# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 1855418'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-22 downloaded from the CCDC.
;
_audit_creation_date             2018-06-28
_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         'C17 H14 N2 O2 S'
_chemical_formula_sum            'C17 H14 N2 O2 S'
_chemical_formula_weight         310.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C128 H112 N24 O16 S8 '
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.4456(3)
_cell_length_b                   9.07642(17)
_cell_length_c                   22.7259(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2979.69(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6710
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.3650
_cell_measurement_theta_min      3.8480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.003
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0958
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12918
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.515
_diffrn_reflns_theta_min         3.890
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00 -30.00   0.50    2.60    --  -38.50 126.00  35.00   52
  2  ω    -70.00 -44.00   0.50    2.60    --  -38.50 144.00-156.00   52
  3  ω     49.00  74.00   0.50    2.60    --   49.31-144.00 150.00   50
  4  ω     26.00  98.00   0.50    2.60    --   49.31-126.00 -41.00  144
  5  ω     72.00 117.00   0.50   11.00    --  106.38-126.00 -41.00   90
  6  ω     84.00 169.00   0.50   11.00    --  106.38 144.00-156.00  170
  7  ω    108.00 133.00   0.50   11.00    --  106.38 126.00  35.00   50
  8  ω   -100.00 -36.00   0.50    2.60    --  -38.50 -37.00 150.00  128
  9  ω     38.00 108.00   0.50    2.60    --   49.31  57.00  30.00  140
 10  ω     54.00  82.00   0.50    2.60    --   49.31  37.00 -60.00   56
 11  ω     94.00 120.00   0.50   11.00    --  106.38 -61.00 -60.00   52
 12  ω     46.00  73.00   0.50   11.00    --  106.38 -61.00 -60.00   54
 13  ω     97.00 171.00   0.50   11.00    --  106.38 125.00 120.00  148
 14  ω     48.00  83.00   0.50   11.00    --  106.38 -30.00  90.00   70
 15  ω     39.00 104.00   0.50   11.00    --  106.38 -30.00-120.00  130
 16  ω    103.00 154.00   0.50   11.00    --  106.38  45.00 120.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0045725000
_diffrn_orient_matrix_UB_12      -0.0092635000
_diffrn_orient_matrix_UB_13      0.0676314000
_diffrn_orient_matrix_UB_21      -0.0980376000
_diffrn_orient_matrix_UB_22      0.0666460000
_diffrn_orient_matrix_UB_23      -0.0012414000
_diffrn_orient_matrix_UB_31      -0.0416631000
_diffrn_orient_matrix_UB_32      -0.1558523000
_diffrn_orient_matrix_UB_33      -0.0045328000
_diffrn_oxdiff_ac3_digest_frames 
;
017c25b96c53316d8de0487ea1f250373400027ce8b
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01f1b8e0b9847f2d838da8d74f4d0125d12c62
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2459
_reflns_number_total             3069
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3069
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0930
_refine_ls_restrained_S_all      1.165
_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)+(0.0655P)²+9.6138P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2366
_refine_ls_wR_factor_ref         0.2464
_refine_special_details          ?
_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:
 N1(H1), C4(H4), C7(H7), C17(H17), C13(H13), C16(H16), C15(H15), C14(H14)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
S1 S 0.32594(9) 0.51051(13) 0.47390(6) 0.0495(4) Uani 1 1 d . . . . .
O2 O 0.4736(2) 0.3542(4) 0.70557(15) 0.0563(9) Uani 1 1 d . . . . .
O1 O 0.3803(2) 0.1544(4) 0.65152(16) 0.0557(9) Uani 1 1 d . . . . .
N1 N 0.3766(3) 0.7863(4) 0.43931(18) 0.0514(10) Uani 1 1 d . . . . .
H1 H 0.408638 0.864521 0.445648 0.062 Uiso 1 1 calc R . . . .
