# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_olpy
_database_code_depnum_ccdc_archive 'CCDC 1846921'
_audit_update_record             
;
2018-06-03 deposited with the CCDC.
2018-09-11 downloaded from the CCDC.
;
_audit_creation_date             2018-05-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H14 N4 S, H2 O'
_chemical_formula_sum            'C23 H16 N4 O S'
_chemical_formula_weight         396.47
_chemical_absolute_configuration rm
_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 0.0180 0.0090 '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 0.0310 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3330 0.5570 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   7.8612(3)
_cell_length_b                   9.8518(5)
_cell_length_c                   27.1605(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2103.50(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1880
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      65.5070
_cell_measurement_theta_min      4.7560
_exptl_absorpt_coefficient_mu    1.530
_exptl_absorpt_correction_T_max  0.885
_exptl_absorpt_correction_T_min  0.802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            5023
_diffrn_reflns_theta_full        73.18
_diffrn_reflns_theta_max         73.18
_diffrn_reflns_theta_min         4.77
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2966
_reflns_number_total             3380
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.53(3)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0548
_refine_ls_restrained_S_all      1.092
_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)+(0.0859P)²+0.3456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1558
_refine_ls_wR_factor_ref         0.1638
_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 N(H) groups, All O(H,H) groups
2.a Riding coordinates:
 N1(H1), O1(H1B,H1C)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C12(H12), C17(H17),
 C18(H18), C20(H20), C21(H21), C22(H22), C23(H23)
;
_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
S1 S 0.52983(14) 0.04536(10) 0.10362(4) 0.0842(3) Uani 1 d . . .
N1 N 0.6549(4) -0.2346(3) 0.13683(10) 0.0727(8) Uani 1 d . . .
H1 H 0.7287 -0.2982 0.1406 0.087 Uiso 1 d . . R
N2 N 0.1872(10) -0.5550(8) 0.11115(18) 0.177(3) Uani 1 d . . .
N3 N 0.2401(7) -0.8134(5) -0.01684(19) 0.1136(15) Uani 1 d . . .
N4 N 0.6297(5) -0.4795(5) -0.23395(13) 0.0903(10) Uani 1 d . . .
C1 C 0.6821(5) -0.1732(5) 0.22148(14) 0.0798(11) Uani 1 d . . .
H1A H 0.7245 -0.2593 0.2282 0.096 Uiso 1 calc . . R
C2 C 0.6630(6) -0.0785(6) 0.25943(16) 0.0975(15) Uani 1 d . . .
H2 H 0.6950 -0.1019 0.2913 0.117 Uiso 1 calc . . R
C3 C 0.5981(7) 0.0474(6) 0.25051(18) 0.0989(14) Uani 1 d . . .
H3 H 0.5852 0.1094 0.2761 0.119 Uiso 1 calc . . R
C4 C 0.5514(6) 0.0824(5) 0.20277(19) 0.0911(13) Uani 1 d . . .
H4 H 0.5045 0.1673 0.1966 0.109 Uiso 1 calc . . R
C5 C 0.5743(5) -0.0082(4) 0.16448(15) 0.0754(10) Uani 1 d . . .
C6 C 0.6376(5) -0.1381(4) 0.17365(13) 0.0687(9) Uani 1 d . . .
C7 C 0.5575(4) -0.2327(4) 0.09387(12) 0.0649(8) Uani 1 d . . .
C8 C 0.4954(4) -0.1105(4) 0.07426(13) 0.0673(8) Uani 1 d . . .
C9 C 0.4090(5) -0.1130(4) 0.02936(15) 0.0757(10) Uani 1 d . . .
H9 H 0.3670 -0.0322 0.0164 0.091 Uiso 1 calc . . R
C10 C 0.3844(5) -0.2316(5) 0.00386(15) 0.0774(10) Uani 1 d . . .
H10 H 0.3328 -0.2300 -0.0269 0.093 Uiso 1 calc . . R
C11 C 0.4367(4) -0.3537(4) 0.02400(12) 0.0649(8) Uani 1 d . . .
C12 C 0.5233(4) -0.3539(4) 0.06888(12) 0.0635(7) Uani 1 d . . .
H12 H 0.5589 -0.4359 0.0824 0.076 Uiso 1 calc . . R
C13 C 0.3971(4) -0.4840(4) -0.00096(12) 0.0667(8) Uani 1 d . . .
C14 C 0.3120(5) -0.5831(5) 0.02397(14) 0.0782(10) Uani 1 d . . .
