# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_vjk2031
_database_code_depnum_ccdc_archive 'CCDC 2109616'
loop_
_audit_author_name
_audit_author_address
'Stephen A. Moggach'
;University of Western Australia
Australia
;
_audit_update_record             
;
2021-09-14 deposited with the CCDC.	2021-12-16 downloaded from the CCDC.
;
_audit_creation_date             2021-08-29
_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         'C15 H13 Cl N2 O'
_chemical_formula_sum            'C15 H13 Cl N2 O'
_chemical_formula_weight         272.72
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N2 O1 Cl1 C15 H12'
_chemical_oxdiff_usercomment     'Varshini for Low'
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'
Cl Cl 0.3639 0.7018 '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/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                   8.9460(2)
_cell_length_b                   11.1772(3)
_cell_length_c                   13.8578(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.517(2)
_cell_angle_gamma                90
_cell_volume                     1362.38(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10272
_cell_measurement_temperature    99.8(7)
_cell_measurement_theta_max      74.4180
_cell_measurement_theta_min      5.0050
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.421
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66107
_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            'clear light colourless'
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -7 -3 0.0212
6 0 -1 0.0114
2 5 5 0.0085
-6 0 1 0.0190
-4 -1 -5 0.0202
0 0 -9 0.0134
-1 -3 8 0.0133
-1 -5 7 0.0133
2 6 -5 0.0162
0 -7 -3 0.0209
0 -4 -8 0.0171
1 0 -9 0.0134
3 4 -7 0.0145
-2 -6 5 0.0175

_exptl_crystal_size_max          0.051
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.028
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.8665 -6.6463 -3.0483 -0.1802 -0.9688 -0.1700
5.7758 -0.0614 -0.7119 -0.0004 0.0091 1.0000
2.2787 5.0033 4.7426 -0.1165 0.8909 0.4391
-5.7744 0.0755 0.6933 0.0032 -0.0085 -1.0000
-3.9613 -1.1532 -5.1955 0.4573 -0.4832 -0.7466
-0.1919 0.4115 -8.7713 0.8708 -0.4735 -0.1325
-0.6225 -2.6177 8.3696 -0.9831 0.1827 -0.0090
-0.5583 -4.5797 6.9637 -0.9915 -0.1300 -0.0090
2.4437 5.6463 -4.8146 0.8423 0.4016 0.3596
0.0652 -6.7628 -3.2183 -0.1827 -0.9831 -0.0090
0.3779 -3.9317 -7.5178 0.4301 -0.9028 -0.0090
1.3389 0.3807 -8.9719 0.8708 -0.4735 0.1325
2.6950 4.1801 -6.7130 0.9149 0.1197 0.3856
-1.5862 -5.9363 4.9224 -0.8831 -0.4205 -0.2081

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24984
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.992
_diffrn_reflns_theta_min         5.028
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.8(7)
_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 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00 -30.00   0.50   12.00    -- -102.41  61.00  30.00   82
  2  ω    -26.00  29.00   0.50    1.60    --  -46.20  19.00 -60.00  110
  3  ω     69.00 118.00   0.50    1.60    --   46.20 132.00  93.00   98
  4  ω     98.00 123.00   0.50   12.00    --  102.41 132.00  93.00   50
  5  ω    151.00 177.00   0.50   12.00    --  102.41  30.00  30.00   52
  6  ω     90.00 174.00   0.50   12.00    --  102.41  45.00-150.00  168
  7  ω     91.00 130.00   0.50   12.00    --  102.41  30.00  30.00   78
  8  ω     66.00 118.00   0.50    1.60    --   46.20 137.00 -90.00  104
  9  ω     24.00 118.00   0.50    1.60    --   46.20  77.00 -60.00  188
