# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_nme-7
_database_code_depnum_ccdc_archive 'CCDC 2194368'
loop_
_audit_author_name
_audit_author_address
ff
;werwerf
China
;
_audit_update_record             
;
2022-08-02 deposited with the CCDC.	2023-02-16 downloaded from the CCDC.
;
_audit_creation_date             2022-06-01
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 N4 O S, C H4 O'
_chemical_formula_sum            'C23 H24 N4 O2 S'
_chemical_formula_weight         420.52
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   16.1900(3)
_cell_length_b                   9.48160(10)
_cell_length_c                   14.9584(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.201(2)
_cell_angle_gamma                90
_cell_volume                     2110.52(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7795
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      71.2560
_cell_measurement_theta_min      2.9760
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.583
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10488
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.383
_diffrn_reflns_theta_min         2.970
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     80.00 131.00   0.50    0.50    --   42.30  77.00-150.00  102
  2  ω    -30.00  -4.00   0.50    0.50    --   42.30 -57.00 150.00   52
  3  ω    -37.00  14.00   0.50    0.50    --   42.30 -77.00 -60.00  102
  4  ω      5.00  75.00   0.50    0.50    --   42.30 -82.00  60.00  140
  5  ω    -33.00  39.00   0.50    0.50    --   42.30 -82.00-180.00  144
  6  ω     18.00  61.00   0.50    0.50    --   42.30 -57.00 150.00   86
  7  ω     32.00  57.00   0.50    0.50    --   42.30 -77.00 -60.00   50
  8  ω     70.00 128.00   0.50    0.50    --  101.60  50.00-120.00  116
  9  ω    118.00 145.00   0.50    0.50    --  101.60 -82.00  60.00   54
 10  ω     12.00 134.00   0.50    0.50    --  101.60 -63.00  60.00  244
 11  ω     94.00 135.00   0.50    0.50    --  101.60 -82.00  90.00   82
 12  ω     40.00 114.00   0.50    0.50    --  101.60 -82.00  60.00  148
 13  ω     92.00 169.00   0.50    0.50    --  101.60  50.00-150.00  154
 14  ω     18.00 127.00   0.50    0.50    --  101.60 -50.00-120.00  218
 15  ω     16.00 128.00   0.50    0.50    --  101.60 -38.00-120.00  224
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0737084000
_diffrn_orient_matrix_UB_12      0.1061494000
_diffrn_orient_matrix_UB_13      -0.0578315000
_diffrn_orient_matrix_UB_21      -0.0703080000
_diffrn_orient_matrix_UB_22      -0.1192230000
_diffrn_orient_matrix_UB_23      -0.0283220000
_diffrn_orient_matrix_UB_31      -0.0184451000
_diffrn_orient_matrix_UB_32      0.0302126000
_diffrn_orient_matrix_UB_33      0.0916870000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3803
_reflns_number_total             4017
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4017
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0394
_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)+(0.0561P)²+1.0682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1073
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), C11(H11), C12(H12), C13(H13), C14(H14), C21(H21), C22(H22), C23(H23),
 C24(H24)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C28(H28A,H28B,H28C), C30(H30A,H30B,H30C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2A)
;
_atom_sites_solution_hydrogens   mixed
_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
S1 S 0.10916(3) 0.64125(4) 0.62553(3) 0.03135(13) Uani 1 1 d . . . . .
O1 O 0.19377(8) 0.25907(12) 0.53188(8) 0.0352(3) Uani 1 1 d . . . . .
N1 N 0.16053(9) 0.21628(14) 0.36974(9) 0.0289(3) Uani 1 1 d . . . . .
N2 N 0.09159(9) 0.52181(14) 0.45516(9) 0.0270(3) Uani 1 1 d . . . . .
N3 N 0.22831(9) 0.59233(14) 0.54352(9) 0.0290(3) Uani 1 1 d . . . . .
N4 N 0.34272(9) 0.39604(15) 0.40871(10) 0.0330(3) Uani 1 1 d . . . . .
H4 H 0.315117 0.401682 0.346556 0.040 Uiso 1 1 calc R U . . .
C1 C 0.14527(10) 0.45130(16) 0.41054(10) 0.0249(3) Uani 1 1 d . . . . .
C2 C 0.23321(10) 0.54488(17) 0.45128(10) 0.0277(3) Uani 1 1 d . . . . .
C3 C 0.31814(10) 0.46280(17) 0.47650(11) 0.0296(3) Uani 1 1 d . . . . .
C4 C 0.37815(11) 0.43298(18) 0.56840(12) 0.0321(3) Uani 1 1 d . . . . .
C5 C 0.36902(11) 0.49192(19) 0.65705(12) 0.0367(4) Uani 1 1 d . . . . .
H5A H 0.427825 0.515695 0.705696 0.044 Uiso 1 1 calc R U . . .
H5B H 0.341910 0.422262 0.684582 0.044 Uiso 1 1 calc R U . . .
C6 C 0.31020(11) 0.62360(18) 0.62823(12) 0.0345(4) Uani 1 1 d . . . . .
H6A H 0.295034 0.653524 0.681914 0.041 Uiso 1 1 calc R U . . .
H6B H 0.342655 0.699626 0.613081 0.041 Uiso 1 1 calc R U . . .
C8 C 0.14475(10) 0.58256(16) 0.54080(11) 0.0272(3) Uani 1 1 d . . . . .
