# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_b-7
_audit_block_doi                 10.5517/ccdc.csd.cc23t8px
_database_code_depnum_ccdc_archive 'CCDC 1960709'
loop_
_audit_author_name
_audit_author_address
aa
;aa
China
;
_audit_update_record             
;
2019-10-22 deposited with the CCDC.	2020-08-19 downloaded from the CCDC.
;
_audit_creation_date             2019-06-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 N2 O S'
_chemical_formula_sum            'C21 H18 N2 O S'
_chemical_formula_weight         346.43
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.3700(4)
_cell_length_b                   10.2878(4)
_cell_length_c                   14.5801(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.519(4)
_cell_angle_gamma                90
_cell_volume                     1690.80(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3529
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.9350
_cell_measurement_theta_min      2.6650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7544
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.141
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  85.00   1.00    3.00    --   11.74  57.00 120.00  101
  2  ω    -58.00  37.00   1.00    3.00    --   11.74 -19.00 -60.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0509369000
_diffrn_orient_matrix_UB_12      -0.0110977000
_diffrn_orient_matrix_UB_13      -0.0222907000
_diffrn_orient_matrix_UB_21      -0.0349199000
_diffrn_orient_matrix_UB_22      0.0072990000
_diffrn_orient_matrix_UB_23      -0.0437254000
_diffrn_orient_matrix_UB_31      0.0120737000
_diffrn_orient_matrix_UB_32      0.0676228000
_diffrn_orient_matrix_UB_33      0.0010786000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2569
_reflns_number_total             2978
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2978
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.048
_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)+(0.0319P)²+0.9959P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0901
_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:
 C10(H10), C9(H9), C13(H13), C2(H2), C16(H16), C12(H12), C20(H20), C3(H3),
 C5(H5), C19(H19), C17(H17), C4(H4)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C14(H14A,H14B,H14C)
;
_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 0.24136(4) 0.22318(4) 0.22656(3) 0.01630(14) Uani 1 1 d . . . . .
O1 O 0.66622(11) 0.67711(12) 0.14877(9) 0.0202(3) Uani 1 1 d . . . . .
N1 N 0.33495(13) 0.15403(14) 0.40252(10) 0.0143(3) Uani 1 1 d . . . . .
N2 N 0.48217(13) 0.29577(14) 0.44419(10) 0.0154(3) Uani 1 1 d . . . . .
C8 C 0.48598(15) 0.41827(16) 0.29986(12) 0.0130(4) Uani 1 1 d . . . . .
C7 C 0.43421(15) 0.31874(17) 0.35433(13) 0.0141(4) Uani 1 1 d . . . . .
C11 C 0.60746(15) 0.59637(17) 0.20221(13) 0.0151(4) Uani 1 1 d . . . . .
C1 C 0.42147(16) 0.19533(17) 0.47228(13) 0.0152(4) Uani 1 1 d . . . . .
C15 C 0.30236(15) 0.09849(17) 0.16186(13) 0.0145(4) Uani 1 1 d . . . . .
C6 C 0.34231(16) 0.23359(17) 0.32640(13) 0.0151(4) Uani 1 1 d . . . . .
C10 C 0.60168(16) 0.61518(17) 0.29557(13) 0.0163(4) Uani 1 1 d . . . . .
H10 H 0.638870 0.686485 0.326020 0.020 Uiso 1 1 calc R . . . .
C9 C 0.54018(15) 0.52717(17) 0.34346(13) 0.0160(4) Uani 1 1 d . . . . .
H9 H 0.535069 0.541196 0.405829 0.019 Uiso 1 1 calc R . . . .
C13 C 0.49222(15) 0.40150(17) 0.20528(13) 0.0151(4) Uani 1 1 d . . . . .
H13 H 0.455838 0.329860 0.174694 0.018 Uiso 1 1 calc R . . . .
C2 C 0.43482(17) 0.12706(18) 0.55679(13) 0.0178(4) Uani 1 1 d . . . . .
H2 H 0.491725 0.152639 0.605107 0.021 Uiso 1 1 calc R . . . .
C16 C 0.25119(16) 0.08215(18) 0.07046(13) 0.0189(4) Uani 1 1 d . . . . .
H16 H 0.189082 0.135524 0.045554 0.023 Uiso 1 1 calc R . . . .
C12 C 0.55156(15) 0.48971(17) 0.15691(13) 0.0158(4) Uani 1 1 d . . . . .
H12 H 0.554202 0.477889 0.093971 0.019 Uiso 1 1 calc R . . . .
C20 C 0.39397(16) 0.01724(18) 0.19788(13) 0.0184(4) Uani 1 1 d . . . . .
H20 H 0.428744 0.027351 0.258826 0.022 Uiso 1 1 calc R . . . .
C18 C 0.38476(16) -0.09622(17) 0.05174(13) 0.0179(4) Uani 1 1 d . . . . .
C3 C 0.36337(17) 0.02318(18) 0.56685(14) 0.0207(4) Uani 1 1 d . . . . .
H3 H 0.371262 -0.021949 0.622588 0.025 Uiso 1 1 calc R . . . .
C5 C 0.26373(16) 0.04827(18) 0.41231(13) 0.0184(4) Uani 1 1 d . . . . .