 10  ω     30.00  71.00   0.50   12.00    --  102.41 -61.00 -90.00   82
 11  ω     17.00  98.00   0.50    1.60    --   46.20-132.00  23.00  162
 12  ω     74.00 105.00   0.50   12.00    --  102.41 -94.00  30.00   62
 13  ω     80.00 110.00   0.50   12.00    --  102.41-125.00  60.00   60
 14  ω     40.00  66.00   0.50   12.00    --  102.41 -61.00 150.00   52
 15  ω     30.00 105.00   0.50   12.00    --  102.41 -77.00 120.00  150
 16  ω     30.00 117.00   0.50   12.00    --  102.41-132.00  23.00  174
 17  ω     30.00 121.00   0.50   12.00    --  102.41-137.00-153.00  182
 18  ω     33.00  70.00   0.50   12.00    --  102.41 -94.00  30.00   74
 19  ω     20.00 101.00   0.50    1.60    --   46.20-137.00-153.00  162
 20  ω    -28.00  26.00   0.50    1.60    --   46.20 -19.00   0.00  108
 21  ω   -101.00 -19.00   0.50    1.60    --  -46.20 137.00 -90.00  164
 22  ω    -98.00 -17.00   0.50    1.60    --  -46.20 132.00  93.00  162
 23  ω    -71.00 -30.00   0.50   12.00    -- -102.41  61.00 150.00   82
 24  ω   -105.00 -30.00   0.50   12.00    -- -102.41  77.00 120.00  150
 25  ω   -117.00 -30.00   0.50   12.00    -- -102.41 132.00  93.00  174
 26  ω   -105.00 -30.00   0.50   12.00    -- -102.41  77.00 -60.00  150
 27  ω   -111.00 -30.00   0.50   12.00    -- -102.41 125.00-180.00  162
 28  ω   -111.00 -30.00   0.50   12.00    -- -102.41 125.00-120.00  162
 29  ω   -121.00 -30.00   0.50   12.00    -- -102.41 137.00 -90.00  182
 30  ω   -119.00 -34.00   0.50    1.60    --  -46.20 -38.00 -30.00  170
 31  ω   -118.00 -66.00   0.50    1.60    --  -46.20-137.00-153.00  104
 32  ω   -118.00 -73.00   0.50    1.60    --  -46.20-125.00-120.00   90
 33  ω   -118.00 -69.00   0.50    1.60    --  -46.20-132.00  23.00   98
 34  ω   -118.00 -73.00   0.50    1.60    --  -46.20-125.00  60.00   90
 35  ω   -175.00 -69.00   0.50   12.00    -- -102.41-132.00  23.00  212
 36  ω   -175.00 -66.00   0.50   12.00    -- -102.41-137.00-153.00  218
 37  ω   -175.00 -80.00   0.50   12.00    -- -102.41 -77.00 -60.00  190
 38  ω   -175.00 -80.00   0.50   12.00    -- -102.41 -77.00 120.00  190
 39  ω   -177.00 -90.00   0.50   12.00    -- -102.41 -30.00  30.00  174
 40  ω   -175.00 -80.00   0.50   12.00    -- -102.41 -77.00-150.00  190
 41  ω   -177.00 -89.00   0.50   12.00    -- -102.41 -15.00-150.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0110818000
_diffrn_orient_matrix_UB_12      0.0724216000
_diffrn_orient_matrix_UB_13      -0.0956376000
_diffrn_orient_matrix_UB_21      0.0101227000
_diffrn_orient_matrix_UB_22      0.1172700000
_diffrn_orient_matrix_UB_23      0.0592607000
_diffrn_orient_matrix_UB_31      0.1744823000
_diffrn_orient_matrix_UB_32      -0.0022995000
_diffrn_orient_matrix_UB_33      0.0111777000
_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                2521
_reflns_number_total             2755
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2755
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.063
_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)+(0.0372P)²+0.8589P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0967
_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:
 C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Cl1 Cl 0.63809(5) 0.66195(4) 0.51790(3) 0.02664(14) Uani 1 1 d . . . . .
O1 O 0.41193(14) 0.71664(12) 0.60269(9) 0.0296(3) Uani 1 1 d . . . . .
N1 N 0.54944(15) 0.55478(12) 0.66736(10) 0.0194(3) Uani 1 1 d . . . . .
N2 N 0.66968(15) 0.48021(12) 0.65675(10) 0.0199(3) Uani 1 1 d . . . . .
