9 C8 C10 C5 59.12(11) . . . . ?
C7 C8 C10 C5 -60.98(11) . . . . ?
C12 C5 C10 C8 -179.84(9) . . . . ?
C4 C5 C10 C8 -58.27(11) . . . . ?
C6 C5 C10 C8 59.61(11) . . . . ?
O1 S1 C13 C14 10.52(10) . . . . ?
O2 S1 C13 C14 -117.18(9) . . . . ?
N1 S1 C13 C14 129.61(9) . . . . ?
O1 S1 C13 C18 -172.04(8) . . . . ?
O2 S1 C13 C18 60.26(10) . . . . ?
N1 S1 C13 C18 -52.95(10) . . . . ?
C18 C13 C14 C15 -1.34(16) . . . . ?
S1 C13 C14 C15 176.08(8) . . . . ?
C13 C14 C15 C16 1.51(17) . . . . ?
C19 O3 C16 C15 -0.93(17) . . . . ?
C19 O3 C16 C17 179.44(11) . . . . ?
C14 C15 C16 O3 -179.97(10) . . . . ?
C14 C15 C16 C17 -0.35(17) . . . . ?
O3 C16 C17 C18 178.65(10) . . . . ?
C15 C16 C17 C18 -1.00(17) . . . . ?
C16 C17 C18 C13 1.18(17) . . . . ?
C14 C13 C18 C17 -0.02(16) . . . . ?
S1 C13 C18 C17 -177.45(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.895(18) 2.046(18) 2.9329(12) 170.7(16) 3_656
C6 H6 O1 0.975(16) 2.603(15) 3.2253(13) 121.8(11) .
C19 H27 O2 0.994(19) 2.631(19) 3.5267(16) 150.1(13) 4_565

####################################################################### 
# 
# 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_22
_database_code_depnum_ccdc_archive 'CCDC 1962776'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2019-10-31 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;

_audit_creation_date             2017-04-03T15:00:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C18 H24 N2 O4 S'
_chemical_formula_sum            'C18 H24 N2 O4 S'
_chemical_formula_weight         364.45

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.9094(6)
_cell_length_b                   12.1019(5)
_cell_length_c                   10.5363(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.7580(10)
_cell_angle_gamma                90
_cell_volume                     1810.51(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7821
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      31.21

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             776

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

_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.553
_exptl_absorpt_correction_T_max  0.6481

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

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_number            21690
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.211
_diffrn_reflns_theta_max         31.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.951
_reflns_Friedel_coverage         0
_reflns_number_total             5733
_reflns_number_gt                4799
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   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)+(0.0600P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5733
_refine_ls_number_parameters     322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1052
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      1.04
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.35
_refine_diff_density_rms         0.062

#----------------------------------------------------------------------------#
#                   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 0.09246(2) 0.40307(2) 0.39070(2) 0.01357(7) Uani 1 1 d . . . . .
O1 O 0.14674(6) 0.30324(6) 0.41061(8) 0.02036(17) Uani 1 1 d . . . . .
O2 O -0.00707(6) 0.39559(7) 0.37350(8) 0.01939(17) Uani 1 1 d . . . . .
O3 O 0.11798(7) 0.72779(7) 0.34771(9) 0.0273(2) Uani 1 1 d . . . . .
O4 O -0.01430(6) 0.64042(8) 0.31608(9) 0.02602(19) Uani 1 1 d . . . . .
N1 N 0.13577(6) 0.49136(7) 0.50674(9) 0.01427(17) Uani 1 1 d . . . . .
N2 N 0.06264(7) 0.65330(7) 0.29907(9) 0.01679(18) Uani 1 1 d . . . . .
C1 C 0.23470(7) 0.49526(8) 0.59606(10) 0.01387(18) Uani 1 1 d . . . . .
C2 C 0.25287(8) 0.40387(10) 0.70180(12) 0.0195(2) Uani 1 1 d . . . . .
C3 C 0.35243(8) 0.41475(10) 0.80118(12) 0.0232(2) Uani 1 1 d . . . . .
C4 C 0.36141(8) 0.52937(11) 0.86692(11) 0.0237(2) Uani 1 1 d . . . . .
C5 C 0.34479(8) 0.62248(10) 0.76301(11) 0.0205(2) Uani 1 1 d . . . . .
C6 C 0.24559(8) 0.60860(9) 0.66423(11) 0.0182(2) Uani 1 1 d . . . . .
C7 C 0.30636(8) 0.48664(10) 0.51851(11) 0.0199(2) Uani 1 1 d . . . . .
C8 C 0.40621(8) 0.49781(11) 0.61784(12) 0.0233(2) Uani 1 1 d . . . . .
C9 C 0.42353(9) 0.40630(11) 0.72271(14) 0.0267(3) Uani 1 1 d . . . . .
C10 C 0.41695(8) 0.61049(10) 0.68673(13) 0.0232(2) Uani 1 1 d . . . . .
C11 C 0.36867(11) 0.32355(15) 0.90605(18) 0.0421(4) Uani 1 1 d . . . . .
C12 C 0.35307(10) 0.73572(13) 0.82948(16) 0.0348(3) Uani 1 1 d . . . . .
C13 C 0.10494(7) 0.46336(8) 0.24308(10) 0.01350(18) Uani 1 1 d . . . . .
C14 C 0.09038(7) 0.57518(8) 0.21076(10) 0.01375(18) Uani 1 1 d . . . . .
C15 C 0.09944(8) 0.61889(9) 0.09366(11) 0.0170(2) Uani 1 1 d . . . . .
C16 C 0.12217(8) 0.54802(9) 0.00401(11) 0.0195(2) Uani 1 1 d . . . . .
C17 C 0.13696(9) 0.43625(9) 0.03367(11) 0.0202(2) Uani 1 1 d . . . . .
C18 C 0.12928(8) 0.39420(9) 0.15294(11) 0.0174(2) Uani 1 1 d . . . . .
H1 H 0.0946(12) 0.5153(13) 0.5383(16) 0.028(4) Uiso 1 1 d . . . . .
H2 H 0.2460(12) 0.3283(15) 0.6548(18) 0.037(5) Uiso 1 1 d . . . . .
H3 H 0.2057(12) 0.4080(13) 0.7455(17) 0.031(4) Uiso 1 1 d . . . . .
H4 H 0.4259(12) 0.5388(14) 0.9314(17) 0.030(4) Uiso 1 1 d . . . . .
H5 H 0.3122(12) 0.5347(15) 0.9134(17) 0.034(4) Uiso 1 1 d . . . . .
H6 H 0.1976(11) 0.6148(13) 0.7107(16) 0.026(4) Uiso 1 1 d . . . . .
H7 H 0.2333(10) 0.6654(14) 0.5963(16) 0.026(4) Uiso 1 1 d . . . . .
H8 H 0.2940(11) 0.5421(13) 0.4478(15) 0.024(4) Uiso 1 1 d . . . . .
H9 H 0.3011(12) 0.4176(14) 0.4729(18) 0.031(4) Uiso 1 1 d . . . . .
H10 H 0.4534(12) 0.4917(14) 0.5691(17) 0.032(4) Uiso 1 1 d . . . . .
H11 H 0.4881(13) 0.4143(14) 0.7871(18) 0.035(5) Uiso 1 1 d . . . . .
H12 H 0.4187(12) 0.3329(15) 0.6776(17) 0.034(4) Uiso 1 1 d . . . . .
H13 H 0.4097(11) 0.6712(15) 0.6206(17) 0.033(4) Uiso 1 1 d . . . . .
H14 H 0.4792(12) 0.6202(15) 0.7470(18) 0.034(4) Uiso 1 1 d . . . . .
H15 H 0.3209(14) 0.3263(18) 0.951(2) 0.051(6) Uiso 1 1 d . . . . .
H16 H 0.3637(16) 0.2483(19) 0.864(2) 0.062(6) Uiso 1 1 d . . . . .
H17 H 0.4307(13) 0.3296(16) 0.9701(19) 0.045(5) Uiso 1 1 d . . . . .
H18 H 0.3057(14) 0.7437(17) 0.877(2) 0.050(5) Uiso 1 1 d . . . . .
H19 H 0.4166(13) 0.7476(15) 0.891(2) 0.044(5) Uiso 1 1 d . . . . .
H20 H 0.3396(15) 0.7956(18) 0.760(2) 0.056(6) Uiso 1 1 d . . . . .
H21 H 0.0884(11) 0.6936(13) 0.0770(16) 0.026(4) Uiso 1 1 d . . . . .
H22 H 0.1253(12) 0.5754(13) -0.0766(17) 0.029(4) Uiso 1 1 d . . . . .
H23 H 0.1498(11) 0.3878(14) -0.0276(17) 0.029(4) Uiso 1 1 d . . . . .
H24 H 0.1372(10) 0.3197(13) 0.1728(14) 0.020(3) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 O1 1.4335(8) . ?
S1 O2 1.4419(8) . ?
S1 N1 1.6037(9) . ?
S1 C13 1.7784(10) . ?
O3 N2 1.2239(13) . ?
O4 N2 1.2239(13) . ?
N1 C1 1.4888(13) . ?
N1 H1 0.834(17) . ?
N2 C14 1.4715(13) . ?
C1 C7 1.5337(15) . ?
C1 C6 1.5337(15) . ?
C1 C2 1.5342(15) . ?
C2 C3 1.5392(16) . ?
C2 H2 1.030(19) . ?
C2 H3 0.951(18) . ?
C3 C11 1.5279(18) . ?
C3 C9 1.5337(18) . ?
C3 C4 1.5379(19) . ?
C4 C5 1.5376(17) . ?
C4 H4 1.000(17) . ?
C4 H5 1.000(18) . ?
C5 C12 1.5267(18) . ?
C5 C10 1.5335(17) . ?
C5 C6 1.5363(15) . ?
C6 H6 0.985(16) . ?
C6 H7 0.969(16) . ?
C7 C8 1.5425(16) . ?
C7 H8 0.978(16) . ?
C7 H9 0.955(17) . ?
C8 C9 1.5298(19) . ?
C8 C10 1.5301(18) . ?
C8 H10 0.992(18) . ?
C9 H11 0.999(18) . ?
C9 H12 1.000(18) . ?
C10 H13 0.996(18) . ?
C10 H14 0.958(18) . ?
C11 H15 0.97(2) . ?
C11 H16 1.01(2) . ?
C11 H17 0.967(19) . ?
C12 H18 0.98(2) . ?
C12 H19 0.98(2) . ?
C12 H20 1.01(2) . ?
C13 C18 1.3945(14) . ?
C13 C14 1.3962(14) . ?
C14 C15 1.3864(14) . ?
C15 C16 1.3920(15) . ?
C15 H21 0.927(16) . ?
C16 C17 1.3906(16) . ?
C16 H22 0.926(17) . ?
C17 C18 1.3925(15) . ?
C17 H23 0.934(17) . ?
C18 H24 0.925(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 118.62(5) . . ?
O1 S1 N1 111.83(5) . . ?
O2 S1 N1 107.30(5) . . ?
O1 S1 C13 105.59(5) . . ?
O2 S1 C13 107.10(5) . . ?
N1 S1 C13 105.56(5) . . ?
C1 N1 S1 126.44(7) . . ?
C1 N1 H1 116.4(11) . . ?
S1 N1 H1 111.2(11) . . ?
O4 N2 O3 125.08(10) . . ?
O4 N2 C14 117.87(9) . . ?
O3 N2 C14 117.03(9) . . ?
N1 C1 C7 112.20(8) . . ?
N1 C1 C6 105.51(8) . . ?
C7 C1 C6 108.60(9) . . ?
N1 C1 C2 110.95(8) . . ?
C7 C1 C2 109.90(9) . . ?
C6 C1 C2 109.55(9) . . ?
C1 C2 C3 110.63(9) . . ?
C1 C2 H2 108.7(10) . . ?
C3 C2 H2 109.7(10) . . ?
C1 C2 H3 108.7(10) . . ?
C3 C2 H3 111.6(10) . . ?
H2 C2 H3 107.4(14) . . ?
C11 C3 C9 111.01(12) . . ?
C11 C3 C4 110.67(12) . . ?
C9 C3 C4 108.86(10) . . ?
C11 C3 C2 109.72(10) . . ?
C9 C3 C2 108.02(10) . . ?
C4 C3 C2 108.48(10) . . ?
C5 C4 C3 111.55(9) . . ?
C5 C4 H4 108.2(10) . . ?
C3 C4 H4 110.0(10) . . ?
C5 C4 H5 108.6(10) . . ?
C3 C4 H5 107.6(10) . . ?
H4 C4 H5 110.9(14) . . ?
C12 C5 C10 110.73(11) . . ?
C12 C5 C6 109.60(10) . . ?
C10 C5 C6 108.60(10) . . ?
C12 C5 C4 110.99(11) . . ?
C10 C5 C4 108.50(10) . . ?
C6 C5 C4 108.36(9) . . ?
C1 C6 C5 110.95(9) . . ?
C1 C6 H6 108.2(9) . . ?
C5 C6 H6 110.5(10) . . ?
C1 C6 H7 108.6(10) . . ?
C5 C6 H7 110.4(9) . . ?
H6 C6 H7 108.1(13) . . ?
C1 C7 C8 108.52(9) . . ?
C1 C7 H8 111.0(9) . . ?
C8 C7 H8 112.1(9) . . ?
C1 C7 H9 111.4(10) . . ?
C8 C7 H9 109.4(10) . . ?
H8 C7 H9 104.4(14) . . ?
C9 C8 C10 109.41(10) . . ?
C9 C8 C7 110.00(10) . . ?
C10 C8 C7 109.86(10) . . ?
C9 C8 H10 109.2(10) . . ?
C10 C8 H10 108.9(10) . . ?
C7 C8 H10 109.4(10) . . ?
C8 C9 C3 110.42(10) . . ?
C8 C9 H11 109.6(10) . . ?
C3 C9 H11 108.0(10) . . ?
C8 C9 H12 109.1(10) . . ?
C3 C9 H12 110.7(10) . . ?
H11 C9 H12 108.9(14) . . ?
C8 C10 C5 110.14(9) . . ?
C8 C10 H13 110.6(10) . . ?
C5 C10 H13 110.7(9) . . ?
C8 C10 H14 111.3(10) . . ?
C5 C10 H14 109.5(10) . . ?
H13 C10 H14 104.4(14) . . ?
C3 C11 H15 110.5(13) . . ?
C3 C11 H16 111.2(13) . . ?
H15 C11 H16 106.3(18) . . ?
C3 C11 H17 110.9(12) . . ?
H15 C11 H17 110.3(17) . . ?
H16 C11 H17 107.6(17) . . ?
C5 C12 H18 110.5(12) . . ?
C5 C12 H19 111.3(11) . . ?
H18 C12 H19 110.1(16) . . ?
C5 C12 H20 110.0(12) . . ?
H18 C12 H20 106.4(17) . . ?
H19 C12 H20 108.5(16) . . ?
C18 C13 C14 117.97(9) . . ?
C18 C13 S1 117.89(8) . . ?
C14 C13 S1 124.13(8) . . ?
C15 C14 C13 122.46(9) . . ?
C15 C14 N2 116.11(9) . . ?
C13 C14 N2 121.42(9) . . ?
C14 C15 C16 118.61(10) . . ?
C14 C15 H21 118.8(10) . . ?
C16 C15 H21 122.6(10) . . ?
C17 C16 C15 120.10(10) . . ?
C17 C16 H22 120.4(10) . . ?
C15 C16 H22 119.5(10) . . ?
C16 C17 C18 120.48(10) . . ?
C16 C17 H23 120.5(10) . . ?
C18 C17 H23 119.0(10) . . ?
C17 C18 C13 120.36(10) . . ?
C17 C18 H24 121.4(9) . . ?
C13 C18 H24 118.2(9) . . ?

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
O1 S1 N1 C1 21.91(10) . . . . ?
O2 S1 N1 C1 153.61(8) . . . . ?
C13 S1 N1 C1 -92.42(9) . . . . ?
S1 N1 C1 C7 48.66(12) . . . . ?
S1 N1 C1 C6 166.74(8) . . . . ?
S1 N1 C1 C2 -74.70(11) . . . . ?
N1 C1 C2 C3 -175.00(9) . . . . ?
C7 C1 C2 C3 60.33(12) . . . . ?
C6 C1 C2 C3 -58.91(12) . . . . ?
C1 C2 C3 C11 179.56(12) . . . . ?
C1 C2 C3 C9 -59.30(12) . . . . ?
C1 C2 C3 C4 58.55(13) . . . . ?
C11 C3 C4 C5 -179.70(10) . . . . ?
C9 C3 C4 C5 58.03(12) . . . . ?
C2 C3 C4 C5 -59.27(12) . . . . ?
C3 C4 C5 C12 179.51(10) . . . . ?
C3 C4 C5 C10 -58.62(12) . . . . ?
C3 C4 C5 C6 59.12(12) . . . . ?
N1 C1 C6 C5 178.51(9) . . . . ?
C7 C1 C6 C5 -61.02(12) . . . . ?
C2 C1 C6 C5 59.02(12) . . . . ?
C12 C5 C6 C1 -179.72(11) . . . . ?
C10 C5 C6 C1 59.20(12) . . . . ?
C4 C5 C6 C1 -58.47(12) . . . . ?
N1 C1 C7 C8 176.93(9) . . . . ?
C6 C1 C7 C8 60.70(11) . . . . ?
C2 C1 C7 C8 -59.12(12) . . . . ?
C1 C7 C8 C9 59.48(12) . . . . ?
C1 C7 C8 C10 -61.02(12) . . . . ?
C10 C8 C9 C3 60.03(13) . . . . ?
C7 C8 C9 C3 -60.74(13) . . . . ?
C11 C3 C9 C8 179.80(11) . . . . ?
C4 C3 C9 C8 -58.13(13) . . . . ?
C2 C3 C9 C8 59.47(13) . . . . ?
C9 C8 C10 C5 -60.68(12) . . . . ?
C7 C8 C10 C5 60.17(13) . . . . ?
C12 C5 C10 C8 -178.60(10) . . . . ?
C6 C5 C10 C8 -58.23(12) . . . . ?
C4 C5 C10 C8 59.36(12) . . . . ?
O1 S1 C13 C18 22.86(10) . . . . ?
O2 S1 C13 C18 -104.45(9) . . . . ?
N1 S1 C13 C18 141.44(9) . . . . ?
O1 S1 C13 C14 -158.26(9) . . . . ?
O2 S1 C13 C14 74.43(10) . . . . ?
N1 S1 C13 C14 -39.68(10) . . . . ?
C18 C13 C14 C15 -0.14(16) . . . . ?
S1 C13 C14 C15 -179.02(8) . . . . ?
C18 C13 C14 N2 178.74(10) . . . . ?
S1 C13 C14 N2 -0.14(14) . . . . ?
O4 N2 C14 C15 114.04(11) . . . . ?
O3 N2 C14 C15 -64.48(13) . . . . ?
O4 N2 C14 C13 -64.91(13) . . . . ?
O3 N2 C14 C13 116.57(11) . . . . ?
C13 C14 C15 C16 1.25(16) . . . . ?
N2 C14 C15 C16 -177.68(10) . . . . ?
C14 C15 C16 C17 -1.15(17) . . . . ?
C15 C16 C17 C18 -0.04(18) . . . . ?
C16 C17 C18 C13 1.19(18) . . . . ?
C14 C13 C18 C17 -1.09(16) . . . . ?
S1 C13 C18 C17 177.87(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.834(17) 2.114(18) 2.9364(12) 168.7(16) 3_566
C2 H2 O1 1.030(19) 2.564(18) 3.2309(15) 122.0(12) .
C7 H9 O1 0.955(17) 2.593(17) 3.1987(14) 121.6(13) .

####################################################################### 
# 
# 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_21
_database_code_depnum_ccdc_archive 'CCDC 1962775'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2019-10-31 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;

_audit_creation_date             2017-04-04T20:54:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C19 H24 F3 N O2 S'
_chemical_formula_sum            'C19 H24 F3 N O2 S'
_chemical_formula_weight         387.45

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.4774(4)
_cell_length_b                   12.9160(6)
_cell_length_c                   15.3582(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.8470(10)
_cell_angle_gamma                90
_cell_volume                     1852.30(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9717
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      31.25

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             816

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

_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.6661
_exptl_absorpt_correction_T_max  0.7462

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

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_number            26169
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.073
_diffrn_reflns_theta_max         31.505
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.96
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.96
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.96
_reflns_Friedel_coverage         0
_reflns_number_total             5917
_reflns_number_gt                5004
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   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)+(0.0800P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5917
_refine_ls_number_parameters     331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.1157
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.34
_refine_diff_density_rms         0.059

#----------------------------------------------------------------------------#
#                   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'
F F 0.0171 0.0103 '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 0.48540(2) 0.34157(2) 0.05791(2) 0.01505(8) Uani 1 1 d . . . . .
O1 O 0.60086(8) 0.39383(6) 0.02534(5) 0.02070(16) Uani 1 1 d . . . . .
O2 O 0.51816(8) 0.26201(6) 0.12343(5) 0.01965(16) Uani 1 1 d . . . . .
F1 F 0.18541(11) -0.01688(6) -0.18743(5) 0.0433(2) Uani 1 1 d . . . . .
F2 F 0.33646(9) -0.03530(6) -0.06669(6) 0.0398(2) Uani 1 1 d . . . . .
F3 F 0.11880(9) 0.00556(6) -0.06271(6) 0.0379(2) Uani 1 1 d . . . . .
N1 N 0.39550(9) 0.43212(7) 0.09507(6) 0.01690(17) Uani 1 1 d . . . . .
C1 C 0.27468(10) 0.41942(7) 0.14492(6) 0.01498(18) Uani 1 1 d . . . . .
C2 C 0.32973(11) 0.38120(9) 0.23905(6) 0.0187(2) Uani 1 1 d . . . . .
C3 C 0.20800(12) 0.37700(9) 0.29313(7) 0.0204(2) Uani 1 1 d . . . . .
C4 C 0.09046(11) 0.30514(9) 0.24592(7) 0.0197(2) Uani 1 1 d . . . . .
C5 C 0.03168(11) 0.34228(8) 0.15161(7) 0.01706(19) Uani 1 1 d . . . . .
C6 C 0.15685(11) 0.34658(8) 0.09960(6) 0.01578(18) Uani 1 1 d . . . . .
C7 C 0.21173(12) 0.52830(8) 0.14954(8) 0.0214(2) Uani 1 1 d . . . . .
C8 C 0.08848(13) 0.52528(9) 0.20284(8) 0.0243(2) Uani 1 1 d . . . . .
C9 C 0.14508(13) 0.48608(10) 0.29676(8) 0.0261(2) Uani 1 1 d . . . . .
C10 C -0.02859(12) 0.45236(9) 0.15700(8) 0.0228(2) Uani 1 1 d . . . . .
C11 C 0.26568(15) 0.33587(12) 0.38584(8) 0.0316(3) Uani 1 1 d . . . . .
C12 C -0.08303(12) 0.26880(10) 0.10603(8) 0.0256(2) Uani 1 1 d . . . . .
C13 C 0.37836(10) 0.28399(8) -0.03548(6) 0.01495(18) Uani 1 1 d . . . . .
C14 C 0.34941(11) 0.17870(8) -0.03447(6) 0.01600(18) Uani 1 1 d . . . . .
C15 C 0.26442(10) 0.13480(8) -0.10834(7) 0.01665(19) Uani 1 1 d . . . . .
C16 C 0.20947(11) 0.19495(8) -0.18132(7) 0.01828(19) Uani 1 1 d . . . . .
C17 C 0.23971(11) 0.30049(8) -0.18123(7) 0.0189(2) Uani 1 1 d . . . . .
C18 C 0.32411(11) 0.34576(8) -0.10844(7) 0.01761(19) Uani 1 1 d . . . . .
C19 C 0.22727(13) 0.02252(8) -0.10638(8) 0.0230(2) Uani 1 1 d . . . . .
H1 H 0.3914(16) 0.4885(12) 0.0628(10) 0.024(3) Uiso 1 1 d . . . . .
H2 H 0.4040(16) 0.4275(12) 0.2657(10) 0.029(4) Uiso 1 1 d . . . . .
H3 H 0.3729(15) 0.3118(11) 0.2365(9) 0.021(3) Uiso 1 1 d . . . . .
H4 H 0.0100(16) 0.3026(12) 0.2772(9) 0.025(3) Uiso 1 1 d . . . . .
H5 H 0.1325(17) 0.2323(12) 0.2417(11) 0.030(4) Uiso 1 1 d . . . . .
H6 H 0.1959(15) 0.2778(12) 0.0939(9) 0.022(3) Uiso 1 1 d . . . . .
H7 H 0.1247(14) 0.3696(11) 0.0403(9) 0.019(3) Uiso 1 1 d . . . . .
H8 H 0.1721(17) 0.5565(13) 0.0877(11) 0.036(4) Uiso 1 1 d . . . . .
H9 H 0.2883(17) 0.5773(12) 0.1791(10) 0.031(4) Uiso 1 1 d . . . . .
H10 H 0.0464(18) 0.5955(14) 0.2032(11) 0.038(4) Uiso 1 1 d . . . . .
H11 H 0.2128(18) 0.5379(13) 0.3276(11) 0.038(4) Uiso 1 1 d . . . . .
H12 H 0.0658(15) 0.4845(11) 0.3300(10) 0.024(3) Uiso 1 1 d . . . . .
H13 H -0.0675(16) 0.4769(12) 0.0973(10) 0.031(4) Uiso 1 1 d . . . . .
H14 H -0.1109(18) 0.4480(13) 0.1909(11) 0.037(4) Uiso 1 1 d . . . . .
H15 H 0.1913(19) 0.3339(13) 0.4195(11) 0.039(5) Uiso 1 1 d . . . . .
H16 H 0.306(2) 0.2657(17) 0.3819(12) 0.053(5) Uiso 1 1 d . . . . .
H17 H 0.3336(18) 0.3824(14) 0.4147(11) 0.040(4) Uiso 1 1 d . . . . .
H18 H -0.1230(17) 0.2903(13) 0.0455(10) 0.031(4) Uiso 1 1 d . . . . .
H19 H -0.0441(19) 0.2035(15) 0.0985(11) 0.040(4) Uiso 1 1 d . . . . .
H20 H -0.1633(17) 0.2630(12) 0.1379(11) 0.035(4) Uiso 1 1 d . . . . .
H21 H 0.3854(15) 0.1391(11) 0.0157(10) 0.021(3) Uiso 1 1 d . . . . .
H22 H 0.1533(18) 0.1652(13) -0.2312(11) 0.037(5) Uiso 1 1 d . . . . .
H23 H 0.2055(17) 0.3415(11) -0.2305(10) 0.028(4) Uiso 1 1 d . . . . .
H24 H 0.3465(15) 0.4211(11) -0.1080(9) 0.020(3) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 O2 1.4346(8) . ?
S1 O1 1.4458(8) . ?
S1 N1 1.6080(9) . ?
S1 C13 1.7726(10) . ?
F1 C19 1.3406(14) . ?
F2 C19 1.3358(14) . ?
F3 C19 1.3380(14) . ?
N1 C1 1.4913(12) . ?
N1 H1 0.878(15) . ?
C1 C2 1.5323(14) . ?
C1 C6 1.5332(14) . ?
C1 C7 1.5340(14) . ?
C2 C3 1.5334(14) . ?
C2 H2 0.960(15) . ?
C2 H3 0.989(14) . ?
C3 C11 1.5304(16) . ?
C3 C4 1.5336(15) . ?
C3 C9 1.5347(16) . ?
C4 C5 1.5369(14) . ?
C4 H4 0.969(15) . ?
C4 H5 1.028(16) . ?
C5 C12 1.5206(15) . ?
C5 C10 1.5398(15) . ?
C5 C6 1.5403(14) . ?
C6 H6 0.972(15) . ?
C6 H7 0.958(14) . ?
C7 C8 1.5372(15) . ?
C7 H8 1.027(17) . ?
C7 H9 1.011(16) . ?
C8 C10 1.5318(17) . ?
C8 C9 1.5364(18) . ?
C8 H10 0.991(18) . ?
C9 H11 0.989(17) . ?
C9 H12 0.978(15) . ?
C10 H13 0.980(16) . ?
C10 H14 1.010(17) . ?
C11 H15 0.943(18) . ?
C11 H16 0.99(2) . ?
C11 H17 0.935(18) . ?
C12 H18 0.983(16) . ?
C12 H19 0.936(19) . ?
C12 H20 0.975(16) . ?
C13 C14 1.3879(14) . ?
C13 C18 1.3998(13) . ?
C14 C15 1.3945(14) . ?
C14 H21 0.939(14) . ?
C15 C16 1.3897(14) . ?
C15 C19 1.4939(15) . ?
C16 C17 1.3929(15) . ?
C16 H22 0.938(17) . ?
C17 C18 1.3877(14) . ?
C17 H23 0.935(15) . ?
C18 H24 0.996(14) . ?

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
O2 S1 O1 119.43(5) . . ?
O2 S1 N1 109.65(5) . . ?
O1 S1 N1 105.16(5) . . ?
O2 S1 C13 106.99(5) . . ?
O1 S1 C13 106.15(4) . . ?
N1 S1 C13 109.13(5) . . ?
C1 N1 S1 127.03(7) . . ?
C1 N1 H1 114.7(10) . . ?
S1 N1 H1 112.2(10) . . ?
N1 C1 C2 110.63(8) . . ?
N1 C1 C6 113.45(8) . . ?
C2 C1 C6 109.55(8) . . ?
N1 C1 C7 105.18(8) . . ?
C2 C1 C7 108.90(8) . . ?
C6 C1 C7 108.95(8) . . ?
C1 C2 C3 110.86(8) . . ?
C1 C2 H2 108.0(9) . . ?
C3 C2 H2 110.8(9) . . ?
C1 C2 H3 109.3(8) . . ?
C3 C2 H3 110.1(8) . . ?
H2 C2 H3 107.7(12) . . ?
C11 C3 C2 109.52(9) . . ?
C11 C3 C4 110.17(10) . . ?
C2 C3 C4 108.56(8) . . ?
C11 C3 C9 111.35(10) . . ?
C2 C3 C9 108.67(9) . . ?
C4 C3 C9 108.51(9) . . ?
C3 C4 C5 111.94(9) . . ?
C3 C4 H4 110.8(9) . . ?
C5 C4 H4 106.8(9) . . ?
C3 C4 H5 109.0(9) . . ?
C5 C4 H5 108.0(9) . . ?
H4 C4 H5 110.3(13) . . ?
C12 C5 C4 110.76(9) . . ?
C12 C5 C10 111.00(9) . . ?
C4 C5 C10 108.39(9) . . ?
C12 C5 C6 109.71(9) . . ?
C4 C5 C6 108.23(8) . . ?
C10 C5 C6 108.68(8) . . ?
C1 C6 C5 110.64(8) . . ?
C1 C6 H6 110.0(8) . . ?
C5 C6 H6 110.7(8) . . ?
C1 C6 H7 109.3(8) . . ?
C5 C6 H7 110.9(8) . . ?
H6 C6 H7 105.2(12) . . ?
C1 C7 C8 109.78(8) . . ?
C1 C7 H8 111.4(9) . . ?
C8 C7 H8 108.1(9) . . ?
C1 C7 H9 109.9(9) . . ?
C8 C7 H9 109.2(9) . . ?
H8 C7 H9 108.4(13) . . ?
C10 C8 C9 109.76(9) . . ?
C10 C8 C7 109.12(9) . . ?
C9 C8 C7 109.46(10) . . ?
C10 C8 H10 107.7(10) . . ?
C9 C8 H10 111.8(10) . . ?
C7 C8 H10 108.9(10) . . ?
C3 C9 C8 110.11(9) . . ?
C3 C9 H11 114.5(10) . . ?
C8 C9 H11 108.7(10) . . ?
C3 C9 H12 109.8(9) . . ?
C8 C9 H12 108.7(9) . . ?
H11 C9 H12 104.9(13) . . ?
C8 C10 C5 110.26(9) . . ?
C8 C10 H13 111.0(9) . . ?
C5 C10 H13 109.4(9) . . ?
C8 C10 H14 111.1(9) . . ?
C5 C10 H14 107.6(10) . . ?
H13 C10 H14 107.4(13) . . ?
C3 C11 H15 109.8(10) . . ?
C3 C11 H16 110.0(11) . . ?
H15 C11 H16 110.1(14) . . ?
C3 C11 H17 109.0(11) . . ?
H15 C11 H17 105.9(14) . . ?
H16 C11 H17 112.0(15) . . ?
C5 C12 H18 112.9(10) . . ?
C5 C12 H19 110.7(11) . . ?
H18 C12 H19 103.6(14) . . ?
C5 C12 H20 112.0(10) . . ?
H18 C12 H20 106.8(13) . . ?
H19 C12 H20 110.5(14) . . ?
C14 C13 C18 121.41(9) . . ?
C14 C13 S1 119.27(7) . . ?
C18 C13 S1 119.32(8) . . ?
C13 C14 C15 118.49(9) . . ?
C13 C14 H21 119.9(9) . . ?
C15 C14 H21 121.6(9) . . ?
C16 C15 C14 120.90(10) . . ?
C16 C15 C19 120.12(9) . . ?
C14 C15 C19 118.92(9) . . ?
C15 C16 C17 119.84(9) . . ?
C15 C16 H22 120.8(10) . . ?
C17 C16 H22 119.3(10) . . ?
C18 C17 C16 120.22(9) . . ?
C18 C17 H23 119.1(9) . . ?
C16 C17 H23 120.7(9) . . ?
C17 C18 C13 119.14(9) . . ?
C17 C18 H24 120.6(8) . . ?
C13 C18 H24 120.2(8) . . ?
F2 C19 F3 106.34(10) . . ?
F2 C19 F1 107.14(10) . . ?
F3 C19 F1 105.82(10) . . ?
F2 C19 C15 112.65(9) . . ?
F3 C19 C15 111.90(9) . . ?
F1 C19 C15 112.53(10) . . ?

