# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_exp_1619
_database_code_depnum_ccdc_archive 'CCDC 2117471'
loop_
_audit_author_name
_audit_author_address
'Amrita Das'
;Osaka University
Japan
;
_audit_update_record             
;
2021-11-10 deposited with the CCDC.	2021-12-21 downloaded from the CCDC.
;
_audit_creation_date             2021-11-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 N3 O2'
_chemical_formula_sum            'C23 H17 N3 O2'
_chemical_formula_weight         367.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H17 N3 O2'
_chemical_oxdiff_usercomment     amrira-727_20210830_Cu
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'

_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                   14.6645(3)
_cell_length_b                   6.15540(10)
_cell_length_c                   20.4618(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.871(2)
_cell_angle_gamma                90
_cell_volume                     1757.88(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8927
_cell_measurement_temperature    123
_cell_measurement_theta_max      74.3460
_cell_measurement_theta_min      4.4250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.045
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17488
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.146
_diffrn_reflns_theta_min         3.281
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  21.00   0.50    0.36    --  -42.80  23.00 127.00  174
  2  ω    -60.00 -34.00   0.50    1.44    -- -106.00 103.00 179.82   52
  3  ω    -73.00 -47.00   0.50    1.44    -- -106.00 125.00 120.00   52
  4  ω    -70.00 -34.00   0.50    1.44    -- -106.00  77.00 150.00   72
  5  ω   -108.00 -82.00   0.50    1.44    -- -106.00  77.00 150.00   52
  6  ω   -116.00 -90.00   0.50    1.44    -- -106.00 125.00 120.00   52
  7  ω   -125.00 -74.00   0.50    1.44    -- -106.00 137.00  34.57  102
  8  ω    -89.00 -55.00   0.50    1.44    -- -106.00 125.00 -60.00   68
  9  ω    -69.00 -44.00   0.50    1.44    -- -106.00 125.00 -90.00   50
 10  ω    -87.00 -61.00   0.50    1.44    -- -106.00  77.00 -60.00   52
 11  ω    -63.00 -37.00   0.50    1.44    -- -106.00  57.00 -60.00   52
 12  ω    -89.00 -63.00   0.50    1.44    -- -106.00  37.00 -30.00   52
 13  ω   -120.00 -83.00   0.50    1.44    -- -106.00 -19.00  30.00   74
 14  ω   -121.00 -95.00   0.50    1.44    -- -106.00  37.00 -30.00   52
 15  ω   -122.00 -96.00   0.50    1.44    -- -106.00  57.00  30.00   52
 16  ω   -132.00 -64.00   0.50    1.44    -- -106.00  23.00 127.00  136
 17  ω    -93.00 -68.00   0.50    0.36    --  -42.80 -23.00 -37.00   50
 18  ω   -127.00 -87.00   0.50    1.44    -- -106.00  47.00 -82.82   80
 19  ω   -100.00 -33.00   0.50    1.44    -- -106.00  57.00-120.00  134
 20  ω    -93.00 -52.00   0.50    0.36    --  -42.80 125.00-150.00   82
 21  ω    -45.00 -10.00   0.50    0.36    --  -42.80 125.00-150.00   70
 22  ω    -63.00  31.00   0.50    0.36    --  -42.80  57.00-180.00  188
 23  ω     -8.00  18.00   0.50    0.36    --   42.80 -23.00 -37.00   52
 24  ω     26.00  51.00   0.50    1.44    --   76.50 -23.00 -37.00   50
 25  ω     60.00  85.00   0.50    0.36    --   42.80  23.00 127.00   50
 26  ω     78.00 103.00   0.50    1.44    --   76.50  23.00 127.00   50
 27  ω    -95.00 -65.00   0.50    1.44    -- -106.00  77.00-120.00   60
 28  ω   -135.00 -98.00   0.50    1.44    -- -106.00  77.00-120.00   74
 29  ω   -131.00 -57.00   0.50    1.44    -- -106.00  77.00 -90.00  148
