# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_21dub_mz08_2
_database_code_depnum_ccdc_archive 'CCDC 2227014'
loop_
_audit_author_name
_audit_author_address
'Frank Hampel'
;Lehrstuhl fuer Organische Chemie I, FAU Erlangen Nuernberg
Germany
;
_audit_update_record             
;
2022-12-16 deposited with the CCDC.	2023-05-01 downloaded from the CCDC.
;
_audit_creation_date             2021-09-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
max.zitzmann@fau.de
frank.hampel@fau.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H24 N2 O S'
_chemical_formula_sum            'C25 H24 N2 O S'
_chemical_formula_weight         400.52
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H24 N2 O S'
_chemical_oxdiff_usercomment     MZ-198
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.9704(8)
_cell_length_b                   21.4506(10)
_cell_length_c                   9.7628(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.735(6)
_cell_angle_gamma                90
_cell_volume                     2051.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2121
_cell_measurement_temperature    152.95(10)
_cell_measurement_theta_max      68.5360
_cell_measurement_theta_min      4.4940
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.537
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.807
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 13 0 0.0250
2 -13 0 0.0250
0 -1 -6 0.1180
0 1 6 0.1180
-1 14 1 0.0306
1 -14 -1 0.0306
-6 -3 0 0.0230
6 3 0 0.0230

_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of MeOH and i-Hexane  by solvent layering'
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.046
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.6734 13.4558 0.0838 -0.1463 0.3567 -0.9227
1.6734 -13.4558 -0.0838 0.1463 -0.3567 0.9227
-0.1206 -1.1720 -6.1793 -0.3482 0.8369 0.4223
0.1206 1.1720 6.1793 0.3482 -0.8369 -0.4223
-0.8977 13.7347 0.7771 -0.2017 0.1889 -0.9611
0.8977 -13.7347 -0.7771 0.2017 -0.1889 0.9611
-6.1803 -3.2859 0.0195 0.8220 0.5660 0.0623
6.1803 3.2859 -0.0195 -0.8220 -0.5660 -0.0623

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6287
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.260
_diffrn_reflns_theta_min         4.514
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      152.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6144
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -38.00   1.00   15.27    --  -42.06 -38.00-120.00   76
  2  ω   -108.00 -18.00   1.00   15.27    --  -42.06 -38.00 -60.00   90
  3  ω     72.00 159.00   1.00   61.09    --   98.29  61.00-120.00   87
  4  ω    104.00 172.00   1.00   61.09    --   98.29 125.00  90.00   68
  5  ω     33.00 126.00   1.00   61.09    --   98.29 -61.00  90.00   93
  6  ω     31.00 119.00   1.00   61.09    --   98.29 -61.00 -30.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1189519000
_diffrn_orient_matrix_UB_12      -0.0260588000
_diffrn_orient_matrix_UB_13      0.0636203000
_diffrn_orient_matrix_UB_21      -0.0999534000
_diffrn_orient_matrix_UB_22      0.0149301000
_diffrn_orient_matrix_UB_23      -0.1363201000
_diffrn_orient_matrix_UB_31      0.0244007000
_diffrn_orient_matrix_UB_32      -0.0651852000
_diffrn_orient_matrix_UB_33      -0.0564462000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3060
_reflns_number_total             3658
_reflns_odcompleteness_completeness 98.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3658
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0677
_refine_ls_restrained_S_all      1.049
_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)+(0.0951P)²+2.2824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1780
_refine_ls_wR_factor_ref         0.1891
_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:
 C14(H14), C15(H15), C16(H16), C17(H17), C22(H22), C23(H23), C25(H25),
 C26(H26), C32(H32), C33(H33), C35(H35), C36(H36)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C38(H38A,H38B,H38C), C39(H39A,H39B,
 H39C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
S12 S 0.23202(9) 0.31002(4) 0.52178(9) 0.0438(3) Uani 1 1 d . . . . .
O19 O 0.2194(3) 0.14155(11) 0.3823(3) 0.0452(6) Uani 1 1 d . . . . .
N27 N 0.7190(3) 0.46998(13) 0.3367(3) 0.0443(7) Uani 1 1 d . . . . .
N37 N 0.7328(3) 0.02895(12) 0.3405(3) 0.0388(6) Uani 1 1 d . . . . .
C1 C 0.4253(3) 0.24762(13) 0.4019(3) 0.0291(6) Uani 1 1 d . . . . .
C11 C 0.3024(3) 0.24528(13) 0.4456(3) 0.0302(6) Uani 1 1 d . . . . .
C13 C 0.1009(3) 0.26486(15) 0.5654(3) 0.0347(7) Uani 1 1 d . . . . .
C14 C 0.0045(3) 0.28637(16) 0.6405(3) 0.0392(7) Uani 1 1 d . . . . .
H14 H 0.007220 0.327299 0.672351 0.047 Uiso 1 1 calc R U . . .
C15 C -0.0952(3) 0.24583(17) 0.6669(3) 0.0431(8) Uani 1 1 d . . . . .
H15 H -0.158406 0.259077 0.719722 0.052 Uiso 1 1 calc R U . . .
C16 C -0.1018(3) 0.18434(17) 0.6142(4) 0.0444(8) Uani 1 1 d . . . . .
H16 H -0.171031 0.157817 0.630209 0.053 Uiso 1 1 calc R U . . .
C17 C -0.0067(3) 0.16337(15) 0.5395(3) 0.0396(7) Uani 1 1 d . . . . .
H17 H -0.011264 0.122924 0.504605 0.048 Uiso 1 1 calc R U . . .
C18 C 0.0973(3) 0.20390(14) 0.5167(3) 0.0334(7) Uani 1 1 d . . . . .
C19 C 0.2116(3) 0.18687(15) 0.4416(3) 0.0325(7) Uani 1 1 d . . . . .
C21 C 0.4978(3) 0.30615(13) 0.3837(3) 0.0268(6) Uani 1 1 d . . . . .
C22 C 0.6423(3) 0.30718(13) 0.4051(3) 0.0336(7) Uani 1 1 d . . . . .
H22 H 0.690129 0.270347 0.429030 0.040 Uiso 1 1 calc R U . . .
C23 C 0.7128(3) 0.35994(15) 0.3920(3) 0.0354(7) Uani 1 1 d . . . . .
H23 H 0.807654 0.358522 0.408804 0.043 Uiso 1 1 calc R U . . .
C24 C 0.6474(3) 0.41636(14) 0.3542(3) 0.0335(7) Uani 1 1 d . . . . .
C25 C 0.5034(3) 0.41641(14) 0.3297(3) 0.0350(7) Uani 1 1 d . . . . .
H25 H 0.456528 0.453262 0.303403 0.042 Uiso 1 1 calc R U . . .
C26 C 0.4315(3) 0.36320(14) 0.3441(3) 0.0328(6) Uani 1 1 d . . . . .
H26 H 0.336667 0.364715 0.327273 0.039 Uiso 1 1 calc R U . . .
C28 C 0.8647(4) 0.46829(19) 0.3566(4) 0.0531(9) Uani 1 1 d . . . . .
H28A H 0.901414 0.456272 0.450862 0.080 Uiso 1 1 calc R U . . .
H28B H 0.898433 0.508842 0.338785 0.080 Uiso 1 1 calc R U . . .
H28C H 0.892196 0.438618 0.293562 0.080 Uiso 1 1 calc R U . . .
C29 C 0.6532(4) 0.52928(15) 0.3213(4) 0.0496(9) Uani 1 1 d . . . . .
H29A H 0.585883 0.529710 0.236971 0.074 Uiso 1 1 calc R U . . .
H29B H 0.719658 0.561242 0.316893 0.074 Uiso 1 1 calc R U . . .
H29C H 0.609670 0.536807 0.399521 0.074 Uiso 1 1 calc R U . . .
C31 C 0.4985(3) 0.18944(13) 0.3823(3) 0.0292(6) Uani 1 1 d . . . . .
C32 C 0.5224(3) 0.14415(13) 0.4862(3) 0.0309(6) Uani 1 1 d . . . . .
H32 H 0.484411 0.149185 0.565538 0.037 Uiso 1 1 calc R U . . .
C33 C 0.6009(3) 0.09200(13) 0.4750(3) 0.0311(6) Uani 1 1 d . . . . .
H33 H 0.615123 0.062868 0.546824 0.037 Uiso 1 1 calc R U . . .
C34 C 0.6594(3) 0.08244(13) 0.3567(3) 0.0300(6) Uani 1 1 d . . . . .
C35 C 0.6364(3) 0.12843(13) 0.2516(3) 0.0322(6) Uani 1 1 d . . . . .
H35 H 0.673785 0.123517 0.171845 0.039 Uiso 1 1 calc R U . . .
C36 C 0.5594(3) 0.18048(13) 0.2657(3) 0.0311(6) Uani 1 1 d . . . . .
H36 H 0.547440 0.210520 0.195745 0.037 Uiso 1 1 calc R U . . .
C38 C 0.7666(4) -0.01465(16) 0.4544(4) 0.0484(9) Uani 1 1 d . . . . .
H38A H 0.828936 0.004578 0.529254 0.073 Uiso 1 1 calc R U . . .
H38B H 0.808467 -0.050952 0.423004 0.073 Uiso 1 1 calc R U . . .
H38C H 0.684986 -0.026577 0.486492 0.073 Uiso 1 1 calc R U . . .
C39 C 0.8111(4) 0.02549(17) 0.2305(4) 0.0493(9) Uani 1 1 d . . . . .
H39A H 0.752345 0.032974 0.142412 0.074 Uiso 1 1 calc R U . . .
H39B H 0.851216 -0.015187 0.230106 0.074 Uiso 1 1 calc R U . . .
H39C H 0.882025 0.056387 0.245867 0.074 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S12 C11 1.780(3) . ?
S12 C13 1.742(3) . ?
O19 C19 1.141(4) . ?
N27 C24 1.381(4) . ?
N27 C28 1.430(5) . ?
N27 C29 1.427(5) . ?
N37 C34 1.386(4) . ?
N37 C38 1.443(4) . ?
N37 C39 1.443(4) . ?
C1 C11 1.371(4) . ?
C1 C21 1.476(4) . ?
C1 C31 1.476(4) . ?
C11 C19 1.542(4) . ?
C13 C14 1.392(4) . ?
C13 C18 1.390(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.413(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.402(4) . ?
C18 C19 1.510(4) . ?
C21 C22 1.417(4) . ?
C21 C26 1.410(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.351(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.392(5) . ?
C24 C25 1.410(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.369(4) . ?
C26 H26 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C31 C32 1.392(4) . ?
C31 C36 1.400(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.381(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.403(4) . ?
C34 C35 1.411(4) . ?
C35 H35 0.9300 . ?
C35 C36 1.376(4) . ?
C36 H36 0.9300 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 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
C13 S12 C11 92.33(14) . . ?
C24 N27 C28 119.9(3) . . ?
C24 N27 C29 121.1(3) . . ?
C29 N27 C28 118.2(3) . . ?
C34 N37 C38 120.1(3) . . ?
C34 N37 C39 119.9(3) . . ?
C39 N37 C38 117.3(3) . . ?
C11 C1 C21 123.7(2) . . ?
C11 C1 C31 120.1(3) . . ?
C21 C1 C31 116.0(2) . . ?
C1 C11 S12 123.1(2) . . ?
C1 C11 C19 125.2(3) . . ?
C19 C11 S12 111.6(2) . . ?
C14 C13 S12 124.6(3) . . ?
C18 C13 S12 114.3(2) . . ?
C18 C13 C14 121.1(3) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.8(3) . . ?
C15 C14 H14 120.6 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 119.0(3) . . ?
C18 C17 H17 120.5 . . ?
C13 C18 C17 120.1(3) . . ?
C13 C18 C19 114.8(3) . . ?
C17 C18 C19 125.0(3) . . ?
O19 C19 C11 127.6(3) . . ?
O19 C19 C18 125.5(3) . . ?
C18 C19 C11 106.5(2) . . ?
C22 C21 C1 120.2(2) . . ?
C26 C21 C1 123.8(3) . . ?
C26 C21 C22 116.0(3) . . ?
C21 C22 H22 118.9 . . ?
C23 C22 C21 122.1(3) . . ?
C23 C22 H22 118.9 . . ?
C22 C23 H23 119.1 . . ?
C22 C23 C24 121.8(3) . . ?
C24 C23 H23 119.1 . . ?
N27 C24 C23 122.0(3) . . ?
N27 C24 C25 120.8(3) . . ?
C23 C24 C25 117.2(3) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 C24 121.2(3) . . ?
C26 C25 H25 119.4 . . ?
C21 C26 H26 119.2 . . ?
C25 C26 C21 121.6(3) . . ?
C25 C26 H26 119.2 . . ?
N27 C28 H28A 109.5 . . ?
N27 C28 H28B 109.5 . . ?
N27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N27 C29 H29A 109.5 . . ?
N27 C29 H29B 109.5 . . ?
N27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C32 C31 C1 121.1(2) . . ?
C32 C31 C36 117.1(3) . . ?
C36 C31 C1 121.4(2) . . ?
C31 C32 H32 119.0 . . ?
C33 C32 C31 122.0(3) . . ?
C33 C32 H32 119.0 . . ?
C32 C33 H33 119.6 . . ?
C32 C33 C34 120.8(3) . . ?
C34 C33 H33 119.6 . . ?
N37 C34 C33 121.6(3) . . ?
N37 C34 C35 120.9(3) . . ?
C33 C34 C35 117.4(3) . . ?
C34 C35 H35 119.6 . . ?
C36 C35 C34 120.9(3) . . ?
C36 C35 H35 119.6 . . ?
C31 C36 H36 119.1 . . ?
C35 C36 C31 121.8(3) . . ?
C35 C36 H36 119.1 . . ?
N37 C38 H38A 109.5 . . ?
N37 C38 H38B 109.5 . . ?
N37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N37 C39 H39A 109.5 . . ?
N37 C39 H39B 109.5 . . ?
N37 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 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
S12 C11 C19 O19 168.1(3) . . . . ?
S12 C11 C19 C18 -4.8(3) . . . . ?
S12 C13 C14 C15 179.3(3) . . . . ?
S12 C13 C18 C17 -177.3(2) . . . . ?
S12 C13 C18 C19 3.0(3) . . . . ?
N27 C24 C25 C26 178.7(3) . . . . ?
N37 C34 C35 C36 177.7(3) . . . . ?
C1 C11 C19 O19 -14.5(5) . . . . ?
C1 C11 C19 C18 172.7(3) . . . . ?
C1 C21 C22 C23 -178.8(3) . . . . ?
C1 C21 C26 C25 179.4(3) . . . . ?
C1 C31 C32 C33 -174.2(3) . . . . ?
C1 C31 C36 C35 175.1(3) . . . . ?
C11 S12 C13 C14 175.9(3) . . . . ?
C11 S12 C13 C18 -5.1(3) . . . . ?
C11 C1 C21 C22 149.3(3) . . . . ?
C11 C1 C21 C26 -31.1(4) . . . . ?
C11 C1 C31 C32 -50.6(4) . . . . ?
C11 C1 C31 C36 136.4(3) . . . . ?
C13 S12 C11 C1 -171.9(3) . . . . ?
C13 S12 C11 C19 5.6(2) . . . . ?
C13 C14 C15 C16 -2.2(5) . . . . ?
C13 C18 C19 O19 -171.8(3) . . . . ?
C13 C18 C19 C11 1.2(3) . . . . ?
C14 C13 C18 C17 1.8(5) . . . . ?
C14 C13 C18 C19 -177.9(3) . . . . ?
C14 C15 C16 C17 2.0(5) . . . . ?
C15 C16 C17 C18 0.2(5) . . . . ?
C16 C17 C18 C13 -2.0(5) . . . . ?
C16 C17 C18 C19 177.6(3) . . . . ?
C17 C18 C19 O19 8.5(5) . . . . ?
C17 C18 C19 C11 -178.5(3) . . . . ?
C18 C13 C14 C15 0.4(5) . . . . ?
C21 C1 C11 S12 -14.1(4) . . . . ?
C21 C1 C11 C19 168.7(3) . . . . ?
C21 C1 C31 C32 124.3(3) . . . . ?
C21 C1 C31 C36 -48.7(4) . . . . ?
C21 C22 C23 C24 -1.2(4) . . . . ?
C22 C21 C26 C25 -1.0(4) . . . . ?
C22 C23 C24 N27 -178.0(3) . . . . ?
C22 C23 C24 C25 0.0(4) . . . . ?
C23 C24 C25 C26 0.6(4) . . . . ?
C24 C25 C26 C21 0.0(4) . . . . ?
C26 C21 C22 C23 1.6(4) . . . . ?
C28 N27 C24 C23 0.5(5) . . . . ?
C28 N27 C24 C25 -177.5(3) . . . . ?
C29 N27 C24 C23 -169.2(3) . . . . ?
C29 N27 C24 C25 12.8(5) . . . . ?
C31 C1 C11 S12 160.4(2) . . . . ?
C31 C1 C11 C19 -16.8(4) . . . . ?
C31 C1 C21 C22 -25.4(4) . . . . ?
C31 C1 C21 C26 154.1(3) . . . . ?
C31 C32 C33 C34 -0.4(5) . . . . ?
C32 C31 C36 C35 1.8(5) . . . . ?
C32 C33 C34 N37 -176.8(3) . . . . ?
C32 C33 C34 C35 0.9(4) . . . . ?
C33 C34 C35 C36 0.0(5) . . . . ?
C34 C35 C36 C31 -1.4(5) . . . . ?
C36 C31 C32 C33 -0.9(5) . . . . ?
C38 N37 C34 C33 -8.4(5) . . . . ?
C38 N37 C34 C35 174.0(3) . . . . ?
C39 N37 C34 C33 -169.1(3) . . . . ?
C39 N37 C34 C35 13.3(5) . . . . ?


