# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

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

data_4sepe_0m
_database_code_depnum_ccdc_archive 'CCDC 1566113'
_audit_update_record             
;
2017-08-02 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;
_audit_creation_date             2016-09-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H15 N3'
_chemical_formula_sum            'C12 H15 N3'
_chemical_formula_weight         201.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.3134(8)
_cell_length_b                   12.5189(13)
_cell_length_c                   11.0332(12)
_cell_angle_alpha                90
_cell_angle_beta                 107.377(3)
_cell_angle_gamma                90
_cell_volume                     1095.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2806
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.17
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1539 before and 0.0549 after correction.
The Ratio of minimum to maximum transmission is 0.8423.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8589
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.021
_diffrn_reflns_theta_max         25.021
_diffrn_reflns_theta_min         2.714
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1404
_reflns_number_total             1924
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         1924
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0548P)²+0.1070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1060
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C5(H5), C6(H6), C8(H8)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.20615(16) 0.43328(10) 0.51418(12) 0.0218(3) Uani 1 1 d . . . . .
N2 N 0.42483(17) 0.44060(10) 0.71658(12) 0.0228(4) Uani 1 1 d . . . . .
N3 N 0.15807(19) 0.51032(11) 0.68883(13) 0.0227(4) Uani 1 1 d . . . . .
H3 H 0.063(2) 0.5238(14) 0.6339(17) 0.029(5) Uiso 1 1 d . . . . .
C1 C 0.2705(2) 0.46020(12) 0.64219(15) 0.0208(4) Uani 1 1 d . . . . .
C2 C 0.5338(2) 0.39374(12) 0.66108(15) 0.0212(4) Uani 1 1 d . . . . .
C3 C 0.7010(2) 0.37141(12) 0.73358(16) 0.0245(4) Uani 1 1 d . . . . .
H3A H 0.7369 0.3860 0.8221 0.029 Uiso 1 1 calc R . . . .
C4 C 0.8116(2) 0.32882(13) 0.67656(16) 0.0273(4) Uani 1 1 d . . . . .
H4 H 0.9243 0.3148 0.7263 0.033 Uiso 1 1 calc R . . . .
C5 C 0.7621(2) 0.30532(13) 0.54584(16) 0.0267(4) Uani 1 1 d . . . . .
H5 H 0.8409 0.2765 0.5077 0.032 Uiso 1 1 calc R . . . .
C6 C 0.6004(2) 0.32429(12) 0.47463(16) 0.0243(4) Uani 1 1 d . . . . .
H6 H 0.5659 0.3079 0.3865 0.029 Uiso 1 1 calc R . . . .
C7 C 0.4842(2) 0.36784(12) 0.53043(15) 0.0205(4) Uani 1 1 d . . . . .
C8 C 0.3138(2) 0.38975(13) 0.46396(15) 0.0232(4) Uani 1 1 d . . . . .
H8 H 0.2750 0.3715 0.3765 0.028 Uiso 1 1 calc R . . . .
C9 C 0.1906(2) 0.55281(13) 0.81892(14) 0.0220(4) Uani 1 1 d . . . . .
C10 C 0.2405(2) 0.46199(14) 0.91600(15) 0.0290(4) Uani 1 1 d . . . . .
H10A H 0.1485 0.4098 0.8998 0.044 Uiso 1 1 calc GR . . . .
H10B H 0.2623 0.4911 1.0019 0.044 Uiso 1 1 calc GR . . . .
H10C H 0.3424 0.4269 0.9084 0.044 Uiso 1 1 calc GR . . . .
C11 C 0.3263(2) 0.63931(14) 0.84683(16) 0.0282(4) Uani 1 1 d . . . . .
H11A H 0.4319 0.6088 0.8401 0.042 Uiso 1 1 calc GR . . . .
H11B H 0.3439 0.6670 0.9329 0.042 Uiso 1 1 calc GR . . . .
H11C H 0.2902 0.6976 0.7854 0.042 Uiso 1 1 calc GR . . . .
C12 C 0.0260(2) 0.60226(14) 0.82479(16) 0.0286(4) Uani 1 1 d . . . . .
H12A H -0.0054 0.6610 0.7635 0.043 Uiso 1 1 calc GR . . . .
H12B H 0.0402 0.6297 0.9105 0.043 Uiso 1 1 calc GR . . . .
H12C H -0.0630 0.5479 0.8041 0.043 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.394(2) . ?
N1 C8 1.304(2) . ?
N2 C1 1.323(2) . ?
N2 C2 1.368(2) . ?
N3 H3 0.854(19) . ?
N3 C1 1.349(2) . ?
N3 C9 1.478(2) . ?
C2 C3 1.409(2) . ?
C2 C7 1.414(2) . ?
C3 H3A 0.9500 . ?
C3 C4 1.368(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.408(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.360(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.401(2) . ?
C7 C8 1.414(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.532(2) . ?
C9 C11 1.527(2) . ?
C9 C12 1.521(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
C8 N1 C1 115.28(14) . . ?
C1 N2 C2 116.81(14) . . ?
C1 N3 H3 114.7(11) . . ?
C1 N3 C9 126.26(15) . . ?
C9 N3 H3 118.7(11) . . ?
N2 C1 N1 126.23(15) . . ?
N2 C1 N3 120.24(15) . . ?
N3 C1 N1 113.52(15) . . ?
N2 C2 C3 120.25(15) . . ?
N2 C2 C7 121.64(15) . . ?
C3 C2 C7 118.10(15) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 C2 120.06(16) . . ?
C4 C3 H3A 120.0 . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.44(16) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.43(16) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.40(16) . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C8 115.22(15) . . ?
C6 C7 C2 120.54(16) . . ?
C6 C7 C8 124.24(15) . . ?
N1 C8 C7 124.68(15) . . ?
N1 C8 H8 117.7 . . ?
C7 C8 H8 117.7 . . ?
N3 C9 C10 110.16(13) . . ?
N3 C9 C11 111.14(13) . . ?
N3 C9 C12 106.38(13) . . ?
C11 C9 C10 110.84(13) . . ?
C12 C9 C10 109.36(14) . . ?
C12 C9 C11 108.84(13) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
N2 C2 C3 C4 -177.15(14) . . . . ?
N2 C2 C7 C6 177.11(14) . . . . ?
N2 C2 C7 C8 -2.5(2) . . . . ?
C1 N1 C8 C7 1.1(2) . . . . ?