 30  ω   -138.00-112.00   0.50    1.44    -- -106.00 -19.00-150.00   52
 31  ω   -176.00-118.00   0.50    1.44    -- -106.00 -23.00 -37.00  116
 32  ω   -173.00-146.00   0.50    1.44    -- -106.00 -19.00-150.00   54
 33  ω   -175.00 -83.00   0.50    1.44    -- -106.00 -37.00-120.00  184
 34  ω   -112.00 -70.00   0.50    0.36    --  -42.80-125.00 -90.00   84
 35  ω   -134.00-106.00   0.50    1.44    -- -106.00 -37.00  90.00   56
 36  ω   -118.00 -92.00   0.50    1.44    -- -106.00 -99.00  90.00   52
 37  ω   -153.00 -89.00   0.50    1.44    -- -106.00 -57.00  90.00  128
 38  ω   -154.00-116.00   0.50    1.44    -- -106.00 -37.00 120.00   76
 39  ω   -176.00-129.00   0.50    1.44    -- -106.00 -19.00  30.00   94
 40  ω   -164.00-139.00   0.50    1.44    -- -106.00 -99.00  90.00   50
 41  ω   -173.00-123.00   0.50    1.44    -- -106.00 -37.00-180.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0358986000
_diffrn_orient_matrix_UB_12      -0.0516890000
_diffrn_orient_matrix_UB_13      -0.0615742000
_diffrn_orient_matrix_UB_21      -0.1032171000
_diffrn_orient_matrix_UB_22      -0.0536210000
_diffrn_orient_matrix_UB_23      -0.0439276000
_diffrn_orient_matrix_UB_31      -0.0154201000
_diffrn_orient_matrix_UB_32      0.2389816000
_diffrn_orient_matrix_UB_33      -0.0231847000
_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'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3180
_reflns_number_total             3572
_reflns_odcompleteness_completeness 99.07
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3572
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.035
_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)+(0.0496P)²+0.5107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1002
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C7(H7), C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C20(H20), C14(H14), C22(H22), C18(H18), C19(H19), C10(H10),
 C17(H17), C13(H13), C23(H23), C12(H12), C25(H25), C11(H11), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O27 O 0.47902(6) 0.43203(14) 0.27209(4) 0.0303(2) Uani 1 1 d . . . . .
O28 O 0.45976(6) 0.72540(15) 0.47228(4) 0.0323(2) Uani 1 1 d . . . . .
N5 N 0.62669(7) 0.99835(16) 0.36643(5) 0.0249(2) Uani 1 1 d . . . . .
N1 N 0.44973(7) 0.55281(17) 0.37043(5) 0.0256(2) Uani 1 1 d . . . . .
N26 N 0.79538(7) 0.80023(18) 0.48082(5) 0.0301(2) Uani 1 1 d . . . . .
C9 C 0.35108(8) 0.4859(2) 0.35333(6) 0.0244(2) Uani 1 1 d . . . . .
C15 C 0.62176(8) 0.84194(19) 0.25709(6) 0.0236(2) Uani 1 1 d . . . . .
C21 C 0.73583(8) 0.9660(2) 0.48081(6) 0.0252(2) Uani 1 1 d . . . . .
C16 C 0.65315(8) 0.6658(2) 0.22674(6) 0.0265(3) Uani 1 1 d . . . . .
H16 H 0.666649 0.530954 0.250308 0.032 Uiso 1 1 calc R U . . .
C8 C 0.49724(8) 0.66478(19) 0.43053(6) 0.0255(2) Uani 1 1 d . . . . .
C20 C 0.59915(9) 1.0381(2) 0.22082(6) 0.0271(3) Uani 1 1 d . . . . .
H20 H 0.576457 1.158133 0.240548 0.033 Uiso 1 1 calc R U . . .
C3 C 0.60482(8) 0.61533(19) 0.36284(6) 0.0240(2) Uani 1 1 d . . . . .
H3 H 0.658137 0.510162 0.366517 0.029 Uiso 1 1 calc R U . . .
C2 C 0.50648(8) 0.51798(18) 0.32772(6) 0.0242(2) Uani 1 1 d . . . . .
C7 C 0.60087(8) 0.69338(19) 0.43303(6) 0.0245(2) Uani 1 1 d . . . . .
H7 H 0.644675 0.606248 0.471099 0.029 Uiso 1 1 calc R U . . .
C4 C 0.61775(8) 0.82895(19) 0.32839(6) 0.0234(2) Uani 1 1 d . . . . .
C6 C 0.63208(8) 0.93386(19) 0.43727(6) 0.0246(2) Uani 1 1 d . . . . .
H6 H 0.588418 1.025829 0.454806 0.030 Uiso 1 1 calc R U . . .
C14 C 0.33005(9) 0.2776(2) 0.37047(6) 0.0284(3) Uani 1 1 d . . . . .