C1 C 0.51441(19) 0.64739(15) 0.60403(12) 0.0217(3) Uani 1 1 d . . . . .
C2 C 0.70750(18) 0.39667(15) 0.71921(12) 0.0200(3) Uani 1 1 d . . . . .
H2 H 0.655270 0.385445 0.770698 0.024 Uiso 1 1 calc R . . . .
C3 C 0.83541(18) 0.31856(15) 0.70801(12) 0.0207(3) Uani 1 1 d . . . . .
C4 C 0.90266(19) 0.32502(16) 0.62411(13) 0.0242(4) Uani 1 1 d . . . . .
H4 H 0.867511 0.380230 0.574992 0.029 Uiso 1 1 calc R . . . .
C5 C 1.02123(19) 0.24912(16) 0.61475(14) 0.0268(4) Uani 1 1 d . . . . .
H5 H 1.065948 0.253506 0.559313 0.032 Uiso 1 1 calc R . . . .
C6 C 1.07377(19) 0.16636(16) 0.68782(14) 0.0267(4) Uani 1 1 d . . . . .
H6 H 1.153334 0.115383 0.680967 0.032 Uiso 1 1 calc R . . . .
C7 C 1.00856(19) 0.15932(16) 0.77059(14) 0.0259(4) Uani 1 1 d . . . . .
H7 H 1.044276 0.103877 0.819409 0.031 Uiso 1 1 calc R . . . .
C8 C 0.88916(18) 0.23544(15) 0.78082(13) 0.0227(3) Uani 1 1 d . . . . .
H8 H 0.845201 0.230683 0.836558 0.027 Uiso 1 1 calc R . . . .
C9 C 0.45948(17) 0.53846(15) 0.74332(11) 0.0178(3) Uani 1 1 d . . . . .
C10 C 0.34809(19) 0.45120(15) 0.73245(12) 0.0229(4) Uani 1 1 d . . . . .
H10 H 0.329400 0.404248 0.676134 0.028 Uiso 1 1 calc R . . . .
C11 C 0.26433(19) 0.43437(15) 0.80656(12) 0.0232(4) Uani 1 1 d . . . . .
H11 H 0.189353 0.375744 0.799533 0.028 Uiso 1 1 calc R . . . .
C12 C 0.29125(18) 0.50419(15) 0.89119(12) 0.0200(3) Uani 1 1 d . . . . .
C13 C 0.40314(18) 0.59190(15) 0.90048(12) 0.0211(3) Uani 1 1 d . . . . .
H13 H 0.421682 0.639399 0.956490 0.025 Uiso 1 1 calc R . . . .
C14 C 0.48774(18) 0.60928(15) 0.82660(12) 0.0202(3) Uani 1 1 d . . . . .
H14 H 0.562584 0.667992 0.833195 0.024 Uiso 1 1 calc R . . . .
C15 C 0.2009(2) 0.48486(17) 0.97138(13) 0.0268(4) Uani 1 1 d . . . . .
H15A H 0.246235 0.421634 1.013739 0.040 Uiso 1 1 calc GR . . . .
H15B H 0.098415 0.463456 0.942873 0.040 Uiso 1 1 calc GR . . . .
H15C H 0.200367 0.557166 1.008713 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
Cl1 C1 1.7770(16) . ?
O1 C1 1.197(2) . ?
N1 N2 1.3897(18) . ?
N1 C1 1.356(2) . ?
N1 C9 1.4485(18) . ?
N2 C2 1.276(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.470(2) . ?
C3 C4 1.405(2) . ?
C3 C8 1.391(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.393(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.383(2) . ?
C9 C14 1.384(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.390(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.393(2) . ?
C12 C13 1.390(2) . ?
C12 C15 1.504(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.393(2) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
N2 N1 C9 123.01(13) . . ?
C1 N1 N2 118.77(13) . . ?
C1 N1 C9 118.23(13) . . ?
C2 N2 N1 118.80(13) . . ?
O1 C1 Cl1 119.95(13) . . ?
O1 C1 N1 126.10(15) . . ?