C1 N2 C2 C3 179.27(14) . . . . ?
C1 N2 C2 C7 0.3(2) . . . . ?
C1 N3 C9 C10 -61.9(2) . . . . ?
C1 N3 C9 C11 61.3(2) . . . . ?
C1 N3 C9 C12 179.65(15) . . . . ?
C2 N2 C1 N1 3.1(2) . . . . ?
C2 N2 C1 N3 -177.21(14) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C2 C7 C8 N1 1.8(2) . . . . ?
C3 C2 C7 C6 -1.9(2) . . . . ?
C3 C2 C7 C8 178.44(14) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C4 C5 C6 C7 0.6(2) . . . . ?
C5 C6 C7 C2 0.7(2) . . . . ?
C5 C6 C7 C8 -179.73(15) . . . . ?
C6 C7 C8 N1 -177.80(15) . . . . ?
C7 C2 C3 C4 1.9(2) . . . . ?
C8 N1 C1 N2 -3.8(2) . . . . ?
C8 N1 C1 N3 176.52(13) . . . . ?
C9 N3 C1 N1 -177.14(13) . . . . ?
C9 N3 C1 N2 3.1(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_SCA_A118_022_0m
_database_code_depnum_ccdc_archive 'CCDC 1566284'
_audit_update_record             
;
2017-08-02 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;
_audit_creation_date             2016-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H22 N4 O2 S'
_chemical_formula_sum            'C19 H22 N4 O2 S'
_chemical_formula_weight         370.48
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.8633(6)
_cell_length_b                   9.3267(7)
_cell_length_c                   13.5742(10)
_cell_angle_alpha                84.166(4)
_cell_angle_beta                 89.184(4)
_cell_angle_gamma                79.543(4)
_cell_volume                     973.90(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9835
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.95
_cell_measurement_theta_min      3.93
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2633
_exptl_crystal_F_000             392.4005
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_description       block
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.12
_diffrn_reflns_av_unetI/netI     0.1059
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22709
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.51
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3130
_reflns_number_total             3626
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2008 (Burla et al., 2007)'
_refine_diff_density_max         0.6866
_refine_diff_density_min         -1.4579
_refine_diff_density_rms         0.2762
_refine_ls_d_res_high            0.8255
_refine_ls_d_res_low             13.5038
_refine_ls_goodness_of_fit_ref   1.1298
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3626
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0858
_refine_ls_restrained_S_all      1.1298
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2398
_refine_ls_wR_factor_ref         0.2778
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13),
 N1(H1), C19(H19)
2.b Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C17(H17a,H17b,H17c), C18(H18a,H18b,H18c), C1(H1a,H1b,H1c)
;
_atom_sites_solution_primary     direct
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.4, Nqual =  -1, Ralpha = 0.095
;
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_refinement_flags_posn
S1 S 0.20479(8) 0.96809(6) 0.86355(4) 0.0408(3) Uani 1.000000 .
O1 O 0.2576(3) 0.9421(2) 0.96585(14) 0.0532(6) Uani 1.000000 .
O2 O 0.1108(3) 0.8683(2) 0.82494(16) 0.0575(6) Uani 1.000000 .
N1 N 0.2100(3) 1.3277(2) 0.72778(17) 0.0496(6) Uani 1.000000 .
H1 H 0.1701(3) 1.2534(2) 0.71149(17) 0.0596(7) Uiso 1.000000 R
N2 N 0.2650(3) 1.4525(2) 0.86028(16) 0.0428(6) Uani 1.000000 .
N3 N 0.0856(3) 1.1262(2) 0.83798(16) 0.0421(6) Uani 1.000000 .
N4 N 0.1468(2) 1.2350(2) 0.88469(15) 0.0362(5) Uani 1.000000 .
C1 C 0.8490(5) 0.9963(6) 0.6159(3) 0.0992(15) Uani 1.000000 .
H1a H 0.862(2) 1.0971(7) 0.606(2) 0.149(2) Uiso 1.000000 GR
H1b H 0.9499(8) 0.939(3) 0.6487(12) 0.149(2) Uiso 1.000000 GR
H1c H 0.835(2) 0.961(4) 0.5530(10) 0.149(2) Uiso 1.000000 GR
C2 C 0.2124(3) 1.3435(3) 0.82432(19) 0.0396(6) Uani 1.000000 .
C3 C 0.3012(3) 1.5830(3) 0.9991(2) 0.0489(7) Uani 1.000000 .
H3 H 0.3472(3) 1.6526(3) 0.9583(2) 0.0587(8) Uiso 1.000000 R
C4 C 0.2511(3) 1.4635(3) 0.95898(19) 0.0391(6) Uani 1.000000 .
C5 C 0.1835(3) 1.3587(3) 1.02344(19) 0.0398(6) Uani 1.000000 .
C6 C 0.1654(4) 1.3759(3) 1.1253(2) 0.0513(7) Uani 1.000000 .
H6 H 0.1190(4) 1.3083(3) 1.1677(2) 0.0615(9) Uiso 1.000000 R
C7 C 0.5368(3) 1.0134(3) 0.8325(2) 0.0454(6) Uani 1.000000 .
H7 H 0.5334(3) 1.0381(3) 0.8973(2) 0.0544(8) Uiso 1.000000 R
C8 C 0.2163(4) 1.4924(4) 1.1608(2) 0.0580(8) Uani 1.000000 .
H8 H 0.2075(4) 1.5030(4) 1.2282(2) 0.0696(10) Uiso 1.000000 R
C9 C 0.3967(3) 0.9670(3) 0.79369(19) 0.0413(6) Uani 1.000000 .
C10 C 0.2819(4) 1.5963(3) 1.0972(3) 0.0570(8) Uani 1.000000 .
H10 H 0.3131(4) 1.6766(3) 1.1228(3) 0.0684(10) Uiso 1.000000 R
C11 C 0.6809(4) 1.0232(4) 0.7755(2) 0.0565(8) Uani 1.000000 .
H11 H 0.7734(4) 1.0571(4) 0.8012(2) 0.0678(9) Uiso 1.000000 R
C12 C 0.4020(4) 0.9269(4) 0.6989(2) 0.0608(8) Uani 1.000000 .
H12 H 0.3083(4) 0.8948(4) 0.6730(2) 0.0730(10) Uiso 1.000000 R
C13 C 0.5482(4) 0.9348(5) 0.6427(2) 0.0726(10) Uani 1.000000 .