_olex2_date_sample_data_collection 2021-09-07
_olex2_diffrn_ambient_temperature_device 'Cryojet - Oxford Instruments'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a mylar loop in perfluoroether oil'
_olex2_submission_original_sample_id MZ198
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.271
_oxdiff_exptl_absorpt_empirical_full_min 0.854
####################################################################### 
# 
# 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_21dub_mz09
_database_code_depnum_ccdc_archive 'CCDC 2227015'
loop_
_audit_author_name
_audit_author_address
'Frank Hampel'
;Lehrstuhl fuer Organische Chemie I, FAU Erlangen Nuernberg
Germany
;
_audit_update_record             
;
2022-12-16 deposited with the CCDC.	2023-05-01 downloaded from the CCDC.
;
_audit_creation_date             2021-11-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
max.zitzmann@fau.de
frank.hampel@fau.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H18 N2 O S'
_chemical_formula_sum            'C24 H18 N2 O S'
_chemical_formula_weight         382.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H18 N2 O S'
_chemical_oxdiff_usercomment     'M. Zitzmann; MZ193'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.7409(2)
_cell_length_b                   13.9118(3)
_cell_length_c                   15.9596(4)
_cell_angle_alpha                90
_cell_angle_beta                 89.742(2)
_cell_angle_gamma                90
_cell_volume                     1940.69(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4105
_cell_measurement_temperature    154(4)
_cell_measurement_theta_max      71.4900
_cell_measurement_theta_min      4.1960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.605
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.749
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -4 -9 0.0561
0 2 10 0.0246
4 7 -1 0.0903
-6 -1 1 0.0800
2 -8 1 0.1276
5 -3 -3 0.1423
5 5 -2 0.0871
1 9 0 0.0768
-5 0 3 0.0673
-2 -9 0 0.1078
2 -8 -2 0.1260
0 -6 8 0.0771
0 6 -8 0.0771
6 -1 1 0.1323

_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of CH2Cl2 and hexanes  by solvent layering'
_exptl_crystal_size_max          0.229
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.103
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0285 -3.5292 -9.3732 -0.8206 0.5026 -0.2719
0.0200 1.8874 10.1456 0.8530 -0.5218 0.0091
3.5721 6.8779 -1.4867 -0.0258 -0.0581 0.9980
-5.6331 -0.7198 0.8221 -0.2887 -0.6035 -0.7433
2.2514 -8.2433 0.9539 0.3928 0.8268 -0.4026
5.0849 -2.8831 -3.1488 0.1183 0.8984 0.4229
4.5255 5.1377 -1.9889 0.0273 0.1962 0.9802
1.0345 8.8667 0.3576 -0.0716 -0.5576 0.8270
-5.4159 0.0280 3.0324 -0.0952 -0.7186 -0.6889
-1.5455 -8.6808 -0.0521 0.0608 0.4755 -0.8776
2.2681 -8.0639 -2.1202 0.1213 0.9316 -0.3426
0.4994 -5.5230 8.1451 0.8532 0.1579 -0.4970
-0.4994 5.5230 -8.1451 -0.8532 -0.1579 0.4970
5.5774 -1.2415 1.2813 0.5071 0.6635 0.5501

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6519
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.634
_diffrn_reflns_theta_min         4.216
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      154(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6144
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00 -33.00   1.00    1.94    --  -42.69 -38.00-180.00   84
  2  ω     28.00  94.00   1.00    1.94    --   42.69-125.00-120.00   66
  3  ω     23.00  67.00   1.00    1.94    --   42.69-125.00 120.00   44
  4  ω    113.00 174.00   1.00    7.73    --  102.49  77.00  60.00   61
  5  ω    122.00 156.00   1.00    7.73    --  102.49 116.00  21.00   34
  6  ω     29.00 127.00   1.00    7.73    --  102.49 -45.00 -30.00   98
  7  ω     82.00 171.00   1.00    7.73    --  102.49  61.00 120.00   89
  8  ω     73.00 145.00   1.00    7.73    --  102.49  77.00-150.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0664969000
_diffrn_orient_matrix_UB_12      -0.0193633000
_diffrn_orient_matrix_UB_13      0.0875463000
_diffrn_orient_matrix_UB_21      0.1111142000
_diffrn_orient_matrix_UB_22      -0.0743299000
_diffrn_orient_matrix_UB_23      -0.0378268000
_diffrn_orient_matrix_UB_31      0.1196666000
_diffrn_orient_matrix_UB_32      0.0798796000
_diffrn_orient_matrix_UB_33      -0.0141970000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3397
_reflns_number_total             3641
_reflns_odcompleteness_completeness 99.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.870
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3641
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.025
_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)+(0.0746P)²+1.9948P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1445
_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:
 C14(H14), C15(H15), C16(H16), C17(H17), C22(H22), C23(H23), C25(H25),
 C26(H26), C32(H32), C33(H33), C35(H35), C36(H36)
2.b Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C39(H39A,H39B,H39C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
S12 S 0.34356(6) 0.45633(4) 0.71776(4) 0.03538(19) Uani 1 1 d . . . . .
O20 O 0.3393(2) 0.18311(15) 0.69831(12) 0.0440(4) Uani 1 1 d . . . . .
N28 N 0.9574(3) -0.09019(17) 0.60018(16) 0.0522(6) Uani 1 1 d . . . . .
N37 N 0.9386(2) 0.64638(14) 0.55032(12) 0.0332(4) Uani 1 1 d . . . . .
C1 C 0.5687(2) 0.33304(14) 0.65811(12) 0.0242(4) Uani 1 1 d . . . . .
C11 C 0.4262(2) 0.34247(15) 0.69072(13) 0.0262(4) Uani 1 1 d . . . . .
C13 C 0.1995(2) 0.39853(16) 0.77619(14) 0.0292(5) Uani 1 1 d . . . . .
C14 C 0.0936(3) 0.44684(16) 0.82593(15) 0.0345(5) Uani 1 1 d . . . . .
H14 H 0.096011 0.513398 0.831188 0.041 Uiso 1 1 calc R U . . .
C15 C -0.0148(3) 0.39276(18) 0.86708(15) 0.0364(5) Uani 1 1 d . . . . .
H15 H -0.084692 0.423328 0.902213 0.044 Uiso 1 1 calc R U . . .
C16 C -0.0228(3) 0.29312(18) 0.85749(15) 0.0351(5) Uani 1 1 d . . . . .
H16 H -0.099703 0.258709 0.884537 0.042 Uiso 1 1 calc R U . . .
C17 C 0.0824(3) 0.24544(16) 0.80829(15) 0.0320(5) Uani 1 1 d . . . . .
H17 H 0.077818 0.179044 0.801984 0.038 Uiso 1 1 calc R U . . .
C18 C 0.1958(2) 0.29888(16) 0.76819(13) 0.0282(5) Uani 1 1 d . . . . .
C19 C 0.3234(2) 0.2562(2) 0.71495(13) 0.0316(5) Uani 1 1 d . . . . .
C21 C 0.6432(2) 0.23692(14) 0.64755(13) 0.0243(4) Uani 1 1 d . . . . .
C22 C 0.6718(3) 0.20247(16) 0.56709(13) 0.0301(5) Uani 1 1 d . . . . .
H22 H 0.636062 0.236656 0.521081 0.036 Uiso 1 1 calc R U . . .
C23 C 0.7525(3) 0.11814(17) 0.55458(14) 0.0338(5) Uani 1 1 d . . . . .
H23 H 0.769529 0.094984 0.500673 0.041 Uiso 1 1 calc R U . . .
C24 C 0.8080(2) 0.06839(16) 0.62374(14) 0.0297(5) Uani 1 1 d . . . . .
C25 C 0.7790(2) 0.10142(16) 0.70482(14) 0.0305(5) Uani 1 1 d . . . . .
H25 H 0.815087 0.067406 0.750834 0.037 Uiso 1 1 calc R U . . .
C26 C 0.6961(3) 0.18512(15) 0.71621(13) 0.0289(5) Uani 1 1 d . . . . .
H26 H 0.675528 0.206978 0.770168 0.035 Uiso 1 1 calc R U . . .
C27 C 0.8931(3) -0.01968(18) 0.61111(16) 0.0379(5) Uani 1 1 d . . . . .
C31 C 0.6640(2) 0.41491(14) 0.63127(12) 0.0239(4) Uani 1 1 d . . . . .
C32 C 0.6024(2) 0.49273(15) 0.58744(12) 0.0257(4) Uani 1 1 d . . . . .
H32 H 0.497665 0.494472 0.577687 0.031 Uiso 1 1 calc R U . . .
C33 C 0.6928(2) 0.56717(15) 0.55818(13) 0.0269(4) Uani 1 1 d . . . . .
H33 H 0.648664 0.615961 0.526615 0.032 Uiso 1 1 calc R U . . .
C34 C 0.8506(2) 0.57028(15) 0.57541(12) 0.0260(4) Uani 1 1 d . . . . .
C35 C 0.9132(2) 0.49181(16) 0.61979(13) 0.0273(4) Uani 1 1 d . . . . .
H35 H 1.017136 0.491370 0.632097 0.033 Uiso 1 1 calc R U . . .
C36 C 0.8227(2) 0.41575(15) 0.64519(13) 0.0263(4) Uani 1 1 d . . . . .
H36 H 0.867869 0.363802 0.672161 0.032 Uiso 1 1 calc R U . . .
C38 C 0.8854(3) 0.71041(17) 0.48462(15) 0.0351(5) Uani 1 1 d . . . . .
H38A H 0.844235 0.673120 0.439403 0.053 Uiso 1 1 calc R U . . .
H38B H 0.969423 0.748423 0.464373 0.053 Uiso 1 1 calc R U . . .
H38C H 0.807335 0.751956 0.506709 0.053 Uiso 1 1 calc R U . . .
C39 C 1.0968(3) 0.65409(18) 0.57596(16) 0.0371(5) Uani 1 1 d . . . . .
H39A H 1.105935 0.635042 0.633538 0.056 Uiso 1 1 calc R U . . .
H39B H 1.130466 0.719408 0.569760 0.056 Uiso 1 1 calc R U . . .
H39C H 1.159028 0.612935 0.541582 0.056 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S12 C11 1.793(2) . ?
S12 C13 1.758(2) . ?
O20 C19 1.061(3) . ?
N28 C27 1.144(3) . ?
N37 C34 1.368(3) . ?
N37 C38 1.454(3) . ?
N37 C39 1.448(3) . ?
C1 C11 1.354(3) . ?
C1 C21 1.497(3) . ?
C1 C31 1.474(3) . ?
C11 C19 1.547(3) . ?
C13 C14 1.390(3) . ?
C13 C18 1.393(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.375(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.396(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.377(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.393(3) . ?
C18 C19 1.519(3) . ?
C21 C22 1.392(3) . ?
C21 C26 1.392(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.383(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.392(3) . ?
C24 C25 1.395(3) . ?
C24 C27 1.447(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.383(3) . ?
C26 H26 0.9300 . ?
C31 C32 1.398(3) . ?
C31 C36 1.406(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.382(3) . ?
C33 H33 0.9300 . ?
C33 C34 1.409(3) . ?
C34 C35 1.413(3) . ?
C35 H35 0.9300 . ?
C35 C36 1.381(3) . ?
C36 H36 0.9300 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 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
C13 S12 C11 90.59(10) . . ?
C34 N37 C38 120.26(19) . . ?
C34 N37 C39 120.75(19) . . ?
C39 N37 C38 117.88(18) . . ?
C11 C1 C21 121.95(18) . . ?
C11 C1 C31 123.69(19) . . ?
C31 C1 C21 114.36(17) . . ?
C1 C11 S12 123.15(16) . . ?
C1 C11 C19 123.6(2) . . ?
C19 C11 S12 113.09(16) . . ?
C14 C13 S12 123.73(17) . . ?
C14 C13 C18 121.2(2) . . ?
C18 C13 S12 115.05(17) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 C13 117.7(2) . . ?
C15 C14 H14 121.2 . . ?
C14 C15 H15 119.2 . . ?
C14 C15 C16 121.7(2) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.5(2) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.8 . . ?
C16 C17 C18 118.5(2) . . ?
C18 C17 H17 120.8 . . ?
C13 C18 C17 120.4(2) . . ?
C13 C18 C19 115.0(2) . . ?
C17 C18 C19 124.6(2) . . ?
O20 C19 C11 127.3(2) . . ?
O20 C19 C18 127.6(2) . . ?
C18 C19 C11 105.1(2) . . ?
C22 C21 C1 119.18(18) . . ?
C22 C21 C26 119.29(19) . . ?
C26 C21 C1 121.31(18) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 C21 120.9(2) . . ?
C23 C22 H22 119.5 . . ?
C22 C23 H23 120.4 . . ?
C22 C23 C24 119.1(2) . . ?
C24 C23 H23 120.4 . . ?
C23 C24 C25 120.6(2) . . ?
C23 C24 C27 119.4(2) . . ?
C25 C24 C27 119.9(2) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 C24 119.5(2) . . ?
C26 C25 H25 120.3 . . ?
C21 C26 H26 119.7 . . ?
C25 C26 C21 120.5(2) . . ?
C25 C26 H26 119.7 . . ?
N28 C27 C24 178.4(3) . . ?
C32 C31 C1 121.71(18) . . ?
C32 C31 C36 117.06(18) . . ?
C36 C31 C1 121.16(18) . . ?
C31 C32 H32 119.0 . . ?
C33 C32 C31 121.92(19) . . ?
C33 C32 H32 119.0 . . ?
C32 C33 H33 119.5 . . ?
C32 C33 C34 121.03(19) . . ?
C34 C33 H33 119.5 . . ?
N37 C34 C33 121.1(2) . . ?
N37 C34 C35 121.75(19) . . ?
C33 C34 C35 117.13(19) . . ?
C34 C35 H35 119.5 . . ?
C36 C35 C34 121.09(19) . . ?
C36 C35 H35 119.5 . . ?
C31 C36 H36 119.2 . . ?
C35 C36 C31 121.63(19) . . ?
C35 C36 H36 119.2 . . ?
N37 C38 H38A 109.5 . . ?
N37 C38 H38B 109.5 . . ?
N37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N37 C39 H39A 109.5 . . ?
N37 C39 H39B 109.5 . . ?
N37 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 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
S12 C11 C19 O20 170.9(2) . . . . ?
S12 C11 C19 C18 -9.55(19) . . . . ?
S12 C13 C14 C15 178.80(18) . . . . ?
S12 C13 C18 C17 -176.97(17) . . . . ?
S12 C13 C18 C19 3.9(2) . . . . ?
N37 C34 C35 C36 179.6(2) . . . . ?
C1 C11 C19 O20 -13.7(4) . . . . ?
C1 C11 C19 C18 165.85(19) . . . . ?
C1 C21 C22 C23 174.2(2) . . . . ?
C1 C21 C26 C25 -173.11(19) . . . . ?
C1 C31 C32 C33 -176.43(19) . . . . ?
C1 C31 C36 C35 179.56(19) . . . . ?
C11 S12 C13 C14 173.0(2) . . . . ?
C11 S12 C13 C18 -8.21(17) . . . . ?
C11 C1 C21 C22 113.1(2) . . . . ?
C11 C1 C21 C26 -72.4(3) . . . . ?
C11 C1 C31 C32 -41.5(3) . . . . ?
C11 C1 C31 C36 141.6(2) . . . . ?
C13 S12 C11 C1 -165.16(19) . . . . ?
C13 S12 C11 C19 10.26(15) . . . . ?
C13 C14 C15 C16 -2.2(3) . . . . ?
C13 C18 C19 O20 -176.8(2) . . . . ?
C13 C18 C19 C11 3.6(2) . . . . ?
C14 C13 C18 C17 1.8(3) . . . . ?
C14 C13 C18 C19 -177.29(19) . . . . ?
C14 C15 C16 C17 2.3(4) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C16 C17 C18 C13 -1.7(3) . . . . ?
C16 C17 C18 C19 177.4(2) . . . . ?
C17 C18 C19 O20 4.1(4) . . . . ?
C17 C18 C19 C11 -175.4(2) . . . . ?
C18 C13 C14 C15 0.1(3) . . . . ?
C21 C1 C11 S12 171.08(15) . . . . ?
C21 C1 C11 C19 -3.9(3) . . . . ?
C21 C1 C31 C32 139.2(2) . . . . ?
C21 C1 C31 C36 -37.6(3) . . . . ?
C21 C22 C23 C24 -1.2(3) . . . . ?
C22 C21 C26 C25 1.4(3) . . . . ?
C22 C23 C24 C25 1.9(3) . . . . ?
C22 C23 C24 C27 -179.8(2) . . . . ?
C23 C24 C25 C26 -0.9(3) . . . . ?
C24 C25 C26 C21 -0.7(3) . . . . ?
C26 C21 C22 C23 -0.4(3) . . . . ?
C27 C24 C25 C26 -179.3(2) . . . . ?
C31 C1 C11 S12 -8.1(3) . . . . ?
C31 C1 C11 C19 176.99(18) . . . . ?
C31 C1 C21 C22 -67.7(2) . . . . ?
C31 C1 C21 C26 106.8(2) . . . . ?
C31 C32 C33 C34 -3.5(3) . . . . ?
C32 C31 C36 C35 2.6(3) . . . . ?
C32 C33 C34 N37 -176.5(2) . . . . ?
C32 C33 C34 C35 3.3(3) . . . . ?
C33 C34 C35 C36 -0.2(3) . . . . ?
C34 C35 C36 C31 -2.8(3) . . . . ?
C36 C31 C32 C33 0.5(3) . . . . ?
C38 N37 C34 C33 -18.9(3) . . . . ?
C38 N37 C34 C35 161.3(2) . . . . ?
C39 N37 C34 C33 173.3(2) . . . . ?
C39 N37 C34 C35 -6.5(3) . . . . ?