N1 C1 Cl1 113.95(12) . . ?
N2 C2 H2 120.7 . . ?
N2 C2 C3 118.56(14) . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 121.07(15) . . ?
C8 C3 C2 119.52(14) . . ?
C8 C3 C4 119.40(15) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.85(16) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.25(16) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.37(16) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.86(17) . . ?
C8 C7 H7 120.1 . . ?
C3 C8 C7 120.27(15) . . ?
C3 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 N1 119.64(14) . . ?
C10 C9 C14 120.83(14) . . ?
C14 C9 N1 119.52(14) . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.33(15) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.84(15) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C15 120.53(15) . . ?
C13 C12 C11 118.95(14) . . ?
C13 C12 C15 120.52(15) . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.59(15) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 C13 119.46(15) . . ?
C9 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
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 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C2 C3 -179.60(14) . . . . ?
N1 C9 C10 C11 178.68(15) . . . . ?
N1 C9 C14 C13 -178.75(14) . . . . ?
N2 N1 C1 Cl1 -2.6(2) . . . . ?
N2 N1 C1 O1 177.90(17) . . . . ?
N2 N1 C9 C10 -78.3(2) . . . . ?
N2 N1 C9 C14 100.72(18) . . . . ?
N2 C2 C3 C4 -8.0(2) . . . . ?
N2 C2 C3 C8 173.09(15) . . . . ?
C1 N1 N2 C2 176.58(15) . . . . ?
C1 N1 C9 C10 101.84(19) . . . . ?
C1 N1 C9 C14 -79.1(2) . . . . ?
C2 C3 C4 C5 -178.94(16) . . . . ?
C2 C3 C8 C7 178.89(15) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C3 C8 C7 0.0(2) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 C3 0.0(3) . . . . ?
C8 C3 C4 C5 -0.1(3) . . . . ?
C9 N1 N2 C2 -3.3(2) . . . . ?
C9 N1 C1 Cl1 177.30(11) . . . . ?
C9 N1 C1 O1 -2.2(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C9 C14 C13 0.3(2) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C10 C11 C12 C15 -179.57(16) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?
C12 C13 C14 C9 0.1(2) . . . . ?
C14 C9 C10 C11 -0.3(3) . . . . ?
C15 C12 C13 C14 179.50(15) . . . . ?

_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
;

####################################################################### 
# 
# 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_vjk2023
_database_code_depnum_ccdc_archive 'CCDC 2109618'
loop_
_audit_author_name
_audit_author_address
'Stephen A. Moggach'
;University of Western Australia
Australia
;
_audit_update_record             
;
2021-09-14 deposited with the CCDC.	2021-12-16 downloaded from the CCDC.
;
_audit_creation_date             2021-08-29
_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         'C22 H22 N4 O S2, 2(C H Cl3)'
_chemical_formula_sum            'C24 H24 Cl6 N4 O S2'
_chemical_formula_weight         661.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N4 O1 S2 C20 H20'
_chemical_oxdiff_usercomment     'Varshini for Low'
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'
Cl Cl 0.3639 0.7018 '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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   24.2469(4)
_cell_length_b                   5.37710(10)
_cell_length_c                   44.3688(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.275(2)