H13 H 0.5526(4) 0.9073(5) 0.5786(2) 0.0872(12) Uiso 1.000000 R
C14 C 0.2680(4) 1.4230(4) 0.6463(2) 0.0592(8) Uani 1.000000 .
C15 C 0.6891(4) 0.9831(4) 0.6801(2) 0.0646(9) Uani 1.000000 .
C16 C 0.4591(5) 1.4290(6) 0.6589(3) 0.0953(14) Uani 1.000000 .
H16a H 0.4770(8) 1.461(3) 0.7223(10) 0.143(2) Uiso 1.000000 GR
H16b H 0.5269(6) 1.3333(9) 0.655(2) 0.143(2) Uiso 1.000000 GR
H16c H 0.4934(12) 1.496(3) 0.6076(14) 0.143(2) Uiso 1.000000 GR
C17 C 0.1590(6) 1.5771(4) 0.6427(3) 0.0807(11) Uani 1.000000 .
H17a H 0.0386(6) 1.5710(5) 0.640(2) 0.1210(17) Uiso 1.000000 GR
H17b H 0.181(3) 1.6212(13) 0.7011(10) 0.1210(17) Uiso 1.000000 GR
H17c H 0.189(3) 1.6357(10) 0.5851(12) 0.1210(17) Uiso 1.000000 GR
C18 C 0.2394(6) 1.3540(5) 0.5532(2) 0.0864(13) Uani 1.000000 .
H18a H 0.317(3) 1.2620(19) 0.5528(13) 0.1296(19) Uiso 1.000000 GR
H18b H 0.1224(14) 1.338(4) 0.5514(13) 0.1296(19) Uiso 1.000000 GR
H18c H 0.260(4) 1.4181(18) 0.4962(2) 0.1296(19) Uiso 1.000000 GR
C19 C 0.1294(3) 1.2455(3) 0.98094(18) 0.0407(6) Uani 1.000000 .
H19 H 0.0804(3) 1.1764(3) 1.02042(18) 0.0489(7) Uiso 1.000000 R


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 1.4391(19) . ?
S1 O2 1.4306(18) . ?
S1 N3 1.605(2) . ?
S1 C9 1.770(3) . ?
N1 H1 0.8600 . ?
N1 C2 1.334(3) . ?
N1 C14 1.468(4) . ?
N2 C2 1.305(3) . ?
N2 C4 1.355(4) . ?
N3 N4 1.407(3) . ?
N4 C2 1.404(3) . ?
N4 C19 1.324(3) . ?
C1 H1a 0.9600 . ?
C1 H1b 0.9600 . ?
C1 H1c 0.9600 . ?
C1 C15 1.535(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.408(3) . ?
C3 C10 1.354(4) . ?
C4 C5 1.416(4) . ?
C5 C6 1.411(4) . ?
C5 C19 1.387(3) . ?
C6 H6 0.9300 . ?
C6 C8 1.357(4) . ?
C7 H7 0.9300 . ?
C7 C9 1.383(3) . ?
C7 C11 1.375(4) . ?
C8 H8 0.9300 . ?
C8 C10 1.397(5) . ?
C9 C12 1.374(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C15 1.381(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(5) . ?
C13 H13 0.9300 . ?
C13 C15 1.390(5) . ?
C14 C16 1.526(5) . ?
C14 C17 1.530(5) . ?
C14 C18 1.513(5) . ?
C16 H16a 0.9600 . ?
C16 H16b 0.9600 . ?
C16 H16c 0.9600 . ?
C17 H17a 0.9600 . ?
C17 H17b 0.9600 . ?
C17 H17c 0.9600 . ?
C18 H18a 0.9600 . ?
C18 H18b 0.9600 . ?
C18 H18c 0.9600 . ?
C19 H19 0.9300 . ?

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 118.54(12) . . ?
N3 S1 O1 112.39(11) . . ?
N3 S1 O2 104.41(12) . . ?
C9 S1 O1 106.14(12) . . ?
C9 S1 O2 107.80(12) . . ?
C9 S1 N3 107.01(12) . . ?
C2 N1 H1 116.39(14) . . ?
C14 N1 H1 116.39(16) . . ?
C14 N1 C2 127.2(2) . . ?
C4 N2 C2 118.8(2) . . ?
N4 N3 S1 111.56(15) . . ?
C2 N4 N3 117.7(2) . . ?
C19 N4 N3 122.3(2) . . ?
C19 N4 C2 119.7(2) . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?
C15 C1 H1a 109.5 . . ?
C15 C1 H1b 109.5 . . ?
C15 C1 H1c 109.5 . . ?
N2 C2 N1 123.6(2) . . ?
N4 C2 N1 114.1(2) . . ?
N4 C2 N2 122.3(2) . . ?
C4 C3 H3 120.14(16) . . ?
C10 C3 H3 120.14(17) . . ?
C10 C3 C4 119.7(3) . . ?
C3 C4 N2 119.8(2) . . ?
C5 C4 N2 121.6(2) . . ?
C5 C4 C3 118.6(2) . . ?
C6 C5 C4 120.2(2) . . ?
C19 C5 C4 117.1(2) . . ?
C19 C5 C6 122.7(2) . . ?
H6 C6 C5 120.41(16) . . ?
C8 C6 C5 119.2(3) . . ?
C8 C6 H6 120.41(18) . . ?
C9 C7 H7 119.97(15) . . ?
C11 C7 H7 119.97(17) . . ?
C11 C7 C9 120.1(3) . . ?
H8 C8 C6 119.67(18) . . ?
C10 C8 C6 120.7(3) . . ?
C10 C8 H8 119.67(17) . . ?
C7 C9 S1 120.10(19) . . ?
C12 C9 S1 119.4(2) . . ?
C12 C9 C7 120.4(3) . . ?
C8 C10 C3 121.6(3) . . ?
H10 C10 C3 119.19(17) . . ?
H10 C10 C8 119.19(17) . . ?
H11 C11 C7 119.78(17) . . ?
C15 C11 C7 120.4(3) . . ?
C15 C11 H11 119.78(18) . . ?
H12 C12 C9 120.44(17) . . ?
C13 C12 C9 119.1(3) . . ?
C13 C12 H12 120.44(19) . . ?
H13 C13 C12 119.40(19) . . ?
C15 C13 C12 121.2(3) . . ?
C15 C13 H13 119.40(18) . . ?
C16 C14 N1 110.3(3) . . ?