C15 C 0.2436(8) -0.5656(7) 0.07250(19) 0.1162(19) Uani 1 d . . .
C16 C 0.2743(6) -0.7100(5) 0.00148(17) 0.0868(12) Uani 1 d . . .
C17 C 0.4396(4) -0.5059(4) -0.05229(12) 0.0655(8) Uani 1 d . . .
H17 H 0.4026 -0.5864 -0.0666 0.079 Uiso 1 calc . . R
C18 C 0.5272(4) -0.4205(4) -0.08080(12) 0.0642(8) Uani 1 d . . .
H18 H 0.5683 -0.3412 -0.0665 0.077 Uiso 1 calc . . R
C19 C 0.5629(4) -0.4437(4) -0.13342(12) 0.0641(8) Uani 1 d . . .
C20 C 0.5200(6) -0.5614(5) -0.15743(14) 0.0857(11) Uani 1 d . . .
H20 H 0.4679 -0.6321 -0.1405 0.103 Uiso 1 calc . . R
C21 C 0.5551(6) -0.5736(6) -0.20685(17) 0.0946(13) Uani 1 d . . .
H21 H 0.5239 -0.6541 -0.2223 0.113 Uiso 1 calc . . R
C22 C 0.6722(6) -0.3669(6) -0.21040(16) 0.0870(12) Uani 1 d . . .
H22 H 0.7262 -0.2988 -0.2282 0.104 Uiso 1 calc . . R
C23 C 0.6414(5) -0.3442(5) -0.16099(14) 0.0771(10) Uani 1 d . . .
H23 H 0.6734 -0.2626 -0.1465 0.093 Uiso 1 calc . . R
O1 O 0.8095(8) -0.4938(5) 0.16320(13) 0.1465(18) Uani 1 d . . .
H1B H 0.7098 -0.5021 0.1714 0.176 Uiso 1 d . . R
H1C H 0.8507 -0.5554 0.1834 0.176 Uiso 1 d . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C5 1.770(4) . ?
S1 C8 1.751(4) . ?
N1 H1 0.8600 . ?
N1 C6 1.387(5) . ?
N1 C7 1.396(4) . ?
N2 C15 1.144(7) . ?
N3 C16 1.165(6) . ?
N4 C21 1.321(6) . ?
N4 C22 1.324(6) . ?
C1 H1A 0.9300 . ?
C1 C2 1.398(6) . ?
C1 C6 1.389(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.363(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(6) . ?
C5 C6 1.396(6) . ?
C7 C8 1.404(5) . ?
C7 C12 1.399(5) . ?
C8 C9 1.396(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.372(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(6) . ?
C11 C12 1.396(5) . ?
C11 C13 1.485(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.363(6) . ?
C13 C17 1.450(4) . ?
C14 C15 1.434(6) . ?
C14 C16 1.423(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.335(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.474(4) . ?
C19 C20 1.373(6) . ?
C19 C23 1.379(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.376(6) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.382(6) . ?
C23 H23 0.9300 . ?
O1 H1B 0.8188 . ?
O1 H1C 0.8796 . ?

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 S1 C5 101.21(18) . . ?
C6 N1 H1 118.7 . . ?
C6 N1 C7 122.7(3) . . ?
C7 N1 H1 118.7 . . ?
C21 N4 C22 115.5(4) . . ?
C2 C1 H1A 120.1 . . ?
C6 C1 H1A 120.1 . . ?
C6 C1 C2 119.8(5) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.1(5) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.3(5) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.5(5) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 S1 119.0(4) . . ?
C4 C5 C6 120.3(4) . . ?
C6 C5 S1 120.7(3) . . ?
N1 C6 C1 118.6(4) . . ?
N1 C6 C5 122.4(3) . . ?
C1 C6 C5 119.0(4) . . ?
N1 C7 C8 121.3(3) . . ?
N1 C7 C12 120.0(3) . . ?
C12 C7 C8 118.7(3) . . ?
C7 C8 S1 121.7(3) . . ?
C9 C8 S1 119.2(3) . . ?
C9 C8 C7 119.1(3) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.6(3) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 119.4(4) . . ?
C10 C11 C13 120.6(3) . . ?
C12 C11 C13 120.0(3) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 121.1(3) . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C11 119.7(3) . . ?
C14 C13 C17 118.9(4) . . ?
C17 C13 C11 121.3(3) . . ?