C10 C 0.11822(10) 0.29177(16) 0.28209(11) 0.0265(3) Uani 1 1 d . . . . .
C11 C 0.08940(11) 0.24081(18) 0.18837(11) 0.0331(3) Uani 1 1 d . . . . .
H11 H 0.101144 0.148565 0.175763 0.040 Uiso 1 1 calc R U . . .
C12 C 0.04196(12) 0.33336(19) 0.11341(11) 0.0364(4) Uani 1 1 d . . . . .
H12 H 0.021192 0.302030 0.049379 0.044 Uiso 1 1 calc R U . . .
C13 C 0.02504(12) 0.47097(19) 0.13209(11) 0.0364(4) Uani 1 1 d . . . . .
H13 H -0.007251 0.530382 0.080697 0.044 Uiso 1 1 calc R U . . .
C14 C 0.05597(11) 0.52131(17) 0.22728(11) 0.0310(3) Uani 1 1 d . . . . .
H14 H 0.044927 0.613897 0.239907 0.037 Uiso 1 1 calc R U . . .
C15 C 0.10327(9) 0.43103(16) 0.30235(10) 0.0252(3) Uani 1 1 d . . . . .
C16 C 0.16962(10) 0.29753(16) 0.44767(11) 0.0272(3) Uani 1 1 d . . . . .
C19 C 0.19112(13) 0.07090(18) 0.37630(14) 0.0412(4) Uani 1 1 d . . . . .
H19A H 0.243637 0.066628 0.361508 0.062 Uiso 1 1 calc R U . . .
H19B H 0.144453 0.013935 0.330718 0.062 Uiso 1 1 calc R U . . .
H19C H 0.205470 0.036211 0.440995 0.062 Uiso 1 1 calc R U . . .
C20 C 0.41926(10) 0.31878(18) 0.45820(12) 0.0334(4) Uani 1 1 d . . . . .
C21 C 0.46794(12) 0.2302(2) 0.42239(14) 0.0402(4) Uani 1 1 d . . . . .
H21 H 0.452392 0.219358 0.355933 0.048 Uiso 1 1 calc R U . . .
C22 C 0.54024(12) 0.1594(2) 0.48982(16) 0.0450(4) Uani 1 1 d . . . . .
H22 H 0.573658 0.099065 0.468021 0.054 Uiso 1 1 calc R U . . .
C23 C 0.56452(12) 0.1756(2) 0.58954(15) 0.0444(4) Uani 1 1 d . . . . .
H23 H 0.613159 0.125317 0.632800 0.053 Uiso 1 1 calc R U . . .
C24 C 0.51760(11) 0.26503(19) 0.62496(13) 0.0395(4) Uani 1 1 d . . . . .
H24 H 0.534731 0.276313 0.691630 0.047 Uiso 1 1 calc R U . . .
C25 C 0.44337(11) 0.33909(18) 0.55894(12) 0.0332(3) Uani 1 1 d . . . . .
C28 C 0.22655(12) 0.67302(18) 0.38697(12) 0.0360(4) Uani 1 1 d . . . . .
H28A H 0.170332 0.720128 0.372956 0.054 Uiso 1 1 calc R U . . .
H28B H 0.230016 0.642843 0.327283 0.054 Uiso 1 1 calc R U . . .
H28C H 0.275122 0.736639 0.420240 0.054 Uiso 1 1 calc R U . . .
O2 O 0.28626(11) 0.11525(19) 0.70601(10) 0.0620(4) Uani 1 1 d . . . . .
H2A H 0.246734 0.156230 0.661148 0.093 Uiso 1 1 calc R U . . .
C30 C 0.3335(3) 0.0305(4) 0.6697(2) 0.1017(13) Uani 1 1 d . . . . .
H30A H 0.296192 -0.046478 0.634819 0.153 Uiso 1 1 calc R U . . .
H30B H 0.385422 -0.005782 0.722248 0.153 Uiso 1 1 calc R U . . .
H30C H 0.352259 0.083938 0.626494 0.153 Uiso 1 1 calc R U . . .
H2 H 0.0393(13) 0.489(2) 0.4442(13) 0.031(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C8 1.6802(15) . ?
O1 C16 1.2184(18) . ?
N1 C10 1.4117(19) . ?
N1 C16 1.356(2) . ?
N1 C19 1.455(2) . ?
N2 C1 1.4509(19) . ?
N2 C8 1.3583(19) . ?
N2 H2 0.86(2) . ?
N3 C2 1.4828(19) . ?
N3 C6 1.4587(19) . ?
N3 C8 1.341(2) . ?
N4 H4 0.8600 . ?
N4 C3 1.380(2) . ?
N4 C20 1.378(2) . ?
C1 C2 1.582(2) . ?
C1 C15 1.5004(19) . ?
C1 C16 1.555(2) . ?
C2 C3 1.493(2) . ?
C2 C28 1.527(2) . ?
C3 C4 1.364(2) . ?
C4 C5 1.499(2) . ?
C4 C25 1.430(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.526(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C10 C11 1.379(2) . ?
C10 C15 1.397(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.392(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.394(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.395(2) . ?
C20 C25 1.413(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.382(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.393(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.376(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.406(2) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
O2 H2A 0.8200 . ?
O2 C30 1.361(3) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 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
C10 N1 C19 124.81(13) . . ?
C16 N1 C10 111.03(13) . . ?