C17 C14 N1 110.0(3) . . ?
C17 C14 C16 110.3(3) . . ?
C18 C14 N1 105.3(3) . . ?
C18 C14 C16 110.7(4) . . ?
C18 C14 C17 110.1(3) . . ?
C11 C15 C1 120.3(3) . . ?
C13 C15 C1 120.9(3) . . ?
C13 C15 C11 118.7(3) . . ?
H16a C16 C14 109.5 . . ?
H16b C16 C14 109.5 . . ?
H16b C16 H16a 109.5 . . ?
H16c C16 C14 109.5 . . ?
H16c C16 H16a 109.5 . . ?
H16c C16 H16b 109.5 . . ?
H17a C17 C14 109.5 . . ?
H17b C17 C14 109.5 . . ?
H17b C17 H17a 109.5 . . ?
H17c C17 C14 109.5 . . ?
H17c C17 H17a 109.5 . . ?
H17c C17 H17b 109.5 . . ?
H18a C18 C14 109.5 . . ?
H18b C18 C14 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 C14 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
C5 C19 N4 120.6(2) . . ?
H19 C19 N4 119.72(14) . . ?
H19 C19 C5 119.72(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SCA_A118_022B_0m
_database_code_depnum_ccdc_archive 'CCDC 1566285'
_audit_update_record             
;
2017-08-02 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;
_audit_creation_date             2016-10-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H23 N4 O3 S'
_chemical_formula_sum            'C19 H23 N4 O3 S'
_chemical_formula_weight         387.49
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   34.877(2)
_cell_length_b                   9.0455(6)
_cell_length_c                   12.9419(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.171(3)
_cell_angle_gamma                90
_cell_volume                     3940.7(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      3.55
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1623 before and 0.0597 after correction.
The Ratio of minimum to maximum transmission is 0.7848.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     colourless
_exptl_crystal_colour_modifier   colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3061
_exptl_crystal_F_000             1641.6894
_exptl_crystal_preparation       'slow evaporation'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_description       block
_exptl_special_details           
;
 block
;
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29018
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         1.21
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.9962
_diffrn_measured_fraction_theta_max 0.9962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              40
_reflns_limit_h_min              -42
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                3384
_reflns_number_total             3651
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2008 (Burla et al., 2007)'
_refine_diff_density_max         0.9525
_refine_diff_density_min         -0.7131
_refine_diff_density_rms         0.1913
_refine_ls_d_res_high            0.8256
_refine_ls_d_res_low             16.8310
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0477
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3651
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.0477
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1690P)²+4.4793P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1728
_refine_ls_wR_factor_ref         0.2088
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14), N2(H2a), N3(H3a),
 N4(H4), C1(H1), C2(H2)
2.b Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C16(H16a,H16b,H16c), C17(H17a,H17b,H17c), C18(H18a,H18b,
 H18c)
;
_atom_sites_solution_primary     direct
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.3, Nqual =  -1, Ralpha = 0.101
;
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_refinement_flags_posn
S1 S 0.391230(15) 0.47014(6) 0.07259(4) 0.0162(3) Uani 1.000000 .
O1 O 0.39759(5) 0.4908(2) 0.18520(13) 0.0252(4) Uani 1.000000 .
O2 O 0.33399(4) 0.18874(16) -0.37779(11) 0.0157(4) Uani 1.000000 .
O3 O 0.38674(5) 0.32525(18) 0.02635(12) 0.0204(4) Uani 1.000000 .
N1 N 0.33385(5) 0.52864(19) -0.08722(14) 0.0146(4) Uani 1.000000 .
N2 N 0.35096(5) 0.5619(2) 0.01826(14) 0.0170(4) Uani 1.000000 .
H2a H 0.34112(5) 0.6263(2) 0.05293(14) 0.0204(5) Uiso 1.000000 R
N3 N 0.35839(5) 0.1361(2) -0.19998(13) 0.0164(4) Uani 1.000000 .
H3a H 0.36076(5) 0.1700(2) -0.13652(13) 0.0196(5) Uiso 1.000000 R
N4 N 0.32292(5) 0.34624(19) -0.24838(13) 0.0132(4) Uani 1.000000 .
H4 H 0.33294(5) 0.36925(19) -0.18234(13) 0.0158(5) Uiso 1.000000 R
C1 C 0.24057(6) 0.5082(3) -0.46005(18) 0.0176(5) Uani 1.000000 .
H1 H 0.22533(6) 0.4861(3) -0.52872(18) 0.0211(6) Uiso 1.000000 R
C2 C 0.25552(6) 0.6667(2) -0.30850(17) 0.0163(5) Uani 1.000000 .
H2 H 0.25035(6) 0.7526(2) -0.27502(17) 0.0195(6) Uiso 1.000000 R
C3 C 0.27016(6) 0.4120(2) -0.40835(16) 0.0147(5) Uani 1.000000 .
H3 H 0.27458(6) 0.3257(2) -0.44261(16) 0.0176(6) Uiso 1.000000 R
C4 C 0.28544(6) 0.5725(2) -0.25337(16) 0.0125(4) Uani 1.000000 .
C5 C 0.42964(6) 0.5604(2) 0.03346(17) 0.0156(5) Uani 1.000000 .
C6 C 0.43424(6) 0.5362(2) -0.06934(17) 0.0162(5) Uani 1.000000 .
H6 H 0.41851(6) 0.4675(2) -0.11488(17) 0.0195(6) Uiso 1.000000 R
C7 C 0.29344(6) 0.4425(2) -0.30560(16) 0.0115(4) Uani 1.000000 .
C8 C 0.37682(6) -0.0086(2) -0.20830(17) 0.0163(5) Uani 1.000000 .
C9 C 0.33819(6) 0.2206(2) -0.28211(16) 0.0120(4) Uani 1.000000 .
C10 C 0.48705(7) 0.7192(3) -0.0340(2) 0.0231(5) Uani 1.000000 .
C11 C 0.46267(7) 0.6166(3) -0.10161(18) 0.0201(5) Uani 1.000000 .
H11 H 0.46572(7) 0.6023(3) -0.17018(18) 0.0241(6) Uiso 1.000000 R
C12 C 0.45326(7) 0.6607(3) 0.10255(18) 0.0212(5) Uani 1.000000 .
H12 H 0.45006(7) 0.6755(3) 0.17092(18) 0.0254(6) Uiso 1.000000 R
C13 C 0.48189(7) 0.7391(3) 0.0678(2) 0.0254(6) Uani 1.000000 .