H5 H 0.207229 0.022033 0.363912 0.022 Uiso 1 1 calc R . . . .
C19 C 0.43395(17) -0.07928(18) 0.14311(13) 0.0199(4) Uani 1 1 d . . . . .
H19 H 0.495067 -0.133796 0.168230 0.024 Uiso 1 1 calc R . . . .
C17 C 0.29319(17) -0.01368(18) 0.01714(13) 0.0203(4) Uani 1 1 d . . . . .
H17 H 0.258997 -0.023242 -0.044004 0.024 Uiso 1 1 calc R . . . .
C4 C 0.27721(17) -0.01676(18) 0.49330(14) 0.0215(5) Uani 1 1 d . . . . .
H4 H 0.229542 -0.088395 0.500899 0.026 Uiso 1 1 calc R . . . .
C21 C 0.42878(18) -0.19994(19) -0.00825(15) 0.0249(5) Uani 1 1 d . . . . .
H21A H 0.476878 -0.160875 -0.050165 0.037 Uiso 1 1 calc GR . . . .
H21B H 0.362328 -0.242979 -0.042843 0.037 Uiso 1 1 calc GR . . . .
H21C H 0.475195 -0.262085 0.030032 0.037 Uiso 1 1 calc GR . . . .
C14 C 0.75053(18) 0.76523(19) 0.19572(15) 0.0266(5) Uani 1 1 d . . . . .
H14A H 0.796139 0.804090 0.152003 0.040 Uiso 1 1 calc GR . . . .
H14B H 0.802511 0.718947 0.241689 0.040 Uiso 1 1 calc GR . . . .
H14C H 0.709628 0.831906 0.225042 0.040 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C15 1.7854(18) . ?
S1 C6 1.7351(19) . ?
O1 C11 1.371(2) . ?
O1 C14 1.427(2) . ?
N1 C1 1.386(2) . ?
N1 C6 1.390(2) . ?
N1 C5 1.375(2) . ?
N2 C7 1.372(2) . ?
N2 C1 1.336(2) . ?
C8 C7 1.466(2) . ?
C8 C9 1.392(2) . ?
C8 C13 1.401(3) . ?
C7 C6 1.383(2) . ?
C11 C10 1.385(3) . ?
C11 C12 1.391(2) . ?
C1 C2 1.409(3) . ?
C15 C16 1.393(3) . ?
C15 C20 1.384(3) . ?
C10 H10 0.9300 . ?
C10 C9 1.387(3) . ?
C9 H9 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.379(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.362(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(3) . ?
C12 H12 0.9300 . ?
C20 H20 0.9300 . ?
C20 C19 1.388(3) . ?
C18 C19 1.387(3) . ?
C18 C17 1.386(3) . ?
C18 C21 1.506(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.415(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.348(3) . ?
C19 H19 0.9300 . ?
C17 H17 0.9300 . ?
C4 H4 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C6 S1 C15 103.15(8) . . ?
C11 O1 C14 117.31(15) . . ?
C1 N1 C6 107.11(14) . . ?
C5 N1 C1 122.51(16) . . ?
C5 N1 C6 130.29(16) . . ?
C1 N2 C7 105.61(15) . . ?
C9 C8 C7 120.01(16) . . ?
C9 C8 C13 118.20(16) . . ?
C13 C8 C7 121.54(16) . . ?
N2 C7 C8 120.01(16) . . ?
N2 C7 C6 111.26(16) . . ?
C6 C7 C8 128.64(17) . . ?
O1 C11 C10 124.28(16) . . ?
O1 C11 C12 115.76(16) . . ?
C10 C11 C12 119.96(17) . . ?
N1 C1 C2 118.28(16) . . ?
N2 C1 N1 110.95(16) . . ?
N2 C1 C2 130.73(17) . . ?
C16 C15 S1 116.72(14) . . ?
C20 C15 S1 123.95(14) . . ?
C20 C15 C16 119.31(17) . . ?
N1 C6 S1 122.08(13) . . ?
C7 C6 S1 132.63(15) . . ?
C7 C6 N1 105.06(15) . . ?
C11 C10 H10 120.2 . . ?
C11 C10 C9 119.70(17) . . ?
C9 C10 H10 120.2 . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.19(17) . . ?
C10 C9 H9 119.4 . . ?
C8 C13 H13 119.5 . . ?
C12 C13 C8 120.92(17) . . ?
C12 C13 H13 119.5 . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.20(18) . . ?
C3 C2 H2 120.4 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.57(17) . . ?
C17 C16 H16 120.2 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.01(17) . . ?
C13 C12 H12 120.0 . . ?
C15 C20 H20 120.0 . . ?
C15 C20 C19 120.05(17) . . ?
C19 C20 H20 120.0 . . ?
C19 C18 C17 117.51(17) . . ?
C19 C18 C21 121.60(17) . . ?
C17 C18 C21 120.89(17) . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.64(18) . . ?
C4 C3 H3 119.7 . . ?
N1 C5 H5 120.6 . . ?
C4 C5 N1 118.86(18) . . ?
C4 C5 H5 120.6 . . ?
C20 C19 H19 119.3 . . ?
C18 C19 C20 121.43(17) . . ?
C18 C19 H19 119.3 . . ?
C16 C17 C18 122.12(18) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.50(18) . . ?
