# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_161230_pzx_3_8436
_database_code_depnum_ccdc_archive 'CCDC 1813982'
_audit_update_record             
;
2017-12-29 deposited with the CCDC.
2018-07-02 downloaded from the CCDC.
;
_audit_creation_date             2016-12-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H19 N3 O S'
_chemical_formula_sum            'C17 H19 N3 O S'
_chemical_formula_weight         313.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 S1'
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'

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

_cell_length_a                   8.4386(8)
_cell_length_b                   9.4891(9)
_cell_length_c                   11.2415(11)
_cell_angle_alpha                106.972(9)
_cell_angle_beta                 102.465(8)
_cell_angle_gamma                107.518(8)
_cell_volume                     774.17(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1736
_cell_measurement_temperature    170.0
_cell_measurement_theta_max      29.1978
_cell_measurement_theta_min      2.8307
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.902
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4768
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.836
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -18.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.8433   77.0000 -180.0000 107

#__ type_ start__ end____ width___ exp.time_
  2 omega  -44.00   35.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.8433  -77.0000   60.0000 79

#__ type_ start__ end____ width___ exp.time_
  3 omega  -48.00   38.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -12.5621   83.0000  -67.0000 86
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0246197000
_diffrn_orient_matrix_UB_12      0.0823066000
_diffrn_orient_matrix_UB_13      0.0374863000
_diffrn_orient_matrix_UB_21      0.0326814000
_diffrn_orient_matrix_UB_22      0.0200988000
_diffrn_orient_matrix_UB_23      -0.0484642000
_diffrn_orient_matrix_UB_31      -0.0840461000
_diffrn_orient_matrix_UB_32      -0.0048645000
_diffrn_orient_matrix_UB_33      -0.0337750000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2158
_reflns_number_total             2825
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2825
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0554P)²+0.0569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1282
_refine_special_details          ?
_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 Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C3(H3A), C4(H4), C8(H8), C9(H9), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.40431(8) 1.03011(8) 0.68554(6) 0.0401(2) Uani 1 1 d . . . . .
O1 O -0.1011(2) 0.1146(2) 0.58494(17) 0.0416(5) Uani 1 1 d . . . . .
N1 N 0.3296(2) 0.8573(2) 0.69404(19) 0.0337(5) Uani 1 1 d . . . . .
N2 N 0.5871(2) 1.1174(2) 0.8072(2) 0.0345(5) Uani 1 1 d . . . . .
N3 N 0.8795(2) 1.1842(2) 1.02522(19) 0.0326(5) Uani 1 1 d . . . . .
H3 H 0.889148 1.248560 0.982108 0.039 Uiso 1 1 calc R . . . .
C1 C 0.4502(3) 0.8599(3) 0.7969(2) 0.0276(5) Uani 1 1 d . . . . .
C2 C 0.4390(3) 0.7322(3) 0.8436(2) 0.0270(5) Uani 1 1 d . . . . .
C3 C 0.5794(3) 0.7697(3) 0.9517(2) 0.0288(5) Uani 1 1 d . . . . .
H3A H 0.578533 0.689583 0.986512 0.035 Uiso 1 1 calc R . . . .
C4 C 0.7250(3) 0.9176(3) 1.0155(2) 0.0313(5) Uani 1 1 d . . . . .
H4 H 0.815296 0.932759 1.090834 0.038 Uiso 1 1 calc R . . . .
C5 C 0.7398(3) 1.0401(3) 0.9720(2) 0.0275(5) Uani 1 1 d . . . . .
C6 C 0.5971(3) 1.0094(3) 0.8604(2) 0.0279(5) Uani 1 1 d . . . . .
C7 C 0.2927(3) 0.5737(3) 0.7800(2) 0.0274(5) Uani 1 1 d . . . . .
C8 C 0.1964(3) 0.5098(3) 0.6453(2) 0.0330(6) Uani 1 1 d . . . . .
H8 H 0.221127 0.572783 0.594425 0.040 Uiso 1 1 calc R . . . .
C9 C 0.0671(3) 0.3586(3) 0.5849(2) 0.0343(6) Uani 1 1 d . . . . .
H9 H 0.003368 0.318731 0.493387 0.041 Uiso 1 1 calc R . . . .
C10 C 0.0286(3) 0.2636(3) 0.6557(2) 0.0311(5) Uani 1 1 d . . . . .
C11 C 0.1190(3) 0.3238(3) 0.7896(2) 0.0323(6) Uani 1 1 d . . . . .
H11 H 0.092691 0.260569 0.839991 0.039 Uiso 1 1 calc R . . . .
C12 C 0.2480(3) 0.4773(3) 0.8495(2) 0.0304(5) Uani 1 1 d . . . . .
H12 H 0.308238 0.518137 0.941689 0.036 Uiso 1 1 calc R . . . .
C13 C -0.1200(3) 0.0008(3) 0.6447(3) 0.0417(6) Uani 1 1 d . . . . .
H13A H -0.214049 -0.101503 0.582686 0.063 Uiso 1 1 calc GR . . . .
H13B H -0.150153 0.039055 0.724308 0.063 Uiso 1 1 calc GR . . . .
H13C H -0.009027 -0.013852 0.668583 0.063 Uiso 1 1 calc GR . . . .
C14 C 1.0120(3) 1.2329(3) 1.1512(2) 0.0317(5) Uani 1 1 d . . . . .
H14A H 1.071724 1.157141 1.144935 0.038 Uiso 1 1 calc R . . . .
H14B H 0.954217 1.228721 1.218692 0.038 Uiso 1 1 calc R . . . .
C15 C 1.1471(3) 1.3997(3) 1.1937(2) 0.0323(6) Uani 1 1 d . . . . .
H15A H 1.088350 1.476258 1.204630 0.039 Uiso 1 1 calc R . . . .
H15B H 1.200544 1.405425 1.124166 0.039 Uiso 1 1 calc R . . . .
C16 C 1.2908(3) 1.4472(3) 1.3221(2) 0.0358(6) Uani 1 1 d . . . . .
H16A H 1.235798 1.432238 1.389327 0.043 Uiso 1 1 calc R . . . .
H16B H 1.354901 1.375155 1.308794 0.043 Uiso 1 1 calc R . . . .
C17 C 1.4209(3) 1.6180(3) 1.3736(3) 0.0500(7) Uani 1 1 d . . . . .
H17A H 1.476942 1.633543 1.308021 0.075 Uiso 1 1 calc GR . . . .
H17B H 1.511147 1.640963 1.455816 0.075 Uiso 1 1 calc GR . . . .
H17C H 1.359216 1.690341 1.390308 0.075 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 N1 1.609(2) . ?
S1 N2 1.611(2) . ?
O1 C10 1.366(3) . ?
O1 C13 1.418(3) . ?
N1 C1 1.354(3) . ?
N2 C6 1.343(3) . ?
N3 H3 0.8800 . ?
N3 C5 1.365(3) . ?
N3 C14 1.447(3) . ?
C1 C2 1.441(3) . ?
C1 C6 1.424(3) . ?
C2 C3 1.372(3) . ?
C2 C7 1.473(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.409(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.371(3) . ?
C5 C6 1.426(3) . ?
C7 C8 1.400(3) . ?
C7 C12 1.388(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.371(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.381(3) . ?
C10 C11 1.384(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(3) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.507(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.514(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.508(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
N1 S1 N2 101.03(10) . . ?
C10 O1 C13 117.7(2) . . ?
C1 N1 S1 106.64(16) . . ?
C6 N2 S1 105.95(17) . . ?
C5 N3 H3 119.4 . . ?
C5 N3 C14 121.18(19) . . ?
C14 N3 H3 119.4 . . ?
N1 C1 C2 126.7(2) . . ?
N1 C1 C6 112.2(2) . . ?
C6 C1 C2 121.1(2) . . ?
C1 C2 C7 123.6(2) . . ?
C3 C2 C1 114.0(2) . . ?
C3 C2 C7 122.4(2) . . ?
C2 C3 H3A 117.4 . . ?
C2 C3 C4 125.3(2) . . ?
C4 C3 H3A 117.4 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.8(2) . . ?
C5 C4 H4 119.1 . . ?
N3 C5 C4 125.3(2) . . ?
N3 C5 C6 119.0(2) . . ?
C4 C5 C6 115.7(2) . . ?
N2 C6 C1 114.2(2) . . ?
N2 C6 C5 123.7(2) . . ?
C1 C6 C5 122.1(2) . . ?
C8 C7 C2 121.7(2) . . ?
C12 C7 C2 121.8(2) . . ?
C12 C7 C8 116.5(2) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.5(2) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.7(2) . . ?
C10 C9 H9 119.6 . . ?
O1 C10 C9 115.5(2) . . ?
O1 C10 C11 125.1(2) . . ?
C9 C10 C11 119.3(2) . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.3(2) . . ?
C12 C11 H11 120.3 . . ?
C7 C12 H12 118.7 . . ?
C11 C12 C7 122.6(2) . . ?
C11 C12 H12 118.7 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 H14A 109.3 . . ?
N3 C14 H14B 109.3 . . ?
N3 C14 C15 111.80(19) . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C14 C15 C16 111.7(2) . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 C15 113.3(2) . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_shelx_SHELXL_version_number     2016/6
_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_170323_pzx_3_8434_44c10h10n2o8
_database_code_depnum_ccdc_archive 'CCDC 1813991'
_audit_update_record             
;
2017-12-29 deposited with the CCDC.
2018-07-02 downloaded from the CCDC.
;
_audit_creation_date             2017-03-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H23 N3 O3 S'
_chemical_formula_sum            'C27 H23 N3 O3 S'
_chemical_formula_weight         469.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o7 s1'
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'

_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                   13.9070(12)
_cell_length_b                   5.0220(6)
_cell_length_c                   33.693(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.091(8)
_cell_angle_gamma                90
_cell_volume                     2349.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2419
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3031
_cell_measurement_theta_min      3.2857
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.931
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            8706
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         3.292
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 5.1796
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -72.00   21.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -77.0000    0.0000 93

#__ type_ start__ end____ width___ exp.time_
  2 omega  -90.00   -3.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -77.0000  -90.0000 87
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0409511000
_diffrn_orient_matrix_UB_12      0.0618614000
_diffrn_orient_matrix_UB_13      -0.0076280000
_diffrn_orient_matrix_UB_21      0.0192021000
_diffrn_orient_matrix_UB_22      0.0221439000
_diffrn_orient_matrix_UB_23      0.0196573000
_diffrn_orient_matrix_UB_31      0.0237499000
_diffrn_orient_matrix_UB_32      -0.1249573000
_diffrn_orient_matrix_UB_33      -0.0002968000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2761
_reflns_number_total             4233
_reflns_odcompleteness_completeness 98.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         4233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0595
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0683P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1571
_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. Others
 Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=1-
 FVAR(1)
 Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=FVAR(1)
 Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=1-FVAR(2)
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(2)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C15(H15), C16(H16), C18(H18), C19(H19), C22(H22), C23(H23),
 C25(H25), C26(H26), C8(H8), C9(H9), C11(H11), C12(H12), C8A(H8A), C9A(H9A),
 C11A(H11A), C12A(H12A)
3.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C27(H27A,H27B,H27C), C13(H13A,H13B,H13C), C13A(H13D,H13E,
 H13F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.45422(6) 1.03408(17) 0.05235(2) 0.0643(3) Uani 1 1 d . . . . .
O1 O 0.89113(17) 0.3480(5) -0.05607(6) 0.0735(7) Uani 1 1 d . . . . .
O2 O 0.09161(16) 0.5610(5) 0.16830(8) 0.0891(8) Uani 1 1 d . . . . .
O3 O 0.68044(14) 0.5748(4) 0.32477(5) 0.0575(5) Uani 1 1 d . . . . .
N1 N 0.54292(16) 0.8584(4) 0.03862(6) 0.0498(6) Uani 1 1 d . . . . .
N2 N 0.44902(17) 0.9433(5) 0.09796(6) 0.0542(6) Uani 1 1 d . . . . .
N11 N 0.49066(16) 0.6904(4) 0.17533(6) 0.0451(5) Uani 1 1 d . . . . .
C1 C 0.57461(18) 0.7156(5) 0.07052(7) 0.0393(6) Uani 1 1 d . . . . .
C2 C 0.65522(18) 0.5377(5) 0.07220(7) 0.0389(6) Uani 1 1 d . . . . .
C3 C 0.67285(19) 0.4195(5) 0.10839(7) 0.0463(7) Uani 1 1 d . . . . .
H3 H 0.724084 0.300630 0.110992 0.056 Uiso 1 1 calc R . . . .
C4 C 0.6191(2) 0.4643(5) 0.14208(8) 0.0472(7) Uani 1 1 d . . . . .
H4 H 0.636483 0.374076 0.165489 0.057 Uiso 1 1 calc R . . . .
C5 C 0.54313(18) 0.6340(5) 0.14168(7) 0.0418(6) Uani 1 1 d . . . . .
C6 C 0.52010(19) 0.7643(5) 0.10473(7) 0.0409(6) Uani 1 1 d . . . . .
C7 C 0.71560(18) 0.4892(5) 0.03820(7) 0.0400(6) Uani 1 1 d . . . . .
C10 C 0.8351(2) 0.3876(6) -0.02438(8) 0.0518(7) Uani 1 1 d . . . . .
C14 C 0.38849(19) 0.6543(5) 0.17238(7) 0.0427(6) Uani 1 1 d . . . . .
C15 C 0.3302(2) 0.8043(6) 0.19581(9) 0.0614(8) Uani 1 1 d . . . . .
H15 H 0.357518 0.932793 0.212797 0.074 Uiso 1 1 calc R . . . .
C16 C 0.2322(2) 0.7649(6) 0.19417(10) 0.0700(9) Uani 1 1 d . . . . .
H16 H 0.194116 0.864174 0.210528 0.084 Uiso 1 1 calc R . . . .
C17 C 0.1903(2) 0.5817(6) 0.16879(9) 0.0591(8) Uani 1 1 d . . . . .
C18 C 0.2474(2) 0.4299(6) 0.14565(9) 0.0621(8) Uani 1 1 d . . . . .
H18 H 0.219949 0.303223 0.128402 0.075 Uiso 1 1 calc R . . . .
C19 C 0.3458(2) 0.4666(6) 0.14818(8) 0.0554(8) Uani 1 1 d . . . . .
H19 H 0.384160 0.360044 0.132907 0.066 Uiso 1 1 calc R . . . .
C20 C 0.0481(2) 0.3489(8) 0.14705(12) 0.0871(12) Uani 1 1 d . . . . .
H20A H 0.055772 0.373624 0.119151 0.131 Uiso 1 1 calc GR . . . .
H20B H -0.019287 0.343222 0.151938 0.131 Uiso 1 1 calc GR . . . .
H20C H 0.077872 0.184564 0.155529 0.131 Uiso 1 1 calc GR . . . .
C21 C 0.5386(2) 0.6528(5) 0.21379(7) 0.0431(6) Uani 1 1 d . . . . .
C22 C 0.6172(2) 0.8093(5) 0.22547(8) 0.0479(7) Uani 1 1 d . . . . .
H22 H 0.639212 0.937655 0.208260 0.057 Uiso 1 1 calc R . . . .
C23 C 0.6629(2) 0.7759(5) 0.26233(8) 0.0484(7) Uani 1 1 d . . . . .
H23 H 0.715619 0.881587 0.269872 0.058 Uiso 1 1 calc R . . . .
C24 C 0.63092(19) 0.5863(5) 0.28825(7) 0.0442(6) Uani 1 1 d . . . . .
C25 C 0.5533(2) 0.4301(6) 0.27688(8) 0.0531(7) Uani 1 1 d . . . . .
H25 H 0.531140 0.302795 0.294223 0.064 Uiso 1 1 calc R . . . .
C26 C 0.5082(2) 0.4619(5) 0.23967(8) 0.0524(7) Uani 1 1 d . . . . .
H26 H 0.456542 0.352734 0.231953 0.063 Uiso 1 1 calc R . . . .
C27 C 0.6581(3) 0.3592(6) 0.34965(9) 0.0698(9) Uani 1 1 d . . . . .
H27A H 0.669467 0.194458 0.336218 0.105 Uiso 1 1 calc GR . . . .
H27B H 0.591696 0.369355 0.355884 0.105 Uiso 1 1 calc GR . . . .
H27C H 0.698135 0.367317 0.373753 0.105 Uiso 1 1 calc GR . . . .
C8 C 0.6800(4) 0.4611(9) -0.00004(14) 0.0408(13) Uani 0.496(3) 1 d . . P A 1
H8 H 0.613951 0.475774 -0.005630 0.049 Uiso 0.496(3) 1 calc R . P A 1
C9 C 0.7397(4) 0.4111(11) -0.03083(15) 0.0467(15) Uani 0.496(3) 1 d . . P A 1
H9 H 0.712880 0.393435 -0.056573 0.056 Uiso 0.496(3) 1 calc R . P A 1
C11 C 0.8773(4) 0.4156(11) 0.01526(16) 0.0495(15) Uani 0.496(3) 1 d . . P A 1
H11 H 0.943428 0.400079 0.020365 0.059 Uiso 0.496(3) 1 calc R . P A 1
C12 C 0.8162(4) 0.4669(10) 0.04595(15) 0.0456(14) Uani 0.496(3) 1 d . . P A 1
H12 H 0.842024 0.486611 0.071817 0.055 Uiso 0.496(3) 1 calc R . P A 1
C13 C 0.9921(6) 0.294(2) -0.0488(2) 0.094(4) Uani 0.482(10) 1 d . . P B 1
H13A H 1.024410 0.453510 -0.039687 0.141 Uiso 0.482(10) 1 calc GR . P B 1
H13B H 1.018867 0.234686 -0.072913 0.141 Uiso 0.482(10) 1 calc GR . P B 1
H13C H 1.000439 0.158145 -0.028860 0.141 Uiso 0.482(10) 1 calc GR . P B 1
C8A C 0.7421(4) 0.6905(10) 0.01197(15) 0.0477(14) Uani 0.504(3) 1 d . . P A 2
H8A H 0.720150 0.863012 0.015839 0.057 Uiso 0.504(3) 1 calc R . P A 2
C9A C 0.7991(4) 0.6416(12) -0.01905(17) 0.0576(17) Uani 0.504(3) 1 d . . P A 2
H9A H 0.813650 0.777851 -0.036436 0.069 Uiso 0.504(3) 1 calc R . P A 2
C11A C 0.8039(4) 0.1815(11) -0.00192(17) 0.0571(17) Uani 0.504(3) 1 d . . P A 2
H11A H 0.820811 0.006931 -0.007554 0.069 Uiso 0.504(3) 1 calc R . P A 2
C12A C 0.7468(4) 0.2377(10) 0.02932(16) 0.0508(15) Uani 0.504(3) 1 d . . P A 2
H12A H 0.728423 0.097351 0.045237 0.061 Uiso 0.504(3) 1 calc R . P A 2
C13A C 0.9176(10) 0.1021(18) -0.0672(3) 0.132(6) Uani 0.518(10) 1 d . . P B 2
H13D H 0.948677 0.011698 -0.044936 0.197 Uiso 0.518(10) 1 calc GR . P B 2
H13E H 0.961364 0.115720 -0.088210 0.197 Uiso 0.518(10) 1 calc GR . P B 2
H13F H 0.861602 0.003633 -0.076462 0.197 Uiso 0.518(10) 1 calc GR . P B 2