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
O2 S1 N1 C1 -43.17(9) . . . . ?
O1 S1 N1 C1 -172.76(8) . . . . ?
C13 S1 N1 C1 73.72(9) . . . . ?
S1 N1 C1 C2 72.29(11) . . . . ?
S1 N1 C1 C6 -51.28(11) . . . . ?
S1 N1 C1 C7 -170.26(8) . . . . ?
N1 C1 C2 C3 175.09(8) . . . . ?
C6 C1 C2 C3 -59.11(11) . . . . ?
C7 C1 C2 C3 59.95(11) . . . . ?
C1 C2 C3 C11 178.51(10) . . . . ?
C1 C2 C3 C4 58.18(11) . . . . ?
C1 C2 C3 C9 -59.66(11) . . . . ?
C11 C3 C4 C5 -178.73(10) . . . . ?
C2 C3 C4 C5 -58.81(11) . . . . ?
C9 C3 C4 C5 59.13(11) . . . . ?
C3 C4 C5 C12 179.20(9) . . . . ?
C3 C4 C5 C10 -58.80(11) . . . . ?
C3 C4 C5 C6 58.90(11) . . . . ?
N1 C1 C6 C5 -176.57(8) . . . . ?
C2 C1 C6 C5 59.26(10) . . . . ?
C7 C1 C6 C5 -59.77(10) . . . . ?
C12 C5 C6 C1 -179.41(9) . . . . ?
C4 C5 C6 C1 -58.46(10) . . . . ?
C10 C5 C6 C1 59.05(10) . . . . ?
N1 C1 C7 C8 -178.02(9) . . . . ?
C2 C1 C7 C8 -59.41(11) . . . . ?
C6 C1 C7 C8 60.03(11) . . . . ?
C1 C7 C8 C10 -60.42(12) . . . . ?
C1 C7 C8 C9 59.71(12) . . . . ?
C11 C3 C9 C8 179.87(10) . . . . ?
C2 C3 C9 C8 59.16(11) . . . . ?
C4 C3 C9 C8 -58.71(12) . . . . ?
C10 C8 C9 C3 59.99(12) . . . . ?
C7 C8 C9 C3 -59.75(12) . . . . ?
C9 C8 C10 C5 -59.81(12) . . . . ?
C7 C8 C10 C5 60.14(12) . . . . ?
C12 C5 C10 C8 -179.84(9) . . . . ?
C4 C5 C10 C8 58.30(11) . . . . ?
C6 C5 C10 C8 -59.10(11) . . . . ?
O2 S1 C13 C14 -2.94(9) . . . . ?
O1 S1 C13 C14 125.62(8) . . . . ?
N1 S1 C13 C14 -121.51(8) . . . . ?
O2 S1 C13 C18 176.67(8) . . . . ?
O1 S1 C13 C18 -54.76(9) . . . . ?
N1 S1 C13 C18 58.11(9) . . . . ?
C18 C13 C14 C15 0.08(15) . . . . ?
S1 C13 C14 C15 179.69(7) . . . . ?
C13 C14 C15 C16 -0.17(15) . . . . ?
C13 C14 C15 C19 -177.33(9) . . . . ?
C14 C15 C16 C17 0.23(15) . . . . ?
C19 C15 C16 C17 177.35(10) . . . . ?
C15 C16 C17 C18 -0.20(16) . . . . ?
C16 C17 C18 C13 0.10(15) . . . . ?
C14 C13 C18 C17 -0.05(15) . . . . ?
S1 C13 C18 C17 -179.65(8) . . . . ?
C16 C15 C19 F2 143.48(10) . . . . ?
C14 C15 C19 F2 -39.34(14) . . . . ?
C16 C15 C19 F3 -96.76(12) . . . . ?
C14 C15 C19 F3 80.42(12) . . . . ?
C16 C15 C19 F1 22.23(15) . . . . ?
C14 C15 C19 F1 -160.59(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.878(15) 2.045(15) 2.9149(12) 170.8(14) 3_665
C2 H3 O2 0.989(14) 2.478(14) 3.1301(13) 123.1(10) .

####################################################################### 
# 
# 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_19_350K
_database_code_depnum_ccdc_archive 'CCDC 1962773'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2019-10-31 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;

_audit_creation_date             2017-08-12T16:08:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C20 H28 N2 O3 S'
_chemical_formula_sum            'C20 H28 N2 O3 S'
_chemical_formula_weight         376.5

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.645(4)
_cell_length_b                   15.735(3)
_cell_length_c                   14.349(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.347(7)
_cell_angle_gamma                90
_cell_volume                     4041.1(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    350(2)
_cell_measurement_reflns_used    3831
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      24.41

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.26
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1616

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

_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.6611
_exptl_absorpt_correction_T_max  0.7455

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

_diffrn_ambient_temperature      350(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_number            14383
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.276
_diffrn_reflns_theta_max         27.112
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_reflns_Friedel_coverage         0
_reflns_number_total             4409
_reflns_number_gt                3147
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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)+(0.0800P)²+1.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4409
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1646
_refine_ls_wR_factor_gt          0.1496
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.05

#----------------------------------------------------------------------------#
#                   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 0.11649(3) 0.12227(3) 0.65316(4) 0.04408(19) Uani 1 1 d . . . . .
O1 O 0.18310(10) 0.12586(11) 0.74646(12) 0.0597(5) Uani 1 1 d . . . . .
O2 O 0.06279(10) 0.05741(10) 0.64374(13) 0.0616(5) Uani 1 1 d . . . . .
O3 O 0.31109(10) 0.15598(12) 0.35152(15) 0.0674(5) Uani 1 1 d . . . . .
N1 N 0.07804(9) 0.21447(10) 0.64148(13) 0.0410(4) Uani 1 1 d . . . . .
H1A H 0.104739 0.253609 0.681859 0.049 Uiso 1 1 calc R U . . .
N2 N 0.23140(11) 0.04859(12) 0.33755(14) 0.0508(5) Uani 1 1 d . . . . .
H2C H 0.213773 0.002118 0.304992 0.061 Uiso 1 1 calc R U . . .
C1 C 0.00164(11) 0.23922(14) 0.56869(17) 0.0461(5) Uani 1 1 d . . . . .
C2 C -0.00966(15) 0.2304(2) 0.4584(2) 0.0771(9) Uani 1 1 d . . . . .
H2A H -0.0036 0.171364 0.443875 0.093 Uiso 1 1 calc R U . . .
H2B H 0.027756 0.263608 0.446857 0.093 Uiso 1 1 calc R U . . .
C3 C -0.0885(2) 0.2613(3) 0.3858(3) 0.1080(14) Uani 1 1 d . . . . .
C4 C -0.09487(18) 0.3551(2) 0.4120(3) 0.0956(11) Uani 1 1 d . . . . .
H4A H -0.057431 0.388201 0.400413 0.115 Uiso 1 1 calc R U . . .
H4B H -0.143638 0.376614 0.366786 0.115 Uiso 1 1 calc R U . . .
C5 C -0.08435(15) 0.36616(18) 0.5221(3) 0.0717(8) Uani 1 1 d . . . . .
C6 C -0.00652(13) 0.33202(15) 0.5911(2) 0.0547(6) Uani 1 1 d . . . . .
H6A H 0.031184 0.3653 0.58034 0.066 Uiso 1 1 calc R U . . .
H6B H 0.001591 0.338093 0.662176 0.066 Uiso 1 1 calc R U . . .
C7 C -0.05760(14) 0.1886(2) 0.5885(3) 0.0844(10) Uani 1 1 d . . . . .
H7A H -0.053822 0.128781 0.574996 0.101 Uiso 1 1 calc R U . . .
H7B H -0.049917 0.194757 0.659406 0.101 Uiso 1 1 calc R U . . .
C8 C -0.13478(17) 0.2223(3) 0.5181(4) 0.1130(15) Uani 1 1 d . . . . .
H8A H -0.172563 0.189448 0.53066 0.136 Uiso 1 1 calc R U . . .
C9 C -0.1467(2) 0.2099(3) 0.4108(4) 0.138(2) Uani 1 1 d . . . . .
H9A H -0.196779 0.228243 0.366123 0.166 Uiso 1 1 calc R U . . .
H9B H -0.142392 0.14997 0.398356 0.166 Uiso 1 1 calc R U . . .
C10 C -0.14187(16) 0.3141(2) 0.5421(3) 0.1000(12) Uani 1 1 d . . . . .
H10A H -0.133924 0.319849 0.613162 0.12 Uiso 1 1 calc R U . . .
H10B H -0.19167 0.334597 0.499603 0.12 Uiso 1 1 calc R U . . .
C11 C -0.0970(3) 0.2524(4) 0.2759(3) 0.209(3) Uani 1 1 d . . . . .
H11A H -0.092833 0.19364 0.26119 0.313 Uiso 1 1 calc R U . . .
H11B H -0.145029 0.273632 0.230174 0.313 Uiso 1 1 calc R U . . .
H11C H -0.058494 0.284452 0.267001 0.313 Uiso 1 1 calc R U . . .
C12 C -0.0899(2) 0.4598(2) 0.5495(4) 0.1206(15) Uani 1 1 d . . . . .
H12A H -0.053521 0.492824 0.53695 0.181 Uiso 1 1 calc R U . . .
H12B H -0.139049 0.480904 0.508276 0.181 Uiso 1 1 calc R U . . .
H12C H -0.080685 0.463873 0.620514 0.181 Uiso 1 1 calc R U . . .
C13 C 0.14705(11) 0.10565(12) 0.55493(15) 0.0398(5) Uani 1 1 d . . . . .
C14 C 0.21012(13) 0.14760(14) 0.55862(17) 0.0487(5) Uani 1 1 d . . . . .
H14A H 0.233602 0.187339 0.609867 0.058 Uiso 1 1 calc R U . . .
C15 C 0.23843(13) 0.13107(14) 0.48716(18) 0.0508(6) Uani 1 1 d . . . . .
H15A H 0.280721 0.159738 0.490295 0.061 Uiso 1 1 calc R U . . .
C16 C 0.20407(12) 0.07188(13) 0.41073(16) 0.0428(5) Uani 1 1 d . . . . .
C17 C 0.14015(14) 0.03085(15) 0.40661(19) 0.0559(6) Uani 1 1 d . . . . .
H17A H 0.116154 -0.008305 0.354847 0.067 Uiso 1 1 calc R U . . .
C18 C 0.11199(14) 0.04735(15) 0.47791(19) 0.0535(6) Uani 1 1 d . . . . .
H18A H 0.069326 0.019279 0.474348 0.064 Uiso 1 1 calc R U . . .
C19 C 0.28152(12) 0.08954(15) 0.31186(18) 0.0479(5) Uani 1 1 d . . . . .
C20 C 0.29870(16) 0.04757(18) 0.2304(2) 0.0675(7) Uani 1 1 d . . . . .
H20A H 0.270088 -0.003791 0.20881 0.101 Uiso 1 1 calc R U . . .
H20B H 0.286037 0.085301 0.173142 0.101 Uiso 1 1 calc R U . . .
H20C H 0.351002 0.034281 0.257135 0.101 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 O2 1.4336(17) . ?
S1 O1 1.4364(17) . ?
S1 N1 1.6120(17) . ?
S1 C13 1.764(2) . ?
O3 C19 1.217(3) . ?
N1 C1 1.484(3) . ?
N1 H1A 0.86 . ?
N2 C19 1.349(3) . ?
N2 C16 1.411(3) . ?
N2 H2C 0.86 . ?
C1 C2 1.511(3) . ?
C1 C6 1.518(3) . ?
C1 C7 1.530(3) . ?
C2 C3 1.546(4) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 C11 1.523(6) . ?
C3 C4 1.540(5) . ?
C3 C9 1.560(6) . ?
C4 C5 1.517(5) . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C5 C10 1.515(4) . ?
C5 C6 1.535(3) . ?
C5 C12 1.540(4) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.529(4) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.472(6) . ?
C8 C10 1.505(5) . ?
C8 H8A 0.98 . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 H11A 0.96 . ?
C11 H11B 0.96 . ?
C11 H11C 0.96 . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 C18 1.382(3) . ?
C13 C14 1.386(3) . ?
C14 C15 1.378(3) . ?
C14 H14A 0.93 . ?
C15 C16 1.384(3) . ?
C15 H15A 0.93 . ?
C16 C17 1.391(3) . ?
C17 C18 1.374(3) . ?
C17 H17A 0.93 . ?
C18 H18A 0.93 . ?
C19 C20 1.497(3) . ?
C20 H20A 0.96 . ?
C20 H20B 0.96 . ?
C20 H20C 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
O2 S1 O1 117.91(10) . . ?
O2 S1 N1 109.62(10) . . ?
O1 S1 N1 105.62(9) . . ?
O2 S1 C13 107.38(10) . . ?
O1 S1 C13 105.73(10) . . ?
N1 S1 C13 110.46(9) . . ?
C1 N1 S1 127.15(14) . . ?
C1 N1 H1A 116.4 . . ?
S1 N1 H1A 116.4 . . ?
C19 N2 C16 128.61(18) . . ?
C19 N2 H2C 115.7 . . ?
C16 N2 H2C 115.7 . . ?
N1 C1 C2 112.47(19) . . ?
N1 C1 C6 105.54(17) . . ?
C2 C1 C6 109.1(2) . . ?
N1 C1 C7 111.02(19) . . ?
C2 C1 C7 110.6(2) . . ?
C6 C1 C7 107.9(2) . . ?
C1 C2 C3 110.5(2) . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C11 C3 C4 110.8(4) . . ?
C11 C3 C2 108.7(3) . . ?
C4 C3 C2 107.3(3) . . ?
C11 C3 C9 114.4(4) . . ?
C4 C3 C9 107.4(3) . . ?
C2 C3 C9 107.9(3) . . ?
C5 C4 C3 112.0(3) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C10 C5 C4 110.1(3) . . ?
C10 C5 C6 108.1(2) . . ?
C4 C5 C6 107.6(2) . . ?
C10 C5 C12 109.3(3) . . ?
C4 C5 C12 112.5(3) . . ?
C6 C5 C12 109.1(3) . . ?
C1 C6 C5 111.4(2) . . ?
C1 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C1 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108 . . ?
C8 C7 C1 108.7(3) . . ?
C8 C7 H7A 110 . . ?
C1 C7 H7A 110 . . ?
C8 C7 H7B 110 . . ?
C1 C7 H7B 110 . . ?
H7A C7 H7B 108.3 . . ?
C9 C8 C10 112.1(4) . . ?
C9 C8 C7 109.4(3) . . ?
C10 C8 C7 110.0(3) . . ?
C9 C8 H8A 108.4 . . ?
C10 C8 H8A 108.4 . . ?
C7 C8 H8A 108.4 . . ?
C8 C9 C3 110.8(3) . . ?
C8 C9 H9A 109.5 . . ?
C3 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C3 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C8 C10 C5 109.2(3) . . ?
C8 C10 H10A 109.8 . . ?
C5 C10 H10A 109.8 . . ?
C8 C10 H10B 109.8 . . ?
C5 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 119.3(2) . . ?
C18 C13 S1 121.05(17) . . ?
C14 C13 S1 119.49(16) . . ?
C15 C14 C13 120.71(19) . . ?
C15 C14 H14A 119.6 . . ?
C13 C14 H14A 119.6 . . ?
C14 C15 C16 120.1(2) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C15 C16 C17 118.9(2) . . ?
C15 C16 N2 123.6(2) . . ?
C17 C16 N2 117.50(18) . . ?
C18 C17 C16 120.9(2) . . ?
C18 C17 H17A 119.5 . . ?
C16 C17 H17A 119.5 . . ?
C17 C18 C13 120.0(2) . . ?
C17 C18 H18A 120 . . ?
C13 C18 H18A 120 . . ?
O3 C19 N2 122.9(2) . . ?
O3 C19 C20 121.7(2) . . ?
N2 C19 C20 115.3(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O2 S1 N1 C1 -40.2(2) . . . . ?
O1 S1 N1 C1 -168.17(17) . . . . ?
C13 S1 N1 C1 77.96(19) . . . . ?
S1 N1 C1 C2 -62.1(3) . . . . ?
S1 N1 C1 C6 179.01(16) . . . . ?
S1 N1 C1 C7 62.4(3) . . . . ?
N1 C1 C2 C3 -177.0(3) . . . . ?
C6 C1 C2 C3 -60.3(3) . . . . ?
C7 C1 C2 C3 58.2(3) . . . . ?
C1 C2 C3 C11 179.2(4) . . . . ?
C1 C2 C3 C4 59.4(4) . . . . ?
C1 C2 C3 C9 -56.2(4) . . . . ?
C11 C3 C4 C5 -178.3(3) . . . . ?
C2 C3 C4 C5 -59.8(4) . . . . ?
C9 C3 C4 C5 56.0(4) . . . . ?
C3 C4 C5 C10 -58.3(3) . . . . ?
C3 C4 C5 C6 59.3(4) . . . . ?
C3 C4 C5 C12 179.5(3) . . . . ?
N1 C1 C6 C5 -178.9(2) . . . . ?
C2 C1 C6 C5 60.1(3) . . . . ?
C7 C1 C6 C5 -60.1(3) . . . . ?
C10 C5 C6 C1 60.1(3) . . . . ?
C4 C5 C6 C1 -58.7(3) . . . . ?
C12 C5 C6 C1 178.9(3) . . . . ?
N1 C1 C7 C8 174.9(3) . . . . ?
C2 C1 C7 C8 -59.5(4) . . . . ?
C6 C1 C7 C8 59.7(4) . . . . ?
C1 C7 C8 C9 61.5(4) . . . . ?
C1 C7 C8 C10 -62.0(4) . . . . ?
C10 C8 C9 C3 59.9(4) . . . . ?
C7 C8 C9 C3 -62.4(4) . . . . ?
C11 C3 C9 C8 -179.8(4) . . . . ?
C4 C3 C9 C8 -56.3(4) . . . . ?
C2 C3 C9 C8 59.1(4) . . . . ?
C9 C8 C10 C5 -59.8(4) . . . . ?
C7 C8 C10 C5 62.2(5) . . . . ?
C4 C5 C10 C8 57.6(4) . . . . ?
C6 C5 C10 C8 -59.7(4) . . . . ?
C12 C5 C10 C8 -178.4(3) . . . . ?
O2 S1 C13 C18 9.4(2) . . . . ?
O1 S1 C13 C18 136.06(19) . . . . ?
N1 S1 C13 C18 -110.13(19) . . . . ?
O2 S1 C13 C14 -166.41(17) . . . . ?
O1 S1 C13 C14 -39.7(2) . . . . ?
N1 S1 C13 C14 74.09(19) . . . . ?
C18 C13 C14 C15 -0.7(3) . . . . ?
S1 C13 C14 C15 175.16(18) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
C14 C15 C16 C17 1.1(4) . . . . ?
C14 C15 C16 N2 -177.1(2) . . . . ?
C19 N2 C16 C15 -16.8(4) . . . . ?
C19 N2 C16 C17 165.0(2) . . . . ?
C15 C16 C17 C18 -1.1(4) . . . . ?
N2 C16 C17 C18 177.2(2) . . . . ?
C16 C17 C18 C13 0.2(4) . . . . ?
C14 C13 C18 C17 0.7(4) . . . . ?
S1 C13 C18 C17 -175.12(19) . . . . ?
C16 N2 C19 O3 0.0(4) . . . . ?
C16 N2 C19 C20 180.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O3 0.86 2.38 2.955(2) 125.1 7_556
N2 H2C S1 0.86 2.97 3.7948(19) 162.4 6
N2 H2C O1 0.86 2.17 3.020(2) 170.1 6
C7 H7A O2 0.97 2.37 2.990(3) 121.1 .
C15 H15A O3 0.93 2.3 2.876(3) 119.4 .

####################################################################### 
# 
# 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_19_150K
_database_code_depnum_ccdc_archive 'CCDC 1962771'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2019-10-31 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;

_audit_creation_date             2017-05-07T22:55:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C20 H28 N2 O3 S'
_chemical_formula_sum            'C20 H28 N2 O3 S'
_chemical_formula_weight         376.5

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.8607(8)
_cell_length_b                   15.5920(7)
_cell_length_c                   14.1742(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.2060(10)
_cell_angle_gamma                90
_cell_volume                     3936.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7684
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      28.09

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.26
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1616

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

_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.6509
_exptl_absorpt_correction_T_max  0.7457

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

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_number            49779
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.045
_diffrn_reflns_theta_max         28.303
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_coverage         0
_reflns_number_total             9748
_reflns_number_gt                6361
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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)+(0.0800P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         9748
_refine_ls_number_parameters     475
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1505
_refine_ls_wR_factor_gt          0.1276
_refine_ls_goodness_of_fit_ref   1
_refine_ls_restrained_S_all      1
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.058

#----------------------------------------------------------------------------#
#                   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 0.13295(2) 0.37100(2) 0.79016(3) 0.01656(11) Uani 1 1 d . . . . .
S2 S 0.36369(2) 0.37358(2) 0.21202(3) 0.01737(11) Uani 1 1 d . . . . .
O1 O 0.06478(6) 0.37324(7) 0.81574(9) 0.0224(3) Uani 1 1 d . . . . .
O2 O 0.18698(7) 0.30512(7) 0.83374(9) 0.0232(3) Uani 1 1 d . . . . .
O3 O -0.06027(7) 0.41099(8) 0.28766(9) 0.0268(3) Uani 1 1 d . . . . .
O4 O 0.30935(7) 0.30845(7) 0.16720(9) 0.0249(3) Uani 1 1 d . . . . .
O5 O 0.43080(7) 0.37788(7) 0.18419(9) 0.0233(3) Uani 1 1 d . . . . .
O6 O 0.56187(7) 0.40421(8) 0.71473(9) 0.0271(3) Uani 1 1 d . . . . .
N1 N 0.17105(7) 0.46405(8) 0.82020(10) 0.0156(3) Uani 1 1 d . . . . .
H1A H 0.143468 0.504462 0.834156 0.019 Uiso 1 1 calc R U . . .
N2 N 0.01897(8) 0.30033(9) 0.35375(10) 0.0204(3) Uani 1 1 d . . . . .
H2C H 0.036312 0.25194 0.337979 0.024 Uiso 1 1 calc R U . . .
N3 N 0.32574(7) 0.46721(8) 0.18650(10) 0.0163(3) Uani 1 1 d . . . . .
H3A H 0.352237 0.507052 0.169363 0.02 Uiso 1 1 calc R U . . .
N4 N 0.48285(8) 0.29373(9) 0.64600(10) 0.0198(3) Uani 1 1 d . . . . .
H4C H 0.465467 0.245011 0.660873 0.024 Uiso 1 1 calc R U . . .
C1 C 0.24896(8) 0.48724(10) 0.82628(12) 0.0167(3) Uani 1 1 d . . . . .
C2 C 0.26572(9) 0.47071(12) 0.72960(13) 0.0243(4) Uani 1 1 d . . . . .
H2A H 0.228695 0.50154 0.673858 0.029 Uiso 1 1 calc R U . . .
H2B H 0.261086 0.408619 0.714154 0.029 Uiso 1 1 calc R U . . .
C3 C 0.34548(10) 0.50117(13) 0.73947(15) 0.0319(4) Uani 1 1 d . . . . .
C4 C 0.35136(10) 0.59760(13) 0.76375(15) 0.0322(4) Uani 1 1 d . . . . .
H4A H 0.402475 0.617969 0.770318 0.039 Uiso 1 1 calc R U . . .
H4B H 0.315191 0.629384 0.708039 0.039 Uiso 1 1 calc R U . . .
C5 C 0.33509(10) 0.61637(11) 0.86055(14) 0.0258(4) Uani 1 1 d . . . . .
C6 C 0.25546(9) 0.58385(10) 0.84853(13) 0.0199(3) Uani 1 1 d . . . . .
H6A H 0.243922 0.595308 0.910631 0.024 Uiso 1 1 calc R U . . .
H6B H 0.218415 0.61517 0.793269 0.024 Uiso 1 1 calc R U . . .
C7 C 0.30660(9) 0.43974(12) 0.91320(14) 0.0255(4) Uani 1 1 d . . . . .
H7A H 0.296076 0.450912 0.976068 0.031 Uiso 1 1 calc R U . . .
H7B H 0.302724 0.377197 0.90048 0.031 Uiso 1 1 calc R U . . .
C8 C 0.38577(10) 0.47053(13) 0.92345(15) 0.0336(5) Uani 1 1 d . . . . .
H8A H 0.423081 0.439025 0.979506 0.04 Uiso 1 1 calc R U . . .
C9 C 0.40201(10) 0.45334(14) 0.82674(17) 0.0388(5) Uani 1 1 d . . . . .
H9A H 0.39876 0.390988 0.81277 0.047 Uiso 1 1 calc R U . . .
H9B H 0.453575 0.472495 0.833971 0.047 Uiso 1 1 calc R U . . .
C10 C 0.39148(10) 0.56669(13) 0.94626(15) 0.0330(5) Uani 1 1 d . . . . .
H10A H 0.443041 0.58685 0.955096 0.04 Uiso 1 1 calc R U . . .
H10B H 0.380989 0.577471 1.009228 0.04 Uiso 1 1 calc R U . . .
C11 C 0.36058(13) 0.48352(18) 0.64158(18) 0.0550(7) Uani 1 1 d . . . . .
H11A H 0.352501 0.422517 0.624857 0.083 Uiso 1 1 calc R U . . .
H11B H 0.412585 0.498813 0.649274 0.083 Uiso 1 1 calc R U . . .
H11C H 0.326325 0.517935 0.58793 0.083 Uiso 1 1 calc R U . . .
C12 C 0.34022(12) 0.71252(12) 0.88445(17) 0.0399(5) Uani 1 1 d . . . . .
H12A H 0.392238 0.731755 0.899517 0.06 Uiso 1 1 calc R U . . .
H12B H 0.323958 0.722966 0.942377 0.06 Uiso 1 1 calc R U . . .
H12C H 0.307732 0.744301 0.826734 0.06 Uiso 1 1 calc R U . . .
C13 C 0.10297(9) 0.35606(10) 0.65925(12) 0.0170(3) Uani 1 1 d . . . . .
C14 C 0.03947(9) 0.39913(10) 0.59996(12) 0.0197(3) Uani 1 1 d . . . . .
H14A H 0.015491 0.43972 0.629344 0.024 Uiso 1 1 calc R U . . .
C15 C 0.01086(9) 0.38323(10) 0.49807(13) 0.0205(4) Uani 1 1 d . . . . .
H15A H -0.032514 0.412804 0.457563 0.025 Uiso 1 1 calc R U . . .
C16 C 0.04639(9) 0.32342(10) 0.45576(12) 0.0184(3) Uani 1 1 d . . . . .
C17 C 0.11097(9) 0.28135(11) 0.51544(13) 0.0234(4) Uani 1 1 d . . . . .
H17A H 0.135637 0.241559 0.48605 0.028 Uiso 1 1 calc R U . . .
C18 C 0.13924(9) 0.29721(11) 0.61698(13) 0.0222(4) Uani 1 1 d . . . . .
H18A H 0.18297 0.268242 0.657494 0.027 Uiso 1 1 calc R U . . .
C19 C -0.03073(9) 0.34333(11) 0.27703(12) 0.0195(3) Uani 1 1 d . . . . .
C20 C -0.04757(10) 0.30229(12) 0.17594(13) 0.0277(4) Uani 1 1 d . . . . .
H20A H -0.102011 0.300905 0.142194 0.042 Uiso 1 1 calc R U . . .
H20B H -0.027816 0.243634 0.183964 0.042 Uiso 1 1 calc R U . . .
H20C H -0.023858 0.335609 0.135835 0.042 Uiso 1 1 calc R U . . .
C21 C 0.25025(9) 0.49296(10) 0.18907(12) 0.0194(3) Uani 1 1 d . . . . .
C22 C 0.24441(10) 0.48880(13) 0.29391(14) 0.0314(4) Uani 1 1 d . . . . .
H22A H 0.285102 0.523444 0.340221 0.038 Uiso 1 1 calc R U . . .
H22B H 0.250703 0.428709 0.317778 0.038 Uiso 1 1 calc R U . . .
C23 C 0.16767(11) 0.52299(16) 0.29401(16) 0.0428(6) Uani 1 1 d . . . . .
C24 C 0.15889(11) 0.61617(14) 0.25617(15) 0.0376(5) Uani 1 1 d . . . . .
H24A H 0.109571 0.638602 0.255301 0.045 Uiso 1 1 calc R U . . .
H24B H 0.198464 0.652064 0.302597 0.045 Uiso 1 1 calc R U . . .
C25 C 0.16458(10) 0.62260(12) 0.15101(14) 0.0272(4) Uani 1 1 d . . . . .
C26 C 0.24123(9) 0.58658(10) 0.15397(13) 0.0215(4) Uani 1 1 d . . . . .
H26A H 0.245817 0.590225 0.08648 0.026 Uiso 1 1 calc R U . . .
H26B H 0.281808 0.621608 0.199904 0.026 Uiso 1 1 calc R U . . .
C27 C 0.18727(10) 0.43960(12) 0.11661(17) 0.0349(5) Uani 1 1 d . . . . .
H27A H 0.190679 0.442945 0.048487 0.042 Uiso 1 1 calc R U . . .
H27B H 0.192428 0.378748 0.137718 0.042 Uiso 1 1 calc R U . . .
C28 C 0.11115(10) 0.47451(14) 0.11632(18) 0.0437(6) Uani 1 1 d . . . . .
H28A H 0.070164 0.43916 0.069884 0.052 Uiso 1 1 calc R U . . .
C29 C 0.10577(12) 0.46920(16) 0.2206(2) 0.0549(7) Uani 1 1 d . . . . .
H29A H 0.110672 0.408674 0.242933 0.066 Uiso 1 1 calc R U . . .
H29B H 0.056022 0.490341 0.219575 0.066 Uiso 1 1 calc R U . . .
C30 C 0.10256(10) 0.56765(14) 0.07963(16) 0.0383(5) Uani 1 1 d . . . . .
H30A H 0.106056 0.570403 0.011518 0.046 Uiso 1 1 calc R U . . .
H30B H 0.052756 0.589902 0.076868 0.046 Uiso 1 1 calc R U . . .
C31 C 0.16359(15) 0.5185(2) 0.3996(2) 0.0797(11) Uani 1 1 d . . . . .
H31A H 0.168644 0.458676 0.422175 0.119 Uiso 1 1 calc R U . . .
H31B H 0.115171 0.541154 0.399765 0.119 Uiso 1 1 calc R U . . .
H31C H 0.204331 0.55266 0.444733 0.119 Uiso 1 1 calc R U . . .
C32 C 0.15753(12) 0.71591(13) 0.11480(18) 0.0427(5) Uani 1 1 d . . . . .
H32A H 0.194846 0.751265 0.163829 0.064 Uiso 1 1 calc R U . . .
H32B H 0.107048 0.73723 0.107027 0.064 Uiso 1 1 calc R U . . .
H32C H 0.166212 0.71884 0.050396 0.064 Uiso 1 1 calc R U . . .
C33 C 0.39542(9) 0.35555(10) 0.34247(12) 0.0169(3) Uani 1 1 d . . . . .
C34 C 0.45890(9) 0.39856(11) 0.40222(13) 0.0216(4) Uani 1 1 d . . . . .
H34A H 0.482109 0.440432 0.373382 0.026 Uiso 1 1 calc R U . . .
C35 C 0.48852(9) 0.38095(11) 0.50313(13) 0.0215(4) Uani 1 1 d . . . . .
H35A H 0.531775 0.410645 0.543769 0.026 Uiso 1 1 calc R U . . .
C36 C 0.45423(9) 0.31905(10) 0.54482(12) 0.0173(3) Uani 1 1 d . . . . .
C37 C 0.38960(9) 0.27742(11) 0.48522(13) 0.0230(4) Uani 1 1 d . . . . .
H37A H 0.365512 0.236663 0.514243 0.028 Uiso 1 1 calc R U . . .
C38 C 0.36024(9) 0.29508(11) 0.38386(12) 0.0221(4) Uani 1 1 d . . . . .
H38A H 0.316541 0.266141 0.343186 0.027 Uiso 1 1 calc R U . . .
C39 C 0.53380(9) 0.33504(11) 0.72327(12) 0.0196(3) Uani 1 1 d . . . . .
C40 C 0.55366(10) 0.28911(12) 0.82206(13) 0.0271(4) Uani 1 1 d . . . . .
H40A H 0.608191 0.290564 0.855029 0.041 Uiso 1 1 calc R U . . .
H40B H 0.536773 0.229393 0.810892 0.041 Uiso 1 1 calc R U . . .
H40C H 0.528943 0.317501 0.864533 0.041 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 O2 1.4357(12) . ?
S1 O1 1.4465(12) . ?
S1 N1 1.6128(13) . ?
S1 C13 1.7683(16) . ?
S2 O4 1.4342(12) . ?
S2 O5 1.4457(12) . ?
S2 N3 1.6138(13) . ?
S2 C33 1.7686(16) . ?
O3 C19 1.225(2) . ?
O6 C39 1.225(2) . ?
N1 C1 1.4880(19) . ?
N1 H1A 0.88 . ?
N2 C19 1.356(2) . ?
N2 C16 1.413(2) . ?
N2 H2C 0.88 . ?
N3 C21 1.4913(19) . ?
N3 H3A 0.88 . ?
N4 C39 1.358(2) . ?
N4 C36 1.412(2) . ?
N4 H4C 0.88 . ?
C1 C2 1.526(2) . ?
C1 C6 1.535(2) . ?
C1 C7 1.539(2) . ?
C2 C3 1.539(2) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C11 1.530(3) . ?
C3 C9 1.535(3) . ?
C3 C4 1.538(3) . ?
C4 C5 1.529(3) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 C12 1.533(2) . ?
C5 C10 1.535(3) . ?
C5 C6 1.541(2) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 C8 1.529(2) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 C9 1.524(3) . ?
C8 C10 1.530(3) . ?
C8 H8A 1 . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 C14 1.389(2) . ?
C13 C18 1.392(2) . ?
C14 C15 1.388(2) . ?
C14 H14A 0.95 . ?
C15 C16 1.394(2) . ?
C15 H15A 0.95 . ?
C16 C17 1.397(2) . ?
C17 C18 1.383(2) . ?
C17 H17A 0.95 . ?
C18 H18A 0.95 . ?
C19 C20 1.505(2) . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C21 C22 1.527(2) . ?
C21 C26 1.533(2) . ?
C21 C27 1.535(2) . ?
C22 C23 1.543(2) . ?
C22 H22A 0.99 . ?
C22 H22B 0.99 . ?
C23 C31 1.525(3) . ?
C23 C29 1.533(3) . ?
C23 C24 1.539(3) . ?
C24 C25 1.533(3) . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
C25 C30 1.532(3) . ?
C25 C32 1.534(3) . ?
C25 C26 1.539(2) . ?
C26 H26A 0.99 . ?
C26 H26B 0.99 . ?
C27 C28 1.534(3) . ?
C27 H27A 0.99 . ?
C27 H27B 0.99 . ?
C28 C29 1.517(3) . ?
C28 C30 1.533(3) . ?
C28 H28A 1 . ?
C29 H29A 0.99 . ?
C29 H29B 0.99 . ?
C30 H30A 0.99 . ?
C30 H30B 0.99 . ?
C31 H31A 0.98 . ?
C31 H31B 0.98 . ?
C31 H31C 0.98 . ?
C32 H32A 0.98 . ?
C32 H32B 0.98 . ?
C32 H32C 0.98 . ?
C33 C38 1.389(2) . ?
C33 C34 1.390(2) . ?
C34 C35 1.381(2) . ?
C34 H34A 0.95 . ?
C35 C36 1.397(2) . ?
C35 H35A 0.95 . ?
C36 C37 1.394(2) . ?
C37 C38 1.387(2) . ?
C37 H37A 0.95 . ?
C38 H38A 0.95 . ?
C39 C40 1.506(2) . ?
C40 H40A 0.98 . ?
C40 H40B 0.98 . ?
C40 H40C 0.98 . ?

