# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_nks-rnb-197b_auto
_database_code_depnum_ccdc_archive 'CCDC 2220553'
loop_
_audit_author_name
_audit_author_address
'Nagendra Sharma'
;School of Chemical Sciences, National Institute of science Education and Research (NISER)Bhubaneswar
India
;
_audit_update_record             
;
2022-11-18 deposited with the CCDC.	2023-01-05 downloaded from the CCDC.
;
_audit_creation_date             2022-08-05
_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         '0.182(C20 H17 Cl N2 O2 Se)'
_chemical_formula_sum            'C3.64 H3.09 Cl0.18 N0.36 O0.36 Se0.18'
_chemical_formula_weight         78.50
_chemical_melting_point          ?
_chemical_oxdiff_formula         ' Cl C H N O Se '
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'
Cl Cl 0.1484 0.1585 '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'
Se Se -0.0929 2.2259 '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                   7.9413(5)
_cell_length_b                   8.6162(7)
_cell_length_c                   15.5382(11)
_cell_angle_alpha                89.406(6)
_cell_angle_beta                 81.894(6)
_cell_angle_gamma                62.946(7)
_cell_volume                     935.64(13)
_cell_formula_units_Z            11
_cell_measurement_reflns_used    6434
_cell_measurement_temperature    295(4)
_cell_measurement_theta_max      28.8680
_cell_measurement_theta_min      3.6250
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    2.166
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.52a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.001
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_av_unetI/netI     0.0717
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.794
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16304
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.794
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.406
_diffrn_reflns_theta_min         3.314
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.794
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  59.00   0.50   45.76    --   -4.14  67.00-172.00  160
  2  ω    -67.00  13.00   0.50   45.76    --   -4.14 -67.00  53.00  160
  3  ω      0.00  70.00   0.50   45.76    --    3.51  37.00 -30.00  140
  4  ω    -13.00  66.00   0.50   45.76    --    3.51  67.00-172.00  158
  5  ω     -8.00  66.00   0.50   45.76    --    3.51  57.00  30.00  148
  6  ω    -70.00  -1.00   0.50   45.76    --   -4.14 -37.00 150.00  138
  7  ω     -7.00  55.00   0.50   45.76    --   -4.14  37.00 120.00  124
  8  ω    -14.00  13.00   0.50   45.76    --   -4.14 -99.00-150.00   54
  9  ω    -15.00  32.00   0.50   45.76    --   -4.14 -99.00 -90.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0323950000
_diffrn_orient_matrix_UB_12      0.0537725000
_diffrn_orient_matrix_UB_13      0.0192314000
_diffrn_orient_matrix_UB_21      -0.0423883000
_diffrn_orient_matrix_UB_22      0.0650710000
_diffrn_orient_matrix_UB_23      -0.0294246000
_diffrn_orient_matrix_UB_31      -0.0863343000
_diffrn_orient_matrix_UB_32      0.0380844000
_diffrn_orient_matrix_UB_33      0.0299752000
_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                2679
_reflns_number_total             4500
_reflns_odcompleteness_completeness 99.40
_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 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4500
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1220
_refine_ls_R_factor_gt           0.0696
_refine_ls_restrained_S_all      1.041
_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)+(0.0736P)²+1.6751P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1674
_refine_ls_wR_factor_ref         0.1865
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C10(H10), C12(H12), C11(H11), C15(H15), C5(H5), C16(H16), C4(H4),
 C18(H18), C17(H17), C2(H2A), C3(H3)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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
Se1 Se 0.75725(8) 0.84063(9) 0.64624(4) 0.0648(3) Uani 1 1 d . . . . .
Cl1 Cl 0.8035(2) 0.2097(2) 0.52351(12) 0.0724(5) Uani 1 1 d . . . . .
N2 N 0.6334(6) 0.4789(6) 0.7191(3) 0.0512(11) Uani 1 1 d . . . . .
H2 H 0.552296 0.457781 0.696716 0.061 Uiso 1 1 calc R U . . .
