# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_rds610_0m
_database_code_depnum_ccdc_archive 'CCDC 1575965'
_audit_update_record             
;
2017-09-21 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 F N4 O2 S'
_chemical_formula_weight         394.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   14.6027(7)
_cell_length_b                   7.1994(4)
_cell_length_c                   18.1327(10)
_cell_angle_alpha                90
_cell_angle_beta                 107.694(2)
_cell_angle_gamma                90
_cell_volume                     1816.13(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.213
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34880
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.141
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5533
_reflns_number_gt                4391
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0492P)²+0.7375P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5533
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0930
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.18137(2) 0.72926(4) 0.35479(2) 0.01947(9) Uani 1 1 d . . . . .
F1 F 0.40928(7) 0.04701(14) 0.38105(7) 0.0440(3) Uani 1 1 d . . . . .
O1 O 0.18005(6) 0.33835(12) 0.52330(5) 0.01506(18) Uani 1 1 d . . . . .
O2 O 0.46763(6) 0.59187(14) 0.69473(5) 0.0223(2) Uani 1 1 d . . . . .
N1 N 0.04089(7) 0.20541(13) 0.46138(6) 0.01259(19) Uani 1 1 d . . . . .
N2 N -0.09656(8) 0.04596(15) 0.39903(6) 0.0164(2) Uani 1 1 d . . . . .
H2A H -0.0787(12) -0.037(2) 0.4352(10) 0.025(4) Uiso 1 1 d . . . . .
H2B H -0.1527(13) 0.039(3) 0.3671(11) 0.032(5) Uiso 1 1 d . . . . .
N3 N -0.23954(8) 0.34599(16) 0.24889(7) 0.0212(2) Uani 1 1 d . . . . .
N4 N -0.05545(9) 0.67169(16) 0.32401(7) 0.0197(2) Uani 1 1 d . . . . .
H4A H -0.0187(14) 0.756(3) 0.3217(11) 0.037(5) Uiso 1 1 d . . . . .
H4B H -0.1156(14) 0.677(3) 0.2954(11) 0.035(5) Uiso 1 1 d . . . . .
C1 C -0.04580(8) 0.20432(16) 0.40712(6) 0.0122(2) Uani 1 1 d . . . . .
C2 C -0.08011(8) 0.36076(16) 0.35963(7) 0.0126(2) Uani 1 1 d . . . . .
C3 C -0.02317(8) 0.52262(16) 0.36870(7) 0.0129(2) Uani 1 1 d . . . . .
C4 C 0.06831(8) 0.52213(16) 0.42556(7) 0.0130(2) Uani 1 1 d . . . . .
C5 C 0.09342(8) 0.35954(16) 0.46742(6) 0.0120(2) Uani 1 1 d . . . . .
C6 C 0.13386(9) 0.68663(16) 0.43895(7) 0.0148(2) Uani 1 1 d . . . . .
H6 H 0.0964 0.7986 0.4454 0.018 Uiso 1 1 calc R U . . .
C7 C 0.21679(8) 0.66403(17) 0.51103(7) 0.0148(2) Uani 1 1 d . . . . .
C8 C 0.23904(8) 0.49227(17) 0.54592(7) 0.0139(2) Uani 1 1 d . . . . .
C9 C 0.32194(9) 0.45884(18) 0.60706(7) 0.0160(2) Uani 1 1 d . . . . .
H9 H 0.3358 0.3383 0.6290 0.019 Uiso 1 1 calc R U . . .
C10 C 0.38383(9) 0.60629(19) 0.63517(7) 0.0179(2) Uani 1 1 d . . . . .
C11 C 0.36214(10) 0.78369(19) 0.60349(8) 0.0205(3) Uani 1 1 d . . . . .
H11 H 0.4037 0.8850 0.6241 0.025 Uiso 1 1 calc R U . . .
C12 C 0.28003(9) 0.81104(18) 0.54201(8) 0.0187(3) Uani 1 1 d . . . . .
H12 H 0.2660 0.9316 0.5202 0.022 Uiso 1 1 calc R U . . .
C13 C -0.16924(9) 0.35268(16) 0.29948(7) 0.0144(2) Uani 1 1 d . . . . .
C14 C 0.50015(10) 0.4110(2) 0.72090(8) 0.0278(3) Uani 1 1 d . . . . .
H14A H 0.5614 0.4197 0.7624 0.042 Uiso 1 1 calc R U . . .
H14B H 0.5092 0.3388 0.6778 0.042 Uiso 1 1 calc R U . . .