H14 H 0.379971 0.180132 0.393132 0.034 Uiso 1 1 calc R U . . .
C22 C 0.76607(9) 1.1595(2) 0.51569(6) 0.0285(3) Uani 1 1 d . . . . .
H22 H 0.721954 1.273993 0.514008 0.034 Uiso 1 1 calc R U . . .
C18 C 0.64339(9) 0.8824(2) 0.12664(6) 0.0315(3) Uani 1 1 d . . . . .
H18 H 0.651571 0.896905 0.082558 0.038 Uiso 1 1 calc R U . . .
C19 C 0.61001(9) 1.0562(2) 0.15609(6) 0.0316(3) Uani 1 1 d . . . . .
H19 H 0.594422 1.189060 0.131582 0.038 Uiso 1 1 calc R U . . .
C10 C 0.27923(9) 0.6300(2) 0.32065(6) 0.0298(3) Uani 1 1 d . . . . .
H10 H 0.294756 0.771714 0.309070 0.036 Uiso 1 1 calc R U . . .
C17 C 0.66472(9) 0.6874(2) 0.16204(6) 0.0302(3) Uani 1 1 d . . . . .
H17 H 0.687356 0.567888 0.142018 0.036 Uiso 1 1 calc R U . . .
C13 C 0.23477(9) 0.2143(2) 0.35391(6) 0.0314(3) Uani 1 1 d . . . . .
H13 H 0.219349 0.071699 0.364827 0.038 Uiso 1 1 calc R U . . .
C23 C 0.86239(10) 1.1821(2) 0.55316(6) 0.0328(3) Uani 1 1 d . . . . .
H23 H 0.885399 1.312737 0.577292 0.039 Uiso 1 1 calc R U . . .
C12 C 0.16193(9) 0.3577(2) 0.32153(6) 0.0319(3) Uani 1 1 d . . . . .
H12 H 0.096901 0.313588 0.310769 0.038 Uiso 1 1 calc R U . . .
C25 C 0.88749(9) 0.8248(2) 0.51775(7) 0.0339(3) Uani 1 1 d . . . . .
H25 H 0.930258 0.708086 0.518727 0.041 Uiso 1 1 calc R U . . .
C11 C 0.18407(9) 0.5655(2) 0.30487(7) 0.0335(3) Uani 1 1 d . . . . .
H11 H 0.134198 0.663734 0.282698 0.040 Uiso 1 1 calc R U . . .
C24 C 0.92396(9) 1.0108(2) 0.55460(7) 0.0348(3) Uani 1 1 d . . . . .
H24 H 0.989867 1.020525 0.580318 0.042 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
O27 C2 1.2068(15) . ?
O28 C8 1.2080(15) . ?
N5 C4 1.2836(15) . ?
N5 C6 1.4814(15) . ?
N1 C9 1.4402(15) . ?
N1 C8 1.3953(15) . ?
N1 C2 1.3960(15) . ?
N26 C21 1.3431(16) . ?
N26 C25 1.3386(17) . ?
C9 C14 1.3886(17) . ?
C9 C10 1.3825(17) . ?
C15 C16 1.3957(17) . ?
C15 C20 1.4026(17) . ?
C15 C4 1.4802(16) . ?
C21 C6 1.5218(16) . ?
C21 C22 1.3894(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.3917(17) . ?
C8 C7 1.5150(16) . ?
C20 H20 0.9500 . ?
C20 C19 1.3861(17) . ?
C3 H3 1.0000 . ?
C3 C2 1.5228(16) . ?
C3 C7 1.5322(16) . ?
C3 C4 1.5310(16) . ?
C7 H7 1.0000 . ?
C7 C6 1.5440(16) . ?
C6 H6 1.0000 . ?
C14 H14 0.9500 . ?
C14 C13 1.3887(18) . ?
C22 H22 0.9500 . ?
C22 C23 1.3920(18) . ?
C18 H18 0.9500 . ?
C18 C19 1.3887(19) . ?
C18 C17 1.3871(19) . ?
C19 H19 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.3902(19) . ?
C17 H17 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.3872(19) . ?
C23 H23 0.9500 . ?
C23 C24 1.382(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.388(2) . ?
C25 H25 0.9500 . ?
C25 C24 1.385(2) . ?
C11 H11 0.9500 . ?
C24 H24 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N5 C6 109.91(10) . . ?