N1 N 0.2792(7) 0.5536(7) 0.7951(3) 0.0633(13) Uani 1 1 d . . . . .
O2 O 0.6110(7) 1.0483(7) 0.8059(3) 0.0883(15) Uani 1 1 d . . . . .
O1 O 0.6991(6) 0.5594(8) 0.8422(3) 0.0942(18) Uani 1 1 d . . . . .
C8 C 0.7760(6) 0.5202(7) 0.5759(3) 0.0417(11) Uani 1 1 d . . . . .
C9 C 0.7715(6) 0.4204(7) 0.5078(3) 0.0467(12) Uani 1 1 d . . . . .
C6 C 0.5889(7) 0.5382(8) 0.8018(3) 0.0551(14) Uani 1 1 d . . . . .
C14 C 0.4996(8) 0.9307(7) 0.7061(3) 0.0512(12) Uani 1 1 d . . . . .
C13 C 0.7479(7) 0.6883(7) 0.5588(3) 0.0462(12) Uani 1 1 d . . . . .
C10 C 0.7429(7) 0.4825(8) 0.4250(3) 0.0525(13) Uani 1 1 d . . . . .
H10 H 0.742060 0.412022 0.380310 0.063 Uiso 1 1 calc R U . . .
C1 C 0.3885(7) 0.5798(8) 0.8437(3) 0.0537(13) Uani 1 1 d . . . . .
C12 C 0.7151(8) 0.7542(8) 0.4766(3) 0.0545(13) Uani 1 1 d . . . . .
H12 H 0.692898 0.868066 0.466733 0.065 Uiso 1 1 calc R U . . .
C7 C 0.8118(7) 0.4473(8) 0.6638(3) 0.0529(13) Uani 1 1 d . . . . .
H7A H 0.895936 0.322680 0.656347 0.063 Uiso 1 1 calc R U . . .
H7B H 0.875264 0.501218 0.692034 0.063 Uiso 1 1 calc R U . . .
C19 C 0.4612(9) 1.0298(9) 0.7829(4) 0.0655(16) Uani 1 1 d . . . . .
C11 C 0.7164(8) 0.6476(8) 0.4106(3) 0.0582(15) Uani 1 1 d . . . . .
H11 H 0.698804 0.689209 0.355376 0.070 Uiso 1 1 calc R U . . .
C15 C 0.3548(8) 0.9120(8) 0.6771(4) 0.0580(14) Uani 1 1 d . . . . .
H15 H 0.380760 0.846278 0.625415 0.070 Uiso 1 1 calc R U . . .
C5 C 0.1045(9) 0.5872(10) 0.8308(4) 0.0751(19) Uani 1 1 d . . . . .
H5 H 0.028057 0.567847 0.796554 0.090 Uiso 1 1 calc R U . . .
C16 C 0.1726(9) 0.9874(9) 0.7221(5) 0.0741(18) Uani 1 1 d . . . . .
H16 H 0.076413 0.971943 0.701610 0.089 Uiso 1 1 calc R U . . .
C4 C 0.0301(10) 0.6479(12) 0.9142(4) 0.087(2) Uani 1 1 d . . . . .
H4 H -0.095558 0.674542 0.936543 0.105 Uiso 1 1 calc R U . . .
C18 C 0.2768(12) 1.1088(11) 0.8284(5) 0.097(3) Uani 1 1 d . . . . .
H18 H 0.248667 1.177105 0.879434 0.117 Uiso 1 1 calc R U . . .
C17 C 0.1340(10) 1.0849(10) 0.7971(5) 0.086(2) Uani 1 1 d . . . . .
H17 H 0.010407 1.136558 0.827858 0.103 Uiso 1 1 calc R U . . .
C2 C 0.3285(11) 0.6376(14) 0.9274(4) 0.104(3) Uani 1 1 d . . . . .
H2A H 0.407812 0.656414 0.960035 0.125 Uiso 1 1 calc R U . . .