C3 C 0.4246(3) 0.5555(5) 0.5681(2) 0.0419(10) Uani 1 1 d . . . . .
C5 C 0.4442(3) 0.3927(5) 0.6505(2) 0.0446(11) Uani 1 1 d . . . . .
C8 C 0.3696(3) 0.4492(5) 0.5411(2) 0.0428(10) Uani 1 1 d . . . . .
C2 C 0.4306(3) 0.6878(5) 0.5337(2) 0.0432(10) Uani 1 1 d . . . . .
C4 C 0.4622(3) 0.5254(5) 0.6239(2) 0.0456(11) Uani 1 1 d . . . . .
H4 H 0.499024 0.595091 0.642710 0.055 Uiso 1 1 calc R . . . .
C12 C 0.3254(3) 0.7830(5) 0.3863(2) 0.0459(11) Uani 1 1 d . . . . .
C6 C 0.3898(3) 0.2845(5) 0.6216(2) 0.0452(11) Uani 1 1 d . . . . .
C7 C 0.3529(3) 0.3131(5) 0.5668(2) 0.0454(11) Uani 1 1 d . . . . .
H7 H 0.317435 0.242584 0.547502 0.054 Uiso 1 1 calc R . . . .
C1 C 0.3809(3) 0.6808(5) 0.4812(2) 0.0441(10) Uani 1 1 d . . . . .
N2 N 0.5271(4) 0.9146(5) 0.5606(2) 0.0697(14) Uani 1 1 d . . . . .
C17 C 0.2377(3) 0.7213(5) 0.3822(2) 0.0514(12) Uani 1 1 d . . . . .
H17 H 0.210492 0.678254 0.415035 0.062 Uiso 1 1 calc R . . . .
C11 C 0.4842(4) 0.8132(5) 0.5489(2) 0.0500(11) Uani 1 1 d . . . . .
C13 C 0.3637(4) 0.8518(6) 0.3377(2) 0.0545(12) Uani 1 1 d . . . . .
H13 H 0.421941 0.895096 0.340279 0.065 Uiso 1 1 calc R . . . .
C16 C 0.1912(4) 0.7242(6) 0.3292(3) 0.0590(14) Uani 1 1 d . . . . .
H16 H 0.133138 0.680568 0.326444 0.071 Uiso 1 1 calc R . . . .
C10 C 0.5385(4) 0.4498(7) 0.7336(3) 0.0664(15) Uani 1 1 d . . . . .
H10A H 0.593322 0.457152 0.709900 0.100 Uiso 1 1 calc GR . . . .
H10B H 0.554340 0.410811 0.771560 0.100 Uiso 1 1 calc GR . . . .
H10C H 0.511501 0.545754 0.738208 0.100 Uiso 1 1 calc GR . . . .
C15 C 0.2293(4) 0.7904(6) 0.2805(3) 0.0644(15) Uani 1 1 d . . . . .
H15 H 0.197708 0.791012 0.244859 0.077 Uiso 1 1 calc R . . . .
C14 C 0.3153(4) 0.8560(7) 0.2853(3) 0.0662(15) Uani 1 1 d . . . . .
H14 H 0.340893 0.903527 0.252899 0.079 Uiso 1 1 calc R . . . .
C9 C 0.3160(4) 0.0501(6) 0.6283(3) 0.0684(16) Uani 1 1 d . . . . .
H9A H 0.335702 0.019983 0.589782 0.103 Uiso 1 1 calc GR . . . .
H9B H 0.255807 0.094431 0.625772 0.103 Uiso 1 1 calc GR . . . .
H9C H 0.313301 -0.034284 0.653704 0.103 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
S1 C8 1.743(5) . ?
S1 C1 1.745(5) . ?
O2 C5 1.366(6) . ?
O2 C10 1.427(6) . ?
O1 C6 1.369(6) . ?
O1 C9 1.427(6) . ?
N1 H1 0.8600 . ?
N1 C12 1.414(6) . ?