_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 N1 1.605(2) . ?
S1 N2 1.608(2) . ?
O1 C10 1.370(3) . ?
O1 C13 1.438(8) . ?
O1 C13A 1.348(8) . ?
O2 C17 1.375(3) . ?
O2 C20 1.403(4) . ?
O3 C24 1.378(3) . ?
O3 C27 1.414(4) . ?
N1 C1 1.346(3) . ?
N2 C6 1.346(3) . ?
N11 C5 1.410(3) . ?
N11 C14 1.430(3) . ?
N11 C21 1.437(3) . ?
C1 C2 1.432(3) . ?
C1 C6 1.435(3) . ?
C2 C3 1.366(3) . ?
C2 C7 1.477(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.410(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.357(4) . ?
C5 C6 1.428(3) . ?
C7 C8 1.363(5) . ?
C7 C12 1.413(6) . ?
C7 C8A 1.405(6) . ?
C7 C12A 1.373(6) . ?
C10 C9 1.338(6) . ?
C10 C11 1.436(6) . ?
C10 C9A 1.386(6) . ?
C10 C11A 1.366(6) . ?
C14 C15 1.385(4) . ?
C14 C19 1.361(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.375(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.365(4) . ?
C17 C18 1.374(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(4) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.387(4) . ?
C21 C26 1.377(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.374(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.381(4) . ?
C24 C25 1.372(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.381(4) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C8 H8 0.9300 . ?
C8 C9 1.387(7) . ?
C9 H9 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.397(7) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C8A H8A 0.9300 . ?
C8A C9A 1.368(7) . ?
C9A H9A 0.9300 . ?
C11A H11A 0.9300 . ?
C11A C12A 1.382(7) . ?
C12A H12A 0.9300 . ?
C13A H13D 0.9600 . ?
C13A H13E 0.9600 . ?
C13A H13F 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
N1 S1 N2 101.21(11) . . ?
C10 O1 C13 119.0(4) . . ?
C13A O1 C10 121.7(4) . . ?
C17 O2 C20 117.8(3) . . ?
C24 O3 C27 116.5(2) . . ?
C1 N1 S1 106.64(17) . . ?
C6 N2 S1 106.31(17) . . ?
C5 N11 C14 118.3(2) . . ?
C5 N11 C21 117.6(2) . . ?
C14 N11 C21 117.2(2) . . ?
N1 C1 C2 125.9(2) . . ?
N1 C1 C6 112.7(2) . . ?
C2 C1 C6 121.4(2) . . ?
C1 C2 C7 123.3(2) . . ?
C3 C2 C1 114.1(2) . . ?
C3 C2 C7 122.6(2) . . ?
C2 C3 H3 117.6 . . ?
C2 C3 C4 124.9(2) . . ?
C4 C3 H3 117.6 . . ?
C3 C4 H4 118.7 . . ?
C5 C4 C3 122.6(2) . . ?
C5 C4 H4 118.7 . . ?
N11 C5 C6 120.5(2) . . ?
C4 C5 N11 123.7(2) . . ?
C4 C5 C6 115.8(2) . . ?
N2 C6 C1 113.1(2) . . ?
N2 C6 C5 125.6(2) . . ?
C5 C6 C1 121.3(2) . . ?
C8 C7 C2 123.9(3) . . ?
C8 C7 C12 118.2(4) . . ?
C12 C7 C2 117.9(3) . . ?
C8A C7 C2 123.3(3) . . ?
C12A C7 C2 121.3(3) . . ?
C12A C7 C8A 115.3(4) . . ?
O1 C10 C11 121.2(3) . . ?
O1 C10 C9A 117.3(3) . . ?
C9 C10 O1 119.1(3) . . ?
C9 C10 C11 119.6(4) . . ?
C11A C10 O1 122.2(3) . . ?
C11A C10 C9A 119.9(4) . . ?
C15 C14 N11 120.1(2) . . ?
C19 C14 N11 121.9(2) . . ?
C19 C14 C15 117.9(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.7(3) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 O2 116.8(3) . . ?
C16 C17 C18 119.2(3) . . ?
C18 C17 O2 124.0(3) . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.6(3) . . ?
C19 C18 H18 120.2 . . ?
C14 C19 C18 121.9(3) . . ?
C14 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 N11 120.1(2) . . ?
C26 C21 N11 121.3(2) . . ?
C26 C21 C22 118.6(2) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.4(2) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.5(3) . . ?
C24 C23 H23 119.8 . . ?
O3 C24 C23 115.5(2) . . ?
C25 C24 O3 124.9(2) . . ?
C25 C24 C23 119.5(3) . . ?
C24 C25 H25 120.0 . . ?
C24 C25 C26 120.0(3) . . ?
C26 C25 H25 120.0 . . ?
C21 C26 C25 121.1(3) . . ?
C21 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
O3 C27 H27A 109.5 . . ?
O3 C27 H27B 109.5 . . ?
O3 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C7 C8 H8 119.2 . . ?
C7 C8 C9 121.6(5) . . ?
C9 C8 H8 119.2 . . ?
C10 C9 C8 121.6(4) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C10 C11 H11 120.9 . . ?
C12 C11 C10 118.2(5) . . ?
C12 C11 H11 120.9 . . ?
C7 C12 H12 119.6 . . ?
C11 C12 C7 120.9(4) . . ?
C11 C12 H12 119.6 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C8A H8A 118.9 . . ?
C9A C8A C7 122.3(5) . . ?
C9A C8A H8A 118.9 . . ?
C10 C9A H9A 120.2 . . ?
C8A C9A C10 119.5(5) . . ?
C8A C9A H9A 120.2 . . ?
C10 C11A H11A 120.7 . . ?
C10 C11A C12A 118.7(5) . . ?
C12A C11A H11A 120.7 . . ?
C7 C12A C11A 123.7(5) . . ?
C7 C12A H12A 118.1 . . ?
C11A C12A H12A 118.1 . . ?
O1 C13A H13D 109.5 . . ?
O1 C13A H13E 109.5 . . ?
O1 C13A H13F 109.5 . . ?
H13D C13A H13E 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?

_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_170614_pzx_3_8430_2nd
_database_code_depnum_ccdc_archive 'CCDC 1813987'
_audit_update_record             
;
2017-12-29 deposited with the CCDC.
2018-07-02 downloaded from the CCDC.
;
_audit_creation_date             2017-06-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 N3 O S'
_chemical_formula_sum            'C19 H15 N3 O S'
_chemical_formula_weight         333.40
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 s1'
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'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   14.3135(14)
_cell_length_b                   14.6015(13)
_cell_length_c                   15.5923(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.462(7)
_cell_angle_gamma                90
_cell_volume                     3193.8(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3181
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3158
_cell_measurement_theta_min      3.0861
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.914
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0696
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14264
_diffrn_reflns_point_group_measured_fraction_full 0.774
_diffrn_reflns_point_group_measured_fraction_max 0.773
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         3.092
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -62.00   31.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808  -38.0000   30.0000 93