C20 C 0.6018(14) 1.1058(13) 0.8906(5) 0.106(3) Uani 1 1 d . . . . .
H20A H 0.719572 1.107587 0.896547 0.160 Uiso 1 1 calc R U . . .
H20B H 0.581786 1.028130 0.930687 0.160 Uiso 1 1 calc R U . . .
H20C H 0.497661 1.221270 0.902875 0.160 Uiso 1 1 calc R U . . .
C3 C 0.1469(13) 0.6686(16) 0.9643(5) 0.127(4) Uani 1 1 d . . . . .
H3 H 0.104371 0.703449 1.023039 0.153 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
Se1 C14 1.920(5) . ?
Se1 C13 1.931(5) . ?
Cl1 C9 1.734(6) . ?
N2 H2 0.8600 . ?
N2 C6 1.326(7) . ?
N2 C7 1.460(6) . ?
N1 C1 1.320(7) . ?
N1 C5 1.318(7) . ?
O2 C19 1.364(7) . ?
O2 C20 1.391(8) . ?
O1 C6 1.223(6) . ?
C8 C9 1.385(7) . ?
C8 C13 1.390(7) . ?
C8 C7 1.507(7) . ?
C9 C10 1.397(8) . ?
C6 C1 1.510(7) . ?
C14 C19 1.388(8) . ?
C14 C15 1.367(8) . ?
C13 C12 1.402(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.361(8) . ?
C1 C2 1.337(8) . ?
C12 H12 0.9300 . ?
C12 C11 1.380(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C19 C18 1.386(10) . ?
C11 H11 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.369(8) . ?
C5 H5 0.9300 . ?
C5 C4 1.348(9) . ?
C16 H16 0.9300 . ?
C16 C17 1.357(10) . ?
C4 H4 0.9300 . ?
C4 C3 1.362(10) . ?
C18 H18 0.9300 . ?
C18 C17 1.391(11) . ?
C17 H17 0.9300 . ?
C2 H2A 0.9300 . ?
C2 C3 1.378(10) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C3 H3 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
C14 Se1 C13 98.9(2) . . ?
C6 N2 H2 118.1 . . ?
C6 N2 C7 123.9(4) . . ?
C7 N2 H2 118.1 . . ?
C5 N1 C1 118.3(5) . . ?
C19 O2 C20 119.9(6) . . ?
C9 C8 C13 116.9(5) . . ?
C9 C8 C7 120.9(5) . . ?
C13 C8 C7 122.2(4) . . ?
C8 C9 Cl1 120.0(4) . . ?
C8 C9 C10 122.4(5) . . ?
C10 C9 Cl1 117.6(4) . . ?
N2 C6 C1 114.8(4) . . ?
O1 C6 N2 123.7(5) . . ?
O1 C6 C1 121.5(5) . . ?
C19 C14 Se1 115.0(4) . . ?
C15 C14 Se1 125.5(4) . . ?
C15 C14 C19 119.3(5) . . ?
C8 C13 Se1 121.7(4) . . ?
C8 C13 C12 121.5(5) . . ?
C12 C13 Se1 116.7(4) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.1(5) . . ?
C11 C10 H10 120.4 . . ?
N1 C1 C6 117.4(5) . . ?
N1 C1 C2 122.3(5) . . ?
C2 C1 C6 120.3(5) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 C13 119.1(5) . . ?
C11 C12 H12 120.5 . . ?
N2 C7 C8 111.3(4) . . ?
N2 C7 H7A 109.4 . . ?
N2 C7 H7B 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
O2 C19 C14 116.0(5) . . ?
O2 C19 C18 124.5(6) . . ?
C18 C19 C14 119.4(6) . . ?
C10 C11 C12 121.0(5) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C14 C15 H15 119.1 . . ?
C14 C15 C16 121.7(6) . . ?
C16 C15 H15 119.1 . . ?
N1 C5 H5 118.1 . . ?
N1 C5 C4 123.8(6) . . ?
C4 C5 H5 118.1 . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.2(6) . . ?
C17 C16 H16 120.4 . . ?