_olex2_date_sample_data_collection 2021-11-11
_olex2_diffrn_ambient_temperature_device 'Cryojet - Oxford Instruments'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a mylar loop in perfluoroether oil'
_olex2_submission_original_sample_id MZ193
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.214
_oxdiff_exptl_absorpt_empirical_full_min 0.892
####################################################################### 
# 
# 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_21dub_mz07
_database_code_depnum_ccdc_archive 'CCDC 2227017'
loop_
_audit_author_name
_audit_author_address
'Frank Hampel'
;Lehrstuhl fuer Organische Chemie I, FAU Erlangen Nuernberg
Germany
;
_audit_update_record             
;
2022-12-16 deposited with the CCDC.	2023-05-01 downloaded from the CCDC.
;
_audit_creation_date             2021-08-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
max.zitzmann@fau.de
frank.hampel@fau.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 N2 O S'
_chemical_formula_sum            'C23 H20 N2 O S'
_chemical_formula_weight         372.47
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H20 N2 O S'
_chemical_oxdiff_usercomment     MZ-190
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   5.5494(8)
_cell_length_b                   12.9584(18)
_cell_length_c                   13.437(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.222(13)
_cell_angle_gamma                90
_cell_volume                     962.3(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2364
_cell_measurement_temperature    153.00(10)
_cell_measurement_theta_max      70.0320
_cell_measurement_theta_min      3.3910
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.601
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.718
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 2 -1 0.0937
0 -8 0 0.0521
-4 0 1 0.1259
0 8 0 0.0411
0 -3 -8 0.0524
0 3 8 0.0524
0 -6 6 0.0560
0 6 -6 0.0560
-3 -4 -3 0.0905
3 4 3 0.0905
-1 2 -8 0.0677
1 -2 8 0.0677

_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of DCM and i-Hexane  by solvent layering'
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.105
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.5255 1.7051 -1.1125 -0.0248 -0.0751 0.9969
0.2072 -8.3947 0.0512 -0.3246 -0.9177 -0.2291
-3.6018 0.3640 1.1076 0.1054 0.3031 -0.9471
0.4691 8.3288 -0.2593 0.3049 0.8610 0.4070
0.2734 -3.3380 -7.9737 0.7259 -0.6878 -0.0090
-0.2734 3.3380 7.9737 -0.7259 0.6878 0.0090
-0.4544 -6.4152 5.6505 -0.8200 -0.4453 -0.3597
0.4544 6.4152 -5.6505 0.8200 0.4453 0.3597
-2.6002 -4.2649 -3.4483 0.3709 -0.4357 -0.8201
2.6002 4.2649 3.4483 -0.3709 0.4357 0.8201
-0.8797 2.1304 -7.9511 0.9912 -0.0254 -0.1299
0.8797 -2.1304 7.9511 -0.9912 0.0254 0.1299