#__ type_ start__ end____ width___ exp.time_
  2 omega  -15.00   89.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000 -180.0000 104
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0068413000
_diffrn_orient_matrix_UB_12      -0.0457980000
_diffrn_orient_matrix_UB_13      -0.0126374000
_diffrn_orient_matrix_UB_21      0.0421272000
_diffrn_orient_matrix_UB_22      0.0133111000
_diffrn_orient_matrix_UB_23      -0.0141561000
_diffrn_orient_matrix_UB_31      0.0271107000
_diffrn_orient_matrix_UB_32      -0.0092101000
_diffrn_orient_matrix_UB_33      0.0423610000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.489
_reflns_Friedel_fraction_full    0.533
_reflns_Friedel_fraction_max     0.530
_reflns_number_gt                6475
_reflns_number_total             9031
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 1736 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.22(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     869
_refine_ls_number_reflns         9031
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.013
_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)+(0.0502P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1347
_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:
 N3(H3), C4(H4), C5(H5), C8(H8), C9(H9A), C11(H11), C12(H12), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19), N6(H6), C23(H23), C24(H24), C27(H27),
 C28(H28), C30(H30), C31(H31), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38),
  N9(H9), C42(H42), C43(H43), C46(H46), C47(H47), C49(H49), C50(H50), C53(H53),
 C54(H54), C55(H55), C56(H56), C57(H57), N12(H12A), C61(H61), C62(H62),
 C65(H65), C66(H66), C68(H68), C69(H69), C72(H72), C73(H73), C74(H74), C75(H75),
  C76(H76)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C32(H32A,H32B,H32C), C51(H51A,H51B,H51C), C70(H70A,H70B,
 H70C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.73148(11) 0.33617(15) 0.29285(9) 0.0620(5) Uani 1 1 d . . . . .
O1 O 0.3147(3) 0.2842(3) -0.1226(2) 0.0528(12) Uani 1 1 d . . . . .
N1 N 0.6973(4) 0.3211(4) 0.3844(3) 0.0545(15) Uani 1 1 d . . . . .
N2 N 0.6327(3) 0.3181(4) 0.2245(3) 0.0453(13) Uani 1 1 d . . . . .
N3 N 0.5912(4) 0.2806(4) 0.5130(3) 0.0509(15) Uani 1 1 d . . . . .
H3 H 0.652474 0.279899 0.522985 0.061 Uiso 1 1 calc R . . . .
C1 C 0.6042(4) 0.3006(4) 0.3637(4) 0.0405(16) Uani 1 1 d . . . . .
C2 C 0.5664(4) 0.2979(4) 0.2721(4) 0.0376(15) Uani 1 1 d . . . . .
C3 C 0.4681(4) 0.2780(4) 0.2395(3) 0.0343(14) Uani 1 1 d . . . . .
C4 C 0.4160(4) 0.2595(5) 0.3024(4) 0.0442(16) Uani 1 1 d . . . . .
H4 H 0.351871 0.245219 0.283746 0.053 Uiso 1 1 calc R . . . .
C5 C 0.4527(5) 0.2604(4) 0.3929(4) 0.0444(16) Uani 1 1 d . . . . .
H5 H 0.412452 0.246897 0.431298 0.053 Uiso 1 1 calc R . . . .
C6 C 0.5468(4) 0.2808(4) 0.4261(3) 0.0394(15) Uani 1 1 d . . . . .
C7 C 0.4258(4) 0.2795(4) 0.1450(3) 0.0377(14) Uani 1 1 d . . . . .
C8 C 0.4744(4) 0.2445(4) 0.0830(3) 0.0417(15) Uani 1 1 d . . . . .
H8 H 0.534490 0.218936 0.101792 0.050 Uiso 1 1 calc R . . . .
C9 C 0.4361(4) 0.2468(4) -0.0048(3) 0.0420(15) Uani 1 1 d . . . . .
H9A H 0.469896 0.222623 -0.044749 0.050 Uiso 1 1 calc R . . . .
C10 C 0.3469(4) 0.2852(4) -0.0340(4) 0.0380(14) Uani 1 1 d . . . . .
C11 C 0.2976(4) 0.3198(5) 0.0248(4) 0.0469(17) Uani 1 1 d . . . . .
H11 H 0.237713 0.345734 0.005749 0.056 Uiso 1 1 calc R . . . .
C12 C 0.3371(4) 0.3160(4) 0.1132(4) 0.0458(16) Uani 1 1 d . . . . .
H12 H 0.302224 0.339006 0.152792 0.055 Uiso 1 1 calc R . . . .
C13 C 0.2293(5) 0.3321(6) -0.1577(4) 0.067(2) Uani 1 1 d . . . . .
H13A H 0.221257 0.335026 -0.220296 0.100 Uiso 1 1 calc GR . . . .
H13B H 0.232832 0.393074 -0.134249 0.100 Uiso 1 1 calc GR . . . .
H13C H 0.176025 0.300645 -0.142431 0.100 Uiso 1 1 calc GR . . . .
C14 C 0.5495(4) 0.2814(4) 0.5880(3) 0.0421(15) Uani 1 1 d . . . . .
C15 C 0.4626(5) 0.3239(5) 0.5884(4) 0.0537(18) Uani 1 1 d . . . . .
H15 H 0.427994 0.350625 0.537758 0.064 Uiso 1 1 calc R . . . .
C16 C 0.4283(5) 0.3258(6) 0.6658(4) 0.065(2) Uani 1 1 d . . . . .
H16 H 0.370527 0.354568 0.666906 0.078 Uiso 1 1 calc R . . . .
C17 C 0.4782(6) 0.2861(6) 0.7400(5) 0.075(2) Uani 1 1 d . . . . .
H17 H 0.453410 0.286084 0.790781 0.090 Uiso 1 1 calc R . . . .
C18 C 0.5657(6) 0.2459(6) 0.7400(4) 0.073(2) Uani 1 1 d . . . . .
H18 H 0.600661 0.220439 0.791165 0.088 Uiso 1 1 calc R . . . .
C19 C 0.6009(5) 0.2436(5) 0.6637(4) 0.0558(18) Uani 1 1 d . . . . .
H19 H 0.659554 0.216368 0.663482 0.067 Uiso 1 1 calc R . . . .
S2 S 0.96272(11) 0.00895(13) 0.31711(9) 0.0500(4) Uani 1 1 d . . . . .
O2 O 0.5512(3) 0.0630(4) -0.1050(2) 0.0594(13) Uani 1 1 d . . . . .
N4 N 0.9261(4) 0.0235(4) 0.4075(3) 0.0485(13) Uani 1 1 d . . . . .
N5 N 0.8655(3) 0.0250(4) 0.2473(3) 0.0438(13) Uani 1 1 d . . . . .
N6 N 0.8140(4) 0.0608(4) 0.5330(3) 0.0560(15) Uani 1 1 d . . . . .
H6 H 0.874752 0.068518 0.543798 0.067 Uiso 1 1 calc R . . . .
C20 C 0.8323(4) 0.0431(4) 0.3849(4) 0.0399(15) Uani 1 1 d . . . . .
C21 C 0.7966(4) 0.0434(4) 0.2932(4) 0.0387(14) Uani 1 1 d . . . . .
C22 C 0.6974(4) 0.0591(4) 0.2583(4) 0.0421(15) Uani 1 1 d . . . . .
C23 C 0.6426(5) 0.0732(4) 0.3189(4) 0.0499(17) Uani 1 1 d . . . . .
H23 H 0.577674 0.082782 0.298869 0.060 Uiso 1 1 calc R . . . .
C24 C 0.6773(5) 0.0742(5) 0.4098(4) 0.0492(17) Uani 1 1 d . . . . .
H24 H 0.635007 0.085207 0.446771 0.059 Uiso 1 1 calc R . . . .
C25 C 0.7719(5) 0.0596(5) 0.4457(4) 0.0462(16) Uani 1 1 d . . . . .
C26 C 0.6589(4) 0.0562(4) 0.1629(3) 0.0416(15) Uani 1 1 d . . . . .
C27 C 0.7050(4) 0.0999(4) 0.1040(4) 0.0435(15) Uani 1 1 d . . . . .
H27 H 0.761758 0.130842 0.124980 0.052 Uiso 1 1 calc R . . . .
C28 C 0.6692(4) 0.0986(4) 0.0165(4) 0.0446(15) Uani 1 1 d . . . . .
H28 H 0.702726 0.126432 -0.021726 0.054 Uiso 1 1 calc R . . . .
C29 C 0.5823(5) 0.0557(5) -0.0162(4) 0.0453(16) Uani 1 1 d . . . . .
C30 C 0.5352(4) 0.0118(5) 0.0407(4) 0.0509(16) Uani 1 1 d . . . . .
H30 H 0.477730 -0.017745 0.019635 0.061 Uiso 1 1 calc R . . . .
C31 C 0.5734(4) 0.0118(5) 0.1290(4) 0.0477(16) Uani 1 1 d . . . . .
H31 H 0.541393 -0.018630 0.166959 0.057 Uiso 1 1 calc R . . . .
C32 C 0.4644(5) 0.0190(7) -0.1433(4) 0.080(3) Uani 1 1 d . . . . .
H32A H 0.454658 0.023632 -0.205894 0.120 Uiso 1 1 calc GR . . . .
H32B H 0.412408 0.047918 -0.123343 0.120 Uiso 1 1 calc GR . . . .
H32C H 0.467438 -0.044431 -0.126661 0.120 Uiso 1 1 calc GR . . . .
C33 C 0.7731(5) 0.0515(4) 0.6068(4) 0.0442(16) Uani 1 1 d . . . . .
C34 C 0.6861(5) 0.0069(5) 0.6057(4) 0.0537(17) Uani 1 1 d . . . . .
H34 H 0.650452 -0.015175 0.553375 0.064 Uiso 1 1 calc R . . . .
C35 C 0.6537(5) -0.0038(5) 0.6821(4) 0.0612(19) Uani 1 1 d . . . . .
H35 H 0.595762 -0.033055 0.681001 0.073 Uiso 1 1 calc R . . . .
C36 C 0.7050(6) 0.0275(5) 0.7599(4) 0.064(2) Uani 1 1 d . . . . .
H36 H 0.682160 0.019574 0.811206 0.076 Uiso 1 1 calc R . . . .
C37 C 0.7914(6) 0.0712(5) 0.7617(4) 0.066(2) Uani 1 1 d . . . . .
H37 H 0.827330 0.092136 0.814381 0.079 Uiso 1 1 calc R . . . .
C38 C 0.8238(5) 0.0835(5) 0.6851(4) 0.0525(17) Uani 1 1 d . . . . .
H38 H 0.881021 0.114107 0.686404 0.063 Uiso 1 1 calc R . . . .
S3 S 0.69526(11) 0.34290(13) 0.03442(10) 0.0502(4) Uani 1 1 d . . . . .
O3 O 1.1075(3) 0.2742(4) 0.4572(3) 0.0585(13) Uani 1 1 d . . . . .
N7 N 0.7332(4) 0.3362(4) -0.0557(3) 0.0476(13) Uani 1 1 d . . . . .
N8 N 0.7925(3) 0.3276(4) 0.1047(3) 0.0427(13) Uani 1 1 d . . . . .
N9 N 0.8483(4) 0.3210(4) -0.1806(3) 0.0489(14) Uani 1 1 d . . . . .
H9 H 0.788359 0.332932 -0.189495 0.059 Uiso 1 1 calc R . . . .
C39 C 0.8273(4) 0.3206(4) -0.0329(3) 0.0383(14) Uani 1 1 d . . . . .
C40 C 0.8625(4) 0.3147(4) 0.0592(4) 0.0408(15) Uani 1 1 d . . . . .
C41 C 0.9612(4) 0.2998(4) 0.0947(3) 0.0403(15) Uani 1 1 d . . . . .
C42 C 1.0170(4) 0.2900(5) 0.0338(4) 0.0522(18) Uani 1 1 d . . . . .
H42 H 1.081582 0.278472 0.053850 0.063 Uiso 1 1 calc R . . . .
C43 C 0.9836(5) 0.2962(5) -0.0583(4) 0.0542(19) Uani 1 1 d . . . . .
H43 H 1.026888 0.289703 -0.095129 0.065 Uiso 1 1 calc R . . . .
C44 C 0.8902(4) 0.3113(4) -0.0941(3) 0.0413(15) Uani 1 1 d . . . . .
C45 C 1.0007(4) 0.2959(4) 0.1891(3) 0.0387(15) Uani 1 1 d . . . . .
C46 C 0.9508(4) 0.2539(4) 0.2465(3) 0.0431(15) Uani 1 1 d . . . . .
H46 H 0.891084 0.228758 0.224751 0.052 Uiso 1 1 calc R . . . .
C47 C 0.9882(5) 0.2490(4) 0.3352(4) 0.0472(16) Uani 1 1 d . . . . .
H47 H 0.953574 0.220881 0.372427 0.057 Uiso 1 1 calc R . . . .
C48 C 1.0764(5) 0.2857(4) 0.3685(4) 0.0423(15) Uani 1 1 d . . . . .
C49 C 1.1270(4) 0.3291(4) 0.3134(4) 0.0437(15) Uani 1 1 d . . . . .
H49 H 1.185929 0.355625 0.335746 0.052 Uiso 1 1 calc R . . . .
C50 C 1.0893(4) 0.3327(5) 0.2249(4) 0.0462(16) Uani 1 1 d . . . . .
H50 H 1.124282 0.360792 0.187948 0.055 Uiso 1 1 calc R . . . .
C51 C 1.1969(5) 0.3093(6) 0.4979(4) 0.072(2) Uani 1 1 d . . . . .
H51A H 1.245888 0.281246 0.472796 0.108 Uiso 1 1 calc GR . . . .
H51B H 1.208018 0.296238 0.559433 0.108 Uiso 1 1 calc GR . . . .
H51C H 1.197832 0.374367 0.489226 0.108 Uiso 1 1 calc GR . . . .
C52 C 0.8852(4) 0.3150(4) -0.2578(4) 0.0417(15) Uani 1 1 d . . . . .
C53 C 0.9687(4) 0.2702(5) -0.2639(4) 0.0483(16) Uani 1 1 d . . . . .
H53 H 1.006091 0.243953 -0.214408 0.058 Uiso 1 1 calc R . . . .
C54 C 0.9963(5) 0.2645(5) -0.3437(4) 0.0569(18) Uani 1 1 d . . . . .
H54 H 1.052230 0.233849 -0.347695 0.068 Uiso 1 1 calc R . . . .
C55 C 0.9424(6) 0.3035(6) -0.4171(4) 0.065(2) Uani 1 1 d . . . . .
H55 H 0.961864 0.299694 -0.470421 0.078 Uiso 1 1 calc R . . . .
C56 C 0.8593(5) 0.3485(5) -0.4113(4) 0.0588(18) Uani 1 1 d . . . . .
H56 H 0.821716 0.374236 -0.460922 0.071 Uiso 1 1 calc R . . . .
C57 C 0.8322(4) 0.3550(5) -0.3318(3) 0.0463(16) Uani 1 1 d . . . . .
H57 H 0.777076 0.387102 -0.327852 0.056 Uiso 1 1 calc R . . . .
S4 S 0.92816(12) 0.02730(15) 0.05866(10) 0.0587(5) Uani 1 1 d . . . . .
O4 O 1.3440(3) 0.0734(4) 0.4804(3) 0.0619(14) Uani 1 1 d . . . . .
N10 N 0.9661(4) 0.0337(4) -0.0321(3) 0.0523(15) Uani 1 1 d . . . . .
N11 N 1.0267(3) 0.0384(4) 0.1288(3) 0.0454(13) Uani 1 1 d . . . . .
N12 N 1.0788(4) 0.0451(4) -0.1586(3) 0.0512(15) Uani 1 1 d . . . . .
H12A H 1.018344 0.035779 -0.167635 0.061 Uiso 1 1 calc R . . . .
C58 C 1.0602(4) 0.0462(4) -0.0089(4) 0.0398(15) Uani 1 1 d . . . . .
C59 C 1.0962(4) 0.0483(4) 0.0826(3) 0.0377(15) Uani 1 1 d . . . . .
C60 C 1.1963(4) 0.0612(4) 0.1169(3) 0.0381(15) Uani 1 1 d . . . . .
C61 C 1.2512(5) 0.0712(5) 0.0557(4) 0.0470(17) Uani 1 1 d . . . . .
H61 H 1.316004 0.081495 0.075290 0.056 Uiso 1 1 calc R . . . .
C62 C 1.2164(5) 0.0669(5) -0.0363(4) 0.0479(17) Uani 1 1 d . . . . .
H62 H 1.259282 0.073311 -0.073570 0.058 Uiso 1 1 calc R . . . .
C63 C 1.1223(5) 0.0536(5) -0.0717(4) 0.0430(16) Uani 1 1 d . . . . .
C64 C 1.2368(4) 0.0617(4) 0.2121(4) 0.0376(15) Uani 1 1 d . . . . .
C65 C 1.1872(5) 0.1011(4) 0.2714(4) 0.0431(16) Uani 1 1 d . . . . .
H65 H 1.127734 0.127377 0.250909 0.052 Uiso 1 1 calc R . . . .
C66 C 1.2249(5) 0.1016(5) 0.3597(4) 0.0446(16) Uani 1 1 d . . . . .
H66 H 1.189912 0.126690 0.398172 0.053 Uiso 1 1 calc R . . . .
C67 C 1.3133(5) 0.0658(5) 0.3918(4) 0.0445(16) Uani 1 1 d . . . . .
C68 C 1.3643(4) 0.0258(5) 0.3342(4) 0.0474(16) Uani 1 1 d . . . . .
H68 H 1.424223 0.000590 0.355090 0.057 Uiso 1 1 calc R . . . .
C69 C 1.3250(4) 0.0238(5) 0.2452(3) 0.0429(16) Uani 1 1 d . . . . .
H69 H 1.358906 -0.003740 0.207013 0.052 Uiso 1 1 calc R . . . .
C70 C 1.4341(5) 0.0386(6) 0.5182(4) 0.078(2) Uani 1 1 d . . . . .
H70A H 1.435683 -0.026027 0.507267 0.117 Uiso 1 1 calc GR . . . .
H70B H 1.446389 0.049286 0.580225 0.117 Uiso 1 1 calc GR . . . .
H70C H 1.481946 0.068689 0.493142 0.117 Uiso 1 1 calc GR . . . .
C71 C 1.1170(4) 0.0492(4) -0.2342(3) 0.0413(15) Uani 1 1 d . . . . .
C72 C 1.1977(5) 0.1003(5) -0.2409(4) 0.0551(18) Uani 1 1 d . . . . .
H72 H 1.230830 0.132647 -0.192944 0.066 Uiso 1 1 calc R . . . .
C73 C 1.2274(5) 0.1021(6) -0.3196(4) 0.071(2) Uani 1 1 d . . . . .
H73 H 1.282555 0.134021 -0.323610 0.085 Uiso 1 1 calc R . . . .
C74 C 1.1778(6) 0.0580(6) -0.3921(4) 0.070(2) Uani 1 1 d . . . . .
H74 H 1.197973 0.061307 -0.445192 0.084 Uiso 1 1 calc R . . . .
C75 C 1.0980(5) 0.0089(5) -0.3852(3) 0.0595(19) Uani 1 1 d . . . . .
H75 H 1.063569 -0.021000 -0.434014 0.071 Uiso 1 1 calc R . . . .
C76 C 1.0688(4) 0.0035(5) -0.3076(3) 0.0491(16) Uani 1 1 d . . . . .
H76 H 1.015573 -0.031579 -0.303714 0.059 Uiso 1 1 calc 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 N1 1.614(5) . ?
S1 N2 1.614(5) . ?
O1 C10 1.368(6) . ?
O1 C13 1.421(7) . ?
N1 C1 1.341(7) . ?
N2 C2 1.349(7) . ?
N3 H3 0.8600 . ?
N3 C6 1.377(7) . ?
N3 C14 1.415(6) . ?
C1 C2 1.424(8) . ?
C1 C6 1.423(7) . ?
C2 C3 1.427(8) . ?
C3 C4 1.372(7) . ?
C3 C7 1.477(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.406(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(8) . ?
C7 C8 1.395(7) . ?
C7 C12 1.376(8) . ?
C8 H8 0.9300 . ?
C8 C9 1.371(7) . ?
C9 H9A 0.9300 . ?
C9 C10 1.387(8) . ?
C10 C11 1.360(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(8) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.392(8) . ?
C14 C19 1.376(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.390(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.363(10) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(10) . ?
C18 H18 0.9300 . ?
C18 C19 1.382(8) . ?
C19 H19 0.9300 . ?
S2 N4 1.613(4) . ?
S2 N5 1.604(5) . ?
O2 C29 1.372(7) . ?
O2 C32 1.421(8) . ?
N4 C20 1.349(7) . ?
N5 C21 1.357(7) . ?
N6 H6 0.8600 . ?
N6 C25 1.375(7) . ?
N6 C33 1.398(7) . ?
C20 C21 1.419(8) . ?
C20 C25 1.425(7) . ?
C21 C22 1.434(8) . ?
C22 C23 1.359(7) . ?
C22 C26 1.480(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.406(8) . ?
C24 H24 0.9300 . ?
C24 C25 1.375(8) . ?
C26 C27 1.387(8) . ?
C26 C31 1.393(8) . ?
C27 H27 0.9300 . ?
C27 C28 1.359(8) . ?
C28 H28 0.9300 . ?
C28 C29 1.395(9) . ?
C29 C30 1.375(8) . ?
C30 H30 0.9300 . ?
C30 C31 1.377(7) . ?
C31 H31 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.403(9) . ?
C33 C38 1.372(8) . ?
C34 H34 0.9300 . ?
C34 C35 1.370(8) . ?
C35 H35 0.9300 . ?
C35 C36 1.365(9) . ?
C36 H36 0.9300 . ?
C36 C37 1.388(10) . ?
C37 H37 0.9300 . ?
C37 C38 1.375(8) . ?
C38 H38 0.9300 . ?
S3 N7 1.607(5) . ?
S3 N8 1.607(5) . ?
O3 C48 1.376(6) . ?
O3 C51 1.407(8) . ?
N7 C39 1.343(7) . ?
N8 C40 1.351(6) . ?
N9 H9 0.8600 . ?
N9 C44 1.370(7) . ?
N9 C52 1.410(6) . ?
C39 C40 1.428(7) . ?
C39 C44 1.442(7) . ?
C40 C41 1.427(8) . ?
C41 C42 1.366(7) . ?
C41 C45 1.469(7) . ?
C42 H42 0.9300 . ?
C42 C43 1.423(7) . ?
C43 H43 0.9300 . ?
C43 C44 1.361(8) . ?
C45 C46 1.394(8) . ?
C45 C50 1.388(8) . ?
C46 H46 0.9300 . ?
C46 C47 1.382(8) . ?
C47 H47 0.9300 . ?
C47 C48 1.375(9) . ?
C48 C49 1.384(8) . ?
C49 H49 0.9300 . ?
C49 C50 1.379(7) . ?
C50 H50 0.9300 . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C52 C53 1.381(8) . ?
C52 C57 1.379(8) . ?
C53 H53 0.9300 . ?
C53 C54 1.381(7) . ?
C54 H54 0.9300 . ?
C54 C55 1.370(9) . ?
C55 H55 0.9300 . ?
C55 C56 1.377(10) . ?
C56 H56 0.9300 . ?
C56 C57 1.373(7) . ?
C57 H57 0.9300 . ?
S4 N10 1.616(4) . ?
S4 N11 1.612(5) . ?
O4 C67 1.369(7) . ?
O4 C70 1.402(8) . ?
N10 C58 1.335(7) . ?
N11 C59 1.348(6) . ?
N12 H12A 0.8600 . ?
N12 C63 1.379(7) . ?
N12 C71 1.396(6) . ?
C58 C59 1.418(7) . ?
C58 C63 1.451(7) . ?
C59 C60 1.439(8) . ?
C60 C61 1.358(7) . ?
C60 C64 1.482(8) . ?
C61 H61 0.9300 . ?
C61 C62 1.423(8) . ?
C62 H62 0.9300 . ?
C62 C63 1.364(8) . ?
C64 C65 1.398(8) . ?
C64 C69 1.381(8) . ?
C65 H65 0.9300 . ?
C65 C66 1.375(8) . ?
C66 H66 0.9300 . ?
C66 C67 1.369(8) . ?
C67 C68 1.394(8) . ?
C68 H68 0.9300 . ?
C68 C69 1.390(8) . ?
C69 H69 0.9300 . ?
C70 H70A 0.9600 . ?
C70 H70B 0.9600 . ?
C70 H70C 0.9600 . ?
C71 C72 1.396(8) . ?
C71 C76 1.385(8) . ?
C72 H72 0.9300 . ?
C72 C73 1.376(8) . ?
C73 H73 0.9300 . ?
C73 C74 1.371(10) . ?
C74 H74 0.9300 . ?
C74 C75 1.371(9) . ?
C75 H75 0.9300 . ?
C75 C76 1.358(7) . ?
C76 H76 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
N1 S1 N2 100.5(3) . . ?
C10 O1 C13 118.3(5) . . ?
C1 N1 S1 106.2(4) . . ?
C2 N2 S1 107.0(4) . . ?
C6 N3 H3 115.7 . . ?
C6 N3 C14 128.7(5) . . ?
C14 N3 H3 115.7 . . ?
N1 C1 C2 114.2(5) . . ?
N1 C1 C6 124.2(5) . . ?
C6 C1 C2 121.6(5) . . ?
N2 C2 C1 112.1(5) . . ?
N2 C2 C3 126.9(5) . . ?
C1 C2 C3 120.9(5) . . ?
C2 C3 C7 122.1(5) . . ?
C4 C3 C2 115.0(5) . . ?
C4 C3 C7 122.8(6) . . ?
C3 C4 H4 117.7 . . ?
C3 C4 C5 124.7(6) . . ?
C5 C4 H4 117.7 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.5(5) . . ?
C6 C5 H5 119.3 . . ?
N3 C6 C1 117.2(5) . . ?
C5 C6 N3 126.6(5) . . ?
C5 C6 C1 116.2(5) . . ?
C8 C7 C3 121.6(6) . . ?
C12 C7 C3 122.1(5) . . ?
C12 C7 C8 116.3(5) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 C7 121.9(6) . . ?
C9 C8 H8 119.0 . . ?
C8 C9 H9A 120.1 . . ?
C8 C9 C10 119.7(5) . . ?
C10 C9 H9A 120.1 . . ?
O1 C10 C9 115.4(5) . . ?
C11 C10 O1 124.8(6) . . ?
C11 C10 C9 119.8(6) . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.5(6) . . ?
C12 C11 H11 120.2 . . ?
C7 C12 C11 122.7(5) . . ?
C7 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N3 122.1(5) . . ?
C19 C14 N3 117.7(6) . . ?
C19 C14 C15 120.1(5) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 C14 118.9(6) . . ?
C16 C15 H15 120.6 . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.8(7) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(6) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.6(6) . . ?
C19 C18 H18 120.2 . . ?
C14 C19 C18 120.3(6) . . ?
C14 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
N5 S2 N4 100.7(3) . . ?
C29 O2 C32 118.1(5) . . ?
C20 N4 S2 106.2(4) . . ?
C21 N5 S2 107.1(4) . . ?
C25 N6 H6 115.1 . . ?
C25 N6 C33 129.9(6) . . ?
C33 N6 H6 115.1 . . ?
N4 C20 C21 113.9(5) . . ?
N4 C20 C25 124.5(5) . . ?
C21 C20 C25 121.6(5) . . ?
N5 C21 C20 112.1(5) . . ?
N5 C21 C22 126.9(5) . . ?
C20 C21 C22 121.0(5) . . ?
C21 C22 C26 121.4(5) . . ?
C23 C22 C21 115.1(5) . . ?
C23 C22 C26 123.5(6) . . ?
C22 C23 H23 117.8 . . ?
C22 C23 C24 124.4(6) . . ?
C24 C23 H23 117.8 . . ?
C23 C24 H24 118.9 . . ?
C25 C24 C23 122.1(5) . . ?
C25 C24 H24 118.9 . . ?
N6 C25 C20 117.1(6) . . ?
N6 C25 C24 127.1(5) . . ?
C24 C25 C20 115.7(5) . . ?
C27 C26 C22 121.4(6) . . ?
C27 C26 C31 117.4(5) . . ?
C31 C26 C22 121.1(5) . . ?
C26 C27 H27 119.2 . . ?
C28 C27 C26 121.6(6) . . ?
C28 C27 H27 119.2 . . ?
C27 C28 H28 119.8 . . ?
C27 C28 C29 120.3(6) . . ?
C29 C28 H28 119.8 . . ?
O2 C29 C28 115.0(5) . . ?
O2 C29 C30 125.8(6) . . ?
C30 C29 C28 119.2(6) . . ?
C29 C30 H30 120.1 . . ?
C29 C30 C31 119.9(6) . . ?
C31 C30 H30 120.1 . . ?
C26 C31 H31 119.2 . . ?
C30 C31 C26 121.5(6) . . ?
C30 C31 H31 119.2 . . ?
O2 C32 H32A 109.5 . . ?
O2 C32 H32B 109.5 . . ?
O2 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N6 C33 C34 123.4(6) . . ?
C38 C33 N6 117.8(6) . . ?
C38 C33 C34 118.7(5) . . ?
C33 C34 H34 120.2 . . ?
C35 C34 C33 119.7(6) . . ?
C35 C34 H34 120.2 . . ?
C34 C35 H35 119.4 . . ?
C36 C35 C34 121.3(7) . . ?
C36 C35 H35 119.4 . . ?
C35 C36 H36 120.3 . . ?
C35 C36 C37 119.5(6) . . ?
C37 C36 H36 120.3 . . ?
C36 C37 H37 120.2 . . ?
C38 C37 C36 119.7(6) . . ?
C38 C37 H37 120.2 . . ?
C33 C38 C37 121.2(7) . . ?
C33 C38 H38 119.4 . . ?
C37 C38 H38 119.4 . . ?
N8 S3 N7 101.0(3) . . ?
C48 O3 C51 119.5(5) . . ?
C39 N7 S3 105.9(4) . . ?
C40 N8 S3 107.1(4) . . ?
C44 N9 H9 114.0 . . ?
C44 N9 C52 132.0(5) . . ?
C52 N9 H9 114.0 . . ?
N7 C39 C40 114.3(5) . . ?
N7 C39 C44 124.5(5) . . ?
C40 C39 C44 121.2(5) . . ?
N8 C40 C39 111.7(5) . . ?
N8 C40 C41 126.7(5) . . ?
C41 C40 C39 121.6(5) . . ?
C40 C41 C45 123.3(5) . . ?
C42 C41 C40 114.6(5) . . ?
C42 C41 C45 122.1(5) . . ?
C41 C42 H42 117.7 . . ?
C41 C42 C43 124.7(6) . . ?
C43 C42 H42 117.7 . . ?
C42 C43 H43 119.0 . . ?
C44 C43 C42 122.1(5) . . ?
C44 C43 H43 119.0 . . ?
N9 C44 C39 115.7(5) . . ?
C43 C44 N9 128.5(5) . . ?
C43 C44 C39 115.8(5) . . ?
C46 C45 C41 121.1(6) . . ?
C50 C45 C41 121.8(5) . . ?
C50 C45 C46 117.2(5) . . ?
C45 C46 H46 119.4 . . ?
C47 C46 C45 121.3(6) . . ?
C47 C46 H46 119.4 . . ?
C46 C47 H47 119.9 . . ?
C48 C47 C46 120.1(5) . . ?
C48 C47 H47 119.9 . . ?
O3 C48 C49 125.1(6) . . ?
C47 C48 O3 114.9(5) . . ?
C47 C48 C49 119.9(5) . . ?
C48 C49 H49 120.3 . . ?
C50 C49 C48 119.3(6) . . ?
C50 C49 H49 120.3 . . ?
C45 C50 H50 118.9 . . ?
C49 C50 C45 122.1(5) . . ?
C49 C50 H50 118.9 . . ?
O3 C51 H51A 109.5 . . ?
O3 C51 H51B 109.5 . . ?
O3 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C53 C52 N9 124.3(5) . . ?
C57 C52 N9 116.8(5) . . ?
C57 C52 C53 118.9(5) . . ?
C52 C53 H53 120.1 . . ?
C52 C53 C54 119.8(6) . . ?
C54 C53 H53 120.1 . . ?
C53 C54 H54 119.6 . . ?
C55 C54 C53 120.8(7) . . ?
C55 C54 H54 119.6 . . ?
C54 C55 H55 120.2 . . ?
C54 C55 C56 119.6(6) . . ?
C56 C55 H55 120.2 . . ?
C55 C56 H56 120.2 . . ?
C57 C56 C55 119.7(6) . . ?
C57 C56 H56 120.2 . . ?
C52 C57 H57 119.4 . . ?
C56 C57 C52 121.2(6) . . ?
C56 C57 H57 119.4 . . ?
N11 S4 N10 100.8(3) . . ?
C67 O4 C70 118.6(5) . . ?
C58 N10 S4 105.6(4) . . ?
C59 N11 S4 106.7(4) . . ?
C63 N12 H12A 114.7 . . ?
C63 N12 C71 130.5(5) . . ?
C71 N12 H12A 114.7 . . ?
N10 C58 C59 114.8(5) . . ?
N10 C58 C63 123.2(5) . . ?
C59 C58 C63 121.9(5) . . ?
N11 C59 C58 112.1(5) . . ?
N11 C59 C60 127.0(5) . . ?
C58 C59 C60 120.9(5) . . ?
C59 C60 C64 122.4(5) . . ?
C61 C60 C59 115.1(5) . . ?
C61 C60 C64 122.5(6) . . ?
C60 C61 H61 117.7 . . ?
C60 C61 C62 124.6(6) . . ?
C62 C61 H61 117.7 . . ?
C61 C62 H62 118.9 . . ?
C63 C62 C61 122.2(5) . . ?
C63 C62 H62 118.9 . . ?
N12 C63 C58 116.0(6) . . ?
C62 C63 N12 128.8(5) . . ?
C62 C63 C58 115.2(5) . . ?
C65 C64 C60 121.0(6) . . ?
C69 C64 C60 121.2(5) . . ?
C69 C64 C65 117.7(5) . . ?
C64 C65 H65 119.5 . . ?
C66 C65 C64 120.9(6) . . ?
C66 C65 H65 119.5 . . ?
C65 C66 H66 119.5 . . ?
C67 C66 C65 121.0(6) . . ?
C67 C66 H66 119.5 . . ?
O4 C67 C66 115.2(5) . . ?
O4 C67 C68 125.5(6) . . ?
C66 C67 C68 119.3(6) . . ?
C67 C68 H68 120.2 . . ?
C69 C68 C67 119.5(6) . . ?
C69 C68 H68 120.2 . . ?
C64 C69 C68 121.5(5) . . ?
C64 C69 H69 119.2 . . ?
C68 C69 H69 119.2 . . ?
O4 C70 H70A 109.5 . . ?
O4 C70 H70B 109.5 . . ?
O4 C70 H70C 109.5 . . ?
H70A C70 H70B 109.5 . . ?
H70A C70 H70C 109.5 . . ?
H70B C70 H70C 109.5 . . ?
C72 C71 N12 123.7(5) . . ?
C76 C71 N12 117.6(5) . . ?
C76 C71 C72 118.7(5) . . ?
C71 C72 H72 120.6 . . ?
C73 C72 C71 118.9(6) . . ?
C73 C72 H72 120.6 . . ?
C72 C73 H73 119.1 . . ?
C74 C73 C72 121.8(7) . . ?
C74 C73 H73 119.1 . . ?
C73 C74 H74 120.6 . . ?
C75 C74 C73 118.9(6) . . ?
C75 C74 H74 120.6 . . ?
C74 C75 H75 119.7 . . ?
C76 C75 C74 120.7(6) . . ?
C76 C75 H75 119.7 . . ?
C71 C76 H76 119.4 . . ?
C75 C76 C71 121.1(6) . . ?
C75 C76 H76 119.4 . . ?