H14C H 0.4524 0.3496 0.7406 0.042 Uiso 1 1 calc R U . . .
C15 C 0.25102(9) 0.52546(18) 0.36128(7) 0.0173(2) Uani 1 1 d . . . . .
C16 C 0.21050(10) 0.36686(19) 0.32028(8) 0.0218(3) Uani 1 1 d . . . . .
H16 H 0.1459 0.3697 0.2876 0.026 Uiso 1 1 calc R U . . .
C17 C 0.26371(11) 0.2049(2) 0.32672(9) 0.0263(3) Uani 1 1 d . . . . .
H17 H 0.2364 0.0964 0.2988 0.032 Uiso 1 1 calc R U . . .
C18 C 0.35693(11) 0.2053(2) 0.37460(9) 0.0280(3) Uani 1 1 d . . . . .
C19 C 0.39989(11) 0.3598(2) 0.41574(9) 0.0290(3) Uani 1 1 d . . . . .
H19 H 0.4646 0.3556 0.4482 0.035 Uiso 1 1 calc R U . . .
C20 C 0.34609(10) 0.5213(2) 0.40844(8) 0.0236(3) Uani 1 1 d . . . . .
H20 H 0.3743 0.6299 0.4358 0.028 Uiso 1 1 calc R U . . .


_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 C15 1.7687(13) . ?
S1 C6 1.8836(13) . ?
F1 C18 1.3575(17) . ?
O1 C5 1.3679(14) . ?
O1 C8 1.3869(14) . ?
O2 C10 1.3680(15) . ?
O2 C14 1.4173(18) . ?
N1 C5 1.3344(15) . ?
N1 C1 1.3467(15) . ?
N2 C1 1.3434(15) . ?
N2 H2A 0.868(18) . ?
N2 H2B 0.849(19) . ?
N3 C13 1.1512(16) . ?
N4 C3 1.3411(15) . ?
N4 H4A 0.82(2) . ?
N4 H4B 0.87(2) . ?
C1 C2 1.4137(16) . ?
C2 C3 1.4118(16) . ?
C2 C13 1.4227(16) . ?
C3 C4 1.4179(16) . ?
C4 C5 1.3825(16) . ?
C4 C6 1.4954(16) . ?
C6 C7 1.4965(17) . ?
C6 H6 1.0000 . ?
C7 C8 1.3820(17) . ?
C7 C12 1.4047(17) . ?
C8 C9 1.3916(17) . ?
C9 C10 1.3869(17) . ?
C9 H9 0.9500 . ?
C10 C11 1.3967(19) . ?
C11 C12 1.3809(18) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C20 1.3921(18) . ?
C15 C16 1.3925(18) . ?
C16 C17 1.387(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.374(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.379(2) . ?
C19 C20 1.387(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

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
C15 S1 C6 99.02(6) . . ?
C5 O1 C8 118.78(9) . . ?
C10 O2 C14 117.54(10) . . ?
C5 N1 C1 117.00(10) . . ?
C1 N2 H2A 118.4(11) . . ?
C1 N2 H2B 120.7(13) . . ?
H2A N2 H2B 118.7(16) . . ?
C3 N4 H4A 120.5(14) . . ?
C3 N4 H4B 119.8(12) . . ?
H4A N4 H4B 119.6(18) . . ?
N2 C1 N1 116.72(10) . . ?
N2 C1 C2 121.87(11) . . ?
N1 C1 C2 121.39(10) . . ?
C3 C2 C1 119.96(10) . . ?
C3 C2 C13 119.48(10) . . ?
C1 C2 C13 120.44(10) . . ?
N4 C3 C2 120.25(11) . . ?
N4 C3 C4 121.45(11) . . ?
C2 C3 C4 118.29(10) . . ?
C5 C4 C3 115.80(10) . . ?
C5 C4 C6 122.11(10) . . ?
C3 C4 C6 122.08(10) . . ?
N1 C5 O1 110.31(10) . . ?
N1 C5 C4 127.53(11) . . ?
O1 C5 C4 122.16(10) . . ?
C4 C6 C7 111.33(10) . . ?
C4 C6 S1 111.88(8) . . ?
C7 C6 S1 109.01(8) . . ?
C4 C6 H6 108.2 . . ?
C7 C6 H6 108.2 . . ?
S1 C6 H6 108.2 . . ?
C8 C7 C12 117.17(11) . . ?
C8 C7 C6 120.82(10) . . ?