C16 N1 C19 124.16(14) . . ?
C1 N2 H2 118.0(13) . . ?
C8 N2 C1 110.95(12) . . ?
C8 N2 H2 123.2(12) . . ?
C6 N3 C2 120.43(13) . . ?
C8 N3 C2 111.97(12) . . ?
C8 N3 C6 126.97(13) . . ?
C3 N4 H4 126.0 . . ?
C20 N4 H4 126.0 . . ?
C20 N4 C3 107.92(13) . . ?
N2 C1 C2 100.12(11) . . ?
N2 C1 C15 117.14(12) . . ?
N2 C1 C16 112.41(12) . . ?
C15 C1 C2 116.37(12) . . ?
C15 C1 C16 102.04(12) . . ?
C16 C1 C2 108.99(12) . . ?
N3 C2 C1 99.13(11) . . ?
N3 C2 C3 107.73(12) . . ?
N3 C2 C28 109.18(13) . . ?
C3 C2 C1 113.85(13) . . ?
C3 C2 C28 113.78(13) . . ?
C28 C2 C1 111.97(12) . . ?
N4 C3 C2 123.83(13) . . ?
C4 C3 N4 110.39(14) . . ?
C4 C3 C2 125.57(14) . . ?
C3 C4 C5 122.34(15) . . ?
C3 C4 C25 106.83(14) . . ?
C25 C4 C5 130.81(15) . . ?
C4 C5 H5A 109.9 . . ?
C4 C5 H5B 109.9 . . ?
C4 C5 C6 108.86(14) . . ?
H5A C5 H5B 108.3 . . ?
C6 C5 H5A 109.9 . . ?
C6 C5 H5B 109.9 . . ?
N3 C6 C5 109.36(13) . . ?
N3 C6 H6A 109.8 . . ?
N3 C6 H6B 109.8 . . ?
C5 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
N2 C8 S1 125.01(12) . . ?
N3 C8 S1 126.59(12) . . ?
N3 C8 N2 108.35(13) . . ?
C11 C10 N1 127.78(14) . . ?
C11 C10 C15 122.25(14) . . ?
C15 C10 N1 109.87(13) . . ?
C10 C11 H11 121.4 . . ?
C10 C11 C12 117.15(15) . . ?
C12 C11 H11 121.4 . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.45(15) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.58(15) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.7 . . ?
C15 C14 C13 118.67(15) . . ?
C15 C14 H14 120.7 . . ?
C10 C15 C1 108.14(13) . . ?
C14 C15 C1 131.98(14) . . ?
C14 C15 C10 119.87(14) . . ?
O1 C16 N1 126.91(15) . . ?
O1 C16 C1 125.66(14) . . ?
N1 C16 C1 107.42(12) . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N4 C20 C21 129.68(16) . . ?
N4 C20 C25 108.23(14) . . ?
C21 C20 C25 122.08(16) . . ?
C20 C21 H21 121.4 . . ?
C22 C21 C20 117.17(17) . . ?
C22 C21 H21 121.4 . . ?
C21 C22 H22 119.1 . . ?
C21 C22 C23 121.89(18) . . ?
C23 C22 H22 119.1 . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 120.98(17) . . ?
C24 C23 H23 119.5 . . ?
C23 C24 H24 120.5 . . ?
C23 C24 C25 119.06(17) . . ?
C25 C24 H24 120.5 . . ?
C20 C25 C4 106.61(14) . . ?
C24 C25 C4 134.53(16) . . ?
C24 C25 C20 118.79(16) . . ?
C2 C28 H28A 109.5 . . ?
C2 C28 H28B 109.5 . . ?
C2 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 O2 H2A 109.5 . . ?
O2 C30 H30A 109.5 . . ?
O2 C30 H30B 109.5 . . ?
O2 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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
N1 C10 C11 C12 174.31(15) . . . . ?
N1 C10 C15 C1 4.82(16) . . . . ?
N1 C10 C15 C14 -174.74(13) . . . . ?
N2 C1 C2 N3 28.13(13) . . . . ?
N2 C1 C2 C3 142.23(12) . . . . ?
N2 C1 C2 C28 -86.93(14) . . . . ?
N2 C1 C15 C10 -133.26(14) . . . . ?
N2 C1 C15 C14 46.2(2) . . . . ?
N2 C1 C16 O1 -42.5(2) . . . . ?
N2 C1 C16 N1 138.57(13) . . . . ?
N3 C2 C3 N4 176.50(14) . . . . ?
N3 C2 C3 C4 2.3(2) . . . . ?
N4 C3 C4 C5 179.56(15) . . . . ?
N4 C3 C4 C25 -1.55(19) . . . . ?
N4 C20 C21 C22 -176.57(17) . . . . ?
N4 C20 C25 C4 -0.30(18) . . . . ?
N4 C20 C25 C24 177.02(15) . . . . ?
C1 N2 C8 S1 -165.37(11) . . . . ?
C1 N2 C8 N3 17.14(17) . . . . ?
C1 C2 C3 N4 67.62(19) . . . . ?
C1 C2 C3 C4 -106.58(17) . . . . ?
C2 N3 C6 C5 -59.77(19) . . . . ?
C2 N3 C8 S1 -173.14(11) . . . . ?
C2 N3 C8 N2 4.30(17) . . . . ?
C2 C1 C15 C10 108.42(15) . . . . ?
C2 C1 C15 C14 -72.1(2) . . . . ?