H13 H 0.49793(7) 0.8065(3) 0.1138(2) 0.0305(7) Uiso 1.000000 R
C14 C 0.23340(6) 0.6370(2) -0.41065(17) 0.0183(5) Uani 1.000000 .
H14 H 0.21384(6) 0.7026(2) -0.44621(17) 0.0219(6) Uiso 1.000000 R
C15 C 0.51775(7) 0.8078(3) -0.0709(2) 0.0340(7) Uani 1.000000 .
H15a H 0.5196(4) 0.7715(15) -0.1392(8) 0.0510(10) Uiso 1.000000 GR
H15b H 0.5101(3) 0.9100(5) -0.0774(16) 0.0510(10) Uiso 1.000000 GR
H15c H 0.54308(15) 0.7982(19) -0.0197(9) 0.0510(10) Uiso 1.000000 GR
C16 C 0.34710(8) -0.1130(3) -0.28060(19) 0.0252(5) Uani 1.000000 .
H16a H 0.3226(2) -0.1120(16) -0.2598(10) 0.0378(8) Uiso 1.000000 GR
H16b H 0.3423(4) -0.0810(13) -0.3536(3) 0.0378(8) Uiso 1.000000 GR
H16c H 0.3577(3) -0.2114(5) -0.2738(12) 0.0378(8) Uiso 1.000000 GR
C17 C 0.41317(7) 0.0111(3) -0.2507(2) 0.0278(6) Uani 1.000000 .
H17a H 0.40525(10) 0.051(2) -0.3219(6) 0.0417(9) Uiso 1.000000 GR
H17b H 0.4314(3) 0.0778(17) -0.2050(9) 0.0417(9) Uiso 1.000000 GR
H17c H 0.4258(3) -0.0828(5) -0.2520(15) 0.0417(9) Uiso 1.000000 GR
C18 C 0.38849(7) -0.0691(3) -0.09443(19) 0.0243(5) Uani 1.000000 .
H18a H 0.4056(5) 0.0003(10) -0.0482(3) 0.0365(8) Uiso 1.000000 GR
H18b H 0.36503(8) -0.084(2) -0.0702(6) 0.0365(8) Uiso 1.000000 GR
H18c H 0.4022(5) -0.1614(11) -0.0932(3) 0.0365(8) Uiso 1.000000 GR
C19 C 0.30586(6) 0.6116(2) -0.14337(16) 0.0148(5) Uani 1.000000 .


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 1.4279(17) . ?
S1 O3 1.4322(17) . ?
S1 N2 1.6245(18) . ?
S1 C5 1.753(2) . ?
O2 C9 1.242(2) . ?
N1 N2 1.372(2) . ?
N1 C19 1.294(3) . ?
N2 H2a 0.8600 . ?
N3 H3a 0.8600 . ?
N3 C8 1.475(3) . ?
N3 C9 1.348(3) . ?
N4 H4 0.8600 . ?
N4 C7 1.402(3) . ?
N4 C9 1.374(3) . ?
C1 H1 0.9300 . ?
C1 C3 1.382(3) . ?
C1 C14 1.383(3) . ?
C2 H2 0.9300 . ?
C2 C4 1.391(3) . ?
C2 C14 1.372(3) . ?
C3 H3 0.9300 . ?
C3 C7 1.392(3) . ?
C4 C7 1.420(3) . ?
C4 C19 1.459(3) . ?
C5 C6 1.398(3) . ?
C5 C12 1.385(3) . ?
C6 H6 0.9300 . ?
C6 C11 1.380(3) . ?
C8 C16 1.527(3) . ?
C8 C17 1.518(3) . ?
C8 C18 1.524(3) . ?
C10 C11 1.400(3) . ?
C10 C13 1.387(4) . ?
C10 C15 1.512(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.392(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15a 0.9600 . ?
C15 H15b 0.9600 . ?
C15 H15c 0.9600 . ?
C16 H16a 0.9600 . ?
C16 H16b 0.9600 . ?
C16 H16c 0.9600 . ?
C17 H17a 0.9600 . ?
C17 H17b 0.9600 . ?
C17 H17c 0.9600 . ?
C18 H18a 0.9600 . ?
C18 H18b 0.9600 . ?
C18 H18c 0.9600 . ?

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
O3 S1 O1 121.13(10) . . ?
N2 S1 O1 105.11(10) . . ?
N2 S1 O3 107.40(10) . . ?
C5 S1 O1 107.92(11) . . ?
C5 S1 O3 108.28(10) . . ?
C5 S1 N2 106.06(10) . . ?
C19 N1 N2 119.95(17) . . ?
N1 N2 S1 114.85(14) . . ?
H2a N2 S1 122.58(6) . . ?
H2a N2 N1 122.58(11) . . ?
C8 N3 H3a 116.80(11) . . ?
C9 N3 H3a 116.80(11) . . ?
C9 N3 C8 126.39(17) . . ?
C7 N4 H4 115.19(11) . . ?
C9 N4 H4 115.19(11) . . ?
C9 N4 C7 129.62(17) . . ?
C3 C1 H1 119.69(13) . . ?
C14 C1 H1 119.69(12) . . ?
C14 C1 C3 120.6(2) . . ?
C4 C2 H2 118.94(12) . . ?
C14 C2 H2 118.94(13) . . ?
C14 C2 C4 122.1(2) . . ?
H3 C3 C1 119.58(13) . . ?
C7 C3 C1 120.8(2) . . ?
C7 C3 H3 119.58(12) . . ?
C7 C4 C2 118.54(19) . . ?
C19 C4 C2 117.45(19) . . ?
C19 C4 C7 123.98(19) . . ?
C6 C5 S1 119.26(17) . . ?
C12 C5 S1 119.30(17) . . ?
C12 C5 C6 121.3(2) . . ?
H6 C6 C5 120.79(13) . . ?
C11 C6 C5 118.4(2) . . ?
C11 C6 H6 120.79(13) . . ?
C3 C7 N4 123.03(19) . . ?
C4 C7 N4 118.12(18) . . ?
C4 C7 C3 118.74(19) . . ?
C16 C8 N3 110.76(18) . . ?
C17 C8 N3 110.06(19) . . ?
C17 C8 C16 110.4(2) . . ?
C18 C8 N3 105.03(18) . . ?
C18 C8 C16 109.7(2) . . ?