_cell_angle_gamma                90
_cell_volume                     5760.2(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    26120
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      73.9820
_cell_measurement_theta_min      3.6510
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.020
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61959
_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            'clear light colourless'
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2704
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-13 0 -12 0.0324
15 0 4 0.0269
15 0 -13 0.0295
-15 0 -4 0.0291
12 1 -21 0.0342
-12 -1 21 0.0361
3 -3 -1 0.1349
8 0 -26 0.0285
2 0 28 0.0305
-6 0 -25 0.0305
11 0 19 0.0309
-11 1 -19 0.0397
16 0 -5 0.0253
-15 1 5 0.0399
-16 0 5 0.0291
-4 1 28 0.0433
-15 0 -4 0.0343
-14 1 13 0.0425
-15 0 13 0.0319
7 0 25 0.0369
12 0 -21 0.0291
-1 0 -28 0.0305
-3 3 1 0.1368
6 0 25 0.0304

_exptl_crystal_size_max          0.286
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.056
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-13.4080 -0.3843 -12.4193 0.4764 0.8766 0.0677
15.3330 0.1851 3.7179 -0.1805 -0.9720 -0.1504
14.5308 -0.1951 -13.3766 0.4163 -0.8745 -0.2489
-15.3649 0.0083 -3.6396 0.1787 0.9623 0.2050
11.6225 0.5279 -20.8064 0.6880 -0.7257 -0.0090
-11.6225 -0.5279 20.8064 -0.6880 0.7257 0.0090
3.4253 -3.4072 -0.6547 -0.0025 -0.0087 -1.0000
7.9255 0.3562 -25.9373 0.8785 -0.4776 -0.0090
1.5524 -0.1327 28.2471 -0.9901 -0.1298 -0.0533
-6.2162 -0.0891 -25.2797 0.9015 0.4294 0.0533
10.5469 -0.1389 19.4688 -0.7146 -0.6772 -0.1754
-10.6417 0.5027 -18.9171 0.6971 0.6606 0.2787
15.6817 -0.0279 -5.1594 0.1268 -0.9681 -0.2160
-15.2981 0.7738 4.9469 -0.1177 0.8999 0.4199
-15.6778 -0.0747 5.1700 -0.1276 0.9740 0.1872
-4.1540 0.6966 27.7669 -0.9508 0.1769 0.2544
-15.1894 -0.4848 -3.8171 0.1823 0.9811 0.0645
-14.1658 0.8917 12.5527 -0.3861 0.8113 0.4391
-14.5039 0.3418 13.2495 -0.4114 0.8642 0.2896
6.5779 -0.4068 24.7172 -0.8851 -0.4215 -0.1971
12.0063 -0.0902 -20.5633 0.6757 -0.7130 -0.1872
-1.2011 -0.2315 -28.3232 0.9901 0.1298 -0.0534
-3.2922 3.4133 0.9731 -0.0091 -0.0004 1.0000
6.0794 0.2407 25.3456 -0.9028 -0.4301 -0.0090

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1425
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_number            99682
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.695
_diffrn_reflns_theta_min         3.661
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(6)
_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 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -99.00 -19.00   0.50    2.00    --  -46.20 134.00  35.00  160
  2  ω    -32.00  -7.00   0.50    2.00    --   10.00 115.00 136.06   50
  3  ω      8.00  33.00   0.50    2.00    --   38.00  93.00 146.86   50
  4  ω     28.00  54.00   0.50    2.00    --   50.00  80.00 150.43   52
  5  ω     40.00  70.00   0.50    2.00    --   62.00  80.00 175.40   60
  6  ω     97.00 122.00   0.50    2.00    --   50.00  80.00 150.43   50
  7  ω    100.00 138.00   0.50    2.00    --   66.00  79.00 119.98   76
  8  ω     72.00  97.00   0.50    2.00    --   46.20 134.00  35.00   50
  9  ω     77.00 118.00   0.50    2.00    --   46.00  80.00 -52.46   82