C5 C4 H4 121.4 . . ?
C5 C4 C3 117.1(6) . . ?
C3 C4 H4 121.4 . . ?
C19 C18 H18 120.3 . . ?
C19 C18 C17 119.4(6) . . ?
C17 C18 H18 120.3 . . ?
C16 C17 C18 120.9(6) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C1 C2 H2A 120.7 . . ?
C1 C2 C3 118.7(6) . . ?
C3 C2 H2A 120.7 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C4 C3 C2 119.7(6) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se1 C14 C19 O2 -0.7(8) . . . . ?
Se1 C14 C19 C18 176.4(6) . . . . ?
Se1 C14 C15 C16 -176.9(5) . . . . ?
Se1 C13 C12 C11 176.9(4) . . . . ?
Cl1 C9 C10 C11 179.7(4) . . . . ?
N2 C6 C1 N1 0.1(8) . . . . ?
N2 C6 C1 C2 178.8(7) . . . . ?
N1 C1 C2 C3 0.8(14) . . . . ?
N1 C5 C4 C3 -2.6(14) . . . . ?
O2 C19 C18 C17 177.9(7) . . . . ?
O1 C6 C1 N1 179.7(6) . . . . ?
O1 C6 C1 C2 -1.6(11) . . . . ?
C8 C9 C10 C11 -0.8(7) . . . . ?
C8 C13 C12 C11 -1.8(7) . . . . ?
C9 C8 C13 Se1 -178.3(3) . . . . ?
C9 C8 C13 C12 0.4(7) . . . . ?
C9 C8 C7 N2 -88.9(6) . . . . ?
C9 C10 C11 C12 -0.8(8) . . . . ?
C6 N2 C7 C8 -134.3(5) . . . . ?
C6 C1 C2 C3 -177.8(8) . . . . ?
C14 C19 C18 C17 1.1(12) . . . . ?
C14 C15 C16 C17 0.7(10) . . . . ?
C13 C8 C9 Cl1 -179.5(3) . . . . ?
C13 C8 C9 C10 0.9(7) . . . . ?
C13 C8 C7 N2 91.7(6) . . . . ?
C13 C12 C11 C10 2.0(8) . . . . ?
C1 N1 C5 C4 0.4(11) . . . . ?
C1 C2 C3 C4 -3.1(17) . . . . ?
C7 N2 C6 O1 -6.0(10) . . . . ?
C7 N2 C6 C1 173.6(5) . . . . ?
C7 C8 C9 Cl1 1.0(6) . . . . ?
C7 C8 C9 C10 -178.6(4) . . . . ?
C7 C8 C13 Se1 1.2(6) . . . . ?
C7 C8 C13 C12 179.9(4) . . . . ?
C19 C14 C15 C16 -0.5(9) . . . . ?
C19 C18 C17 C16 -0.8(13) . . . . ?
C15 C14 C19 O2 -177.5(6) . . . . ?
C15 C14 C19 C18 -0.4(10) . . . . ?
C15 C16 C17 C18 -0.1(12) . . . . ?
C5 N1 C1 C6 179.2(6) . . . . ?
C5 N1 C1 C2 0.5(11) . . . . ?
C5 C4 C3 C2 3.8(16) . . . . ?
C20 O2 C19 C14 -163.8(7) . . . . ?
C20 O2 C19 C18 19.3(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.759
_oxdiff_exptl_absorpt_empirical_full_min 0.448
####################################################################### 
# 
# 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_nks-rnb-164a_auto
_database_code_depnum_ccdc_archive 'CCDC 2220554'
loop_
_audit_author_name
_audit_author_address
'Nagendra Sharma'
;School of Chemical Sciences, National Institute of science Education and Research (NISER)Bhubaneswar
India
;
_audit_update_record             
;
2022-11-18 deposited with the CCDC.	2023-01-05 downloaded from the CCDC.