C5 C4 H4 119.7 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.247
_oxdiff_exptl_absorpt_empirical_full_min 0.763
####################################################################### 
# 
# 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_20191108-mxjaaa
_database_code_depnum_ccdc_archive 'CCDC 1970761'
loop_
_audit_author_name
_audit_author_address
ZHONG
;CC
China
;
_audit_update_record             
;
2019-12-09 deposited with the CCDC.	2020-08-19 downloaded from the CCDC.
;
_audit_creation_date             2019-12-09
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 N3 O S, 0.75(C H4 O)'
_chemical_formula_sum            'C22.75 H22 N3 O1.75 S'
_chemical_formula_weight         397.49
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   4.9241(18)
_cell_length_b                   14.209(4)
_cell_length_c                   15.2990(16)
_cell_angle_alpha                90.853(15)
_cell_angle_beta                 96.934(19)
_cell_angle_gamma                99.10(3)
_cell_volume                     1048.6(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1174
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.4610
_cell_measurement_theta_min      3.8590
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.931
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             419
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2226
_diffrn_reflns_av_unetI/netI     0.2078
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10064
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.713
_diffrn_reflns_theta_max         24.713
_diffrn_reflns_theta_min         3.888
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00  91.00   1.00   15.00    --   17.77   0.00-120.00  146
  2  ω    -20.00  60.00   1.00   15.00    --   17.77 -99.00-120.00   80
  3  ω      5.00  78.00   1.00   15.00    --   17.77-129.00  27.00   73
  4  ω    -90.00  10.00   1.00   15.00    --  -19.57 -77.00  60.00  100
  5  ω    -88.00   2.00   1.00   15.00    --  -19.57 -57.00 120.00   90
  6  ω     34.00  66.00   1.00   15.00    --   17.77-178.00-150.00   32
  7  ω    -26.00  91.00   1.00   15.00    --   17.77  19.00   0.00  117
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0172750000
_diffrn_orient_matrix_UB_12      -0.0463926000
_diffrn_orient_matrix_UB_13      -0.0197373000
_diffrn_orient_matrix_UB_21      -0.0090641000
_diffrn_orient_matrix_UB_22      0.0197705000
_diffrn_orient_matrix_UB_23      -0.0423499000
_diffrn_orient_matrix_UB_31      0.1457302000
_diffrn_orient_matrix_UB_32      0.0039550000
_diffrn_orient_matrix_UB_33      0.0009038000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1095
_reflns_number_total             3555
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (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 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.890
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3555
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.2222
_refine_ls_R_factor_gt           0.1070
_refine_ls_restrained_S_all      0.892
_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)+(0.1128P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2312
_refine_ls_wR_factor_ref         0.3136
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O2) \\sim Ueq, Uanis(C23) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Fixed Sof: O2(0.75) H2(0.75) C23(0.75) H23A(0.75) H23B(0.75) H23C(0.75)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14), C17(H17),
 C18(H18), C20(H20), C21(H21)
4.b X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
4.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
4.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 -0.0183(4) 0.66055(13) 0.57409(10) 0.0718(7) Uani 1 1 d . . . . .
O1 O 0.9483(13) 0.4361(4) 0.8908(3) 0.1043(19) Uani 1 1 d . . . . .
N1 N 0.3478(10) 0.5706(4) 0.6740(3) 0.0576(14) Uani 1 1 d . . . . .
N2 N 0.3955(11) 0.6369(4) 0.8098(3) 0.0649(15) Uani 1 1 d . . . . .
N3 N 0.7379(12) 0.5538(4) 0.9339(4) 0.0876(19) Uani 1 1 d . . . . .
H3A H 0.8138 0.5538 0.9875 0.105 Uiso 1 1 calc R U . . .
H3B H 0.6260 0.5931 0.9188 0.105 Uiso 1 1 calc R U . . .
C1 C 0.7931(17) 0.4936(5) 0.8747(4) 0.075(2) Uani 1 1 d . . . . .
C2 C 0.6429(14) 0.5011(5) 0.7826(4) 0.0673(18) Uani 1 1 d . . . . .
C3 C 0.6834(15) 0.4393(5) 0.7198(4) 0.076(2) Uani 1 1 d . . . . .
H3 H 0.8012 0.3950 0.7335 0.091 Uiso 1 1 calc R U . . .
C4 C 0.5474(15) 0.4412(5) 0.6330(4) 0.076(2) Uani 1 1 d . . . . .
H4 H 0.5720 0.3969 0.5905 0.092 Uiso 1 1 calc R U . . .
C5 C 0.3857(14) 0.5056(5) 0.6117(4) 0.0671(18) Uani 1 1 d . . . . .
H5 H 0.2979 0.5065 0.5545 0.081 Uiso 1 1 calc R U . . .
C6 C 0.4698(13) 0.5683(5) 0.7615(4) 0.0596(17) Uani 1 1 d . . . . .
C7 C 0.2313(13) 0.6837(5) 0.7546(4) 0.0627(17) Uani 1 1 d . . . . .
C8 C 0.1922(13) 0.6444(5) 0.6691(4) 0.0627(18) Uani 1 1 d . . . . .
C9 C 0.1048(13) 0.7615(5) 0.7885(4) 0.0603(17) Uani 1 1 d . . . . .