C13 C14 C15 123.6(5) . . ?
C13 C14 C16 121.2(4) . . ?
C16 C14 C15 115.0(4) . . ?
N2 C15 C14 178.2(8) . . ?
N3 C16 C14 178.7(6) . . ?
C13 C17 H17 117.2 . . ?
C18 C17 C13 125.6(3) . . ?
C18 C17 H17 117.2 . . ?
C17 C18 H18 117.9 . . ?
C17 C18 C19 124.2(3) . . ?
C19 C18 H18 117.9 . . ?
C20 C19 C18 123.0(3) . . ?
C20 C19 C23 116.9(3) . . ?
C23 C19 C18 120.1(4) . . ?
C19 C20 H20 120.4 . . ?
C19 C20 C21 119.2(4) . . ?
C21 C20 H20 120.4 . . ?
N4 C21 C20 124.8(5) . . ?
N4 C21 H21 117.6 . . ?
C20 C21 H21 117.6 . . ?
N4 C22 H22 117.9 . . ?
N4 C22 C23 124.1(4) . . ?
C23 C22 H22 117.9 . . ?
C19 C23 C22 119.4(4) . . ?
C19 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
H1B O1 H1C 96.6 . . ?

_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_sp1
_database_code_depnum_ccdc_archive 'CCDC 1846922'
_audit_update_record             
;
2018-06-03 deposited with the CCDC.
2018-09-11 downloaded from the CCDC.
;
_audit_creation_date             2018-05-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H11 N3 S2'
_chemical_formula_sum            'C17 H10 N3 S2'
_chemical_formula_weight         320.40
_chemical_absolute_configuration ad
_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 0.0181 0.0091 '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 0.0311 0.0180 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   8.7916(2)
_cell_length_b                   5.62550(10)
_cell_length_c                   14.7562(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.407(2)
_cell_angle_gamma                90.00
_cell_volume                     726.55(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4576
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.9580
_cell_measurement_theta_min      5.0330
_exptl_absorpt_coefficient_mu    3.302
_exptl_absorpt_correction_T_max  0.820
_exptl_absorpt_correction_T_min  0.765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             330
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7554
_diffrn_reflns_theta_full        73.36
_diffrn_reflns_theta_max         73.36
_diffrn_reflns_theta_min         5.05
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2551
_reflns_number_total             2665
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.008(16)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2665
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.037
_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)+(0.0481P)²+0.1014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0834
_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 N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C12(H12), C17(H17)
2.b X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
;
_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 0.2989(3) 0.9972(5) -0.17652(14) 0.0455(5) Uani 1 d . . .
H1 H 0.3626 1.1285 -0.1670 0.055 Uiso 1 calc . . R
C2 C 0.2135(3) 0.9673(5) -0.25978(15) 0.0529(7) Uani 1 d . . .
H2 H 0.2190 1.0799 -0.3055 0.063 Uiso 1 calc . . R
C3 C 0.1209(3) 0.7724(6) -0.27474(15) 0.0547(7) Uani 1 d . . .
H3 H 0.0655 0.7515 -0.3310 0.066 Uiso 1 calc . . R
C4 C 0.1099(3) 0.6075(5) -0.20668(16) 0.0499(6) Uani 1 d . . .
H4 H 0.0455 0.4770 -0.2170 0.060 Uiso 1 calc . . R
C5 C 0.1947(2) 0.6345(4) -0.12213(14) 0.0409(5) Uani 1 d . . .
C6 C 0.2896(2) 0.8321(4) -0.10738(13) 0.0377(4) Uani 1 d . . .
C7 C 0.3217(2) 0.7895(4) 0.05837(12) 0.0346(4) Uani 1 d . . .
C8 C 0.2309(2) 0.5866(4) 0.06118(14) 0.0382(5) Uani 1 d . . .
C9 C 0.1836(3) 0.5143(4) 0.14375(16) 0.0455(5) Uani 1 d . . .
H9 H 0.1214 0.3810 0.1457 0.055 Uiso 1 calc . . R
C10 C 0.2268(3) 0.6361(4) 0.22326(15) 0.0440(5) Uani 1 d . . .
H10 H 0.1976 0.5800 0.2783 0.053 Uiso 1 calc . . R
C11 C 0.3139(2) 0.8426(4) 0.22146(13) 0.0361(5) Uani 1 d . . .
C12 C 0.3590(2) 0.9198(4) 0.13761(13) 0.0351(4) Uani 1 d . . .