C8 N1 C9 123.24(10) . . ?
C8 N1 C2 113.28(10) . . ?
C2 N1 C9 123.46(10) . . ?
C25 N26 C21 117.23(11) . . ?
C14 C9 N1 119.15(11) . . ?
C10 C9 N1 119.58(11) . . ?
C10 C9 C14 121.27(11) . . ?
C16 C15 C20 119.32(11) . . ?
C16 C15 C4 120.99(11) . . ?
C20 C15 C4 119.59(10) . . ?
N26 C21 C6 115.75(10) . . ?
N26 C21 C22 123.11(11) . . ?
C22 C21 C6 121.09(11) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.16(11) . . ?
C17 C16 H16 119.9 . . ?
O28 C8 N1 124.28(11) . . ?
O28 C8 C7 127.56(11) . . ?
N1 C8 C7 108.15(10) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 C15 119.81(11) . . ?
C19 C20 H20 120.1 . . ?
C2 C3 H3 112.7 . . ?
C2 C3 C7 105.25(9) . . ?
C2 C3 C4 110.72(9) . . ?
C7 C3 H3 112.7 . . ?
C4 C3 H3 112.7 . . ?
C4 C3 C7 102.00(9) . . ?
O27 C2 N1 124.56(11) . . ?
O27 C2 C3 127.68(11) . . ?
N1 C2 C3 107.72(9) . . ?
C8 C7 C3 104.95(9) . . ?
C8 C7 H7 111.2 . . ?
C8 C7 C6 112.97(10) . . ?
C3 C7 H7 111.2 . . ?
C3 C7 C6 104.92(9) . . ?
C6 C7 H7 111.2 . . ?
N5 C4 C15 121.75(11) . . ?
N5 C4 C3 114.99(10) . . ?
C15 C4 C3 123.24(10) . . ?
N5 C6 C21 106.35(9) . . ?
N5 C6 C7 106.02(9) . . ?
N5 C6 H6 110.6 . . ?
C21 C6 C7 112.55(10) . . ?
C21 C6 H6 110.6 . . ?
C7 C6 H6 110.6 . . ?
C9 C14 H14 120.6 . . ?
C13 C14 C9 118.83(12) . . ?
C13 C14 H14 120.6 . . ?
C21 C22 H22 120.7 . . ?
C21 C22 C23 118.57(12) . . ?
C23 C22 H22 120.7 . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.54(11) . . ?
C20 C19 C18 120.78(12) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.41(12) . . ?
C11 C10 H10 120.3 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.36(11) . . ?
C18 C17 H17 119.8 . . ?
C14 C13 H13 119.7 . . ?
C12 C13 C14 120.51(12) . . ?
C12 C13 H13 119.7 . . ?
C22 C23 H23 120.6 . . ?
C24 C23 C22 118.79(12) . . ?
C24 C23 H23 120.6 . . ?
C13 C12 H12 120.0 . . ?
C13 C12 C11 119.99(12) . . ?
C11 C12 H12 120.0 . . ?
N26 C25 H25 118.1 . . ?
N26 C25 C24 123.71(13) . . ?
C24 C25 H25 118.1 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.98(12) . . ?
C12 C11 H11 120.0 . . ?
C23 C24 C25 118.57(12) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 H24 120.7 . . ?

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
O28 C8 C7 C3 -172.14(12) . . . . ?
O28 C8 C7 C6 -58.39(16) . . . . ?
N1 C9 C14 C13 179.91(11) . . . . ?
N1 C9 C10 C11 -179.33(11) . . . . ?
N1 C8 C7 C3 8.04(13) . . . . ?
N1 C8 C7 C6 121.78(11) . . . . ?
N26 C21 C6 N5 -84.75(12) . . . . ?
N26 C21 C6 C7 30.92(14) . . . . ?
N26 C21 C22 C23 -0.81(18) . . . . ?
N26 C25 C24 C23 -0.4(2) . . . . ?
C9 N1 C8 O28 -3.64(19) . . . . ?
C9 N1 C8 C7 176.18(10) . . . . ?
C9 N1 C2 O27 1.15(19) . . . . ?
C9 N1 C2 C3 178.83(10) . . . . ?
C9 C14 C13 C12 -0.75(18) . . . . ?
C9 C10 C11 C12 -0.43(19) . . . . ?
C15 C16 C17 C18 -1.28(18) . . . . ?