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6457
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.330
_diffrn_reflns_theta_min         3.303
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      153.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6144
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00  31.00   1.00    1.00    --  -42.06  57.00 -30.00   93
  2  ω      1.00  78.00   1.00    1.00    --   42.06 -99.00  60.00   77
  3  ω      9.00 117.00   1.00    1.00    --   42.06  77.00-180.00  108
  4  ω     22.00  79.00   1.00    1.00    --   42.06  57.00 120.00   57
  5  ω     81.00 168.00   1.00    1.54    --  101.31  45.00 -60.00   87
  6  ω     25.00 101.00   1.00    1.54    --  101.31 -94.00-120.00   76
  7  ω    113.00 170.00   1.00    1.54    --  101.31 125.00 -60.00   57
  8  ω     49.00 109.00   1.00    1.54    --  101.31 -94.00 -30.00   60
  9  ω     87.00 178.00   1.00    1.54    --  101.31  30.00   0.00   91
 10  ω     29.00 116.00   1.00    1.54    --  101.31-125.00-180.00   87
 11  ω     83.00 150.00   1.00    1.54    --  101.31  45.00  60.00   67
 12  ω    100.00 175.00   1.00    1.54    --  101.31 125.00-150.00   75
 13  ω     38.00  64.00   1.00    1.54    --  101.31 -45.00 -90.00   26
 14  ω     95.00 133.00   1.00    1.54    --  101.31 125.00-180.00   38
 15  ω     44.00 121.00   1.00    1.54    --  101.31 -30.00-180.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0588927000
_diffrn_orient_matrix_UB_12      0.0365509000
_diffrn_orient_matrix_UB_13      -0.1083526000
_diffrn_orient_matrix_UB_21      -0.0612731000
_diffrn_orient_matrix_UB_22      0.1080427000
_diffrn_orient_matrix_UB_23      0.0389263000
_diffrn_orient_matrix_UB_31      0.2651626000
_diffrn_orient_matrix_UB_32      0.0338136000
_diffrn_orient_matrix_UB_33      -0.0039347000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          
'Data set was refined as racemib twin in space group P2(1) with BASF = 0.14(7)'
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                2974
_reflns_number_total             3595
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.03
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.14(7)
_refine_ls_extinction_coef       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3595
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0816
_refine_ls_restrained_S_all      1.086
_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)+(0.1170P)²+0.7713P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2222
_refine_ls_wR_factor_ref         0.2346
_refine_special_details          
;
A disorder of the following atoms was refined to 63:37% occupation: S12/S12a, C19/C19a, O20/O20a, C17/C17a, N14/N14a.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.86(7)
 0.14(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Shared sites
{C17A, N14}
{C17, N14A}
4. Restrained distances
 N14A-C18 \\sim N14-C13
 with sigma of 0.02
 C32-C33 \\sim C16-C17
 with sigma of 0.02
5. Uiso/Uaniso restraints and constraints
Uanis(S12A) = Uanis(S12)
Uanis(O20A) = Uanis(O20)
Uanis(C17) = Uanis(N14A)
Uanis(C19A) = Uanis(C19)
Uanis(C17A) = Uanis(N14)
6. Others
 Sof(H15A)=Sof(H16A)=Sof(S12A)=Sof(O20A)=Sof(N14A)=Sof(C17A)=Sof(H17A)=
 Sof(C19A)=1-FVAR(1)
 Sof(H15)=Sof(H16)=Sof(S12)=Sof(O20)=Sof(N14)=Sof(C17)=Sof(H17)=Sof(C19)=FVAR(1)
7.a Aromatic/amide H refined with riding coordinates:
 C15(H15A), C15(H15), C16(H16A), C16(H16), C22(H22), C23(H23), C25(H25),
 C26(H26), C32(H32), C33(H33), C35(H35), C36(H36), C17A(H17A), C17(H17)
7.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C37(H37A,H37B,H37C)
;
_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
N27 N 1.1471(13) 0.4863(6) 0.4279(5) 0.0636(19) Uani 1 1 d . . . . .
C1 C 0.5105(12) 0.4452(5) 0.7353(5) 0.0422(15) Uani 1 1 d . . . . .
C11 C 0.4017(14) 0.5217(6) 0.7848(5) 0.0470(16) Uani 1 1 d . . . . .
C13 C 0.1983(15) 0.6808(6) 0.8368(6) 0.056(2) Uani 1 1 d D . . . .
C15 C -0.0453(19) 0.7957(7) 0.9112(7) 0.069(2) Uani 1 1 d . . . . .
H15A H -0.101578 0.862392 0.919810 0.083 Uiso 0.366(7) 1 calc R U P A 2
H15 H -0.101578 0.862392 0.919810 0.083 Uiso 0.634(7) 1 calc R U P A 1
C16 C -0.1356(19) 0.7175(8) 0.9652(8) 0.071(2) Uani 1 1 d D . . . .
H16A H -0.254560 0.732367 1.007572 0.085 Uiso 0.366(7) 1 calc R U P A 2
H16 H -0.254560 0.732367 1.007572 0.085 Uiso 0.634(7) 1 calc R U P A 1
C18 C 0.1145(14) 0.6015(7) 0.8924(6) 0.0536(18) Uani 1 1 d D . . . .
C21 C 0.6702(12) 0.4602(6) 0.6547(5) 0.0436(15) Uani 1 1 d . . . . .
C22 C 0.6860(13) 0.3842(6) 0.5818(6) 0.0467(16) Uani 1 1 d . . . . .
H22 H 0.590726 0.325361 0.584323 0.056 Uiso 1 1 calc R U . . .
C23 C 0.8369(14) 0.3927(7) 0.5063(6) 0.0529(18) Uani 1 1 d . . . . .
H23 H 0.838281 0.340799 0.458619 0.064 Uiso 1 1 calc R U . . .
C24 C 0.9882(13) 0.4784(7) 0.5004(6) 0.0498(17) Uani 1 1 d . . . . .
C25 C 0.9712(14) 0.5564(7) 0.5723(6) 0.0522(18) Uani 1 1 d . . . . .
H25 H 1.066267 0.615253 0.569647 0.063 Uiso 1 1 calc R U . . .
C26 C 0.8181(13) 0.5476(6) 0.6460(5) 0.0485(16) Uani 1 1 d . . . . .
H26 H 0.811320 0.601040 0.691874 0.058 Uiso 1 1 calc R U . . .
C28 C 1.1955(19) 0.3979(10) 0.3670(7) 0.083(3) Uani 1 1 d . . . . .
H28A H 1.254642 0.342015 0.409245 0.124 Uiso 1 1 calc R U . . .
H28B H 1.314917 0.415959 0.322562 0.124 Uiso 1 1 calc R U . . .
H28C H 1.049060 0.377191 0.328636 0.124 Uiso 1 1 calc R U . . .
C29 C 1.3129(16) 0.5731(9) 0.4281(7) 0.070(3) Uani 1 1 d . . . . .
H29A H 1.222362 0.636149 0.420513 0.105 Uiso 1 1 calc R U . . .
H29B H 1.412592 0.566000 0.373685 0.105 Uiso 1 1 calc R U . . .
H29C H 1.413440 0.574442 0.490100 0.105 Uiso 1 1 calc R U . . .
C31 C 0.4685(12) 0.3360(6) 0.7622(5) 0.0443(16) Uani 1 1 d . . . . .
C32 C 0.2547(13) 0.2852(7) 0.7279(6) 0.0554(19) Uani 1 1 d D . . . .
H32 H 0.133261 0.321107 0.690207 0.066 Uiso 1 1 calc R U . . .
C33 C 0.2221(15) 0.1822(6) 0.7495(7) 0.057(2) Uani 1 1 d D . . . .
H33 H 0.079676 0.149511 0.724938 0.069 Uiso 1 1 calc R U . . .
C34 C 0.3968(15) 0.1263(6) 0.8069(6) 0.055(2) Uani 1 1 d . . . . .
C35 C 0.6075(14) 0.1774(6) 0.8398(6) 0.0559(19) Uani 1 1 d . . . . .
H35 H 0.728419 0.141415 0.877717 0.067 Uiso 1 1 calc R U . . .
C36 C 0.6453(13) 0.2805(6) 0.8182(6) 0.0519(18) Uani 1 1 d . . . . .
H36 H 0.789714 0.312417 0.841428 0.062 Uiso 1 1 calc R U . . .
C37 C 0.356(2) 0.0147(7) 0.8296(9) 0.078(3) Uani 1 1 d . . . . .
H37A H 0.189148 0.003910 0.839724 0.118 Uiso 1 1 calc R U . . .
H37B H 0.455531 -0.004509 0.889013 0.118 Uiso 1 1 calc R U . . .
H37C H 0.398412 -0.026917 0.774649 0.118 Uiso 1 1 calc R U . . .
S12A S 0.2265(15) 0.4703(7) 0.8829(6) 0.0489(10) Uani 0.366(7) 1 d . . P A 2
O20A O 0.451(4) 0.6795(15) 0.709(2) 0.073(3) Uani 0.366(7) 1 d . . P A 2
N14A N -0.0556(16) 0.6179(7) 0.9586(7) 0.067(2) Uani 0.366(7) 1 d D . P A 2
C17A C 0.1230(15) 0.7801(6) 0.8455(6) 0.0618(19) Uani 0.366(7) 1 d . . P A 2
H17A H 0.182831 0.833663 0.808916 0.074 Uiso 0.366(7) 1 calc R U P A 2
C19A C 0.364(6) 0.623(2) 0.769(3) 0.059(4) Uani 0.366(7) 1 d . . P A 2
S12 S 0.4160(7) 0.6578(3) 0.7545(3) 0.0489(10) Uani 0.634(7) 1 d . . P A 1
O20 O 0.207(2) 0.4272(9) 0.9094(10) 0.073(3) Uani 0.634(7) 1 d . . P A 1
N14 N 0.1230(15) 0.7801(6) 0.8455(6) 0.0618(19) Uani 0.634(7) 1 d D . P A 1
C17 C -0.0556(16) 0.6179(7) 0.9586(7) 0.067(2) Uani 0.634(7) 1 d D . P A 1
H17 H -0.112950 0.564837 0.996560 0.080 Uiso 0.634(7) 1 calc R U P A 1
C19 C 0.246(3) 0.5124(15) 0.8695(15) 0.059(4) Uani 0.634(7) 1 d . . P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N27 C24 1.377(10) . ?
N27 C28 1.447(14) . ?
N27 C29 1.453(12) . ?
C1 C11 1.364(11) . ?
C1 C21 1.474(10) . ?
C1 C31 1.485(9) . ?
C11 S12A 1.833(12) . ?
C11 C19A 1.35(3) . ?
C11 S12 1.813(9) . ?
C11 C19 1.50(2) . ?
C13 C18 1.376(12) . ?
C13 C17A 1.361(11) . ?
C13 C19A 1.54(3) . ?
C13 S12 1.736(9) . ?
C13 N14 1.361(11) . ?
C15 H15A 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.368(15) . ?
C15 C17A 1.357(12) . ?
C15 N14 1.357(12) . ?
C16 H16A 0.9300 . ?
C16 H16 0.9300 . ?
C16 N14A 1.371(12) . ?
C16 C17 1.371(12) . ?
C18 S12A 1.818(12) . ?
C18 N14A 1.371(10) . ?
C18 C17 1.371(10) . ?
C18 C19 1.414(19) . ?
C21 C22 1.398(11) . ?
C21 C26 1.410(10) . ?
C22 H22 0.9300 . ?
C22 C23 1.377(10) . ?
C23 H23 0.9300 . ?
C23 C24 1.399(12) . ?
C24 C25 1.407(11) . ?
C25 H25 0.9300 . ?
C25 C26 1.366(10) . ?
C26 H26 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C31 C32 1.398(10) . ?
C31 C36 1.382(10) . ?
C32 H32 0.9300 . ?
C32 C33 1.382(11) . ?
C33 H33 0.9300 . ?
C33 C34 1.387(12) . ?
C34 C35 1.381(12) . ?
C34 C37 1.499(11) . ?
C35 H35 0.9300 . ?
C35 C36 1.388(11) . ?
C36 H36 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
O20A C19A 1.22(4) . ?
C17A H17A 0.9300 . ?
O20 C19 1.26(2) . ?
C17 H17 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
C24 N27 C28 120.4(8) . . ?
C24 N27 C29 120.2(8) . . ?
C28 N27 C29 117.6(8) . . ?
C11 C1 C21 125.8(6) . . ?
C11 C1 C31 119.1(6) . . ?
C21 C1 C31 115.0(6) . . ?
C1 C11 S12A 112.0(6) . . ?
C1 C11 S12 124.5(6) . . ?
C1 C11 C19 128.7(10) . . ?
C19A C11 C1 134.6(16) . . ?
C19A C11 S12A 112.5(16) . . ?
C19 C11 S12 106.8(9) . . ?
C18 C13 C19A 102.0(14) . . ?
C18 C13 S12 120.4(7) . . ?
C17A C13 C18 122.5(8) . . ?
C17A C13 C19A 135.3(15) . . ?
N14 C13 C18 122.5(8) . . ?
N14 C13 S12 117.0(6) . . ?
C16 C15 H15A 118.6 . . ?
C16 C15 H15 118.6 . . ?
C17A C15 H15A 118.6 . . ?
C17A C15 C16 122.8(9) . . ?
N14 C15 H15 118.6 . . ?
N14 C15 C16 122.8(9) . . ?
C15 C16 H16A 119.1 . . ?
C15 C16 H16 119.1 . . ?
C15 C16 N14A 121.7(9) . . ?
C15 C16 C17 121.7(9) . . ?
N14A C16 H16A 119.1 . . ?
C17 C16 H16 119.1 . . ?
C13 C18 S12A 121.7(7) . . ?
C13 C18 C19 106.6(11) . . ?
N14A C18 C13 121.5(8) . . ?
N14A C18 S12A 116.8(7) . . ?
C17 C18 C13 121.5(8) . . ?
C17 C18 C19 131.8(12) . . ?
C22 C21 C1 120.2(6) . . ?
C22 C21 C26 115.7(7) . . ?
C26 C21 C1 124.1(7) . . ?
C21 C22 H22 118.6 . . ?
C23 C22 C21 122.7(7) . . ?
C23 C22 H22 118.6 . . ?
C22 C23 H23 119.5 . . ?
C22 C23 C24 120.9(7) . . ?
C24 C23 H23 119.5 . . ?
N27 C24 C23 121.7(7) . . ?
N27 C24 C25 121.4(7) . . ?
C23 C24 C25 117.0(7) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 C24 121.5(8) . . ?
C26 C25 H25 119.2 . . ?
C21 C26 H26 118.9 . . ?
C25 C26 C21 122.1(7) . . ?
C25 C26 H26 118.9 . . ?
N27 C28 H28A 109.5 . . ?
N27 C28 H28B 109.5 . . ?
N27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N27 C29 H29A 109.5 . . ?
N27 C29 H29B 109.5 . . ?
N27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C32 C31 C1 121.0(6) . . ?
C36 C31 C1 120.6(6) . . ?
C36 C31 C32 118.3(7) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 C31 120.6(7) . . ?
C33 C32 H32 119.7 . . ?
C32 C33 H33 119.2 . . ?
C32 C33 C34 121.5(7) . . ?
C34 C33 H33 119.2 . . ?
C33 C34 C37 120.4(9) . . ?
C35 C34 C33 117.1(7) . . ?
C35 C34 C37 122.4(9) . . ?
C34 C35 H35 118.8 . . ?
C34 C35 C36 122.3(8) . . ?
C36 C35 H35 118.8 . . ?
C31 C36 C35 120.1(7) . . ?
C31 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C18 S12A C11 85.3(6) . . ?
C18 N14A C16 115.8(8) . . ?
C13 C17A H17A 122.2 . . ?
C15 C17A C13 115.6(8) . . ?
C15 C17A H17A 122.2 . . ?
C11 C19A C13 118(2) . . ?
O20A C19A C11 128(3) . . ?
O20A C19A C13 113(3) . . ?
C13 S12 C11 88.7(4) . . ?
C15 N14 C13 115.6(8) . . ?
C16 C17 H17 122.1 . . ?
C18 C17 C16 115.8(8) . . ?
C18 C17 H17 122.1 . . ?
C18 C19 C11 116.5(16) . . ?
O20 C19 C11 122.0(14) . . ?
O20 C19 C18 120.8(16) . . ?

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
N27 C24 C25 C26 -178.3(8) . . . . ?
C1 C11 S12A C18 -171.0(6) . . . . ?
C1 C11 C19A C13 171.5(12) . . . . ?
C1 C11 C19A O20A -11(5) . . . . ?
C1 C11 S12 C13 170.6(7) . . . . ?
C1 C11 C19 C18 -166.7(10) . . . . ?
C1 C11 C19 O20 4(2) . . . . ?
C1 C21 C22 C23 -178.2(7) . . . . ?
C1 C21 C26 C25 177.2(7) . . . . ?
C1 C31 C32 C33 176.9(7) . . . . ?
C1 C31 C36 C35 -177.6(7) . . . . ?
C11 C1 C21 C22 -151.9(7) . . . . ?
C11 C1 C21 C26 29.6(10) . . . . ?
C11 C1 C31 C32 78.6(9) . . . . ?
C11 C1 C31 C36 -104.5(9) . . . . ?
C13 C18 S12A C11 -3.7(8) . . . . ?
C13 C18 N14A C16 0.2(13) . . . . ?
C13 C18 C17 C16 0.2(13) . . . . ?
C13 C18 C19 C11 -9.1(15) . . . . ?
C13 C18 C19 O20 -179.8(15) . . . . ?
C15 C16 N14A C18 -1.9(15) . . . . ?
C15 C16 C17 C18 -1.9(15) . . . . ?
C16 C15 C17A C13 -0.3(14) . . . . ?
C16 C15 N14 C13 -0.3(14) . . . . ?
C18 C13 C17A C15 -1.5(12) . . . . ?
C18 C13 C19A C11 -6(3) . . . . ?
C18 C13 C19A O20A 177(3) . . . . ?
C18 C13 S12 C11 3.5(7) . . . . ?
C18 C13 N14 C15 -1.5(12) . . . . ?
C21 C1 C11 S12A -178.0(6) . . . . ?
C21 C1 C11 C19A 14(2) . . . . ?
C21 C1 C11 S12 4.6(10) . . . . ?
C21 C1 C11 C19 -177.5(11) . . . . ?
C21 C1 C31 C32 -101.2(8) . . . . ?
C21 C1 C31 C36 75.8(9) . . . . ?
C21 C22 C23 C24 1.5(11) . . . . ?
C22 C21 C26 C25 -1.4(10) . . . . ?
C22 C23 C24 N27 177.4(7) . . . . ?
C22 C23 C24 C25 -2.5(11) . . . . ?
C23 C24 C25 C26 1.5(11) . . . . ?
C24 C25 C26 C21 0.4(12) . . . . ?
C26 C21 C22 C23 0.4(10) . . . . ?
C28 N27 C24 C23 -11.6(12) . . . . ?
C28 N27 C24 C25 168.2(9) . . . . ?
C29 N27 C24 C23 -175.9(8) . . . . ?
C29 N27 C24 C25 4.0(11) . . . . ?
C31 C1 C11 S12A 2.4(8) . . . . ?
C31 C1 C11 C19A -166(2) . . . . ?
C31 C1 C11 S12 -175.1(5) . . . . ?
C31 C1 C11 C19 2.8(13) . . . . ?
C31 C1 C21 C22 27.8(9) . . . . ?
C31 C1 C21 C26 -150.7(7) . . . . ?
C31 C32 C33 C34 1.1(12) . . . . ?
C32 C31 C36 C35 -0.5(11) . . . . ?
C32 C33 C34 C35 -1.4(12) . . . . ?
C32 C33 C34 C37 179.7(8) . . . . ?
C33 C34 C35 C36 0.8(12) . . . . ?
C34 C35 C36 C31 0.2(12) . . . . ?
C36 C31 C32 C33 -0.1(12) . . . . ?
C37 C34 C35 C36 179.6(8) . . . . ?
S12A C11 C19A C13 3(3) . . . . ?
S12A C11 C19A O20A -179(3) . . . . ?
S12A C18 N14A C16 179.4(8) . . . . ?
N14A C18 S12A C11 177.1(7) . . . . ?
C17A C13 C18 S12A -177.6(7) . . . . ?
C17A C13 C18 N14A 1.6(12) . . . . ?
C17A C13 C19A C11 178.3(14) . . . . ?
C17A C13 C19A O20A 1(4) . . . . ?
C17A C15 C16 N14A 2.0(17) . . . . ?
C19A C11 S12A C18 -0.2(19) . . . . ?
C19A C13 C18 S12A 5.6(15) . . . . ?
C19A C13 C18 N14A -175.2(15) . . . . ?
C19A C13 C17A C15 174(2) . . . . ?
S12 C11 C19 C18 11.5(15) . . . . ?
S12 C11 C19 O20 -177.9(14) . . . . ?
S12 C13 C18 C17 179.4(7) . . . . ?
S12 C13 C18 C19 2.4(11) . . . . ?
S12 C13 N14 C15 -179.3(7) . . . . ?
N14 C13 C18 C17 1.6(12) . . . . ?
N14 C13 C18 C19 -175.4(11) . . . . ?
N14 C13 S12 C11 -178.6(7) . . . . ?
N14 C15 C16 C17 2.0(17) . . . . ?
C17 C18 C19 C11 174.4(9) . . . . ?
C17 C18 C19 O20 4(2) . . . . ?
C19 C11 S12 C13 -7.7(9) . . . . ?
C19 C18 C17 C16 176.3(13) . . . . ?