N1 C1 1.352(6) . ?
C3 C8 1.393(6) . ?
C3 C2 1.435(7) . ?
C3 C4 1.407(7) . ?
C5 C4 1.372(7) . ?
C5 C6 1.420(6) . ?
C8 C7 1.388(7) . ?
C2 C1 1.394(6) . ?
C2 C11 1.420(7) . ?
C4 H4 0.9300 . ?
C12 C17 1.388(7) . ?
C12 C13 1.385(7) . ?
C6 C7 1.378(7) . ?
C7 H7 0.9300 . ?
N2 C11 1.141(6) . ?
C17 H17 0.9300 . ?
C17 C16 1.378(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(8) . ?
C16 H16 0.9300 . ?
C16 C15 1.375(8) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C14 1.382(8) . ?
C14 H14 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
C8 S1 C1 92.0(2) . . ?
C5 O2 C10 117.2(4) . . ?
C6 O1 C9 116.9(4) . . ?
C12 N1 H1 116.2 . . ?
C1 N1 H1 116.2 . . ?
C1 N1 C12 127.5(4) . . ?
C8 C3 C2 112.0(4) . . ?
C8 C3 C4 118.9(4) . . ?
C4 C3 C2 129.1(4) . . ?
O2 C5 C4 124.7(4) . . ?
O2 C5 C6 114.8(4) . . ?
C4 C5 C6 120.5(4) . . ?
C3 C8 S1 111.8(4) . . ?
C7 C8 S1 126.2(3) . . ?
C7 C8 C3 122.0(4) . . ?
C1 C2 C3 113.4(4) . . ?
C1 C2 C11 121.8(5) . . ?
C11 C2 C3 124.8(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.7(4) . . ?
C5 C4 H4 120.2 . . ?
C17 C12 N1 122.9(5) . . ?
C13 C12 N1 117.5(4) . . ?
C13 C12 C17 119.5(5) . . ?
O1 C6 C5 114.9(4) . . ?
O1 C6 C7 124.9(4) . . ?
C7 C6 C5 120.1(4) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 C8 118.8(4) . . ?
C6 C7 H7 120.6 . . ?
N1 C1 S1 122.6(4) . . ?
N1 C1 C2 126.5(4) . . ?
C2 C1 S1 110.9(4) . . ?
C12 C17 H17 120.1 . . ?
C16 C17 C12 119.7(5) . . ?
C16 C17 H17 120.1 . . ?
N2 C11 C2 179.3(6) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.8(5) . . ?
C14 C13 H13 120.1 . . ?
C17 C16 H16 119.5 . . ?
C15 C16 C17 121.1(5) . . ?
C15 C16 H16 119.5 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C15 H15 120.5 . . ?
C16 C15 C14 119.0(5) . . ?
C14 C15 H15 120.5 . . ?
C13 C14 C15 120.8(6) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_shelx_SHELXL_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.741
_oxdiff_exptl_absorpt_empirical_full_min 0.142
####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 1855419'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-22 downloaded from the CCDC.