;
_audit_creation_date             2022-07-28
_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         '0.143(C22 H20 N2 O4 S)'
_chemical_formula_sum            'C3.14 H2.86 N0.29 O0.57 S0.14'
_chemical_formula_weight         58.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         ' S C H N O '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.7554(11)
_cell_length_b                   13.0587(7)
_cell_length_c                   10.6435(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.754(7)
_cell_angle_gamma                90
_cell_volume                     1992.0(2)
_cell_formula_units_Z            28
_cell_measurement_reflns_used    7620
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      31.4730
_cell_measurement_theta_min      3.8670
_shelx_estimated_absorpt_T_max   1.000
_shelx_estimated_absorpt_T_min   0.998
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.52a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.001
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.831
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21495
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.491
_diffrn_reflns_theta_min         3.243
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  30.00   0.50   63.21    --    6.51 -78.00 132.00  144
  2  ω    -31.00  21.00   0.50   63.21    --   -7.14  78.00-101.00  104
  3  ω    -42.00   7.00   0.50   63.21    --   -7.14 -78.00 132.00   98
  4  ω    -10.00  33.00   0.50   63.21    --    6.51 -99.00  30.00   86
  5  ω    -44.00  -9.00   0.50   63.21    --   -7.14 -37.00 150.00   70
  6  ω    -41.00  16.00   0.50   63.21    --   -7.14 -77.00-180.00  114
  7  ω    -42.00   5.00   0.50   63.21    --   -7.14 -77.00 -60.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0404224000
_diffrn_orient_matrix_UB_12      -0.0237832000
_diffrn_orient_matrix_UB_13      -0.0121300000
_diffrn_orient_matrix_UB_21      0.0108332000
_diffrn_orient_matrix_UB_22      0.0456446000
_diffrn_orient_matrix_UB_23      -0.0290979000
_diffrn_orient_matrix_UB_31      0.0264667000
_diffrn_orient_matrix_UB_32      0.0173377000
_diffrn_orient_matrix_UB_33      0.0609003000
_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                3461
_reflns_number_total             5507
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_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 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.060
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         5507
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1362
_refine_ls_R_factor_gt           0.0940
_refine_ls_restrained_S_all      1.053
_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)+(0.1069P)²+2.9999P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2407
_refine_ls_wR_factor_ref         0.2628
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C15(H15), C14(H14), C21(H21), C13(H13), C17(H17), C12(H12), C19(H19),
 C18(H18), C2(H2A), C3(H3A), C5(H5), C4(H4)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.88475(8) 0.53838(7) 0.79724(12) 0.0539(3) Uani 1 1 d . . . . .
O4 O 1.03496(18) 0.27105(19) 0.5603(2) 0.0424(6) Uani 1 1 d . . . . .
N2 N 0.5697(2) 0.5321(2) 0.7018(3) 0.0401(7) Uani 1 1 d . . . . .
H2 H 0.547126 0.470065 0.683764 0.048 Uiso 1 1 calc R U . . .
O2 O 0.5161(3) 0.6477(2) 0.4894(3) 0.0696(10) Uani 1 1 d . . . . .
O3 O 0.6622(3) 0.6929(2) 0.4954(3) 0.0779(12) Uani 1 1 d . . . . .
O1 O 0.5682(3) 0.67719(19) 0.8134(3) 0.0699(10) Uani 1 1 d . . . . .
N1 N 0.4238(2) 0.4558(2) 0.7738(3) 0.0456(7) Uani 1 1 d . . . . .
C15 C 0.6841(2) 0.3181(2) 0.7301(3) 0.0326(7) Uani 1 1 d . . . . .
H15 H 0.627188 0.303593 0.669273 0.039 Uiso 1 1 calc R U . . .
C14 C 0.7162(3) 0.2519(2) 0.8322(3) 0.0387(8) Uani 1 1 d . . . . .
H14 H 0.680886 0.192588 0.840977 0.046 Uiso 1 1 calc R U . . .
C21 C 0.9739(2) 0.3950(3) 0.6737(3) 0.0367(7) Uani 1 1 d . . . . .