C2 C1 C16 O1 67.53(18) . . . . ?
C2 C1 C16 N1 -111.38(13) . . . . ?
C2 C3 C4 C5 -5.6(3) . . . . ?
C2 C3 C4 C25 173.31(15) . . . . ?
C3 N4 C20 C21 177.74(17) . . . . ?
C3 N4 C20 C25 -0.63(18) . . . . ?
C3 C4 C5 C6 -21.4(2) . . . . ?
C3 C4 C25 C20 1.12(18) . . . . ?
C3 C4 C25 C24 -175.59(18) . . . . ?
C4 C5 C6 N3 49.58(18) . . . . ?
C5 C4 C25 C20 179.89(17) . . . . ?
C5 C4 C25 C24 3.2(3) . . . . ?
C6 N3 C2 C1 150.43(14) . . . . ?
C6 N3 C2 C3 31.65(19) . . . . ?
C6 N3 C2 C28 -92.36(17) . . . . ?
C6 N3 C8 S1 16.0(2) . . . . ?
C6 N3 C8 N2 -166.56(15) . . . . ?
C8 N2 C1 C2 -29.04(15) . . . . ?
C8 N2 C1 C15 -155.80(13) . . . . ?
C8 N2 C1 C16 86.49(15) . . . . ?
C8 N3 C2 C1 -21.10(16) . . . . ?
C8 N3 C2 C3 -139.88(13) . . . . ?
C8 N3 C2 C28 96.10(15) . . . . ?
C8 N3 C6 C5 110.40(18) . . . . ?
C10 N1 C16 O1 170.97(14) . . . . ?
C10 N1 C16 C1 -10.14(16) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C10 C15 C1 -178.52(14) . . . . ?
C11 C10 C15 C14 1.9(2) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C14 C15 C1 179.73(15) . . . . ?
C13 C14 C15 C10 -0.8(2) . . . . ?
C15 C1 C2 N3 155.41(13) . . . . ?
C15 C1 C2 C3 -90.49(16) . . . . ?
C15 C1 C2 C28 40.34(18) . . . . ?
C15 C1 C16 O1 -168.85(14) . . . . ?
C15 C1 C16 N1 12.23(15) . . . . ?
C15 C10 C11 C12 -1.7(2) . . . . ?
C16 N1 C10 C11 -172.80(15) . . . . ?
C16 N1 C10 C15 3.63(17) . . . . ?
C16 C1 C2 N3 -89.96(13) . . . . ?
C16 C1 C2 C3 24.14(16) . . . . ?
C16 C1 C2 C28 154.97(13) . . . . ?
C16 C1 C15 C10 -10.08(15) . . . . ?
C16 C1 C15 C14 169.41(16) . . . . ?
C19 N1 C10 C11 7.6(3) . . . . ?
C19 N1 C10 C15 -175.96(15) . . . . ?
C19 N1 C16 O1 -9.4(3) . . . . ?
C19 N1 C16 C1 169.45(14) . . . . ?
C20 N4 C3 C2 -173.59(14) . . . . ?
C20 N4 C3 C4 1.38(19) . . . . ?
C20 C21 C22 C23 -0.5(3) . . . . ?
C21 C20 C25 C4 -178.81(16) . . . . ?
C21 C20 C25 C24 -1.5(2) . . . . ?
C21 C22 C23 C24 -0.8(3) . . . . ?
C22 C23 C24 C25 0.9(3) . . . . ?
C23 C24 C25 C4 176.61(18) . . . . ?
C23 C24 C25 C20 0.2(3) . . . . ?
C25 C4 C5 C6 160.02(17) . . . . ?
C25 C20 C21 C22 1.6(3) . . . . ?
C28 C2 C3 N4 -62.3(2) . . . . ?
C28 C2 C3 C4 123.48(17) . . . . ?

_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 1.877
_oxdiff_exptl_absorpt_empirical_full_min 0.596
####################################################################### 
# 
# 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_mme-15_2
_database_code_depnum_ccdc_archive 'CCDC 2194369'
loop_
_audit_author_name
_audit_author_address
cvv
;rgr
China
;
_audit_update_record             
;
2022-08-02 deposited with the CCDC.	2023-02-16 downloaded from the CCDC.