C12 C7 C6 121.77(11) . . ?
C7 C8 O1 122.76(10) . . ?
C7 C8 C9 123.09(11) . . ?
O1 C8 C9 114.15(11) . . ?
C10 C9 C8 118.18(12) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
O2 C10 C9 123.96(12) . . ?
O2 C10 C11 115.51(11) . . ?
C9 C10 C11 120.52(12) . . ?
C12 C11 C10 119.68(11) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C7 121.29(12) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
N3 C13 C2 177.53(13) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 119.54(12) . . ?
C20 C15 S1 120.30(10) . . ?
C16 C15 S1 120.15(10) . . ?
C17 C16 C15 120.56(13) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 118.25(13) . . ?
C18 C17 H17 120.9 . . ?
C16 C17 H17 120.9 . . ?
F1 C18 C17 118.43(14) . . ?
F1 C18 C19 118.59(14) . . ?
C17 C18 C19 122.97(14) . . ?
C18 C19 C20 118.23(13) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 H19 120.9 . . ?
C19 C20 C15 120.43(13) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?

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
N2 H2A N1 0.868(18) 2.158(18) 3.0152(15) 169.2(16) 3_556
N2 H2B N3 0.849(19) 2.611(19) 3.3306(16) 143.2(16) 2_445
N4 H4A S1 0.82(2) 2.80(2) 3.3570(13) 126.5(16) .
N4 H4A O2 0.82(2) 2.50(2) 2.9976(15) 120.0(16) 4_575
N4 H4B N3 0.87(2) 2.36(2) 3.1430(16) 149.1(16) 2_455

_refine_diff_density_max         0.415
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_rds526
_database_code_depnum_ccdc_archive 'CCDC 1577117'
_audit_update_record             
;
2017-09-28 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            SP123
_chemical_formula_moiety         'C21 H18 N4 O3 S'
_chemical_formula_sum            'C21 H18 N4 O3 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         406.45

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_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                   21.6226(4)
_cell_length_b                   14.4826(4)
_cell_length_c                   13.0479(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.052(2)
_cell_angle_gamma                90
_cell_volume                     3787.05(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    865
_cell_measurement_theta_min      1.7425
_cell_measurement_theta_max      33.7986
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.343
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.136
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696

_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            46344
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         30.54
_diffrn_reflns_theta_full        30.54
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;

?
;

_reflns_number_total             5803
_reflns_number_gt                4575
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1053
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_number_reflns         5803
_refine_ls_number_parameters     280
_refine_ls_number_restraints     2
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0428P)²+3.4981P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.743
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.11656(2) 0.53801(3) 0.27474(2) 0.03700(11) Uani d . . . 1 . .
O O1 0.21943(6) 0.60312(7) 0.60019(7) 0.0357(2) Uani d . . . 1 . .
O O2 0.04849(7) 0.79138(7) 0.63638(9) 0.0446(3) Uani d . . . 1 . .
O O3 0.12294(5) 0.26698(6) 0.61798(7) 0.02655(19) Uani d . . . 1 . .
N N1 0.31833(7) 0.55070(8) 0.61283(8) 0.0328(3) Uani d . . . 1 . .
N N2 0.42390(7) 0.50234(10) 0.63825(9) 0.0370(3) Uani d . . D 1 . .
H H2A 0.4316(10) 0.5062(14) 0.7096(14) 0.050(5) Uiso d . . D 1 . .
H H2B 0.4583(9) 0.5004(15) 0.6158(17) 0.058(6) Uiso d . . D 1 . .
N N3 0.43786(7) 0.48897(9) 0.37905(9) 0.0373(3) Uani d . . . 1 . .
N N4 0.26886(8) 0.57226(9) 0.27125(9) 0.0357(3) Uani d . . D 1 . .
H H4A 0.2950(10) 0.5412(15) 0.2452(18) 0.066(7) Uiso d . . D 1 . .
H H4B 0.2267(8) 0.5694(13) 0.2306(15) 0.043(5) Uiso d . . D 1 . .
C C1 0.36350(8) 0.53105(9) 0.56893(9) 0.0318(3) Uani d . . . 1 . .
C C2 0.34842(8) 0.53763(9) 0.45336(9) 0.0314(3) Uani d . . . 1 . .
C C3 0.28515(8) 0.56869(9) 0.38315(9) 0.0321(3) Uani d . . . 1 . .
C C4 0.23942(8) 0.59638(9) 0.43063(9) 0.0321(3) Uani d . . . 1 . .