C10 C 0.0824(16) 0.7700(5) 0.8790(5) 0.084(2) Uani 1 1 d . . . . .
H10 H 0.1567 0.7277 0.9172 0.100 Uiso 1 1 calc R U . . .
C11 C -0.0438(17) 0.8378(6) 0.9118(5) 0.092(2) Uani 1 1 d . . . . .
H11 H -0.0588 0.8401 0.9718 0.110 Uiso 1 1 calc R U . . .
C12 C -0.1530(16) 0.9050(6) 0.8577(6) 0.089(2) Uani 1 1 d . . . . .
C13 C -0.1241(15) 0.8981(6) 0.7699(5) 0.083(2) Uani 1 1 d . . . . .
H13 H -0.1931 0.9418 0.7322 0.100 Uiso 1 1 calc R U . . .
C14 C 0.0020(14) 0.8295(5) 0.7359(4) 0.0691(19) Uani 1 1 d . . . . .
H14 H 0.0193 0.8284 0.6760 0.083 Uiso 1 1 calc R U . . .
C15 C -0.3028(16) 0.9771(6) 0.8947(6) 0.115(3) Uani 1 1 d . . . . .
H15A H -0.4914 0.9677 0.8672 0.172 Uiso 1 1 calc R U . . .
H15B H -0.2135 1.0401 0.8834 0.172 Uiso 1 1 calc R U . . .
H15C H -0.2995 0.9699 0.9571 0.172 Uiso 1 1 calc R U . . .
C16 C 0.1994(14) 0.7435(5) 0.5147(4) 0.0596(17) Uani 1 1 d . . . . .
C17 C 0.4313(14) 0.7998(5) 0.5549(4) 0.0700(19) Uani 1 1 d . . . . .
H17 H 0.4871 0.7959 0.6148 0.084 Uiso 1 1 calc R U . . .
C18 C 0.5844(16) 0.8640(6) 0.5029(5) 0.085(2) Uani 1 1 d . . . . .
H18 H 0.7453 0.9018 0.5298 0.102 Uiso 1 1 calc R U . . .
C19 C 0.5090(17) 0.8737(6) 0.4151(5) 0.073(2) Uani 1 1 d . . . . .
C20 C 0.2729(19) 0.8171(6) 0.3786(5) 0.083(2) Uani 1 1 d . . . . .
H20 H 0.2152 0.8223 0.3190 0.099 Uiso 1 1 calc R U . . .
C21 C 0.1128(15) 0.7517(5) 0.4261(5) 0.079(2) Uani 1 1 d . . . . .
H21 H -0.0485 0.7145 0.3989 0.095 Uiso 1 1 calc R U . . .
C22 C 0.6787(16) 0.9431(6) 0.3619(6) 0.109(3) Uani 1 1 d . . . . .
H22A H 0.7027 0.9121 0.3078 0.164 Uiso 1 1 calc R U . . .
H22B H 0.8568 0.9648 0.3949 0.164 Uiso 1 1 calc R U . . .
H22C H 0.5851 0.9965 0.3490 0.164 Uiso 1 1 calc R U . . .
O2 O 0.041(3) 0.2489(9) 0.8438(9) 0.200(5) Uani 0.75 1 d . U P . .
H2 H 0.0127 0.2967 0.8697 0.300 Uiso 0.75 1 calc R U P . .
C23 C 0.313(3) 0.2420(11) 0.8590(10) 0.153(6) Uani 0.75 1 d . U P . .
H23A H 0.4048 0.2682 0.8109 0.229 Uiso 0.75 1 calc R U P . .
H23B H 0.3329 0.1761 0.8642 0.229 Uiso 0.75 1 calc R U P . .
H23C H 0.3933 0.2766 0.9126 0.229 Uiso 0.75 1 calc R U P . .


_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 1.721(6) . ?
S1 C16 1.797(7) . ?
O1 C1 1.212(8) . ?
N1 C5 1.366(7) . ?
N1 C6 1.403(7) . ?
N1 C8 1.390(7) . ?
N2 C6 1.337(7) . ?
N2 C7 1.353(7) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N3 C1 1.317(8) . ?
C1 C2 1.525(9) . ?
C2 C3 1.345(9) . ?
C2 C6 1.394(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.417(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.324(8) . ?
C5 H5 0.9300 . ?
C7 C8 1.395(8) . ?
C7 C9 1.469(8) . ?
C9 C10 1.407(8) . ?
C9 C14 1.384(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.349(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.401(10) . ?
C12 C13 1.371(10) . ?
C12 C15 1.496(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.364(8) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.360(9) . ?
C16 C21 1.384(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.408(9) . ?
C18 H18 0.9300 . ?
C18 C19 1.366(9) . ?
C19 C20 1.358(10) . ?
C19 C22 1.503(9) . ?
C20 H20 0.9300 . ?
C20 C21 1.392(10) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O2 H2 0.8200 . ?
O2 C23 1.349(14) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 S1 C16 103.8(3) . . ?
C5 N1 C6 121.0(5) . . ?
C5 N1 C8 131.4(5) . . ?
C8 N1 C6 107.6(5) . . ?
C6 N2 C7 106.8(5) . . ?