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
O2 S1 O1 118.23(7) . . ?
O2 S1 N1 109.79(7) . . ?
O1 S1 N1 105.53(7) . . ?
O2 S1 C13 107.09(7) . . ?
O1 S1 C13 105.21(7) . . ?
N1 S1 C13 110.88(7) . . ?
O4 S2 O5 118.32(7) . . ?
O4 S2 N3 109.97(7) . . ?
O5 S2 N3 105.09(7) . . ?
O4 S2 C33 107.29(7) . . ?
O5 S2 C33 105.49(7) . . ?
N3 S2 C33 110.53(7) . . ?
C1 N1 S1 125.42(10) . . ?
C1 N1 H1A 117.3 . . ?
S1 N1 H1A 117.3 . . ?
C19 N2 C16 128.20(14) . . ?
C19 N2 H2C 115.9 . . ?
C16 N2 H2C 115.9 . . ?
C21 N3 S2 126.49(11) . . ?
C21 N3 H3A 116.8 . . ?
S2 N3 H3A 116.8 . . ?
C39 N4 C36 128.23(14) . . ?
C39 N4 H4C 115.9 . . ?
C36 N4 H4C 115.9 . . ?
N1 C1 C2 113.53(13) . . ?
N1 C1 C6 105.12(12) . . ?
C2 C1 C6 108.90(13) . . ?
N1 C1 C7 110.71(13) . . ?
C2 C1 C7 109.70(14) . . ?
C6 C1 C7 108.67(13) . . ?
C1 C2 C3 110.56(14) . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C11 C3 C9 110.87(17) . . ?
C11 C3 C4 110.94(17) . . ?
C9 C3 C4 108.35(16) . . ?
C11 C3 C2 109.26(16) . . ?
C9 C3 C2 108.80(16) . . ?
C4 C3 C2 108.55(15) . . ?
C5 C4 C3 111.52(15) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108 . . ?
C4 C5 C12 111.64(16) . . ?
C4 C5 C10 108.79(15) . . ?
C12 C5 C10 109.97(16) . . ?
C4 C5 C6 108.29(14) . . ?
C12 C5 C6 109.55(15) . . ?
C10 C5 C6 108.53(14) . . ?
C1 C6 C5 110.77(13) . . ?
C1 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C1 109.61(14) . . ?
C8 C7 H7A 109.7 . . ?
C1 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
C1 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C7 109.78(16) . . ?
C9 C8 C10 109.97(17) . . ?
C7 C8 C10 109.05(15) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C10 C8 H8A 109.3 . . ?
C8 C9 C3 110.35(15) . . ?
C8 C9 H9A 109.6 . . ?
C3 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C3 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C8 C10 C5 110.17(15) . . ?
C8 C10 H10A 109.6 . . ?
C5 C10 H10A 109.6 . . ?
C8 C10 H10B 109.6 . . ?
C5 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 120.41(15) . . ?
C14 C13 S1 119.05(12) . . ?
C18 C13 S1 120.37(12) . . ?
C15 C14 C13 120.40(15) . . ?
C15 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
C14 C15 C16 119.34(15) . . ?
C14 C15 H15A 120.3 . . ?
C16 C15 H15A 120.3 . . ?
C15 C16 C17 120.03(15) . . ?
C15 C16 N2 123.01(14) . . ?
C17 C16 N2 116.93(14) . . ?
C18 C17 C16 120.48(15) . . ?
C18 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
C17 C18 C13 119.34(15) . . ?
C17 C18 H18A 120.3 . . ?
C13 C18 H18A 120.3 . . ?
O3 C19 N2 123.32(15) . . ?
O3 C19 C20 121.41(15) . . ?
N2 C19 C20 115.27(14) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 C22 112.79(13) . . ?
N3 C21 C26 104.66(13) . . ?
C22 C21 C26 108.68(14) . . ?
N3 C21 C27 111.89(14) . . ?
C22 C21 C27 109.91(15) . . ?
C26 C21 C27 108.67(14) . . ?
C21 C22 C23 110.74(15) . . ?
C21 C22 H22A 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C31 C23 C29 111.6(2) . . ?
C31 C23 C24 110.6(2) . . ?
C29 C23 C24 108.02(18) . . ?
C31 C23 C22 109.58(17) . . ?
C29 C23 C22 108.40(19) . . ?
C24 C23 C22 108.63(16) . . ?
C25 C24 C23 111.52(16) . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24A 109.3 . . ?
C25 C24 H24B 109.3 . . ?
C23 C24 H24B 109.3 . . ?
H24A C24 H24B 108 . . ?
C30 C25 C24 108.86(17) . . ?
C30 C25 C32 110.26(16) . . ?
C24 C25 C32 111.19(16) . . ?
C30 C25 C26 108.68(15) . . ?
C24 C25 C26 108.39(14) . . ?
C32 C25 C26 109.42(16) . . ?
C21 C26 C25 111.05(14) . . ?
C21 C26 H26A 109.4 . . ?
C25 C26 H26A 109.4 . . ?
C21 C26 H26B 109.4 . . ?
C25 C26 H26B 109.4 . . ?
H26A C26 H26B 108 . . ?
C28 C27 C21 109.09(16) . . ?
C28 C27 H27A 109.9 . . ?
C21 C27 H27A 109.9 . . ?
C28 C27 H27B 109.9 . . ?
C21 C27 H27B 109.9 . . ?
H27A C27 H27B 108.3 . . ?
C29 C28 C30 110.42(19) . . ?
C29 C28 C27 109.92(18) . . ?
C30 C28 C27 109.35(17) . . ?
C29 C28 H28A 109 . . ?
C30 C28 H28A 109 . . ?
C27 C28 H28A 109 . . ?
C28 C29 C23 110.57(17) . . ?
C28 C29 H29A 109.5 . . ?
C23 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C23 C29 H29B 109.5 . . ?
H29A C29 H29B 108.1 . . ?
C25 C30 C28 109.46(16) . . ?
C25 C30 H30A 109.8 . . ?
C28 C30 H30A 109.8 . . ?
C25 C30 H30B 109.8 . . ?
C28 C30 H30B 109.8 . . ?
H30A C30 H30B 108.2 . . ?
C23 C31 H31A 109.5 . . ?
C23 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C23 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C25 C32 H32A 109.5 . . ?
C25 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C25 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C38 C33 C34 120.36(15) . . ?
C38 C33 S2 120.33(12) . . ?
C34 C33 S2 119.18(12) . . ?
C35 C34 C33 120.58(15) . . ?
C35 C34 H34A 119.7 . . ?
C33 C34 H34A 119.7 . . ?
C34 C35 C36 119.32(15) . . ?
C34 C35 H35A 120.3 . . ?
C36 C35 H35A 120.3 . . ?
C37 C36 C35 119.98(15) . . ?
C37 C36 N4 116.81(14) . . ?
C35 C36 N4 123.19(14) . . ?
C38 C37 C36 120.46(15) . . ?
C38 C37 H37A 119.8 . . ?
C36 C37 H37A 119.8 . . ?
C37 C38 C33 119.26(15) . . ?
C37 C38 H38A 120.4 . . ?
C33 C38 H38A 120.4 . . ?
O6 C39 N4 123.50(15) . . ?
O6 C39 C40 121.81(15) . . ?
N4 C39 C40 114.69(14) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 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
O2 S1 N1 C1 39.11(14) . . . . ?
O1 S1 N1 C1 167.56(12) . . . . ?
C13 S1 N1 C1 -79.02(14) . . . . ?
O4 S2 N3 C21 43.20(15) . . . . ?
O5 S2 N3 C21 171.57(12) . . . . ?
C33 S2 N3 C21 -75.08(14) . . . . ?
S1 N1 C1 C2 56.30(18) . . . . ?
S1 N1 C1 C6 175.23(11) . . . . ?
S1 N1 C1 C7 -67.60(17) . . . . ?
N1 C1 C2 C3 176.60(14) . . . . ?
C6 C1 C2 C3 59.87(18) . . . . ?
C7 C1 C2 C3 -58.96(19) . . . . ?
C1 C2 C3 C11 179.86(17) . . . . ?
C1 C2 C3 C9 58.7(2) . . . . ?
C1 C2 C3 C4 -59.0(2) . . . . ?
C11 C3 C4 C5 179.04(16) . . . . ?
C9 C3 C4 C5 -59.03(19) . . . . ?
C2 C3 C4 C5 59.0(2) . . . . ?
C3 C4 C5 C12 -179.50(15) . . . . ?
C3 C4 C5 C10 58.96(19) . . . . ?
C3 C4 C5 C6 -58.81(19) . . . . ?
N1 C1 C6 C5 178.02(13) . . . . ?
C2 C1 C6 C5 -59.99(17) . . . . ?
C7 C1 C6 C5 59.47(18) . . . . ?
C4 C5 C6 C1 59.00(18) . . . . ?
C12 C5 C6 C1 -179.03(15) . . . . ?
C10 C5 C6 C1 -58.94(19) . . . . ?
N1 C1 C7 C8 -175.10(14) . . . . ?
C2 C1 C7 C8 58.83(19) . . . . ?
C6 C1 C7 C8 -60.13(19) . . . . ?
C1 C7 C8 C9 -59.4(2) . . . . ?
C1 C7 C8 C10 61.1(2) . . . . ?
C7 C8 C9 C3 60.1(2) . . . . ?
C10 C8 C9 C3 -59.8(2) . . . . ?
C11 C3 C9 C8 -179.29(17) . . . . ?
C4 C3 C9 C8 58.74(19) . . . . ?
C2 C3 C9 C8 -59.1(2) . . . . ?
C9 C8 C10 C5 59.4(2) . . . . ?
C7 C8 C10 C5 -61.0(2) . . . . ?
C4 C5 C10 C8 -58.28(19) . . . . ?
C12 C5 C10 C8 179.17(16) . . . . ?
C6 C5 C10 C8 59.3(2) . . . . ?
O2 S1 C13 C14 166.43(12) . . . . ?
O1 S1 C13 C14 39.81(15) . . . . ?
N1 S1 C13 C14 -73.81(14) . . . . ?
O2 S1 C13 C18 -8.91(16) . . . . ?
O1 S1 C13 C18 -135.53(14) . . . . ?
N1 S1 C13 C18 110.85(14) . . . . ?
C18 C13 C14 C15 0.8(2) . . . . ?
S1 C13 C14 C15 -174.52(13) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C14 C15 C16 C17 -1.2(2) . . . . ?
C14 C15 C16 N2 176.84(15) . . . . ?
C19 N2 C16 C15 18.2(3) . . . . ?
C19 N2 C16 C17 -163.66(16) . . . . ?
C15 C16 C17 C18 1.4(3) . . . . ?
N2 C16 C17 C18 -176.80(16) . . . . ?
C16 C17 C18 C13 -0.4(3) . . . . ?
C14 C13 C18 C17 -0.7(3) . . . . ?
S1 C13 C18 C17 174.61(13) . . . . ?
C16 N2 C19 O3 -0.9(3) . . . . ?
C16 N2 C19 C20 178.92(15) . . . . ?
S2 N3 C21 C22 64.58(18) . . . . ?
S2 N3 C21 C26 -177.45(11) . . . . ?
S2 N3 C21 C27 -59.95(18) . . . . ?
N3 C21 C22 C23 175.37(16) . . . . ?
C26 C21 C22 C23 59.8(2) . . . . ?
C27 C21 C22 C23 -59.0(2) . . . . ?
C21 C22 C23 C31 -179.7(2) . . . . ?
C21 C22 C23 C29 58.3(2) . . . . ?
C21 C22 C23 C24 -58.9(2) . . . . ?
C31 C23 C24 C25 178.72(18) . . . . ?
C29 C23 C24 C25 -58.9(2) . . . . ?
C22 C23 C24 C25 58.4(2) . . . . ?
C23 C24 C25 C30 59.6(2) . . . . ?
C23 C24 C25 C32 -178.72(16) . . . . ?
C23 C24 C25 C26 -58.4(2) . . . . ?
N3 C21 C26 C25 179.17(13) . . . . ?
C22 C21 C26 C25 -60.09(18) . . . . ?
C27 C21 C26 C25 59.50(18) . . . . ?
C30 C25 C26 C21 -59.10(19) . . . . ?
C24 C25 C26 C21 59.06(19) . . . . ?
C32 C25 C26 C21 -179.54(15) . . . . ?
N3 C21 C27 C28 -175.11(16) . . . . ?
C22 C21 C27 C28 58.8(2) . . . . ?
C26 C21 C27 C28 -60.0(2) . . . . ?
C21 C27 C28 C29 -59.7(2) . . . . ?
C21 C27 C28 C30 61.7(2) . . . . ?
C30 C28 C29 C23 -60.0(2) . . . . ?
C27 C28 C29 C23 60.7(2) . . . . ?
C31 C23 C29 C28 -179.83(19) . . . . ?
C24 C23 C29 C28 58.4(2) . . . . ?
C22 C23 C29 C28 -59.1(2) . . . . ?
C24 C25 C30 C28 -58.5(2) . . . . ?
C32 C25 C30 C28 179.28(17) . . . . ?
C26 C25 C30 C28 59.4(2) . . . . ?
C29 C28 C30 C25 59.5(2) . . . . ?
C27 C28 C30 C25 -61.5(2) . . . . ?
O4 S2 C33 C38 -8.63(16) . . . . ?
O5 S2 C33 C38 -135.63(14) . . . . ?
N3 S2 C33 C38 111.28(14) . . . . ?
O4 S2 C33 C34 167.25(13) . . . . ?
O5 S2 C33 C34 40.26(15) . . . . ?
N3 S2 C33 C34 -72.84(14) . . . . ?
C38 C33 C34 C35 1.0(3) . . . . ?
S2 C33 C34 C35 -174.93(13) . . . . ?
C33 C34 C35 C36 0.3(3) . . . . ?
C34 C35 C36 C37 -1.7(2) . . . . ?
C34 C35 C36 N4 176.59(15) . . . . ?
C39 N4 C36 C37 -164.59(16) . . . . ?
C39 N4 C36 C35 17.1(3) . . . . ?
C35 C36 C37 C38 2.0(3) . . . . ?
N4 C36 C37 C38 -176.42(15) . . . . ?
C36 C37 C38 C33 -0.8(3) . . . . ?
C34 C33 C38 C37 -0.7(3) . . . . ?
S2 C33 C38 C37 175.14(13) . . . . ?
C36 N4 C39 O6 1.5(3) . . . . ?
C36 N4 C39 C40 -178.60(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O3 0.88 2.32 2.8979(17) 122.9 3_566
N2 H2C S1 0.88 2.88 3.7210(14) 161.6 4_565
N2 H2C O1 0.88 2.08 2.9440(18) 168.9 4_565
N3 H3A O6 0.88 2.34 2.9189(17) 123.2 3_666
N4 H4C S2 0.88 2.92 3.7569(14) 158.8 4_566
N4 H4C O5 0.88 2.09 2.9608(18) 172.7 4_566
C14 H14A O3 0.95 2.62 3.323(2) 131.2 3_566
C15 H15A O3 0.95 2.29 2.872(2) 118.9 .
C18 H18A O4 0.95 2.63 3.466(2) 147.1 4_566
C35 H35A O6 0.95 2.3 2.883(2) 118.8 .
C38 H38A O2 0.95 2.65 3.478(2) 146.3 4_565

####################################################################### 
# 
# 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_17
_database_code_depnum_ccdc_archive 'CCDC 1962769'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2019-10-31 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;

_audit_creation_date             2017-03-10T15:07:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C19 H24 F3 N O3 S'
_chemical_formula_sum            'C19 H24 F3 N O3 S'
_chemical_formula_weight         403.45

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.5361(6)
_cell_length_b                   11.2474(6)
_cell_length_c                   16.3452(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.077(2)
_cell_angle_gamma                90
_cell_volume                     1907.09(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5832
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      31.58

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.24
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             848

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

_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.649
_exptl_absorpt_correction_T_max  0.7464

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

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.035
_diffrn_reflns_number            20427
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.142
_diffrn_reflns_theta_max         32.565
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.953
_reflns_Friedel_coverage         0
_reflns_number_total             6606
_reflns_number_gt                5130
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   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)+(0.0800P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6606
_refine_ls_number_parameters     340
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1326
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_restrained_S_all      1.08
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.06

#----------------------------------------------------------------------------#
#                   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'
F F 0.0171 0.0103 '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 0.52759(3) 0.40916(3) 0.13062(2) 0.01915(9) Uani 1 1 d . . . . .
F1 F 0.63612(11) 0.12363(11) -0.09538(6) 0.0554(3) Uani 1 1 d . . . . .
F2 F 0.46485(11) 0.11805(11) -0.04232(7) 0.0591(3) Uani 1 1 d . . . . .
F3 F 0.49153(11) 0.25727(10) -0.12685(5) 0.0496(3) Uani 1 1 d . . . . .
C19 C 0.55155(15) 0.19164(14) -0.06594(8) 0.0338(3) Uani 1 1 d . . . . .
O1 O 0.50171(9) 0.43653(8) 0.21181(5) 0.0271(2) Uani 1 1 d . . . . .
O2 O 0.60208(8) 0.49126(8) 0.09113(5) 0.02458(19) Uani 1 1 d . . . . .
O3 O 0.60579(10) 0.26224(9) -0.00352(6) 0.0316(2) Uani 1 1 d . . . . .
N1 N 0.39691(9) 0.38617(9) 0.06694(6) 0.0202(2) Uani 1 1 d . . . . .
C1 C 0.27775(11) 0.32955(10) 0.08539(6) 0.0182(2) Uani 1 1 d . . . . .
C2 C 0.19517(11) 0.29998(11) 0.00080(7) 0.0214(2) Uani 1 1 d . . . . .
C3 C 0.06746(12) 0.24168(12) 0.01170(8) 0.0246(2) Uani 1 1 d . . . . .
C4 C -0.00500(12) 0.32714(12) 0.06079(8) 0.0264(3) Uani 1 1 d . . . . .
C5 C 0.07520(12) 0.35743(12) 0.14590(8) 0.0251(2) Uani 1 1 d . . . . .
C6 C 0.20259(12) 0.41475(11) 0.13261(8) 0.0225(2) Uani 1 1 d . . . . .
C7 C 0.30741(12) 0.21416(11) 0.13533(8) 0.0222(2) Uani 1 1 d . . . . .
C8 C 0.18072(12) 0.15632(11) 0.14796(8) 0.0254(2) Uani 1 1 d . . . . .
C9 C 0.09836(13) 0.12770(12) 0.06340(9) 0.0277(3) Uani 1 1 d . . . . .
C10 C 0.10687(14) 0.24196(13) 0.19550(8) 0.0280(3) Uani 1 1 d . . . . .
C11 C -0.01342(15) 0.21260(16) -0.07277(9) 0.0353(3) Uani 1 1 d . . . . .
C12 C 0.00073(17) 0.44264(16) 0.19310(11) 0.0383(3) Uani 1 1 d . . . . .
C13 C 0.61619(11) 0.27404(11) 0.14255(7) 0.0206(2) Uani 1 1 d . . . . .
C14 C 0.64641(12) 0.21230(12) 0.07522(7) 0.0241(2) Uani 1 1 d . . . . .
C15 C 0.71981(14) 0.10956(13) 0.08659(9) 0.0326(3) Uani 1 1 d . . . . .
C16 C 0.76374(14) 0.06847(14) 0.16634(10) 0.0345(3) Uani 1 1 d . . . . .
C17 C 0.73622(13) 0.12961(14) 0.23435(9) 0.0327(3) Uani 1 1 d . . . . .
C18 C 0.66180(13) 0.23236(12) 0.22241(8) 0.0275(3) Uani 1 1 d . . . . .
H1 H 0.3956(16) 0.4162(14) 0.0182(11) 0.028(4) Uiso 1 1 d . . . . .
H2 H 0.2409(18) 0.2454(17) -0.0269(11) 0.041(5) Uiso 1 1 d . . . . .
H3 H 0.1769(16) 0.3758(16) -0.0329(10) 0.031(4) Uiso 1 1 d . . . . .
H4 H -0.0900(17) 0.2869(16) 0.0687(10) 0.036(4) Uiso 1 1 d . . . . .
H5 H -0.0282(17) 0.4019(15) 0.0243(11) 0.035(5) Uiso 1 1 d . . . . .
H6 H 0.1848(15) 0.4881(14) 0.0993(10) 0.023(4) Uiso 1 1 d . . . . .
H7 H 0.2541(17) 0.4370(14) 0.1855(11) 0.032(4) Uiso 1 1 d . . . . .
H8 H 0.3529(15) 0.1595(15) 0.1055(10) 0.028(4) Uiso 1 1 d . . . . .
H9 H 0.3599(15) 0.2316(15) 0.1897(10) 0.028(4) Uiso 1 1 d . . . . .
H10 H 0.1978(16) 0.0806(14) 0.1802(11) 0.028(4) Uiso 1 1 d . . . . .
H11 H 0.1397(18) 0.0746(16) 0.0302(12) 0.039(5) Uiso 1 1 d . . . . .
H12 H 0.0155(18) 0.0853(15) 0.0712(11) 0.037(5) Uiso 1 1 d . . . . .
H13 H 0.0286(19) 0.2070(17) 0.2039(11) 0.043(5) Uiso 1 1 d . . . . .
H14 H 0.1584(16) 0.2577(16) 0.2494(11) 0.034(4) Uiso 1 1 d . . . . .
H15 H -0.096(2) 0.178(2) -0.0679(13) 0.058(6) Uiso 1 1 d . . . . .
H18 H -0.024(2) 0.513(2) 0.1625(13) 0.048(5) Uiso 1 1 d . . . . .
H16 H 0.0317(16) 0.1568(17) -0.1059(11) 0.039(5) Uiso 1 1 d . . . . .
H17 H -0.0285(18) 0.2831(17) -0.1066(12) 0.042(5) Uiso 1 1 d . . . . .
H19 H -0.076(2) 0.4099(19) 0.2037(14) 0.062(7) Uiso 1 1 d . . . . .
H24 H 0.6351(18) 0.2749(17) 0.2673(12) 0.044(5) Uiso 1 1 d . . . . .
H21 H 0.743(2) 0.0630(18) 0.0390(14) 0.055(6) Uiso 1 1 d . . . . .
H20 H 0.0499(19) 0.4661(18) 0.2471(13) 0.046(5) Uiso 1 1 d . . . . .
H22 H 0.8166(18) -0.0044(18) 0.1715(12) 0.045(5) Uiso 1 1 d . . . . .
H23 H 0.7738(19) 0.1015(16) 0.2899(11) 0.041(5) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 O1 1.4342(9) . ?
S1 O2 1.4362(9) . ?
S1 N1 1.5951(10) . ?
S1 C13 1.7763(13) . ?
F1 C19 1.3269(16) . ?
F2 C19 1.339(2) . ?
F3 C19 1.3099(17) . ?
C19 O3 1.3394(17) . ?
O3 C14 1.4009(14) . ?
N1 C1 1.4851(14) . ?
N1 H1 0.863(17) . ?
C1 C6 1.5346(16) . ?
C1 C2 1.5356(15) . ?
C1 C7 1.5359(16) . ?
C2 C3 1.5349(17) . ?
C2 H2 0.943(19) . ?
C2 H3 1.015(17) . ?
C3 C11 1.5256(18) . ?
C3 C4 1.5378(18) . ?
C3 C9 1.5386(19) . ?
C4 C5 1.5344(18) . ?
C4 H4 1.031(17) . ?
C4 H5 1.036(18) . ?
C5 C12 1.5301(19) . ?
C5 C10 1.5364(19) . ?
C5 C6 1.5382(17) . ?
C6 H6 0.988(16) . ?
C6 H7 0.970(18) . ?
C7 C8 1.5311(17) . ?
C7 H8 0.963(16) . ?
C7 H9 0.981(16) . ?
C8 C9 1.5322(19) . ?
C8 C10 1.5325(18) . ?
C8 H10 1.001(16) . ?
C9 H11 0.961(19) . ?
C9 H12 1.022(18) . ?
C10 H13 0.95(2) . ?
C10 H14 0.967(18) . ?
C11 H15 0.96(2) . ?
C11 H16 1.002(18) . ?
C11 H17 0.96(2) . ?
C12 H18 0.95(2) . ?
C12 H19 0.93(2) . ?
C12 H20 0.98(2) . ?
C13 C14 1.3847(17) . ?
C13 C18 1.3911(16) . ?
C14 C15 1.3848(19) . ?
C15 C16 1.384(2) . ?
C15 H21 1.00(2) . ?
C16 C17 1.380(2) . ?
C16 H22 0.99(2) . ?
C17 C18 1.391(2) . ?
C17 H23 0.978(18) . ?
C18 H24 0.96(2) . ?

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 119.03(6) . . ?
O1 S1 N1 110.88(6) . . ?
O2 S1 N1 106.75(5) . . ?
O1 S1 C13 105.27(5) . . ?
O2 S1 C13 106.35(5) . . ?
N1 S1 C13 108.06(6) . . ?
F3 C19 F1 108.34(11) . . ?
F3 C19 F2 107.74(13) . . ?
F1 C19 F2 106.47(14) . . ?
F3 C19 O3 109.26(13) . . ?
F1 C19 O3 113.20(12) . . ?
F2 C19 O3 111.63(11) . . ?
C19 O3 C14 118.89(11) . . ?
C1 N1 S1 126.94(7) . . ?
C1 N1 H1 118.5(11) . . ?
S1 N1 H1 114.3(11) . . ?
N1 C1 C6 111.30(9) . . ?
N1 C1 C2 106.02(8) . . ?
C6 C1 C2 109.10(10) . . ?
N1 C1 C7 111.69(9) . . ?
C6 C1 C7 109.59(9) . . ?
C2 C1 C7 109.03(10) . . ?
C3 C2 C1 110.98(9) . . ?
C3 C2 H2 108.1(11) . . ?
C1 C2 H2 108.4(11) . . ?
C3 C2 H3 109.6(9) . . ?
C1 C2 H3 109.3(10) . . ?
H2 C2 H3 110.5(14) . . ?
C11 C3 C2 110.41(10) . . ?
C11 C3 C4 110.88(12) . . ?
C2 C3 C4 108.59(10) . . ?
C11 C3 C9 110.45(11) . . ?
C2 C3 C9 108.31(10) . . ?
C4 C3 C9 108.11(10) . . ?
C5 C4 C3 111.53(10) . . ?
C5 C4 H4 109.6(9) . . ?
C3 C4 H4 108.2(10) . . ?
C5 C4 H5 112.3(10) . . ?
C3 C4 H5 107.2(10) . . ?
H4 C4 H5 107.9(14) . . ?
C12 C5 C4 110.28(12) . . ?
C12 C5 C10 110.28(11) . . ?
C4 C5 C10 108.96(11) . . ?
C12 C5 C6 110.23(11) . . ?
C4 C5 C6 108.71(10) . . ?
C10 C5 C6 108.33(10) . . ?
C1 C6 C5 110.43(10) . . ?
C1 C6 H6 108.0(9) . . ?
C5 C6 H6 110.0(9) . . ?
C1 C6 H7 110.6(10) . . ?
C5 C6 H7 110.4(10) . . ?
H6 C6 H7 107.4(13) . . ?
C8 C7 C1 109.24(10) . . ?
C8 C7 H8 108.6(10) . . ?
C1 C7 H8 110.1(10) . . ?
C8 C7 H9 109.2(9) . . ?
C1 C7 H9 110.0(10) . . ?
H8 C7 H9 109.5(13) . . ?
C7 C8 C9 109.70(10) . . ?
C7 C8 C10 109.47(11) . . ?
C9 C8 C10 109.38(11) . . ?
C7 C8 H10 110.6(10) . . ?
C9 C8 H10 108.5(10) . . ?
C10 C8 H10 109.2(10) . . ?
C8 C9 C3 110.63(10) . . ?
C8 C9 H11 113.5(11) . . ?
C3 C9 H11 106.3(11) . . ?
C8 C9 H12 110.3(10) . . ?
C3 C9 H12 110.7(10) . . ?
H11 C9 H12 105.1(15) . . ?
C8 C10 C5 110.27(10) . . ?
C8 C10 H13 110.2(11) . . ?
C5 C10 H13 108.3(11) . . ?
C8 C10 H14 108.8(10) . . ?
C5 C10 H14 111.2(11) . . ?
H13 C10 H14 108.0(14) . . ?
C3 C11 H15 112.2(12) . . ?
C3 C11 H16 112.4(10) . . ?
H15 C11 H16 108.2(17) . . ?
C3 C11 H17 110.7(12) . . ?
H15 C11 H17 108.5(17) . . ?
H16 C11 H17 104.5(14) . . ?
C5 C12 H18 111.9(12) . . ?
C5 C12 H19 112.6(14) . . ?
H18 C12 H19 105.2(18) . . ?
C5 C12 H20 112.7(12) . . ?
H18 C12 H20 107.7(17) . . ?
H19 C12 H20 106.2(18) . . ?
C14 C13 C18 119.15(12) . . ?
C14 C13 S1 122.09(9) . . ?
C18 C13 S1 118.69(10) . . ?
C13 C14 C15 120.83(12) . . ?
C13 C14 O3 116.96(11) . . ?
C15 C14 O3 122.11(12) . . ?
C16 C15 C14 119.46(14) . . ?
C16 C15 H21 117.9(12) . . ?
C14 C15 H21 122.6(12) . . ?
C17 C16 C15 120.62(13) . . ?
C17 C16 H22 122.7(11) . . ?
C15 C16 H22 116.7(11) . . ?
C16 C17 C18 119.58(12) . . ?
C16 C17 H23 118.6(11) . . ?
C18 C17 H23 121.7(11) . . ?
C17 C18 C13 120.35(13) . . ?
C17 C18 H24 122.8(11) . . ?
C13 C18 H24 116.8(12) . . ?

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
F3 C19 O3 C14 163.92(12) . . . . ?
F1 C19 O3 C14 -75.26(16) . . . . ?
F2 C19 O3 C14 44.87(17) . . . . ?
O1 S1 N1 C1 -34.64(12) . . . . ?
O2 S1 N1 C1 -165.72(10) . . . . ?
C13 S1 N1 C1 80.25(11) . . . . ?
S1 N1 C1 C6 75.59(12) . . . . ?
S1 N1 C1 C2 -165.90(9) . . . . ?
S1 N1 C1 C7 -47.26(13) . . . . ?
N1 C1 C2 C3 -179.40(10) . . . . ?
C6 C1 C2 C3 -59.43(13) . . . . ?
C7 C1 C2 C3 60.22(13) . . . . ?
C1 C2 C3 C11 -179.89(11) . . . . ?
C1 C2 C3 C4 58.34(13) . . . . ?
C1 C2 C3 C9 -58.84(13) . . . . ?
C11 C3 C4 C5 -179.91(11) . . . . ?
C2 C3 C4 C5 -58.43(13) . . . . ?
C9 C3 C4 C5 58.88(13) . . . . ?
C3 C4 C5 C12 179.90(11) . . . . ?
C3 C4 C5 C10 -58.93(13) . . . . ?
C3 C4 C5 C6 58.94(13) . . . . ?
N1 C1 C6 C5 176.20(9) . . . . ?
C2 C1 C6 C5 59.55(12) . . . . ?
C7 C1 C6 C5 -59.75(12) . . . . ?
C12 C5 C6 C1 179.92(11) . . . . ?
C4 C5 C6 C1 -59.09(13) . . . . ?
C10 C5 C6 C1 59.18(13) . . . . ?
N1 C1 C7 C8 -176.70(9) . . . . ?
C6 C1 C7 C8 59.48(12) . . . . ?
C2 C1 C7 C8 -59.87(12) . . . . ?
C1 C7 C8 C9 60.07(13) . . . . ?
C1 C7 C8 C10 -59.95(13) . . . . ?
C7 C8 C9 C3 -59.95(14) . . . . ?
C10 C8 C9 C3 60.13(13) . . . . ?
C11 C3 C9 C8 179.44(11) . . . . ?
C2 C3 C9 C8 58.41(13) . . . . ?
C4 C3 C9 C8 -59.08(13) . . . . ?
C7 C8 C10 C5 60.77(14) . . . . ?
C9 C8 C10 C5 -59.45(14) . . . . ?
C12 C5 C10 C8 179.65(12) . . . . ?
C4 C5 C10 C8 58.47(14) . . . . ?
C6 C5 C10 C8 -59.64(14) . . . . ?
O1 S1 C13 C14 172.62(10) . . . . ?
O2 S1 C13 C14 -60.20(11) . . . . ?
N1 S1 C13 C14 54.09(11) . . . . ?
O1 S1 C13 C18 -10.55(11) . . . . ?
O2 S1 C13 C18 116.62(10) . . . . ?
N1 S1 C13 C18 -129.08(10) . . . . ?
C18 C13 C14 C15 0.71(19) . . . . ?
S1 C13 C14 C15 177.52(11) . . . . ?
C18 C13 C14 O3 -175.72(11) . . . . ?
S1 C13 C14 O3 1.09(16) . . . . ?
C19 O3 C14 C13 -135.53(13) . . . . ?
C19 O3 C14 C15 48.08(18) . . . . ?
C13 C14 C15 C16 -0.2(2) . . . . ?
O3 C14 C15 C16 176.05(13) . . . . ?
C14 C15 C16 C17 -0.7(2) . . . . ?
C15 C16 C17 C18 1.1(2) . . . . ?
C16 C17 C18 C13 -0.6(2) . . . . ?
C14 C13 C18 C17 -0.33(19) . . . . ?
S1 C13 C18 C17 -177.25(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.863(17) 2.072(18) 2.9300(13) 172.7(15) 3_665
C6 H7 O1 0.970(18) 2.569(17) 3.2001(16) 122.8(13) .
C15 H21 F1 1.00(2) 2.39(2) 2.9549(19) 115.0(15) .