C18 C8 C17 110.79(19) . . ?
N3 C9 O2 123.74(19) . . ?
N4 C9 O2 123.66(18) . . ?
N4 C9 N3 112.60(17) . . ?
C13 C10 C11 118.1(2) . . ?
C15 C10 C11 121.2(2) . . ?
C15 C10 C13 120.7(2) . . ?
C10 C11 C6 121.8(2) . . ?
H11 C11 C6 119.09(13) . . ?
H11 C11 C10 119.09(14) . . ?
H12 C12 C5 120.62(14) . . ?
C13 C12 C5 118.8(2) . . ?
C13 C12 H12 120.62(14) . . ?
C12 C13 C10 121.5(2) . . ?
H13 C13 C10 119.23(14) . . ?
H13 C13 C12 119.23(14) . . ?
C2 C14 C1 119.10(19) . . ?
H14 C14 C1 120.45(12) . . ?
H14 C14 C2 120.45(13) . . ?
H15a C15 C10 109.5 . . ?
H15b C15 C10 109.5 . . ?
H15b C15 H15a 109.5 . . ?
H15c C15 C10 109.5 . . ?
H15c C15 H15a 109.5 . . ?
H15c C15 H15b 109.5 . . ?
H16a C16 C8 109.5 . . ?
H16b C16 C8 109.5 . . ?
H16b C16 H16a 109.5 . . ?
H16c C16 C8 109.5 . . ?
H16c C16 H16a 109.5 . . ?
H16c C16 H16b 109.5 . . ?
H17a C17 C8 109.5 . . ?
H17b C17 C8 109.5 . . ?
H17b C17 H17a 109.5 . . ?
H17c C17 C8 109.5 . . ?
H17c C17 H17a 109.5 . . ?
H17c C17 H17b 109.5 . . ?
H18a C18 C8 109.5 . . ?
H18b C18 C8 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 C8 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
C4 C19 N1 120.74(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rmd_85
_database_code_depnum_ccdc_archive 'CCDC 1566283'
_audit_update_record             
;
2017-08-02 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C26 H28 N4 O4 S'
_chemical_formula_sum            'C26 H28 N4 O4 S'
_chemical_formula_weight         492.58
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   29.7473(8)
_cell_length_b                   10.1292(3)
_cell_length_c                   18.7181(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.7280(10)
_cell_angle_gamma                90.00
_cell_volume                     4945.8(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.37
_cell_measurement_theta_min      3.97
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1449 before and 0.0556 after correction.
The Ratio of minimum to maximum transmission is 0.9247.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2080.0
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            45616
_diffrn_reflns_theta_full        23.59
_diffrn_reflns_theta_max         23.59
_diffrn_reflns_theta_min         4.42
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_number_gt                2960
_reflns_number_total             3519
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2008 (Burla et al., 2007)'
_refine_diff_density_max         1.043
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.282
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         3519
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0515
_refine_ls_restrained_S_all      1.282
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1621
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), N4(H4A)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.34673(9) -0.0891(2) 0.12075(13) 0.0346(6) Uani 1 d . . .
C2 C 0.29526(9) -0.1128(3) 0.07908(15) 0.0448(6) Uani 1 d . . .
H2 H 0.2749 -0.0688 0.0304 0.054 Uiso 1 calc . . R
C3 C 0.27302(10) -0.2028(3) 0.10920(18) 0.0548(8) Uani 1 d . . .
H3 H 0.2380 -0.2200 0.0800 0.066 Uiso 1 calc . . R
C4 C 0.30230(11) -0.2654(3) 0.18087(17) 0.0496(7) Uani 1 d . . .
H4 H 0.2868 -0.3234 0.2010 0.060 Uiso 1 calc . . R
C5 C 0.35517(10) -0.2448(2) 0.22529(16) 0.0411(6) Uani 1 d . . .
C6 C 0.37918(9) -0.1536(2) 0.19536(14) 0.0348(6) Uani 1 d . . .
C7 C 0.43297(9) -0.1372(3) 0.24173(15) 0.0423(6) Uani 1 d . . .
H7 H 0.4498 -0.0802 0.2235 0.051 Uiso 1 calc . . R
C8 C 0.46028(10) -0.2045(3) 0.31295(16) 0.0489(7) Uani 1 d . . .
H8 H 0.4956 -0.1927 0.3424 0.059 Uiso 1 calc . . R
C9 C 0.43674(11) -0.2896(3) 0.34232(17) 0.0548(8) Uani 1 d . . .
H9 H 0.4562 -0.3323 0.3918 0.066 Uiso 1 calc . . R
C10 C 0.38606(11) -0.3112(3) 0.30017(17) 0.0532(7) Uani 1 d . . .
H10 H 0.3709 -0.3704 0.3202 0.064 Uiso 1 calc . . R
C11 C 0.32520(8) -0.1531(2) -0.17816(14) 0.0343(6) Uani 1 d . . .
C12 C 0.30026(10) -0.0978(3) -0.25511(16) 0.0518(7) Uani 1 d . . .
H12 H 0.3015 -0.0069 -0.2610 0.062 Uiso 1 calc . . R
C13 C 0.27368(12) -0.1753(4) -0.32318(17) 0.0651(9) Uani 1 d . . .
H13 H 0.2570 -0.1368 -0.3746 0.078 Uiso 1 calc . . R
C14 C 0.27181(12) -0.3104(3) -0.31485(17) 0.0618(8) Uani 1 d . . .
H14 H 0.2542 -0.3632 -0.3607 0.074 Uiso 1 calc . . R
C15 C 0.29588(10) -0.3659(3) -0.23940(15) 0.0483(7) Uani 1 d . . .
H15 H 0.2941 -0.4568 -0.2340 0.058 Uiso 1 calc . . R
C16 C 0.32327(10) -0.2885(3) -0.16979(17) 0.0540(8) Uani 1 d . . .
C17 C 0.36831(8) -0.2820(2) -0.02928(13) 0.0299(5) Uani 1 d . . .
C18 C 0.35477(8) -0.0724(2) -0.10333(13) 0.0328(5) Uani 1 d . . .
H18 H 0.3354 0.0087 -0.1089 0.039 Uiso 1 calc . . R
C19 C 0.41099(9) -0.0328(2) -0.07818(15) 0.0385(6) Uani 1 d . . .
H19 H 0.4112 0.0450 -0.1091 0.046 Uiso 1 calc . . R
C20 C 0.43183(10) 0.0037(3) 0.01133(16) 0.0455(7) Uani 1 d . . .