 10  ω     74.00 118.00   0.50    2.00    --   46.20 135.00-144.00   88
 11  ω     97.00 122.00   0.50    6.00    --  102.41 135.00-144.00   50
 12  ω     56.00  82.00   0.50    2.00    --   46.00  79.00 -99.53   52
 13  ω     51.00  77.00   0.50    2.00    --   74.00  77.00-102.39   52
 14  ω     34.00  60.00   0.50    2.00    --   58.00  80.00-121.06   52
 15  ω     35.00  87.00   0.50    2.00    --   58.00  79.00 -88.44  104
 16  ω     48.00  74.00   0.50    2.00    --   70.00  78.00 -33.89   52
 17  ω     44.00  71.00   0.50    2.00    --   66.00  78.00  22.26   54
 18  ω     42.00 134.00   0.50    2.00    --   62.00  74.00  84.39  184
 19  ω     71.00 170.00   0.50    6.00    --  102.41 134.00  35.00  198
 20  ω     38.00  64.00   0.50    2.00    --   62.00  79.00-135.29   52
 21  ω     24.00  55.00   0.50    2.00    --   46.00  79.00 -99.53   62
 22  ω     26.00  55.00   0.50    2.00    --   50.00  80.00-147.74   58
 23  ω      7.00  32.00   0.50    2.00    --   38.00  94.00-144.49   50
 24  ω     -6.00  26.00   0.50    2.00    --   26.00  98.00 -35.64   64
 25  ω     22.00  50.00   0.50    2.00    --   46.00  80.00 -52.46   56
 26  ω     31.00  60.00   0.50    2.00    --   54.00  78.00 -40.58   58
 27  ω     35.00  61.00   0.50    2.00    --   58.00  78.00  -7.56   52
 28  ω     47.00  73.00   0.50    2.00    --   70.00  78.00  29.31   52
 29  ω     47.00  87.00   0.50    2.00    --   70.00  77.00  88.76   80
 30  ω     43.00  75.00   0.50    2.00    --   66.00  78.00 152.88   64
 31  ω     47.00  77.00   0.50    2.00    --   70.00  77.00 131.96   60
 32  ω     34.00  65.00   0.50    2.00    --   58.00  80.00 101.10   62
 33  ω     42.00  95.00   0.50    2.00    --   66.00  79.00 119.98  106
 34  ω     38.00  64.00   0.50    2.00    --   62.00  80.00  11.92   52
 35  ω     32.00  73.00   0.50    2.00    --   50.00  78.00  26.58   82
 36  ω     30.00 101.00   0.50    2.00    --   50.00  79.00 102.46  142
 37  ω     31.00  69.00   0.50    2.00    --   54.00  79.00  68.02   76
 38  ω     17.00  42.00   0.50    2.00    --   46.00  90.00 -13.48   50
 39  ω     17.00  42.00   0.50    2.00    --   46.00  90.00  16.17   50
 40  ω    -15.00  17.00   0.50    2.00    --   18.00  99.00  51.80   64
 41  ω     31.00  57.00   0.50    2.00    --   54.00  79.00 174.68   52
 42  ω     31.00  58.00   0.50    6.00    --  102.41 -61.00 -30.00   54
 43  ω     34.00  60.00   0.50    2.00    --   46.20-134.00 -31.00   52
 44  ω     50.00  75.00   0.50    6.00    --  102.41-134.00 -31.00   50
 45  ω     55.00 108.00   0.50    6.00    --  102.41-125.00   0.00  106
 46  ω     57.00  83.00   0.50    2.00    --   46.20-135.00 149.00   52
 47  ω     79.00 112.00   0.50    6.00    --  102.41-135.00 149.00   66
 48  ω     30.00 105.00   0.50    6.00    --  102.41 -77.00  60.00  150
 49  ω     40.00 104.00   0.50    6.00    --  102.41 -94.00 150.00  128
 50  ω     31.00 105.00   0.50    6.00    --  102.41 -94.00-150.00  148
 51  ω    -48.00 -17.00   0.50    2.00    --    2.00 130.00-147.74   62
 52  ω    -99.00 -43.00   0.50    2.00    --  -46.20 135.00-144.00  112
 53  ω    -66.00 -40.00   0.50    6.00    -- -102.41 112.00-167.46   52
 54  ω    -69.00 -31.00   0.50    6.00    -- -102.41  61.00 -90.00   76
 55  ω   -100.00 -38.00   0.50    6.00    -- -102.41 125.00   0.00  124