####################################################################### 
# 
# 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_18
_database_code_depnum_ccdc_archive 'CCDC 1962770'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2019-10-31 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;

_audit_creation_date             2017-12-06T23:54:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C18 H24 N2 O3 S'
_chemical_formula_sum            'C18 H24 N2 O3 S'
_chemical_formula_weight         348.45

#----------------------------------------------------------------------------#
#                   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                   12.0138(6)
_cell_length_b                   12.6480(6)
_cell_length_c                   13.5487(7)
_cell_angle_alpha                107.167(2)
_cell_angle_beta                 111.066(2)
_cell_angle_gamma                97.215(2)
_cell_volume                     1772.49(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5128
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      27.29

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             744
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 0.71053   12.016   12.654   13.551  107.127  111.067   97.214   55.92
;

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

_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.6569
_exptl_absorpt_correction_T_max  0.7456

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

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_number            21923
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.209
_diffrn_reflns_theta_max         27.906
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_Friedel_coverage         0
_reflns_number_total             8422
_reflns_number_gt                6021
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_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)+(0.0700P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         8422
_refine_ls_number_parameters     565
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.075
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1264
_refine_ls_wR_factor_gt          0.1128
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.055

#----------------------------------------------------------------------------#
#                   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 0.48714(4) 0.08732(4) 0.16155(4) 0.01874(12) Uani 1 1 d . . . . .
S2 S 0.17007(4) 0.93239(4) 0.25581(4) 0.02039(12) Uani 1 1 d . . . . .
O1 O 0.44711(12) 0.16298(11) 0.23618(11) 0.0235(3) Uani 1 1 d . . . . .
O2 O 0.39575(12) -0.00142(11) 0.05870(11) 0.0233(3) Uani 1 1 d . . . . .
O3 O 0.93205(13) -0.18990(13) 0.33202(12) 0.0304(3) Uani 1 1 d . . . . .
O4 O 0.29026(12) 0.96330(12) 0.25863(12) 0.0267(3) Uani 1 1 d . . . . .
O5 O 0.12979(13) 1.01624(12) 0.32400(11) 0.0279(3) Uani 1 1 d . . . . .
O6 O -0.11402(13) 0.72610(12) -0.32860(12) 0.0285(3) Uani 1 1 d . . . . .
N1 N 0.56555(15) 0.16435(15) 0.12181(14) 0.0213(4) Uani 1 1 d . . . . .
N2 N 0.83233(16) -0.11645(15) 0.43998(15) 0.0249(4) Uani 1 1 d . . . . .
N3 N 0.16216(16) 0.82651(14) 0.29865(14) 0.0209(4) Uani 1 1 d . . . . .
N4 N -0.20983(16) 0.79749(14) -0.21554(14) 0.0217(4) Uani 1 1 d . . . . .
C1 C 0.64969(17) 0.28104(16) 0.19097(16) 0.0210(4) Uani 1 1 d . . . . .
C2 C 0.5739(2) 0.3695(2) 0.1924(3) 0.0439(7) Uani 1 1 d . . . . .
H2A H 0.522(2) 0.354(2) 0.110(2) 0.053 Uiso 1 1 d . U . . .
H2B H 0.523(3) 0.355(2) 0.229(2) 0.053 Uiso 1 1 d . U . . .
C3 C 0.6628(2) 0.4906(2) 0.2564(3) 0.0569(9) Uani 1 1 d . . . . .
H3A H 0.616(3) 0.543(3) 0.257(2) 0.068 Uiso 1 1 d . U . . .
C4 C 0.7424(3) 0.5032(2) 0.3770(3) 0.0631(10) Uani 1 1 d . . . . .
H4A H 0.690(3) 0.489(3) 0.416(3) 0.076 Uiso 1 1 d . U . . .
H4B H 0.798(3) 0.581(3) 0.419(3) 0.076 Uiso 1 1 d . U . . .
C5 C 0.8184(3) 0.4168(2) 0.3746(2) 0.0473(7) Uani 1 1 d . . . . .
H5A H 0.868(3) 0.424(2) 0.449(2) 0.057 Uiso 1 1 d . U . . .
C6 C 0.7324(2) 0.2946(2) 0.31184(19) 0.0361(5) Uani 1 1 d . . . . .
H6A H 0.783(2) 0.235(2) 0.303(2) 0.043 Uiso 1 1 d . U . . .
H6B H 0.688(2) 0.279(2) 0.351(2) 0.043 Uiso 1 1 d . U . . .
C7 C 0.7318(2) 0.3001(2) 0.1307(2) 0.0345(5) Uani 1 1 d . . . . .
H7A H 0.682(2) 0.285(2) 0.056(2) 0.041 Uiso 1 1 d . U . . .
H7B H 0.778(2) 0.238(2) 0.1254(19) 0.041 Uiso 1 1 d . U . . .
C8 C 0.8181(2) 0.4220(2) 0.1932(2) 0.0380(6) Uani 1 1 d . . . . .
H8A H 0.866(2) 0.427(2) 0.151(2) 0.046 Uiso 1 1 d . U . . .
C9 C 0.7421(3) 0.5089(2) 0.1944(3) 0.0513(7) Uani 1 1 d . . . . .
H9A H 0.695(3) 0.495(2) 0.112(3) 0.062 Uiso 1 1 d . U . . .
H9B H 0.802(3) 0.586(2) 0.233(2) 0.062 Uiso 1 1 d . U . . .
C10 C 0.8993(2) 0.4357(2) 0.3140(2) 0.0398(6) Uani 1 1 d . . . . .
H10A H 0.950(2) 0.510(2) 0.353(2) 0.048 Uiso 1 1 d . U . . .
H10B H 0.946(2) 0.380(2) 0.308(2) 0.048 Uiso 1 1 d . U . . .
C11 C 0.58278(17) 0.01961(16) 0.24062(16) 0.0205(4) Uani 1 1 d . . . . .
C12 C 0.6437(2) -0.0505(2) 0.19236(18) 0.0311(5) Uani 1 1 d . . . . .
H12A H 0.629(2) -0.0642(19) 0.115(2) 0.037 Uiso 1 1 d . U . . .
C13 C 0.7230(2) -0.1003(2) 0.25447(18) 0.0321(5) Uani 1 1 d . . . . .
H13A H 0.765(2) -0.149(2) 0.2179(19) 0.039 Uiso 1 1 d . U . . .
C14 C 0.74440(18) -0.07826(17) 0.36750(16) 0.0223(4) Uani 1 1 d . . . . .
C15 C 0.67693(19) -0.01334(19) 0.41310(17) 0.0273(5) Uani 1 1 d . . . . .
H15A H 0.690(2) 0.0016(19) 0.4942(19) 0.033 Uiso 1 1 d . U . . .
C16 C 0.59671(19) 0.03542(18) 0.35041(17) 0.0257(4) Uani 1 1 d . . . . .
H16A H 0.550(2) 0.0857(18) 0.3839(18) 0.031 Uiso 1 1 d . U . . .
C17 C 0.92343(18) -0.16271(16) 0.42322(17) 0.0228(4) Uani 1 1 d . . . . .
C18 C 1.01265(19) -0.17933(19) 0.52483(17) 0.0285(5) Uani 1 1 d . . . . .
H18A H 1.089676 -0.184736 0.516466 0.043 Uiso 1 1 calc R U . . .
H18B H 0.976552 -0.250024 0.530477 0.043 Uiso 1 1 calc R U . . .
H18C H 1.029967 -0.114068 0.593844 0.043 Uiso 1 1 calc R U . . .
C19 C 0.20953(17) 0.72478(16) 0.26630(16) 0.0204(4) Uani 1 1 d . . . . .
C20 C 0.1634(2) 0.66455(19) 0.13764(18) 0.0300(5) Uani 1 1 d . . . . .
H20A H 0.196(2) 0.7205(19) 0.1057(19) 0.036 Uiso 1 1 d . U . . .
H20B H 0.073(2) 0.6496(19) 0.1014(19) 0.036 Uiso 1 1 d . U . . .
C21 C 0.2087(2) 0.5556(2) 0.1117(2) 0.0393(6) Uani 1 1 d . . . . .
H21A H 0.179(2) 0.516(2) 0.034(2) 0.047 Uiso 1 1 d . U . . .
C22 C 0.1603(3) 0.4750(2) 0.1598(3) 0.0492(7) Uani 1 1 d . . . . .
H22A H 0.196(2) 0.406(2) 0.152(2) 0.059 Uiso 1 1 d . U . . .
H22B H 0.072(3) 0.453(2) 0.122(2) 0.059 Uiso 1 1 d . U . . .
C23 C 0.2077(3) 0.5339(2) 0.2880(2) 0.0429(6) Uani 1 1 d . . . . .
H23A H 0.174(2) 0.480(2) 0.316(2) 0.052 Uiso 1 1 d . U . . .
C24 C 0.1616(2) 0.6422(2) 0.3137(2) 0.0342(5) Uani 1 1 d . . . . .
H24A H 0.187(2) 0.681(2) 0.392(2) 0.041 Uiso 1 1 d . U . . .
H24B H 0.071(2) 0.622(2) 0.279(2) 0.041 Uiso 1 1 d . U . . .
C25 C 0.35138(19) 0.75648(19) 0.3213(2) 0.0295(5) Uani 1 1 d . . . . .
H25A H 0.381(2) 0.7948(19) 0.402(2) 0.035 Uiso 1 1 d . U . . .
H25B H 0.387(2) 0.817(2) 0.2967(19) 0.035 Uiso 1 1 d . U . . .
C26 C 0.3966(2) 0.6475(2) 0.2951(2) 0.0354(5) Uani 1 1 d . . . . .
H26A H 0.486(2) 0.669(2) 0.332(2) 0.043 Uiso 1 1 d . U . . .
C27 C 0.3497(2) 0.5885(2) 0.1666(2) 0.0407(6) Uani 1 1 d . . . . .
H27A H 0.377(2) 0.519(2) 0.148(2) 0.049 Uiso 1 1 d . U . . .
H27B H 0.386(2) 0.644(2) 0.140(2) 0.049 Uiso 1 1 d . U . . .
C28 C 0.3484(2) 0.5665(2) 0.3432(2) 0.0425(6) Uani 1 1 d . . . . .
H28A H 0.373(2) 0.499(2) 0.328(2) 0.051 Uiso 1 1 d . U . . .
H28B H 0.377(2) 0.602(2) 0.423(2) 0.051 Uiso 1 1 d . U . . .
C29 C 0.06042(17) 0.89071(15) 0.11447(15) 0.0187(4) Uani 1 1 d . . . . .
C30 C 0.09672(19) 0.88278(16) 0.02705(16) 0.0211(4) Uani 1 1 d . . . . .
H30A H 0.181(2) 0.9008(17) 0.0421(17) 0.025 Uiso 1 1 d . U . . .
C31 C 0.00903(18) 0.85050(17) -0.08353(16) 0.0213(4) Uani 1 1 d . . . . .
H31A H 0.0327(19) 0.8539(17) -0.1453(17) 0.026 Uiso 1 1 d . U . . .
C32 C -0.11603(17) 0.82685(15) -0.10646(16) 0.0194(4) Uani 1 1 d . . . . .
C33 C -0.15168(19) 0.83630(18) -0.01746(17) 0.0239(4) Uani 1 1 d . . . . .
H33A H -0.234(2) 0.8217(18) -0.0337(18) 0.029 Uiso 1 1 d . U . . .
C34 C -0.06455(19) 0.86741(18) 0.09179(17) 0.0253(4) Uani 1 1 d . . . . .
H34A H -0.0857(19) 0.8749(18) 0.1545(18) 0.03 Uiso 1 1 d . U . . .
C35 C -0.20503(18) 0.75184(16) -0.31813(16) 0.0220(4) Uani 1 1 d . . . . .
C36 C -0.3239(2) 0.73144(19) -0.41863(17) 0.0306(5) Uani 1 1 d . . . . .
H36A H -0.306714 0.728253 -0.484742 0.046 Uiso 1 1 calc R U . . .
H36B H -0.362512 0.794084 -0.40094 0.046 Uiso 1 1 calc R U . . .
H36C H -0.379957 0.65869 -0.435693 0.046 Uiso 1 1 calc R U . . .
H1 H 0.577(2) 0.126(2) 0.0778(19) 0.028(7) Uiso 1 1 d . . . . .
H2 H 0.842(2) -0.093(2) 0.507(2) 0.039(7) Uiso 1 1 d . . . . .
H3 H 0.100(2) 0.812(2) 0.306(2) 0.046(8) Uiso 1 1 d . . . . .
H4 H -0.275(2) 0.8138(19) -0.2166(19) 0.033(6) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 O1 1.4365(13) . ?
S1 O2 1.4402(14) . ?
S1 N1 1.6032(17) . ?
S1 C11 1.7620(19) . ?
S2 O4 1.4314(14) . ?
S2 O5 1.4437(14) . ?
S2 N3 1.6143(17) . ?
S2 C29 1.7596(19) . ?
O3 C17 1.227(2) . ?
O6 C35 1.223(2) . ?
N1 C1 1.485(2) . ?
N1 H1 0.71(2) . ?
N2 C17 1.361(2) . ?
N2 C14 1.406(2) . ?
N2 H2 0.82(2) . ?
N3 C19 1.484(2) . ?
N3 H3 0.80(3) . ?
N4 C35 1.364(2) . ?
N4 C32 1.402(2) . ?
N4 H4 0.84(2) . ?
C1 C6 1.523(3) . ?
C1 C7 1.527(3) . ?
C1 C2 1.529(3) . ?
C2 C3 1.542(3) . ?
C2 H2A 1.01(3) . ?
C2 H2B 0.94(3) . ?
C3 C4 1.515(5) . ?
C3 C9 1.517(4) . ?
C3 H3A 0.92(3) . ?
C4 C5 1.510(4) . ?
C4 H4A 0.99(3) . ?
C4 H4B 0.98(3) . ?
C5 C10 1.519(4) . ?
C5 C6 1.540(3) . ?
C5 H5A 0.94(3) . ?
C6 H6A 1.03(2) . ?
C6 H6B 0.91(2) . ?
C7 C8 1.539(3) . ?
C7 H7A 0.92(2) . ?
C7 H7B 1.01(2) . ?
C8 C9 1.514(4) . ?
C8 C10 1.518(4) . ?
C8 H8A 0.96(3) . ?
C9 H9A 1.00(3) . ?
C9 H9B 1.00(3) . ?
C10 H10A 0.93(3) . ?
C10 H10B 0.95(3) . ?
C11 C12 1.384(3) . ?
C11 C16 1.385(3) . ?
C12 C13 1.378(3) . ?
C12 H12A 0.95(2) . ?
C13 C14 1.391(3) . ?
C13 H13A 0.98(2) . ?
C14 C15 1.393(3) . ?
C15 C16 1.379(3) . ?
C15 H15A 1.01(2) . ?
C16 H16A 1.02(2) . ?
C17 C18 1.502(3) . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C19 C20 1.530(3) . ?
C19 C24 1.531(3) . ?
C19 C25 1.536(3) . ?
C20 C21 1.536(3) . ?
C20 H20A 1.04(2) . ?
C20 H20B 0.98(2) . ?
C21 C22 1.523(4) . ?
C21 C27 1.527(4) . ?
C21 H21A 0.92(2) . ?
C22 C23 1.521(4) . ?
C22 H22A 1.02(3) . ?
C22 H22B 0.96(3) . ?
C23 C28 1.524(4) . ?
C23 C24 1.533(3) . ?
C23 H23A 0.98(3) . ?
C24 H24A 0.94(2) . ?
C24 H24B 0.98(2) . ?
C25 C26 1.537(3) . ?
C25 H25A 0.96(2) . ?
C25 H25B 1.02(2) . ?
C26 C27 1.525(3) . ?
C26 C28 1.525(4) . ?
C26 H26A 0.97(2) . ?
C27 H27A 0.97(3) . ?
C27 H27B 1.00(3) . ?
C28 H28A 0.93(3) . ?
C28 H28B 0.95(3) . ?
C29 C30 1.384(3) . ?
C29 C34 1.393(3) . ?
C30 C31 1.385(3) . ?
C30 H30A 0.95(2) . ?
C31 C32 1.393(3) . ?
C31 H31A 0.99(2) . ?
C32 C33 1.397(3) . ?
C33 C34 1.371(3) . ?
C33 H33A 0.91(2) . ?
C34 H34A 0.95(2) . ?
C35 C36 1.504(3) . ?
C36 H36A 0.98 . ?
C36 H36B 0.98 . ?
C36 H36C 0.98 . ?

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 119.03(8) . . ?
O1 S1 N1 107.53(9) . . ?
O2 S1 N1 105.80(8) . . ?
O1 S1 C11 107.43(8) . . ?
O2 S1 C11 107.15(8) . . ?
N1 S1 C11 109.71(9) . . ?
O4 S2 O5 119.22(9) . . ?
O4 S2 N3 108.75(9) . . ?
O5 S2 N3 104.68(9) . . ?
O4 S2 C29 108.10(9) . . ?
O5 S2 C29 105.99(8) . . ?
N3 S2 C29 109.87(9) . . ?
C1 N1 S1 126.93(13) . . ?
C1 N1 H1 120.2(19) . . ?
S1 N1 H1 107.4(19) . . ?
C17 N2 C14 128.72(17) . . ?
C17 N2 H2 113.8(17) . . ?
C14 N2 H2 115.4(17) . . ?
C19 N3 S2 126.01(13) . . ?
C19 N3 H3 113.6(19) . . ?
S2 N3 H3 111.4(18) . . ?
C35 N4 C32 128.41(17) . . ?
C35 N4 H4 116.9(15) . . ?
C32 N4 H4 114.6(15) . . ?
N1 C1 C6 113.33(16) . . ?
N1 C1 C7 106.06(15) . . ?
C6 C1 C7 108.32(18) . . ?
N1 C1 C2 109.47(16) . . ?
C6 C1 C2 110.4(2) . . ?
C7 C1 C2 109.04(19) . . ?
C1 C2 C3 108.92(19) . . ?
C1 C2 H2A 104.8(15) . . ?
C3 C2 H2A 113.2(16) . . ?
C1 C2 H2B 107.5(17) . . ?
C3 C2 H2B 111.4(17) . . ?
H2A C2 H2B 111(2) . . ?
C4 C3 C9 110.7(2) . . ?
C4 C3 C2 109.3(3) . . ?
C9 C3 C2 109.4(2) . . ?
C4 C3 H3A 110.3(18) . . ?
C9 C3 H3A 108.9(19) . . ?
C2 C3 H3A 108.3(19) . . ?
C5 C4 C3 109.5(2) . . ?
C5 C4 H4A 108.5(18) . . ?
C3 C4 H4A 110.2(18) . . ?
C5 C4 H4B 109.0(18) . . ?
C3 C4 H4B 109.7(19) . . ?
H4A C4 H4B 110(2) . . ?
C4 C5 C10 109.8(2) . . ?
C4 C5 C6 109.8(2) . . ?
C10 C5 C6 109.4(2) . . ?
C4 C5 H5A 109.7(17) . . ?
C10 C5 H5A 109.9(16) . . ?
C6 C5 H5A 108.2(17) . . ?
C1 C6 C5 109.11(19) . . ?
C1 C6 H6A 105.1(13) . . ?
C5 C6 H6A 110.7(14) . . ?
C1 C6 H6B 112.6(16) . . ?
C5 C6 H6B 110.9(16) . . ?
H6A C6 H6B 108(2) . . ?
C1 C7 C8 109.82(18) . . ?
C1 C7 H7A 108.6(15) . . ?
C8 C7 H7A 113.4(15) . . ?
C1 C7 H7B 108.8(13) . . ?
C8 C7 H7B 113.2(14) . . ?
H7A C7 H7B 102.7(19) . . ?
C9 C8 C10 110.1(2) . . ?
C9 C8 C7 109.7(2) . . ?
C10 C8 C7 108.9(2) . . ?
C9 C8 H8A 112.3(15) . . ?
C10 C8 H8A 111.2(15) . . ?
C7 C8 H8A 104.5(15) . . ?
C8 C9 C3 108.9(2) . . ?
C8 C9 H9A 103.9(16) . . ?
C3 C9 H9A 114.8(16) . . ?
C8 C9 H9B 106.1(17) . . ?
C3 C9 H9B 112.9(16) . . ?
H9A C9 H9B 109(2) . . ?
C8 C10 C5 109.3(2) . . ?
C8 C10 H10A 109.3(16) . . ?
C5 C10 H10A 108.0(15) . . ?
C8 C10 H10B 106.2(15) . . ?
C5 C10 H10B 112.0(15) . . ?
H10A C10 H10B 112(2) . . ?
C12 C11 C16 119.75(18) . . ?
C12 C11 S1 119.76(15) . . ?
C16 C11 S1 120.48(14) . . ?
C13 C12 C11 120.61(18) . . ?
C13 C12 H12A 120.7(14) . . ?
C11 C12 H12A 118.7(14) . . ?
C12 C13 C14 119.96(19) . . ?
C12 C13 H13A 118.5(14) . . ?
C14 C13 H13A 121.5(14) . . ?
C13 C14 C15 118.88(19) . . ?
C13 C14 N2 123.66(18) . . ?
C15 C14 N2 117.45(17) . . ?
C16 C15 C14 120.86(18) . . ?
C16 C15 H15A 119.6(13) . . ?
C14 C15 H15A 119.4(13) . . ?
C15 C16 C11 119.65(18) . . ?
C15 C16 H16A 121.6(12) . . ?
C11 C16 H16A 118.7(12) . . ?
O3 C17 N2 122.93(18) . . ?
O3 C17 C18 122.15(18) . . ?
N2 C17 C18 114.91(17) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 C20 113.41(16) . . ?
N3 C19 C24 105.37(16) . . ?
C20 C19 C24 108.88(18) . . ?
N3 C19 C25 111.22(16) . . ?
C20 C19 C25 109.10(17) . . ?
C24 C19 C25 108.70(17) . . ?
C19 C20 C21 109.87(18) . . ?
C19 C20 H20A 108.8(13) . . ?
C21 C20 H20A 110.5(13) . . ?
C19 C20 H20B 109.5(13) . . ?
C21 C20 H20B 113.1(13) . . ?
H20A C20 H20B 104.9(19) . . ?
C22 C21 C27 109.5(2) . . ?
C22 C21 C20 109.7(2) . . ?
C27 C21 C20 109.1(2) . . ?
C22 C21 H21A 106.9(16) . . ?
C27 C21 H21A 110.3(16) . . ?
C20 C21 H21A 111.4(16) . . ?
C23 C22 C21 109.6(2) . . ?
C23 C22 H22A 103.1(15) . . ?
C21 C22 H22A 111.6(15) . . ?
C23 C22 H22B 112.4(17) . . ?
C21 C22 H22B 108.0(17) . . ?
H22A C22 H22B 112(2) . . ?
C22 C23 C28 110.1(2) . . ?
C22 C23 C24 109.1(2) . . ?
C28 C23 C24 109.5(2) . . ?
C22 C23 H23A 107.7(15) . . ?
C28 C23 H23A 110.7(16) . . ?
C24 C23 H23A 109.7(15) . . ?
C19 C24 C23 110.26(18) . . ?
C19 C24 H24A 108.3(15) . . ?
C23 C24 H24A 112.6(15) . . ?
C19 C24 H24B 109.1(14) . . ?
C23 C24 H24B 109.9(14) . . ?
H24A C24 H24B 107(2) . . ?
C19 C25 C26 109.66(18) . . ?
C19 C25 H25A 109.5(13) . . ?
C26 C25 H25A 110.1(14) . . ?
C19 C25 H25B 110.9(13) . . ?
C26 C25 H25B 113.1(13) . . ?
H25A C25 H25B 103.4(18) . . ?
C27 C26 C28 109.7(2) . . ?
C27 C26 C25 109.32(19) . . ?
C28 C26 C25 109.69(19) . . ?
C27 C26 H26A 111.1(14) . . ?
C28 C26 H26A 108.4(14) . . ?
C25 C26 H26A 108.6(14) . . ?
C26 C27 C21 109.67(19) . . ?
C26 C27 H27A 110.7(15) . . ?
C21 C27 H27A 108.4(15) . . ?
C26 C27 H27B 106.4(14) . . ?
C21 C27 H27B 112.7(15) . . ?
H27A C27 H27B 109(2) . . ?
C23 C28 C26 109.1(2) . . ?
C23 C28 H28A 107.4(16) . . ?
C26 C28 H28A 112.2(16) . . ?
C23 C28 H28B 109.4(16) . . ?
C26 C28 H28B 110.4(16) . . ?
H28A C28 H28B 108(2) . . ?
C30 C29 C34 120.12(18) . . ?
C30 C29 S2 121.08(15) . . ?
C34 C29 S2 118.80(14) . . ?
C29 C30 C31 120.22(18) . . ?
C29 C30 H30A 120.6(13) . . ?
C31 C30 H30A 119.1(13) . . ?
C30 C31 C32 119.76(17) . . ?
C30 C31 H31A 121.4(12) . . ?
C32 C31 H31A 118.3(12) . . ?
C31 C32 C33 119.58(18) . . ?
C31 C32 N4 122.96(16) . . ?
C33 C32 N4 117.42(17) . . ?
C34 C33 C32 120.46(18) . . ?
C34 C33 H33A 121.0(13) . . ?
C32 C33 H33A 118.5(13) . . ?
C33 C34 C29 119.86(18) . . ?
C33 C34 H34A 122.6(13) . . ?
C29 C34 H34A 117.6(13) . . ?
O6 C35 N4 123.52(19) . . ?
O6 C35 C36 122.44(18) . . ?
N4 C35 C36 113.99(17) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 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
O1 S1 N1 C1 35.93(18) . . . . ?
O2 S1 N1 C1 164.12(15) . . . . ?
C11 S1 N1 C1 -80.61(18) . . . . ?
O4 S2 N3 C19 -42.80(18) . . . . ?
O5 S2 N3 C19 -171.25(15) . . . . ?
C29 S2 N3 C19 75.33(17) . . . . ?
S1 N1 C1 C6 43.2(2) . . . . ?
S1 N1 C1 C7 161.86(16) . . . . ?
S1 N1 C1 C2 -80.6(2) . . . . ?
N1 C1 C2 C3 -175.6(2) . . . . ?
C6 C1 C2 C3 59.0(3) . . . . ?
C7 C1 C2 C3 -60.0(3) . . . . ?
C1 C2 C3 C4 -59.9(3) . . . . ?
C1 C2 C3 C9 61.5(3) . . . . ?
C9 C3 C4 C5 -59.1(3) . . . . ?
C2 C3 C4 C5 61.4(3) . . . . ?
C3 C4 C5 C10 59.1(3) . . . . ?
C3 C4 C5 C6 -61.2(3) . . . . ?
N1 C1 C6 C5 178.17(19) . . . . ?
C7 C1 C6 C5 60.8(3) . . . . ?
C2 C1 C6 C5 -58.6(3) . . . . ?
C4 C5 C6 C1 59.4(3) . . . . ?
C10 C5 C6 C1 -61.2(3) . . . . ?
N1 C1 C7 C8 177.05(19) . . . . ?
C6 C1 C7 C8 -61.0(3) . . . . ?
C2 C1 C7 C8 59.3(3) . . . . ?
C1 C7 C8 C9 -59.7(3) . . . . ?
C1 C7 C8 C10 60.8(3) . . . . ?
C10 C8 C9 C3 -59.3(3) . . . . ?
C7 C8 C9 C3 60.5(3) . . . . ?
C4 C3 C9 C8 58.9(3) . . . . ?
C2 C3 C9 C8 -61.6(3) . . . . ?
C9 C8 C10 C5 60.1(3) . . . . ?
C7 C8 C10 C5 -60.2(3) . . . . ?
C4 C5 C10 C8 -59.8(3) . . . . ?
C6 C5 C10 C8 60.7(3) . . . . ?
O1 S1 C11 C12 -174.09(17) . . . . ?
O2 S1 C11 C12 56.92(19) . . . . ?
N1 S1 C11 C12 -57.49(19) . . . . ?
O1 S1 C11 C16 6.37(19) . . . . ?
O2 S1 C11 C16 -122.63(17) . . . . ?
N1 S1 C11 C16 122.96(17) . . . . ?
C16 C11 C12 C13 -3.2(3) . . . . ?
S1 C11 C12 C13 177.21(19) . . . . ?
C11 C12 C13 C14 -1.4(4) . . . . ?
C12 C13 C14 C15 5.2(3) . . . . ?
C12 C13 C14 N2 -173.7(2) . . . . ?
C17 N2 C14 C13 11.6(3) . . . . ?
C17 N2 C14 C15 -167.3(2) . . . . ?
C13 C14 C15 C16 -4.6(3) . . . . ?
N2 C14 C15 C16 174.40(19) . . . . ?
C14 C15 C16 C11 0.1(3) . . . . ?
C12 C11 C16 C15 3.9(3) . . . . ?
S1 C11 C16 C15 -176.59(16) . . . . ?
C14 N2 C17 O3 -8.7(3) . . . . ?
C14 N2 C17 C18 171.87(19) . . . . ?
S2 N3 C19 C20 -52.3(2) . . . . ?
S2 N3 C19 C24 -171.32(16) . . . . ?
S2 N3 C19 C25 71.1(2) . . . . ?
N3 C19 C20 C21 -175.75(18) . . . . ?
C24 C19 C20 C21 -58.8(2) . . . . ?
C25 C19 C20 C21 59.7(2) . . . . ?
C19 C20 C21 C22 59.7(3) . . . . ?
C19 C20 C21 C27 -60.2(3) . . . . ?
C27 C21 C22 C23 59.4(3) . . . . ?
C20 C21 C22 C23 -60.3(3) . . . . ?
C21 C22 C23 C28 -59.9(3) . . . . ?
C21 C22 C23 C24 60.3(3) . . . . ?
N3 C19 C24 C23 -178.59(19) . . . . ?
C20 C19 C24 C23 59.4(3) . . . . ?
C25 C19 C24 C23 -59.3(2) . . . . ?
C22 C23 C24 C19 -60.3(3) . . . . ?
C28 C23 C24 C19 60.2(3) . . . . ?
N3 C19 C25 C26 174.74(17) . . . . ?
C20 C19 C25 C26 -59.4(2) . . . . ?
C24 C19 C25 C26 59.2(2) . . . . ?
C19 C25 C26 C27 59.9(2) . . . . ?
C19 C25 C26 C28 -60.4(3) . . . . ?
C28 C26 C27 C21 59.8(2) . . . . ?
C25 C26 C27 C21 -60.5(3) . . . . ?
C22 C21 C27 C26 -59.5(3) . . . . ?
C20 C21 C27 C26 60.5(3) . . . . ?
C22 C23 C28 C26 59.7(3) . . . . ?
C24 C23 C28 C26 -60.2(3) . . . . ?
C27 C26 C28 C23 -59.6(3) . . . . ?
C25 C26 C28 C23 60.5(3) . . . . ?
O4 S2 C29 C30 5.20(18) . . . . ?
O5 S2 C29 C30 134.09(16) . . . . ?
N3 S2 C29 C30 -113.34(16) . . . . ?
O4 S2 C29 C34 -173.75(15) . . . . ?
O5 S2 C29 C34 -44.86(17) . . . . ?
N3 S2 C29 C34 67.72(17) . . . . ?
C34 C29 C30 C31 -0.7(3) . . . . ?
S2 C29 C30 C31 -179.61(14) . . . . ?
C29 C30 C31 C32 0.5(3) . . . . ?
C30 C31 C32 C33 0.2(3) . . . . ?
C30 C31 C32 N4 177.78(17) . . . . ?
C35 N4 C32 C31 22.9(3) . . . . ?
C35 N4 C32 C33 -159.45(19) . . . . ?
C31 C32 C33 C34 -0.7(3) . . . . ?
N4 C32 C33 C34 -178.43(18) . . . . ?
C32 C33 C34 C29 0.5(3) . . . . ?
C30 C29 C34 C33 0.2(3) . . . . ?
S2 C29 C34 C33 179.11(16) . . . . ?
C32 N4 C35 O6 2.4(3) . . . . ?
C32 N4 C35 C36 -179.82(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12A O2 0.95(2) 2.66(2) 3.531(2) 153.3(18) 2_655
C13 H13A O3 0.98(2) 2.28(2) 2.866(3) 117.7(17) .
C15 H15A S2 1.01(2) 2.98(2) 3.929(2) 157.9(16) 2_666
C30 H30A O2 0.95(2) 2.61(2) 3.526(2) 162.4(17) 1_565
C31 H31A O6 0.99(2) 2.38(2) 2.914(2) 113.4(15) .
N1 H1 O2 0.71(2) 2.21(2) 2.920(2) 177(3) 2_655
N2 H2 O5 0.82(2) 2.09(3) 2.908(2) 174(2) 2_666
N3 H3 O3 0.80(3) 2.16(3) 2.950(2) 169(2) 1_465
N4 H4 O1 0.84(2) 2.05(2) 2.885(2) 173(2) 2_565

####################################################################### 
# 
# 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_23
_database_code_depnum_ccdc_archive 'CCDC 1962777'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2019-10-31 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;

_audit_creation_date             2017-12-07T00:01:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C19 H27 N1 O2 S1'
_chemical_formula_sum            'C19 H27 N O2 S'
_chemical_formula_weight         333.47
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   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                   6.6214(14)
_cell_length_b                   10.2453(17)
_cell_length_c                   13.391(2)
_cell_angle_alpha                91.638(14)
_cell_angle_beta                 96.140(17)
_cell_angle_gamma                100.447(16)
_cell_volume                     887.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      26.19
_cell_measurement_theta_max      28.91
_cell_measurement_wavelength     1.54184

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360

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

_exptl_absorpt_coefficient_mu    1.686
_exptl_absorpt_correction_type   none

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

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_ub_11      -0.099287
_diffrn_orient_matrix_ub_12      -0.06584
_diffrn_orient_matrix_ub_13      0.032904
_diffrn_orient_matrix_ub_21      -0.118092
_diffrn_orient_matrix_ub_22      0.026968
_diffrn_orient_matrix_ub_23      -0.042095
_diffrn_orient_matrix_ub_31      0.007198
_diffrn_orient_matrix_ub_32      -0.069337
_diffrn_orient_matrix_ub_33      -0.052885
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled ω/2τ scans'
_diffrn_standards_number         2
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        1
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-3 -3 2
1 -4 -6

_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_number            6541
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.381
_diffrn_reflns_theta_max         70.045
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             3366
_reflns_number_gt                2510
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_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)+(0.0800P)²+0.1300P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0280(19)
_refine_ls_number_reflns         3366
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.062
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.135
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.043

#----------------------------------------------------------------------------#
#                   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 0.0181 0.0091 '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 0.0311 0.018 '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'