H21 H 0.924085 0.349061 0.674390 0.044 Uiso 1 1 calc R U . . .
C20 C 1.0446(2) 0.3661(3) 0.6163(3) 0.0362(7) Uani 1 1 d . . . . .
C10 C 0.7344(2) 0.4065(2) 0.7149(3) 0.0338(7) Uani 1 1 d . . . . .
C16 C 0.9751(2) 0.4911(3) 0.7304(3) 0.0379(8) Uani 1 1 d . . . . .
C11 C 0.8178(3) 0.4262(3) 0.8072(4) 0.0399(8) Uani 1 1 d . . . . .
C13 C 0.7993(3) 0.2710(3) 0.9221(4) 0.0460(9) Uani 1 1 d . . . . .
H13 H 0.821474 0.224684 0.991471 0.055 Uiso 1 1 calc R U . . .
C7 C 0.6429(3) 0.5679(2) 0.6452(3) 0.0413(8) Uani 1 1 d . . . . .
H7 H 0.688199 0.607813 0.712231 0.050 Uiso 1 1 calc R U . . .
C1 C 0.4574(3) 0.5464(3) 0.8273(3) 0.0429(9) Uani 1 1 d . . . . .
C9 C 0.6954(3) 0.4776(3) 0.6029(3) 0.0413(8) Uani 1 1 d . . . . .
H9A H 0.652333 0.439048 0.533431 0.050 Uiso 1 1 calc R U . . .
H9B H 0.747046 0.504125 0.567414 0.050 Uiso 1 1 calc R U . . .
C17 C 1.0490(3) 0.5576(3) 0.7319(4) 0.0464(9) Uani 1 1 d . . . . .
H17 H 1.050876 0.623162 0.771087 0.056 Uiso 1 1 calc R U . . .
C6 C 0.5355(3) 0.5909(2) 0.7806(3) 0.0458(9) Uani 1 1 d . . . . .
C12 C 0.8500(3) 0.3592(3) 0.9094(4) 0.0447(9) Uani 1 1 d . . . . .
H12 H 0.906728 0.373370 0.970883 0.054 Uiso 1 1 calc R U . . .
C19 C 1.1187(3) 0.4308(3) 0.6171(4) 0.0478(9) Uani 1 1 d . . . . .
H19 H 1.167834 0.410662 0.578732 0.057 Uiso 1 1 calc R U . . .
C18 C 1.1197(3) 0.5266(3) 0.6756(4) 0.0555(11) Uani 1 1 d . . . . .
H18 H 1.170355 0.571750 0.676627 0.067 Uiso 1 1 calc R U . . .
C8 C 0.5996(4) 0.6404(3) 0.5345(4) 0.0624(14) Uani 1 1 d . . . . .
C2 C 0.4233(3) 0.5947(3) 0.9232(4) 0.0552(12) Uani 1 1 d . . . . .
H2A H 0.448399 0.658271 0.958652 0.066 Uiso 1 1 calc R U . . .
C22 C 1.1005(3) 0.2421(3) 0.4879(4) 0.0537(10) Uani 1 1 d . . . . .
H22A H 1.104728 0.296256 0.425818 0.080 Uiso 1 1 calc R U . . .
H22B H 1.080158 0.178271 0.441337 0.080 Uiso 1 1 calc R U . . .
H22C H 1.161884 0.231862 0.546843 0.080 Uiso 1 1 calc R U . . .
C3 C 0.3521(4) 0.5476(4) 0.9654(4) 0.0620(13) Uani 1 1 d . . . . .
H3A H 0.327152 0.578595 1.030604 0.074 Uiso 1 1 calc R U . . .
C5 C 0.3555(3) 0.4120(4) 0.8160(4) 0.0566(10) Uani 1 1 d . . . . .
H5 H 0.331349 0.348346 0.779356 0.068 Uiso 1 1 calc R U . . .
C4 C 0.3175(3) 0.4555(4) 0.9121(4) 0.0608(12) Uani 1 1 d . . . . .