_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_170104_pzx_3_8432
_database_code_depnum_ccdc_archive 'CCDC 1813986'
_audit_update_record             
;
2017-12-29 deposited with the CCDC.
2018-07-02 downloaded from the CCDC.
;
_audit_creation_date             2017-01-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H25 N3 O S'
_chemical_formula_sum            'C23 H25 N3 O S'
_chemical_formula_weight         391.52
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 s1'
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'

_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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   18.4571(8)
_cell_length_b                   16.2012(7)
_cell_length_c                   6.5052(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1945.23(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3803
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4274
_cell_measurement_theta_min      3.1252
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.929
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11960
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.346
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -13.00   72.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       10.6871   38.0000   60.0000 85

#__ type_ start__ end____ width___ exp.time_
  2 omega  -65.00   37.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       10.6871  -38.0000 -120.0000 102

#__ type_ start__ end____ width___ exp.time_
  3 omega  -73.00   21.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.5621  -77.0000  120.0000 94
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0143489000
_diffrn_orient_matrix_UB_12      -0.0399007000
_diffrn_orient_matrix_UB_13      0.0191115000
_diffrn_orient_matrix_UB_21      -0.0295723000
_diffrn_orient_matrix_UB_22      0.0179201000
_diffrn_orient_matrix_UB_23      0.0534784000
_diffrn_orient_matrix_UB_31      -0.0199145000
_diffrn_orient_matrix_UB_32      0.0021057000
_diffrn_orient_matrix_UB_33      -0.0930427000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                2805
_reflns_number_total             3514
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 986 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3514
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.015
_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)+(0.0575P)²+0.0835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1107
_refine_special_details          ?
_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:
 C16(H16), C18(H18), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B), C19(H19A,H19B), C20(H20A,H20B), C22(H22A,
 H22B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C3(H3A), C4(H4), C8(H8), C9(H9), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.79097(5) 0.49341(7) 0.7162(2) 0.0642(4) Uani 1 1 d . . . . .
O1 O 0.67439(16) 0.23987(17) -0.3025(4) 0.0668(8) Uani 1 1 d . . . . .
N1 N 0.75543(15) 0.45409(19) 0.5125(6) 0.0540(9) Uani 1 1 d . . . . .
N2 N 0.73520(16) 0.56709(17) 0.7622(6) 0.0524(8) Uani 1 1 d . . . . .
N3 N 0.61972(18) 0.67605(17) 0.7589(6) 0.0581(9) Uani 1 1 d . . . . .
H3 H 0.647583 0.668424 0.863139 0.070 Uiso 1 1 calc R . . . .
C1 C 0.69508(18) 0.4977(2) 0.4719(6) 0.0420(8) Uani 1 1 d . . . . .
C2 C 0.64490(19) 0.4847(2) 0.3081(6) 0.0452(9) Uani 1 1 d . . . . .
C3 C 0.5878(2) 0.5384(2) 0.3076(7) 0.0539(10) Uani 1 1 d . . . . .
H3A H 0.553098 0.531689 0.205390 0.065 Uiso 1 1 calc R . . . .
C4 C 0.5772(2) 0.6033(2) 0.4492(7) 0.0589(11) Uani 1 1 d . . . . .
H4 H 0.537278 0.637711 0.433272 0.071 Uiso 1 1 calc R . . . .
C5 C 0.6236(2) 0.6172(2) 0.6083(6) 0.0476(9) Uani 1 1 d . . . . .
C6 C 0.6838(2) 0.5626(2) 0.6165(6) 0.0457(9) Uani 1 1 d . . . . .
C7 C 0.65343(18) 0.4191(2) 0.1537(6) 0.0425(9) Uani 1 1 d . . . . .
C8 C 0.69190(19) 0.3465(2) 0.1914(7) 0.0484(9) Uani 1 1 d . . . . .
H8 H 0.712889 0.338997 0.320012 0.058 Uiso 1 1 calc R . . . .
C9 C 0.7000(2) 0.2856(2) 0.0453(6) 0.0509(10) Uani 1 1 d . . . . .
H9 H 0.726338 0.238205 0.075561 0.061 Uiso 1 1 calc R . . . .
C10 C 0.6691(2) 0.2952(2) -0.1447(6) 0.0497(10) Uani 1 1 d . . . . .
C11 C 0.6291(2) 0.3657(2) -0.1860(7) 0.0521(10) Uani 1 1 d . . . . .
H11 H 0.606841 0.371892 -0.313331 0.063 Uiso 1 1 calc R . . . .
C12 C 0.62202(19) 0.4264(2) -0.0407(6) 0.0489(9) Uani 1 1 d . . . . .
H12 H 0.595646 0.473626 -0.072320 0.059 Uiso 1 1 calc R . . . .
C13 C 0.7141(3) 0.1674(3) -0.2695(9) 0.0787(14) Uani 1 1 d . . . . .
H13A H 0.716075 0.136011 -0.394559 0.118 Uiso 1 1 calc GR . . . .
H13B H 0.691128 0.135186 -0.164209 0.118 Uiso 1 1 calc GR . . . .
H13C H 0.762428 0.181313 -0.227081 0.118 Uiso 1 1 calc GR . . . .
C14 C 0.57465(18) 0.7500(2) 0.7663(6) 0.0435(8) Uani 1 1 d . . . . .
C15 C 0.5842(2) 0.8028(2) 0.5761(6) 0.0511(10) Uani 1 1 d . . . . .
H15A H 0.568153 0.772424 0.455945 0.061 Uiso 1 1 calc R . . . .
H15B H 0.635108 0.816009 0.558181 0.061 Uiso 1 1 calc R . . . .
C16 C 0.5406(2) 0.8821(2) 0.5965(7) 0.0574(11) Uani 1 1 d . . . . .
H16 H 0.546569 0.915437 0.471923 0.069 Uiso 1 1 calc R . . . .
C17 C 0.5669(2) 0.9307(2) 0.7807(7) 0.0600(11) Uani 1 1 d . . . . .
H17A H 0.617530 0.944870 0.763171 0.072 Uiso 1 1 calc R . . . .
H17B H 0.539338 0.981420 0.793285 0.072 Uiso 1 1 calc R . . . .
C18 C 0.5574(2) 0.8790(2) 0.9724(7) 0.0549(10) Uani 1 1 d . . . . .
H18 H 0.575173 0.909913 1.091661 0.066 Uiso 1 1 calc R . . . .
C19 C 0.6004(2) 0.7993(2) 0.9509(6) 0.0491(9) Uani 1 1 d . . . . .
H19A H 0.651447 0.812175 0.935122 0.059 Uiso 1 1 calc R . . . .
H19B H 0.594795 0.766453 1.074585 0.059 Uiso 1 1 calc R . . . .
C20 C 0.4945(2) 0.7300(2) 0.7972(7) 0.0558(10) Uani 1 1 d . . . . .
H20A H 0.476775 0.698071 0.681474 0.067 Uiso 1 1 calc R . . . .
H20B H 0.488365 0.697278 0.920818 0.067 Uiso 1 1 calc R . . . .
C21 C 0.4514(2) 0.8101(3) 0.8156(7) 0.0615(11) Uani 1 1 d . . . . .
H21 H 0.399902 0.796910 0.833033 0.074 Uiso 1 1 calc R . . . .
C22 C 0.4611(2) 0.8607(3) 0.6241(8) 0.0629(12) Uani 1 1 d . . . . .
H22A H 0.432728 0.910970 0.634259 0.076 Uiso 1 1 calc R . . . .
H22B H 0.444042 0.829844 0.505787 0.076 Uiso 1 1 calc R . . . .
C23 C 0.4779(2) 0.8585(3) 1.0029(8) 0.0667(12) Uani 1 1 d . . . . .
H23A H 0.450049 0.908871 1.017909 0.080 Uiso 1 1 calc R . . . .
H23B H 0.471771 0.825716 1.126472 0.080 Uiso 1 1 calc 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 N1 1.610(3) . ?
S1 N2 1.604(3) . ?
O1 C10 1.367(4) . ?
O1 C13 1.401(5) . ?
N1 C1 1.346(4) . ?
N2 C6 1.343(5) . ?
N3 H3 0.8600 . ?
N3 C5 1.368(5) . ?
N3 C14 1.459(4) . ?
C1 C2 1.427(5) . ?
C1 C6 1.426(5) . ?
C2 C3 1.367(5) . ?
C2 C7 1.471(5) . ?
C3 H3A 0.9300 . ?
C3 C4 1.411(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.363(5) . ?
C5 C6 1.422(5) . ?
C7 C8 1.395(5) . ?
C7 C12 1.396(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.369(6) . ?
C10 C11 1.388(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.370(5) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.515(5) . ?
C14 C19 1.519(5) . ?
C14 C20 1.527(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.523(5) . ?
C16 H16 0.9800 . ?
C16 C17 1.513(6) . ?
C16 C22 1.518(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.512(6) . ?
C18 H18 0.9800 . ?
C18 C19 1.522(5) . ?
C18 C23 1.517(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.527(5) . ?
C21 H21 0.9800 . ?
C21 C22 1.503(6) . ?
C21 C23 1.530(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?