H3A N3 H3B 120.0 . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
O1 C1 N3 123.9(7) . . ?
O1 C1 C2 121.8(6) . . ?
N3 C1 C2 114.3(7) . . ?
C3 C2 C1 117.2(6) . . ?
C3 C2 C6 119.7(6) . . ?
C6 C2 C1 123.1(6) . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.3(6) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(6) . . ?
C5 C4 H4 119.7 . . ?
N1 C5 H5 120.0 . . ?
C4 C5 N1 119.9(6) . . ?
C4 C5 H5 120.0 . . ?
N2 C6 N1 109.6(5) . . ?
N2 C6 C2 132.1(6) . . ?
C2 C6 N1 118.3(6) . . ?
N2 C7 C8 111.6(6) . . ?
N2 C7 C9 120.4(6) . . ?
C8 C7 C9 127.9(6) . . ?
N1 C8 S1 120.7(5) . . ?
N1 C8 C7 104.3(5) . . ?
C7 C8 S1 134.5(5) . . ?
C10 C9 C7 120.1(6) . . ?
C14 C9 C7 123.7(6) . . ?
C14 C9 C10 116.2(6) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.7(7) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.6(8) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C15 120.7(8) . . ?
C13 C12 C11 116.5(7) . . ?
C13 C12 C15 122.7(9) . . ?
C12 C13 H13 118.8 . . ?
C14 C13 C12 122.5(8) . . ?
C14 C13 H13 118.8 . . ?
C9 C14 H14 119.3 . . ?
C13 C14 C9 121.5(7) . . ?
C13 C14 H14 119.3 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 S1 122.3(5) . . ?
C17 C16 C21 120.7(7) . . ?
C21 C16 S1 116.9(6) . . ?
C16 C17 H17 121.0 . . ?
C16 C17 C18 117.9(6) . . ?
C18 C17 H17 121.0 . . ?
C17 C18 H18 118.3 . . ?
C19 C18 C17 123.4(8) . . ?
C19 C18 H18 118.3 . . ?
C18 C19 C22 121.7(8) . . ?
C20 C19 C18 116.2(8) . . ?
C20 C19 C22 122.0(7) . . ?
C19 C20 H20 118.4 . . ?
C19 C20 C21 123.3(7) . . ?
C21 C20 H20 118.4 . . ?
C16 C21 C20 118.4(7) . . ?
C16 C21 H21 120.8 . . ?
C20 C21 H21 120.8 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 O2 H2 109.5 . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C16 C17 C18 -178.6(5) . . . . ?
S1 C16 C21 C20 178.4(5) . . . . ?
O1 C1 C2 C3 1.8(11) . . . . ?
O1 C1 C2 C6 -178.0(7) . . . . ?
N2 C7 C8 S1 171.1(5) . . . . ?
N2 C7 C8 N1 -1.1(7) . . . . ?
N2 C7 C9 C10 -18.9(10) . . . . ?
N2 C7 C9 C14 161.1(6) . . . . ?
N3 C1 C2 C3 -177.8(7) . . . . ?
N3 C1 C2 C6 2.3(10) . . . . ?
C1 C2 C3 C4 179.1(6) . . . . ?
C1 C2 C6 N1 178.3(6) . . . . ?
C1 C2 C6 N2 0.2(12) . . . . ?
C2 C3 C4 C5 2.0(11) . . . . ?
C3 C2 C6 N1 -1.6(10) . . . . ?
C3 C2 C6 N2 -179.7(7) . . . . ?
C3 C4 C5 N1 -0.3(11) . . . . ?
C5 N1 C6 N2 -178.2(5) . . . . ?
C5 N1 C6 C2 3.3(9) . . . . ?
C5 N1 C8 S1 5.0(9) . . . . ?
C5 N1 C8 C7 178.6(6) . . . . ?
C6 N1 C5 C4 -2.4(10) . . . . ?
C6 N1 C8 S1 -172.9(4) . . . . ?
C6 N1 C8 C7 0.6(7) . . . . ?
C6 N2 C7 C8 1.1(7) . . . . ?
C6 N2 C7 C9 177.4(6) . . . . ?
C6 C2 C3 C4 -1.0(11) . . . . ?
C7 N2 C6 N1 -0.7(7) . . . . ?
C7 N2 C6 C2 177.5(7) . . . . ?
C7 C9 C10 C11 -176.9(7) . . . . ?
C7 C9 C14 C13 177.2(6) . . . . ?
C8 S1 C16 C17 -19.6(6) . . . . ?
C8 S1 C16 C21 163.8(5) . . . . ?
C8 N1 C5 C4 179.9(6) . . . . ?
C8 N1 C6 N2 0.0(7) . . . . ?
C8 N1 C6 C2 -178.5(6) . . . . ?
C8 C7 C9 C10 156.7(7) . . . . ?
C8 C7 C9 C14 -23.2(11) . . . . ?
C9 C7 C8 S1 -4.9(12) . . . . ?
C9 C7 C8 N1 -177.1(6) . . . . ?
C9 C10 C11 C12 -1.7(13) . . . . ?
C10 C9 C14 C13 -2.7(11) . . . . ?
C10 C11 C12 C13 -0.1(13) . . . . ?
C10 C11 C12 C15 177.4(7) . . . . ?