C15 C20 C19 C18 -0.22(18) . . . . ?
C21 N26 C25 C24 -0.84(19) . . . . ?
C21 C22 C23 C24 -0.46(18) . . . . ?
C16 C15 C20 C19 -1.29(17) . . . . ?
C16 C15 C4 N5 151.97(11) . . . . ?
C16 C15 C4 C3 -26.78(16) . . . . ?
C8 N1 C9 C14 -94.40(14) . . . . ?
C8 N1 C9 C10 85.21(15) . . . . ?
C8 N1 C2 O27 -177.06(11) . . . . ?
C8 N1 C2 C3 0.63(13) . . . . ?
C8 C7 C6 N5 -99.02(11) . . . . ?
C8 C7 C6 C21 145.12(10) . . . . ?
C20 C15 C16 C17 2.03(17) . . . . ?
C20 C15 C4 N5 -24.20(16) . . . . ?
C20 C15 C4 C3 157.04(11) . . . . ?
C3 C7 C6 N5 14.75(11) . . . . ?
C3 C7 C6 C21 -101.12(11) . . . . ?
C2 N1 C9 C14 87.57(14) . . . . ?
C2 N1 C9 C10 -92.82(14) . . . . ?
C2 N1 C8 O28 174.57(11) . . . . ?
C2 N1 C8 C7 -5.60(14) . . . . ?
C2 C3 C7 C8 -7.44(12) . . . . ?
C2 C3 C7 C6 -126.73(10) . . . . ?
C2 C3 C4 N5 115.28(11) . . . . ?
C2 C3 C4 C15 -65.89(13) . . . . ?
C7 C3 C2 O27 -177.92(12) . . . . ?
C7 C3 C2 N1 4.49(12) . . . . ?
C7 C3 C4 N5 3.69(13) . . . . ?
C7 C3 C4 C15 -177.47(10) . . . . ?
C4 N5 C6 C21 106.91(11) . . . . ?
C4 N5 C6 C7 -13.09(12) . . . . ?
C4 C15 C16 C17 -174.16(10) . . . . ?
C4 C15 C20 C19 174.95(11) . . . . ?
C4 C3 C2 O27 72.60(15) . . . . ?
C4 C3 C2 N1 -105.00(11) . . . . ?
C4 C3 C7 C8 108.21(10) . . . . ?
C4 C3 C7 C6 -11.08(11) . . . . ?
C6 N5 C4 C15 -172.88(10) . . . . ?
C6 N5 C4 C3 5.97(13) . . . . ?
C6 C21 C22 C23 -178.20(11) . . . . ?
C14 C9 C10 C11 0.28(18) . . . . ?
C14 C13 C12 C11 0.61(19) . . . . ?
C22 C21 C6 N5 92.82(12) . . . . ?
C22 C21 C6 C7 -151.51(11) . . . . ?
C22 C23 C24 C25 1.02(19) . . . . ?
C19 C18 C17 C16 -0.24(19) . . . . ?
C10 C9 C14 C13 0.31(18) . . . . ?
C17 C18 C19 C20 0.98(19) . . . . ?
C13 C12 C11 C10 -0.01(19) . . . . ?
C25 N26 C21 C6 178.96(11) . . . . ?
C25 N26 C21 C22 1.44(18) . . . . ?

_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 2.048
_oxdiff_exptl_absorpt_empirical_full_min 0.647
####################################################################### 
# 
# 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_exp_1618
_database_code_depnum_ccdc_archive 'CCDC 2117470'
loop_
_audit_author_name
_audit_author_address
'Amrita Das'
;Osaka University
Japan
;
_audit_update_record             
;
2021-11-11 deposited with the CCDC.	2021-12-21 downloaded from the CCDC.