;
_audit_creation_date             2022-06-02
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H26 N4 O S'
_chemical_formula_sum            'C25 H26 N4 O S'
_chemical_formula_weight         430.56
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C100 H96 Cl4 N16 O4 '
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                   13.01620(10)
_cell_length_b                   15.4077(2)
_cell_length_c                   11.23150(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.5160(10)
_cell_angle_gamma                90
_cell_volume                     2227.64(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12596
_cell_measurement_temperature    295.55(10)
_cell_measurement_theta_max      75.6130
_cell_measurement_theta_min      2.8950
_shelx_estimated_absorpt_T_max   0.854
_shelx_estimated_absorpt_T_min   0.820
_exptl_absorpt_coefficient_mu    1.478
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15536
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.652
_diffrn_reflns_theta_min         3.433
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.55(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  21.00   0.50    0.34    --  -43.18 100.00 172.00   50
  2  ω    -70.00 -44.00   0.50    0.34    --  -43.18 100.00 172.00   52
  3  ω      2.00  76.00   0.50    0.34    --   43.18-100.00  67.00  148
  4  ω    -72.00 -47.00   0.50    0.70    --  -90.25 100.00 172.00   50
  5  ω     45.00  99.00   0.50    0.70    --  109.26-100.00  67.00  108
  6  ω    108.00 134.00   0.50    0.70    --  109.26 100.00 172.00   52
  7  ω    -20.00  31.00   0.50    0.34    --  -43.18  19.00 -90.00  102
  8  ω    -26.00  17.00   0.50    0.34    --  -43.18  19.00-120.00   86
  9  ω    -72.00  27.00   0.50    0.34    --  -43.18  77.00 -30.00  198
 10  ω    -45.00 -14.00   0.50    0.70    --  -90.25  45.00  30.00   62
 11  ω    -48.00 -19.00   0.50    0.70    --  -90.25  61.00   0.00   58
 12  ω   -142.00 -92.00   0.50    0.70    --  -90.25-100.00  67.00  100
 13  ω   -162.00-137.00   0.50    0.70    --  -90.25 -94.00  30.00   50
 14  ω   -131.00-105.00   0.50    0.70    --  -90.25 -94.00  30.00   52
 15  ω    -50.00 -14.00   0.50    0.70    --  -90.25  45.00 120.00   72
 16  ω    -48.00 -17.00   0.50    0.70    --  -90.25  45.00-150.00   62
 17  ω     37.00  77.00   0.50    0.70    --  109.26-125.00 -60.00   80
 18  ω     35.00  96.00   0.50    0.70    --  109.26 -77.00 120.00  122
 19  ω     87.00 173.00   0.50    0.70    --  109.26  45.00  90.00  172
 20  ω     36.00  65.00   0.50    0.70    --  109.26 -61.00-150.00   58
 21  ω     46.00  71.00   0.50    0.70    --  109.26 -61.00-120.00   50
 22  ω     42.00 103.00   0.50    0.70    --  109.26 -94.00  90.00  122
 23  ω     39.00  71.00   0.50    0.70    --  109.26 -61.00 120.00   64
 24  ω     35.00  70.00   0.50    0.70    --  109.26 -61.00   0.00   70
 25  ω     35.00  60.00   0.50    0.70    --  109.26 -61.00 -60.00   50
 26  ω     36.00  68.00   0.50    0.70    --  109.26 -61.00-180.00   64
 27  ω     72.00  98.00   0.50    0.70    --  109.26 -94.00 120.00   52
 28  ω     40.00  68.00   0.50    0.70    --  109.26 -61.00 -90.00   56
 29  ω     81.00 107.00   0.50    0.70    --  109.26-125.00 -60.00   52
 30  ω     40.00  69.00   0.50    0.70    --  109.26 -61.00  90.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1018122000
_diffrn_orient_matrix_UB_12      -0.0477885000
_diffrn_orient_matrix_UB_13      0.0129112000
_diffrn_orient_matrix_UB_21      -0.0622954000
_diffrn_orient_matrix_UB_22      0.0824500000
_diffrn_orient_matrix_UB_23      -0.0412222000
_diffrn_orient_matrix_UB_31      -0.0089038000
_diffrn_orient_matrix_UB_32      -0.0304098000
_diffrn_orient_matrix_UB_33      -0.1316718000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4154
_reflns_number_total             4442
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4442
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.172
_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)+(0.0526P)²+0.5553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1092
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C26(H26A,H26B), C30(H30A,H30B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19),
 C21(H21)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C31(H31A,H31B,H31C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.84833(3) 0.45101(2) 0.56394(3) 0.03874(12) Uani 1 1 d . . . . .
O1 O 0.74168(8) 0.71639(7) 0.44991(9) 0.0391(3) Uani 1 1 d . . . . .
N1 N 0.61347(9) 0.66942(8) 0.12241(10) 0.0337(3) Uani 1 1 d . . . . .
H1 H 0.655778 0.682456 0.073177 0.040 Uiso 1 1 calc R U . . .
N2 N 0.72685(8) 0.51758(8) 0.36762(10) 0.0300(2) Uani 1 1 d . . . . .
N3 N 0.88439(9) 0.56987(8) 0.40054(11) 0.0323(3) Uani 1 1 d . . . . .
H3 H 0.950183 0.570798 0.425090 0.039 Uiso 1 1 calc R U . . .
N4 N 0.82334(10) 0.78125(8) 0.30499(11) 0.0340(3) Uani 1 1 d . . . . .
C1 C 0.46911(11) 0.65978(9) 0.21119(12) 0.0328(3) Uani 1 1 d . . . . .
C2 C 0.51160(11) 0.69624(9) 0.11432(13) 0.0333(3) Uani 1 1 d . . . . .
C4 C 0.63554(10) 0.61783(9) 0.22379(11) 0.0285(3) Uani 1 1 d . . . . .
C5 C 0.73505(10) 0.57028(9) 0.25835(11) 0.0273(3) Uani 1 1 d . . . . .
C6 C 0.83158(10) 0.62836(9) 0.31016(12) 0.0278(3) Uani 1 1 d . . . . .
C8 C 0.81800(10) 0.51395(9) 0.44138(12) 0.0300(3) Uani 1 1 d . . . . .
C10 C 0.62852(11) 0.48274(10) 0.39362(14) 0.0353(3) Uani 1 1 d . . . . .
H10A H 0.638540 0.456369 0.472915 0.042 Uiso 1 1 calc R U . . .
H10B H 0.603989 0.438238 0.335171 0.042 Uiso 1 1 calc R U . . .