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 0.59667(8) 0.00108(5) 0.17395(4) 0.0538(2) Uani 1 1 d . . . . .
O1 O 0.7830(2) 0.07372(17) 0.22712(13) 0.0704(5) Uani 1 1 d . . . . .
O2 O 0.6141(3) -0.08814(17) 0.09208(11) 0.0723(5) Uani 1 1 d . . . . .
N1 N 0.4528(3) 0.09996(18) 0.12826(14) 0.0572(5) Uani 1 1 d . . . . .
C1 C 0.4302(3) 0.2297(2) 0.17121(14) 0.0490(5) Uani 1 1 d . . . . .
C2 C 0.6069(4) 0.3372(2) 0.1487(3) 0.0794(8) Uani 1 1 d . . . . .
H2A H 0.613666 0.338129 0.076718 0.095 Uiso 1 1 calc R U . . .
H2B H 0.736643 0.318614 0.180535 0.095 Uiso 1 1 calc R U . . .
C3 C 0.5748(5) 0.4727(3) 0.1879(3) 0.0998(11) Uani 1 1 d . . . . .
H3A H 0.690636 0.541431 0.17407 0.12 Uiso 1 1 calc R U . . .
C4 C 0.5638(5) 0.4702(3) 0.2991(3) 0.1124(13) Uani 1 1 d . . . . .
H4A H 0.545919 0.556438 0.324473 0.135 Uiso 1 1 calc R U . . .
H4B H 0.692171 0.451504 0.332459 0.135 Uiso 1 1 calc R U . . .
C5 C 0.3823(5) 0.3632(3) 0.3224(2) 0.0808(8) Uani 1 1 d . . . . .
H5A H 0.375556 0.363063 0.395198 0.097 Uiso 1 1 calc R U . . .
C6 C 0.4128(4) 0.2267(2) 0.28397(16) 0.0658(6) Uani 1 1 d . . . . .
H6A H 0.537366 0.204984 0.319059 0.079 Uiso 1 1 calc R U . . .
H6B H 0.296493 0.159273 0.296611 0.079 Uiso 1 1 calc R U . . .
C7 C 0.2289(3) 0.2617(2) 0.11889(16) 0.0623(6) Uani 1 1 d . . . . .
H7A H 0.234782 0.262406 0.046837 0.075 Uiso 1 1 calc R U . . .
H7B H 0.113343 0.193762 0.131685 0.075 Uiso 1 1 calc R U . . .
C8 C 0.1966(4) 0.3976(3) 0.15799(19) 0.0686(6) Uani 1 1 d . . . . .
H8A H 0.067448 0.417078 0.124181 0.082 Uiso 1 1 calc R U . . .
C9 C 0.3751(5) 0.5032(3) 0.1365(3) 0.0934(10) Uani 1 1 d . . . . .
H9A H 0.355218 0.589493 0.160824 0.112 Uiso 1 1 calc R U . . .
H9B H 0.381508 0.505695 0.064493 0.112 Uiso 1 1 calc R U . . .
C10 C 0.1830(4) 0.3925(3) 0.2699(2) 0.0749(7) Uani 1 1 d . . . . .
H10A H 0.158713 0.476936 0.295906 0.09 Uiso 1 1 calc R U . . .
H10B H 0.068373 0.32386 0.282689 0.09 Uiso 1 1 calc R U . . .
C11 C 0.4523(3) -0.09406(18) 0.26050(13) 0.0460(4) Uani 1 1 d . . . . .
C12 C 0.2494(3) -0.1593(2) 0.22655(15) 0.0531(5) Uani 1 1 d . . . . .
C13 C 0.1364(4) -0.2307(2) 0.29472(18) 0.0649(6) Uani 1 1 d . . . . .
H13A H 0.001831 -0.273392 0.273238 0.078 Uiso 1 1 calc R U . . .
C14 C 0.2150(4) -0.2414(2) 0.39327(17) 0.0674(6) Uani 1 1 d . . . . .
C15 C 0.4140(4) -0.1798(2) 0.42285(15) 0.0623(6) Uani 1 1 d . . . . .
H15A H 0.468954 -0.187951 0.488765 0.075 Uiso 1 1 calc R U . . .
C16 C 0.5387(3) -0.1058(2) 0.35990(14) 0.0509(5) Uani 1 1 d . . . . .
C17 C 0.1455(4) -0.1601(3) 0.12058(18) 0.0741(7) Uani 1 1 d . . . . .
H17A H 0.03134 -0.2335 0.109694 0.111 Uiso 1 1 calc R U . . .
H17B H 0.243 -0.169016 0.073831 0.111 Uiso 1 1 calc R U . . .
H17C H 0.095991 -0.078451 0.11078 0.111 Uiso 1 1 calc R U . . .
C18 C 0.0854(6) -0.3208(3) 0.4646(2) 0.1068(11) Uani 1 1 d . . . . .
H18A H 0.098945 -0.271256 0.527647 0.16 Uiso 1 1 calc R U . . .
H18B H 0.131699 -0.403398 0.475214 0.16 Uiso 1 1 calc R U . . .
H18C H -0.05685 -0.338308 0.436293 0.16 Uiso 1 1 calc R U . . .
C19 C 0.7560(4) -0.0452(3) 0.40436(17) 0.0750(7) Uani 1 1 d . . . . .
H19A H 0.779588 -0.07264 0.471895 0.113 Uiso 1 1 calc R U . . .
H19B H 0.773462 0.04995 0.404959 0.113 Uiso 1 1 calc R U . . .
H19C H 0.853183 -0.07428 0.364496 0.113 Uiso 1 1 calc R U . . .
H1 H 0.420(4) 0.088(2) 0.0715(19) 0.066(7) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 O1 1.4253(17) . ?
S1 O2 1.4348(16) . ?
S1 N1 1.6028(18) . ?
S1 C11 1.7809(19) . ?
N1 C1 1.471(3) . ?
N1 H1 0.77(2) . ?
C1 C2 1.517(3) . ?
C1 C6 1.527(3) . ?
C1 C7 1.533(3) . ?
C2 C3 1.529(4) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 C4 1.499(5) . ?
C3 C9 1.512(5) . ?
C3 H3A 0.98 . ?
C4 C5 1.539(5) . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C5 C10 1.511(4) . ?
C5 C6 1.531(3) . ?
C5 H5A 0.98 . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.532(3) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.509(4) . ?
C8 C10 1.513(3) . ?
C8 H8A 0.98 . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 C12 1.408(3) . ?
C11 C16 1.409(3) . ?
C12 C13 1.384(3) . ?
C12 C17 1.508(3) . ?
C13 C14 1.381(3) . ?
C13 H13A 0.93 . ?
C14 C15 1.365(3) . ?
C14 C18 1.509(3) . ?
C15 C16 1.388(3) . ?
C15 H15A 0.93 . ?
C16 C19 1.511(3) . ?
C17 H17A 0.96 . ?
C17 H17B 0.96 . ?
C17 H17C 0.96 . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C19 H19A 0.96 . ?
C19 H19B 0.96 . ?
C19 H19C 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
O1 S1 O2 117.74(10) . . ?
O1 S1 N1 110.75(10) . . ?
O2 S1 N1 105.97(10) . . ?
O1 S1 C11 108.79(9) . . ?
O2 S1 C11 107.18(10) . . ?
N1 S1 C11 105.72(9) . . ?
C1 N1 S1 127.90(15) . . ?
C1 N1 H1 115.7(19) . . ?
S1 N1 H1 113.6(19) . . ?
N1 C1 C2 110.46(17) . . ?
N1 C1 C6 112.15(16) . . ?
C2 C1 C6 111.1(2) . . ?
N1 C1 C7 106.88(17) . . ?
C2 C1 C7 108.07(18) . . ?
C6 C1 C7 107.96(17) . . ?
C1 C2 C3 110.00(19) . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C4 C3 C9 109.3(3) . . ?
C4 C3 C2 109.3(3) . . ?
C9 C3 C2 109.7(3) . . ?
C4 C3 H3A 109.5 . . ?
C9 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C3 C4 C5 110.4(2) . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C10 C5 C6 108.9(2) . . ?
C10 C5 C4 109.3(2) . . ?
C6 C5 C4 109.5(2) . . ?
C10 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
C4 C5 H5A 109.7 . . ?
C1 C6 C5 109.15(19) . . ?
C1 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
C1 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
C8 C7 C1 110.08(18) . . ?
C8 C7 H7A 109.6 . . ?
C1 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C1 C7 H7B 109.6 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C10 110.6(2) . . ?
C9 C8 C7 109.41(19) . . ?
C10 C8 C7 108.4(2) . . ?
C9 C8 H8A 109.5 . . ?
C10 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C8 C9 C3 109.5(2) . . ?
C8 C9 H9A 109.8 . . ?
C3 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
C3 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
C5 C10 C8 109.6(2) . . ?
C5 C10 H10A 109.7 . . ?
C8 C10 H10A 109.7 . . ?
C5 C10 H10B 109.7 . . ?
C8 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 C16 120.63(18) . . ?
C12 C11 S1 118.19(14) . . ?
C16 C11 S1 121.18(16) . . ?
C13 C12 C11 117.92(19) . . ?
C13 C12 C17 116.8(2) . . ?
C11 C12 C17 125.22(19) . . ?
C14 C13 C12 122.8(2) . . ?
C14 C13 H13A 118.6 . . ?
C12 C13 H13A 118.6 . . ?
C15 C14 C13 117.7(2) . . ?
C15 C14 C18 121.6(2) . . ?
C13 C14 C18 120.7(3) . . ?
C14 C15 C16 123.57(19) . . ?
C14 C15 H15A 118.2 . . ?
C16 C15 H15A 118.2 . . ?
C15 C16 C11 117.4(2) . . ?
C15 C16 C19 116.82(19) . . ?
C11 C16 C19 125.82(19) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
O1 S1 N1 C1 -33.5(2) . . . . ?
O2 S1 N1 C1 -162.32(17) . . . . ?
C11 S1 N1 C1 84.13(19) . . . . ?
S1 N1 C1 C2 80.8(2) . . . . ?
S1 N1 C1 C6 -43.7(3) . . . . ?
S1 N1 C1 C7 -161.87(16) . . . . ?
N1 C1 C2 C3 176.5(2) . . . . ?
C6 C1 C2 C3 -58.4(3) . . . . ?
C7 C1 C2 C3 59.9(3) . . . . ?
C1 C2 C3 C4 59.1(3) . . . . ?
C1 C2 C3 C9 -60.7(3) . . . . ?
C9 C3 C4 C5 59.8(3) . . . . ?
C2 C3 C4 C5 -60.2(3) . . . . ?
C3 C4 C5 C10 -59.0(3) . . . . ?
C3 C4 C5 C6 60.2(3) . . . . ?
N1 C1 C6 C5 -178.05(19) . . . . ?
C2 C1 C6 C5 57.8(3) . . . . ?
C7 C1 C6 C5 -60.6(3) . . . . ?
C10 C5 C6 C1 61.8(3) . . . . ?
C4 C5 C6 C1 -57.7(3) . . . . ?
N1 C1 C7 C8 -178.71(16) . . . . ?
C2 C1 C7 C8 -59.8(2) . . . . ?
C6 C1 C7 C8 60.5(2) . . . . ?
C1 C7 C8 C9 60.2(3) . . . . ?
C1 C7 C8 C10 -60.6(2) . . . . ?
C10 C8 C9 C3 59.7(3) . . . . ?
C7 C8 C9 C3 -59.6(3) . . . . ?
C4 C3 C9 C8 -59.9(3) . . . . ?
C2 C3 C9 C8 59.9(3) . . . . ?
C6 C5 C10 C8 -62.0(3) . . . . ?
C4 C5 C10 C8 57.7(3) . . . . ?
C9 C8 C10 C5 -59.0(3) . . . . ?
C7 C8 C10 C5 61.0(3) . . . . ?
O1 S1 C11 C12 171.39(15) . . . . ?
O2 S1 C11 C12 -60.31(17) . . . . ?
N1 S1 C11 C12 52.41(17) . . . . ?
O1 S1 C11 C16 -9.55(19) . . . . ?
O2 S1 C11 C16 118.76(17) . . . . ?
N1 S1 C11 C16 -128.53(16) . . . . ?
C16 C11 C12 C13 2.3(3) . . . . ?
S1 C11 C12 C13 -178.67(15) . . . . ?
C16 C11 C12 C17 -176.4(2) . . . . ?
S1 C11 C12 C17 2.7(3) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C17 C12 C13 C14 178.1(2) . . . . ?
C12 C13 C14 C15 -1.0(4) . . . . ?
C12 C13 C14 C18 -179.9(2) . . . . ?
C13 C14 C15 C16 1.2(3) . . . . ?
C18 C14 C15 C16 -180.0(2) . . . . ?
C14 C15 C16 C11 0.4(3) . . . . ?
C14 C15 C16 C19 -179.5(2) . . . . ?
C12 C11 C16 C15 -2.1(3) . . . . ?
S1 C11 C16 C15 178.84(14) . . . . ?
C12 C11 C16 C19 177.7(2) . . . . ?
S1 C11 C16 C19 -1.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.77(2) 2.18(3) 2.932(2) 167(2) 2_655

####################################################################### 
# 
# 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_16
_database_code_depnum_ccdc_archive 'CCDC 1962768'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2019-10-31 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;

_audit_creation_date             2017-03-10T15:18:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C17 H20 F3 N O3 S'
_chemical_formula_sum            'C17 H20 F3 N O3 S'
_chemical_formula_weight         375.4

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.0788(5)
_cell_length_b                   12.2658(6)
_cell_length_c                   12.9608(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.4380(10)
_cell_angle_gamma                90
_cell_volume                     1670.84(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5717
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      30.13

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             784

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

_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.6711
_exptl_absorpt_correction_T_max  0.7462

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

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_number            24560
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.114
_diffrn_reflns_theta_max         31.52
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             5546
_reflns_number_gt                4443
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   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)+(0.0800P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5546
_refine_ls_number_parameters     306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1321
_refine_ls_wR_factor_gt          0.1215
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.067

#----------------------------------------------------------------------------#
#                   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'
F F 0.0171 0.0103 '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 0.51662(3) 0.30691(3) 0.52466(3) 0.01676(9) Uani 1 1 d . . . . .
F1 F 0.08546(10) 0.43393(9) 0.25573(9) 0.0387(3) Uani 1 1 d . . . . .
F2 F 0.20866(10) 0.55107(8) 0.35876(10) 0.0370(3) Uani 1 1 d . . . . .
F3 F 0.11402(12) 0.42997(10) 0.42584(10) 0.0430(3) Uani 1 1 d . . . . .
O1 O 0.47959(10) 0.39258(8) 0.58477(8) 0.0226(2) Uani 1 1 d . . . . .
O2 O 0.61086(10) 0.23011(9) 0.58284(9) 0.0231(2) Uani 1 1 d . . . . .
O3 O 0.27620(10) 0.38579(9) 0.36738(10) 0.0272(2) Uani 1 1 d . . . . .
N1 N 0.56092(12) 0.36645(10) 0.43287(10) 0.0180(2) Uani 1 1 d . . . . .
C1 C 0.60568(13) 0.31691(10) 0.34671(11) 0.0160(2) Uani 1 1 d . . . . .
C2 C 0.49260(15) 0.28689(14) 0.24589(12) 0.0259(3) Uani 1 1 d . . . . .
C3 C 0.54305(17) 0.24545(15) 0.15473(13) 0.0305(3) Uani 1 1 d . . . . .
C4 C 0.6229(2) 0.33482(17) 0.12556(17) 0.0420(5) Uani 1 1 d . . . . .
C5 C 0.7348(2) 0.36361(15) 0.22417(18) 0.0411(5) Uani 1 1 d . . . . .
C6 C 0.68576(19) 0.40533(13) 0.31565(16) 0.0322(4) Uani 1 1 d . . . . .
C7 C 0.68719(15) 0.21543(13) 0.38571(13) 0.0247(3) Uani 1 1 d . . . . .
C8 C 0.73801(17) 0.17419(13) 0.29466(14) 0.0287(3) Uani 1 1 d . . . . .
C9 C 0.62598(17) 0.14527(13) 0.19577(14) 0.0289(3) Uani 1 1 d . . . . .
C10 C 0.81739(17) 0.26318(17) 0.26476(18) 0.0390(4) Uani 1 1 d . . . . .
C11 C 0.37905(13) 0.22788(11) 0.45982(11) 0.0180(2) Uani 1 1 d . . . . .
C12 C 0.26989(13) 0.27387(11) 0.38722(11) 0.0196(3) Uani 1 1 d . . . . .
C13 C 0.16643(15) 0.20984(13) 0.33334(13) 0.0244(3) Uani 1 1 d . . . . .
C14 C 0.17133(16) 0.09878(13) 0.35351(13) 0.0279(3) Uani 1 1 d . . . . .
C15 C 0.27806(16) 0.05113(12) 0.42615(14) 0.0275(3) Uani 1 1 d . . . . .
C16 C 0.38218(15) 0.11598(12) 0.47919(12) 0.0225(3) Uani 1 1 d . . . . .
C17 C 0.17218(14) 0.44837(12) 0.35262(12) 0.0233(3) Uani 1 1 d . . . . .
H1 H 0.5352(18) 0.4254(17) 0.4203(16) 0.023(5) Uiso 1 1 d . . . . .
H2 H 0.437(2) 0.2247(19) 0.2678(18) 0.040(6) Uiso 1 1 d . . . . .
H3 H 0.440(2) 0.3588(18) 0.2205(17) 0.034(5) Uiso 1 1 d . . . . .
H4 H 0.466(2) 0.2299(19) 0.0895(18) 0.038(6) Uiso 1 1 d . . . . .
H5 H 0.647(3) 0.306(2) 0.054(2) 0.059(8) Uiso 1 1 d . . . . .
H6 H 0.577(3) 0.402(2) 0.099(2) 0.062(8) Uiso 1 1 d . . . . .
H7 H 0.789(2) 0.416(2) 0.209(2) 0.051(7) Uiso 1 1 d . . . . .
H8 H 0.759(2) 0.4199(19) 0.3866(19) 0.041(6) Uiso 1 1 d . . . . .
H9 H 0.626(2) 0.4710(18) 0.2919(17) 0.034(5) Uiso 1 1 d . . . . .
H10 H 0.627(2) 0.1525(19) 0.4011(18) 0.039(6) Uiso 1 1 d . . . . .
H11 H 0.758(2) 0.2395(17) 0.4542(18) 0.036(5) Uiso 1 1 d . . . . .
H12 H 0.789(2) 0.1174(18) 0.3177(17) 0.033(5) Uiso 1 1 d . . . . .
H13 H 0.577(2) 0.0861(19) 0.2146(18) 0.038(6) Uiso 1 1 d . . . . .
H14 H 0.659(2) 0.116(2) 0.136(2) 0.047(6) Uiso 1 1 d . . . . .
H15 H 0.876(3) 0.279(2) 0.333(2) 0.058(8) Uiso 1 1 d . . . . .
H16 H 0.853(2) 0.240(2) 0.203(2) 0.052(7) Uiso 1 1 d . . . . .
H17 H 0.099(2) 0.2331(19) 0.2850(19) 0.041(6) Uiso 1 1 d . . . . .
H18 H 0.102(2) 0.0528(19) 0.3127(18) 0.038(6) Uiso 1 1 d . . . . .
H19 H 0.283(2) -0.0243(18) 0.4360(17) 0.034(5) Uiso 1 1 d . . . . .
H20 H 0.4575(19) 0.0848(17) 0.5296(16) 0.028(5) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 O2 1.4311(11) . ?
S1 O1 1.4428(10) . ?
S1 N1 1.5997(12) . ?
S1 C11 1.7772(14) . ?
F1 C17 1.3298(18) . ?
F2 C17 1.3176(18) . ?
F3 C17 1.3242(19) . ?
O3 C17 1.3470(18) . ?
O3 C12 1.4025(17) . ?
N1 C1 1.4875(16) . ?
N1 H1 0.78(2) . ?
C1 C7 1.5269(19) . ?
C1 C6 1.533(2) . ?
C1 C2 1.542(2) . ?
C2 C3 1.544(2) . ?
C2 H2 1.07(2) . ?
C2 H3 1.05(2) . ?
C3 C9 1.526(2) . ?
C3 C4 1.529(3) . ?
C3 H4 1.01(2) . ?
C4 C5 1.514(3) . ?
C4 H5 1.10(3) . ?
C4 H6 0.97(3) . ?
C5 C10 1.525(3) . ?
C5 C6 1.540(2) . ?
C5 H7 0.95(3) . ?
C6 H8 1.03(2) . ?
C6 H9 1.03(2) . ?
C7 C8 1.545(2) . ?
C7 H10 1.08(2) . ?
C7 H11 1.02(2) . ?
C8 C9 1.518(2) . ?
C8 C10 1.527(3) . ?
C8 H12 0.89(2) . ?
C9 H13 0.98(2) . ?
C9 H14 1.02(2) . ?
C10 H15 0.93(3) . ?
C10 H16 1.04(3) . ?
C11 C16 1.3937(19) . ?
C11 C12 1.3951(19) . ?
C12 C13 1.383(2) . ?
C13 C14 1.385(2) . ?
C13 H17 0.86(2) . ?
C14 C15 1.386(2) . ?
C14 H18 0.97(2) . ?
C15 C16 1.391(2) . ?
C15 H19 0.93(2) . ?
C16 H20 0.96(2) . ?

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
O2 S1 O1 118.66(6) . . ?
O2 S1 N1 110.37(6) . . ?
O1 S1 N1 105.99(6) . . ?
O2 S1 C11 105.29(6) . . ?
O1 S1 C11 107.75(6) . . ?
N1 S1 C11 108.44(6) . . ?
C17 O3 C12 119.60(12) . . ?
C1 N1 S1 128.71(9) . . ?
C1 N1 H1 114.3(14) . . ?
S1 N1 H1 113.8(14) . . ?
N1 C1 C7 112.78(11) . . ?
N1 C1 C6 105.43(11) . . ?
C7 C1 C6 109.44(12) . . ?
N1 C1 C2 111.06(11) . . ?
C7 C1 C2 108.84(12) . . ?
C6 C1 C2 109.20(13) . . ?
C1 C2 C3 109.47(12) . . ?
C1 C2 H2 109.0(12) . . ?
C3 C2 H2 110.2(13) . . ?
C1 C2 H3 106.7(12) . . ?
C3 C2 H3 109.7(11) . . ?
H2 C2 H3 111.7(16) . . ?
C9 C3 C4 109.38(15) . . ?
C9 C3 C2 108.79(13) . . ?
C4 C3 C2 109.32(14) . . ?
C9 C3 H4 113.3(13) . . ?
C4 C3 H4 109.2(13) . . ?
C2 C3 H4 106.8(13) . . ?
C5 C4 C3 109.98(15) . . ?
C5 C4 H5 115.8(14) . . ?
C3 C4 H5 107.1(14) . . ?
C5 C4 H6 107.1(17) . . ?
C3 C4 H6 114.6(16) . . ?
H5 C4 H6 102(2) . . ?
C4 C5 C10 110.15(15) . . ?
C4 C5 C6 109.46(17) . . ?
C10 C5 C6 108.79(17) . . ?
C4 C5 H7 112.7(15) . . ?
C10 C5 H7 105.8(15) . . ?
C6 C5 H7 109.8(15) . . ?
C1 C6 C5 109.97(13) . . ?
C1 C6 H8 104.3(13) . . ?
C5 C6 H8 111.9(13) . . ?
C1 C6 H9 105.1(12) . . ?
C5 C6 H9 112.5(12) . . ?
H8 C6 H9 112.6(18) . . ?
C1 C7 C8 109.53(12) . . ?
C1 C7 H10 107.8(12) . . ?
C8 C7 H10 107.7(12) . . ?
C1 C7 H11 105.2(12) . . ?
C8 C7 H11 113.2(12) . . ?
H10 C7 H11 113.2(17) . . ?
C9 C8 C10 109.61(15) . . ?
C9 C8 C7 108.87(14) . . ?
C10 C8 C7 109.77(14) . . ?
C9 C8 H12 111.3(14) . . ?
C10 C8 H12 107.0(14) . . ?
C7 C8 H12 110.3(14) . . ?
C8 C9 C3 110.34(13) . . ?
C8 C9 H13 109.4(13) . . ?
C3 C9 H13 111.2(13) . . ?
C8 C9 H14 109.2(14) . . ?
C3 C9 H14 109.9(14) . . ?
H13 C9 H14 106.7(19) . . ?
C5 C10 C8 109.52(14) . . ?
C5 C10 H15 109.0(17) . . ?
C8 C10 H15 101.2(18) . . ?
C5 C10 H16 106.5(14) . . ?
C8 C10 H16 113.3(14) . . ?
H15 C10 H16 117(2) . . ?
C16 C11 C12 119.11(13) . . ?
C16 C11 S1 118.89(11) . . ?
C12 C11 S1 121.95(10) . . ?
C13 C12 C11 120.95(13) . . ?
C13 C12 O3 123.01(13) . . ?
C11 C12 O3 115.89(12) . . ?
C12 C13 C14 119.11(15) . . ?
C12 C13 H17 124.9(16) . . ?
C14 C13 H17 115.9(16) . . ?
C13 C14 C15 121.13(15) . . ?
C13 C14 H18 119.7(13) . . ?
C15 C14 H18 119.1(13) . . ?
C14 C15 C16 119.38(14) . . ?
C14 C15 H19 121.0(13) . . ?
C16 C15 H19 119.5(13) . . ?
C15 C16 C11 120.31(14) . . ?
C15 C16 H20 120.9(12) . . ?
C11 C16 H20 118.8(12) . . ?
F2 C17 F3 109.22(13) . . ?
F2 C17 F1 107.49(12) . . ?
F3 C17 F1 106.50(13) . . ?
F2 C17 O3 107.70(13) . . ?
F3 C17 O3 112.92(13) . . ?
F1 C17 O3 112.85(13) . . ?

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
O2 S1 N1 C1 51.85(14) . . . . ?
O1 S1 N1 C1 -178.47(12) . . . . ?
C11 S1 N1 C1 -63.01(13) . . . . ?
S1 N1 C1 C7 -37.33(17) . . . . ?
S1 N1 C1 C6 -156.69(12) . . . . ?
S1 N1 C1 C2 85.14(15) . . . . ?
N1 C1 C2 C3 174.96(12) . . . . ?
C7 C1 C2 C3 -60.32(16) . . . . ?
C6 C1 C2 C3 59.10(16) . . . . ?
C1 C2 C3 C9 59.81(18) . . . . ?
C1 C2 C3 C4 -59.58(18) . . . . ?
C9 C3 C4 C5 -58.60(19) . . . . ?
C2 C3 C4 C5 60.43(19) . . . . ?
C3 C4 C5 C10 59.24(19) . . . . ?
C3 C4 C5 C6 -60.33(19) . . . . ?
N1 C1 C6 C5 -178.62(15) . . . . ?
C7 C1 C6 C5 59.83(19) . . . . ?
C2 C1 C6 C5 -59.21(19) . . . . ?
C4 C5 C6 C1 59.9(2) . . . . ?
C10 C5 C6 C1 -60.5(2) . . . . ?
N1 C1 C7 C8 -175.76(12) . . . . ?
C6 C1 C7 C8 -58.74(16) . . . . ?
C2 C1 C7 C8 60.53(16) . . . . ?
C1 C7 C8 C9 -60.63(17) . . . . ?
C1 C7 C8 C10 59.35(18) . . . . ?
C10 C8 C9 C3 -59.42(18) . . . . ?
C7 C8 C9 C3 60.66(18) . . . . ?
C4 C3 C9 C8 58.91(18) . . . . ?
C2 C3 C9 C8 -60.44(18) . . . . ?
C4 C5 C10 C8 -59.3(2) . . . . ?
C6 C5 C10 C8 60.6(2) . . . . ?
C9 C8 C10 C5 59.11(19) . . . . ?
C7 C8 C10 C5 -60.4(2) . . . . ?
O2 S1 C11 C16 3.42(13) . . . . ?
O1 S1 C11 C16 -124.13(11) . . . . ?
N1 S1 C11 C16 121.56(11) . . . . ?
O2 S1 C11 C12 -174.21(11) . . . . ?
O1 S1 C11 C12 58.23(13) . . . . ?
N1 S1 C11 C12 -56.08(13) . . . . ?
C16 C11 C12 C13 -1.1(2) . . . . ?
S1 C11 C12 C13 176.55(11) . . . . ?
C16 C11 C12 O3 -176.70(12) . . . . ?
S1 C11 C12 O3 0.94(18) . . . . ?
C17 O3 C12 C13 40.8(2) . . . . ?
C17 O3 C12 C11 -143.73(14) . . . . ?
C11 C12 C13 C14 1.0(2) . . . . ?
O3 C12 C13 C14 176.30(14) . . . . ?
C12 C13 C14 C15 -0.3(2) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C14 C15 C16 C11 0.2(2) . . . . ?
C12 C11 C16 C15 0.4(2) . . . . ?
S1 C11 C16 C15 -177.26(12) . . . . ?
C12 O3 C17 F2 166.87(13) . . . . ?
C12 O3 C17 F3 46.20(19) . . . . ?
C12 O3 C17 F1 -74.65(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.78(2) 2.24(2) 2.9873(16) 162.8(19) 3_666
C13 H17 F1 0.86(2) 2.49(2) 2.967(2) 115.8(19) .

####################################################################### 
# 
# 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_18_2H2O
_database_code_depnum_ccdc_archive 'CCDC 1962779'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2019-10-31 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;

_audit_creation_date             2017-04-04T20:40:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C18 H24 N2 O3 S, 2(H2 O)'
_chemical_formula_sum            'C18 H28 N2 O5 S'
_chemical_formula_weight         384.48
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P n'
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_Int_Tables_number      7
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   13.3372(6)
_cell_length_b                   6.7727(3)
_cell_length_c                   21.8857(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.262(2)
_cell_angle_gamma                90
_cell_volume                     1938.84(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6300
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      29.21

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             824

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

_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.6317
_exptl_absorpt_correction_T_max  0.7461

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

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_number            26492
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.966
_diffrn_reflns_theta_max         30.525
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.963
_reflns_Friedel_coverage         0.968
_reflns_number_total             11607
_reflns_number_gt                9385
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_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)+(0.0600P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         11607
_refine_ls_number_parameters     519
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.1037
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 3707 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(4)
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.055

#----------------------------------------------------------------------------#
#                   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 0.63545(5) 0.14710(11) 0.30384(3) 0.01769(16) Uani 1 1 d . . . . .
S2 S -0.13588(5) 0.63444(11) 0.19559(3) 0.01658(15) Uani 1 1 d . . . . .
O1 O 0.60929(18) 0.3513(3) 0.31229(11) 0.0244(5) Uani 1 1 d . . . . .
O2 O 0.68780(17) 0.0969(4) 0.25429(10) 0.0259(5) Uani 1 1 d . . . . .
O3 O 0.91305(19) -0.4204(3) 0.54085(11) 0.0242(5) Uani 1 1 d . . . . .
O4 O -0.24393(16) 0.6082(4) 0.19305(10) 0.0243(5) Uani 1 1 d . . . . .
O5 O -0.09975(18) 0.8269(3) 0.18200(11) 0.0228(5) Uani 1 1 d . . . . .
O6 O 0.07469(19) 0.1073(3) 0.45765(10) 0.0248(5) Uani 1 1 d . . . . .
N1 N 0.53256(19) 0.0189(4) 0.29141(12) 0.0179(5) Uani 1 1 d . . . . .
N2 N 0.9051(2) -0.0843(4) 0.54232(12) 0.0180(5) Uani 1 1 d . . . . .
N3 N -0.10659(19) 0.4775(4) 0.14754(11) 0.0165(5) Uani 1 1 d . . . . .
N4 N 0.0773(2) 0.4436(4) 0.45328(12) 0.0181(5) Uani 1 1 d . . . . .
C1 C 0.4447(2) 0.0391(4) 0.32361(13) 0.0170(6) Uani 1 1 d . . . . .
C2 C 0.4776(2) 0.0615(5) 0.39421(14) 0.0235(7) Uani 1 1 d . . . . .
H2A H 0.51889 0.182909 0.404013 0.028 Uiso 1 1 calc R U . . .
H2B H 0.520076 -0.052782 0.411527 0.028 Uiso 1 1 calc R U . . .
C3 C 0.3816(3) 0.0730(6) 0.42373(17) 0.0337(8) Uani 1 1 d . . . . .
H3A H 0.403045 0.088197 0.469889 0.04 Uiso 1 1 calc R U . . .
C4 C 0.3196(3) -0.1181(6) 0.40925(18) 0.0354(9) Uani 1 1 d . . . . .
H4A H 0.361958 -0.232756 0.426433 0.043 Uiso 1 1 calc R U . . .
H4B H 0.258828 -0.113742 0.428924 0.043 Uiso 1 1 calc R U . . .
C5 C 0.2861(3) -0.1405(5) 0.33897(18) 0.0306(8) Uani 1 1 d . . . . .
H5A H 0.245415 -0.264558 0.329413 0.037 Uiso 1 1 calc R U . . .
C6 C 0.3816(3) -0.1504(5) 0.30928(16) 0.0256(7) Uani 1 1 d . . . . .
H6A H 0.42378 -0.265823 0.32593 0.031 Uiso 1 1 calc R U . . .
H6B H 0.360587 -0.166767 0.263624 0.031 Uiso 1 1 calc R U . . .
C7 C 0.2205(3) 0.0374(6) 0.3128(2) 0.0356(9) Uani 1 1 d . . . . .
H7A H 0.197694 0.022822 0.26721 0.043 Uiso 1 1 calc R U . . .
H7B H 0.159096 0.04428 0.331877 0.043 Uiso 1 1 calc R U . . .
C8 C 0.2830(3) 0.2263(6) 0.3271(2) 0.0346(9) Uani 1 1 d . . . . .
H8A H 0.240324 0.342367 0.309986 0.042 Uiso 1 1 calc R U . . .
C9 C 0.3779(3) 0.2147(5) 0.29670(18) 0.0272(7) Uani 1 1 d . . . . .
H9A H 0.356163 0.1989 0.251061 0.033 Uiso 1 1 calc R U . . .
H9B H 0.417767 0.33852 0.304742 0.033 Uiso 1 1 calc R U . . .
C10 C 0.3176(3) 0.2498(6) 0.3974(2) 0.0411(10) Uani 1 1 d . . . . .
H10A H 0.358315 0.372181 0.406591 0.049 Uiso 1 1 calc R U . . .
H10B H 0.257083 0.260391 0.417207 0.049 Uiso 1 1 calc R U . . .
C11 C 0.7156(2) 0.0734(4) 0.37388(13) 0.0165(6) Uani 1 1 d . . . . .
C12 C 0.7455(2) 0.2123(5) 0.42094(14) 0.0202(6) Uani 1 1 d . . . . .
H12A H 0.722636 0.345168 0.415514 0.024 Uiso 1 1 calc R U . . .
C13 C 0.8088(2) 0.1536(5) 0.47555(15) 0.0219(6) Uani 1 1 d . . . . .
H13A H 0.830504 0.247999 0.507516 0.026 Uiso 1 1 calc R U . . .
C14 C 0.8416(2) -0.0414(4) 0.48466(13) 0.0159(6) Uani 1 1 d . . . . .
C15 C 0.8131(2) -0.1792(4) 0.43684(14) 0.0202(6) Uani 1 1 d . . . . .
H15A H 0.836845 -0.311474 0.442109 0.024 Uiso 1 1 calc R U . . .
C16 C 0.7498(2) -0.1214(5) 0.38160(14) 0.0202(6) Uani 1 1 d . . . . .
H16A H 0.729821 -0.214499 0.349035 0.024 Uiso 1 1 calc R U . . .
C17 C 0.9358(2) -0.2623(4) 0.56750(14) 0.0187(6) Uani 1 1 d . . . . .
C18 C 0.9995(3) -0.2513(5) 0.63236(16) 0.0248(7) Uani 1 1 d . . . . .
H18A H 1.021388 -0.114606 0.641714 0.037 Uiso 1 1 calc R U . . .
H18B H 1.059824 -0.335993 0.635084 0.037 Uiso 1 1 calc R U . . .
H18C H 0.958848 -0.296108 0.662467 0.037 Uiso 1 1 calc R U . . .
C19 C -0.0084(2) 0.4621(4) 0.12542(14) 0.0178(6) Uani 1 1 d . . . . .
C20 C -0.0099(3) 0.2602(5) 0.09362(18) 0.0312(8) Uani 1 1 d . . . . .
H20A H -0.070474 0.250805 0.059459 0.037 Uiso 1 1 calc R U . . .
H20B H -0.014728 0.154398 0.124121 0.037 Uiso 1 1 calc R U . . .
C21 C 0.0884(3) 0.2322(6) 0.0671(2) 0.0403(10) Uani 1 1 d . . . . .
H21A H 0.087386 0.099662 0.046851 0.048 Uiso 1 1 calc R U . . .
C22 C 0.1805(3) 0.2470(7) 0.1204(2) 0.0470(11) Uani 1 1 d . . . . .
H22A H 0.244028 0.226393 0.104196 0.056 Uiso 1 1 calc R U . . .
H22B H 0.176455 0.142877 0.151543 0.056 Uiso 1 1 calc R U . . .
C23 C 0.1833(3) 0.4497(7) 0.15123(19) 0.0375(9) Uani 1 1 d . . . . .
H23A H 0.24484 0.459833 0.185513 0.045 Uiso 1 1 calc R U . . .
C24 C 0.0850(2) 0.4767(6) 0.17801(16) 0.0275(7) Uani 1 1 d . . . . .
H24A H 0.081613 0.373431 0.209552 0.033 Uiso 1 1 calc R U . . .
H24B H 0.086148 0.607168 0.198545 0.033 Uiso 1 1 calc R U . . .
C25 C -0.0036(3) 0.6230(5) 0.07640(17) 0.0281(7) Uani 1 1 d . . . . .
H25A H -0.003335 0.755186 0.095759 0.034 Uiso 1 1 calc R U . . .
H25B H -0.0644 0.613699 0.042388 0.034 Uiso 1 1 calc R U . . .
C26 C 0.0948(3) 0.5952(6) 0.04973(18) 0.0363(9) Uani 1 1 d . . . . .
H26A H 0.098572 0.700479 0.018223 0.044 Uiso 1 1 calc R U . . .
C27 C 0.0926(3) 0.3944(7) 0.01902(19) 0.0425(10) Uani 1 1 d . . . . .
H27A H 0.15454 0.377311 0.000921 0.051 Uiso 1 1 calc R U . . .
H27B H 0.032015 0.384632 -0.015124 0.051 Uiso 1 1 calc R U . . .
C28 C 0.1866(3) 0.6120(6) 0.1029(2) 0.0408(10) Uani 1 1 d . . . . .
H28A H 0.18652 0.743053 0.12294 0.049 Uiso 1 1 calc R U . . .
H28B H 0.25039 0.599935 0.08642 0.049 Uiso 1 1 calc R U . . .
C29 C -0.0727(2) 0.5752(4) 0.27188(13) 0.0170(6) Uani 1 1 d . . . . .
C30 C -0.0811(2) 0.3850(4) 0.29440(14) 0.0207(6) Uani 1 1 d . . . . .
H30A H -0.120357 0.288732 0.268588 0.025 Uiso 1 1 calc R U . . .
C31 C -0.0324(2) 0.3354(4) 0.35447(15) 0.0199(6) Uani 1 1 d . . . . .
H31A H -0.037986 0.205473 0.369834 0.024 Uiso 1 1 calc R U . . .
C32 C 0.0253(2) 0.4792(4) 0.39235(13) 0.0170(6) Uani 1 1 d . . . . .
C33 C 0.0303(3) 0.6708(5) 0.36966(15) 0.0219(6) Uani 1 1 d . . . . .
H33A H 0.067189 0.769494 0.395621 0.026 Uiso 1 1 calc R U . . .
C34 C -0.0181(2) 0.7180(5) 0.30942(15) 0.0211(6) Uani 1 1 d . . . . .
H34A H -0.013727 0.848209 0.294036 0.025 Uiso 1 1 calc R U . . .
C35 C 0.1003(2) 0.2673(5) 0.48217(14) 0.0191(6) Uani 1 1 d . . . . .
C36 C 0.1639(3) 0.2826(5) 0.54689(15) 0.0280(7) Uani 1 1 d . . . . .
H36A H 0.169501 0.421435 0.559742 0.042 Uiso 1 1 calc R U . . .
H36B H 0.232264 0.229214 0.547177 0.042 Uiso 1 1 calc R U . . .
H36C H 0.131287 0.207148 0.575878 0.042 Uiso 1 1 calc R U . . .
O7 O 0.57532(19) 0.6668(3) 0.23274(11) 0.0191(5) Uani 1 1 d . . . . .
O8 O 0.9500(2) 0.2517(4) 0.61770(14) 0.0382(7) Uani 1 1 d . . . . .
O9 O -0.23628(17) 0.1373(3) 0.14410(10) 0.0197(4) Uani 1 1 d . . . . .
O10 O 0.1522(2) 0.7796(4) 0.52291(12) 0.0300(6) Uani 1 1 d . . . . .
H1 H 0.540(3) -0.093(6) 0.2760(18) 0.022(9) Uiso 1 1 d . . . . .
H2 H 0.927(3) 0.012(5) 0.5641(16) 0.014(9) Uiso 1 1 d . . . . .
H3 H -0.148(3) 0.371(6) 0.1473(19) 0.031(11) Uiso 1 1 d . . . . .
H4 H 0.102(3) 0.538(6) 0.4725(16) 0.015(9) Uiso 1 1 d . . . . .
H5 H 0.629(3) 0.676(6) 0.226(2) 0.029(12) Uiso 1 1 d . . . . .
H6 H 0.572(3) 0.563(6) 0.255(2) 0.030(11) Uiso 1 1 d . . . . .
H7 H 0.943(4) 0.347(7) 0.597(2) 0.048(14) Uiso 1 1 d . . . . .
H8 H 0.991(3) 0.263(6) 0.649(2) 0.033(12) Uiso 1 1 d . . . . .
H9 H -0.198(3) 0.029(7) 0.1516(19) 0.033(11) Uiso 1 1 d . . . . .
H10 H -0.269(4) 0.141(6) 0.174(2) 0.040(12) Uiso 1 1 d . . . . .
H11 H 0.128(3) 0.883(6) 0.5028(19) 0.031(11) Uiso 1 1 d . . . . .
H12 H 0.184(3) 0.796(6) 0.5615(19) 0.021(9) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 O2 1.440(2) . ?
S1 O1 1.447(2) . ?
S1 N1 1.602(3) . ?
S1 C11 1.761(3) . ?
S2 O5 1.441(2) . ?
S2 O4 1.442(2) . ?
S2 N3 1.596(3) . ?
S2 C29 1.763(3) . ?
O3 C17 1.229(4) . ?
O6 C35 1.228(4) . ?
N1 C1 1.487(4) . ?
N1 H1 0.84(4) . ?
N2 C17 1.355(4) . ?
N2 C14 1.406(4) . ?
N2 H2 0.83(4) . ?
N3 C19 1.485(4) . ?
N3 H3 0.90(4) . ?
N4 C35 1.358(4) . ?
N4 C32 1.399(4) . ?
N4 H4 0.80(4) . ?
C1 C2 1.529(4) . ?
C1 C6 1.533(4) . ?
C1 C9 1.533(4) . ?
C2 C3 1.544(5) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C10 1.517(6) . ?
C3 C4 1.536(6) . ?
C3 H3A 1 . ?
C4 C5 1.523(6) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 C7 1.533(5) . ?
C5 C6 1.540(5) . ?
C5 H5A 1 . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 C8 1.526(6) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 C10 1.526(6) . ?
C8 C9 1.542(5) . ?
C8 H8A 1 . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C12 1.394(4) . ?
C11 C16 1.396(4) . ?
C12 C13 1.380(4) . ?
C12 H12A 0.95 . ?
C13 C14 1.393(4) . ?
C13 H13A 0.95 . ?
C14 C15 1.398(4) . ?
C15 C16 1.389(4) . ?
C15 H15A 0.95 . ?
C16 H16A 0.95 . ?
C17 C18 1.507(4) . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C19 C24 1.526(4) . ?
C19 C20 1.533(5) . ?
C19 C25 1.540(4) . ?
C20 C21 1.545(5) . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?
C21 C22 1.522(7) . ?
C21 C27 1.530(6) . ?
C21 H21A 1 . ?
C22 C23 1.527(7) . ?
C22 H22A 0.99 . ?
C22 H22B 0.99 . ?
C23 C28 1.531(6) . ?
C23 C24 1.548(5) . ?
C23 H23A 1 . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
C25 C26 1.549(5) . ?
C25 H25A 0.99 . ?
C25 H25B 0.99 . ?
C26 C27 1.515(6) . ?
C26 C28 1.520(6) . ?
C26 H26A 1 . ?
C27 H27A 0.99 . ?
C27 H27B 0.99 . ?
C28 H28A 0.99 . ?
C28 H28B 0.99 . ?
C29 C34 1.381(4) . ?
C29 C30 1.391(4) . ?
C30 C31 1.389(4) . ?
C30 H30A 0.95 . ?
C31 C32 1.407(4) . ?
C31 H31A 0.95 . ?
C32 C33 1.396(4) . ?
C33 C34 1.387(4) . ?
C33 H33A 0.95 . ?
C34 H34A 0.95 . ?
C35 C36 1.506(4) . ?
C36 H36A 0.98 . ?
C36 H36B 0.98 . ?
C36 H36C 0.98 . ?
O7 H5 0.76(5) . ?
O7 H6 0.86(4) . ?
O8 H7 0.78(5) . ?
O8 H8 0.80(5) . ?
O9 H9 0.89(5) . ?
O9 H10 0.85(5) . ?
O10 H11 0.85(4) . ?
O10 H12 0.87(4) . ?