;
_audit_creation_date             2018-07-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_formula_moiety         'C17 H14 N2 O2 S'
_chemical_formula_sum            'C17 H14 N2 O2 S'
_chemical_formula_weight         310.38
_chemical_oxdiff_formula         'C72 H56 N4 O8 S4 '
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 0.01920 0.00962 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 0.33537 0.55136 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 0.05239 0.03377 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 0.03256 0.01839 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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.7047(2)
_cell_length_b                   10.3186(2)
_cell_length_c                   13.6857(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.046(3)
_cell_angle_gamma                90
_cell_volume                     1520.99(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10815
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.1720
_cell_measurement_theta_min      4.0870
_exptl_absorpt_coefficient_mu    1.963
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3553
_exptl_crystal_description       needle
_exptl_crystal_F_000             651.2294
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15328
_diffrn_reflns_theta_full        75.5125
_diffrn_reflns_theta_max         75.51
_diffrn_reflns_theta_min         4.10
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9756
_diffrn_measured_fraction_theta_max 0.9756
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -48.00   0.50    0.25    --  -38.50-162.00 -24.00  112
  2  ω   -108.00 -22.00   0.50    0.25    --  -38.50 162.00   2.00  172
  3  ω    -84.00   5.00   0.50    0.25    --  -38.50 117.00-147.00  178
  4  ω     17.00  96.00   0.50    0.25    --   49.56-117.00 125.00  158
  5  ω     44.00 119.00   0.50    0.25    --   49.56-162.00 -24.00  150
  6  ω     69.00 115.00   0.50    0.25    --   49.56 162.00   2.00   92
  7  ω     44.00 142.00   0.50    1.00    --  102.63-162.00 -24.00  196
  8  ω     98.00 170.00   0.50    1.00    --  102.63 117.00-147.00  144
  9  ω     36.00 113.00   0.50    1.00    --  102.63-117.00 125.00  154
 10  ω     69.00 162.00   0.50    1.00    --  102.63 162.00   2.00  186
 11  ω    -62.00  26.00   0.50    0.25    --  -38.50  77.00-120.00  176
 12  ω    -17.00  53.00   0.50    0.25    --   49.56 -37.00 -90.00  140
 13  ω     38.00 107.00   0.50    1.00    --  102.63 -45.00 -90.00  138
 14  ω     40.00 116.00   0.50    1.00    --  102.63 -61.00 -90.00  152
 15  ω     40.00 116.00   0.50    1.00    --  102.63 -61.00  30.00  152
 16  ω     95.00 171.00   0.50    1.00    --  102.63  15.00  30.00  152
 17  ω     80.00 167.00   0.50    1.00    --  102.63  77.00 -90.00  174
 18  ω     38.00 107.00   0.50    1.00    --  102.63 -45.00   0.00  138
 19  ω     38.00 107.00   0.50    1.00    --  102.63 -45.00  90.00  138
 20  ω    109.00 160.00   0.50    1.00    --  102.63  45.00-150.00  102
 21  ω     99.00 167.00   0.50    1.00    --  102.63  45.00 120.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0586336000
_diffrn_orient_matrix_UB_12      0.0299292000
_diffrn_orient_matrix_UB_13      0.1197947000
_diffrn_orient_matrix_UB_21      -0.0844976000
_diffrn_orient_matrix_UB_22      0.1197429000
_diffrn_orient_matrix_UB_23      -0.0180078000
_diffrn_orient_matrix_UB_31      -0.0993503000
_diffrn_orient_matrix_UB_32      -0.0840419000
_diffrn_orient_matrix_UB_33      0.0170920000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -14
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                2834
_reflns_number_total             3077
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.2363
_refine_diff_density_min         -0.4255
_refine_diff_density_rms         0.0986
_refine_ls_d_res_high            0.7962
_refine_ls_d_res_low             10.7706
_refine_ls_goodness_of_fit_ref   1.0565
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3077
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.0565
_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)+(0.0758P)²+0.3490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1241
_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:
 N1(H10), C6(H6), C7(H7), C10(H12), C14(H16), C11(H13), C12(H14), C13(H15)
2.b Idealised Me refined as rotating group:
 C17(H20a,H20b,H20c), C16(H18a,H18b,H18c)
;
_atom_sites_solution_primary     dual
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
S9 S 0.27951(4) 0.37879(4) 0.30511(3) 0.04371(16) Uani 1.000000 .
O17 O 0.41107(11) 0.33785(12) 0.69830(9) 0.0453(3) Uani 1.000000 .
O19 O 0.64656(11) 0.27276(13) 0.73401(10) 0.0504(3) Uani 1.000000 .
N10 N 0.06175(12) 0.45975(15) 0.31351(11) 0.0452(3) Uani 1.000000 .