C C5 0.25999(8) 0.58317(9) 0.54444(10) 0.0317(3) Uani d . . . 1 . .
C C6 0.17119(8) 0.63106(10) 0.36419(10) 0.0342(3) Uani d . . . 1 . .
H H6 0.175966 0.680226 0.313858 0.041 Uiso calc U . R 1 . .
C C7 0.13884(8) 0.67442(9) 0.43575(10) 0.0334(3) Uani d . . . 1 . .
C C8 0.16321(8) 0.65662(9) 0.54824(10) 0.0336(3) Uani d . . . 1 . .
C C9 0.13413(8) 0.69250(9) 0.61837(10) 0.0351(3) Uani d . . . 1 . .
H H9 0.151596 0.677746 0.694907 0.042 Uiso calc U . R 1 . .
C C10 0.07954(9) 0.74982(9) 0.57502(11) 0.0366(3) Uani d . . . 1 . .
C C11 0.05302(9) 0.76922(10) 0.46100(11) 0.0383(3) Uani d . . . 1 . .
H H11 0.015027 0.807954 0.430546 0.046 Uiso calc U . R 1 . .
C C12 0.08275(8) 0.73143(10) 0.39399(11) 0.0366(3) Uani d . . . 1 . .
H H12 0.064552 0.744541 0.317028 0.044 Uiso calc U . R 1 . .
C C13 0.39765(8) 0.51150(9) 0.41164(9) 0.0323(3) Uani d . . . 1 . .
C C14 0.07990(11) 0.78049(12) 0.75378(13) 0.0488(4) Uani d . . . 1 . .
H H14A 0.058409 0.821336 0.790368 0.073 Uiso calc U . R 1 . .
H H14B 0.127286 0.796437 0.777655 0.073 Uiso calc U . R 1 . .
H H14C 0.075507 0.716248 0.773657 0.073 Uiso calc U . R 1 . .
C C15 0.12026(7) 0.45690(9) 0.37805(10) 0.0285(3) Uani d . . . 1 . .
C C16 0.17497(7) 0.39921(10) 0.42287(11) 0.0299(3) Uani d . . . 1 . .
H H16 0.210866 0.403581 0.397901 0.036 Uiso calc U . R 1 . .
C C17 0.17806(7) 0.33483(9) 0.50409(10) 0.0273(3) Uani d . . . 1 . .
H H17 0.21606 0.296178 0.535107 0.033 Uiso calc U . R 1 . .
C C18 0.12508(6) 0.32777(8) 0.53918(9) 0.0233(2) Uani d . . . 1 . .
C C19 0.06987(6) 0.38544(9) 0.49499(10) 0.0248(2) Uani d . . . 1 . .
H H19 0.033807 0.38059 0.519495 0.03 Uiso calc U . R 1 . .
C C20 0.06760(7) 0.45004(9) 0.41505(10) 0.0265(3) Uani d . . . 1 . .
H H20 0.030089 0.489736 0.38538 0.032 Uiso calc U . R 1 . .
C C21 0.17526(7) 0.20030(9) 0.65680(11) 0.0320(3) Uani d . . . 1 . .
H H21A 0.167272 0.15941 0.710393 0.048 Uiso calc U . R 1 . .
H H21B 0.218082 0.231979 0.692361 0.048 Uiso calc U . R 1 . .
H H21C 0.176345 0.163763 0.594278 0.048 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C15 . 1.7670(13) ?
S1 C6 . 1.8810(13) ?
O1 C5 . 1.3642(18) ?
O1 C8 . 1.3853(18) ?
O2 C10 . 1.363(2) ?
O2 C14 . 1.4323(18) ?
O3 C18 . 1.3676(14) ?
O3 C21 . 1.4278(17) ?
N1 C5 . 1.3280(19) ?
N1 C1 . 1.335(2) ?
N2 C1 . 1.345(2) ?
N2 H2A . 0.884(16) ?
N2 H2B . 0.897(17) ?
N3 C13 . 1.149(2) ?
N4 C3 . 1.3684(15) ?
N4 H4A . 0.883(17) ?
N4 H4B . 0.867(15) ?
C1 C2 . 1.4212(15) ?
C2 C3 . 1.404(2) ?
C2 C13 . 1.417(2) ?
C3 C4 . 1.408(2) ?
C4 C5 . 1.3941(16) ?
C4 C6 . 1.490(2) ?
C6 C7 . 1.499(2) ?
C6 H6 . 1.0 ?
C7 C8 . 1.3849(17) ?