_olex2_date_sample_data_collection 2021-08-25
_olex2_diffrn_ambient_temperature_device 'Cryojet - Oxford Instruments'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a mylar loop in perfluoroether oil'
_olex2_submission_original_sample_id MZ190
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.333
_oxdiff_exptl_absorpt_empirical_full_min 0.825
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.86(7)
2 0.14(7)

####################################################################### 
# 
# 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_21dub_mz05
_database_code_depnum_ccdc_archive 'CCDC 2227018'
loop_
_audit_author_name
_audit_author_address
'Frank Hampel'
;Lehrstuhl fuer Organische Chemie I, FAU Erlangen Nuernberg
Germany
;
_audit_update_record             
;
2022-12-16 deposited with the CCDC.	2023-05-01 downloaded from the CCDC.
;
_audit_creation_date             2021-08-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
max.zitzmann@fau.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 N3 O S'
_chemical_formula_sum            'C23 H17 N3 O S'
_chemical_formula_weight         383.45
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H17 N3 O S'
_chemical_oxdiff_usercomment     MZ-128
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.1543(2)
_cell_length_b                   11.4783(4)
_cell_length_c                   23.2717(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1911.05(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3358
_cell_measurement_temperature    153(1)
_cell_measurement_theta_max      72.1350
_cell_measurement_theta_min      3.7730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.648
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light red'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -4 -2 0.0991
-2 -6 -5 0.1003
5 -1 -2 0.1334
-1 7 6 0.0938
0 0 15 0.0418
0 0 -15 0.0418

_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of DCM and hexane  by solvent layering'
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.084
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.9137 -3.8861 -1.9692 -0.7391 0.2598 0.6215
-1.8433 -6.4503 -4.5767 -0.9405 0.3321 0.0725
4.5067 -1.3672 -2.3471 0.1020 -0.0340 -0.9942
-0.6622 6.8358 5.5857 0.8357 -0.2962 0.4624
0.0011 -0.1176 15.1065 -0.0247 -0.9820 0.1873
-0.0011 0.1176 -15.1065 0.0247 0.9820 -0.1873

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            6676
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.180
_diffrn_reflns_theta_min         3.799
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      153(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6144
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -112.00 -30.00   1.00    1.00    --  -42.18 -38.00  90.00   82
  2  ω    -15.00  68.00   1.00    1.00    --   42.18 -19.00  90.00   83
  3  ω     82.00 173.00   1.00    1.00    --  104.13  45.00 -60.00   91
  4  ω     94.00 174.00   1.00    1.00    --  104.13 125.00 150.00   80
  5  ω    134.00 172.00   1.00    1.00    --  104.13 125.00 -90.00   38
  6  ω     77.00 174.00   1.00    1.00    --  104.13  30.00 120.00   97
  7  ω     77.00 108.00   1.00    1.00    --  104.13-125.00 -60.00   31
  8  ω    126.00 175.00   1.00    1.00    --  104.13 125.00 -30.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0613445000
_diffrn_orient_matrix_UB_12      0.1287208000
_diffrn_orient_matrix_UB_13      -0.0006349000
_diffrn_orient_matrix_UB_21      -0.0395763000
_diffrn_orient_matrix_UB_22      0.0059146000
_diffrn_orient_matrix_UB_23      -0.0649564000
_diffrn_orient_matrix_UB_31      -0.2025716000
_diffrn_orient_matrix_UB_32      0.0376373000
_diffrn_orient_matrix_UB_33      0.0127035000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                3376
_reflns_number_total             3658
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 1261 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3658
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.065
_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)+(0.0790P)²+0.4071P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1355
_refine_special_details          
;
Space Group P2121212; Absoluter structure determined
;
_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:
 C15(H15), C16(H16), C17(H17), C22(H22), C23(H23), C25(H25), C26(H26),
 C32(H32), C33(H33), C35(H35), C36(H36)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
S12 S 0.25964(15) 0.81557(7) 0.76740(4) 0.0353(3) Uani 1 1 d . . . . .
O19 O 0.2445(5) 0.7217(2) 0.60989(11) 0.0389(6) Uani 1 1 d . . . . .
N14 N 0.1681(5) 1.0347(3) 0.73721(19) 0.0445(9) Uani 1 1 d . . . . .
N27 N 0.3453(6) 0.3658(3) 0.93542(14) 0.0449(9) Uani 1 1 d . . . . .
N38 N 0.3180(6) 0.2103(4) 0.49400(18) 0.0568(11) Uani 1 1 d . . . . .
C1 C 0.3058(4) 0.5956(3) 0.71958(14) 0.0250(7) Uani 1 1 d . . . . .
C11 C 0.2753(5) 0.7111(3) 0.71038(15) 0.0290(8) Uani 1 1 d . . . . .
C13 C 0.2013(5) 0.9260(3) 0.71861(19) 0.0358(9) Uani 1 1 d . . . . .
C15 C 0.1168(6) 1.1097(4) 0.6966(3) 0.0512(12) Uani 1 1 d . . . . .
H15 H 0.092958 1.186145 0.707649 0.061 Uiso 1 1 calc R U . . .
C16 C 0.0963(6) 1.0818(4) 0.6389(3) 0.0519(13) Uani 1 1 d . . . . .
H16 H 0.055739 1.138075 0.613048 0.062 Uiso 1 1 calc R U . . .
C17 C 0.1363(6) 0.9698(4) 0.6198(2) 0.0469(11) Uani 1 1 d . . . . .
H17 H 0.126762 0.949094 0.581265 0.056 Uiso 1 1 calc R U . . .
C18 C 0.1913(5) 0.8905(3) 0.6617(2) 0.0378(9) Uani 1 1 d . . . . .
C19 C 0.2397(6) 0.7666(3) 0.65347(17) 0.0374(8) Uani 1 1 d . . . . .
C21 C 0.3323(5) 0.5372(3) 0.77452(15) 0.0264(7) Uani 1 1 d . . . . .
C22 C 0.2938(5) 0.4169(3) 0.77961(14) 0.0287(7) Uani 1 1 d . . . . .
H22 H 0.262597 0.374930 0.746816 0.034 Uiso 1 1 calc R U . . .
C23 C 0.3011(5) 0.3597(3) 0.83196(16) 0.0314(8) Uani 1 1 d . . . . .
H23 H 0.274179 0.280454 0.833596 0.038 Uiso 1 1 calc R U . . .
C24 C 0.3484(5) 0.4192(4) 0.88250(15) 0.0333(8) Uani 1 1 d . . . . .
C25 C 0.3993(6) 0.5368(4) 0.87724(16) 0.0345(8) Uani 1 1 d . . . . .
H25 H 0.439051 0.577263 0.909643 0.041 Uiso 1 1 calc R U . . .
C26 C 0.3918(5) 0.5937(3) 0.82511(16) 0.0307(8) Uani 1 1 d . . . . .
H26 H 0.426975 0.671623 0.823266 0.037 Uiso 1 1 calc R U . . .
C28 C 0.3892(11) 0.4290(5) 0.98671(19) 0.0671(17) Uani 1 1 d . . . . .
H28A H 0.519482 0.448986 0.986672 0.101 Uiso 1 1 calc R U . . .
H28B H 0.361928 0.381576 1.019633 0.101 Uiso 1 1 calc R U . . .
H28C H 0.315565 0.498879 0.988212 0.101 Uiso 1 1 calc R U . . .
C29 C 0.2938(8) 0.2438(4) 0.94013(19) 0.0542(13) Uani 1 1 d . . . . .
H29A H 0.170803 0.232559 0.924613 0.081 Uiso 1 1 calc R U . . .
H29B H 0.295001 0.220974 0.979817 0.081 Uiso 1 1 calc R U . . .
H29C H 0.381663 0.197145 0.919072 0.081 Uiso 1 1 calc R U . . .
C31 C 0.3070(5) 0.5154(3) 0.66808(14) 0.0248(7) Uani 1 1 d . . . . .
C32 C 0.1401(5) 0.4703(3) 0.64662(16) 0.0291(8) Uani 1 1 d . . . . .
H32 H 0.026781 0.493205 0.662620 0.035 Uiso 1 1 calc R U . . .
C33 C 0.1425(5) 0.3914(3) 0.60147(16) 0.0307(8) Uani 1 1 d . . . . .
H33 H 0.031400 0.361485 0.586918 0.037 Uiso 1 1 calc R U . . .
C34 C 0.3127(6) 0.3577(3) 0.57833(15) 0.0311(8) Uani 1 1 d . . . . .
C35 C 0.4804(6) 0.4023(4) 0.59906(16) 0.0329(8) Uani 1 1 d . . . . .
H35 H 0.593673 0.379479 0.583012 0.039 Uiso 1 1 calc R U . . .
C36 C 0.4760(5) 0.4818(3) 0.64425(16) 0.0297(8) Uani 1 1 d . . . . .
H36 H 0.586995 0.512522 0.658493 0.036 Uiso 1 1 calc R U . . .
C37 C 0.3168(6) 0.2758(4) 0.53120(18) 0.0403(9) 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
S12 C11 1.792(4) . ?
S12 C13 1.752(4) . ?
O19 C19 1.138(5) . ?
N14 C13 1.342(5) . ?
N14 C15 1.330(6) . ?
N27 C24 1.376(5) . ?
N27 C28 1.432(6) . ?
N27 C29 1.452(6) . ?
N38 C37 1.146(5) . ?
C1 C11 1.361(5) . ?
C1 C21 1.456(5) . ?
C1 C31 1.511(4) . ?
C11 C19 1.492(5) . ?
C13 C18 1.388(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.388(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.390(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.390(6) . ?
C18 C19 1.476(6) . ?
C21 C22 1.412(5) . ?
C21 C26 1.410(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.385(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.402(5) . ?
C24 C25 1.403(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.379(5) . ?
C26 H26 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C31 C32 1.394(5) . ?
C31 C36 1.385(5) . ?
C32 H32 0.9300 . ?
C32 C33 1.387(5) . ?
C33 H33 0.9300 . ?
C33 C34 1.386(5) . ?
C34 C35 1.391(6) . ?
C34 C37 1.445(5) . ?
C35 H35 0.9300 . ?
C35 C36 1.393(5) . ?
C36 H36 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
C13 S12 C11 91.10(18) . . ?
C15 N14 C13 114.9(4) . . ?
C24 N27 C28 121.1(4) . . ?
C24 N27 C29 120.1(4) . . ?
C28 N27 C29 118.8(4) . . ?
C11 C1 C21 127.4(3) . . ?
C11 C1 C31 118.0(3) . . ?
C21 C1 C31 114.6(3) . . ?
C1 C11 S12 123.1(3) . . ?
C1 C11 C19 125.7(3) . . ?
C19 C11 S12 111.2(3) . . ?
N14 C13 S12 120.4(4) . . ?
N14 C13 C18 124.9(4) . . ?
C18 C13 S12 114.7(3) . . ?
N14 C15 H15 117.7 . . ?
N14 C15 C16 124.5(4) . . ?
C16 C15 H15 117.7 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.1(5) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 122.0 . . ?
C18 C17 C16 116.0(5) . . ?
C18 C17 H17 122.0 . . ?
C13 C18 C17 119.4(4) . . ?
C13 C18 C19 113.2(4) . . ?
C17 C18 C19 127.3(4) . . ?
O19 C19 C11 126.3(4) . . ?
O19 C19 C18 124.0(4) . . ?
C18 C19 C11 109.7(3) . . ?
C22 C21 C1 119.9(3) . . ?
C26 C21 C1 124.1(3) . . ?
C26 C21 C22 116.0(3) . . ?
C21 C22 H22 119.0 . . ?
C23 C22 C21 122.0(3) . . ?
C23 C22 H22 119.0 . . ?
C22 C23 H23 119.5 . . ?
C22 C23 C24 121.0(3) . . ?
C24 C23 H23 119.5 . . ?
N27 C24 C23 122.0(4) . . ?
N27 C24 C25 120.7(4) . . ?
C23 C24 C25 117.3(3) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 C24 121.5(4) . . ?
C26 C25 H25 119.3 . . ?
C21 C26 H26 119.0 . . ?
C25 C26 C21 121.9(4) . . ?
C25 C26 H26 119.0 . . ?
N27 C28 H28A 109.5 . . ?
N27 C28 H28B 109.5 . . ?
N27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N27 C29 H29A 109.5 . . ?
N27 C29 H29B 109.5 . . ?
N27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C32 C31 C1 120.3(3) . . ?
C36 C31 C1 119.5(3) . . ?
C36 C31 C32 120.1(3) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 C31 120.2(3) . . ?
C33 C32 H32 119.9 . . ?
C32 C33 H33 120.4 . . ?
C34 C33 C32 119.2(3) . . ?
C34 C33 H33 120.4 . . ?
C33 C34 C35 121.3(3) . . ?
C33 C34 C37 119.6(3) . . ?
C35 C34 C37 119.0(4) . . ?
C34 C35 H35 120.5 . . ?
C34 C35 C36 118.9(4) . . ?
C36 C35 H35 120.5 . . ?
C31 C36 C35 120.3(4) . . ?
C31 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
N38 C37 C34 179.2(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
S12 C11 C19 O19 178.2(4) . . . . ?
S12 C11 C19 C18 -3.2(4) . . . . ?
S12 C13 C18 C17 176.6(3) . . . . ?
S12 C13 C18 C19 -2.3(4) . . . . ?
N14 C13 C18 C17 -2.7(6) . . . . ?
N14 C13 C18 C19 178.5(4) . . . . ?
N14 C15 C16 C17 -2.2(7) . . . . ?
N27 C24 C25 C26 -175.8(4) . . . . ?
C1 C11 C19 O19 -5.2(7) . . . . ?
C1 C11 C19 C18 173.3(3) . . . . ?
C1 C21 C22 C23 -174.3(3) . . . . ?
C1 C21 C26 C25 174.3(3) . . . . ?
C1 C31 C32 C33 -176.2(3) . . . . ?
C1 C31 C36 C35 176.0(3) . . . . ?
C11 S12 C13 N14 179.6(3) . . . . ?
C11 S12 C13 C18 0.3(3) . . . . ?
C11 C1 C21 C22 156.5(4) . . . . ?
C11 C1 C21 C26 -22.1(6) . . . . ?
C11 C1 C31 C32 -84.8(4) . . . . ?
C11 C1 C31 C36 98.7(4) . . . . ?
C13 S12 C11 C1 -174.9(3) . . . . ?
C13 S12 C11 C19 1.7(3) . . . . ?
C13 N14 C15 C16 0.3(6) . . . . ?
C13 C18 C19 O19 -177.9(4) . . . . ?
C13 C18 C19 C11 3.5(5) . . . . ?
C15 N14 C13 S12 -177.0(3) . . . . ?
C15 N14 C13 C18 2.2(6) . . . . ?
C15 C16 C17 C18 1.6(6) . . . . ?
C16 C17 C18 C13 0.6(6) . . . . ?
C16 C17 C18 C19 179.3(4) . . . . ?
C17 C18 C19 O19 3.3(7) . . . . ?
C17 C18 C19 C11 -175.2(4) . . . . ?
C21 C1 C11 S12 -0.7(5) . . . . ?
C21 C1 C11 C19 -176.9(4) . . . . ?
C21 C1 C31 C32 93.3(4) . . . . ?
C21 C1 C31 C36 -83.1(4) . . . . ?
C21 C22 C23 C24 -0.3(6) . . . . ?
C22 C21 C26 C25 -4.4(5) . . . . ?
C22 C23 C24 N27 175.9(4) . . . . ?
C22 C23 C24 C25 -4.0(6) . . . . ?
C23 C24 C25 C26 4.0(6) . . . . ?
C24 C25 C26 C21 0.2(6) . . . . ?
C26 C21 C22 C23 4.4(5) . . . . ?
C28 N27 C24 C23 -178.3(5) . . . . ?
C28 N27 C24 C25 1.6(7) . . . . ?
C29 N27 C24 C23 0.7(6) . . . . ?
C29 N27 C24 C25 -179.5(4) . . . . ?
C31 C1 C11 S12 177.1(2) . . . . ?
C31 C1 C11 C19 1.0(5) . . . . ?
C31 C1 C21 C22 -21.4(5) . . . . ?
C31 C1 C21 C26 160.0(3) . . . . ?
C31 C32 C33 C34 0.4(6) . . . . ?
C32 C31 C36 C35 -0.5(5) . . . . ?
C32 C33 C34 C35 -0.7(6) . . . . ?
C32 C33 C34 C37 -179.8(4) . . . . ?
C33 C34 C35 C36 0.4(6) . . . . ?
C34 C35 C36 C31 0.1(6) . . . . ?
C36 C31 C32 C33 0.2(5) . . . . ?
C37 C34 C35 C36 179.6(4) . . . . ?