H10 H 0.02654(12) 0.49560(15) 0.35122(11) 0.0542(4) Uiso 1.000000 R
C4 C 0.44913(14) 0.33401(15) 0.61483(12) 0.0372(3) Uani 1.000000 .
N22 N 0.11315(15) 0.43946(18) 0.59273(13) 0.0577(4) Uani 1.000000 .
C3 C 0.36439(14) 0.36033(14) 0.51248(12) 0.0349(3) Uani 1.000000 .
C1 C 0.17945(14) 0.41541(15) 0.36780(12) 0.0372(3) Uani 1.000000 .
C5 C 0.56997(14) 0.29681(15) 0.63096(13) 0.0395(3) Uani 1.000000 .
C11 C -0.00928(14) 0.45431(15) 0.20380(13) 0.0391(3) Uani 1.000000 .
C2 C 0.23591(14) 0.39989(14) 0.47639(13) 0.0356(3) Uani 1.000000 .
C8 C 0.40108(14) 0.34592(15) 0.42687(12) 0.0377(3) Uani 1.000000 .
C6 C 0.60458(15) 0.28512(17) 0.54425(14) 0.0444(4) Uani 1.000000 .
H6 H 0.68553(15) 0.26148(17) 0.55578(14) 0.0533(4) Uiso 1.000000 R
C7 C 0.52069(15) 0.30806(17) 0.44222(14) 0.0440(4) Uani 1.000000 .
H7 H 0.54368(15) 0.29838(17) 0.38482(14) 0.0528(4) Uiso 1.000000 R
C21 C 0.17045(14) 0.42100(16) 0.54320(13) 0.0403(3) Uani 1.000000 .
C12 C 0.00316(17) 0.35605(18) 0.13941(15) 0.0485(4) Uani 1.000000 .
H12 H 0.06343(17) 0.29250(18) 0.16804(15) 0.0582(5) Uiso 1.000000 R
C16 C -0.10101(18) 0.54738(18) 0.15907(16) 0.0535(4) Uani 1.000000 .
H16 H -0.11033(18) 0.61430(18) 0.20087(16) 0.0642(5) Uiso 1.000000 R
C13 C -0.07368(19) 0.3524(2) 0.03300(16) 0.0598(5) Uani 1.000000 .
H13 H -0.06376(19) 0.2869(2) -0.00968(16) 0.0718(6) Uiso 1.000000 R
C20 C 0.76932(17) 0.2312(2) 0.75333(18) 0.0603(5) Uani 1.000000 .
H20a H 0.76608(17) 0.1567(10) 0.7102(10) 0.0904(8) Uiso 1.000000 GR
H20b H 0.8134(5) 0.2998(6) 0.7359(13) 0.0904(8) Uiso 1.000000 GR
H20c H 0.8114(5) 0.2088(16) 0.8269(3) 0.0904(8) Uiso 1.000000 GR
C14 C -0.16494(19) 0.4444(2) -0.01094(16) 0.0611(5) Uani 1.000000 .
H14 H -0.21660(19) 0.4413(2) -0.08264(16) 0.0733(6) Uiso 1.000000 R
C15 C -0.17821(19) 0.5408(2) 0.05292(17) 0.0631(5) Uani 1.000000 .
H15 H -0.24022(19) 0.6026(2) 0.02420(17) 0.0758(6) Uiso 1.000000 R
C18 C 0.4464(2) 0.4514(2) 0.76198(17) 0.0622(5) Uani 1.000000 .
H18a H 0.4094(13) 0.5259(3) 0.7193(4) 0.0934(8) Uiso 1.000000 GR
H18b H 0.4185(15) 0.4451(8) 0.8191(8) 0.0934(8) Uiso 1.000000 GR
H18c H 0.5352(2) 0.4599(9) 0.7905(11) 0.0934(8) Uiso 1.000000 GR


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
S9 C1 1.7427(15) . ?
S9 C8 1.7493(16) . ?
O17 C4 1.3797(18) . ?