C7 C12 . 1.398(2) ?
C8 C9 . 1.391(2) ?
C9 C10 . 1.379(2) ?
C9 H9 . 0.95 ?
C10 C11 . 1.4073(19) ?
C11 C12 . 1.378(2) ?
C11 H11 . 0.95 ?
C12 H12 . 0.95 ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C15 C16 . 1.386(2) ?
C15 C20 . 1.3973(19) ?
C16 C17 . 1.3941(19) ?
C16 H16 . 0.95 ?
C17 C18 . 1.3881(18) ?
C17 H17 . 0.95 ?
C18 C19 . 1.3921(18) ?
C19 C20 . 1.3882(17) ?
C19 H19 . 0.95 ?
C20 H20 . 0.95 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C15 S1 C6 . . 99.49(6) ?
C5 O1 C8 . . 118.64(10) ?
C10 O2 C14 . . 116.06(13) ?
C18 O3 C21 . . 117.14(10) ?
C5 N1 C1 . . 116.77(11) ?
C1 N2 H2A . . 116.1(13) ?
C1 N2 H2B . . 120.3(14) ?
H2A N2 H2B . . 119.7(19) ?
C3 N4 H4A . . 116.5(15) ?
C3 N4 H4B . . 116.1(13) ?
H4A N4 H4B . . 115.(2) ?
N1 C1 N2 . . 117.33(11) ?
N1 C1 C2 . . 121.83(14) ?
N2 C1 C2 . . 120.81(14) ?
C3 C2 C13 . . 121.55(11) ?
C3 C2 C1 . . 119.53(14) ?
C13 C2 C1 . . 118.92(13) ?
N4 C3 C2 . . 120.38(14) ?
N4 C3 C4 . . 121.11(14) ?
C2 C3 C4 . . 118.51(11) ?
C5 C4 C3 . . 115.70(14) ?
C5 C4 C6 . . 121.08(13) ?
C3 C4 C6 . . 123.07(11) ?
N1 C5 O1 . . 110.81(10) ?
N1 C5 C4 . . 127.38(14) ?
O1 C5 C4 . . 121.81(14) ?
C4 C6 C7 . . 111.76(10) ?
C4 C6 S1 . . 111.93(10) ?
C7 C6 S1 . . 110.82(10) ?
C4 C6 H6 . . 107.4 ?
C7 C6 H6 . . 107.4 ?
S1 C6 H6 . . 107.4 ?
C8 C7 C12 . . 116.89(14) ?
C8 C7 C6 . . 120.10(14) ?
C12 C7 C6 . . 122.98(12) ?
C7 C8 O1 . . 122.51(14) ?
C7 C8 C9 . . 122.79(15) ?
O1 C8 C9 . . 114.68(11) ?
C10 C9 C8 . . 118.94(12) ?
C10 C9 H9 . . 120.5 ?
C8 C9 H9 . . 120.5 ?
O2 C10 C9 . . 124.03(12) ?
O2 C10 C11 . . 115.97(14) ?
C9 C10 C11 . . 120.00(15) ?
C12 C11 C10 . . 119.31(15) ?
C12 C11 H11 . . 120.3 ?
C10 C11 H11 . . 120.3 ?
C11 C12 C7 . . 122.03(12) ?
C11 C12 H12 . . 119.0 ?
C7 C12 H12 . . 119.0 ?
N3 C13 C2 . . 178.78(14) ?
O2 C14 H14A . . 109.5 ?
O2 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O2 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C16 C15 C20 . . 119.25(12) ?
C16 C15 S1 . . 120.65(10) ?
C20 C15 S1 . . 120.10(11) ?
C15 C16 C17 . . 120.92(12) ?
C15 C16 H16 . . 119.5 ?
C17 C16 H16 . . 119.5 ?
C18 C17 C16 . . 119.34(13) ?
C18 C17 H17 . . 120.3 ?
C16 C17 H17 . . 120.3 ?
O3 C18 C17 . . 124.09(12) ?
O3 C18 C19 . . 115.59(11) ?
C17 C18 C19 . . 120.32(11) ?
C20 C19 C18 . . 119.90(12) ?
C20 C19 H19 . . 120.1 ?
C18 C19 H19 . . 120.1 ?
C19 C20 C15 . . 120.26(13) ?
C19 C20 H20 . . 119.9 ?
C15 C20 H20 . . 119.9 ?
O3 C21 H21A . . 109.5 ?
O3 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
O3 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 N2 . . . . 176.88(12) ?