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
N2 S1 N1 100.76(17) . . ?
C10 O1 C13 118.1(3) . . ?
C1 N1 S1 106.9(3) . . ?
C6 N2 S1 106.3(3) . . ?
C5 N3 H3 115.6 . . ?
C5 N3 C14 128.7(3) . . ?
C14 N3 H3 115.6 . . ?
N1 C1 C2 127.3(3) . . ?
N1 C1 C6 112.2(3) . . ?
C6 C1 C2 120.5(3) . . ?
C1 C2 C7 123.2(3) . . ?
C3 C2 C1 114.1(3) . . ?
C3 C2 C7 122.8(3) . . ?
C2 C3 H3A 117.3 . . ?
C2 C3 C4 125.4(4) . . ?
C4 C3 H3A 117.3 . . ?
C3 C4 H4 118.9 . . ?
C5 C4 C3 122.1(4) . . ?
C5 C4 H4 118.9 . . ?
N3 C5 C6 116.6(3) . . ?
C4 C5 N3 128.8(3) . . ?
C4 C5 C6 114.6(3) . . ?
N2 C6 C1 113.8(3) . . ?
N2 C6 C5 123.0(3) . . ?
C5 C6 C1 123.2(3) . . ?
C8 C7 C2 122.9(3) . . ?
C8 C7 C12 116.2(3) . . ?
C12 C7 C2 120.9(3) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 C7 122.5(4) . . ?
C9 C8 H8 118.7 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.7(4) . . ?
C10 C9 H9 120.1 . . ?
O1 C10 C9 125.0(3) . . ?
O1 C10 C11 115.6(3) . . ?
C9 C10 C11 119.3(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.5(4) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 H12 119.2 . . ?
C11 C12 C7 121.7(3) . . ?
C11 C12 H12 119.2 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 111.7(3) . . ?
N3 C14 C19 106.2(3) . . ?
N3 C14 C20 112.5(3) . . ?
C15 C14 C19 108.2(3) . . ?
C15 C14 C20 109.9(3) . . ?
C19 C14 C20 108.1(3) . . ?
C14 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
C14 C15 C16 110.1(3) . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C15 C16 H16 109.4 . . ?
C17 C16 C15 109.8(3) . . ?
C17 C16 H16 109.4 . . ?
C17 C16 C22 109.6(4) . . ?
C22 C16 C15 109.2(3) . . ?
C22 C16 H16 109.4 . . ?
C16 C17 H17A 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
C18 C17 C16 109.2(3) . . ?
C18 C17 H17A 109.8 . . ?
C18 C17 H17B 109.8 . . ?
C17 C18 H18 109.4 . . ?
C17 C18 C19 109.5(3) . . ?
C17 C18 C23 109.9(4) . . ?
C19 C18 H18 109.4 . . ?
C23 C18 H18 109.4 . . ?
C23 C18 C19 109.3(3) . . ?
C14 C19 C18 110.8(3) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
C14 C20 H20A 109.8 . . ?
C14 C20 H20B 109.8 . . ?
H20A C20 H20B 108.2 . . ?
C21 C20 C14 109.6(3) . . ?
C21 C20 H20A 109.8 . . ?
C21 C20 H20B 109.8 . . ?
C20 C21 H21 109.3 . . ?
C20 C21 C23 109.3(4) . . ?
C22 C21 C20 109.7(3) . . ?
C22 C21 H21 109.3 . . ?
C22 C21 C23 110.0(3) . . ?
C23 C21 H21 109.3 . . ?
C16 C22 H22A 109.7 . . ?
C16 C22 H22B 109.7 . . ?
C21 C22 C16 109.7(3) . . ?
C21 C22 H22A 109.7 . . ?
C21 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C18 C23 C21 108.5(4) . . ?
C18 C23 H23A 110.0 . . ?
C18 C23 H23B 110.0 . . ?
C21 C23 H23A 110.0 . . ?
C21 C23 H23B 110.0 . . ?
H23A C23 H23B 108.4 . . ?

_shelx_SHELXL_version_number     2016/6
_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_170306_pzx_3_8464
_database_code_depnum_ccdc_archive 'CCDC 1813989'
_audit_update_record             
;
2017-12-29 deposited with the CCDC.
2018-07-02 downloaded from the CCDC.
;
_audit_creation_date             2017-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 N4 O S'
_chemical_formula_sum            'C20 H14 N4 O S'
_chemical_formula_weight         358.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 s1'
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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1703(8)
_cell_length_b                   19.850(3)
_cell_length_c                   18.7033(18)
_cell_angle_alpha                90
_cell_angle_beta                 102.929(9)
_cell_angle_gamma                90
_cell_volume                     3318.2(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2643
_cell_measurement_temperature    170
_cell_measurement_theta_max      29.4847
_cell_measurement_theta_min      3.0610
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.903
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13529
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         3.067
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -46.00    2.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.7183  -38.0000    0.0000 48

#__ type_ start__ end____ width___ exp.time_
  2 omega  -91.00   21.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.7183  -77.0000 -180.0000 112