 56  ω    -69.00 -31.00   0.50    6.00    -- -102.41  77.00  60.00   76
 57  ω    -70.00 -31.00   0.50    6.00    -- -102.41  61.00 150.00   78
 58  ω    -66.00 -41.00   0.50    6.00    -- -102.41 110.00 150.19   50
 59  ω   -108.00 -81.00   0.50    6.00    -- -102.41 110.00 150.19   54
 60  ω   -117.00 -64.00   0.50    6.00    -- -102.41 134.00  35.00  106
 61  ω   -107.00 -30.00   0.50    6.00    -- -102.41 109.00 -11.10  154
 62  ω   -106.00 -73.00   0.50    6.00    -- -102.41 135.00-144.00   66
 63  ω   -108.00 -79.00   0.50    6.00    -- -102.41 112.00-167.46   58
 64  ω   -117.00 -61.00   0.50    6.00    -- -102.41 132.00 -79.67  112
 65  ω    -93.00 -61.00   0.50    6.00    --  -82.00 -72.00  20.17   64
 66  ω    -80.00 -43.00   0.50    2.00    --  -66.00 -77.00  23.33   74
 67  ω    -84.00 -56.00   0.50    6.00    --  -78.00 -75.00  44.05   56
 68  ω    -80.00 -54.00   0.50    6.00    --  -78.00 -80.00 -11.02   52
 69  ω    -85.00 -41.00   0.50    2.00    --  -62.00 -75.00 -71.86   88
 70  ω    -71.00 -45.00   0.50    2.00    --  -66.00 -74.00-149.33   52
 71  ω    -79.00 -47.00   0.50    2.00    --  -70.00 -78.00-173.53   64
 72  ω    -81.00 -54.00   0.50    2.00    --  -74.00 -73.00-177.50   54
 73  ω    -97.00 -61.00   0.50    6.00    --  -82.00 -72.00 -89.88   72
 74  ω    -82.00 -56.00   0.50    6.00    --  -78.00 -74.00 -72.95   52
 75  ω    -85.00 -59.00   0.50    6.00    --  -82.00 -80.00 -21.10   52
 76  ω    -86.00 -60.00   0.50    6.00    --  -82.00 -74.00 -60.21   52
 77  ω    -87.00 -61.00   0.50    6.00    --  -82.00 -72.00 -77.10   52
 78  ω    -86.00 -60.00   0.50    6.00    --  -82.00 -75.00 -44.64   52
 79  ω    -99.00 -73.00   0.50    2.00    --  -46.20-134.00 -31.00   52
 80  ω    -97.00 -59.00   0.50    6.00    --  -82.00 -77.00-100.21   76
 81  ω    -92.00 -58.00   0.50    6.00    --  -82.00 -79.00-123.94   68
 82  ω    -91.00 -66.00   0.50    6.00    --  -86.00 -71.00-167.19   50
 83  ω   -104.00 -73.00   0.50    6.00    --  -90.00 -66.00-112.37   62
 84  ω   -112.00 -71.00   0.50    6.00    --  -94.00 -76.00-164.27   82
 85  ω   -119.00 -93.00   0.50    6.00    --  -86.00 -71.00-167.19   52
 86  ω   -131.00-105.00   0.50    6.00    --  -90.00 -66.00-112.37   52
 87  ω   -129.00 -92.00   0.50    6.00    -- -102.41-134.00 -31.00   74
 88  ω    -90.00 -63.00   0.50    6.00    --  -86.00 -76.00  52.21   54
 89  ω    -94.00 -65.00   0.50    6.00    --  -86.00 -72.00  13.39   58
 90  ω    -95.00 -69.00   0.50    6.00    --  -90.00 -73.00  72.69   52
 91  ω    -86.00 -60.00   0.50    6.00    --  -82.00 -75.00 127.49   52
 92  ω    -80.00 -54.00   0.50    6.00    --  -78.00 -80.00 174.40   52
 93  ω    -93.00 -67.00   0.50    2.00    --  -46.20-135.00 149.00   52
 94  ω    -93.00 -68.00   0.50    6.00    --  -90.00 -74.00  95.19   50
 95  ω    -99.00 -62.00   0.50    6.00    --  -82.00 -71.00 150.40   74
 96  ω    -93.00 -68.00   0.50    6.00    --  -90.00 -74.00 154.91   50
 97  ω    -99.00 -66.00   0.50    6.00    --  -86.00 -71.00  96.81   66
 98  ω    -96.00 -71.00   0.50    6.00    --  -94.00 -78.00  51.41   50
 99  ω   -100.00 -65.00   0.50    6.00    --  -86.00 -73.00 -11.20   70
100  ω    -99.00 -69.00   0.50    6.00    --  -90.00 -73.00 -15.13   60