_olex2_date_sample_data_collection 2021-06-25
_olex2_date_sample_submission    2021-06-07
_olex2_diffrn_ambient_temperature_device 'Cryojet - Oxford Instruments'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a mylar loop in perfluoroether oil'
_olex2_submission_original_sample_id MZ128
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.276
_oxdiff_exptl_absorpt_empirical_full_min 0.861
####################################################################### 
# 
# 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_22dub_mz03
_database_code_depnum_ccdc_archive 'CCDC 2227451'
loop_
_audit_author_name
_audit_author_address
'Frank Hampel'
;Lehrstuhl fuer Organische Chemie I, FAU Erlangen Nuernberg
Germany
;
_audit_update_record             
;
2023-04-20 deposited with the CCDC.	2023-05-01 downloaded from the CCDC.
;
_audit_creation_date             2022-04-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
max.zitzmann@fau.de
?
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 N O2 S'
_chemical_formula_sum            'C17 H15 N O2 S'
_chemical_formula_weight         297.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H15 N O2 S'
_chemical_oxdiff_usercomment     MZ296
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   15.6601(2)
_cell_length_b                   7.17100(10)
_cell_length_c                   12.72030(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.1630(10)
_cell_angle_gamma                90
_cell_volume                     1420.22(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7040
_cell_measurement_temperature    153.00(10)
_cell_measurement_theta_max      71.4760
_cell_measurement_theta_min      3.4740
_shelx_estimated_absorpt_T_max   0.733
_shelx_estimated_absorpt_T_min   0.613
_exptl_absorpt_coefficient_mu    2.053
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.585
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 4 -3 0.0886
8 -3 -3 0.0799
1 -4 2 0.0909
-7 -2 5 0.0760
5 4 -2 0.1004
6 0 -7 0.0709
-2 -4 -1 0.0538
-6 -3 5 0.0820
-4 2 7 0.1453
7 3 -4 0.0846
-2 2 -7 0.0781
-7 0 -5 0.0754
-4 -3 6 0.1090
1 5 2 0.0976
7 1 4 0.1225

_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_min          0.161
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.6367 4.3274 -3.0320 -0.1462 -0.6047 0.7829
7.9264 -2.6819 -2.6933 0.2244 0.9398 0.2579
1.2114 -4.4489 2.0918 0.1803 0.7484 -0.6382
-6.9028 -2.2290 5.1746 -0.0304 -0.1349 -0.9904
4.7261 3.9945 -2.2063 0.2052 -0.3807 0.9016
5.6663 -0.2199 -7.3012 -0.3137 0.5737 0.7566
-2.4122 -4.4583 -1.1228 -0.3751 0.6919 -0.6169
-6.1187 -2.5696 5.2748 0.0250 -0.0422 -0.9988
-3.9387 2.1308 6.9135 0.4390 -0.8056 -0.3978
7.0202 2.6923 -4.1829 0.1438 0.0250 0.9893
-1.7736 1.8598 -7.2324 -0.7691 -0.1442 0.6227
-7.2657 0.1040 -5.1038 -0.9827 -0.1828 -0.0309
-4.3495 -2.7237 6.0368 0.2155 0.0418 -0.9756
0.7164 4.5028 1.9332 0.3372 -0.8103 0.4792
7.4475 1.2842 4.4596 0.9656 -0.0241 0.2590

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8644
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.537
_diffrn_reflns_theta_min         2.838
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      153.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6144
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00 -18.00   1.00    1.00    --  -42.69 -38.00-150.00   99
  2  ω    -59.00  27.00   1.00    1.00    --  -42.69  57.00   0.00   86
  3  ω    -73.00  32.00   1.00    1.00    --  -42.69  73.00 162.00  105
  4  ω     29.00 113.00   1.00    3.46    --  102.49-125.00 120.00   84
  5  ω     24.00 104.00   1.00    3.46    --  102.49 -94.00 150.00   80
  6  ω     74.00 141.00   1.00    3.46    --  102.49  61.00-120.00   67
  7  ω     77.00 164.00   1.00    3.46    --  102.49  45.00  60.00   87
  8  ω    142.00 174.00   1.00    3.46    --  102.49  61.00-120.00   32
  9  ω     98.00 160.00   1.00    3.46    --  102.49 125.00 -60.00   62
 10  ω    123.00 178.00   1.00    3.46    --  102.49  77.00  30.00   55
 11  ω     81.00 174.00   1.00    3.46    --  102.49  30.00 -60.00   93
 12  ω     21.00 153.00   1.00    3.46    --  102.49 -15.00-120.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0685272000
_diffrn_orient_matrix_UB_12      0.0230152000
_diffrn_orient_matrix_UB_13      0.0954501000
_diffrn_orient_matrix_UB_21      0.0480602000
_diffrn_orient_matrix_UB_22      -0.1721126000
_diffrn_orient_matrix_UB_23      -0.0360993000
_diffrn_orient_matrix_UB_31      0.0527651000
_diffrn_orient_matrix_UB_32      0.1265667000
_diffrn_orient_matrix_UB_33      -0.0664890000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2611
_reflns_number_total             2717
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2717
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.068
_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)+(0.0500P)²+0.3563P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0850
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C22(H22), C23(H23), C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
S12 S 0.16541(2) 0.64331(4) 0.36851(2) 0.02743(13) Uani 1 1 d . . . . .
O1 O 0.27669(6) 0.59631(13) 0.10145(7) 0.0312(2) Uani 1 1 d . . . . .
O2 O 0.11553(6) 0.60008(15) 0.06329(7) 0.0347(2) Uani 1 1 d . . . . .
H2 H 0.166233 0.595255 0.047600 0.052 Uiso 1 1 calc R U . . .
N27 N 0.59919(7) 0.67126(15) 0.44306(8) 0.0274(2) Uani 1 1 d . . . . .
C1 C 0.27428(8) 0.62003(15) 0.19945(9) 0.0239(3) Uani 1 1 d . . . . .
C11 C 0.19031(8) 0.62809(16) 0.23747(9) 0.0239(3) Uani 1 1 d . . . . .
C13 C 0.05601(8) 0.63900(16) 0.32719(10) 0.0270(3) Uani 1 1 d . . . . .
C14 C -0.01049(9) 0.65074(19) 0.39175(11) 0.0343(3) Uani 1 1 d . . . . .
H14 H 0.001310 0.662956 0.466260 0.041 Uiso 1 1 calc R U . . .
C15 C -0.09380(9) 0.6441(2) 0.34412(13) 0.0389(3) Uani 1 1 d . . . . .
H15 H -0.139890 0.651513 0.386798 0.047 Uiso 1 1 calc R U . . .
C16 C -0.11212(9) 0.6266(2) 0.23429(12) 0.0373(3) Uani 1 1 d . . . . .
H16 H -0.170169 0.621963 0.203757 0.045 Uiso 1 1 calc R U . . .
C17 C -0.04698(9) 0.61620(19) 0.17038(11) 0.0333(3) Uani 1 1 d . . . . .
H17 H -0.059407 0.604249 0.095927 0.040 Uiso 1 1 calc R U . . .
C18 C 0.03845(8) 0.62355(16) 0.21720(10) 0.0267(3) Uani 1 1 d . . . . .
C19 C 0.11626(8) 0.61651(16) 0.16772(9) 0.0258(3) Uani 1 1 d . . . . .
C21 C 0.35590(8) 0.63527(15) 0.26782(9) 0.0225(3) Uani 1 1 d . . . . .
C22 C 0.36585(7) 0.71277(16) 0.36983(9) 0.0236(2) Uani 1 1 d . . . . .
H22 H 0.316792 0.758481 0.399521 0.028 Uiso 1 1 calc R U . . .
C23 C 0.44549(7) 0.72392(16) 0.42791(9) 0.0237(2) Uani 1 1 d . . . . .
H23 H 0.450091 0.777672 0.496542 0.028 Uiso 1 1 calc R U . . .
C24 C 0.52029(8) 0.65694(15) 0.38726(10) 0.0229(3) Uani 1 1 d . . . . .
C25 C 0.50976(8) 0.57641(16) 0.28509(9) 0.0252(3) Uani 1 1 d . . . . .
H25 H 0.558266 0.526878 0.255817 0.030 Uiso 1 1 calc R U . . .
C26 C 0.43034(8) 0.56890(16) 0.22770(9) 0.0241(2) Uani 1 1 d . . . . .
H26 H 0.425600 0.517107 0.158577 0.029 Uiso 1 1 calc R U . . .
C28 C 0.67524(9) 0.6041(2) 0.39965(12) 0.0384(3) Uani 1 1 d . . . . .
H28A H 0.668412 0.471332 0.382515 0.058 Uiso 1 1 calc R U . . .
H28B H 0.725449 0.621322 0.451735 0.058 Uiso 1 1 calc R U . . .
H28C H 0.683349 0.674185 0.335335 0.058 Uiso 1 1 calc R U . . .
C29 C 0.61024(8) 0.75950(18) 0.54650(10) 0.0314(3) Uani 1 1 d . . . . .
H29A H 0.592793 0.890573 0.539751 0.047 Uiso 1 1 calc R U . . .
H29B H 0.670709 0.752179 0.575463 0.047 Uiso 1 1 calc R U . . .
H29C H 0.574658 0.695248 0.594014 0.047 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S12 C11 1.7556(12) . ?
S12 C13 1.7376(13) . ?
O1 C1 1.2627(15) . ?
O2 H2 0.8400 . ?
O2 C19 1.3324(15) . ?
N27 C24 1.3612(16) . ?
N27 C28 1.4479(17) . ?
N27 C29 1.4535(16) . ?
C1 C11 1.4502(17) . ?
C1 C21 1.4709(16) . ?
C11 C19 1.3850(17) . ?
C13 C14 1.3962(19) . ?
C13 C18 1.4009(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.379(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.401(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.373(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.4058(18) . ?
C18 C19 1.4311(18) . ?
C21 C22 1.4049(16) . ?
C21 C26 1.4048(16) . ?
C22 H22 0.9500 . ?
C22 C23 1.3820(16) . ?
C23 H23 0.9500 . ?
C23 C24 1.4142(17) . ?
C24 C25 1.4155(17) . ?
C25 H25 0.9500 . ?
C25 C26 1.3741(17) . ?
C26 H26 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 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
C13 S12 C11 91.37(6) . . ?
C19 O2 H2 109.5 . . ?
C24 N27 C28 120.92(11) . . ?
C24 N27 C29 121.20(10) . . ?
C28 N27 C29 117.85(10) . . ?
O1 C1 C11 117.31(11) . . ?
O1 C1 C21 118.53(11) . . ?
C11 C1 C21 124.15(11) . . ?
C1 C11 S12 128.39(9) . . ?
C19 C11 S12 110.85(9) . . ?
C19 C11 C1 120.72(11) . . ?
C14 C13 S12 126.47(11) . . ?
C14 C13 C18 120.89(12) . . ?
C18 C13 S12 112.64(10) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 C13 118.01(13) . . ?
C15 C14 H14 121.0 . . ?
C14 C15 H15 119.2 . . ?
C14 C15 C16 121.59(13) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.64(13) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.74(13) . . ?
C18 C17 H17 120.6 . . ?
C13 C18 C17 120.13(12) . . ?
C13 C18 C19 110.91(11) . . ?
C17 C18 C19 128.96(12) . . ?
O2 C19 C11 124.12(11) . . ?
O2 C19 C18 121.67(11) . . ?
C11 C19 C18 114.21(11) . . ?
C22 C21 C1 125.36(11) . . ?
C22 C21 C26 117.10(11) . . ?
C26 C21 C1 117.53(10) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.39(10) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 H23 119.3 . . ?
C22 C23 C24 121.35(10) . . ?
C24 C23 H23 119.3 . . ?
N27 C24 C23 121.66(11) . . ?
N27 C24 C25 121.28(11) . . ?
C23 C24 C25 117.06(11) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 C24 120.89(11) . . ?
C26 C25 H25 119.6 . . ?
C21 C26 H26 118.9 . . ?
C25 C26 C21 122.19(11) . . ?
C25 C26 H26 118.9 . . ?
N27 C28 H28A 109.5 . . ?
N27 C28 H28B 109.5 . . ?
N27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N27 C29 H29A 109.5 . . ?
N27 C29 H29B 109.5 . . ?
N27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
S12 C11 C19 O2 -178.70(10) . . . . ?
S12 C11 C19 C18 1.26(13) . . . . ?
S12 C13 C14 C15 -179.74(10) . . . . ?
S12 C13 C18 C17 179.36(10) . . . . ?
S12 C13 C18 C19 -0.36(13) . . . . ?
O1 C1 C11 S12 175.20(9) . . . . ?
O1 C1 C11 C19 -2.17(17) . . . . ?
O1 C1 C21 C22 160.81(11) . . . . ?
O1 C1 C21 C26 -18.46(15) . . . . ?
N27 C24 C25 C26 -177.52(11) . . . . ?
C1 C11 C19 O2 -0.91(18) . . . . ?
C1 C11 C19 C18 179.06(10) . . . . ?
C1 C21 C22 C23 -178.98(10) . . . . ?
C1 C21 C26 C25 -179.95(10) . . . . ?
C11 S12 C13 C14 -178.53(12) . . . . ?
C11 S12 C13 C18 0.90(9) . . . . ?
C11 C1 C21 C22 -20.02(18) . . . . ?
C11 C1 C21 C26 160.71(11) . . . . ?
C13 S12 C11 C1 -178.80(11) . . . . ?
C13 S12 C11 C19 -1.22(9) . . . . ?
C13 C14 C15 C16 -0.2(2) . . . . ?
C13 C18 C19 O2 179.37(11) . . . . ?
C13 C18 C19 C11 -0.60(15) . . . . ?
C14 C13 C18 C17 -1.18(18) . . . . ?
C14 C13 C18 C19 179.11(11) . . . . ?
C14 C15 C16 C17 -0.2(2) . . . . ?
C15 C16 C17 C18 -0.1(2) . . . . ?
C16 C17 C18 C13 0.75(19) . . . . ?
C16 C17 C18 C19 -179.60(13) . . . . ?
C17 C18 C19 O2 -0.3(2) . . . . ?
C17 C18 C19 C11 179.72(12) . . . . ?
C18 C13 C14 C15 0.88(19) . . . . ?
C21 C1 C11 S12 -3.98(17) . . . . ?
C21 C1 C11 C19 178.65(10) . . . . ?
C21 C22 C23 C24 -0.30(17) . . . . ?
C22 C21 C26 C25 0.73(17) . . . . ?
C22 C23 C24 N27 178.51(10) . . . . ?
C22 C23 C24 C25 -0.64(16) . . . . ?
C23 C24 C25 C26 1.63(16) . . . . ?
C24 C25 C26 C21 -1.72(17) . . . . ?
C26 C21 C22 C23 0.29(16) . . . . ?
C28 N27 C24 C23 -179.19(12) . . . . ?
C28 N27 C24 C25 -0.08(17) . . . . ?
C29 N27 C24 C23 -1.15(17) . . . . ?
C29 N27 C24 C25 177.96(11) . . . . ?