;
_audit_creation_date             2021-08-30
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 N3 O2 S'
_chemical_formula_sum            'C16 H13 N3 O2 S'
_chemical_formula_weight         311.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H13 N3 O2 S'
_chemical_oxdiff_usercomment     amrita-722_20210830_Cu
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.7589(2)
_cell_length_b                   7.74990(10)
_cell_length_c                   16.8477(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.056(2)
_cell_angle_gamma                90
_cell_volume                     1383.19(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7390
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1190
_cell_measurement_theta_min      4.5440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.182
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear Yellow'
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.182
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12816
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.282
_diffrn_reflns_theta_min         4.543
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     13.00 116.00   0.50    0.13    --   42.80  80.00   1.00  206
  2  ω     74.00  99.00   0.50    0.53    --   76.50  80.00   1.00   50
  3  ω     71.00 114.00   0.50    0.13    --   42.80 125.00  30.00   86
  4  ω     -7.00  22.00   0.50    0.13    --   42.80 -80.00-121.00   58
  5  ω     44.00  70.00   0.50    0.13    --   42.80 -80.00-121.00   52
  6  ω     30.00  55.00   0.50    0.53    --   76.50 -80.00-121.00   50
  7  ω    -54.00 -14.00   0.50    0.13    --  -42.80 -80.00-121.00   80
  8  ω   -105.00 -76.00   0.50    0.53    -- -106.00 -80.00-121.00   58
  9  ω   -117.00 -92.00   0.50    0.53    -- -106.00 -37.00 -60.00   50
 10  ω   -109.00 -76.00   0.50    0.53    -- -106.00 -19.00 -90.00   66
 11  ω    -88.00 -55.00   0.50    0.53    -- -106.00  57.00   0.00   66
 12  ω    -67.00 -42.00   0.50    0.53    -- -106.00  77.00  30.00   50
 13  ω    -78.00 -46.00   0.50    0.53    -- -106.00  57.00 -30.00   64
 14  ω    -84.00 -34.00   0.50    0.53    -- -106.00  77.00 -60.00  100
 15  ω    -82.00 -56.00   0.50    0.53    -- -106.00  77.00   0.00   52
 16  ω   -108.00 -83.00   0.50    0.53    -- -106.00  80.00   1.00   50
 17  ω   -103.00 -77.00   0.50    0.53    -- -106.00  37.00   0.00   52
 18  ω   -128.00 -96.00   0.50    0.53    -- -106.00  57.00   0.00   64
 19  ω   -128.00 -33.00   0.50    0.53    -- -106.00  77.00  60.00  190
 20  ω    -74.00 -45.00   0.50    0.53    -- -106.00 125.00 150.00   58
 21  ω   -115.00 -87.00   0.50    0.53    -- -106.00 125.00 150.00   56
 22  ω   -117.00 -89.00   0.50    0.53    -- -106.00 125.00  60.00   56
 23  ω    -92.00 -48.00   0.50    0.13    --  -42.80 125.00 -30.00   88
 24  ω   -112.00 -82.00   0.50    0.53    -- -106.00 125.00-120.00   60
 25  ω   -131.00 -50.00   0.50    0.53    -- -106.00  77.00-180.00  162
 26  ω   -157.00-131.00   0.50    0.53    -- -106.00 -19.00 -90.00   52
 27  ω   -165.00 -83.00   0.50    0.53    -- -106.00 -57.00-120.00  164
 28  ω   -128.00-103.00   0.50    0.53    -- -106.00 -77.00 -60.00   50
 29  ω   -116.00 -70.00   0.50    0.13    --  -42.80-125.00   0.00   92
 30  ω   -134.00 -78.00   0.50    0.53    -- -106.00 -77.00  90.00  112
 31  ω   -109.00 -83.00   0.50    0.53    -- -106.00 -77.00 150.00   52
 32  ω   -129.00-102.00   0.50    0.53    -- -106.00 -99.00  90.00   54
 33  ω   -161.00 -86.00   0.50    0.53    -- -106.00 -37.00  90.00  150
 34  ω   -172.00-147.00   0.50    0.53    -- -106.00 -77.00  90.00   50
 35  ω   -173.00-148.00   0.50    0.53    -- -106.00 -57.00 150.00   50
 36  ω   -177.00-117.00   0.50    0.53    -- -106.00 -80.00-121.00  120
 37  ω   -176.00-126.00   0.50    0.53    -- -106.00 -77.00-150.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0856731000
_diffrn_orient_matrix_UB_12      -0.0844033000
_diffrn_orient_matrix_UB_13      -0.0724304000
_diffrn_orient_matrix_UB_21      -0.0953905000
_diffrn_orient_matrix_UB_22      0.1488433000
_diffrn_orient_matrix_UB_23      -0.0015301000
_diffrn_orient_matrix_UB_31      0.0686916000
_diffrn_orient_matrix_UB_32      0.1012264000
_diffrn_orient_matrix_UB_33      -0.0580592000
_diffrn_oxdiff_ac3_digest_frames 
;
0112d4bcda60f4f4b99426578b1b0fd37b00081e26c
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01b6651a2bd0c3d81b098b0780eb9e6b5105b4
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2596
_reflns_number_total             2804
_reflns_odcompleteness_completeness 99.05
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2804
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.057
_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)+(0.0531P)²+0.5038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.0976
_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 Ternary CH refined with riding coordinates:
 C7(H7), C2(H2), C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C18(H18), C12(H12), C11(H11), C17(H17), C16(H16), C13(H13)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S9 S 0.62205(3) 0.31961(5) 0.57649(2) 0.02088(13) Uani 1 1 d . . . . .