#__ type_ start__ end____ width___ exp.time_
  3 omega  -89.00  -61.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.7183  -38.0000    0.0000 28
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0354508000
_diffrn_orient_matrix_UB_12      0.0295396000
_diffrn_orient_matrix_UB_13      0.0169154000
_diffrn_orient_matrix_UB_21      0.0422072000
_diffrn_orient_matrix_UB_22      -0.0198379000
_diffrn_orient_matrix_UB_23      0.0289022000
_diffrn_orient_matrix_UB_31      0.0569615000
_diffrn_orient_matrix_UB_32      -0.0037394000
_diffrn_orient_matrix_UB_33      -0.0198137000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4323
_reflns_number_total             5971
_reflns_odcompleteness_completeness 99.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         5971
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0567P)²+0.9827P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1339
_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:
 N3(H3), C3(H3A), C4(H4), C8(H8), C9(H9), C11(H11), C12(H12), C15(H15),
 C16(H16), C18(H18), C19(H19), N7(H7), C23(H23), C24(H24), C28(H28), C29(H29),
 C31(H31), C32(H32), C35(H35), C36(H36), C38(H38), C39(H39)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C33(H33A,H33B,H33C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 1.10439(7) 0.72018(3) 0.57254(3) 0.0392(2) Uani 1 1 d . . . . .
O1 O 0.71454(16) 0.39403(9) 0.35109(9) 0.0356(4) Uani 1 1 d . . . . .
N1 N 0.9983(2) 0.66567(10) 0.52194(10) 0.0342(5) Uani 1 1 d . . . . .
N2 N 1.0415(2) 0.78950(10) 0.53185(10) 0.0340(5) Uani 1 1 d . . . . .
N3 N 0.8890(2) 0.88554(10) 0.43456(10) 0.0329(5) Uani 1 1 d . . . . .
H3 H 0.975145 0.891849 0.465813 0.039 Uiso 1 1 calc R . . . .
N4 N 0.5838(3) 1.18203(13) 0.29875(14) 0.0583(7) Uani 1 1 d . . . . .
C1 C 0.9058(2) 0.70075(12) 0.46802(12) 0.0274(5) Uani 1 1 d . . . . .
C2 C 0.7932(2) 0.67333(12) 0.40940(12) 0.0268(5) Uani 1 1 d . . . . .
C3 C 0.7122(2) 0.72118(13) 0.36333(12) 0.0306(6) Uani 1 1 d . . . . .
H3A H 0.634136 0.705597 0.324503 0.037 Uiso 1 1 calc R . . . .
C4 C 0.7363(2) 0.79160(13) 0.36948(13) 0.0317(6) Uani 1 1 d . . . . .
H4 H 0.675364 0.820735 0.334921 0.038 Uiso 1 1 calc R . . . .
C5 C 0.8457(2) 0.81876(12) 0.42425(12) 0.0280(5) Uani 1 1 d . . . . .
C6 C 0.9311(2) 0.77146(12) 0.47443(12) 0.0279(5) Uani 1 1 d . . . . .
C7 C 0.7686(2) 0.60012(12) 0.39676(11) 0.0264(5) Uani 1 1 d . . . . .
C8 C 0.8862(2) 0.55356(13) 0.41508(12) 0.0282(5) Uani 1 1 d . . . . .
H8 H 0.983034 0.568877 0.438943 0.034 Uiso 1 1 calc R . . . .
C9 C 0.8640(2) 0.48603(13) 0.39911(12) 0.0293(5) Uani 1 1 d . . . . .
H9 H 0.945593 0.455587 0.412041 0.035 Uiso 1 1 calc R . . . .
C10 C 0.7233(2) 0.46181(12) 0.36423(12) 0.0268(5) Uani 1 1 d . . . . .
C11 C 0.6049(2) 0.50685(12) 0.34632(11) 0.0276(5) Uani 1 1 d . . . . .
H11 H 0.508038 0.491269 0.322942 0.033 Uiso 1 1 calc R . . . .
C12 C 0.6287(2) 0.57482(12) 0.36273(12) 0.0273(5) Uani 1 1 d . . . . .
H12 H 0.546633 0.605060 0.350277 0.033 Uiso 1 1 calc R . . . .
C13 C 0.5750(2) 0.36707(14) 0.31155(14) 0.0393(6) Uani 1 1 d . . . . .
H13A H 0.545127 0.389737 0.263967 0.059 Uiso 1 1 calc GR . . . .
H13B H 0.498264 0.374330 0.339773 0.059 Uiso 1 1 calc GR . . . .
H13C H 0.585947 0.318669 0.303828 0.059 Uiso 1 1 calc GR . . . .
C14 C 0.8196(2) 0.94415(12) 0.40395(12) 0.0256(5) Uani 1 1 d . . . . .
C15 C 0.6667(2) 0.94941(13) 0.37335(12) 0.0293(5) Uani 1 1 d . . . . .
H15 H 0.604253 0.910921 0.370880 0.035 Uiso 1 1 calc R . . . .
C16 C 0.6061(2) 1.01055(13) 0.34663(12) 0.0306(6) Uani 1 1 d . . . . .
H16 H 0.502039 1.013556 0.325487 0.037 Uiso 1 1 calc R . . . .
C17 C 0.6952(2) 1.06796(13) 0.35017(12) 0.0291(5) Uani 1 1 d . . . . .
C18 C 0.8479(2) 1.06299(12) 0.38155(12) 0.0288(5) Uani 1 1 d . . . . .
H18 H 0.909965 1.101695 0.384888 0.035 Uiso 1 1 calc R . . . .
C19 C 0.9082(2) 1.00212(12) 0.40758(11) 0.0266(5) Uani 1 1 d . . . . .
H19 H 1.012386 0.999198 0.428539 0.032 Uiso 1 1 calc R . . . .
C20 C 0.6321(3) 1.13140(14) 0.32187(13) 0.0376(6) Uani 1 1 d . . . . .
S2 S 0.61704(6) 0.77754(3) 0.55926(3) 0.03615(19) Uani 1 1 d . . . . .
O2 O 0.21773(17) 1.10906(9) 0.35673(8) 0.0345(4) Uani 1 1 d . . . . .
N5 N 0.5170(2) 0.83326(10) 0.50729(10) 0.0317(5) Uani 1 1 d . . . . .
N6 N 0.5309(2) 0.70924(10) 0.52789(10) 0.0334(5) Uani 1 1 d . . . . .
N7 N 0.3295(2) 0.61501(10) 0.45091(10) 0.0337(5) Uani 1 1 d . . . . .
H7 H 0.379760 0.608362 0.496260 0.040 Uiso 1 1 calc R . . . .
N8 N 0.1219(3) 0.31827(13) 0.28075(13) 0.0498(6) Uani 1 1 d . . . . .
C21 C 0.4058(2) 0.79951(12) 0.46182(12) 0.0276(5) Uani 1 1 d . . . . .
C22 C 0.2893(2) 0.82809(12) 0.40537(12) 0.0277(5) Uani 1 1 d . . . . .
C23 C 0.1906(2) 0.78145(13) 0.36654(12) 0.0311(6) Uani 1 1 d . . . . .
H23 H 0.110994 0.797981 0.329067 0.037 Uiso 1 1 calc R . . . .
C24 C 0.1988(2) 0.71106(13) 0.37824(13) 0.0324(6) Uani 1 1 d . . . . .
H24 H 0.125493 0.682832 0.348850 0.039 Uiso 1 1 calc R . . . .
C25 C 0.3099(2) 0.68246(12) 0.43096(12) 0.0294(5) Uani 1 1 d . . . . .
C26 C 0.4154(2) 0.72831(12) 0.47355(12) 0.0277(5) Uani 1 1 d . . . . .
C27 C 0.2739(2) 0.90144(12) 0.39149(12) 0.0269(5) Uani 1 1 d . . . . .
C28 C 0.3187(2) 0.94953(12) 0.44726(12) 0.0269(5) Uani 1 1 d . . . . .
H28 H 0.362539 0.934678 0.495567 0.032 Uiso 1 1 calc R . . . .
C29 C 0.3008(2) 1.01743(12) 0.43381(11) 0.0258(5) Uani 1 1 d . . . . .
H29 H 0.333394 1.048722 0.472522 0.031 Uiso 1 1 calc R . . . .
C30 C 0.2349(2) 1.04069(12) 0.36341(12) 0.0260(5) Uani 1 1 d . . . . .
C31 C 0.1918(2) 0.99474(12) 0.30717(12) 0.0276(5) Uani 1 1 d . . . . .
H31 H 0.148743 1.009935 0.258896 0.033 Uiso 1 1 calc R . . . .
C32 C 0.2114(2) 0.92629(13) 0.32139(12) 0.0289(6) Uani 1 1 d . . . . .
H32 H 0.181486 0.895292 0.282148 0.035 Uiso 1 1 calc R . . . .
C33 C 0.1551(3) 1.13568(14) 0.28551(13) 0.0460(7) Uani 1 1 d . . . . .
H33A H 0.217233 1.122344 0.251554 0.069 Uiso 1 1 calc GR . . . .
H33B H 0.151400 1.184937 0.288135 0.069 Uiso 1 1 calc GR . . . .
H33C H 0.053555 1.118002 0.267979 0.069 Uiso 1 1 calc GR . . . .
C34 C 0.2840(2) 0.55644(12) 0.41201(12) 0.0262(5) Uani 1 1 d . . . . .
C35 C 0.2252(2) 0.55448(12) 0.33617(12) 0.0277(5) Uani 1 1 d . . . . .
H35 H 0.212982 0.594987 0.308414 0.033 Uiso 1 1 calc R . . . .
C36 C 0.1849(2) 0.49337(12) 0.30181(12) 0.0287(5) Uani 1 1 d . . . . .
H36 H 0.144941 0.492277 0.250375 0.034 Uiso 1 1 calc R . . . .
C37 C 0.2021(2) 0.43332(12) 0.34163(12) 0.0265(5) Uani 1 1 d . . . . .
C38 C 0.2635(2) 0.43536(13) 0.41720(12) 0.0277(5) Uani 1 1 d . . . . .
H38 H 0.277146 0.394805 0.444869 0.033 Uiso 1 1 calc R . . . .
C39 C 0.3041(2) 0.49574(12) 0.45125(12) 0.0271(5) Uani 1 1 d . . . . .
H39 H 0.346587 0.496507 0.502457 0.033 Uiso 1 1 calc R . . . .
C40 C 0.1569(3) 0.36976(14) 0.30700(13) 0.0342(6) Uani 1 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
S1 N1 1.613(2) . ?
S1 N2 1.615(2) . ?
O1 C10 1.367(3) . ?
O1 C13 1.431(3) . ?
N1 C1 1.356(3) . ?
N2 C6 1.349(3) . ?
N3 H3 0.8800 . ?
N3 C5 1.385(3) . ?
N3 C14 1.387(3) . ?
N4 C20 1.143(3) . ?
C1 C2 1.434(3) . ?
C1 C6 1.423(3) . ?
C2 C3 1.382(3) . ?
C2 C7 1.481(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.416(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.374(3) . ?
C5 C6 1.431(3) . ?
C7 C8 1.404(3) . ?
C7 C12 1.392(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.379(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.394(3) . ?
C10 C11 1.388(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(3) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.395(3) . ?
C14 C19 1.401(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.395(3) . ?
C17 C18 1.395(3) . ?
C17 C20 1.437(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.372(3) . ?
C19 H19 0.9500 . ?
S2 N5 1.616(2) . ?
S2 N6 1.612(2) . ?
O2 C30 1.369(3) . ?
O2 C33 1.429(3) . ?
N5 C21 1.351(3) . ?
N6 C26 1.348(3) . ?
N7 H7 0.8800 . ?
N7 C25 1.391(3) . ?
N7 C34 1.386(3) . ?
N8 C40 1.148(3) . ?
C21 C22 1.440(3) . ?
C21 C26 1.430(3) . ?
C22 C23 1.382(3) . ?
C22 C27 1.480(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.414(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.372(3) . ?
C25 C26 1.433(3) . ?
C27 C28 1.406(3) . ?
C27 C32 1.398(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.374(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.399(3) . ?
C30 C31 1.381(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.389(3) . ?
C32 H32 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 C35 1.401(3) . ?
C34 C39 1.401(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.384(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.396(3) . ?
C37 C38 1.400(3) . ?
C37 C40 1.436(3) . ?
C38 H38 0.9500 . ?
C38 C39 1.369(3) . ?
C39 H39 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 S1 N2 100.97(10) . . ?
C10 O1 C13 118.10(18) . . ?
C1 N1 S1 106.68(17) . . ?
C6 N2 S1 105.91(16) . . ?
C5 N3 H3 114.6 . . ?
C5 N3 C14 130.88(19) . . ?
C14 N3 H3 114.6 . . ?
N1 C1 C2 126.7(2) . . ?
N1 C1 C6 112.36(19) . . ?
C6 C1 C2 121.0(2) . . ?
C1 C2 C7 123.5(2) . . ?
C3 C2 C1 114.2(2) . . ?
C3 C2 C7 122.2(2) . . ?
C2 C3 H3A 117.4 . . ?
C2 C3 C4 125.1(2) . . ?
C4 C3 H3A 117.4 . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.5(2) . . ?
C5 C4 H4 119.2 . . ?
N3 C5 C6 116.02(19) . . ?
C4 C5 N3 128.2(2) . . ?
C4 C5 C6 115.7(2) . . ?
N2 C6 C1 114.1(2) . . ?
N2 C6 C5 123.5(2) . . ?
C1 C6 C5 122.5(2) . . ?
C8 C7 C2 121.69(19) . . ?
C12 C7 C2 121.3(2) . . ?
C12 C7 C8 117.0(2) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.3(2) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.9(2) . . ?
C10 C9 H9 119.6 . . ?
O1 C10 C9 115.76(19) . . ?
O1 C10 C11 125.4(2) . . ?
C11 C10 C9 118.8(2) . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C7 C12 H12 118.9 . . ?
C11 C12 C7 122.3(2) . . ?
C11 C12 H12 118.9 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 124.0(2) . . ?
N3 C14 C19 117.47(19) . . ?
C15 C14 C19 118.5(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(2) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.4 . . ?
C15 C16 C17 121.1(2) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C18 118.9(2) . . ?
C16 C17 C20 121.0(2) . . ?
C18 C17 C20 120.0(2) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.9(2) . . ?
C19 C18 H18 120.1 . . ?
C14 C19 H19 119.2 . . ?
C18 C19 C14 121.5(2) . . ?
C18 C19 H19 119.2 . . ?
N4 C20 C17 178.9(3) . . ?
N6 S2 N5 101.00(10) . . ?
C30 O2 C33 117.76(19) . . ?
C21 N5 S2 106.64(17) . . ?
C26 N6 S2 106.06(17) . . ?
C25 N7 H7 114.3 . . ?
C34 N7 H7 114.3 . . ?
C34 N7 C25 131.40(19) . . ?
N5 C21 C22 126.7(2) . . ?
N5 C21 C26 112.44(19) . . ?
C26 C21 C22 120.8(2) . . ?
C21 C22 C27 122.9(2) . . ?
C23 C22 C21 114.4(2) . . ?
C23 C22 C27 122.7(2) . . ?
C22 C23 H23 117.5 . . ?
C22 C23 C24 125.1(2) . . ?
C24 C23 H23 117.5 . . ?
C23 C24 H24 119.1 . . ?
C25 C24 C23 121.7(2) . . ?
C25 C24 H24 119.1 . . ?
N7 C25 C26 115.55(19) . . ?
C24 C25 N7 128.5(2) . . ?
C24 C25 C26 115.9(2) . . ?
N6 C26 C21 113.8(2) . . ?
N6 C26 C25 124.0(2) . . ?
C21 C26 C25 122.1(2) . . ?
C28 C27 C22 122.5(2) . . ?
C32 C27 C22 121.0(2) . . ?
C32 C27 C28 116.5(2) . . ?
C27 C28 H28 119.1 . . ?
C29 C28 C27 121.8(2) . . ?
C29 C28 H28 119.1 . . ?
C28 C29 H29 119.8 . . ?
C28 C29 C30 120.3(2) . . ?
C30 C29 H29 119.8 . . ?
O2 C30 C29 115.5(2) . . ?
O2 C30 C31 125.3(2) . . ?
C31 C30 C29 119.2(2) . . ?
C30 C31 H31 120.1 . . ?
C30 C31 C32 119.8(2) . . ?
C32 C31 H31 120.1 . . ?
C27 C32 H32 118.9 . . ?
C31 C32 C27 122.2(2) . . ?
C31 C32 H32 118.9 . . ?
O2 C33 H33A 109.5 . . ?
O2 C33 H33B 109.5 . . ?
O2 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N7 C34 C35 123.9(2) . . ?
N7 C34 C39 117.24(19) . . ?
C35 C34 C39 118.8(2) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 C34 119.8(2) . . ?
C36 C35 H35 120.1 . . ?
C35 C36 H36 119.5 . . ?
C35 C36 C37 121.0(2) . . ?
C37 C36 H36 119.5 . . ?
C36 C37 C38 119.1(2) . . ?
C36 C37 C40 121.5(2) . . ?
C38 C37 C40 119.4(2) . . ?
C37 C38 H38 120.0 . . ?
C39 C38 C37 120.1(2) . . ?
C39 C38 H38 120.0 . . ?
C34 C39 H39 119.4 . . ?
C38 C39 C34 121.3(2) . . ?
C38 C39 H39 119.4 . . ?
N8 C40 C37 178.5(3) . . ?

_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_170104_pzx_3_8458
_database_code_depnum_ccdc_archive 'CCDC 1813990'
_audit_update_record             
;
2017-12-29 deposited with the CCDC.
2018-07-02 downloaded from the CCDC.
;
_audit_creation_date             2017-01-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H19 N3 O S'
_chemical_formula_sum            'C25 H19 N3 O S'
_chemical_formula_weight         409.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 s1'
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'

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

_cell_length_a                   10.2716(9)
_cell_length_b                   10.9546(10)
_cell_length_c                   11.2649(10)
_cell_angle_alpha                99.583(8)
_cell_angle_beta                 111.659(8)
_cell_angle_gamma                113.273(9)
_cell_volume                     1007.19(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1960
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2479
_cell_measurement_theta_min      3.4898
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.917
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6254
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         3.497
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -55.00   34.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.8433  -38.0000 -180.0000 89

#__ type_ start__ end____ width___ exp.time_
  2 omega  -16.00   80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.8433   38.0000    0.0000 96

#__ type_ start__ end____ width___ exp.time_
  3 omega  -69.00   21.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -12.7183  -77.0000   60.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0759161000
_diffrn_orient_matrix_UB_12      0.0164893000
_diffrn_orient_matrix_UB_13      0.0524902000
_diffrn_orient_matrix_UB_21      -0.0389031000
_diffrn_orient_matrix_UB_22      -0.0599583000
_diffrn_orient_matrix_UB_23      0.0154222000
_diffrn_orient_matrix_UB_31      0.0081307000
_diffrn_orient_matrix_UB_32      -0.0432255000
_diffrn_orient_matrix_UB_33      -0.0480183000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2685
_reflns_number_total             3681
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.066(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3681
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.023
_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)+(0.0495P)²+0.2002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1211
_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(H3), C4(H4), C8(H8), C9(H9), C11(H11), C12(H12), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.16433(7) 0.58722(6) 0.19572(6) 0.0563(2) Uani 1 1 d . . . . .
O1 O 0.98742(19) 1.14209(17) 0.89501(16) 0.0599(5) Uani 1 1 d . . . . .
N1 N 0.3406(2) 0.70977(18) 0.31565(18) 0.0449(5) Uani 1 1 d . . . . .
N2 N 0.1769(2) 0.61112(17) 0.06256(18) 0.0448(5) Uani 1 1 d . . . . .
N3 N 0.3008(2) 0.71289(18) -0.11999(17) 0.0417(4) Uani 1 1 d . . . . .
C1 C 0.4210(2) 0.77986(19) 0.2555(2) 0.0348(5) Uani 1 1 d . . . . .
C2 C 0.5837(2) 0.8967(2) 0.3223(2) 0.0355(5) Uani 1 1 d . . . . .
C3 C 0.6363(3) 0.9439(2) 0.2350(2) 0.0452(5) Uani 1 1 d . . . . .
H3 H 0.740802 1.020075 0.273228 0.054 Uiso 1 1 calc R . . . .
C4 C 0.5433(3) 0.8850(2) 0.0914(2) 0.0455(5) Uani 1 1 d . . . . .
H4 H 0.589304 0.923114 0.039707 0.055 Uiso 1 1 calc R . . . .
C5 C 0.3892(2) 0.7749(2) 0.0248(2) 0.0373(5) Uani 1 1 d . . . . .
C6 C 0.3252(2) 0.7210(2) 0.1090(2) 0.0362(5) Uani 1 1 d . . . . .
C7 C 0.6892(2) 0.9614(2) 0.4722(2) 0.0369(5) Uani 1 1 d . . . . .
C8 C 0.6327(3) 0.9403(2) 0.5657(2) 0.0415(5) Uani 1 1 d . . . . .
H8 H 0.522684 0.882233 0.533262 0.050 Uiso 1 1 calc R . . . .
C9 C 0.7345(3) 1.0026(2) 0.7043(2) 0.0435(5) Uani 1 1 d . . . . .
H9 H 0.692635 0.985765 0.764084 0.052 Uiso 1 1 calc R . . . .
C10 C 0.8977(3) 1.0896(2) 0.7564(2) 0.0445(5) Uani 1 1 d . . . . .
C11 C 0.9575(3) 1.1134(3) 0.6667(3) 0.0639(7) Uani 1 1 d . . . . .
H11 H 1.067517 1.172440 0.699892 0.077 Uiso 1 1 calc R . . . .
C12 C 0.8545(3) 1.0496(3) 0.5277(2) 0.0600(7) Uani 1 1 d . . . . .
H12 H 0.897205 1.066246 0.468430 0.072 Uiso 1 1 calc R . . . .
C13 C 1.1543(3) 1.2406(4) 0.9552(3) 0.0968(11) Uani 1 1 d . . . . .
H13A H 1.206358 1.194783 0.927075 0.145 Uiso 1 1 calc GR . . . .
H13B H 1.200927 1.273377 1.053385 0.145 Uiso 1 1 calc GR . . . .
H13C H 1.169036 1.320349 0.926181 0.145 Uiso 1 1 calc GR . . . .
C14 C 0.1621(2) 0.7199(2) -0.1942(2) 0.0361(5) Uani 1 1 d . . . . .
C15 C 0.0651(3) 0.6439(2) -0.3339(2) 0.0502(6) Uani 1 1 d . . . . .
H15 H 0.089454 0.584069 -0.379275 0.060 Uiso 1 1 calc R . . . .
C16 C -0.0671(3) 0.6561(3) -0.4062(3) 0.0584(6) Uani 1 1 d . . . . .
H16 H -0.130554 0.605227 -0.500242 0.070 Uiso 1 1 calc R . . . .
C17 C -0.1070(3) 0.7421(3) -0.3419(3) 0.0596(7) Uani 1 1 d . . . . .
H17 H -0.195744 0.750948 -0.391622 0.072 Uiso 1 1 calc R . . . .
C18 C -0.0142(3) 0.8142(2) -0.2039(3) 0.0505(6) Uani 1 1 d . . . . .
H18 H -0.041620 0.871300 -0.159021 0.061 Uiso 1 1 calc R . . . .
C19 C 0.1194(3) 0.8044(2) -0.1293(2) 0.0398(5) Uani 1 1 d . . . . .
H19 H 0.181120 0.854734 -0.035041 0.048 Uiso 1 1 calc R . . . .
C20 C 0.3658(2) 0.6495(2) -0.1865(2) 0.0364(5) Uani 1 1 d . . . . .
C21 C 0.3853(3) 0.5401(2) -0.1570(3) 0.0549(6) Uani 1 1 d . . . . .
H21 H 0.356067 0.507660 -0.094625 0.066 Uiso 1 1 calc R . . . .
C22 C 0.4479(3) 0.4771(3) -0.2191(3) 0.0657(7) Uani 1 1 d . . . . .
H22 H 0.461066 0.402667 -0.198335 0.079 Uiso 1 1 calc R . . . .
C23 C 0.4908(3) 0.5240(3) -0.3111(3) 0.0607(7) Uani 1 1 d . . . . .
H23 H 0.532716 0.481517 -0.353326 0.073 Uiso 1 1 calc R . . . .
C24 C 0.4716(3) 0.6331(3) -0.3403(3) 0.0591(7) Uani 1 1 d . . . . .
H24 H 0.500508 0.665147 -0.402942 0.071 Uiso 1 1 calc R . . . .
C25 C 0.4096(3) 0.6967(2) -0.2780(2) 0.0493(6) Uani 1 1 d . . . . .
H25 H 0.397660 0.771746 -0.298315 0.059 Uiso 1 1 calc 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 N1 1.6047(19) . ?
S1 N2 1.6070(18) . ?
O1 C10 1.356(3) . ?
O1 C13 1.414(3) . ?
N1 C1 1.348(2) . ?
N2 C6 1.340(2) . ?
N3 C5 1.413(2) . ?
N3 C14 1.401(3) . ?
N3 C20 1.431(2) . ?
C1 C2 1.435(3) . ?
C1 C6 1.433(3) . ?
C2 C3 1.367(3) . ?
C2 C7 1.473(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.404(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.355(3) . ?
C5 C6 1.420(3) . ?
C7 C8 1.388(3) . ?
C7 C12 1.388(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.369(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.374(3) . ?
C10 C11 1.374(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(3) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.383(3) . ?
C14 C19 1.385(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.375(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.369(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.361(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.377(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.364(3) . ?
C20 C25 1.368(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.379(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.365(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.358(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.378(3) . ?
C25 H25 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
N1 S1 N2 100.79(9) . . ?
C10 O1 C13 118.45(19) . . ?
C1 N1 S1 107.30(15) . . ?
C6 N2 S1 106.32(14) . . ?
C5 N3 C20 116.29(16) . . ?
C14 N3 C5 121.63(15) . . ?
C14 N3 C20 122.00(16) . . ?
N1 C1 C2 127.05(19) . . ?
N1 C1 C6 111.74(18) . . ?
C6 C1 C2 121.19(17) . . ?
C1 C2 C7 124.00(17) . . ?
C3 C2 C1 114.42(18) . . ?
C3 C2 C7 121.57(18) . . ?
C2 C3 H3 117.8 . . ?
C2 C3 C4 124.4(2) . . ?
C4 C3 H3 117.8 . . ?
C3 C4 H4 118.6 . . ?
C5 C4 C3 122.79(19) . . ?
C5 C4 H4 118.6 . . ?
N3 C5 C6 122.13(18) . . ?
C4 C5 N3 121.66(18) . . ?
C4 C5 C6 116.13(19) . . ?
N2 C6 C1 113.85(17) . . ?
N2 C6 C5 125.04(19) . . ?
C5 C6 C1 121.08(18) . . ?
C8 C7 C2 123.48(19) . . ?
C8 C7 C12 116.0(2) . . ?
C12 C7 C2 120.50(18) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 C7 121.8(2) . . ?
C9 C8 H8 119.1 . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 120.93(19) . . ?
C10 C9 H9 119.5 . . ?
O1 C10 C9 115.83(19) . . ?
O1 C10 C11 125.4(2) . . ?
C11 C10 C9 118.8(2) . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.9(2) . . ?
C12 C11 H11 120.1 . . ?
C7 C12 H12 118.7 . . ?
C11 C12 C7 122.6(2) . . ?
C11 C12 H12 118.7 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N3 121.16(17) . . ?
C15 C14 C19 118.26(19) . . ?
C19 C14 N3 120.58(19) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.1(2) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 120.7 . . ?
C18 C17 C16 118.7(2) . . ?
C18 C17 H17 120.7 . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C19 121.4(2) . . ?
C19 C18 H18 119.3 . . ?
C14 C19 H19 119.9 . . ?
C18 C19 C14 120.2(2) . . ?
C18 C19 H19 119.9 . . ?
C21 C20 N3 119.15(18) . . ?
C21 C20 C25 119.24(18) . . ?
C25 C20 N3 121.61(18) . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.5(2) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.0(2) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 120.3 . . ?
C24 C23 C22 119.5(2) . . ?
C24 C23 H23 120.3 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.7(2) . . ?
C25 C24 H24 119.7 . . ?
C20 C25 C24 120.1(2) . . ?
C20 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?