H4 H 0.268651 0.421974 0.940091 0.073 Uiso 1 1 calc R U . . .
H3 H 0.627(4) 0.746(5) 0.423(5) 0.090(18) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C16 1.766(4) . ?
S1 C11 1.784(4) . ?
O4 C20 1.369(4) . ?
O4 C22 1.424(5) . ?
N2 H2 0.8800 . ?
N2 C7 1.435(5) . ?
N2 C6 1.321(5) . ?
O2 C8 1.215(6) . ?
O3 C8 1.296(6) . ?
O3 H3 1.08(6) . ?
O1 C6 1.243(4) . ?
N1 C1 1.355(5) . ?
N1 C5 1.327(6) . ?
C15 H15 0.9500 . ?
C15 C14 1.382(4) . ?
C15 C10 1.401(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.387(5) . ?
C21 H21 0.9500 . ?
C21 C20 1.381(5) . ?
C21 C16 1.390(5) . ?
C20 C19 1.381(5) . ?
C10 C11 1.404(5) . ?
C10 C9 1.514(5) . ?
C16 C17 1.391(5) . ?
C11 C12 1.389(5) . ?
C13 H13 0.9500 . ?
C13 C12 1.398(6) . ?
C7 H7 1.0000 . ?
C7 C9 1.535(5) . ?
C7 C8 1.529(5) . ?
C1 C6 1.479(6) . ?
C1 C2 1.390(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C17 H17 0.9500 . ?
C17 C18 1.381(6) . ?
C12 H12 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.396(6) . ?
C18 H18 0.9500 . ?
C2 H2A 0.9500 . ?
C2 C3 1.382(7) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C3 H3A 0.9500 . ?
C3 C4 1.375(7) . ?
C5 H5 0.9500 . ?
C5 C4 1.398(6) . ?
C4 H4 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
C16 S1 C11 102.64(16) . . ?
C20 O4 C22 117.6(3) . . ?
C7 N2 H2 119.4 . . ?
C6 N2 H2 119.4 . . ?
C6 N2 C7 121.1(3) . . ?
C8 O3 H3 108(3) . . ?
C5 N1 C1 117.8(3) . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C10 121.0(3) . . ?
C10 C15 H15 119.5 . . ?
C15 C14 H14 119.6 . . ?
C15 C14 C13 120.7(3) . . ?
C13 C14 H14 119.6 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C16 120.4(3) . . ?
C16 C21 H21 119.8 . . ?
O4 C20 C21 115.4(3) . . ?
O4 C20 C19 123.9(3) . . ?
C19 C20 C21 120.7(4) . . ?
C15 C10 C11 118.1(3) . . ?
C15 C10 C9 118.9(3) . . ?
C11 C10 C9 123.0(3) . . ?
C21 C16 S1 123.9(3) . . ?
C21 C16 C17 119.9(4) . . ?
C17 C16 S1 116.2(3) . . ?
C10 C11 S1 121.0(3) . . ?
C12 C11 S1 118.2(3) . . ?
C12 C11 C10 120.8(3) . . ?
C14 C13 H13 120.4 . . ?
C14 C13 C12 119.2(3) . . ?
C12 C13 H13 120.4 . . ?
N2 C7 H7 108.2 . . ?
N2 C7 C9 110.9(3) . . ?
N2 C7 C8 107.8(4) . . ?
C9 C7 H7 108.2 . . ?
C8 C7 H7 108.2 . . ?
C8 C7 C9 113.4(3) . . ?
N1 C1 C6 116.0(3) . . ?
N1 C1 C2 123.0(4) . . ?
C2 C1 C6 121.0(4) . . ?
C10 C9 C7 111.3(3) . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C7 C9 H9A 109.4 . . ?
C7 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C16 C17 H17 120.6 . . ?
C18 C17 C16 118.9(4) . . ?
C18 C17 H17 120.6 . . ?
N2 C6 C1 115.5(3) . . ?
O1 C6 N2 121.6(4) . . ?