C11 C 0.54782(11) 0.55490(11) 0.38888(14) 0.0375(3) Uani 1 1 d . . . . .
H11A H 0.479270 0.529772 0.387037 0.045 Uiso 1 1 calc R U . . .
H11B H 0.562430 0.590726 0.460396 0.045 Uiso 1 1 calc R U . . .
C12 C 0.54995(10) 0.60947(9) 0.27934(12) 0.0308(3) Uani 1 1 d . . . . .
C13 C 0.36554(12) 0.67711(12) 0.22330(14) 0.0425(4) Uani 1 1 d . . . . .
H13 H 0.335662 0.652923 0.285871 0.051 Uiso 1 1 calc R U . . .
C14 C 0.30905(13) 0.73097(12) 0.14000(17) 0.0502(4) Uani 1 1 d . . . . .
H14 H 0.241127 0.745132 0.148800 0.060 Uiso 1 1 calc R U . . .
C15 C 0.35144(14) 0.76462(11) 0.04299(17) 0.0496(4) Uani 1 1 d . . . . .
H15 H 0.310277 0.799129 -0.012956 0.059 Uiso 1 1 calc R U . . .
C16 C 0.45262(13) 0.74820(10) 0.02760(15) 0.0441(4) Uani 1 1 d . . . . .
H16 H 0.480511 0.770648 -0.037515 0.053 Uiso 1 1 calc R U . . .
C17 C 0.88931(10) 0.75483(9) 0.22276(12) 0.0307(3) Uani 1 1 d . . . . .
C18 C 0.94388(12) 0.80553(11) 0.15214(14) 0.0397(3) Uani 1 1 d . . . . .
H18 H 0.939140 0.865744 0.152942 0.048 Uiso 1 1 calc R U . . .
C19 C 1.00600(12) 0.76339(12) 0.08002(14) 0.0430(4) Uani 1 1 d . . . . .
H19 H 1.042375 0.796472 0.030956 0.052 Uiso 1 1 calc R U . . .
C20 C 1.01589(11) 0.67382(11) 0.07833(14) 0.0398(3) Uani 1 1 d . . . . .
C21 C 0.96275(11) 0.62448(10) 0.15375(14) 0.0357(3) Uani 1 1 d . . . . .
H21 H 0.971036 0.564534 0.157032 0.043 Uiso 1 1 calc R U . . .
C22 C 0.89787(10) 0.66468(9) 0.22348(12) 0.0294(3) Uani 1 1 d . . . . .
C23 C 0.79237(11) 0.71255(9) 0.36713(12) 0.0302(3) Uani 1 1 d . . . . .
C26 C 0.79272(15) 0.87048(10) 0.32562(16) 0.0468(4) Uani 1 1 d . . . . .
H26A H 0.843877 0.909791 0.301028 0.056 Uiso 1 1 calc R U . . .
H26B H 0.791814 0.878983 0.411034 0.056 Uiso 1 1 calc R U . . .
C27 C 0.6882(2) 0.89218(17) 0.2581(3) 0.0901(8) Uani 1 1 d . . . . .
H27A H 0.689528 0.886379 0.173276 0.135 Uiso 1 1 calc R U . . .
H27B H 0.670508 0.950800 0.275827 0.135 Uiso 1 1 calc R U . . .
H27C H 0.637265 0.853297 0.281928 0.135 Uiso 1 1 calc R U . . .
C28 C 1.08085(15) 0.62955(15) -0.00455(19) 0.0591(5) Uani 1 1 d . . . . .
H28A H 1.129561 0.591115 0.041339 0.089 Uiso 1 1 calc R U . . .
H28B H 1.117819 0.672471 -0.043410 0.089 Uiso 1 1 calc R U . . .
H28C H 1.036465 0.596924 -0.064269 0.089 Uiso 1 1 calc R U . . .
C30 C 0.75872(11) 0.51093(10) 0.15512(14) 0.0373(3) Uani 1 1 d . . . . .
H30A H 0.772933 0.547138 0.088818 0.045 Uiso 1 1 calc R U . . .
H30B H 0.821260 0.478105 0.182988 0.045 Uiso 1 1 calc R U . . .
C31 C 0.67258(16) 0.44762(14) 0.1082(2) 0.0597(5) Uani 1 1 d . . . . .
H31A H 0.688446 0.420287 0.036332 0.090 Uiso 1 1 calc R U . . .
H31B H 0.607983 0.478377 0.090546 0.090 Uiso 1 1 calc R U . . .
H31C H 0.666915 0.404204 0.168233 0.090 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
S1 C8 1.6823(14) . ?
O1 C23 1.2186(17) . ?
N1 H1 0.8600 . ?
N1 C2 1.3790(19) . ?
N1 C4 1.3834(17) . ?
N2 C5 1.4885(16) . ?
N2 C8 1.3439(18) . ?
N2 C10 1.4568(17) . ?
N3 H3 0.8600 . ?
N3 C6 1.4521(17) . ?
N3 C8 1.3479(18) . ?
N4 C17 1.4109(18) . ?
N4 C23 1.3614(18) . ?
N4 C26 1.4595(19) . ?
C1 C2 1.408(2) . ?
C1 C12 1.4336(19) . ?
C1 C13 1.401(2) . ?
C2 C16 1.399(2) . ?
C4 C5 1.4887(18) . ?