C5 N1 C1 C2 . . . . -4.72(19) ?
N1 C1 C2 C3 . . . . 2.27(19) ?
N2 C1 C2 C3 . . . . -179.38(12) ?
N1 C1 C2 C13 . . . . -176.99(12) ?
N2 C1 C2 C13 . . . . 1.36(19) ?
C13 C2 C3 N4 . . . . 1.65(19) ?
C1 C2 C3 N4 . . . . -177.59(12) ?
C13 C2 C3 C4 . . . . -177.96(12) ?
C1 C2 C3 C4 . . . . 2.80(18) ?
N4 C3 C4 C5 . . . . 175.46(12) ?
C2 C3 C4 C5 . . . . -4.93(18) ?
N4 C3 C4 C6 . . . . -0.04(19) ?
C2 C3 C4 C6 . . . . 179.57(12) ?
C1 N1 C5 O1 . . . . -178.04(11) ?
C1 N1 C5 C4 . . . . 2.3(2) ?
C8 O1 C5 N1 . . . . 165.51(11) ?
C8 O1 C5 C4 . . . . -14.82(18) ?
C3 C4 C5 N1 . . . . 2.6(2) ?
C6 C4 C5 N1 . . . . 178.16(13) ?
C3 C4 C5 O1 . . . . -177.03(12) ?
C6 C4 C5 O1 . . . . -1.4(2) ?
C5 C4 C6 C7 . . . . 17.04(17) ?
C3 C4 C6 C7 . . . . -167.70(12) ?
C5 C4 C6 S1 . . . . -107.94(13) ?
C3 C4 C6 S1 . . . . 67.32(14) ?
C15 S1 C6 C4 . . . . 58.29(11) ?
C15 S1 C6 C7 . . . . -67.20(11) ?
C4 C6 C7 C8 . . . . -17.84(17) ?
S1 C6 C7 C8 . . . . 107.75(13) ?
C4 C6 C7 C12 . . . . 164.01(12) ?
S1 C6 C7 C12 . . . . -70.40(14) ?
C12 C7 C8 O1 . . . . -178.35(12) ?
C6 C7 C8 O1 . . . . 3.4(2) ?
C12 C7 C8 C9 . . . . 0.3(2) ?
C6 C7 C8 C9 . . . . -177.99(13) ?
C5 O1 C8 C7 . . . . 13.87(19) ?
C5 O1 C8 C9 . . . . -164.85(12) ?
C7 C8 C9 C10 . . . . -1.4(2) ?
O1 C8 C9 C10 . . . . 177.32(12) ?
C14 O2 C10 C9 . . . . 6.4(2) ?
C14 O2 C10 C11 . . . . -173.01(13) ?
C8 C9 C10 O2 . . . . -177.65(13) ?
C8 C9 C10 C11 . . . . 1.7(2) ?
O2 C10 C11 C12 . . . . 178.49(12) ?
C9 C10 C11 C12 . . . . -0.9(2) ?
C10 C11 C12 C7 . . . . -0.2(2) ?
C8 C7 C12 C11 . . . . 0.6(2) ?
C6 C7 C12 C11 . . . . 178.76(13) ?
C6 S1 C15 C16 . . . . -79.70(12) ?
C6 S1 C15 C20 . . . . 100.62(11) ?
C20 C15 C16 C17 . . . . -0.07(19) ?
S1 C15 C16 C17 . . . . -179.75(10) ?
C15 C16 C17 C18 . . . . 0.92(19) ?
C21 O3 C18 C17 . . . . -7.23(16) ?
C21 O3 C18 C19 . . . . 173.61(10) ?
C16 C17 C18 O3 . . . . 179.85(11) ?
C16 C17 C18 C19 . . . . -1.03(18) ?
O3 C18 C19 C20 . . . . 179.50(10) ?
C17 C18 C19 C20 . . . . 0.31(18) ?
C18 C19 C20 C15 . . . . 0.55(18) ?
C16 C15 C20 C19 . . . . -0.66(18) ?
S1 C15 C20 C19 . . . . 179.02(9) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2A N3 6_566 0.884(16) 2.165(17) 3.0441(15) 173.0(18) ?
N2 H2B N3 5_666 0.897(17) 2.225(18) 3.084(2) 159.9(19) ?
N4 H4A N1 6_565 0.883(17) 2.380(19) 3.2013(18) 155.(2) ?
N4 H4B S1 . 0.867(15) 2.689(17) 3.3474(16) 133.6(16) ?