H12 H 0.4146 1.0598 0.1349 0.042 Uiso 1 calc . . R
C13 C 0.3590(2) 0.9875(4) 0.30284(13) 0.0376(5) Uani 1 d . . .
C14 C 0.2725(2) 1.0195(4) 0.38117(13) 0.0375(5) Uani 1 d . . .
C15 C 0.1420(2) 0.8890(5) 0.40128(14) 0.0443(5) Uani 1 d . . .
C16 C 0.3319(2) 1.1923(5) 0.44039(13) 0.0427(5) Uani 1 d . . .
C17 C 0.4840(2) 1.1297(5) 0.30972(14) 0.0463(6) Uani 1 d . . .
H17 H 0.5552 1.1309 0.2670 0.056 Uiso 1 calc . . R
N1 N 0.3792(2) 0.8593(4) -0.02349(11) 0.0414(5) Uani 1 d . . .
N2 N 0.0387(2) 0.7881(6) 0.42251(15) 0.0681(7) Uani 1 d . . .
N3 N 0.2773(2) 1.2693(5) 0.51820(12) 0.0542(5) Uani 1 d . . .
H3A H 0.1954 1.2080 0.5358 0.065 Uiso 1 calc . . R
H3B H 0.3246 1.3794 0.5500 0.065 Uiso 1 calc . . R
S1 S 0.18528(7) 0.41566(11) -0.03747(4) 0.05207(17) Uani 1 d . . .
S2 S 0.49857(7) 1.30769(13) 0.40494(4) 0.05394(18) Uani 1 d . . .
H1A H 0.426(2) 0.983(5) -0.0199(15) 0.030(6) Uiso 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 1.389(3) . ?
C1 C6 1.388(3) . ?
C2 C3 1.371(4) . ?
C3 C4 1.378(4) . ?
C4 C5 1.400(3) . ?
C5 C6 1.394(3) . ?
C5 S1 1.762(2) . ?
C6 N1 1.412(2) . ?
C7 C8 1.396(3) . ?
C7 C12 1.393(3) . ?
C7 N1 1.408(2) . ?
C8 C9 1.385(3) . ?
C8 S1 1.759(2) . ?
C9 C10 1.381(3) . ?
C10 C11 1.393(3) . ?
C11 C12 1.403(3) . ?
C11 C13 1.474(3) . ?
C13 C14 1.453(3) . ?
C13 C17 1.355(3) . ?
C14 C15 1.417(3) . ?
C14 C16 1.377(3) . ?
C15 N2 1.139(3) . ?
C16 N3 1.357(3) . ?
C16 S2 1.728(2) . ?
C17 S2 1.720(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 120.3(2) . . ?
C3 C2 C1 120.2(2) . . ?
C2 C3 C4 120.2(2) . . ?
C3 C4 C5 120.5(3) . . ?
C4 C5 S1 120.0(2) . . ?
C6 C5 C4 119.1(2) . . ?
C6 C5 S1 120.91(16) . . ?
C1 C6 C5 119.64(19) . . ?
C1 C6 N1 120.4(2) . . ?
C5 C6 N1 120.0(2) . . ?
C8 C7 N1 120.39(19) . . ?
C12 C7 C8 119.71(18) . . ?
C12 C7 N1 119.9(2) . . ?
C7 C8 S1 120.58(16) . . ?
C9 C8 C7 119.1(2) . . ?
C9 C8 S1 120.24(18) . . ?
C10 C9 C8 121.4(2) . . ?
C9 C10 C11 120.36(19) . . ?
C10 C11 C12 118.45(18) . . ?
C10 C11 C13 123.47(18) . . ?
C12 C11 C13 118.07(18) . . ?
C7 C12 C11 120.91(19) . . ?
C14 C13 C11 126.56(18) . . ?
C17 C13 C11 122.76(18) . . ?
C17 C13 C14 110.4(2) . . ?
C15 C14 C13 126.7(2) . . ?
C16 C14 C13 113.37(19) . . ?
C16 C14 C15 119.94(19) . . ?
N2 C15 C14 176.1(2) . . ?
C14 C16 S2 110.78(15) . . ?
N3 C16 C14 128.3(2) . . ?
N3 C16 S2 120.93(19) . . ?
C13 C17 S2 113.72(16) . . ?
C7 N1 C6 120.43(17) . . ?
C8 S1 C5 100.52(11) . . ?
C17 S2 C16 91.63(11) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