C11 C12 C13 C14 0.4(12) . . . . ?
C12 C13 C14 C9 1.1(12) . . . . ?
C14 C9 C10 C11 3.0(11) . . . . ?
C15 C12 C13 C14 -177.1(7) . . . . ?
C16 S1 C8 N1 -92.3(5) . . . . ?
C16 S1 C8 C7 96.5(7) . . . . ?
C16 C17 C18 C19 1.2(11) . . . . ?
C17 C16 C21 C20 1.7(10) . . . . ?
C17 C18 C19 C20 0.0(11) . . . . ?
C17 C18 C19 C22 -179.9(6) . . . . ?
C18 C19 C20 C21 -0.4(11) . . . . ?
C19 C20 C21 C16 -0.4(11) . . . . ?
C21 C16 C17 C18 -2.1(10) . . . . ?
C22 C19 C20 C21 179.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.739
_oxdiff_exptl_absorpt_empirical_full_min 0.438
####################################################################### 
# 
# 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_20191007_pym_zpf_q_64aaa
_database_code_depnum_ccdc_archive 'CCDC 1960714'
loop_
_audit_author_name
_audit_author_address
b
;b
China
;
_audit_update_record             
;
2019-10-22 deposited with the CCDC.	2020-08-19 downloaded from the CCDC.
;
_audit_creation_date             2019-10-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H20 N2 S'
_chemical_formula_sum            'C25 H20 N2 S'
_chemical_formula_weight         380.49
_chemical_absolute_configuration ?
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.6915(2)
_cell_length_b                   12.7636(6)
_cell_length_c                   26.8264(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1948.80(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1658
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.7520
_cell_measurement_theta_min      3.8780
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            7167
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.432
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     14.00  79.00   1.00   16.00    --   17.77-135.00  62.00   65
  2  ω     -8.00  76.00   1.00   16.00    --   17.77  38.00  30.00   84
  3  ω     12.00  52.00   1.00   16.00    --  -19.57  19.00 -60.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0130531000
_diffrn_orient_matrix_UB_12      0.0549713000
_diffrn_orient_matrix_UB_13      -0.0028466000
_diffrn_orient_matrix_UB_21      0.0004318000
_diffrn_orient_matrix_UB_22      0.0060828000
_diffrn_orient_matrix_UB_23      0.0262682000
_diffrn_orient_matrix_UB_31      0.1239256000
_diffrn_orient_matrix_UB_32      -0.0058428000
_diffrn_orient_matrix_UB_33      0.0001875000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.653
_reflns_Friedel_fraction_full    0.940
_reflns_Friedel_fraction_max     0.914
_reflns_number_gt                2720
_reflns_number_total             3830
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 803 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3830
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0520
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²+0.0235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1254
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15),
 C17(H17), C18(H18), C21(H21), C22(H22), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C19(H19A,H19B,H19C)
;
_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 0.84996(17) 0.54613(9) 0.15326(5) 0.0604(4) Uani 1 1 d . . . . .
N1 N 0.4901(5) 0.4889(3) 0.21425(13) 0.0481(9) Uani 1 1 d . . . . .
N2 N 0.3784(5) 0.3294(3) 0.19088(11) 0.0456(8) Uani 1 1 d . . . . .
C1 C 0.8525(9) 0.0842(4) 0.00222(18) 0.0809(15) Uani 1 1 d . . . . .
H1A H 0.923218 0.021858 0.015454 0.121 Uiso 1 1 calc GR . . . .
H1B H 0.962585 0.119269 -0.019147 0.121 Uiso 1 1 calc GR . . . .
H1C H 0.714886 0.065831 -0.016540 0.121 Uiso 1 1 calc GR . . . .
C2 C 0.7848(8) 0.1556(4) 0.04426(17) 0.0595(12) Uani 1 1 d . . . . .
C3 C 0.5732(8) 0.1444(4) 0.06850(18) 0.0658(13) Uani 1 1 d . . . . .
H3 H 0.473234 0.090279 0.059133 0.079 Uiso 1 1 calc R . . . .
C4 C 0.5044(8) 0.2117(4) 0.10657(17) 0.0598(12) Uani 1 1 d . . . . .
H4 H 0.359251 0.202250 0.121827 0.072 Uiso 1 1 calc R . . . .
C5 C 0.6489(7) 0.2924(3) 0.12203(14) 0.0458(9) Uani 1 1 d . . . . .
C6 C 0.8656(8) 0.3014(4) 0.09844(17) 0.0658(13) Uani 1 1 d . . . . .
H6 H 0.970216 0.353141 0.108613 0.079 Uiso 1 1 calc R . . . .
C7 C 0.9275(8) 0.2349(4) 0.0603(2) 0.0699(14) Uani 1 1 d . . . . .
H7 H 1.072078 0.244332 0.044785 0.084 Uiso 1 1 calc R . . . .
C8 C 0.5667(6) 0.3612(3) 0.16179(15) 0.0446(10) Uani 1 1 d . . . . .
C9 C 0.6397(6) 0.4601(3) 0.17562(15) 0.0493(10) Uani 1 1 d . . . . .
C10 C 0.3357(7) 0.4082(3) 0.22173(14) 0.0443(9) Uani 1 1 d . . . . .