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
S1 N1 C1 C2 -179.17(16) . . . . ?
S1 N1 C1 C6 -0.97(19) . . . . ?
S1 N2 C6 C1 -0.1(2) . . . . ?
S1 N2 C6 C5 177.81(15) . . . . ?
O1 C10 C11 C12 177.5(2) . . . . ?
N1 S1 N2 C6 -0.41(15) . . . . ?
N1 C1 C2 C3 177.71(18) . . . . ?
N1 C1 C2 C7 -1.4(3) . . . . ?
N1 C1 C6 N2 0.7(2) . . . . ?
N1 C1 C6 C5 -177.28(16) . . . . ?
N2 S1 N1 C1 0.83(15) . . . . ?
N3 C5 C6 N2 -1.9(3) . . . . ?
N3 C5 C6 C1 175.89(17) . . . . ?
N3 C14 C15 C16 -177.5(2) . . . . ?
N3 C14 C19 C18 177.90(18) . . . . ?
N3 C20 C21 C22 -179.8(2) . . . . ?
N3 C20 C25 C24 -179.9(2) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C1 C2 C7 C8 -15.8(3) . . . . ?
C1 C2 C7 C12 164.66(19) . . . . ?
C2 C1 C6 N2 179.06(16) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C2 C7 C8 C9 -179.79(18) . . . . ?
C2 C7 C12 C11 179.4(2) . . . . ?
C3 C2 C7 C8 165.17(19) . . . . ?
C3 C2 C7 C12 -14.3(3) . . . . ?
C3 C4 C5 N3 -176.76(18) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 N2 -178.61(19) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C5 N3 C14 C15 -171.74(19) . . . . ?
C5 N3 C14 C19 8.8(3) . . . . ?
C5 N3 C20 C21 60.0(3) . . . . ?
C5 N3 C20 C25 -119.6(2) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C6 C1 C2 C7 -179.41(17) . . . . ?
C7 C2 C3 C4 178.56(19) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C7 C12 C11 -0.2(3) . . . . ?
C8 C9 C10 O1 -178.12(18) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 C7 0.5(4) . . . . ?
C12 C7 C8 C9 -0.3(3) . . . . ?
C13 O1 C10 C9 -175.5(2) . . . . ?
C13 O1 C10 C11 6.6(4) . . . . ?
C14 N3 C5 C4 -115.6(2) . . . . ?
C14 N3 C5 C6 67.8(2) . . . . ?
C14 N3 C20 C21 -123.3(2) . . . . ?
C14 N3 C20 C25 57.1(3) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C15 C14 C19 C18 -1.6(3) . . . . ?
C15 C16 C17 C18 -0.9(4) . . . . ?
C16 C17 C18 C19 1.3(4) . . . . ?
C17 C18 C19 C14 0.0(3) . . . . ?
C19 C14 C15 C16 2.0(3) . . . . ?
C20 N3 C5 C4 61.1(3) . . . . ?
C20 N3 C5 C6 -115.4(2) . . . . ?
C20 N3 C14 C15 11.7(3) . . . . ?
C20 N3 C14 C19 -167.80(18) . . . . ?
C20 C21 C22 C23 -0.1(4) . . . . ?
C21 C20 C25 C24 0.5(3) . . . . ?
C21 C22 C23 C24 0.2(4) . . . . ?
C22 C23 C24 C25 0.1(4) . . . . ?
C23 C24 C25 C20 -0.4(4) . . . . ?
C25 C20 C21 C22 -0.2(3) . . . . ?

_shelx_SHELXL_version_number     2016/6
_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_170614_pzx_3_8463_pl
_database_code_depnum_ccdc_archive 'CCDC 1813988'
_audit_update_record             
;
2017-12-29 deposited with the CCDC.
2018-07-02 downloaded from the CCDC.
;
_audit_creation_date             2017-06-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 N3 O2 S'
_chemical_formula_sum            'C20 H17 N3 O2 S'
_chemical_formula_weight         363.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 s1'
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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.0345(12)
_cell_length_b                   7.1821(6)
_cell_length_c                   31.643(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.706(9)
_cell_angle_gamma                90
_cell_volume                     3409.6(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2842
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3274
_cell_measurement_theta_min      3.1383
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.906
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            20924
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.145
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -80.00   15.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -38.0000 -120.0000 95

#__ type_ start__ end____ width___ exp.time_
  2 omega  -38.00   59.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   38.0000   60.0000 97