_olex2_date_sample_data_collection 2022-04-12
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a mylar loop in perfluoroether oil'
_olex2_submission_original_sample_id MZ296
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.251
_oxdiff_exptl_absorpt_empirical_full_min 0.851
####################################################################### 
# 
# 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_21dub_mz04
_database_code_depnum_ccdc_archive 'CCDC 2227016'
loop_
_audit_author_name
_audit_author_address
'Frank Hampel'
;Lehrstuhl fuer Organische Chemie I, FAU Erlangen Nuernberg
Germany
;
_audit_update_record             
;
2022-12-16 deposited with the CCDC.	2023-05-01 downloaded from the CCDC.
;
_audit_creation_date             2021-08-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
max.zitzmann@fau.de
frank.hampel@fau.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H12 N2 O S'
_chemical_formula_sum            'C23 H12 N2 O S'
_chemical_formula_weight         364.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H12 N3 O S'
_chemical_oxdiff_usercomment     MZ-214
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   12.1913(2)
_cell_length_b                   22.6255(3)
_cell_length_c                   13.0947(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.3090(10)
_cell_angle_gamma                90
_cell_volume                     3582.62(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7108
_cell_measurement_temperature    153.00(10)
_cell_measurement_theta_max      73.0140
_cell_measurement_theta_min      4.1270
_shelx_estimated_absorpt_T_max   0.650
_shelx_estimated_absorpt_T_min   0.539
_exptl_absorpt_coefficient_mu    1.718
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -15 0 0.1918
4 -2 7 0.1723
3 6 6 0.1862
2 13 4 0.1894
-4 -3 -7 0.1639
-3 -9 -5 0.1575
5 -12 0 0.1073
-4 6 7 0.1235
-1 6 -7 0.1942
3 -3 -8 0.1379
6 -3 5 0.1437
-6 -9 -1 0.1739
-7 -5 -3 0.1623
-3 9 -5 0.2035
3 13 -3 0.1803
6 9 1 0.1574
-3 -9 6 0.2145
6 -7 3 0.1378
8 -3 0 0.1232
6 6 -6 0.1410
-7 5 -1 0.1808
-8 -1 3 0.1474

_exptl_crystal_recrystallization_method 
'The material was recrystallised from MeOH by slow evaporation'
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.331
_exptl_crystal_size_min          0.274
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0855 -14.6860 0.0074 0.3254 0.6808 0.6562
3.7133 -2.0126 6.8445 -0.2307 -0.4885 0.8415
3.3989 5.9339 6.3448 -0.3868 -0.8147 0.4320
1.8549 12.6422 3.5591 -0.4235 -0.8891 -0.1733
-3.6310 -3.3224 -6.7470 0.3451 0.7277 -0.5927
-2.9156 -9.0284 -5.4829 0.4208 0.8850 -0.1992
4.8830 -11.5019 -0.0388 -0.2947 0.5448 0.7851
-3.9766 5.6151 7.0826 0.4764 -0.8752 0.0838
-1.0564 6.4062 -7.3551 -0.1831 0.3328 -0.9250
3.0190 -2.8500 -8.0329 -0.4507 0.8270 -0.3360
5.6475 -3.3066 4.8169 -0.4649 -0.2512 0.8490
-5.9152 -9.4662 -0.5598 0.8777 0.4776 0.0380
-6.6643 -5.1607 -2.5402 0.8225 0.4468 -0.3520
-3.1333 9.1998 -5.2276 0.0353 0.0171 -0.9992
2.7893 13.1176 -2.7382 -0.6755 -0.3688 -0.6385
5.9954 9.2206 0.6971 -0.8783 -0.4779 -0.0117
-2.8633 -8.6551 6.4807 0.6622 -0.1598 0.7321
5.9331 -7.3323 2.8447 -0.4477 0.1054 0.8879
7.7215 -3.0529 -0.4775 -0.8201 0.1952 0.5379
5.5235 6.0985 -5.6760 -0.8897 0.2136 -0.4036
-7.2052 5.0328 -0.9611 0.6854 -0.1626 -0.7098
-7.6380 -1.1452 3.1550 0.9636 -0.2302 -0.1356

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13496
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.191
_diffrn_reflns_theta_min         3.924
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      153.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2679
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -124.00 -96.00   1.00    1.00    --  -42.07 -99.00  60.00   28
  2  ω      6.00  70.00   1.00    1.00    --   42.07 -99.00 120.00   64
  3  ω     -4.00 116.00   1.00    1.00    --   42.07  19.00 -30.00  120
  4  ω     33.00 102.00   1.00    1.66    --  106.12 -61.00  60.00   69
  5  ω     81.00 123.00   1.00    1.66    --  106.12 -30.00   0.00   42
  6  ω     34.00  70.00   1.00    1.66    --  106.12 -30.00   0.00   36
  7  ω     85.00 174.00   1.00    1.66    --  106.12  61.00 -30.00   89
  8  ω     32.00 124.00   1.00    1.66    --  106.12 -45.00-180.00   92
  9  ω     78.00 160.00   1.00    1.66    --  106.12  30.00 -90.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1139093000
_diffrn_orient_matrix_UB_12      -0.0228099000
_diffrn_orient_matrix_UB_13      0.0213860000
_diffrn_orient_matrix_UB_21      0.0016217000
_diffrn_orient_matrix_UB_22      -0.0463891000
_diffrn_orient_matrix_UB_23      -0.0858882000
_diffrn_orient_matrix_UB_31      0.0570230000
_diffrn_orient_matrix_UB_32      -0.0443131000
_diffrn_orient_matrix_UB_33      0.0789831000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_special_details          'Two independend molecules in asym. unit'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6064
_reflns_number_total             6961
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.709
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.00036(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         6961
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.020
_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)+(0.0518P)²+2.4028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1164
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C22(H22), C23(H23), C25(H25),
 C26(H26), C32(H32), C33(H33), C35(H35), C36(H36), C14A(H14A), C15A(H15A),
 C16A(H16A), C17A(H17A), C22A(H22A), C23A(H23A), C25A(H25A), C26A(H26A),
 C32A(H32A), C33A(H33A), C35A(H35A), C36A(H36A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
S12 S 0.53871(5) 0.24376(2) 0.42398(4) 0.03327(14) Uani 1 1 d . . . . .
O54 O 0.53226(13) 0.41017(8) 0.47872(11) 0.0396(4) Uani 1 1 d . . . . .
N28 N 0.47617(16) 0.60452(8) 0.05478(15) 0.0382(4) Uani 1 1 d . . . . .
N38 N 0.30976(18) 0.12849(10) -0.07724(15) 0.0449(5) Uani 1 1 d . . . . .
C1 C 0.48294(15) 0.33536(8) 0.29035(14) 0.0225(4) Uani 1 1 d . . . . .
C11 C 0.51718(15) 0.31915(8) 0.38862(14) 0.0241(4) Uani 1 1 d . . . . .
C13 C 0.55253(16) 0.26233(9) 0.55559(15) 0.0282(4) Uani 1 1 d . . . . .
C14 C 0.56575(18) 0.22082(10) 0.63429(16) 0.0328(4) Uani 1 1 d . . . . .
H14 H 0.567653 0.180606 0.619908 0.039 Uiso 1 1 calc R U . . .
C15 C 0.57599(18) 0.24102(11) 0.73457(16) 0.0358(5) Uani 1 1 d . . . . .
H15 H 0.585103 0.213937 0.788407 0.043 Uiso 1 1 calc R U . . .
C16 C 0.57292(18) 0.30126(11) 0.75668(15) 0.0350(5) Uani 1 1 d . . . . .
H16 H 0.580081 0.313842 0.824817 0.042 Uiso 1 1 calc R U . . .
C17 C 0.55930(16) 0.34240(10) 0.67798(15) 0.0313(4) Uani 1 1 d . . . . .
H17 H 0.557126 0.382580 0.692551 0.038 Uiso 1 1 calc R U . . .
C18 C 0.54889(16) 0.32257(9) 0.57637(14) 0.0269(4) Uani 1 1 d . . . . .
C19 C 0.53332(15) 0.36226(11) 0.48281(14) 0.0280(4) Uani 1 1 d . . . . .
C21 C 0.47973(16) 0.39751(8) 0.25362(14) 0.0229(4) Uani 1 1 d . . . . .
C22 C 0.57574(16) 0.43113(9) 0.25990(15) 0.0291(4) Uani 1 1 d . . . . .
H22 H 0.640380 0.417229 0.297610 0.035 Uiso 1 1 calc R U . . .
C23 C 0.57580(16) 0.48515(9) 0.21041(16) 0.0300(4) Uani 1 1 d . . . . .
H23 H 0.640768 0.506938 0.212889 0.036 Uiso 1 1 calc R U . . .
C24 C 0.47776(16) 0.50674(8) 0.15675(14) 0.0248(4) Uani 1 1 d . . . . .
C25 C 0.38025(16) 0.47486(9) 0.15487(16) 0.0291(4) Uani 1 1 d . . . . .
H25 H 0.314284 0.490280 0.122102 0.035 Uiso 1 1 calc R U . . .
C26 C 0.38152(16) 0.42026(9) 0.20173(16) 0.0280(4) Uani 1 1 d . . . . .
H26 H 0.316572 0.398418 0.198788 0.034 Uiso 1 1 calc R U . . .
C27 C 0.47716(17) 0.56145(9) 0.10029(15) 0.0286(4) Uani 1 1 d . . . . .
C31 C 0.44593(15) 0.29116(8) 0.20908(13) 0.0216(4) Uani 1 1 d . . . . .
C32 C 0.48351(16) 0.29401(9) 0.11271(14) 0.0252(4) Uani 1 1 d . . . . .
H32 H 0.532400 0.323712 0.099214 0.030 Uiso 1 1 calc R U . . .
C33 C 0.44834(16) 0.25281(9) 0.03697(14) 0.0271(4) Uani 1 1 d . . . . .
H33 H 0.473841 0.254652 -0.026939 0.033 Uiso 1 1 calc R U . . .
C34 C 0.37427(15) 0.20853(9) 0.05760(14) 0.0245(4) Uani 1 1 d . . . . .
C35 C 0.33423(16) 0.20656(9) 0.15249(14) 0.0266(4) Uani 1 1 d . . . . .
H35 H 0.284067 0.177415 0.165594 0.032 Uiso 1 1 calc R U . . .
C36 C 0.36912(16) 0.24794(9) 0.22710(14) 0.0253(4) Uani 1 1 d . . . . .
H36 H 0.341161 0.246982 0.289933 0.030 Uiso 1 1 calc R U . . .
C37 C 0.33809(17) 0.16442(10) -0.01840(15) 0.0310(4) Uani 1 1 d . . . . .
S12A S 0.26176(4) 0.23049(2) 0.72477(4) 0.02804(13) Uani 1 1 d . . . . .
O54A O 0.26342(14) 0.28190(7) 0.44376(11) 0.0379(4) Uani 1 1 d . . . . .
N28A N 0.19280(18) 0.56261(9) 0.27851(15) 0.0427(5) Uani 1 1 d . . . . .
N38A N 0.10068(16) 0.44699(9) 1.10172(14) 0.0377(4) Uani 1 1 d . . . . .
C1A C 0.21885(15) 0.34027(8) 0.63735(14) 0.0240(4) Uani 1 1 d . . . . .
C11A C 0.24651(16) 0.28357(9) 0.62392(14) 0.0250(4) Uani 1 1 d . . . . .
C13A C 0.28984(15) 0.17433(9) 0.63903(14) 0.0252(4) Uani 1 1 d . . . . .
C14A C 0.31506(17) 0.11614(9) 0.66778(16) 0.0302(4) Uani 1 1 d . . . . .
H14A H 0.319617 0.104305 0.736207 0.036 Uiso 1 1 calc R U . . .
C15A C 0.33308(18) 0.07658(9) 0.59128(17) 0.0328(5) Uani 1 1 d . . . . .
H15A H 0.349524 0.037477 0.608996 0.039 Uiso 1 1 calc R U . . .
C16A C 0.32739(17) 0.09341(9) 0.48865(16) 0.0309(4) Uani 1 1 d . . . . .
H16A H 0.338520 0.065577 0.438726 0.037 Uiso 1 1 calc R U . . .
C17A C 0.30526(16) 0.15135(9) 0.46092(15) 0.0275(4) Uani 1 1 d . . . . .
H17A H 0.302733 0.163139 0.392621 0.033 Uiso 1 1 calc R U . . .
C18A C 0.28669(15) 0.19210(8) 0.53698(14) 0.0246(4) Uani 1 1 d . . . . .
C19A C 0.26558(16) 0.25615(9) 0.52121(16) 0.0281(4) Uani 1 1 d . . . . .
C21A C 0.21100(15) 0.38599(8) 0.55395(14) 0.0238(4) Uani 1 1 d . . . . .
C22A C 0.12426(18) 0.38865(10) 0.47431(18) 0.0373(5) Uani 1 1 d . . . . .
H22A H 0.069434 0.359836 0.469255 0.045 Uiso 1 1 calc R U . . .
C23A C 0.11857(19) 0.43367(11) 0.40250(18) 0.0404(5) Uani 1 1 d . . . . .
H23A H 0.060051 0.435219 0.349560 0.049 Uiso 1 1 calc R U . . .
C24A C 0.20087(17) 0.47668(9) 0.40977(15) 0.0291(4) Uani 1 1 d . . . . .
C25A C 0.28862(19) 0.47406(10) 0.48766(17) 0.0369(5) Uani 1 1 d . . . . .
H25A H 0.344389 0.502335 0.491852 0.044 Uiso 1 1 calc R U . . .
C26A C 0.29261(18) 0.42883(10) 0.55947(16) 0.0349(5) Uani 1 1 d . . . . .
H26A H 0.351207 0.427240 0.612324 0.042 Uiso 1 1 calc R U . . .
C27A C 0.19555(19) 0.52435(9) 0.33594(16) 0.0342(5) Uani 1 1 d . . . . .
C31A C 0.19504(16) 0.36317(8) 0.73901(14) 0.0235(4) Uani 1 1 d . . . . .
C32A C 0.09624(17) 0.39320(9) 0.74504(15) 0.0296(4) Uani 1 1 d . . . . .
H32A H 0.046868 0.398925 0.685645 0.036 Uiso 1 1 calc R U . . .
C33A C 0.07056(17) 0.41461(9) 0.83802(15) 0.0300(4) Uani 1 1 d . . . . .
H33A H 0.004040 0.434167 0.841512 0.036 Uiso 1 1 calc R U . . .
C34A C 0.14590(16) 0.40648(8) 0.92671(14) 0.0252(4) Uani 1 1 d . . . . .
C35A C 0.24571(16) 0.37738(9) 0.92172(15) 0.0276(4) Uani 1 1 d . . . . .
H35A H 0.295887 0.372463 0.980810 0.033 Uiso 1 1 calc R U . . .
C36A C 0.26971(16) 0.35582(9) 0.82814(15) 0.0272(4) Uani 1 1 d . . . . .
H36A H 0.336210 0.336251 0.824627 0.033 Uiso 1 1 calc R U . . .
C37A C 0.12012(16) 0.42888(9) 1.02391(15) 0.0285(4) 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
S12 C11 1.7781(19) . ?
S12 C13 1.761(2) . ?
O54 C19 1.085(3) . ?
N28 C27 1.141(3) . ?
N38 C37 1.143(3) . ?
C1 C11 1.352(3) . ?
C1 C21 1.485(2) . ?
C1 C31 1.488(2) . ?
C11 C19 1.565(3) . ?
C13 C14 1.389(3) . ?
C13 C18 1.392(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.395(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.394(3) . ?
C18 C19 1.511(3) . ?
C21 C22 1.390(3) . ?
C21 C26 1.398(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.383(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.395(3) . ?
C24 C25 1.388(3) . ?
C24 C27 1.441(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.378(3) . ?
C26 H26 0.9300 . ?
C31 C32 1.398(3) . ?
C31 C36 1.395(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.389(3) . ?
C33 H33 0.9300 . ?
C33 C34 1.398(3) . ?
C34 C35 1.392(3) . ?
C34 C37 1.439(3) . ?
C35 H35 0.9300 . ?
C35 C36 1.381(3) . ?
C36 H36 0.9300 . ?
S12A C11A 1.7771(19) . ?
S12A C13A 1.7577(19) . ?
O54A C19A 1.167(3) . ?
N28A C27A 1.144(3) . ?
N38A C37A 1.150(3) . ?
C1A C11A 1.344(3) . ?
C1A C21A 1.498(3) . ?
C1A C31A 1.491(3) . ?
C11A C19A 1.526(3) . ?
C13A C14A 1.393(3) . ?
C13A C18A 1.391(3) . ?
C14A H14A 0.9300 . ?
C14A C15A 1.382(3) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.390(3) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.378(3) . ?
C17A H17A 0.9300 . ?
C17A C18A 1.397(3) . ?
C18A C19A 1.482(3) . ?
C21A C22A 1.389(3) . ?
C21A C26A 1.384(3) . ?
C22A H22A 0.9300 . ?
C22A C23A 1.382(3) . ?
C23A H23A 0.9300 . ?
C23A C24A 1.392(3) . ?
C24A C25A 1.382(3) . ?
C24A C27A 1.444(3) . ?
C25A H25A 0.9300 . ?
C25A C26A 1.386(3) . ?
C26A H26A 0.9300 . ?
C31A C32A 1.394(3) . ?
C31A C36A 1.396(3) . ?
C32A H32A 0.9300 . ?
C32A C33A 1.383(3) . ?
C33A H33A 0.9300 . ?
C33A C34A 1.398(3) . ?
C34A C35A 1.392(3) . ?
C34A C37A 1.441(3) . ?
C35A H35A 0.9300 . ?
C35A C36A 1.384(3) . ?
C36A H36A 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
C13 S12 C11 91.06(9) . . ?
C11 C1 C21 123.88(17) . . ?
C11 C1 C31 121.81(17) . . ?
C21 C1 C31 114.31(15) . . ?
C1 C11 S12 121.71(14) . . ?
C1 C11 C19 125.00(17) . . ?
C19 C11 S12 113.14(14) . . ?
C14 C13 S12 123.55(17) . . ?
C14 C13 C18 121.39(18) . . ?
C18 C13 S12 115.06(15) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 C13 118.0(2) . . ?
C15 C14 H14 121.0 . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.3(2) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.45(19) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.8(2) . . ?
C18 C17 H17 120.6 . . ?
C13 C18 C17 120.03(19) . . ?
C13 C18 C19 115.29(18) . . ?
C17 C18 C19 124.68(19) . . ?
O54 C19 C11 125.74(18) . . ?
O54 C19 C18 129.3(2) . . ?
C18 C19 C11 105.00(18) . . ?
C22 C21 C1 120.79(17) . . ?
C22 C21 C26 119.35(17) . . ?
C26 C21 C1 119.47(17) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.44(18) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.2 . . ?
C22 C23 C24 119.59(18) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 C27 120.47(18) . . ?
C25 C24 C23 120.24(18) . . ?
C25 C24 C27 119.26(18) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 C24 119.79(18) . . ?
C26 C25 H25 120.1 . . ?
C21 C26 H26 119.8 . . ?
C25 C26 C21 120.45(18) . . ?
C25 C26 H26 119.8 . . ?
N28 C27 C24 179.4(2) . . ?
C32 C31 C1 120.69(17) . . ?
C36 C31 C1 119.95(16) . . ?
C36 C31 C32 119.30(17) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 C31 120.46(18) . . ?
C33 C32 H32 119.8 . . ?
C32 C33 H33 120.3 . . ?
C32 C33 C34 119.43(17) . . ?
C34 C33 H33 120.3 . . ?
C33 C34 C37 120.82(17) . . ?
C35 C34 C33 120.26(17) . . ?
C35 C34 C37 118.92(18) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 C34 119.89(18) . . ?
C36 C35 H35 120.1 . . ?
C31 C36 H36 119.7 . . ?
C35 C36 C31 120.58(17) . . ?
C35 C36 H36 119.7 . . ?
N38 C37 C34 178.6(2) . . ?
C13A S12A C11A 91.39(9) . . ?
C11A C1A C21A 123.89(17) . . ?
C11A C1A C31A 121.95(17) . . ?
C31A C1A C21A 114.15(16) . . ?
C1A C11A S12A 123.52(15) . . ?
C1A C11A C19A 124.92(18) . . ?
C19A C11A S12A 111.54(14) . . ?
C14A C13A S12A 124.39(15) . . ?
C18A C13A S12A 114.89(15) . . ?
C18A C13A C14A 120.72(18) . . ?
C13A C14A H14A 121.1 . . ?
C15A C14A C13A 117.80(19) . . ?
C15A C14A H14A 121.1 . . ?
C14A C15A H15A 119.0 . . ?
C14A C15A C16A 122.04(19) . . ?
C16A C15A H15A 119.0 . . ?
C15A C16A H16A 120.0 . . ?
C17A C16A C15A 119.97(18) . . ?
C17A C16A H16A 120.0 . . ?
C16A C17A H17A 120.5 . . ?
C16A C17A C18A 118.96(18) . . ?
C18A C17A H17A 120.5 . . ?
C13A C18A C17A 120.47(18) . . ?
C13A C18A C19A 113.54(17) . . ?
C17A C18A C19A 125.97(18) . . ?
O54A C19A C11A 125.03(19) . . ?
O54A C19A C18A 126.42(18) . . ?
C18A C19A C11A 108.55(17) . . ?
C22A C21A C1A 123.31(17) . . ?
C26A C21A C1A 117.81(17) . . ?
C26A C21A C22A 118.84(18) . . ?
C21A C22A H22A 119.7 . . ?
C23A C22A C21A 120.7(2) . . ?
C23A C22A H22A 119.7 . . ?
C22A C23A H23A 120.2 . . ?
C22A C23A C24A 119.7(2) . . ?
C24A C23A H23A 120.2 . . ?
C23A C24A C27A 120.37(19) . . ?
C25A C24A C23A 120.25(19) . . ?
C25A C24A C27A 119.38(19) . . ?
C24A C25A H25A 120.4 . . ?
C24A C25A C26A 119.3(2) . . ?
C26A C25A H25A 120.4 . . ?
C21A C26A C25A 121.23(19) . . ?
C21A C26A H26A 119.4 . . ?
C25A C26A H26A 119.4 . . ?
N28A C27A C24A 178.8(3) . . ?
C32A C31A C1A 119.19(17) . . ?
C32A C31A C36A 119.15(17) . . ?
C36A C31A C1A 121.65(17) . . ?
C31A C32A H32A 119.5 . . ?
C33A C32A C31A 120.98(18) . . ?
C33A C32A H32A 119.5 . . ?
C32A C33A H33A 120.4 . . ?
C32A C33A C34A 119.14(18) . . ?
C34A C33A H33A 120.4 . . ?
C33A C34A C37A 119.55(18) . . ?
C35A C34A C33A 120.59(18) . . ?
C35A C34A C37A 119.86(18) . . ?
C34A C35A H35A 120.2 . . ?
C36A C35A C34A 119.51(18) . . ?
C36A C35A H35A 120.2 . . ?
C31A C36A H36A 119.7 . . ?
C35A C36A C31A 120.62(18) . . ?
C35A C36A H36A 119.7 . . ?
N38A C37A C34A 179.3(2) . . ?