C11 C 0.1554(7) 0.4184(3) 0.25872(14) 0.0473(10) Uani 1 1 d . . . . .
C12 C -0.0110(7) 0.3402(4) 0.26661(15) 0.0565(12) Uani 1 1 d . . . . .
H12 H -0.004395 0.278613 0.248165 0.068 Uiso 1 1 calc R . . . .
C13 C -0.1850(8) 0.3537(5) 0.30150(17) 0.0680(14) Uani 1 1 d . . . . .
H13 H -0.295968 0.301355 0.306736 0.082 Uiso 1 1 calc R . . . .
C14 C -0.1942(9) 0.4464(5) 0.32909(18) 0.0779(16) Uani 1 1 d . . . . .
H14 H -0.313499 0.456005 0.352351 0.093 Uiso 1 1 calc R . . . .
C15 C -0.0305(8) 0.5230(4) 0.32231(18) 0.0701(14) Uani 1 1 d . . . . .
H15 H -0.036218 0.583087 0.341891 0.084 Uiso 1 1 calc R . . . .
C16 C 0.1465(8) 0.5127(4) 0.28626(16) 0.0545(11) Uani 1 1 d . . . . .
C17 C 0.3156(8) 0.5917(4) 0.27668(17) 0.0637(12) Uani 1 1 d . . . . .
H17 H 0.311906 0.652899 0.295475 0.076 Uiso 1 1 calc R . . . .
C18 C 0.4798(8) 0.5811(4) 0.24163(18) 0.0574(12) Uani 1 1 d . . . . .
H18 H 0.586311 0.634887 0.235577 0.069 Uiso 1 1 calc R . . . .
C19 C 0.2749(8) 0.8596(4) 0.03370(17) 0.0693(13) Uani 1 1 d . . . . .
H19A H 0.168972 0.896553 0.055311 0.104 Uiso 1 1 calc GR . . . .
H19B H 0.186822 0.823477 0.008495 0.104 Uiso 1 1 calc GR . . . .
H19C H 0.380035 0.908601 0.018205 0.104 Uiso 1 1 calc GR . . . .
C20 C 0.4138(7) 0.7819(3) 0.06356(16) 0.0497(11) Uani 1 1 d . . . . .
C21 C 0.3371(7) 0.6804(3) 0.06983(15) 0.0523(11) Uani 1 1 d . . . . .
H21 H 0.195540 0.660068 0.055470 0.063 Uiso 1 1 calc R . . . .
C22 C 0.4647(7) 0.6082(3) 0.09688(16) 0.0521(11) Uani 1 1 d . . . . .
H22 H 0.409596 0.539918 0.100026 0.062 Uiso 1 1 calc R . . . .
C23 C 0.6718(7) 0.6363(3) 0.11912(14) 0.0455(10) Uani 1 1 d . . . . .
C24 C 0.7511(7) 0.7381(3) 0.11384(16) 0.0542(12) Uani 1 1 d . . . . .
H24 H 0.890492 0.758671 0.129037 0.065 Uiso 1 1 calc R . . . .
C25 C 0.6250(7) 0.8087(3) 0.08632(16) 0.0545(11) Uani 1 1 d . . . . .
H25 H 0.682092 0.876551 0.082728 0.065 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C9 1.732(4) . ?
S1 C23 1.786(4) . ?
N1 C9 1.391(5) . ?
N1 C10 1.369(5) . ?
N1 C18 1.388(5) . ?
N2 C8 1.387(5) . ?
N2 C10 1.325(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.500(6) . ?
C2 C3 1.376(6) . ?
C2 C7 1.367(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(6) . ?
C5 C6 1.391(6) . ?
C5 C8 1.458(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.375(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(6) . ?
C10 C11 1.433(5) . ?
C11 C12 1.392(6) . ?
C11 C16 1.413(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.373(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.397(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.363(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.403(6) . ?
C16 C17 1.417(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.332(6) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C19 C20 1.501(6) . ?
C20 C21 1.377(5) . ?
C20 C25 1.391(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.380(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.369(5) . ?
C23 C24 1.383(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.368(5) . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 S1 C23 101.19(18) . . ?
C10 N1 C9 107.6(3) . . ?
C10 N1 C18 122.2(4) . . ?
C18 N1 C9 130.1(4) . . ?
C10 N2 C8 105.7(3) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 121.1(5) . . ?
C7 C2 C1 122.3(4) . . ?
C7 C2 C3 116.6(5) . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.0(5) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.9(4) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 116.9(4) . . ?
C4 C5 C8 118.5(4) . . ?
C6 C5 C8 124.6(4) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.0(5) . . ?
C7 C6 H6 119.5 . . ?
C2 C7 C6 122.6(4) . . ?
C2 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
N2 C8 C5 118.9(4) . . ?
C9 C8 N2 110.4(4) . . ?
C9 C8 C5 130.6(4) . . ?
N1 C9 S1 120.9(3) . . ?
C8 C9 S1 134.0(3) . . ?
C8 C9 N1 105.0(3) . . ?
N1 C10 C11 119.5(4) . . ?
N2 C10 N1 111.2(3) . . ?
N2 C10 C11 129.3(4) . . ?
C12 C11 C10 121.8(4) . . ?
C12 C11 C16 120.4(4) . . ?