H20A H 0.4675 -0.0219 0.0430 0.055 Uiso 1 calc . . R
H20B H 0.4290 0.0979 0.0174 0.055 Uiso 1 calc . . R
C21 C 0.44054(9) -0.1428(3) -0.08995(15) 0.0405(6) Uani 1 d . . .
C22 C 0.45051(19) -0.2638(5) -0.1885(2) 0.0982(15) Uani 1 d . . .
H22A H 0.4352 -0.2692 -0.2467 0.147 Uiso 1 calc . . GR
H22B H 0.4434 -0.3434 -0.1679 0.147 Uiso 1 calc . . GR
H22C H 0.4869 -0.2532 -0.1655 0.147 Uiso 1 calc . . GR
C23 C 0.40059(10) -0.4771(2) 0.06452(15) 0.0431(6) Uani 1 d . . .
C24 C 0.42657(16) -0.5452(4) 0.0210(2) 0.0808(12) Uani 1 d . . .
H24A H 0.4051 -0.5376 -0.0369 0.121 Uiso 1 calc . . GR
H24B H 0.4318 -0.6368 0.0359 0.121 Uiso 1 calc . . GR
H24C H 0.4590 -0.5039 0.0366 0.121 Uiso 1 calc . . GR
C25 C 0.34917(14) -0.5372(3) 0.0438(3) 0.0893(13) Uani 1 d . . .
H25A H 0.3328 -0.4850 0.0675 0.134 Uiso 1 calc . . GR
H25B H 0.3541 -0.6255 0.0650 0.134 Uiso 1 calc . . GR
H25C H 0.3279 -0.5395 -0.0143 0.134 Uiso 1 calc . . GR
C26 C 0.43612(14) -0.4856(3) 0.15620(17) 0.0639(9) Uani 1 d . . .
H26A H 0.4671 -0.4379 0.1702 0.096 Uiso 1 calc . . GR
H26B H 0.4442 -0.5764 0.1718 0.096 Uiso 1 calc . . GR
H26C H 0.4194 -0.4479 0.1843 0.096 Uiso 1 calc . . GR
N1 N 0.34838(7) -0.35265(18) -0.09429(11) 0.0366(5) Uani 1 d . . .
N2 N 0.36087(7) -0.14263(17) -0.03079(11) 0.0292(5) Uani 1 d . . .
N3 N 0.39893(7) -0.07226(19) 0.03837(11) 0.0334(5) Uani 1 d . . .
N4 N 0.39437(8) -0.33517(19) 0.04563(11) 0.0370(5) Uani 1 d . . .
H4A H 0.4086 -0.2814 0.0860 0.044 Uiso 1 calc . . R
O1 O 0.41057(8) 0.10493(18) 0.13578(11) 0.0573(6) Uani 1 d . . .
O2 O 0.32702(8) 0.09450(18) 0.01197(11) 0.0576(6) Uani 1 d . . .
O3 O 0.42963(8) -0.1529(2) -0.16666(12) 0.0636(6) Uani 1 d . . .
O6 O 0.47019(8) -0.2133(2) -0.03690(13) 0.0674(6) Uani 1 d . . .
S1 S 0.36981(2) 0.02739(6) 0.07594(4) 0.0408(3) Uani 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.365(3) . ?
C1 C6 1.419(3) . ?
C1 S1 1.766(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.395(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.355(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.397(4) . ?
C5 C6 1.436(3) . ?
C5 C10 1.422(4) . ?
C6 C7 1.416(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.364(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.380(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.342(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(3) . ?
C11 C16 1.385(4) . ?
C11 C18 1.490(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.361(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.398(4) . ?
C16 N1 1.401(3) . ?
C17 N1 1.285(3) . ?
C17 N2 1.427(3) . ?
C17 N4 1.346(3) . ?
C18 H18 0.9800 . ?
C18 C19 1.556(3) . ?
C18 N2 1.465(3) . ?
C19 H19 0.9800 . ?
C19 C20 1.526(3) . ?
C19 C21 1.500(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 N3 1.511(3) . ?
C21 O3 1.315(3) . ?
C21 O6 1.196(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 O3 1.435(4) . ?
C23 C24 1.531(4) . ?
C23 C25 1.514(4) . ?
C23 C26 1.525(4) . ?
C23 N4 1.470(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
N2 N3 1.434(2) . ?
N3 S1 1.688(2) . ?
N4 H4A 0.8600 . ?
O1 S1 1.4269(19) . ?
O2 S1 1.432(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
C2 C1 C6 121.8(2) . . ?
C2 C1 S1 115.57(18) . . ?
C6 C1 S1 122.62(17) . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.3(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.6(2) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C6 119.5(2) . . ?
C4 C5 C10 121.7(2) . . ?
C10 C5 C6 118.8(2) . . ?
C1 C6 C5 116.7(2) . . ?
C7 C6 C1 125.7(2) . . ?
C7 C6 C5 117.6(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.5(2) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.2 . . ?
C7 C8 C9 121.6(2) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C5 C10 H10 119.5 . . ?
C9 C10 C5 120.9(3) . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C16 119.2(2) . . ?
C12 C11 C18 122.4(2) . . ?
C16 C11 C18 118.4(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.8(3) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C16 121.1(3) . . ?
C16 C15 H15 119.5 . . ?
C11 C16 C15 119.1(2) . . ?
C11 C16 N1 122.8(2) . . ?
C15 C16 N1 118.0(3) . . ?
N1 C17 N2 122.39(19) . . ?
N1 C17 N4 122.4(2) . . ?
N4 C17 N2 115.00(19) . . ?
C11 C18 H18 108.0 . . ?
C11 C18 C19 119.25(19) . . ?
C19 C18 H18 108.0 . . ?
N2 C18 C11 111.02(18) . . ?
N2 C18 H18 108.0 . . ?
N2 C18 C19 102.02(17) . . ?
C18 C19 H19 109.9 . . ?
C20 C19 C18 101.82(18) . . ?
C20 C19 H19 109.9 . . ?
C21 C19 C18 112.63(19) . . ?
C21 C19 H19 109.9 . . ?
C21 C19 C20 112.6(2) . . ?
C19 C20 H20A 110.8 . . ?
C19 C20 H20B 110.8 . . ?
H20A C20 H20B 108.8 . . ?
N3 C20 C19 104.94(18) . . ?