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
O2 S1 O1 119.08(14) . . ?
O2 S1 N1 105.63(14) . . ?
O1 S1 N1 108.66(14) . . ?
O2 S1 C11 106.71(14) . . ?
O1 S1 C11 106.26(14) . . ?
N1 S1 C11 110.39(14) . . ?
O5 S2 O4 118.39(14) . . ?
O5 S2 N3 109.36(14) . . ?
O4 S2 N3 105.30(14) . . ?
O5 S2 C29 106.51(14) . . ?
O4 S2 C29 107.30(14) . . ?
N3 S2 C29 109.83(14) . . ?
C1 N1 S1 126.7(2) . . ?
C1 N1 H1 116(3) . . ?
S1 N1 H1 113(3) . . ?
C17 N2 C14 129.1(3) . . ?
C17 N2 H2 115(2) . . ?
C14 N2 H2 116(2) . . ?
C19 N3 S2 127.3(2) . . ?
C19 N3 H3 121(3) . . ?
S2 N3 H3 108(3) . . ?
C35 N4 C32 128.3(3) . . ?
C35 N4 H4 115(3) . . ?
C32 N4 H4 116(3) . . ?
N1 C1 C2 113.0(2) . . ?
N1 C1 C6 106.1(2) . . ?
C2 C1 C6 109.1(3) . . ?
N1 C1 C9 110.0(2) . . ?
C2 C1 C9 110.0(3) . . ?
C6 C1 C9 108.4(3) . . ?
C1 C2 C3 109.3(3) . . ?
C1 C2 H2A 109.8 . . ?
C3 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
C3 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
C10 C3 C4 110.3(3) . . ?
C10 C3 C2 109.4(3) . . ?
C4 C3 C2 109.1(3) . . ?
C10 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C5 C4 C3 109.4(3) . . ?
C5 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
C5 C4 H4B 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
C4 C5 C7 109.4(3) . . ?
C4 C5 C6 109.1(3) . . ?
C7 C5 C6 109.6(3) . . ?
C4 C5 H5A 109.6 . . ?
C7 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
C1 C6 C5 110.1(3) . . ?
C1 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C1 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 C5 109.4(3) . . ?
C8 C7 H7A 109.8 . . ?
C5 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
C5 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
C7 C8 C10 109.8(3) . . ?
C7 C8 C9 109.3(3) . . ?
C10 C8 C9 109.2(3) . . ?
C7 C8 H8A 109.5 . . ?
C10 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C1 C9 C8 109.7(3) . . ?
C1 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
C1 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C3 C10 C8 109.7(3) . . ?
C3 C10 H10A 109.7 . . ?
C8 C10 H10A 109.7 . . ?
C3 C10 H10B 109.7 . . ?
C8 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 C16 120.6(3) . . ?
C12 C11 S1 119.3(2) . . ?
C16 C11 S1 120.1(2) . . ?
C13 C12 C11 118.9(3) . . ?
C13 C12 H12A 120.5 . . ?
C11 C12 H12A 120.5 . . ?
C12 C13 C14 121.2(3) . . ?
C12 C13 H13A 119.4 . . ?
C14 C13 H13A 119.4 . . ?
C13 C14 C15 119.6(3) . . ?
C13 C14 N2 116.2(3) . . ?
C15 C14 N2 124.2(3) . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15A 120.2 . . ?
C14 C15 H15A 120.2 . . ?
C15 C16 C11 120.0(3) . . ?
C15 C16 H16A 120 . . ?
C11 C16 H16A 120 . . ?
O3 C17 N2 123.7(3) . . ?
O3 C17 C18 122.1(3) . . ?
N2 C17 C18 114.1(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 C24 113.1(2) . . ?
N3 C19 C20 106.1(3) . . ?
C24 C19 C20 109.7(3) . . ?
N3 C19 C25 109.7(2) . . ?
C24 C19 C25 109.9(3) . . ?
C20 C19 C25 108.3(3) . . ?
C19 C20 C21 110.1(3) . . ?
C19 C20 H20A 109.6 . . ?
C21 C20 H20A 109.6 . . ?
C19 C20 H20B 109.6 . . ?
C21 C20 H20B 109.6 . . ?
H20A C20 H20B 108.2 . . ?
C22 C21 C27 110.3(4) . . ?
C22 C21 C20 108.8(3) . . ?
C27 C21 C20 108.5(3) . . ?
C22 C21 H21A 109.8 . . ?
C27 C21 H21A 109.8 . . ?
C20 C21 H21A 109.8 . . ?
C21 C22 C23 110.2(3) . . ?
C21 C22 H22A 109.6 . . ?
C23 C22 H22A 109.6 . . ?
C21 C22 H22B 109.6 . . ?
C23 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
C22 C23 C28 110.0(3) . . ?
C22 C23 C24 108.9(3) . . ?
C28 C23 C24 108.5(3) . . ?
C22 C23 H23A 109.8 . . ?
C28 C23 H23A 109.8 . . ?
C24 C23 H23A 109.8 . . ?
C19 C24 C23 109.5(3) . . ?
C19 C24 H24A 109.8 . . ?
C23 C24 H24A 109.8 . . ?
C19 C24 H24B 109.8 . . ?
C23 C24 H24B 109.8 . . ?
H24A C24 H24B 108.2 . . ?
C19 C25 C26 109.3(3) . . ?
C19 C25 H25A 109.8 . . ?
C26 C25 H25A 109.8 . . ?
C19 C25 H25B 109.8 . . ?
C26 C25 H25B 109.8 . . ?
H25A C25 H25B 108.3 . . ?
C27 C26 C28 110.5(3) . . ?
C27 C26 C25 109.4(3) . . ?
C28 C26 C25 108.5(3) . . ?
C27 C26 H26A 109.5 . . ?
C28 C26 H26A 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C26 C27 C21 109.8(3) . . ?
C26 C27 H27A 109.7 . . ?
C21 C27 H27A 109.7 . . ?
C26 C27 H27B 109.7 . . ?
C21 C27 H27B 109.7 . . ?
H27A C27 H27B 108.2 . . ?
C26 C28 C23 110.3(3) . . ?
C26 C28 H28A 109.6 . . ?
C23 C28 H28A 109.6 . . ?
C26 C28 H28B 109.6 . . ?
C23 C28 H28B 109.6 . . ?
H28A C28 H28B 108.1 . . ?
C34 C29 C30 120.5(3) . . ?
C34 C29 S2 120.2(2) . . ?
C30 C29 S2 119.3(2) . . ?
C31 C30 C29 120.3(3) . . ?
C31 C30 H30A 119.9 . . ?
C29 C30 H30A 119.9 . . ?
C30 C31 C32 119.4(3) . . ?
C30 C31 H31A 120.3 . . ?
C32 C31 H31A 120.3 . . ?
C33 C32 N4 116.7(3) . . ?
C33 C32 C31 119.5(3) . . ?
N4 C32 C31 123.7(3) . . ?
C34 C33 C32 120.4(3) . . ?
C34 C33 H33A 119.8 . . ?
C32 C33 H33A 119.8 . . ?
C29 C34 C33 119.8(3) . . ?
C29 C34 H34A 120.1 . . ?
C33 C34 H34A 120.1 . . ?
O6 C35 N4 123.7(3) . . ?
O6 C35 C36 121.9(3) . . ?
N4 C35 C36 114.3(3) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
H5 O7 H6 109(4) . . ?
H7 O8 H8 114(5) . . ?
H9 O9 H10 104(4) . . ?
H11 O10 H12 117(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
O2 S1 N1 C1 -170.0(2) . . . . ?
O1 S1 N1 C1 -41.2(3) . . . . ?
C11 S1 N1 C1 75.0(3) . . . . ?
O5 S2 N3 C19 42.2(3) . . . . ?
O4 S2 N3 C19 170.4(2) . . . . ?
C29 S2 N3 C19 -74.4(3) . . . . ?
S1 N1 C1 C2 -44.5(4) . . . . ?
S1 N1 C1 C6 -164.0(2) . . . . ?
S1 N1 C1 C9 78.9(3) . . . . ?
N1 C1 C2 C3 -177.8(3) . . . . ?
C6 C1 C2 C3 -59.9(4) . . . . ?
C9 C1 C2 C3 58.9(4) . . . . ?
C1 C2 C3 C10 -60.1(4) . . . . ?
C1 C2 C3 C4 60.7(4) . . . . ?
C10 C3 C4 C5 59.3(4) . . . . ?
C2 C3 C4 C5 -60.9(4) . . . . ?
C3 C4 C5 C7 -59.5(4) . . . . ?
C3 C4 C5 C6 60.3(4) . . . . ?
N1 C1 C6 C5 -178.1(3) . . . . ?
C2 C1 C6 C5 59.9(3) . . . . ?
C9 C1 C6 C5 -59.9(3) . . . . ?
C4 C5 C6 C1 -60.1(4) . . . . ?
C7 C5 C6 C1 59.7(4) . . . . ?
C4 C5 C7 C8 60.2(4) . . . . ?
C6 C5 C7 C8 -59.3(4) . . . . ?
C5 C7 C8 C10 -59.9(4) . . . . ?
C5 C7 C8 C9 60.0(4) . . . . ?
N1 C1 C9 C8 176.2(3) . . . . ?
C2 C1 C9 C8 -58.7(4) . . . . ?
C6 C1 C9 C8 60.5(4) . . . . ?
C7 C8 C9 C1 -61.1(4) . . . . ?
C10 C8 C9 C1 59.2(4) . . . . ?
C4 C3 C10 C8 -58.8(4) . . . . ?
C2 C3 C10 C8 61.2(4) . . . . ?
C7 C8 C10 C3 59.2(4) . . . . ?
C9 C8 C10 C3 -60.7(4) . . . . ?
O2 S1 C11 C12 123.7(3) . . . . ?
O1 S1 C11 C12 -4.3(3) . . . . ?
N1 S1 C11 C12 -122.0(3) . . . . ?
O2 S1 C11 C16 -55.3(3) . . . . ?
O1 S1 C11 C16 176.7(2) . . . . ?
N1 S1 C11 C16 59.0(3) . . . . ?
C16 C11 C12 C13 -0.6(5) . . . . ?
S1 C11 C12 C13 -179.6(3) . . . . ?
C11 C12 C13 C14 -1.1(5) . . . . ?
C12 C13 C14 C15 2.4(5) . . . . ?
C12 C13 C14 N2 -179.4(3) . . . . ?
C17 N2 C14 C13 169.4(3) . . . . ?
C17 N2 C14 C15 -12.5(5) . . . . ?
C13 C14 C15 C16 -2.0(5) . . . . ?
N2 C14 C15 C16 179.9(3) . . . . ?
C14 C15 C16 C11 0.4(5) . . . . ?
C12 C11 C16 C15 0.9(5) . . . . ?
S1 C11 C16 C15 179.9(2) . . . . ?
C14 N2 C17 O3 2.2(5) . . . . ?
C14 N2 C17 C18 -176.7(3) . . . . ?
S2 N3 C19 C24 46.0(4) . . . . ?
S2 N3 C19 C20 166.2(2) . . . . ?
S2 N3 C19 C25 -77.1(3) . . . . ?
N3 C19 C20 C21 178.4(3) . . . . ?
C24 C19 C20 C21 -59.2(4) . . . . ?
C25 C19 C20 C21 60.7(4) . . . . ?
C19 C20 C21 C22 59.3(4) . . . . ?
C19 C20 C21 C27 -60.7(4) . . . . ?
C27 C21 C22 C23 58.4(4) . . . . ?
C20 C21 C22 C23 -60.5(4) . . . . ?
C21 C22 C23 C28 -57.7(4) . . . . ?
C21 C22 C23 C24 61.0(4) . . . . ?
N3 C19 C24 C23 177.4(3) . . . . ?
C20 C19 C24 C23 59.3(4) . . . . ?
C25 C19 C24 C23 -59.6(4) . . . . ?
C22 C23 C24 C19 -60.0(4) . . . . ?
C28 C23 C24 C19 59.7(4) . . . . ?
N3 C19 C25 C26 -175.4(3) . . . . ?
C24 C19 C25 C26 59.7(4) . . . . ?
C20 C19 C25 C26 -60.1(4) . . . . ?
C19 C25 C26 C27 60.7(4) . . . . ?
C19 C25 C26 C28 -59.9(4) . . . . ?
C28 C26 C27 C21 58.6(4) . . . . ?
C25 C26 C27 C21 -60.8(4) . . . . ?
C22 C21 C27 C26 -58.6(4) . . . . ?
C20 C21 C27 C26 60.4(4) . . . . ?
C27 C26 C28 C23 -58.4(4) . . . . ?
C25 C26 C28 C23 61.5(4) . . . . ?
C22 C23 C28 C26 57.7(4) . . . . ?
C24 C23 C28 C26 -61.3(4) . . . . ?
O5 S2 C29 C34 11.3(3) . . . . ?
O4 S2 C29 C34 -116.4(3) . . . . ?
N3 S2 C29 C34 129.7(3) . . . . ?
O5 S2 C29 C30 -170.6(3) . . . . ?
O4 S2 C29 C30 61.7(3) . . . . ?
N3 S2 C29 C30 -52.3(3) . . . . ?
C34 C29 C30 C31 -1.6(5) . . . . ?
S2 C29 C30 C31 -179.7(2) . . . . ?
C29 C30 C31 C32 0.1(5) . . . . ?
C35 N4 C32 C33 -166.8(3) . . . . ?
C35 N4 C32 C31 14.7(5) . . . . ?
C30 C31 C32 C33 1.8(5) . . . . ?
C30 C31 C32 N4 -179.8(3) . . . . ?
N4 C32 C33 C34 179.2(3) . . . . ?
C31 C32 C33 C34 -2.2(5) . . . . ?
C30 C29 C34 C33 1.2(5) . . . . ?
S2 C29 C34 C33 179.2(3) . . . . ?
C32 C33 C34 C29 0.8(5) . . . . ?
C32 N4 C35 O6 -1.9(5) . . . . ?
C32 N4 C35 C36 175.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9B O1 0.99 2.53 3.176(4) 122.8 .
C13 H13A O3 0.95 2.54 3.395(4) 149 1_565
C13 H13A O8 0.95 2.62 3.373(4) 136.7 .
C15 H15A O3 0.95 2.32 2.906(4) 119.2 .
C18 H18A O8 0.98 2.67 3.473(4) 139.1 .
C25 H25A O5 0.99 2.53 3.170(4) 122.2 .
C31 H31A O6 0.95 2.29 2.875(4) 118.7 .
C33 H33A O6 0.95 2.65 3.515(4) 151.2 1_565
C36 H36A O10 0.98 2.55 3.405(4) 145.5 .
N1 H1 O7 0.84(4) 1.98(4) 2.819(3) 170(4) 1_545
N2 H2 O8 0.83(4) 1.99(4) 2.806(4) 168(3) .
N3 H3 O9 0.90(4) 1.97(4) 2.873(3) 178(4) .
N4 H4 O10 0.80(4) 2.01(4) 2.811(4) 175(4) .
O7 H5 O4 0.76(5) 2.02(5) 2.746(3) 159(4) 1_655
O7 H6 O1 0.86(4) 1.90(4) 2.737(3) 162(4) .
O8 H7 O3 0.78(5) 1.99(5) 2.771(4) 175(5) 1_565
O8 H8 O7 0.80(5) 2.00(5) 2.792(4) 168(4) 2_565
O9 H9 S2 0.89(5) 2.91(5) 3.751(2) 159(3) 1_545
O9 H9 O5 0.89(5) 1.92(5) 2.799(3) 168(4) 1_545
O9 H10 O2 0.85(5) 1.98(5) 2.805(3) 163(4) 1_455
O10 H11 O6 0.85(4) 1.88(4) 2.731(3) 179(4) 1_565
O10 H12 O9 0.87(4) 1.96(4) 2.833(3) 172(4) 2_565

####################################################################### 
# 
# 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_19_298K
_database_code_depnum_ccdc_archive 'CCDC 1962772'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2019-10-31 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;

_audit_creation_date             2017-08-12T15:36:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C20 H28 N2 O3 S'
_chemical_formula_sum            'C20 H28 N2 O3 S'
_chemical_formula_weight         376.5

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.5823(13)
_cell_length_b                   15.6900(10)
_cell_length_c                   14.2997(10)
_cell_angle_alpha                90
_cell_angle_beta                 114.189(2)
_cell_angle_gamma                90
_cell_volume                     4007.8(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6147
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      24.89

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.26
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1616

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

_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.6653
_exptl_absorpt_correction_T_max  0.746

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

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_number            27687
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         30.049
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             5869
_reflns_number_gt                4187
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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)+(0.0800P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5869
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1607
_refine_ls_wR_factor_gt          0.1439
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.135
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.049

#----------------------------------------------------------------------------#
#                   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 0.11618(2) 0.12214(2) 0.65390(3) 0.03554(13) Uani 1 1 d . . . . .
O1 O 0.18319(7) 0.12563(8) 0.74750(9) 0.0476(3) Uani 1 1 d . . . . .
O2 O 0.06243(8) 0.05709(8) 0.64418(10) 0.0503(3) Uani 1 1 d . . . . .
O3 O 0.31099(8) 0.15680(9) 0.35022(11) 0.0552(4) Uani 1 1 d . . . . .
N1 N 0.07783(7) 0.21465(8) 0.64266(10) 0.0337(3) Uani 1 1 d . . . . .
H1A H 0.104411 0.25386 0.683337 0.04 Uiso 1 1 calc R U . . .
N2 N 0.23155(8) 0.04812(9) 0.33729(11) 0.0418(3) Uani 1 1 d . . . . .
H2C H 0.214002 0.001401 0.3049 0.05 Uiso 1 1 calc R U . . .
C1 C 0.00128(8) 0.23916(10) 0.56923(13) 0.0370(3) Uani 1 1 d . . . . .
C2 C -0.01040(11) 0.22946(16) 0.45806(15) 0.0617(6) Uani 1 1 d . . . . .
H2A H -0.004738 0.170049 0.443843 0.074 Uiso 1 1 calc R U . . .
H2B H 0.027203 0.262181 0.445909 0.074 Uiso 1 1 calc R U . . .
C3 C -0.08882(14) 0.2607(2) 0.38610(19) 0.0861(9) Uani 1 1 d . . . . .
C4 C -0.09544(13) 0.35525(18) 0.41052(19) 0.0770(7) Uani 1 1 d . . . . .
H4A H -0.058033 0.38818 0.39815 0.092 Uiso 1 1 calc R U . . .
H4B H -0.144397 0.3765 0.36524 0.092 Uiso 1 1 calc R U . . .
C5 C -0.08456(11) 0.36706(13) 0.52161(18) 0.0571(5) Uani 1 1 d . . . . .
C6 C -0.00670(10) 0.33304(11) 0.59108(15) 0.0433(4) Uani 1 1 d . . . . .
H6A H 0.031206 0.366044 0.579976 0.052 Uiso 1 1 calc R U . . .
H6B H 0.001289 0.339673 0.662259 0.052 Uiso 1 1 calc R U . . .
C7 C -0.05818(11) 0.18865(15) 0.5897(2) 0.0669(6) Uani 1 1 d . . . . .
H7A H -0.050798 0.195617 0.660568 0.08 Uiso 1 1 calc R U . . .
H7B H -0.054125 0.128504 0.57709 0.08 Uiso 1 1 calc R U . . .
C8 C -0.13575(12) 0.22195(18) 0.5181(3) 0.0891(10) Uani 1 1 d . . . . .
H8A H -0.173841 0.189239 0.530569 0.107 Uiso 1 1 calc R U . . .
C9 C -0.14743(14) 0.2097(2) 0.4095(3) 0.1120(13) Uani 1 1 d . . . . .
H9A H -0.197324 0.228589 0.364515 0.134 Uiso 1 1 calc R U . . .
H9B H -0.143277 0.149652 0.396583 0.134 Uiso 1 1 calc R U . . .
C10 C -0.14277(12) 0.31476(18) 0.5413(2) 0.0790(8) Uani 1 1 d . . . . .
H10A H -0.135325 0.320916 0.612372 0.095 Uiso 1 1 calc R U . . .
H10B H -0.192552 0.335247 0.498275 0.095 Uiso 1 1 calc R U . . .
C11 C -0.0982(2) 0.2511(3) 0.2747(2) 0.174(2) Uani 1 1 d . . . . .
H11A H -0.147141 0.270484 0.229248 0.261 Uiso 1 1 calc R U . . .
H11B H -0.060918 0.284485 0.264152 0.261 Uiso 1 1 calc R U . . .
H11C H -0.092576 0.192233 0.260844 0.261 Uiso 1 1 calc R U . . .
C12 C -0.09019(17) 0.46123(16) 0.5476(3) 0.0938(10) Uani 1 1 d . . . . .
H12A H -0.053357 0.493887 0.535058 0.141 Uiso 1 1 calc R U . . .
H12B H -0.139241 0.48241 0.505574 0.141 Uiso 1 1 calc R U . . .
H12C H -0.081476 0.466131 0.618564 0.141 Uiso 1 1 calc R U . . .
C13 C 0.14690(9) 0.10560(10) 0.55496(12) 0.0332(3) Uani 1 1 d . . . . .
C14 C 0.21021(9) 0.14807(11) 0.55903(13) 0.0407(4) Uani 1 1 d . . . . .
H14A H 0.233532 0.187921 0.610436 0.049 Uiso 1 1 calc R U . . .
C15 C 0.23879(10) 0.13151(11) 0.48720(14) 0.0422(4) Uani 1 1 d . . . . .
H15A H 0.281078 0.160352 0.490025 0.051 Uiso 1 1 calc R U . . .
C16 C 0.20424(9) 0.07172(10) 0.41078(12) 0.0358(3) Uani 1 1 d . . . . .
C17 C 0.13985(11) 0.03034(12) 0.40610(15) 0.0468(4) Uani 1 1 d . . . . .
H17A H 0.115911 -0.008808 0.354063 0.056 Uiso 1 1 calc R U . . .
C18 C 0.11134(10) 0.04694(11) 0.47790(14) 0.0442(4) Uani 1 1 d . . . . .
H18A H 0.068544 0.01893 0.474566 0.053 Uiso 1 1 calc R U . . .
C19 C 0.28195(9) 0.08963(11) 0.31107(13) 0.0397(4) Uani 1 1 d . . . . .
C20 C 0.29937(12) 0.04710(13) 0.22994(16) 0.0549(5) Uani 1 1 d . . . . .
H20A H 0.271056 -0.004708 0.209053 0.082 Uiso 1 1 calc R U . . .
H20B H 0.286376 0.084449 0.172014 0.082 Uiso 1 1 calc R U . . .
H20C H 0.351859 0.034229 0.256624 0.082 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 O2 1.4314(13) . ?
S1 O1 1.4411(13) . ?
S1 N1 1.6117(13) . ?
S1 C13 1.7688(16) . ?
O3 C19 1.219(2) . ?
N1 C1 1.486(2) . ?
N1 H1A 0.86 . ?
N2 C19 1.357(2) . ?
N2 C16 1.410(2) . ?
N2 H2C 0.86 . ?
C1 C2 1.518(3) . ?
C1 C6 1.527(2) . ?
C1 C7 1.532(2) . ?
C2 C3 1.537(3) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 C11 1.535(4) . ?
C3 C4 1.542(4) . ?
C3 C9 1.544(5) . ?
C4 C5 1.525(4) . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C5 C10 1.522(3) . ?
C5 C6 1.535(3) . ?
C5 C12 1.539(3) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.534(3) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.487(5) . ?
C8 C10 1.512(4) . ?
C8 H8A 0.98 . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 H11A 0.96 . ?
C11 H11B 0.96 . ?
C11 H11C 0.96 . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 C18 1.385(2) . ?
C13 C14 1.388(2) . ?
C14 C15 1.381(2) . ?
C14 H14A 0.93 . ?
C15 C16 1.388(2) . ?
C15 H15A 0.93 . ?
C16 C17 1.395(2) . ?
C17 C18 1.380(2) . ?
C17 H17A 0.93 . ?
C18 H18A 0.93 . ?
C19 C20 1.494(2) . ?
C20 H20A 0.96 . ?
C20 H20B 0.96 . ?
C20 H20C 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
O2 S1 O1 118.08(8) . . ?
O2 S1 N1 109.79(8) . . ?
O1 S1 N1 105.56(7) . . ?
O2 S1 C13 107.17(8) . . ?
O1 S1 C13 105.65(8) . . ?
N1 S1 C13 110.46(7) . . ?
C1 N1 S1 126.69(11) . . ?
C1 N1 H1A 116.7 . . ?
S1 N1 H1A 116.7 . . ?
C19 N2 C16 128.38(14) . . ?
C19 N2 H2C 115.8 . . ?
C16 N2 H2C 115.8 . . ?
N1 C1 C2 112.93(14) . . ?
N1 C1 C6 105.27(13) . . ?
C2 C1 C6 109.08(15) . . ?
N1 C1 C7 110.91(14) . . ?
C2 C1 C7 110.33(17) . . ?
C6 C1 C7 108.09(15) . . ?
C1 C2 C3 110.46(18) . . ?
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 . . ?
C11 C3 C2 109.0(2) . . ?
C11 C3 C4 110.1(3) . . ?
C2 C3 C4 108.0(2) . . ?
C11 C3 C9 113.0(3) . . ?
C2 C3 C9 108.5(2) . . ?
C4 C3 C9 108.1(2) . . ?
C5 C4 C3 111.3(2) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108 . . ?
C10 C5 C4 109.4(2) . . ?
C10 C5 C6 108.26(18) . . ?
C4 C5 C6 108.04(17) . . ?
C10 C5 C12 109.8(2) . . ?
C4 C5 C12 112.1(2) . . ?
C6 C5 C12 109.15(19) . . ?
C1 C6 C5 111.16(15) . . ?
C1 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C1 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108 . . ?
C1 C7 C8 108.59(19) . . ?
C1 C7 H7A 110 . . ?
C8 C7 H7A 110 . . ?
C1 C7 H7B 110 . . ?
C8 C7 H7B 110 . . ?
H7A C7 H7B 108.4 . . ?
C9 C8 C10 111.4(3) . . ?
C9 C8 C7 109.8(2) . . ?
C10 C8 C7 109.6(2) . . ?
C9 C8 H8A 108.6 . . ?
C10 C8 H8A 108.6 . . ?
C7 C8 H8A 108.6 . . ?
C8 C9 C3 110.5(2) . . ?
C8 C9 H9A 109.6 . . ?
C3 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C3 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C8 C10 C5 109.6(2) . . ?
C8 C10 H10A 109.7 . . ?
C5 C10 H10A 109.7 . . ?
C8 C10 H10B 109.7 . . ?
C5 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 120.13(15) . . ?
C18 C13 S1 120.61(12) . . ?
C14 C13 S1 119.13(12) . . ?
C15 C14 C13 120.39(15) . . ?
C15 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
C14 C15 C16 119.83(15) . . ?
C14 C15 H15A 120.1 . . ?
C16 C15 H15A 120.1 . . ?
C15 C16 C17 119.45(16) . . ?
C15 C16 N2 123.57(15) . . ?
C17 C16 N2 116.96(14) . . ?
C18 C17 C16 120.65(15) . . ?
C18 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
C17 C18 C13 119.52(15) . . ?
C17 C18 H18A 120.2 . . ?
C13 C18 H18A 120.2 . . ?
O3 C19 N2 122.89(16) . . ?
O3 C19 C20 122.05(16) . . ?
N2 C19 C20 115.06(15) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O2 S1 N1 C1 -40.34(15) . . . . ?
O1 S1 N1 C1 -168.61(13) . . . . ?
C13 S1 N1 C1 77.64(14) . . . . ?
S1 N1 C1 C2 -61.32(19) . . . . ?
S1 N1 C1 C6 179.78(12) . . . . ?
S1 N1 C1 C7 63.1(2) . . . . ?
N1 C1 C2 C3 -176.65(19) . . . . ?
C6 C1 C2 C3 -60.0(2) . . . . ?
C7 C1 C2 C3 58.6(2) . . . . ?
C1 C2 C3 C11 179.2(3) . . . . ?
C1 C2 C3 C4 59.6(3) . . . . ?
C1 C2 C3 C9 -57.4(3) . . . . ?
C11 C3 C4 C5 -178.7(2) . . . . ?
C2 C3 C4 C5 -59.8(3) . . . . ?
C9 C3 C4 C5 57.4(3) . . . . ?
C3 C4 C5 C10 -58.5(2) . . . . ?
C3 C4 C5 C6 59.1(3) . . . . ?
C3 C4 C5 C12 179.4(2) . . . . ?
N1 C1 C6 C5 -178.84(15) . . . . ?
C2 C1 C6 C5 59.7(2) . . . . ?
C7 C1 C6 C5 -60.3(2) . . . . ?
C10 C5 C6 C1 59.6(2) . . . . ?
C4 C5 C6 C1 -58.8(2) . . . . ?
C12 C5 C6 C1 179.14(19) . . . . ?
N1 C1 C7 C8 175.1(2) . . . . ?
C2 C1 C7 C8 -59.0(3) . . . . ?
C6 C1 C7 C8 60.2(3) . . . . ?
C1 C7 C8 C9 60.7(3) . . . . ?
C1 C7 C8 C10 -62.0(3) . . . . ?
C10 C8 C9 C3 60.0(3) . . . . ?
C7 C8 C9 C3 -61.6(3) . . . . ?
C11 C3 C9 C8 -179.7(3) . . . . ?
C2 C3 C9 C8 59.4(3) . . . . ?
C4 C3 C9 C8 -57.5(3) . . . . ?
C9 C8 C10 C5 -59.8(3) . . . . ?
C7 C8 C10 C5 61.9(3) . . . . ?
C4 C5 C10 C8 58.0(3) . . . . ?
C6 C5 C10 C8 -59.5(3) . . . . ?
C12 C5 C10 C8 -178.6(2) . . . . ?
O2 S1 C13 C18 9.30(17) . . . . ?
O1 S1 C13 C18 136.04(15) . . . . ?
N1 S1 C13 C18 -110.27(15) . . . . ?
O2 S1 C13 C14 -166.52(13) . . . . ?
O1 S1 C13 C14 -39.78(15) . . . . ?
N1 S1 C13 C14 73.91(15) . . . . ?
C18 C13 C14 C15 -0.8(3) . . . . ?
S1 C13 C14 C15 175.05(14) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C14 C15 C16 C17 1.4(3) . . . . ?
C14 C15 C16 N2 -177.04(16) . . . . ?
C19 N2 C16 C15 -16.9(3) . . . . ?
C19 N2 C16 C17 164.62(18) . . . . ?
C15 C16 C17 C18 -1.5(3) . . . . ?
N2 C16 C17 C18 177.13(17) . . . . ?
C16 C17 C18 C13 0.3(3) . . . . ?
C14 C13 C18 C17 0.8(3) . . . . ?
S1 C13 C18 C17 -174.99(15) . . . . ?
C16 N2 C19 O3 -0.5(3) . . . . ?
C16 N2 C19 C20 179.71(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O3 0.86 2.36 2.9388(18) 124.5 7_556
N2 H2C S1 0.86 2.95 3.7766(14) 162 6
N2 H2C O1 0.86 2.15 2.9968(18) 170.2 6
C7 H7B O2 0.97 2.36 2.990(3) 121.6 .
C15 H15A O3 0.93 2.3 2.875(2) 119.3 .