O1 C6 C1 122.9(4) . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C20 C19 H19 120.8 . . ?
C20 C19 C18 118.4(4) . . ?
C18 C19 H19 120.8 . . ?
C17 C18 C19 121.8(4) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
O2 C8 O3 124.4(4) . . ?
O2 C8 C7 123.5(4) . . ?
O3 C8 C7 112.1(4) . . ?
C1 C2 H2A 120.9 . . ?
C3 C2 C1 118.2(4) . . ?
C3 C2 H2A 120.9 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 C2 119.4(4) . . ?
C4 C3 H3A 120.3 . . ?
N1 C5 H5 118.7 . . ?
N1 C5 C4 122.7(4) . . ?
C4 C5 H5 118.7 . . ?
C3 C4 C5 118.9(5) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?

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 -177.0(3) . . . . ?
S1 C11 C12 C13 179.2(3) . . . . ?
O4 C20 C19 C18 179.0(3) . . . . ?
N2 C7 C9 C10 -56.8(4) . . . . ?
N2 C7 C8 O2 -13.3(5) . . . . ?
N2 C7 C8 O3 166.4(3) . . . . ?
N1 C1 C6 N2 -6.6(5) . . . . ?
N1 C1 C6 O1 174.1(3) . . . . ?
N1 C1 C2 C3 0.1(5) . . . . ?
N1 C5 C4 C3 0.1(7) . . . . ?
C15 C14 C13 C12 0.9(5) . . . . ?
C15 C10 C11 S1 -178.6(2) . . . . ?
C15 C10 C11 C12 0.9(5) . . . . ?
C15 C10 C9 C7 97.4(4) . . . . ?
C14 C15 C10 C11 -0.6(5) . . . . ?
C14 C15 C10 C9 -178.8(3) . . . . ?
C14 C13 C12 C11 -0.6(6) . . . . ?
C21 C20 C19 C18 -0.9(5) . . . . ?
C21 C16 C17 C18 0.5(5) . . . . ?
C20 C21 C16 S1 175.9(2) . . . . ?
C20 C21 C16 C17 -1.4(5) . . . . ?
C20 C19 C18 C17 0.0(6) . . . . ?
C10 C15 C14 C13 -0.3(5) . . . . ?
C10 C11 C12 C13 -0.3(5) . . . . ?
C16 S1 C11 C10 -101.1(3) . . . . ?
C16 S1 C11 C12 79.3(3) . . . . ?
C16 C21 C20 O4 -178.2(3) . . . . ?
C16 C21 C20 C19 1.6(5) . . . . ?
C16 C17 C18 C19 0.2(6) . . . . ?
C11 S1 C16 C21 13.7(3) . . . . ?
C11 S1 C16 C17 -168.9(3) . . . . ?
C11 C10 C9 C7 -80.8(4) . . . . ?
C7 N2 C6 O1 -3.4(5) . . . . ?
C7 N2 C6 C1 177.3(3) . . . . ?
C1 N1 C5 C4 0.1(6) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C9 C10 C11 S1 -0.4(5) . . . . ?
C9 C10 C11 C12 179.1(3) . . . . ?
C9 C7 C8 O2 109.9(5) . . . . ?
C9 C7 C8 O3 -70.4(4) . . . . ?
C6 N2 C7 C9 158.2(3) . . . . ?
C6 N2 C7 C8 -77.1(4) . . . . ?
C6 C1 C2 C3 -178.1(3) . . . . ?
C8 C7 C9 C10 -178.3(3) . . . . ?
C2 C1 C6 N2 171.7(3) . . . . ?
C2 C1 C6 O1 -7.6(5) . . . . ?
C2 C3 C4 C5 -0.2(6) . . . . ?
C22 O4 C20 C21 173.4(3) . . . . ?
C22 O4 C20 C19 -6.5(5) . . . . ?
C5 N1 C1 C6 178.0(3) . . . . ?
C5 N1 C1 C2 -0.2(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 1.558
_oxdiff_exptl_absorpt_empirical_full_min 0.636