C4 C12 1.3611(18) . ?
C5 C6 1.5817(18) . ?
C5 C30 1.5432(19) . ?
C6 C22 1.5014(17) . ?
C6 C23 1.5650(18) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.525(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.4938(19) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.392(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.377(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(2) . ?
C17 C22 1.393(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.388(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.386(3) . ?
C20 C21 1.395(2) . ?
C20 C28 1.510(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.3806(19) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.494(3) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C31 1.520(2) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 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
C2 N1 H1 126.1 . . ?
C2 N1 C4 107.87(11) . . ?
C4 N1 H1 126.1 . . ?
C8 N2 C5 111.50(11) . . ?
C8 N2 C10 125.64(12) . . ?
C10 N2 C5 122.59(11) . . ?
C6 N3 H3 124.0 . . ?
C8 N3 H3 124.0 . . ?
C8 N3 C6 111.94(11) . . ?
C17 N4 C26 125.64(13) . . ?
C23 N4 C17 111.49(11) . . ?
C23 N4 C26 122.85(13) . . ?
C2 C1 C12 106.68(12) . . ?
C13 C1 C2 119.52(14) . . ?
C13 C1 C12 133.80(14) . . ?
N1 C2 C1 108.26(12) . . ?
N1 C2 C16 129.83(14) . . ?
C16 C2 C1 121.90(14) . . ?
N1 C4 C5 124.33(11) . . ?
C12 C4 N1 110.33(12) . . ?
C12 C4 C5 124.99(12) . . ?
N2 C5 C4 108.52(10) . . ?
N2 C5 C6 98.94(10) . . ?
N2 C5 C30 110.05(11) . . ?
C4 C5 C6 115.50(11) . . ?
C4 C5 C30 111.01(11) . . ?
C30 C5 C6 112.06(10) . . ?
N3 C6 C5 100.03(10) . . ?
N3 C6 C22 115.25(11) . . ?
N3 C6 C23 112.20(11) . . ?
C22 C6 C5 118.28(11) . . ?
C22 C6 C23 102.10(10) . . ?
C23 C6 C5 109.27(10) . . ?
N2 C8 S1 127.39(11) . . ?
N2 C8 N3 108.40(12) . . ?
N3 C8 S1 124.21(11) . . ?
N2 C10 H10A 109.6 . . ?
N2 C10 H10B 109.6 . . ?
N2 C10 C11 110.21(12) . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C10 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 C10 110.02(11) . . ?
C12 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C1 C12 C11 129.96(12) . . ?
C4 C12 C1 106.85(12) . . ?
C4 C12 C11 123.17(12) . . ?
C1 C13 H13 120.9 . . ?
C14 C13 C1 118.24(16) . . ?
C14 C13 H13 120.9 . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.46(16) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 119.1 . . ?
C16 C15 C14 121.81(15) . . ?
C16 C15 H15 119.1 . . ?
C2 C16 H16 121.5 . . ?
C15 C16 C2 117.01(16) . . ?
C15 C16 H16 121.5 . . ?
C18 C17 N4 128.82(14) . . ?
C18 C17 C22 121.28(13) . . ?
C22 C17 N4 109.86(12) . . ?
C17 C18 H18 121.2 . . ?
C17 C18 C19 117.64(15) . . ?
C19 C18 H18 121.2 . . ?
C18 C19 H19 118.8 . . ?
C20 C19 C18 122.48(14) . . ?
C20 C19 H19 118.8 . . ?
C19 C20 C21 118.60(14) . . ?
C19 C20 C28 121.31(15) . . ?
C21 C20 C28 120.08(16) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 119.98(14) . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C6 108.79(11) . . ?
C21 C22 C6 131.24(13) . . ?
C21 C22 C17 119.94(13) . . ?
O1 C23 N4 126.03(13) . . ?
O1 C23 C6 126.75(13) . . ?
N4 C23 C6 107.20(11) . . ?
N4 C26 H26A 109.1 . . ?
N4 C26 H26B 109.1 . . ?
N4 C26 C27 112.32(17) . . ?
H26A C26 H26B 107.9 . . ?
C27 C26 H26A 109.1 . . ?
C27 C26 H26B 109.1 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C20 C28 H28A 109.5 . . ?
C20 C28 H28B 109.5 . . ?
C20 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C5 C30 H30A 108.5 . . ?
C5 C30 H30B 108.5 . . ?
H30A C30 H30B 107.5 . . ?
C31 C30 C5 114.92(12) . . ?
C31 C30 H30A 108.5 . . ?
C31 C30 H30B 108.5 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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
N1 C2 C16 C15 -179.89(15) . . . . ?
N1 C4 C5 N2 -176.27(12) . . . . ?
N1 C4 C5 C6 73.77(16) . . . . ?
N1 C4 C5 C30 -55.21(17) . . . . ?
N1 C4 C12 C1 -1.13(16) . . . . ?
N1 C4 C12 C11 177.64(13) . . . . ?
N2 C5 C6 N3 28.15(11) . . . . ?
N2 C5 C6 C22 154.10(11) . . . . ?
N2 C5 C6 C23 -89.77(11) . . . . ?
N2 C5 C30 C31 65.88(18) . . . . ?
N2 C10 C11 C12 45.79(17) . . . . ?
N3 C6 C22 C17 -126.93(13) . . . . ?
N3 C6 C22 C21 50.9(2) . . . . ?