####################################################################### 
# 
# 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_24
_database_code_depnum_ccdc_archive 'CCDC 1962778'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2019-10-31 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;

_audit_creation_date             2017-04-02T23:54:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C21 H31 N O2 S'
_chemical_formula_sum            'C21 H31 N O2 S'
_chemical_formula_weight         361.53

#----------------------------------------------------------------------------#
#                   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                   10.5236(3)
_cell_length_b                   13.9711(4)
_cell_length_c                   14.1761(4)
_cell_angle_alpha                78.4410(10)
_cell_angle_beta                 85.2520(10)
_cell_angle_gamma                73.4320(10)
_cell_volume                     1956.48(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7143
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      30.68

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             784

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

_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.6387
_exptl_absorpt_correction_T_max  0.7462

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

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_number            28355
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.181
_diffrn_reflns_theta_max         31.019
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.96
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.96
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.96
_reflns_Friedel_coverage         0
_reflns_number_total             12002
_reflns_number_gt                9092
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   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)+(0.0740P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         12002
_refine_ls_number_parameters     699
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1265
_refine_ls_wR_factor_gt          0.1152
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.063

#----------------------------------------------------------------------------#
#                   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 0.11314(3) 0.31701(2) 0.35432(2) 0.01415(8) Uani 1 1 d . . . . .
S2 S -0.13777(3) 0.80794(2) 0.30995(2) 0.01436(8) Uani 1 1 d . . . . .
N1 N 0.24314(11) 0.23613(9) 0.40280(8) 0.0159(2) Uani 1 1 d . . . . .
N2 N 0.00041(11) 0.74564(9) 0.35931(8) 0.0177(2) Uani 1 1 d . . . . .
O1 O 0.01301(9) 0.32717(7) 0.43068(7) 0.0194(2) Uani 1 1 d . . . . .
O2 O 0.14347(9) 0.40775(7) 0.30326(7) 0.0192(2) Uani 1 1 d . . . . .
O3 O -0.23347(9) 0.82600(7) 0.38811(7) 0.0193(2) Uani 1 1 d . . . . .
O4 O -0.11761(9) 0.89393(7) 0.24228(7) 0.0199(2) Uani 1 1 d . . . . .
C1 C 0.38080(12) 0.21583(9) 0.36264(9) 0.0135(2) Uani 1 1 d . . . . .
C2 C 0.44693(13) 0.29534(10) 0.37921(10) 0.0171(3) Uani 1 1 d . . . . .
C3 C 0.59172(13) 0.27043(10) 0.34207(10) 0.0192(3) Uani 1 1 d . . . . .
C4 C 0.66640(14) 0.16468(11) 0.39579(11) 0.0209(3) Uani 1 1 d . . . . .
C5 C 0.60105(14) 0.08475(10) 0.37975(10) 0.0197(3) Uani 1 1 d . . . . .
C6 C 0.45665(13) 0.11118(10) 0.41661(10) 0.0176(3) Uani 1 1 d . . . . .
C7 C 0.38504(13) 0.21281(11) 0.25485(9) 0.0176(3) Uani 1 1 d . . . . .
C8 C 0.52909(13) 0.18674(11) 0.21630(10) 0.0206(3) Uani 1 1 d . . . . .
C9 C 0.60491(14) 0.08245(11) 0.27186(11) 0.0222(3) Uani 1 1 d . . . . .
C10 C 0.59380(14) 0.26686(11) 0.23432(11) 0.0221(3) Uani 1 1 d . . . . .
C11 C 0.65634(17) 0.35020(13) 0.35791(15) 0.0314(4) Uani 1 1 d . . . . .
C12 C 0.53094(18) 0.18486(16) 0.10860(12) 0.0341(4) Uani 1 1 d . . . . .
C13 C 0.06234(12) 0.25633(9) 0.27049(9) 0.0140(2) Uani 1 1 d . . . . .
C14 C 0.05130(12) 0.29940(10) 0.17147(9) 0.0158(2) Uani 1 1 d . . . . .
C15 C 0.01505(14) 0.24452(11) 0.11075(10) 0.0191(3) Uani 1 1 d . . . . .
C16 C -0.01183(13) 0.15168(11) 0.14415(10) 0.0196(3) Uani 1 1 d . . . . .
C17 C -0.00250(13) 0.11246(10) 0.24229(10) 0.0197(3) Uani 1 1 d . . . . .
C18 C 0.03461(13) 0.16216(10) 0.30676(10) 0.0171(3) Uani 1 1 d . . . . .
C19 C 0.07657(15) 0.39961(11) 0.12394(10) 0.0211(3) Uani 1 1 d . . . . .
C20 C -0.04751(19) 0.09281(14) 0.07732(12) 0.0294(3) Uani 1 1 d . . . . .
C21 C 0.04310(17) 0.10971(12) 0.41121(11) 0.0247(3) Uani 1 1 d . . . . .
C22 C 0.13479(12) 0.72724(10) 0.31311(9) 0.0165(2) Uani 1 1 d . . . . .
C23 C 0.18526(15) 0.82138(12) 0.30057(13) 0.0264(3) Uani 1 1 d . . . . .
C24 C 0.32868(15) 0.80018(13) 0.25962(13) 0.0310(4) Uani 1 1 d . . . . .
C25 C 0.41716(16) 0.71195(16) 0.32904(14) 0.0387(4) Uani 1 1 d . . . . .
C26 C 0.36743(15) 0.61728(14) 0.34137(12) 0.0324(4) Uani 1 1 d . . . . .
C27 C 0.22402(15) 0.63904(13) 0.38170(11) 0.0273(3) Uani 1 1 d . . . . .
C28 C 0.13912(13) 0.69514(10) 0.21518(10) 0.0169(2) Uani 1 1 d . . . . .
C29 C 0.28214(13) 0.67212(10) 0.17315(10) 0.0188(3) Uani 1 1 d . . . . .
C30 C 0.37084(15) 0.58638(12) 0.24364(11) 0.0262(3) Uani 1 1 d . . . . .
C31 C 0.33050(15) 0.76747(12) 0.16218(11) 0.0244(3) Uani 1 1 d . . . . .
C32 C 0.3767(2) 0.8948(2) 0.2480(2) 0.0580(7) Uani 1 1 d . . . . .
C33 C 0.28512(18) 0.63962(15) 0.07620(12) 0.0317(4) Uani 1 1 d . . . . .
C34 C -0.18693(12) 0.72789(10) 0.24485(9) 0.0153(2) Uani 1 1 d . . . . .
C35 C -0.18371(13) 0.62804(10) 0.29219(10) 0.0180(3) Uani 1 1 d . . . . .
C36 C -0.21487(14) 0.56389(11) 0.23981(11) 0.0211(3) Uani 1 1 d . . . . .
C37 C -0.25332(14) 0.59548(11) 0.14456(11) 0.0221(3) Uani 1 1 d . . . . .
C38 C -0.26206(14) 0.69551(12) 0.10158(11) 0.0225(3) Uani 1 1 d . . . . .
C39 C -0.23035(13) 0.76393(10) 0.14933(10) 0.0183(3) Uani 1 1 d . . . . .
C40 C -0.15008(18) 0.58503(12) 0.39651(11) 0.0255(3) Uani 1 1 d . . . . .
C41 C -0.28470(18) 0.52334(14) 0.08992(13) 0.0301(4) Uani 1 1 d . . . . .
C42 C -0.24913(19) 0.87115(12) 0.09401(11) 0.0292(3) Uani 1 1 d . . . . .
H1 H 0.2372(18) 0.2191(13) 0.4589(13) 0.027(5) Uiso 1 1 d . . . . .
H2 H -0.003(2) 0.7189(15) 0.4162(15) 0.041(6) Uiso 1 1 d . . . . .
H3 H 0.4438(16) 0.2960(12) 0.4490(12) 0.019(4) Uiso 1 1 d . . . . .
H4 H 0.3945(15) 0.3637(12) 0.3455(11) 0.021(4) Uiso 1 1 d . . . . .
H5 H 0.7567(17) 0.1479(12) 0.3718(12) 0.025(4) Uiso 1 1 d . . . . .
H6 H 0.6630(17) 0.1665(12) 0.4659(13) 0.027(4) Uiso 1 1 d . . . . .
H7 H 0.6476(16) 0.0218(12) 0.4150(11) 0.021(4) Uiso 1 1 d . . . . .
H8 H 0.4106(15) 0.0606(12) 0.4038(12) 0.022(4) Uiso 1 1 d . . . . .
H9 H 0.4527(17) 0.1128(12) 0.4808(12) 0.025(4) Uiso 1 1 d . . . . .
H10 H 0.3391(17) 0.1619(13) 0.2456(12) 0.028(4) Uiso 1 1 d . . . . .
H11 H 0.3355(15) 0.2806(12) 0.2177(11) 0.019(4) Uiso 1 1 d . . . . .
H12 H 0.5633(17) 0.0288(13) 0.2597(12) 0.029(5) Uiso 1 1 d . . . . .
H13 H 0.6977(18) 0.0671(13) 0.2455(13) 0.031(5) Uiso 1 1 d . . . . .
H14 H 0.5440(16) 0.3362(12) 0.1988(12) 0.023(4) Uiso 1 1 d . . . . .
H15 H 0.6873(18) 0.2560(13) 0.2104(13) 0.030(5) Uiso 1 1 d . . . . .
H16 H 0.652(2) 0.3550(15) 0.4254(16) 0.049(6) Uiso 1 1 d . . . . .
H17 H 0.6122(18) 0.4198(14) 0.3220(13) 0.033(5) Uiso 1 1 d . . . . .
H18 H 0.752(2) 0.3306(14) 0.3403(13) 0.038(5) Uiso 1 1 d . . . . .
H19 H 0.488(2) 0.1333(15) 0.0976(14) 0.043(6) Uiso 1 1 d . . . . .
H20 H 0.614(2) 0.1681(15) 0.0827(15) 0.045(6) Uiso 1 1 d . . . . .
H21 H 0.483(2) 0.2526(16) 0.0748(15) 0.048(6) Uiso 1 1 d . . . . .
H22 H 0.0068(16) 0.2735(12) 0.0447(12) 0.023(4) Uiso 1 1 d . . . . .
H23 H -0.0224(16) 0.0487(12) 0.2695(12) 0.022(4) Uiso 1 1 d . . . . .
H24 H 0.0175(16) 0.4564(12) 0.1520(11) 0.021(4) Uiso 1 1 d . . . . .
H25 H 0.0554(16) 0.4137(12) 0.0524(12) 0.022(4) Uiso 1 1 d . . . . .
H26 H 0.1672(18) 0.3989(12) 0.1289(12) 0.027(4) Uiso 1 1 d . . . . .
H27 H -0.124(2) 0.0740(17) 0.0947(17) 0.062(7) Uiso 1 1 d . . . . .
H28 H 0.031(2) 0.0316(18) 0.0737(17) 0.076(8) Uiso 1 1 d . . . . .
H29 H -0.064(2) 0.1338(15) 0.0152(15) 0.042(5) Uiso 1 1 d . . . . .
H30 H 0.012(2) 0.0489(15) 0.4166(14) 0.044(6) Uiso 1 1 d . . . . .
H31 H -0.0074(19) 0.1520(14) 0.4551(14) 0.041(5) Uiso 1 1 d . . . . .
H32 H 0.133(2) 0.0864(14) 0.4351(14) 0.038(5) Uiso 1 1 d . . . . .
H33 H 0.183(2) 0.8402(15) 0.3648(15) 0.045(6) Uiso 1 1 d . . . . .
H34 H 0.1318(18) 0.8773(14) 0.2586(13) 0.033(5) Uiso 1 1 d . . . . .
H35 H 0.508(2) 0.6985(15) 0.3037(14) 0.043(5) Uiso 1 1 d . . . . .
H36 H 0.4147(19) 0.7309(14) 0.3942(14) 0.039(5) Uiso 1 1 d . . . . .
H37 H 0.4270(19) 0.5614(14) 0.3863(14) 0.043(5) Uiso 1 1 d . . . . .
H38 H 0.1920(18) 0.5770(14) 0.3915(13) 0.035(5) Uiso 1 1 d . . . . .
H39 H 0.2190(19) 0.6599(14) 0.4411(14) 0.041(5) Uiso 1 1 d . . . . .
H40 H 0.0733(16) 0.7521(12) 0.1698(11) 0.021(4) Uiso 1 1 d . . . . .
H41 H 0.1030(16) 0.6359(13) 0.2241(12) 0.026(4) Uiso 1 1 d . . . . .
H42 H 0.3423(19) 0.5237(15) 0.2499(14) 0.042(5) Uiso 1 1 d . . . . .
H43 H 0.4618(19) 0.5719(14) 0.2200(13) 0.035(5) Uiso 1 1 d . . . . .
H44 H 0.2714(19) 0.8258(14) 0.1133(14) 0.040(5) Uiso 1 1 d . . . . .
H45 H 0.4208(18) 0.7576(13) 0.1323(13) 0.032(5) Uiso 1 1 d . . . . .
H46 H 0.324(2) 0.9508(18) 0.2052(18) 0.062(8) Uiso 1 1 d . . . . .
H47 H 0.464(2) 0.8840(17) 0.2220(17) 0.061(7) Uiso 1 1 d . . . . .
H48 H 0.377(2) 0.9141(19) 0.3120(19) 0.075(8) Uiso 1 1 d . . . . .
H49 H 0.375(2) 0.6198(15) 0.0495(15) 0.045(6) Uiso 1 1 d . . . . .
H50 H 0.234(2) 0.6944(16) 0.0264(15) 0.050(6) Uiso 1 1 d . . . . .
H51 H 0.251(2) 0.5824(15) 0.0852(15) 0.045(6) Uiso 1 1 d . . . . .
H52 H -0.2099(17) 0.5001(13) 0.2714(12) 0.028(5) Uiso 1 1 d . . . . .
H53 H -0.2953(17) 0.7199(13) 0.0338(13) 0.029(5) Uiso 1 1 d . . . . .
H54 H -0.1799(18) 0.5250(14) 0.4191(13) 0.033(5) Uiso 1 1 d . . . . .
H55 H -0.1866(18) 0.6343(13) 0.4381(13) 0.033(5) Uiso 1 1 d . . . . .
H56 H -0.057(2) 0.5644(14) 0.4084(14) 0.039(5) Uiso 1 1 d . . . . .
H57 H -0.332(2) 0.4853(19) 0.1255(18) 0.070(8) Uiso 1 1 d . . . . .
H58 H -0.206(2) 0.4787(16) 0.0668(16) 0.059(7) Uiso 1 1 d . . . . .
H59 H -0.343(3) 0.5572(19) 0.0349(19) 0.075(8) Uiso 1 1 d . . . . .
H60 H -0.3022(18) 0.9221(13) 0.1300(13) 0.030(5) Uiso 1 1 d . . . . .
H61 H -0.2917(19) 0.8811(14) 0.0330(14) 0.040(5) Uiso 1 1 d . . . . .
H62 H -0.166(2) 0.8860(15) 0.0785(14) 0.043(6) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 O2 1.4345(10) . ?
S1 O1 1.4456(10) . ?
S1 N1 1.6073(12) . ?
S1 C13 1.7844(13) . ?
S2 O4 1.4348(10) . ?
S2 O3 1.4450(10) . ?
S2 N2 1.6013(12) . ?
S2 C34 1.7868(13) . ?
N1 C1 1.4823(16) . ?
N1 H1 0.786(18) . ?
N2 C22 1.4839(16) . ?
N2 H2 0.82(2) . ?
C1 C2 1.5316(17) . ?
C1 C6 1.5322(17) . ?
C1 C7 1.5337(18) . ?
C2 C3 1.5356(19) . ?
C2 H3 0.988(16) . ?
C2 H4 1.002(16) . ?
C3 C11 1.521(2) . ?
C3 C10 1.536(2) . ?
C3 C4 1.5382(19) . ?
C4 C5 1.529(2) . ?
C4 H5 0.961(17) . ?
C4 H6 0.997(17) . ?
C5 C6 1.5311(19) . ?
C5 C9 1.533(2) . ?
C5 H7 0.939(16) . ?
C6 H8 1.014(16) . ?
C6 H9 0.912(17) . ?
C7 C8 1.5353(18) . ?
C7 H10 1.000(17) . ?
C7 H11 1.005(16) . ?
C8 C12 1.531(2) . ?
C8 C10 1.536(2) . ?
C8 C9 1.537(2) . ?
C9 H12 1.017(17) . ?
C9 H13 0.995(18) . ?
C10 H14 1.013(17) . ?
C10 H15 0.993(18) . ?
C11 H16 0.97(2) . ?
C11 H17 1.002(19) . ?
C11 H18 0.993(19) . ?
C12 H19 1.00(2) . ?
C12 H20 0.90(2) . ?
C12 H21 0.98(2) . ?
C13 C14 1.4123(17) . ?
C13 C18 1.4154(17) . ?
C14 C15 1.4000(18) . ?
C14 C19 1.5132(18) . ?
C15 C16 1.3884(19) . ?
C15 H22 0.943(16) . ?
C16 C17 1.390(2) . ?
C16 C20 1.5041(19) . ?
C17 C18 1.3922(19) . ?
C17 H23 0.970(16) . ?
C18 C21 1.5123(19) . ?
C19 H24 0.990(16) . ?
C19 H25 1.025(16) . ?
C19 H26 0.959(17) . ?
C20 H27 0.92(2) . ?
C20 H28 1.01(2) . ?
C20 H29 0.95(2) . ?
C21 H30 0.98(2) . ?
C21 H31 0.965(19) . ?
C21 H32 0.97(2) . ?
C22 C23 1.527(2) . ?
C22 C27 1.535(2) . ?
C22 C28 1.5356(18) . ?
C23 C24 1.540(2) . ?
C23 H33 0.99(2) . ?
C23 H34 0.948(18) . ?
C24 C32 1.520(2) . ?
C24 C31 1.537(2) . ?
C24 C25 1.538(3) . ?
C25 C26 1.530(3) . ?
C25 H35 0.97(2) . ?
C25 H36 1.006(19) . ?
C26 C30 1.526(2) . ?
C26 C27 1.537(2) . ?
C26 H37 1.00(2) . ?
C27 H38 0.998(18) . ?
C27 H39 0.937(19) . ?
C28 C29 1.5414(18) . ?
C28 H40 1.039(16) . ?
C28 H41 0.987(17) . ?
C29 C33 1.527(2) . ?
C29 C30 1.530(2) . ?
C29 C31 1.532(2) . ?
C30 H42 0.990(19) . ?
C30 H43 0.966(19) . ?
C31 H44 1.042(19) . ?
C31 H45 0.991(18) . ?
C32 H46 0.95(2) . ?
C32 H47 0.95(2) . ?
C32 H48 1.00(3) . ?
C33 H49 0.98(2) . ?
C33 H50 0.99(2) . ?
C33 H51 0.95(2) . ?
C34 C39 1.4121(18) . ?
C34 C35 1.4139(18) . ?
C35 C36 1.3918(18) . ?
C35 C40 1.511(2) . ?
C36 C37 1.390(2) . ?
C36 H52 0.902(17) . ?
C37 C38 1.388(2) . ?
C37 C41 1.507(2) . ?
C38 C39 1.4007(19) . ?
C38 H53 1.008(18) . ?
C39 C42 1.511(2) . ?
C40 H54 0.965(18) . ?
C40 H55 0.971(18) . ?
C40 H56 0.96(2) . ?
C41 H57 0.89(3) . ?
C41 H58 0.96(2) . ?
C41 H59 0.99(3) . ?
C42 H60 0.976(18) . ?
C42 H61 0.97(2) . ?
C42 H62 0.96(2) . ?

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
O2 S1 O1 117.63(6) . . ?
O2 S1 N1 111.02(6) . . ?
O1 S1 N1 105.63(6) . . ?
O2 S1 C13 109.01(6) . . ?
O1 S1 C13 107.42(6) . . ?
N1 S1 C13 105.40(6) . . ?
O4 S2 O3 118.38(6) . . ?
O4 S2 N2 108.54(6) . . ?
O3 S2 N2 105.98(6) . . ?
O4 S2 C34 108.07(6) . . ?
O3 S2 C34 107.24(6) . . ?
N2 S2 C34 108.27(6) . . ?
C1 N1 S1 127.23(9) . . ?
C1 N1 H1 114.8(13) . . ?
S1 N1 H1 114.9(13) . . ?
C22 N2 S2 127.47(9) . . ?
C22 N2 H2 115.3(14) . . ?
S2 N2 H2 117.2(14) . . ?
N1 C1 C2 111.10(10) . . ?
N1 C1 C6 106.48(10) . . ?
C2 C1 C6 109.03(11) . . ?
N1 C1 C7 111.46(10) . . ?
C2 C1 C7 109.86(11) . . ?
C6 C1 C7 108.79(11) . . ?
C1 C2 C3 110.65(10) . . ?
C1 C2 H3 108.7(9) . . ?
C3 C2 H3 109.7(9) . . ?
C1 C2 H4 108.2(9) . . ?
C3 C2 H4 111.1(9) . . ?
H3 C2 H4 108.4(13) . . ?
C11 C3 C2 110.35(12) . . ?
C11 C3 C10 110.43(13) . . ?
C2 C3 C10 108.51(11) . . ?
C11 C3 C4 110.43(12) . . ?
C2 C3 C4 108.65(11) . . ?
C10 C3 C4 108.40(12) . . ?
C5 C4 C3 110.26(11) . . ?
C5 C4 H5 109.2(10) . . ?
C3 C4 H5 109.1(10) . . ?
C5 C4 H6 109.3(10) . . ?
C3 C4 H6 108.4(10) . . ?
H5 C4 H6 110.6(14) . . ?
C4 C5 C6 109.74(11) . . ?
C4 C5 C9 109.41(12) . . ?
C6 C5 C9 109.33(12) . . ?
C4 C5 H7 107.8(10) . . ?
C6 C5 H7 109.2(10) . . ?
C9 C5 H7 111.3(10) . . ?
C5 C6 C1 109.77(10) . . ?
C5 C6 H8 110.8(9) . . ?
C1 C6 H8 106.8(9) . . ?
C5 C6 H9 110.4(11) . . ?
C1 C6 H9 108.6(10) . . ?
H8 C6 H9 110.4(13) . . ?
C1 C7 C8 110.32(11) . . ?
C1 C7 H10 108.5(10) . . ?
C8 C7 H10 111.6(10) . . ?
C1 C7 H11 110.5(9) . . ?
C8 C7 H11 108.6(9) . . ?
H10 C7 H11 107.4(13) . . ?
C12 C8 C7 109.44(12) . . ?
C12 C8 C10 110.79(13) . . ?
C7 C8 C10 108.75(11) . . ?
C12 C8 C9 110.43(13) . . ?
C7 C8 C9 108.84(11) . . ?
C10 C8 C9 108.56(12) . . ?
C5 C9 C8 110.02(11) . . ?
C5 C9 H12 110.7(10) . . ?
C8 C9 H12 109.1(10) . . ?
C5 C9 H13 111.1(10) . . ?
C8 C9 H13 107.4(10) . . ?
H12 C9 H13 108.5(13) . . ?
C8 C10 C3 111.49(11) . . ?
C8 C10 H14 109.4(9) . . ?
C3 C10 H14 108.6(9) . . ?
C8 C10 H15 113.8(10) . . ?
C3 C10 H15 107.4(10) . . ?
H14 C10 H15 105.9(13) . . ?
C3 C11 H16 110.9(12) . . ?
C3 C11 H17 112.6(10) . . ?
H16 C11 H17 106.6(15) . . ?
C3 C11 H18 110.6(10) . . ?
H16 C11 H18 105.5(16) . . ?
H17 C11 H18 110.3(14) . . ?
C8 C12 H19 110.1(11) . . ?
C8 C12 H20 113.1(13) . . ?
H19 C12 H20 106.5(16) . . ?
C8 C12 H21 108.7(12) . . ?
H19 C12 H21 109.7(17) . . ?
H20 C12 H21 108.7(17) . . ?
C14 C13 C18 120.85(12) . . ?
C14 C13 S1 121.72(10) . . ?
C18 C13 S1 117.43(10) . . ?
C15 C14 C13 117.59(12) . . ?
C15 C14 C19 116.37(12) . . ?
C13 C14 C19 126.04(12) . . ?
C16 C15 C14 122.84(13) . . ?
C16 C15 H22 119.4(10) . . ?
C14 C15 H22 117.7(10) . . ?
C15 C16 C17 118.05(12) . . ?
C15 C16 C20 121.96(13) . . ?
C17 C16 C20 119.98(13) . . ?
C16 C17 C18 122.28(13) . . ?
C16 C17 H23 121.3(10) . . ?
C18 C17 H23 116.4(10) . . ?
C17 C18 C13 118.38(12) . . ?
C17 C18 C21 116.57(12) . . ?
C13 C18 C21 125.04(12) . . ?
C14 C19 H24 111.0(9) . . ?
C14 C19 H25 109.0(9) . . ?
H24 C19 H25 107.0(13) . . ?
C14 C19 H26 111.9(10) . . ?
H24 C19 H26 109.6(14) . . ?
H25 C19 H26 108.3(13) . . ?
C16 C20 H27 114.3(15) . . ?
C16 C20 H28 107.2(14) . . ?
H27 C20 H28 111.3(19) . . ?
C16 C20 H29 109.9(12) . . ?
H27 C20 H29 104.2(19) . . ?
H28 C20 H29 109.9(18) . . ?
C18 C21 H30 107.7(12) . . ?
C18 C21 H31 113.9(12) . . ?
H30 C21 H31 110.1(16) . . ?
C18 C21 H32 113.7(11) . . ?
H30 C21 H32 106.3(15) . . ?
H31 C21 H32 104.9(15) . . ?
N2 C22 C23 110.88(11) . . ?
N2 C22 C27 105.71(11) . . ?
C23 C22 C27 109.96(12) . . ?
N2 C22 C28 112.45(10) . . ?
C23 C22 C28 109.46(11) . . ?
C27 C22 C28 108.28(11) . . ?
C22 C23 C24 111.09(12) . . ?
C22 C23 H33 108.1(11) . . ?
C24 C23 H33 109.1(12) . . ?
C22 C23 H34 111.9(11) . . ?
C24 C23 H34 108.1(11) . . ?
H33 C23 H34 108.5(15) . . ?
C32 C24 C31 110.92(17) . . ?
C32 C24 C25 110.49(17) . . ?
C31 C24 C25 108.76(13) . . ?
C32 C24 C23 110.10(14) . . ?
C31 C24 C23 107.95(13) . . ?
C25 C24 C23 108.54(14) . . ?
C26 C25 C24 110.26(13) . . ?
C26 C25 H35 110.7(11) . . ?
C24 C25 H35 108.9(12) . . ?
C26 C25 H36 108.2(11) . . ?
C24 C25 H36 110.0(11) . . ?
H35 C25 H36 108.7(16) . . ?
C30 C26 C25 109.34(14) . . ?
C30 C26 C27 108.59(14) . . ?
C25 C26 C27 110.51(14) . . ?
C30 C26 H37 109.9(11) . . ?
C25 C26 H37 108.3(11) . . ?
C27 C26 H37 110.2(11) . . ?
C22 C27 C26 109.39(12) . . ?
C22 C27 H38 111.2(11) . . ?
C26 C27 H38 110.8(11) . . ?
C22 C27 H39 106.8(12) . . ?
C26 C27 H39 110.1(12) . . ?
H38 C27 H39 108.4(15) . . ?
C22 C28 C29 110.04(11) . . ?
C22 C28 H40 108.9(8) . . ?
C29 C28 H40 112.4(9) . . ?
C22 C28 H41 108.4(10) . . ?
C29 C28 H41 112.2(10) . . ?
H40 C28 H41 104.6(13) . . ?
C33 C29 C30 109.93(12) . . ?
C33 C29 C31 111.05(13) . . ?
C30 C29 C31 108.94(12) . . ?
C33 C29 C28 109.47(12) . . ?
C30 C29 C28 108.60(11) . . ?
C31 C29 C28 108.81(11) . . ?
C26 C30 C29 110.53(12) . . ?
C26 C30 H42 111.1(11) . . ?
C29 C30 H42 109.8(11) . . ?
C26 C30 H43 107.4(11) . . ?
C29 C30 H43 110.3(11) . . ?
H42 C30 H43 107.7(15) . . ?
C29 C31 C24 111.32(12) . . ?
C29 C31 H44 109.3(10) . . ?
C24 C31 H44 110.7(10) . . ?
C29 C31 H45 112.0(10) . . ?
C24 C31 H45 109.5(10) . . ?
H44 C31 H45 103.9(14) . . ?
C24 C32 H46 112.4(15) . . ?
C24 C32 H47 111.7(14) . . ?
H46 C32 H47 106(2) . . ?
C24 C32 H48 110.0(14) . . ?
H46 C32 H48 109(2) . . ?
H47 C32 H48 107(2) . . ?
C29 C33 H49 111.7(12) . . ?
C29 C33 H50 113.1(12) . . ?
H49 C33 H50 105.6(16) . . ?
C29 C33 H51 108.8(12) . . ?
H49 C33 H51 107.8(16) . . ?
H50 C33 H51 109.6(17) . . ?
C39 C34 C35 120.83(12) . . ?
C39 C34 S2 120.95(10) . . ?
C35 C34 S2 118.21(10) . . ?
C36 C35 C34 118.18(13) . . ?
C36 C35 C40 116.79(12) . . ?
C34 C35 C40 125.02(12) . . ?
C37 C36 C35 122.53(13) . . ?
C37 C36 H52 121.2(11) . . ?
C35 C36 H52 116.3(11) . . ?
C38 C37 C36 117.89(12) . . ?
C38 C37 C41 121.17(14) . . ?
C36 C37 C41 120.94(14) . . ?
C37 C38 C39 122.73(13) . . ?
C37 C38 H53 118.1(9) . . ?
C39 C38 H53 119.2(9) . . ?
C38 C39 C34 117.67(13) . . ?
C38 C39 C42 116.48(13) . . ?
C34 C39 C42 125.83(12) . . ?
C35 C40 H54 110.9(11) . . ?
C35 C40 H55 112.5(11) . . ?
H54 C40 H55 109.9(15) . . ?
C35 C40 H56 114.1(12) . . ?
H54 C40 H56 105.4(15) . . ?
H55 C40 H56 103.6(15) . . ?
C37 C41 H57 112.1(16) . . ?
C37 C41 H58 112.3(13) . . ?
H57 C41 H58 107.9(19) . . ?
C37 C41 H59 114.1(14) . . ?
H57 C41 H59 102(2) . . ?
H58 C41 H59 108.4(19) . . ?
C39 C42 H60 112.6(10) . . ?
C39 C42 H61 111.4(11) . . ?
H60 C42 H61 108.0(15) . . ?
C39 C42 H62 111.1(12) . . ?
H60 C42 H62 107.0(16) . . ?
H61 C42 H62 106.3(16) . . ?