O17 C18 1.422(2) . ?
O19 C5 1.365(2) . ?
O19 C20 1.422(2) . ?
N10 H10 0.8600 . ?
N10 C1 1.363(2) . ?
N10 C11 1.404(2) . ?
C4 C3 1.390(2) . ?
C4 C5 1.397(2) . ?
N22 C21 1.141(2) . ?
C3 C2 1.446(2) . ?
C3 C8 1.405(2) . ?
C1 C2 1.379(2) . ?
C5 C6 1.401(2) . ?
C11 C12 1.388(2) . ?
C11 C16 1.391(2) . ?
C2 C21 1.421(2) . ?
C8 C7 1.388(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.377(3) . ?
C7 H7 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.380(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.380(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(3) . ?
C20 H20a 0.9600 . ?
C20 H20b 0.9600 . ?
C20 H20c 0.9600 . ?
C14 H14 0.9300 . ?
C14 C15 1.372(3) . ?
C15 H15 0.9300 . ?
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
C8 S9 C1 91.48(7) . . ?
C18 O17 C4 114.86(13) . . ?
C20 O19 C5 117.00(14) . . ?
C1 N10 H10 115.90(8) . . ?
C11 N10 H10 115.90(8) . . ?
C11 N10 C1 128.20(13) . . ?
C3 C4 O17 119.64(13) . . ?
C5 C4 O17 120.81(14) . . ?
C5 C4 C3 119.46(14) . . ?
C2 C3 C4 129.49(13) . . ?
C8 C3 C4 119.30(13) . . ?
C8 C3 C2 111.20(14) . . ?
N10 C1 S9 122.35(12) . . ?
C2 C1 S9 111.99(11) . . ?
C2 C1 N10 125.59(13) . . ?
C4 C5 O19 115.32(14) . . ?
C6 C5 O19 124.65(14) . . ?
C6 C5 C4 120.02(15) . . ?
C12 C11 N10 122.88(15) . . ?
C16 C11 N10 118.35(15) . . ?
C16 C11 C12 118.66(16) . . ?
C1 C2 C3 113.35(13) . . ?
C21 C2 C3 125.04(14) . . ?
C21 C2 C1 121.61(14) . . ?
C3 C8 S9 111.95(11) . . ?
C7 C8 S9 126.50(12) . . ?
C7 C8 C3 121.54(15) . . ?
H6 C6 C5 119.46(10) . . ?
C7 C6 C5 121.07(14) . . ?
C7 C6 H6 119.46(9) . . ?
C6 C7 C8 118.58(15) . . ?
H7 C7 C8 120.71(10) . . ?
H7 C7 C6 120.71(9) . . ?
C2 C21 N22 176.80(18) . . ?
H12 C12 C11 119.90(10) . . ?
C13 C12 C11 120.19(17) . . ?
C13 C12 H12 119.90(11) . . ?
H16 C16 C11 119.88(10) . . ?
C15 C16 C11 120.25(17) . . ?
C15 C16 H16 119.88(11) . . ?
H13 C13 C12 119.51(11) . . ?
C14 C13 C12 120.98(19) . . ?
C14 C13 H13 119.51(12) . . ?
H20a C20 O19 109.5 . . ?
H20b C20 O19 109.5 . . ?
H20b C20 H20a 109.5 . . ?
H20c C20 O19 109.5 . . ?
H20c C20 H20a 109.5 . . ?
H20c C20 H20b 109.5 . . ?
H14 C14 C13 120.57(12) . . ?
C15 C14 C13 118.86(18) . . ?
C15 C14 H14 120.57(11) . . ?
C14 C15 C16 121.05(18) . . ?
H15 C15 C16 119.48(11) . . ?
H15 C15 C14 119.48(11) . . ?
H18a C18 O17 109.5 . . ?
H18b C18 O17 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 O17 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.461
_oxdiff_exptl_absorpt_empirical_full_min 0.474