N3 C20 H20A 110.8 . . ?
N3 C20 H20B 110.8 . . ?
O3 C21 C19 111.3(2) . . ?
O6 C21 C19 124.9(2) . . ?
O6 C21 O3 123.8(2) . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
C25 C23 C24 112.9(3) . . ?
C25 C23 C26 109.5(3) . . ?
C26 C23 C24 108.6(2) . . ?
N4 C23 C24 110.5(2) . . ?
N4 C23 C25 109.7(2) . . ?
N4 C23 C26 105.4(2) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C17 N1 C16 118.5(2) . . ?
C17 N2 C18 116.60(17) . . ?
C17 N2 N3 115.22(16) . . ?
N3 N2 C18 106.71(16) . . ?
C20 N3 S1 112.33(16) . . ?
N2 N3 C20 107.95(16) . . ?
N2 N3 S1 109.43(13) . . ?
C17 N4 C23 125.77(19) . . ?
C17 N4 H4A 117.1 . . ?
C23 N4 H4A 117.1 . . ?
C21 O3 C22 117.3(2) . . ?
N3 S1 C1 101.12(10) . . ?
O1 S1 C1 111.86(11) . . ?
O1 S1 N3 104.10(11) . . ?
O1 S1 O2 118.26(12) . . ?
O2 S1 C1 108.78(12) . . ?
O2 S1 N3 111.31(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
C1 C2 C3 C4 1.3(4) . . . . ?
C1 C6 C7 C8 179.8(2) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
C2 C1 C6 C7 178.6(2) . . . . ?
C2 C1 S1 N3 -105.24(19) . . . . ?
C2 C1 S1 O1 144.49(18) . . . . ?
C2 C1 S1 O2 12.0(2) . . . . ?
C2 C3 C4 C5 -1.7(4) . . . . ?
C3 C4 C5 C6 1.1(4) . . . . ?
C3 C4 C5 C10 -179.5(3) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C4 C5 C6 C7 -179.1(2) . . . . ?
C4 C5 C10 C9 -179.6(3) . . . . ?
C5 C6 C7 C8 -1.3(3) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
C6 C1 S1 N3 75.14(19) . . . . ?
C6 C1 S1 O1 -35.1(2) . . . . ?
C6 C1 S1 O2 -167.60(18) . . . . ?
C6 C5 C10 C9 -0.1(4) . . . . ?
C6 C7 C8 C9 -0.3(4) . . . . ?
C7 C8 C9 C10 1.7(4) . . . . ?
C8 C9 C10 C5 -1.5(4) . . . . ?
C10 C5 C6 C1 -179.5(2) . . . . ?
C10 C5 C6 C7 1.5(3) . . . . ?
C11 C12 C13 C14 -0.1(5) . . . . ?
C11 C16 N1 C17 9.5(4) . . . . ?
C11 C18 C19 C20 -161.4(2) . . . . ?
C11 C18 C19 C21 -40.6(3) . . . . ?
C11 C18 N2 C17 36.7(2) . . . . ?
C11 C18 N2 N3 167.08(17) . . . . ?
C12 C11 C16 C15 -0.4(4) . . . . ?
C12 C11 C16 N1 178.6(2) . . . . ?
C12 C11 C18 C19 -83.0(3) . . . . ?
C12 C11 C18 N2 158.9(2) . . . . ?
C12 C13 C14 C15 0.5(5) . . . . ?
C13 C14 C15 C16 -0.9(5) . . . . ?
C14 C15 C16 C11 0.9(4) . . . . ?
C14 C15 C16 N1 -178.1(3) . . . . ?
C15 C16 N1 C17 -171.6(2) . . . . ?
C16 C11 C12 C13 0.0(4) . . . . ?
C16 C11 C18 C19 96.4(3) . . . . ?
C16 C11 C18 N2 -21.7(3) . . . . ?
C17 N2 N3 C20 107.6(2) . . . . ?
C17 N2 N3 S1 -129.90(15) . . . . ?
C18 C11 C12 C13 179.3(3) . . . . ?
C18 C11 C16 C15 -179.7(2) . . . . ?
C18 C11 C16 N1 -0.8(4) . . . . ?
C18 C19 C20 N3 24.9(2) . . . . ?
C18 C19 C21 O3 79.6(3) . . . . ?
C18 C19 C21 O6 -100.2(3) . . . . ?
C18 N2 N3 C20 -23.6(2) . . . . ?
C18 N2 N3 S1 98.93(16) . . . . ?
C19 C18 N2 C17 -91.4(2) . . . . ?
C19 C18 N2 N3 39.0(2) . . . . ?
C19 C20 N3 N2 -2.1(2) . . . . ?
C19 C20 N3 S1 -122.88(18) . . . . ?
C19 C21 O3 C22 -172.8(3) . . . . ?
C20 C19 C21 O3 -166.0(2) . . . . ?
C20 C19 C21 O6 14.2(3) . . . . ?
C20 N3 S1 C1 -168.12(16) . . . . ?
C20 N3 S1 O1 -51.97(18) . . . . ?
C20 N3 S1 O2 76.49(18) . . . . ?
C21 C19 C20 N3 -95.9(2) . . . . ?
C24 C23 N4 C17 58.8(3) . . . . ?
C25 C23 N4 C17 -66.2(3) . . . . ?
C26 C23 N4 C17 176.0(2) . . . . ?
N1 C17 N2 C18 -31.7(3) . . . . ?
N1 C17 N2 N3 -158.0(2) . . . . ?
N1 C17 N4 C23 -4.7(4) . . . . ?
N2 C17 N1 C16 7.2(3) . . . . ?
N2 C17 N4 C23 170.4(2) . . . . ?
N2 C18 C19 C20 -38.8(2) . . . . ?
N2 C18 C19 C21 82.0(2) . . . . ?
N2 N3 S1 C1 72.00(15) . . . . ?
N2 N3 S1 O1 -171.85(14) . . . . ?
N2 N3 S1 O2 -43.39(17) . . . . ?
N4 C17 N1 C16 -178.1(2) . . . . ?
N4 C17 N2 C18 153.20(19) . . . . ?
N4 C17 N2 N3 26.9(2) . . . . ?
O6 C21 O3 C22 7.0(4) . . . . ?
S1 C1 C2 C3 -179.9(2) . . . . ?
S1 C1 C6 C5 179.27(16) . . . . ?
S1 C1 C6 C7 -1.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