C16 C11 C10 117.7(4) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.3(5) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.6(5) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.7(4) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C16 121.1(5) . . ?
C16 C15 H15 119.5 . . ?
C11 C16 C17 119.1(4) . . ?
C15 C16 C11 117.8(4) . . ?
C15 C16 C17 123.1(4) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 C16 122.1(5) . . ?
C18 C17 H17 118.9 . . ?
N1 C18 H18 120.4 . . ?
C17 C18 N1 119.3(4) . . ?
C17 C18 H18 120.4 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
C21 C20 C19 121.3(4) . . ?
C21 C20 C25 116.9(4) . . ?
C25 C20 C19 121.8(4) . . ?
C20 C21 H21 119.1 . . ?
C20 C21 C22 121.7(4) . . ?
C22 C21 H21 119.1 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.5(4) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 S1 122.9(3) . . ?
C22 C23 C24 118.8(4) . . ?
C24 C23 S1 118.2(3) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.2(4) . . ?
C25 C24 H24 119.9 . . ?
C20 C25 H25 119.1 . . ?
C24 C25 C20 121.9(4) . . ?
C24 C25 H25 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C23 C24 C25 177.4(3) . . . . ?
N1 C10 C11 C12 177.7(3) . . . . ?
N1 C10 C11 C16 -0.3(5) . . . . ?
N2 C8 C9 S1 -176.3(3) . . . . ?
N2 C8 C9 N1 -0.1(4) . . . . ?
N2 C10 C11 C12 -0.8(6) . . . . ?
N2 C10 C11 C16 -178.8(4) . . . . ?
C1 C2 C3 C4 -178.1(4) . . . . ?
C1 C2 C7 C6 179.3(4) . . . . ?
C2 C3 C4 C5 -0.8(7) . . . . ?
C3 C2 C7 C6 -0.3(7) . . . . ?
C3 C4 C5 C6 -1.2(7) . . . . ?
C3 C4 C5 C8 179.4(4) . . . . ?
C4 C5 C6 C7 2.3(7) . . . . ?
C4 C5 C8 N2 15.8(5) . . . . ?
C4 C5 C8 C9 -161.1(4) . . . . ?
C5 C6 C7 C2 -1.6(8) . . . . ?
C5 C8 C9 S1 0.9(7) . . . . ?
C5 C8 C9 N1 177.0(4) . . . . ?
C6 C5 C8 N2 -163.6(4) . . . . ?
C6 C5 C8 C9 19.5(7) . . . . ?
C7 C2 C3 C4 1.5(7) . . . . ?
C8 N2 C10 N1 -0.8(4) . . . . ?
C8 N2 C10 C11 177.9(4) . . . . ?
C8 C5 C6 C7 -178.3(4) . . . . ?
C9 S1 C23 C22 -29.7(4) . . . . ?
C9 S1 C23 C24 152.3(3) . . . . ?
C9 N1 C10 N2 0.7(4) . . . . ?
C9 N1 C10 C11 -178.1(3) . . . . ?
C9 N1 C18 C17 178.6(4) . . . . ?
C10 N1 C9 S1 176.5(3) . . . . ?
C10 N1 C9 C8 -0.4(4) . . . . ?
C10 N1 C18 C17 0.5(6) . . . . ?
C10 N2 C8 C5 -177.0(3) . . . . ?
C10 N2 C8 C9 0.5(4) . . . . ?
C10 C11 C12 C13 -178.3(4) . . . . ?
C10 C11 C16 C15 179.7(4) . . . . ?
C10 C11 C16 C17 -0.7(6) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
C11 C16 C17 C18 1.7(6) . . . . ?
C12 C11 C16 C15 1.7(6) . . . . ?
C12 C11 C16 C17 -178.7(4) . . . . ?
C12 C13 C14 C15 -1.0(7) . . . . ?
C13 C14 C15 C16 2.4(7) . . . . ?
C14 C15 C16 C11 -2.6(6) . . . . ?
C14 C15 C16 C17 177.8(4) . . . . ?
C15 C16 C17 C18 -178.7(4) . . . . ?
C16 C11 C12 C13 -0.4(6) . . . . ?
C16 C17 C18 N1 -1.6(7) . . . . ?
C18 N1 C9 S1 -1.9(6) . . . . ?
C18 N1 C9 C8 -178.7(4) . . . . ?
C18 N1 C10 N2 179.2(3) . . . . ?
C18 N1 C10 C11 0.4(5) . . . . ?
C19 C20 C21 C22 179.5(4) . . . . ?
C19 C20 C25 C24 179.5(4) . . . . ?
C20 C21 C22 C23 1.0(7) . . . . ?
C21 C20 C25 C24 -0.2(6) . . . . ?
C21 C22 C23 S1 -178.3(3) . . . . ?
C21 C22 C23 C24 -0.2(6) . . . . ?
C22 C23 C24 C25 -0.8(6) . . . . ?
C23 S1 C9 N1 -73.8(3) . . . . ?
C23 S1 C9 C8 102.0(4) . . . . ?
C23 C24 C25 C20 1.0(7) . . . . ?
C25 C20 C21 C22 -0.8(6) . . . . ?

_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 1.482
_oxdiff_exptl_absorpt_empirical_full_min 0.751