O21 O 0.32031(9) 0.28684(15) 0.30957(6) 0.0239(2) Uani 1 1 d . . . . .
O20 O -0.03637(9) 0.35041(15) 0.41675(6) 0.0264(2) Uani 1 1 d . . . . .
N8 N 0.33642(11) 0.30216(15) 0.56574(7) 0.0188(3) Uani 1 1 d . . . . .
N4 N 0.13449(10) 0.34801(16) 0.35207(7) 0.0189(3) Uani 1 1 d . . . . .
N19 N 0.03415(11) 0.16200(16) 0.61920(7) 0.0210(3) Uani 1 1 d . . . . .
C14 C 0.15829(13) 0.19249(17) 0.62688(8) 0.0173(3) Uani 1 1 d . . . . .
C7 C 0.19863(12) 0.28331(18) 0.55558(8) 0.0171(3) Uani 1 1 d . . . . .
H7 H 0.161491 0.399127 0.551666 0.021 Uiso 1 1 calc R . . . .
C1 C 0.37674(12) 0.24458(17) 0.50365(8) 0.0172(3) Uani 1 1 d . . . . .
C3 C 0.25228(12) 0.27175(19) 0.35933(8) 0.0179(3) Uani 1 1 d . . . . .
C2 C 0.27621(12) 0.16923(17) 0.43770(8) 0.0169(3) Uani 1 1 d . . . . .
H2 H 0.293103 0.047555 0.427839 0.020 Uiso 1 1 calc R . . . .
C5 C 0.06920(13) 0.30324(18) 0.41356(8) 0.0185(3) Uani 1 1 d . . . . .
C6 C 0.15495(12) 0.19018(17) 0.47338(8) 0.0171(3) Uani 1 1 d . . . . .
H6 H 0.115811 0.078420 0.480629 0.020 Uiso 1 1 calc R . . . .
C15 C 0.24332(13) 0.1521(2) 0.69611(9) 0.0227(3) Uani 1 1 d . . . . .
H15 H 0.328981 0.174195 0.699138 0.027 Uiso 1 1 calc R . . . .
C10 C 0.50999(12) 0.24554(17) 0.49737(8) 0.0179(3) Uani 1 1 d . . . . .
C18 C -0.00706(13) 0.0910(2) 0.68281(9) 0.0226(3) Uani 1 1 d . . . . .
H18 H -0.093085 0.069842 0.678303 0.027 Uiso 1 1 calc R . . . .
C12 C 0.69883(13) 0.2123(2) 0.44979(9) 0.0230(3) Uani 1 1 d . . . . .
H12 H 0.750780 0.183255 0.413144 0.028 Uiso 1 1 calc R . . . .
C11 C 0.56594(13) 0.19153(19) 0.43399(9) 0.0209(3) Uani 1 1 d . . . . .
H11 H 0.521410 0.146473 0.386201 0.025 Uiso 1 1 calc R . . . .
C17 C 0.07040(14) 0.0477(2) 0.75433(9) 0.0246(3) Uani 1 1 d . . . . .
H17 H 0.037518 -0.000323 0.796818 0.030 Uiso 1 1 calc R . . . .
C16 C 0.19899(14) 0.0783(2) 0.76073(9) 0.0253(3) Uani 1 1 d . . . . .
H16 H 0.254457 0.049689 0.807632 0.030 Uiso 1 1 calc R . . . .
C13 C 0.74267(13) 0.2793(2) 0.52413(9) 0.0225(3) Uani 1 1 d . . . . .
H13 H 0.827416 0.300535 0.544151 0.027 Uiso 1 1 calc R . . . .
C22 C 0.08304(14) 0.4568(2) 0.28388(9) 0.0258(3) Uani 1 1 d . . . . .
H22A H 0.142755 0.545641 0.277579 0.039 Uiso 1 1 calc GR . . . .