N3 C6 C23 O1 -50.12(19) . . . . ?
N3 C6 C23 N4 131.30(12) . . . . ?
N4 C17 C18 C19 178.47(14) . . . . ?
N4 C17 C22 C6 1.16(16) . . . . ?
N4 C17 C22 C21 -176.94(13) . . . . ?
C1 C2 C16 C15 2.0(2) . . . . ?
C1 C13 C14 C15 2.8(3) . . . . ?
C2 N1 C4 C5 174.70(13) . . . . ?
C2 N1 C4 C12 1.25(16) . . . . ?
C2 C1 C12 C4 0.59(16) . . . . ?
C2 C1 C12 C11 -178.06(15) . . . . ?
C2 C1 C13 C14 -1.0(2) . . . . ?
C4 N1 C2 C1 -0.84(16) . . . . ?
C4 N1 C2 C16 -179.16(15) . . . . ?
C4 C5 C6 N3 143.70(11) . . . . ?
C4 C5 C6 C22 -90.35(14) . . . . ?
C4 C5 C6 C23 25.78(14) . . . . ?
C4 C5 C30 C31 -54.28(19) . . . . ?
C5 N2 C8 S1 -170.80(10) . . . . ?
C5 N2 C8 N3 8.69(16) . . . . ?
C5 N2 C10 C11 -52.67(18) . . . . ?
C5 C4 C12 C1 -174.54(13) . . . . ?
C5 C4 C12 C11 4.2(2) . . . . ?
C5 C6 C22 C17 114.88(13) . . . . ?
C5 C6 C22 C21 -67.3(2) . . . . ?
C5 C6 C23 O1 59.87(18) . . . . ?
C5 C6 C23 N4 -118.71(12) . . . . ?
C6 N3 C8 S1 -167.60(10) . . . . ?
C6 N3 C8 N2 12.89(16) . . . . ?
C6 C5 C30 C31 174.92(15) . . . . ?
C8 N2 C5 C4 -144.63(12) . . . . ?
C8 N2 C5 C6 -23.81(13) . . . . ?
C8 N2 C5 C30 93.72(13) . . . . ?
C8 N2 C10 C11 120.86(15) . . . . ?
C8 N3 C6 C5 -26.72(14) . . . . ?
C8 N3 C6 C22 -154.70(12) . . . . ?
C8 N3 C6 C23 89.01(14) . . . . ?
C10 N2 C5 C4 29.73(17) . . . . ?
C10 N2 C5 C6 150.55(12) . . . . ?
C10 N2 C5 C30 -91.93(15) . . . . ?
C10 N2 C8 S1 15.1(2) . . . . ?
C10 N2 C8 N3 -165.45(13) . . . . ?
C10 C11 C12 C1 152.74(15) . . . . ?
C10 C11 C12 C4 -25.7(2) . . . . ?
C12 C1 C2 N1 0.16(16) . . . . ?
C12 C1 C2 C16 178.64(14) . . . . ?
C12 C1 C13 C14 178.96(16) . . . . ?
C12 C4 C5 N2 -3.77(19) . . . . ?
C12 C4 C5 C6 -113.73(15) . . . . ?
C12 C4 C5 C30 117.30(15) . . . . ?
C13 C1 C2 N1 -179.84(14) . . . . ?
C13 C1 C2 C16 -1.4(2) . . . . ?
C13 C1 C12 C4 -179.41(16) . . . . ?
C13 C1 C12 C11 1.9(3) . . . . ?
C13 C14 C15 C16 -2.2(3) . . . . ?
C14 C15 C16 C2 -0.2(2) . . . . ?
C17 N4 C23 O1 174.24(14) . . . . ?
C17 N4 C23 C6 -7.17(15) . . . . ?
C17 N4 C26 C27 98.3(2) . . . . ?
C17 C18 C19 C20 -1.0(2) . . . . ?
C18 C17 C22 C6 178.85(13) . . . . ?
C18 C17 C22 C21 0.7(2) . . . . ?
C18 C19 C20 C21 -1.2(2) . . . . ?
C18 C19 C20 C28 177.65(16) . . . . ?
C19 C20 C21 C22 3.2(2) . . . . ?
C20 C21 C22 C6 179.36(14) . . . . ?
C20 C21 C22 C17 -3.0(2) . . . . ?
C22 C6 C23 O1 -174.09(14) . . . . ?
C22 C6 C23 N4 7.33(14) . . . . ?
C22 C17 C18 C19 1.3(2) . . . . ?
C23 N4 C17 C18 -173.44(14) . . . . ?
C23 N4 C17 C22 4.03(17) . . . . ?
C23 N4 C26 C27 -83.5(2) . . . . ?
C23 C6 C22 C17 -5.03(14) . . . . ?
C23 C6 C22 C21 172.79(15) . . . . ?
C26 N4 C17 C18 5.0(2) . . . . ?
C26 N4 C17 C22 -177.53(14) . . . . ?
C26 N4 C23 O1 -4.3(2) . . . . ?
C26 N4 C23 C6 174.33(14) . . . . ?
C28 C20 C21 C22 -175.63(15) . . . . ?
C30 C5 C6 N3 -87.84(13) . . . . ?
C30 C5 C6 C22 38.12(16) . . . . ?
C30 C5 C6 C23 154.24(11) . . . . ?

_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 1.433
_oxdiff_exptl_absorpt_empirical_full_min 0.563