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
O2 S1 N1 C1 -36.59(12) . . . . ?
O1 S1 N1 C1 -165.16(10) . . . . ?
C13 S1 N1 C1 81.30(12) . . . . ?
O4 S2 N2 C22 -37.67(13) . . . . ?
O3 S2 N2 C22 -165.80(11) . . . . ?
C34 S2 N2 C22 79.41(12) . . . . ?
S1 N1 C1 C2 80.47(14) . . . . ?
S1 N1 C1 C6 -160.93(10) . . . . ?
S1 N1 C1 C7 -42.43(15) . . . . ?
N1 C1 C2 C3 177.04(10) . . . . ?
C6 C1 C2 C3 59.99(14) . . . . ?
C7 C1 C2 C3 -59.15(14) . . . . ?
C1 C2 C3 C11 179.48(12) . . . . ?
C1 C2 C3 C10 58.37(14) . . . . ?
C1 C2 C3 C4 -59.31(14) . . . . ?
C11 C3 C4 C5 179.94(13) . . . . ?
C2 C3 C4 C5 58.78(15) . . . . ?
C10 C3 C4 C5 -58.96(15) . . . . ?
C3 C4 C5 C6 -59.53(15) . . . . ?
C3 C4 C5 C9 60.42(15) . . . . ?
C4 C5 C6 C1 59.69(15) . . . . ?
C9 C5 C6 C1 -60.31(14) . . . . ?
N1 C1 C6 C5 -179.50(11) . . . . ?
C2 C1 C6 C5 -59.55(14) . . . . ?
C7 C1 C6 C5 60.25(14) . . . . ?
N1 C1 C7 C8 -177.35(10) . . . . ?
C2 C1 C7 C8 59.05(14) . . . . ?
C6 C1 C7 C8 -60.23(14) . . . . ?
C1 C7 C8 C12 -179.61(13) . . . . ?
C1 C7 C8 C10 -58.47(14) . . . . ?
C1 C7 C8 C9 59.63(14) . . . . ?
C4 C5 C9 C8 -60.39(15) . . . . ?
C6 C5 C9 C8 59.81(15) . . . . ?
C12 C8 C9 C5 -179.32(13) . . . . ?
C7 C8 C9 C5 -59.17(15) . . . . ?
C10 C8 C9 C5 59.05(14) . . . . ?
C12 C8 C10 C3 179.51(12) . . . . ?
C7 C8 C10 C3 59.19(14) . . . . ?
C9 C8 C10 C3 -59.08(14) . . . . ?
C11 C3 C10 C8 179.97(12) . . . . ?
C2 C3 C10 C8 -58.96(14) . . . . ?
C4 C3 C10 C8 58.87(14) . . . . ?
O2 S1 C13 C14 -2.51(12) . . . . ?
O1 S1 C13 C14 125.97(10) . . . . ?
N1 S1 C13 C14 -121.74(11) . . . . ?
O2 S1 C13 C18 176.81(9) . . . . ?
O1 S1 C13 C18 -54.71(11) . . . . ?
N1 S1 C13 C18 57.58(11) . . . . ?
C18 C13 C14 C15 -1.41(18) . . . . ?
S1 C13 C14 C15 177.89(10) . . . . ?
C18 C13 C14 C19 179.31(12) . . . . ?
S1 C13 C14 C19 -1.39(18) . . . . ?
C13 C14 C15 C16 1.0(2) . . . . ?
C19 C14 C15 C16 -179.68(13) . . . . ?
C14 C15 C16 C17 0.2(2) . . . . ?
C14 C15 C16 C20 -178.54(14) . . . . ?
C15 C16 C17 C18 -1.1(2) . . . . ?
C20 C16 C17 C18 177.74(13) . . . . ?
C16 C17 C18 C13 0.6(2) . . . . ?
C16 C17 C18 C21 -178.89(13) . . . . ?
C14 C13 C18 C17 0.66(18) . . . . ?
S1 C13 C18 C17 -178.68(10) . . . . ?
C14 C13 C18 C21 -179.87(13) . . . . ?
S1 C13 C18 C21 0.79(18) . . . . ?
S2 N2 C22 C23 77.62(15) . . . . ?
S2 N2 C22 C27 -163.25(11) . . . . ?
S2 N2 C22 C28 -45.30(16) . . . . ?
N2 C22 C23 C24 175.77(13) . . . . ?
C27 C22 C23 C24 59.24(17) . . . . ?
C28 C22 C23 C24 -59.60(17) . . . . ?
C22 C23 C24 C32 -179.90(18) . . . . ?
C22 C23 C24 C31 58.88(18) . . . . ?
C22 C23 C24 C25 -58.84(17) . . . . ?
C32 C24 C25 C26 179.36(15) . . . . ?
C31 C24 C25 C26 -58.67(17) . . . . ?
C23 C24 C25 C26 58.54(16) . . . . ?
C24 C25 C26 C30 59.94(17) . . . . ?
C24 C25 C26 C27 -59.53(17) . . . . ?
N2 C22 C27 C26 -177.77(12) . . . . ?
C23 C22 C27 C26 -58.03(16) . . . . ?
C28 C22 C27 C26 61.52(16) . . . . ?
C30 C26 C27 C22 -61.35(18) . . . . ?
C25 C26 C27 C22 58.58(17) . . . . ?
N2 C22 C28 C29 -177.25(11) . . . . ?
C23 C22 C28 C29 59.04(14) . . . . ?
C27 C22 C28 C29 -60.83(14) . . . . ?
C22 C28 C29 C33 179.61(12) . . . . ?
C22 C28 C29 C30 59.58(14) . . . . ?
C22 C28 C29 C31 -58.87(15) . . . . ?
C25 C26 C30 C29 -60.06(17) . . . . ?
C27 C26 C30 C29 60.59(18) . . . . ?
C33 C29 C30 C26 -179.26(13) . . . . ?
C31 C29 C30 C26 58.85(16) . . . . ?
C28 C29 C30 C26 -59.52(16) . . . . ?
C33 C29 C31 C24 -179.60(13) . . . . ?
C30 C29 C31 C24 -58.39(15) . . . . ?
C28 C29 C31 C24 59.84(16) . . . . ?
C32 C24 C31 C29 -179.96(15) . . . . ?
C25 C24 C31 C29 58.33(16) . . . . ?
C23 C24 C31 C29 -59.25(17) . . . . ?
O4 S2 C34 C39 -15.21(12) . . . . ?
O3 S2 C34 C39 113.46(11) . . . . ?
N2 S2 C34 C39 -132.59(11) . . . . ?
O4 S2 C34 C35 166.02(10) . . . . ?
O3 S2 C34 C35 -65.32(11) . . . . ?
N2 S2 C34 C35 48.64(12) . . . . ?
C39 C34 C35 C36 4.75(19) . . . . ?
S2 C34 C35 C36 -176.47(10) . . . . ?
C39 C34 C35 C40 -174.62(14) . . . . ?
S2 C34 C35 C40 4.15(18) . . . . ?
C34 C35 C36 C37 -2.4(2) . . . . ?
C40 C35 C36 C37 177.05(13) . . . . ?
C35 C36 C37 C38 -0.8(2) . . . . ?
C35 C36 C37 C41 179.27(13) . . . . ?
C36 C37 C38 C39 1.8(2) . . . . ?
C41 C37 C38 C39 -178.30(14) . . . . ?
C37 C38 C39 C34 0.5(2) . . . . ?
C37 C38 C39 C42 -178.09(14) . . . . ?
C35 C34 C39 C38 -3.83(19) . . . . ?
S2 C34 C39 C38 177.42(10) . . . . ?
C35 C34 C39 C42 174.60(14) . . . . ?
S2 C34 C39 C42 -4.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O3 0.786(18) 2.134(18) 2.9187(15) 176.3(18) 2_566
N2 H2 O1 0.82(2) 2.14(2) 2.9523(15) 170.9(19) 2_566

####################################################################### 
# 
# 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_20
_database_code_depnum_ccdc_archive 'CCDC 1962774'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2019-10-31 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;

_audit_creation_date             2017-04-03T01:18:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C17 H20 F3 N O2 S'
_chemical_formula_sum            'C17 H20 F3 N O2 S'
_chemical_formula_weight         359.4

#----------------------------------------------------------------------------#
#                   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                   11.0703(5)
_cell_length_b                   12.2683(5)
_cell_length_c                   13.2315(6)
_cell_angle_alpha                107.558(2)
_cell_angle_beta                 90.903(2)
_cell_angle_gamma                102.794(2)
_cell_volume                     1664.16(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5603
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      28.65

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             752

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

_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.6159
_exptl_absorpt_correction_T_max  0.7459

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

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_number            21801
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.278
_diffrn_reflns_theta_max         29.599
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.912
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.912
_reflns_Friedel_coverage         0
_reflns_number_total             8546
_reflns_number_gt                5933
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_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)+(0.0600P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         8546
_refine_ls_number_parameters     481
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1287
_refine_ls_wR_factor_gt          0.1146
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.062

#----------------------------------------------------------------------------#
#                   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'
F F 0.0171 0.0103 '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 0.92729(5) 0.51700(5) 0.16228(4) 0.02001(12) Uani 1 1 d . . . . .
S2 S 0.41314(4) 0.46304(4) 0.33489(4) 0.01854(12) Uani 1 1 d . . . . .
F1 F 0.8020(7) 0.1169(6) -0.1553(5) 0.095(2) Uani 0.65 1 d . U P A 1
F2 F 0.6451(3) 0.0023(3) -0.1161(3) 0.0770(10) Uani 0.65 1 d . U P A 1
F3 F 0.8256(3) 0.0200(2) -0.05535(19) 0.0511(7) Uani 0.65 1 d . U P A 1
F1B F 0.6376(6) 0.0696(6) -0.1592(5) 0.0828(19) Uiso 0.35 1 d . . P A 2
F2B F 0.8217(7) 0.1194(10) -0.1583(8) 0.0361(18) Uiso 0.35 1 d . . P A 2
F3B F 0.7413(8) -0.0038(7) -0.0791(6) 0.084(2) Uiso 0.35 1 d . . P A 2
F4 F 0.3639(15) 0.8613(14) 0.6568(12) 0.055(4) Uani 0.55 1 d . U P B 1
F5 F 0.4051(13) 0.9922(10) 0.5753(7) 0.037(2) Uani 0.55 1 d . U P B 1
F6 F 0.5446(15) 0.9038(10) 0.6000(12) 0.0370(19) Uani 0.55 1 d . U P B 1
F4B F 0.5353(18) 0.8939(14) 0.6151(15) 0.057(4) Uani 0.45 1 d . U P B 2
F5B F 0.3498(17) 0.8719(16) 0.6554(14) 0.0348(19) Uani 0.45 1 d . U P B 2
F6B F 0.4168(17) 0.9957(13) 0.5757(11) 0.051(4) Uani 0.45 1 d . U P B 2
O1 O 0.92435(14) 0.57447(14) 0.27309(11) 0.0272(3) Uani 1 1 d . . . . .
O2 O 1.04114(13) 0.48822(14) 0.12265(11) 0.0252(3) Uani 1 1 d . . . . .
O3 O 0.54270(12) 0.49509(13) 0.37496(10) 0.0229(3) Uani 1 1 d . . . . .
O4 O 0.37881(13) 0.39875(13) 0.22501(10) 0.0254(3) Uani 1 1 d . . . . .
N1 N 0.89271(15) 0.59781(15) 0.09532(13) 0.0190(4) Uani 1 1 d . . . . .
H1 H 0.904(2) 0.570(2) 0.028(2) 0.044(8) Uiso 1 1 d . . . . .
N2 N 0.34155(15) 0.38840(15) 0.40647(13) 0.0184(3) Uani 1 1 d . . . . .
H2 H 0.370(2) 0.421(2) 0.4709(19) 0.032(7) Uiso 1 1 d . . . . .
C1 C 0.79412(17) 0.66529(17) 0.11540(14) 0.0167(4) Uani 1 1 d . . . . .
C2 C 0.83011(19) 0.77125(18) 0.21690(16) 0.0231(4) Uani 1 1 d . . . . .
H2A H 0.91234 0.8208 0.212399 0.028 Uiso 1 1 calc R U . . .
H2B H 0.83581 0.743732 0.279482 0.028 Uiso 1 1 calc R U . . .
C3 C 0.7311(2) 0.84372(19) 0.22945(17) 0.0261(5) Uani 1 1 d . . . . .
H3A H 0.753944 0.912506 0.295902 0.031 Uiso 1 1 calc R U . . .
C4 C 0.7245(2) 0.88800(19) 0.13369(18) 0.0293(5) Uani 1 1 d . . . . .
H4A H 0.80633 0.938156 0.129026 0.035 Uiso 1 1 calc R U . . .
H4B H 0.662112 0.936011 0.142262 0.035 Uiso 1 1 calc R U . . .
C5 C 0.6886(2) 0.78301(18) 0.03187(17) 0.0251(5) Uani 1 1 d . . . . .
H5A H 0.684413 0.811882 -0.030855 0.03 Uiso 1 1 calc R U . . .
C6 C 0.78701(19) 0.71021(18) 0.01933(15) 0.0215(4) Uani 1 1 d . . . . .
H6A H 0.8691 0.759419 0.01398 0.026 Uiso 1 1 calc R U . . .
H6B H 0.765126 0.642596 -0.046878 0.026 Uiso 1 1 calc R U . . .
C7 C 0.66680(18) 0.58899(17) 0.12251(16) 0.0196(4) Uani 1 1 d . . . . .
H7A H 0.670459 0.55979 0.18429 0.023 Uiso 1 1 calc R U . . .
H7B H 0.644019 0.520124 0.057348 0.023 Uiso 1 1 calc R U . . .
C8 C 0.56814(18) 0.66149(18) 0.13481(16) 0.0215(4) Uani 1 1 d . . . . .
H8A H 0.485153 0.611426 0.139518 0.026 Uiso 1 1 calc R U . . .
C9 C 0.5621(2) 0.70597(19) 0.03901(16) 0.0253(5) Uani 1 1 d . . . . .
H9A H 0.538627 0.638272 -0.027015 0.03 Uiso 1 1 calc R U . . .
H9B H 0.498028 0.752143 0.046528 0.03 Uiso 1 1 calc R U . . .
C10 C 0.6046(2) 0.76649(19) 0.23699(16) 0.0250(5) Uani 1 1 d . . . . .
H10A H 0.540946 0.813248 0.247085 0.03 Uiso 1 1 calc R U . . .
H10B H 0.609038 0.737845 0.299038 0.03 Uiso 1 1 calc R U . . .
C11 C 0.81502(18) 0.38039(18) 0.12904(15) 0.0206(4) Uani 1 1 d . . . . .
C12 C 0.8220(2) 0.29191(19) 0.03620(16) 0.0243(4) Uani 1 1 d . . . . .
H12A H 0.883783 0.305174 -0.010581 0.029 Uiso 1 1 calc R U . . .
C13 C 0.7373(2) 0.1838(2) 0.01280(17) 0.0284(5) Uani 1 1 d . . . . .
C14 C 0.6450(2) 0.1653(2) 0.08029(19) 0.0318(5) Uani 1 1 d . . . . .
H14A H 0.586937 0.09122 0.063607 0.038 Uiso 1 1 calc R U . . .
C15 C 0.6380(2) 0.2545(2) 0.17129(19) 0.0311(5) Uani 1 1 d . . . . .
H15A H 0.574113 0.242366 0.21659 0.037 Uiso 1 1 calc R U . . .
C16 C 0.7233(2) 0.3613(2) 0.19680(17) 0.0258(5) Uani 1 1 d . . . . .
H16A H 0.719662 0.421855 0.260599 0.031 Uiso 1 1 calc R U . . .
C17 C 0.7468(3) 0.0864(2) -0.0838(2) 0.0482(7) Uani 1 1 d . . . . .
C18 C 0.20944(18) 0.31939(17) 0.38836(15) 0.0180(4) Uani 1 1 d . . . . .
C19 C 0.11737(19) 0.39118(19) 0.37386(17) 0.0236(4) Uani 1 1 d . . . . .
H19A H 0.132625 0.414899 0.30912 0.028 Uiso 1 1 calc R U . . .
H19B H 0.129117 0.463389 0.435737 0.028 Uiso 1 1 calc R U . . .
C20 C -0.0160(2) 0.3169(2) 0.36368(17) 0.0295(5) Uani 1 1 d . . . . .
H20A H -0.076033 0.363815 0.354006 0.035 Uiso 1 1 calc R U . . .
C21 C -0.0334(2) 0.2063(2) 0.26740(17) 0.0306(5) Uani 1 1 d . . . . .
H21A H -0.119735 0.158521 0.259657 0.037 Uiso 1 1 calc R U . . .
H21B H -0.018673 0.228734 0.201967 0.037 Uiso 1 1 calc R U . . .
C22 C 0.0577(2) 0.1344(2) 0.28220(18) 0.0316(5) Uani 1 1 d . . . . .
H22A H 0.045635 0.061846 0.219284 0.038 Uiso 1 1 calc R U . . .
C23 C 0.1917(2) 0.20836(19) 0.29166(17) 0.0273(5) Uani 1 1 d . . . . .
H23A H 0.251451 0.161835 0.300294 0.033 Uiso 1 1 calc R U . . .
H23B H 0.207385 0.230588 0.22623 0.033 Uiso 1 1 calc R U . . .
C24 C 0.1855(2) 0.2844(2) 0.48964(17) 0.0282(5) Uani 1 1 d . . . . .
H24A H 0.197649 0.356006 0.552227 0.034 Uiso 1 1 calc R U . . .
H24B H 0.245039 0.238543 0.500154 0.034 Uiso 1 1 calc R U . . .
C25 C 0.0517(2) 0.2102(2) 0.47917(19) 0.0384(6) Uani 1 1 d . . . . .
H25A H 0.036084 0.187422 0.545125 0.046 Uiso 1 1 calc R U . . .
C26 C -0.0393(2) 0.2822(2) 0.46442(18) 0.0378(6) Uani 1 1 d . . . . .
H26A H -0.02831 0.35377 0.526821 0.045 Uiso 1 1 calc R U . . .
H26B H -0.12567 0.235223 0.458752 0.045 Uiso 1 1 calc R U . . .
C27 C 0.0340(3) 0.0992(2) 0.3831(2) 0.0426(6) Uani 1 1 d . . . . .
H27A H -0.051804 0.050611 0.376554 0.051 Uiso 1 1 calc R U . . .
H27B H 0.092547 0.052041 0.392735 0.051 Uiso 1 1 calc R U . . .
C28 C 0.36745(18) 0.59819(18) 0.36063(15) 0.0197(4) Uani 1 1 d . . . . .
C29 C 0.41071(18) 0.68710(18) 0.45546(15) 0.0210(4) Uani 1 1 d . . . . .
H29A H 0.462143 0.675477 0.507551 0.025 Uiso 1 1 calc R U . . .
C30 C 0.37747(19) 0.79365(18) 0.47296(16) 0.0224(4) Uani 1 1 d . . . . .
C31 C 0.3015(2) 0.8104(2) 0.39721(18) 0.0285(5) Uani 1 1 d . . . . .
H31A H 0.279992 0.883847 0.409499 0.034 Uiso 1 1 calc R U . . .
C32 C 0.2574(2) 0.7199(2) 0.30381(18) 0.0309(5) Uani 1 1 d . . . . .
H32A H 0.204099 0.730838 0.252624 0.037 Uiso 1 1 calc R U . . .
C33 C 0.29016(19) 0.61385(19) 0.28438(16) 0.0244(4) Uani 1 1 d . . . . .
H33A H 0.260469 0.552086 0.219806 0.029 Uiso 1 1 calc R U . . .
C34 C 0.4215(2) 0.8885(2) 0.57692(18) 0.0306(5) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 O1 1.4268(14) . ?
S1 O2 1.4472(14) . ?
S1 N1 1.6130(17) . ?
S1 C11 1.778(2) . ?
S2 O4 1.4276(14) . ?
S2 O3 1.4468(14) . ?
S2 N2 1.6091(17) . ?
S2 C28 1.777(2) . ?
F1 C17 1.240(7) . ?
F2 C17 1.312(4) . ?
F3 C17 1.433(4) . ?
F1B C17 1.493(7) . ?
F2B C17 1.393(11) . ?
F3B C17 1.115(8) . ?
F4 C34 1.332(15) . ?
F5 C34 1.330(11) . ?
F6 C34 1.350(16) . ?
F4B C34 1.33(2) . ?
F5B C34 1.354(17) . ?
F6B C34 1.333(15) . ?
N1 C1 1.491(2) . ?
N1 H1 0.88(3) . ?
N2 C18 1.494(2) . ?
N2 H2 0.85(2) . ?
C1 C7 1.531(3) . ?
C1 C2 1.534(3) . ?
C1 C6 1.538(3) . ?
C2 C3 1.539(3) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C4 1.528(3) . ?
C3 C10 1.530(3) . ?
C3 H3A 1 . ?
C4 C5 1.530(3) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 C9 1.528(3) . ?
C5 C6 1.536(3) . ?
C5 H5A 1 . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 C8 1.536(3) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 C9 1.530(3) . ?
C8 C10 1.534(3) . ?
C8 H8A 1 . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C12 1.389(3) . ?
C11 C16 1.392(3) . ?
C12 C13 1.387(3) . ?
C12 H12A 0.95 . ?
C13 C14 1.394(3) . ?
C13 C17 1.487(3) . ?
C14 C15 1.378(3) . ?
C14 H14A 0.95 . ?
C15 C16 1.377(3) . ?
C15 H15A 0.95 . ?
C16 H16A 0.95 . ?
C18 C19 1.531(3) . ?
C18 C23 1.534(3) . ?
C18 C24 1.535(3) . ?
C19 C20 1.534(3) . ?
C19 H19A 0.99 . ?
C19 H19B 0.99 . ?
C20 C26 1.526(3) . ?
C20 C21 1.528(3) . ?
C20 H20A 1 . ?
C21 C22 1.525(3) . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
C22 C27 1.532(3) . ?
C22 C23 1.539(3) . ?
C22 H22A 1 . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C24 C25 1.537(3) . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
C25 C26 1.524(4) . ?
C25 C27 1.529(4) . ?
C25 H25A 1 . ?
C26 H26A 0.99 . ?
C26 H26B 0.99 . ?
C27 H27A 0.99 . ?
C27 H27B 0.99 . ?
C28 C29 1.385(3) . ?
C28 C33 1.396(3) . ?
C29 C30 1.390(3) . ?
C29 H29A 0.95 . ?
C30 C31 1.389(3) . ?
C30 C34 1.499(3) . ?
C31 C32 1.383(3) . ?
C31 H31A 0.95 . ?
C32 C33 1.378(3) . ?
C32 H32A 0.95 . ?
C33 H33A 0.95 . ?

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 119.59(9) . . ?
O1 S1 N1 109.35(9) . . ?
O2 S1 N1 104.83(9) . . ?
O1 S1 C11 106.98(9) . . ?
O2 S1 C11 105.48(9) . . ?
N1 S1 C11 110.44(9) . . ?
O4 S2 O3 119.21(8) . . ?
O4 S2 N2 109.26(9) . . ?
O3 S2 N2 105.33(9) . . ?
O4 S2 C28 107.45(9) . . ?
O3 S2 C28 105.44(9) . . ?
N2 S2 C28 109.92(9) . . ?
C1 N1 S1 126.81(13) . . ?
C1 N1 H1 113.9(17) . . ?
S1 N1 H1 111.3(17) . . ?
C18 N2 S2 127.30(13) . . ?
C18 N2 H2 115.9(17) . . ?
S2 N2 H2 109.4(17) . . ?
N1 C1 C7 112.66(16) . . ?
N1 C1 C2 111.04(15) . . ?
C7 C1 C2 109.71(15) . . ?
N1 C1 C6 105.27(15) . . ?
C7 C1 C6 109.13(15) . . ?
C2 C1 C6 108.88(16) . . ?
C1 C2 C3 109.19(16) . . ?
C1 C2 H2A 109.8 . . ?
C3 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
C3 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
C4 C3 C10 109.84(18) . . ?
C4 C3 C2 109.59(17) . . ?
C10 C3 C2 109.35(18) . . ?
C4 C3 H3A 109.3 . . ?
C10 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C3 C4 C5 109.54(17) . . ?
C3 C4 H4A 109.8 . . ?
C5 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
C5 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
C9 C5 C4 109.69(17) . . ?
C9 C5 C6 109.24(17) . . ?
C4 C5 C6 109.05(18) . . ?
C9 C5 H5A 109.6 . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
C5 C6 C1 110.02(16) . . ?
C5 C6 H6A 109.7 . . ?
C1 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
C1 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C1 C7 C8 109.87(16) . . ?
C1 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
C1 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C10 109.63(17) . . ?
C9 C8 C7 109.62(16) . . ?
C10 C8 C7 108.63(16) . . ?
C9 C8 H8A 109.6 . . ?
C10 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
C5 C9 C8 109.79(16) . . ?
C5 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
C5 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C3 C10 C8 109.69(16) . . ?
C3 C10 H10A 109.7 . . ?
C8 C10 H10A 109.7 . . ?
C3 C10 H10B 109.7 . . ?
C8 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 C16 120.4(2) . . ?
C12 C11 S1 119.21(15) . . ?
C16 C11 S1 120.36(16) . . ?
C13 C12 C11 119.0(2) . . ?
C13 C12 H12A 120.5 . . ?
C11 C12 H12A 120.5 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 C17 119.7(2) . . ?
C14 C13 C17 119.8(2) . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C15 C16 C11 120.0(2) . . ?
C15 C16 H16A 120 . . ?
C11 C16 H16A 120 . . ?
F1 C17 F2 115.3(4) . . ?
F3B C17 F2B 116.3(7) . . ?
F1 C17 F3 101.5(4) . . ?
F2 C17 F3 98.6(3) . . ?
F3B C17 C13 120.5(5) . . ?
F1 C17 C13 115.5(4) . . ?
F2 C17 C13 114.7(3) . . ?
F2B C17 C13 115.5(5) . . ?
F3 C17 C13 108.4(2) . . ?
F3B C17 F1B 103.5(6) . . ?
F2B C17 F1B 87.3(4) . . ?
C13 C17 F1B 106.1(3) . . ?
N2 C18 C19 112.94(16) . . ?
N2 C18 C23 110.79(16) . . ?
C19 C18 C23 109.49(16) . . ?
N2 C18 C24 104.71(15) . . ?
C19 C18 C24 109.11(17) . . ?
C23 C18 C24 109.68(17) . . ?
C18 C19 C20 109.58(18) . . ?
C18 C19 H19A 109.8 . . ?
C20 C19 H19A 109.8 . . ?
C18 C19 H19B 109.8 . . ?
C20 C19 H19B 109.8 . . ?
H19A C19 H19B 108.2 . . ?
C26 C20 C21 109.7(2) . . ?
C26 C20 C19 109.39(18) . . ?
C21 C20 C19 109.29(17) . . ?
C26 C20 H20A 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C22 C21 C20 109.58(17) . . ?
C22 C21 H21A 109.8 . . ?
C20 C21 H21A 109.8 . . ?
C22 C21 H21B 109.8 . . ?
C20 C21 H21B 109.8 . . ?
H21A C21 H21B 108.2 . . ?
C21 C22 C27 109.6(2) . . ?
C21 C22 C23 109.43(19) . . ?
C27 C22 C23 109.82(19) . . ?
C21 C22 H22A 109.3 . . ?
C27 C22 H22A 109.3 . . ?
C23 C22 H22A 109.3 . . ?
C18 C23 C22 108.98(17) . . ?
C18 C23 H23A 109.9 . . ?
C22 C23 H23A 109.9 . . ?
C18 C23 H23B 109.9 . . ?
C22 C23 H23B 109.9 . . ?
H23A C23 H23B 108.3 . . ?
C18 C24 C25 109.42(17) . . ?
C18 C24 H24A 109.8 . . ?
C25 C24 H24A 109.8 . . ?
C18 C24 H24B 109.8 . . ?
C25 C24 H24B 109.8 . . ?
H24A C24 H24B 108.2 . . ?
C26 C25 C27 109.7(2) . . ?
C26 C25 C24 109.4(2) . . ?
C27 C25 C24 109.5(2) . . ?
C26 C25 H25A 109.4 . . ?
C27 C25 H25A 109.4 . . ?
C24 C25 H25A 109.4 . . ?
C25 C26 C20 109.64(18) . . ?
C25 C26 H26A 109.7 . . ?
C20 C26 H26A 109.7 . . ?
C25 C26 H26B 109.7 . . ?
C20 C26 H26B 109.7 . . ?
H26A C26 H26B 108.2 . . ?
C25 C27 C22 109.30(19) . . ?
C25 C27 H27A 109.8 . . ?
C22 C27 H27A 109.8 . . ?
C25 C27 H27B 109.8 . . ?
C22 C27 H27B 109.8 . . ?
H27A C27 H27B 108.3 . . ?
C29 C28 C33 121.01(19) . . ?
C29 C28 S2 119.40(15) . . ?
C33 C28 S2 119.59(16) . . ?
C28 C29 C30 118.73(19) . . ?
C28 C29 H29A 120.6 . . ?
C30 C29 H29A 120.6 . . ?
C31 C30 C29 120.7(2) . . ?
C31 C30 C34 120.7(2) . . ?
C29 C30 C34 118.57(19) . . ?
C32 C31 C30 119.7(2) . . ?
C32 C31 H31A 120.1 . . ?
C30 C31 H31A 120.1 . . ?
C33 C32 C31 120.5(2) . . ?
C33 C32 H32A 119.7 . . ?
C31 C32 H32A 119.7 . . ?
C32 C33 C28 119.3(2) . . ?
C32 C33 H33A 120.4 . . ?
C28 C33 H33A 120.4 . . ?
F5 C34 F4 108.7(10) . . ?
F4B C34 F6B 108.2(10) . . ?
F5 C34 F6 106.3(8) . . ?
F4 C34 F6 107.2(10) . . ?
F4B C34 F5B 103.6(12) . . ?
F6B C34 F5B 103.6(12) . . ?
F5 C34 C30 112.3(4) . . ?
F4B C34 C30 114.3(8) . . ?
F4 C34 C30 111.4(6) . . ?
F6B C34 C30 114.1(6) . . ?
F6 C34 C30 110.7(6) . . ?
F5B C34 C30 112.0(6) . . ?

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
O1 S1 N1 C1 -41.17(19) . . . . ?
O2 S1 N1 C1 -170.54(16) . . . . ?
C11 S1 N1 C1 76.29(18) . . . . ?
O4 S2 N2 C18 -41.01(18) . . . . ?
O3 S2 N2 C18 -170.19(15) . . . . ?
C28 S2 N2 C18 76.67(18) . . . . ?
S1 N1 C1 C7 -52.6(2) . . . . ?
S1 N1 C1 C2 70.9(2) . . . . ?
S1 N1 C1 C6 -171.39(14) . . . . ?
N1 C1 C2 C3 175.44(16) . . . . ?
C7 C1 C2 C3 -59.4(2) . . . . ?
C6 C1 C2 C3 60.0(2) . . . . ?
C1 C2 C3 C4 -60.6(2) . . . . ?
C1 C2 C3 C10 59.8(2) . . . . ?
C10 C3 C4 C5 -59.6(2) . . . . ?
C2 C3 C4 C5 60.6(2) . . . . ?
C3 C4 C5 C9 59.7(2) . . . . ?
C3 C4 C5 C6 -59.9(2) . . . . ?
C9 C5 C6 C1 -59.8(2) . . . . ?
C4 C5 C6 C1 60.0(2) . . . . ?
N1 C1 C6 C5 -179.32(16) . . . . ?
C7 C1 C6 C5 59.5(2) . . . . ?
C2 C1 C6 C5 -60.2(2) . . . . ?
N1 C1 C7 C8 -175.77(15) . . . . ?
C2 C1 C7 C8 60.0(2) . . . . ?
C6 C1 C7 C8 -59.2(2) . . . . ?
C1 C7 C8 C9 59.6(2) . . . . ?
C1 C7 C8 C10 -60.1(2) . . . . ?
C4 C5 C9 C8 -59.7(2) . . . . ?
C6 C5 C9 C8 59.8(2) . . . . ?
C10 C8 C9 C5 59.3(2) . . . . ?
C7 C8 C9 C5 -59.9(2) . . . . ?
C4 C3 C10 C8 59.4(2) . . . . ?
C2 C3 C10 C8 -60.9(2) . . . . ?
C9 C8 C10 C3 -59.1(2) . . . . ?
C7 C8 C10 C3 60.7(2) . . . . ?
O1 S1 C11 C12 -161.36(15) . . . . ?
O2 S1 C11 C12 -33.01(18) . . . . ?
N1 S1 C11 C12 79.73(17) . . . . ?
O1 S1 C11 C16 16.88(19) . . . . ?
O2 S1 C11 C16 145.22(16) . . . . ?
N1 S1 C11 C16 -102.03(17) . . . . ?
C16 C11 C12 C13 -0.8(3) . . . . ?
S1 C11 C12 C13 177.38(16) . . . . ?
C11 C12 C13 C14 1.4(3) . . . . ?
C11 C12 C13 C17 -177.3(2) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C17 C13 C14 C15 178.3(2) . . . . ?
C13 C14 C15 C16 -1.2(3) . . . . ?
C14 C15 C16 C11 1.8(3) . . . . ?
C12 C11 C16 C15 -0.7(3) . . . . ?
S1 C11 C16 C15 -178.93(16) . . . . ?
C12 C13 C17 F3B 133.0(6) . . . . ?
C14 C13 C17 F3B -45.7(7) . . . . ?
C12 C13 C17 F1 -22.9(5) . . . . ?
C14 C13 C17 F1 158.3(4) . . . . ?
C12 C13 C17 F2 -160.8(3) . . . . ?
C14 C13 C17 F2 20.5(4) . . . . ?
C12 C13 C17 F2B -15.3(5) . . . . ?
C14 C13 C17 F2B 166.0(4) . . . . ?
C12 C13 C17 F3 90.2(3) . . . . ?
C14 C13 C17 F3 -88.5(3) . . . . ?
C12 C13 C17 F1B -110.1(4) . . . . ?
C14 C13 C17 F1B 71.2(4) . . . . ?
S2 N2 C18 C19 -52.2(2) . . . . ?
S2 N2 C18 C23 71.0(2) . . . . ?
S2 N2 C18 C24 -170.78(15) . . . . ?
N2 C18 C19 C20 -176.01(16) . . . . ?
C23 C18 C19 C20 60.0(2) . . . . ?
C24 C18 C19 C20 -60.0(2) . . . . ?
C18 C19 C20 C26 60.2(2) . . . . ?
C18 C19 C20 C21 -59.9(2) . . . . ?
C26 C20 C21 C22 -59.6(2) . . . . ?
C19 C20 C21 C22 60.3(2) . . . . ?
C20 C21 C22 C27 59.8(2) . . . . ?
C20 C21 C22 C23 -60.7(2) . . . . ?
N2 C18 C23 C22 174.82(17) . . . . ?
C19 C18 C23 C22 -60.0(2) . . . . ?
C24 C18 C23 C22 59.7(2) . . . . ?
C21 C22 C23 C18 60.3(2) . . . . ?
C27 C22 C23 C18 -60.0(2) . . . . ?
N2 C18 C24 C25 -178.90(18) . . . . ?
C19 C18 C24 C25 59.9(2) . . . . ?
C23 C18 C24 C25 -60.0(2) . . . . ?
C18 C24 C25 C26 -60.1(2) . . . . ?
C18 C24 C25 C27 60.0(3) . . . . ?
C27 C25 C26 C20 -59.8(2) . . . . ?
C24 C25 C26 C20 60.3(2) . . . . ?
C21 C20 C26 C25 59.6(2) . . . . ?
C19 C20 C26 C25 -60.3(2) . . . . ?
C26 C25 C27 C22 59.9(3) . . . . ?
C24 C25 C27 C22 -60.2(3) . . . . ?
C21 C22 C27 C25 -59.9(2) . . . . ?
C23 C22 C27 C25 60.4(3) . . . . ?
O4 S2 C28 C29 -167.58(15) . . . . ?
O3 S2 C28 C29 -39.45(18) . . . . ?
N2 S2 C28 C29 73.62(17) . . . . ?
O4 S2 C28 C33 11.42(19) . . . . ?
O3 S2 C28 C33 139.55(16) . . . . ?
N2 S2 C28 C33 -107.38(17) . . . . ?
C33 C28 C29 C30 -1.1(3) . . . . ?
S2 C28 C29 C30 177.92(15) . . . . ?
C28 C29 C30 C31 0.5(3) . . . . ?
C28 C29 C30 C34 178.33(18) . . . . ?
C29 C30 C31 C32 0.7(3) . . . . ?
C34 C30 C31 C32 -177.1(2) . . . . ?
C30 C31 C32 C33 -1.3(3) . . . . ?
C31 C32 C33 C28 0.7(3) . . . . ?
C29 C28 C33 C32 0.5(3) . . . . ?
S2 C28 C33 C32 -178.50(16) . . . . ?
C31 C30 C34 F5 -14.8(7) . . . . ?
C29 C30 C34 F5 167.4(7) . . . . ?
C31 C30 C34 F4B -145.6(8) . . . . ?
C29 C30 C34 F4B 36.6(8) . . . . ?
C31 C30 C34 F4 107.4(10) . . . . ?
C29 C30 C34 F4 -70.5(10) . . . . ?
C31 C30 C34 F6B -20.4(9) . . . . ?
C29 C30 C34 F6B 161.8(9) . . . . ?
C31 C30 C34 F6 -133.5(6) . . . . ?
C29 C30 C34 F6 48.7(6) . . . . ?
C31 C30 C34 F5B 97.0(12) . . . . ?
C29 C30 C34 F5B -80.9(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.88(3) 2.05(3) 2.922(2) 171(2) 2_765
N2 H2 O3 0.85(2) 2.09(2) 2.937(2) 175(2) 2_666