H22B H 0.005843 0.508599 0.293242 0.039 Uiso 1 1 calc GR . . . .
H22C H 0.066580 0.388037 0.235796 0.039 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
S9 C10 1.7317(14) . ?
S9 C13 1.7203(14) . ?
O21 C3 1.2109(17) . ?
O20 C5 1.2033(17) . ?
N8 C7 1.4695(17) . ?
N8 C1 1.2806(18) . ?
N4 C3 1.3843(17) . ?
N4 C5 1.3933(17) . ?
N4 C22 1.4545(18) . ?
N19 C14 1.3402(18) . ?
N19 C18 1.3465(19) . ?
C14 C7 1.5195(18) . ?
C14 C15 1.387(2) . ?
C7 H7 0.9800 . ?
C7 C6 1.5596(18) . ?
C1 C2 1.5251(18) . ?
C1 C10 1.4559(18) . ?
C3 C2 1.5239(19) . ?
C2 H2 0.9800 . ?
C2 C6 1.5374(17) . ?
C5 C6 1.5198(19) . ?
C6 H6 0.9800 . ?
C15 H15 0.9300 . ?
C15 C16 1.386(2) . ?
C10 C11 1.379(2) . ?
C18 H18 0.9300 . ?
C18 C17 1.381(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.4171(19) . ?
C12 C13 1.362(2) . ?
C11 H11 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.389(2) . ?
C16 H16 0.9300 . ?
C13 H13 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 S9 C10 91.79(7) . . ?
C1 N8 C7 110.42(11) . . ?
C3 N4 C5 113.62(11) . . ?
C3 N4 C22 122.24(11) . . ?
C5 N4 C22 124.06(12) . . ?
C14 N19 C18 117.15(12) . . ?
N19 C14 C7 115.02(12) . . ?
N19 C14 C15 122.77(13) . . ?
C15 C14 C7 122.14(12) . . ?
N8 C7 C14 112.06(11) . . ?
N8 C7 H7 107.9 . . ?
N8 C7 C6 106.91(10) . . ?
C14 C7 H7 107.9 . . ?
C14 C7 C6 113.84(11) . . ?
C6 C7 H7 107.9 . . ?
N8 C1 C2 115.48(11) . . ?
N8 C1 C10 122.41(12) . . ?
C10 C1 C2 122.08(12) . . ?
O21 C3 N4 123.53(13) . . ?
O21 C3 C2 128.25(12) . . ?
N4 C3 C2 108.22(11) . . ?
C1 C2 H2 111.3 . . ?
C1 C2 C6 102.53(10) . . ?
C3 C2 C1 115.01(11) . . ?
C3 C2 H2 111.3 . . ?
C3 C2 C6 104.91(11) . . ?
C6 C2 H2 111.3 . . ?
O20 C5 N4 124.05(13) . . ?
O20 C5 C6 127.88(12) . . ?
N4 C5 C6 108.07(11) . . ?
C7 C6 H6 111.6 . . ?
C2 C6 C7 104.56(10) . . ?
C2 C6 H6 111.6 . . ?
C5 C6 C7 112.08(11) . . ?
C5 C6 C2 105.07(11) . . ?
C5 C6 H6 111.6 . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.14(13) . . ?
C16 C15 H15 120.4 . . ?
C1 C10 S9 120.52(10) . . ?
C11 C10 S9 110.93(10) . . ?
C11 C10 C1 128.55(13) . . ?
N19 C18 H18 117.9 . . ?
N19 C18 C17 124.13(13) . . ?
C17 C18 H18 117.9 . . ?
C11 C12 H12 123.5 . . ?
C13 C12 H12 123.5 . . ?
C13 C12 C11 113.10(13) . . ?
C10 C11 C12 112.48(13) . . ?
C10 C11 H11 123.8 . . ?
C12 C11 H11 123.8 . . ?
C18 C17 H17 121.1 . . ?
C18 C17 C16 117.86(13) . . ?
C16 C17 H17 121.1 . . ?
C15 C16 C17 118.94(13) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
S9 C13 H13 124.2 . . ?
C12 C13 S9 111.70(10) . . ?
C12 C13 H13 124.2 . . ?
N4 C22 H22A 109.5 . . ?
N4 C22 H22B 109.5 . . ?
N4 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 1.997
_oxdiff_exptl_absorpt_empirical_full_min 0.579