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
S12 C11 C19 O54 173.66(19) . . . . ?
S12 C11 C19 C18 -6.84(18) . . . . ?
S12 C13 C14 C15 179.84(16) . . . . ?
S12 C13 C18 C17 -179.83(15) . . . . ?
S12 C13 C18 C19 0.2(2) . . . . ?
C1 C11 C19 O54 -10.7(3) . . . . ?
C1 C11 C19 C18 168.75(18) . . . . ?
C1 C21 C22 C23 169.13(18) . . . . ?
C1 C21 C26 C25 -171.19(18) . . . . ?
C1 C31 C32 C33 -179.72(17) . . . . ?
C1 C31 C36 C35 -179.84(17) . . . . ?
C11 S12 C13 C14 175.97(18) . . . . ?
C11 S12 C13 C18 -3.79(16) . . . . ?
C11 C1 C21 C22 60.7(3) . . . . ?
C11 C1 C21 C26 -126.5(2) . . . . ?
C11 C1 C31 C32 -133.8(2) . . . . ?
C11 C1 C31 C36 49.1(3) . . . . ?
C13 S12 C11 C1 -169.54(17) . . . . ?
C13 S12 C11 C19 6.21(14) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C13 C18 C19 O54 -176.4(2) . . . . ?
C13 C18 C19 C11 4.2(2) . . . . ?
C14 C13 C18 C17 0.4(3) . . . . ?
C14 C13 C18 C19 -179.58(18) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C16 C17 C18 C13 -0.1(3) . . . . ?
C16 C17 C18 C19 179.84(18) . . . . ?
C17 C18 C19 O54 3.6(3) . . . . ?
C17 C18 C19 C11 -175.82(18) . . . . ?
C18 C13 C14 C15 -0.4(3) . . . . ?
C21 C1 C11 S12 -170.49(14) . . . . ?
C21 C1 C11 C19 14.3(3) . . . . ?
C21 C1 C31 C32 45.6(2) . . . . ?
C21 C1 C31 C36 -131.44(18) . . . . ?
C21 C22 C23 C24 2.1(3) . . . . ?
C22 C21 C26 C25 1.7(3) . . . . ?
C22 C23 C24 C25 1.4(3) . . . . ?
C22 C23 C24 C27 -176.81(19) . . . . ?
C23 C24 C25 C26 -3.4(3) . . . . ?
C24 C25 C26 C21 1.8(3) . . . . ?
C26 C21 C22 C23 -3.6(3) . . . . ?
C27 C24 C25 C26 174.87(18) . . . . ?
C31 C1 C11 S12 8.9(3) . . . . ?
C31 C1 C11 C19 -166.34(17) . . . . ?
C31 C1 C21 C22 -118.7(2) . . . . ?
C31 C1 C21 C26 54.1(2) . . . . ?
C31 C32 C33 C34 0.4(3) . . . . ?
C32 C31 C36 C35 3.0(3) . . . . ?
C32 C33 C34 C35 1.4(3) . . . . ?
C32 C33 C34 C37 -178.65(18) . . . . ?
C33 C34 C35 C36 -1.0(3) . . . . ?
C34 C35 C36 C31 -1.2(3) . . . . ?
C36 C31 C32 C33 -2.6(3) . . . . ?
C37 C34 C35 C36 179.05(18) . . . . ?
S12A C11A C19A O54A -177.78(18) . . . . ?
S12A C11A C19A C18A 2.36(19) . . . . ?
S12A C13A C14A C15A 178.74(16) . . . . ?
S12A C13A C18A C17A -178.65(15) . . . . ?
S12A C13A C18A C19A 2.9(2) . . . . ?
C1A C11A C19A O54A 3.8(3) . . . . ?
C1A C11A C19A C18A -176.06(18) . . . . ?
C1A C21A C22A C23A 176.7(2) . . . . ?
C1A C21A C26A C25A -177.3(2) . . . . ?
C1A C31A C32A C33A 179.36(19) . . . . ?
C1A C31A C36A C35A -179.90(18) . . . . ?
C11A S12A C13A C14A 178.00(18) . . . . ?
C11A S12A C13A C18A -1.21(16) . . . . ?
C11A C1A C21A C22A 74.7(3) . . . . ?
C11A C1A C21A C26A -107.8(2) . . . . ?
C11A C1A C31A C32A -127.2(2) . . . . ?
C11A C1A C31A C36A 53.5(3) . . . . ?
C13A S12A C11A C1A 177.70(18) . . . . ?
C13A S12A C11A C19A -0.75(14) . . . . ?
C13A C14A C15A C16A 0.4(3) . . . . ?
C13A C18A C19A O54A 176.9(2) . . . . ?
C13A C18A C19A C11A -3.3(2) . . . . ?
C14A C13A C18A C17A 2.1(3) . . . . ?
C14A C13A C18A C19A -176.34(18) . . . . ?
C14A C15A C16A C17A 1.3(3) . . . . ?
C15A C16A C17A C18A -1.3(3) . . . . ?
C16A C17A C18A C13A -0.4(3) . . . . ?
C16A C17A C18A C19A 177.85(18) . . . . ?
C17A C18A C19A O54A -1.5(3) . . . . ?
C17A C18A C19A C11A 178.36(18) . . . . ?
C18A C13A C14A C15A -2.1(3) . . . . ?
C21A C1A C11A S12A 177.01(14) . . . . ?
C21A C1A C11A C19A -4.8(3) . . . . ?
C21A C1A C31A C32A 53.8(2) . . . . ?
C21A C1A C31A C36A -125.53(19) . . . . ?
C21A C22A C23A C24A 0.3(4) . . . . ?
C22A C21A C26A C25A 0.4(3) . . . . ?
C22A C23A C24A C25A 0.8(4) . . . . ?
C22A C23A C24A C27A -179.4(2) . . . . ?
C23A C24A C25A C26A -1.2(3) . . . . ?
C24A C25A C26A C21A 0.7(4) . . . . ?
C26A C21A C22A C23A -0.8(3) . . . . ?
C27A C24A C25A C26A 178.9(2) . . . . ?
C31A C1A C11A S12A -1.9(3) . . . . ?
C31A C1A C11A C19A 176.34(17) . . . . ?
C31A C1A C21A C22A -106.3(2) . . . . ?
C31A C1A C21A C26A 71.2(2) . . . . ?
C31A C32A C33A C34A 0.8(3) . . . . ?
C32A C31A C36A C35A 0.8(3) . . . . ?
C32A C33A C34A C35A 0.2(3) . . . . ?
C32A C33A C34A C37A 179.71(19) . . . . ?
C33A C34A C35A C36A -0.7(3) . . . . ?
C34A C35A C36A C31A 0.2(3) . . . . ?
C36A C31A C32A C33A -1.3(3) . . . . ?
C37A C34A C35A C36A 179.78(18) . . . . ?


_olex2_date_sample_data_collection 2009-06-05
_olex2_diffrn_ambient_temperature_device 'Cryojet - Oxford Instruments'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a mylar loop in perfluoroether oil'
_olex2_submission_original_sample_id MZ214
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.326
_oxdiff_exptl_absorpt_empirical_full_min 0.751