#__ type_ start__ end____ width___ exp.time_
  3 omega  -22.00   72.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000 -180.0000 94
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0464089000
_diffrn_orient_matrix_UB_12      0.0184894000
_diffrn_orient_matrix_UB_13      0.0023327000
_diffrn_orient_matrix_UB_21      -0.0042285000
_diffrn_orient_matrix_UB_22      0.0260164000
_diffrn_orient_matrix_UB_23      0.0213916000
_diffrn_orient_matrix_UB_31      0.0080337000
_diffrn_orient_matrix_UB_32      -0.0934626000
_diffrn_orient_matrix_UB_33      0.0064276000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3641
_reflns_number_total             6223
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    ?
_refine_diff_density_max         1.189
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         6223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1532
_refine_ls_R_factor_gt           0.1028
_refine_ls_restrained_S_all      1.040
_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)+(0.1462P)²+4.8527P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2657
_refine_ls_wR_factor_ref         0.3098
_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:
 N3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C15(H15),
 C16(H16), C18(H18), C19(H19), N6(H6), C24(H24), C25(H25), C28(H28), C29(H29),
 C31(H31), C32(H32), C35(H35), C36(H36), C38(H38), C39(H39)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C20(H20A,H20B,H20C), C33(H33A,H33B,H33C), C40(H40A,H40B,
 H40C)
;
_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 1.10156(9) 0.7674(3) 0.05471(5) 0.0708(5) Uani 1 1 d . . . . .
O1 O 0.6036(3) 0.8452(7) -0.15931(12) 0.0760(13) Uani 1 1 d . . . . .
O2 O 0.8996(2) 0.7168(6) 0.28613(12) 0.0615(10) Uani 1 1 d . . . . .
N1 N 1.0454(3) 0.7481(7) 0.09586(15) 0.0624(13) Uani 1 1 d . . . . .
N2 N 1.0222(3) 0.7590(7) 0.01717(15) 0.0594(13) Uani 1 1 d . . . . .
N3 N 0.8617(3) 0.7363(7) -0.02808(15) 0.0655(14) Uani 1 1 d . . . . .
H3 H 0.913820 0.721558 -0.037245 0.079 Uiso 1 1 calc R . . . .
C1 C 0.9585(3) 0.7348(7) 0.08198(17) 0.0452(12) Uani 1 1 d . . . . .
C2 C 0.9465(3) 0.7400(7) 0.03758(17) 0.0449(12) Uani 1 1 d . . . . .
C3 C 0.8607(3) 0.7326(7) 0.01530(17) 0.0493(13) Uani 1 1 d . . . . .
C4 C 0.7909(3) 0.7155(8) 0.04025(18) 0.0539(14) Uani 1 1 d . . . . .
H4 H 0.733729 0.706016 0.027396 0.065 Uiso 1 1 calc R . . . .
C5 C 0.8017(3) 0.7113(7) 0.08480(17) 0.0474(12) Uani 1 1 d . . . . .
H5 H 0.750709 0.704558 0.099861 0.057 Uiso 1 1 calc R . . . .
C6 C 0.8836(3) 0.7168(7) 0.10760(16) 0.0454(12) Uani 1 1 d . . . . .
C7 C 0.7941(4) 0.7593(8) -0.06029(17) 0.0536(14) Uani 1 1 d . . . . .
C8 C 0.8098(4) 0.6988(8) -0.10024(17) 0.0579(15) Uani 1 1 d . . . . .
H8 H 0.862820 0.636791 -0.104415 0.070 Uiso 1 1 calc R . . . .
C9 C 0.7497(4) 0.7268(9) -0.13437(18) 0.0632(16) Uani 1 1 d . . . . .
H9 H 0.763317 0.689187 -0.161326 0.076 Uiso 1 1 calc R . . . .
C10 C 0.6693(4) 0.8112(8) -0.12814(17) 0.0541(13) Uani 1 1 d . . . . .
C11 C 0.6518(3) 0.8707(8) -0.08741(16) 0.0545(14) Uani 1 1 d . . . . .
H11 H 0.597990 0.929833 -0.083351 0.065 Uiso 1 1 calc R . . . .
C12 C 0.7121(3) 0.8446(8) -0.05290(18) 0.0567(14) Uani 1 1 d . . . . .
H12 H 0.698936 0.882002 -0.025869 0.068 Uiso 1 1 calc R . . . .
C13 C 0.6246(5) 0.8044(12) -0.2013(2) 0.090(2) Uani 1 1 d . . . . .
H13A H 0.577851 0.849684 -0.220787 0.135 Uiso 1 1 calc GR . . . .
H13B H 0.630314 0.672117 -0.204636 0.135 Uiso 1 1 calc GR . . . .
H13C H 0.679722 0.863648 -0.207100 0.135 Uiso 1 1 calc GR . . . .
C14 C 0.8907(3) 0.7151(7) 0.15430(16) 0.0461(12) Uani 1 1 d . . . . .
C15 C 0.8283(3) 0.8050(7) 0.17795(17) 0.0517(13) Uani 1 1 d . . . . .
H15 H 0.782098 0.869541 0.163545 0.062 Uiso 1 1 calc R . . . .
C16 C 0.8317(3) 0.8031(7) 0.22075(17) 0.0510(13) Uani 1 1 d . . . . .
H16 H 0.788129 0.863445 0.235192 0.061 Uiso 1 1 calc R . . . .
C17 C 0.9006(3) 0.7108(7) 0.24279(16) 0.0461(12) Uani 1 1 d . . . . .
C18 C 0.9661(3) 0.6220(8) 0.22104(17) 0.0550(14) Uani 1 1 d . . . . .
H18 H 1.013314 0.561298 0.235629 0.066 Uiso 1 1 calc R . . . .
C19 C 0.9594(3) 0.6259(7) 0.17731(16) 0.0488(12) Uani 1 1 d . . . . .
H19 H 1.002884 0.565973 0.162736 0.059 Uiso 1 1 calc R . . . .
C20 C 0.9704(4) 0.6266(10) 0.31039(19) 0.0723(17) Uani 1 1 d . . . . .
H20A H 0.970776 0.496565 0.303386 0.108 Uiso 1 1 calc GR . . . .
H20B H 0.961767 0.641000 0.340008 0.108 Uiso 1 1 calc GR . . . .
H20C H 1.026211 0.681537 0.304090 0.108 Uiso 1 1 calc GR . . . .
S2 S 0.89896(9) 0.2122(2) 0.07357(5) 0.0603(5) Uani 1 1 d . . . . .
O3 O 0.4030(3) 0.2397(6) -0.13988(12) 0.0665(11) Uani 1 1 d . . . . .
O4 O 0.6985(3) 0.2038(7) 0.30659(12) 0.0727(12) Uani 1 1 d . . . . .
N4 N 0.8431(3) 0.2148(6) 0.11546(14) 0.0526(11) Uani 1 1 d . . . . .
N5 N 0.8204(3) 0.2424(6) 0.03673(14) 0.0561(12) Uani 1 1 d . . . . .
N6 N 0.6607(3) 0.3145(7) -0.00693(14) 0.0640(13) Uani 1 1 d . . . . .
H6 H 0.712388 0.340205 -0.015507 0.077 Uiso 1 1 calc R . . . .
C21 C 0.7572(3) 0.2408(6) 0.10180(16) 0.0415(11) Uani 1 1 d . . . . .
C22 C 0.7456(3) 0.2563(7) 0.05728(17) 0.0451(12) Uani 1 1 d . . . . .
C23 C 0.6592(3) 0.2907(7) 0.03563(16) 0.0480(12) Uani 1 1 d . . . . .
C24 C 0.5891(3) 0.3039(7) 0.06152(16) 0.0467(12) Uani 1 1 d . . . . .
H24 H 0.532099 0.328461 0.049622 0.056 Uiso 1 1 calc R . . . .
C25 C 0.6023(3) 0.2807(7) 0.10559(17) 0.0500(13) Uani 1 1 d . . . . .
H25 H 0.551864 0.284521 0.121085 0.060 Uiso 1 1 calc R . . . .
C26 C 0.6819(3) 0.2533(7) 0.12779(16) 0.0465(12) Uani 1 1 d . . . . .
C27 C 0.5916(3) 0.3044(8) -0.03978(16) 0.0503(13) Uani 1 1 d . . . . .
C28 C 0.6093(3) 0.3664(7) -0.07897(16) 0.0495(13) Uani 1 1 d . . . . .
H28 H 0.663816 0.423379 -0.082672 0.059 Uiso 1 1 calc R . . . .
C29 C 0.5492(4) 0.3473(8) -0.11322(17) 0.0561(14) Uani 1 1 d . . . . .
H29 H 0.563391 0.390063 -0.139697 0.067 Uiso 1 1 calc R . . . .
C30 C 0.4676(3) 0.2643(7) -0.10825(17) 0.0501(13) Uani 1 1 d . . . . .
C31 C 0.4494(3) 0.2014(8) -0.06868(17) 0.0521(13) Uani 1 1 d . . . . .
H31 H 0.394439 0.146050 -0.065091 0.063 Uiso 1 1 calc R . . . .
C32 C 0.5095(4) 0.2176(7) -0.03422(16) 0.0509(13) Uani 1 1 d . . . . .
H32 H 0.496082 0.172010 -0.007864 0.061 Uiso 1 1 calc R . . . .
C33 C 0.4217(4) 0.3038(10) -0.18095(19) 0.0768(19) Uani 1 1 d . . . . .
H33A H 0.369742 0.288308 -0.199917 0.115 Uiso 1 1 calc GR . . . .
H33B H 0.470121 0.233174 -0.191114 0.115 Uiso 1 1 calc GR . . . .
H33C H 0.437712 0.433128 -0.179515 0.115 Uiso 1 1 calc GR . . . .
C34 C 0.6902(3) 0.2387(7) 0.17487(17) 0.0473(12) Uani 1 1 d . . . . .
C35 C 0.6215(4) 0.1626(8) 0.19691(17) 0.0561(14) Uani 1 1 d . . . . .
H35 H 0.571184 0.116524 0.181782 0.067 Uiso 1 1 calc R . . . .
C36 C 0.6262(3) 0.1538(8) 0.24002(17) 0.0570(14) Uani 1 1 d . . . . .
H36 H 0.579150 0.102195 0.253735 0.068 Uiso 1 1 calc R . . . .
C37 C 0.7001(4) 0.2209(8) 0.26366(17) 0.0553(14) Uani 1 1 d . . . . .
C38 C 0.7697(4) 0.2969(8) 0.24243(18) 0.0591(14) Uani 1 1 d . . . . .
H38 H 0.820273 0.341980 0.257562 0.071 Uiso 1 1 calc R . . . .
C39 C 0.7632(3) 0.3050(8) 0.19889(17) 0.0539(13) Uani 1 1 d . . . . .
H39 H 0.809982 0.357352 0.185105 0.065 Uiso 1 1 calc R . . . .
C40 C 0.7762(5) 0.2609(11) 0.3316(2) 0.084(2) Uani 1 1 d . . . . .
H40A H 0.824565 0.177896 0.326761 0.125 Uiso 1 1 calc GR . . . .
H40B H 0.764241 0.258116 0.361031 0.125 Uiso 1 1 calc GR . . . .
H40C H 0.792121 0.385209 0.323840 0.125 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 N1 1.603(5) . ?
S1 N2 1.629(5) . ?
O1 C10 1.371(6) . ?
O1 C13 1.418(7) . ?
O2 C17 1.373(6) . ?
O2 C20 1.427(7) . ?
N1 C1 1.355(6) . ?
N2 C2 1.351(6) . ?
N3 H3 0.8600 . ?
N3 C3 1.374(7) . ?
N3 C7 1.402(7) . ?
C1 C2 1.405(7) . ?
C1 C6 1.435(7) . ?
C2 C3 1.431(7) . ?
C3 C4 1.358(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.409(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(7) . ?
C6 C14 1.475(7) . ?
C7 C8 1.371(7) . ?
C7 C12 1.409(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.377(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(8) . ?
C10 C11 1.399(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(7) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.395(7) . ?
C14 C19 1.382(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.352(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.380(7) . ?
C17 C18 1.392(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(7) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
S2 N4 1.615(5) . ?
S2 N5 1.620(5) . ?
O3 C30 1.360(6) . ?
O3 C33 1.424(7) . ?
O4 C37 1.366(6) . ?
O4 C40 1.428(7) . ?
N4 C21 1.347(6) . ?
N5 C22 1.339(6) . ?
N6 H6 0.8600 . ?
N6 C23 1.359(6) . ?
N6 C27 1.422(7) . ?
C21 C22 1.413(7) . ?
C21 C26 1.444(6) . ?
C22 C23 1.449(7) . ?
C23 C24 1.380(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.406(7) . ?
C25 H25 0.9300 . ?
C25 C26 1.362(7) . ?
C26 C34 1.491(7) . ?
C27 C28 1.360(7) . ?
C27 C32 1.405(7) . ?
C28 H28 0.9300 . ?
C28 C29 1.372(7) . ?
C29 H29 0.9300 . ?
C29 C30 1.383(7) . ?
C30 C31 1.375(7) . ?
C31 H31 0.9300 . ?
C31 C32 1.376(7) . ?
C32 H32 0.9300 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 C35 1.394(7) . ?
C34 C39 1.380(7) . ?
C35 H35 0.9300 . ?
C35 C36 1.363(7) . ?
C36 H36 0.9300 . ?
C36 C37 1.385(7) . ?
C37 C38 1.391(7) . ?
C38 H38 0.9300 . ?
C38 C39 1.376(7) . ?
C39 H39 0.9300 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 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
N1 S1 N2 101.0(2) . . ?
C10 O1 C13 116.4(4) . . ?
C17 O2 C20 117.8(4) . . ?
C1 N1 S1 106.9(4) . . ?
C2 N2 S1 104.7(4) . . ?
C3 N3 H3 113.8 . . ?
C3 N3 C7 132.4(5) . . ?
C7 N3 H3 113.8 . . ?
N1 C1 C2 112.4(4) . . ?
N1 C1 C6 126.8(5) . . ?
C2 C1 C6 120.9(4) . . ?
N2 C2 C1 115.0(4) . . ?
N2 C2 C3 121.9(5) . . ?
C1 C2 C3 123.0(4) . . ?
N3 C3 C2 115.1(4) . . ?
C4 C3 N3 129.9(5) . . ?
C4 C3 C2 115.0(5) . . ?
C3 C4 H4 118.6 . . ?
C3 C4 C5 122.7(5) . . ?
C5 C4 H4 118.6 . . ?
C4 C5 H5 118.0 . . ?
C6 C5 C4 124.1(5) . . ?
C6 C5 H5 118.0 . . ?
C1 C6 C14 124.0(4) . . ?
C5 C6 C1 114.3(5) . . ?
C5 C6 C14 121.7(4) . . ?
N3 C7 C12 122.1(5) . . ?
C8 C7 N3 118.2(5) . . ?
C8 C7 C12 119.7(5) . . ?
C7 C8 H8 118.9 . . ?
C7 C8 C9 122.2(5) . . ?
C9 C8 H8 118.9 . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.3(5) . . ?
C10 C9 H9 120.4 . . ?
O1 C10 C9 125.0(5) . . ?
O1 C10 C11 116.0(5) . . ?
C9 C10 C11 119.0(5) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 C10 122.2(5) . . ?
C12 C11 H11 118.9 . . ?
C7 C12 H12 121.2 . . ?
C11 C12 C7 117.5(5) . . ?
C11 C12 H12 121.2 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C6 121.8(5) . . ?
C19 C14 C6 122.3(4) . . ?
C19 C14 C15 115.9(5) . . ?
C14 C15 H15 118.3 . . ?
C16 C15 C14 123.3(5) . . ?
C16 C15 H15 118.3 . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.3(5) . . ?
C17 C16 H16 120.3 . . ?
O2 C17 C16 115.7(4) . . ?
O2 C17 C18 124.2(5) . . ?
C16 C17 C18 120.1(5) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 C17 118.5(5) . . ?
C19 C18 H18 120.7 . . ?
C14 C19 H19 118.6 . . ?
C18 C19 C14 122.8(5) . . ?
C18 C19 H19 118.6 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N4 S2 N5 101.2(2) . . ?
C30 O3 C33 117.2(4) . . ?
C37 O4 C40 117.4(5) . . ?
C21 N4 S2 106.1(4) . . ?
C22 N5 S2 104.9(4) . . ?
C23 N6 H6 114.3 . . ?
C23 N6 C27 131.3(4) . . ?
C27 N6 H6 114.3 . . ?
N4 C21 C22 112.6(4) . . ?
N4 C21 C26 126.6(5) . . ?
C22 C21 C26 120.8(4) . . ?
N5 C22 C21 115.1(4) . . ?
N5 C22 C23 122.6(5) . . ?
C21 C22 C23 122.3(4) . . ?
N6 C23 C22 114.8(4) . . ?
N6 C23 C24 129.9(5) . . ?
C24 C23 C22 115.3(5) . . ?
C23 C24 H24 119.5 . . ?
C23 C24 C25 121.1(5) . . ?
C25 C24 H24 119.5 . . ?
C24 C25 H25 116.8 . . ?
C26 C25 C24 126.3(5) . . ?
C26 C25 H25 116.8 . . ?
C21 C26 C34 123.1(5) . . ?
C25 C26 C21 114.2(5) . . ?
C25 C26 C34 122.7(4) . . ?
C28 C27 N6 118.2(4) . . ?
C28 C27 C32 119.0(5) . . ?
C32 C27 N6 122.5(5) . . ?
C27 C28 H28 119.0 . . ?
C27 C28 C29 122.0(5) . . ?
C29 C28 H28 119.0 . . ?
C28 C29 H29 120.1 . . ?
C28 C29 C30 119.8(5) . . ?
C30 C29 H29 120.1 . . ?
O3 C30 C29 124.7(5) . . ?
O3 C30 C31 116.9(5) . . ?
C31 C30 C29 118.4(5) . . ?
C30 C31 H31 118.8 . . ?
C30 C31 C32 122.3(5) . . ?
C32 C31 H31 118.8 . . ?
C27 C32 H32 120.8 . . ?
C31 C32 C27 118.4(5) . . ?
C31 C32 H32 120.8 . . ?
O3 C33 H33A 109.5 . . ?
O3 C33 H33B 109.5 . . ?
O3 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C35 C34 C26 120.7(5) . . ?
C39 C34 C26 122.6(4) . . ?
C39 C34 C35 116.7(5) . . ?
C34 C35 H35 119.1 . . ?
C36 C35 C34 121.8(5) . . ?
C36 C35 H35 119.1 . . ?
C35 C36 H36 119.6 . . ?
C35 C36 C37 120.8(5) . . ?
C37 C36 H36 119.6 . . ?
O4 C37 C36 116.2(5) . . ?
O4 C37 C38 125.2(5) . . ?
C36 C37 C38 118.6(5) . . ?
C37 C38 H38 120.2 . . ?
C39 C38 C37 119.6(5) . . ?
C39 C38 H38 120.2 . . ?
C34 C39 H39 118.7 . . ?
C38 C39 C34 122.6(5) . . ?
C38 C39 H39 118.7 . . ?
O4 C40 H40A 109.5 . . ?
O4 C40 H40B 109.5 . . ?
O4 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C1 C2 0.7(5) . . . . ?
S1 N1 C1 C6 -179.5(4) . . . . ?
S1 N2 C2 C1 0.4(5) . . . . ?
S1 N2 C2 C3 178.2(4) . . . . ?
O1 C10 C11 C12 179.7(5) . . . . ?
O2 C17 C18 C19 180.0(5) . . . . ?
N1 S1 N2 C2 0.0(4) . . . . ?
N1 C1 C2 N2 -0.7(6) . . . . ?
N1 C1 C2 C3 -178.5(5) . . . . ?
N1 C1 C6 C5 178.3(5) . . . . ?
N1 C1 C6 C14 1.8(8) . . . . ?
N2 S1 N1 C1 -0.4(4) . . . . ?
N2 C2 C3 N3 3.4(7) . . . . ?
N2 C2 C3 C4 -179.2(5) . . . . ?
N3 C3 C4 C5 179.0(5) . . . . ?
N3 C7 C8 C9 -175.6(5) . . . . ?
N3 C7 C12 C11 176.2(5) . . . . ?
C1 C2 C3 N3 -179.0(5) . . . . ?
C1 C2 C3 C4 -1.6(7) . . . . ?
C1 C6 C14 C15 140.7(5) . . . . ?
C1 C6 C14 C19 -38.9(7) . . . . ?
C2 C1 C6 C5 -1.9(7) . . . . ?
C2 C1 C6 C14 -178.4(5) . . . . ?
C2 C3 C4 C5 2.0(8) . . . . ?
C3 N3 C7 C8 -159.6(6) . . . . ?
C3 N3 C7 C12 21.5(9) . . . . ?
C3 C4 C5 C6 -2.7(8) . . . . ?
C4 C5 C6 C1 2.4(7) . . . . ?
C4 C5 C6 C14 179.0(5) . . . . ?
C5 C6 C14 C15 -35.5(7) . . . . ?
C5 C6 C14 C19 144.9(5) . . . . ?
C6 C1 C2 N2 179.4(5) . . . . ?
C6 C1 C2 C3 1.7(7) . . . . ?
C6 C14 C15 C16 178.6(5) . . . . ?
C6 C14 C19 C18 -179.3(5) . . . . ?
C7 N3 C3 C2 -169.0(6) . . . . ?
C7 N3 C3 C4 14.1(10) . . . . ?
C7 C8 C9 C10 -2.9(9) . . . . ?
C8 C7 C12 C11 -2.7(8) . . . . ?
C8 C9 C10 O1 -179.3(6) . . . . ?
C8 C9 C10 C11 1.7(9) . . . . ?
C9 C10 C11 C12 -1.3(9) . . . . ?
C10 C11 C12 C7 1.7(9) . . . . ?
C12 C7 C8 C9 3.4(9) . . . . ?
C13 O1 C10 C9 -5.8(9) . . . . ?
C13 O1 C10 C11 173.2(6) . . . . ?
C14 C15 C16 C17 1.0(8) . . . . ?
C15 C14 C19 C18 1.0(8) . . . . ?
C15 C16 C17 O2 179.4(5) . . . . ?
C15 C16 C17 C18 0.5(8) . . . . ?
C16 C17 C18 C19 -1.2(8) . . . . ?
C17 C18 C19 C14 0.4(8) . . . . ?
C19 C14 C15 C16 -1.8(8) . . . . ?
C20 O2 C17 C16 -178.8(5) . . . . ?
C20 O2 C17 C18 0.1(7) . . . . ?
S2 N4 C21 C22 0.0(5) . . . . ?
S2 N4 C21 C26 -179.8(4) . . . . ?
S2 N5 C22 C21 -0.2(5) . . . . ?
S2 N5 C22 C23 177.9(4) . . . . ?
O3 C30 C31 C32 179.7(5) . . . . ?
O4 C37 C38 C39 179.6(5) . . . . ?
N4 S2 N5 C22 0.2(4) . . . . ?
N4 C21 C22 N5 0.1(6) . . . . ?
N4 C21 C22 C23 -178.0(4) . . . . ?
N4 C21 C26 C25 179.7(5) . . . . ?
N4 C21 C26 C34 0.1(8) . . . . ?
N5 S2 N4 C21 -0.1(4) . . . . ?
N5 C22 C23 N6 -2.3(7) . . . . ?
N5 C22 C23 C24 -179.1(5) . . . . ?
N6 C23 C24 C25 -177.5(5) . . . . ?
N6 C27 C28 C29 174.4(5) . . . . ?
N6 C27 C32 C31 -174.9(5) . . . . ?
C21 C22 C23 N6 175.7(5) . . . . ?
C21 C22 C23 C24 -1.1(7) . . . . ?
C21 C26 C34 C35 -148.5(5) . . . . ?
C21 C26 C34 C39 34.1(7) . . . . ?
C22 C21 C26 C25 -0.1(7) . . . . ?
C22 C21 C26 C34 -179.8(4) . . . . ?
C22 C23 C24 C25 -1.3(7) . . . . ?
C23 N6 C27 C28 168.7(6) . . . . ?
C23 N6 C27 C32 -17.4(9) . . . . ?
C23 C24 C25 C26 3.4(8) . . . . ?
C24 C25 C26 C21 -2.5(8) . . . . ?
C24 C25 C26 C34 177.1(5) . . . . ?
C25 C26 C34 C35 31.8(7) . . . . ?
C25 C26 C34 C39 -145.6(5) . . . . ?
C26 C21 C22 N5 180.0(4) . . . . ?
C26 C21 C22 C23 1.9(7) . . . . ?
C26 C34 C35 C36 -177.6(5) . . . . ?
C26 C34 C39 C38 177.9(5) . . . . ?
C27 N6 C23 C22 162.1(5) . . . . ?
C27 N6 C23 C24 -21.7(10) . . . . ?
C27 C28 C29 C30 0.5(8) . . . . ?
C28 C27 C32 C31 -1.1(8) . . . . ?
C28 C29 C30 O3 179.5(5) . . . . ?
C28 C29 C30 C31 -0.5(8) . . . . ?
C29 C30 C31 C32 -0.3(8) . . . . ?
C30 C31 C32 C27 1.1(8) . . . . ?
C32 C27 C28 C29 0.3(8) . . . . ?
C33 O3 C30 C29 0.3(8) . . . . ?
C33 O3 C30 C31 -179.7(5) . . . . ?
C34 C35 C36 C37 0.0(9) . . . . ?
C35 C34 C39 C38 0.4(8) . . . . ?
C35 C36 C37 O4 -179.3(5) . . . . ?
C35 C36 C37 C38 -0.2(9) . . . . ?
C36 C37 C38 C39 0.5(8) . . . . ?
C37 C38 C39 C34 -0.6(9) . . . . ?
C39 C34 C35 C36 -0.1(8) . . . . ?
C40 O4 C37 C36 176.1(6) . . . . ?
C40 O4 C37 C38 -2.9(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