101  ω   -100.00 -75.00   0.50    6.00    --  -94.00 -68.00  11.58   50
102  ω   -109.00 -67.00   0.50    6.00    --  -90.00 -79.00 130.30   84
103  ω   -108.00 -76.00   0.50    6.00    --  -94.00 -66.00 163.82   64
104  ω   -120.00 -79.00   0.50    6.00    -- -102.41 -79.00 171.64   82
105  ω   -127.00 -68.00   0.50    6.00    --  -90.00 -75.00 138.83  118
106  ω   -147.00-121.00   0.50    6.00    --  -86.00 -76.00  52.21   52
107  ω   -152.00 -68.00   0.50    6.00    --  -90.00 -74.00  84.54  168
108  ω   -145.00 -79.00   0.50    6.00    --  -94.00 -67.00  53.76  132
109  ω   -152.00 -94.00   0.50    6.00    -- -102.41-135.00 149.00  116
110  ω   -160.00-103.00   0.50    6.00    --  -90.00 -74.00  95.19  114
111  ω   -157.00-121.00   0.50    6.00    --  -90.00 -74.00 154.91   72
112  ω   -162.00-132.00   0.50    6.00    --  -90.00 -73.00  72.69   60
113  ω   -161.00-112.00   0.50    6.00    --  -90.00 -73.00 -15.13   98
114  ω   -153.00-106.00   0.50    6.00    --  -82.00 -77.00-100.21   94
115  ω   -162.00 -69.00   0.50    6.00    --  -90.00 -72.00-124.17  186
116  ω   -161.00 -73.00   0.50    6.00    --  -94.00 -73.00-135.71  176
117  ω   -166.00 -76.00   0.50    6.00    --  -94.00 -66.00 -28.27  180
118  ω   -159.00 -71.00   0.50    6.00    --  -94.00 -76.00-175.13  176
119  ω   -166.00-113.00   0.50    6.00    --  -94.00 -68.00  11.58  106
120  ω   -166.00 -73.00   0.50    6.00    --  -94.00 -72.00 -63.03  186
121  ω   -165.00 -77.00   0.50    6.00    --  -94.00 -66.00 -78.48  176
122  ω   -160.00 -77.00   0.50    6.00    --  -94.00 -65.00-103.15  166
123  ω   -167.00-120.00   0.50    6.00    --  -94.00 -76.00-164.27   94
124  ω   -170.00 -75.00   0.50    6.00    --  -98.00 -77.00 -31.92  190
125  ω   -165.00-102.00   0.50    6.00    --  -94.00 -78.00  51.41  126
126  ω   -167.00-127.00   0.50    6.00    --  -94.00 -66.00 163.82   80
127  ω   -174.00-149.00   0.50    6.00    -- -102.41 -79.00 171.64   50
128  ω   -169.00 -75.00   0.50    6.00    --  -98.00 -76.00  31.52  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0033725000
_diffrn_orient_matrix_UB_12      0.0040252000
_diffrn_orient_matrix_UB_13      -0.0348472000
_diffrn_orient_matrix_UB_21      -0.0623194000
_diffrn_orient_matrix_UB_22      -0.0598046000
_diffrn_orient_matrix_UB_23      -0.0014515000
_diffrn_orient_matrix_UB_31      -0.0132265000
_diffrn_orient_matrix_UB_32      0.2801547000
_diffrn_orient_matrix_UB_33      0.0001548000
_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                5387
_reflns_number_total             5808
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5808
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0755
_refine_ls_restrained_S_all      1.089
_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)+(0.1089P)²+24.2692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2033
_refine_ls_wR_factor_ref         0.2077
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N2(H2), N3(H3)
2.b Ternary CH refined with riding coordinates:
 C2(H2A), C23(H23), C24(H24)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C16(H16), C17(H17), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), 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
Cl1 Cl 0.47240(5) 1.0795(2) 0.72398(3) 0.0586(3) Uani 1 1 d . . . . .
Cl2 Cl 0.39750(7) 0.6899(3) 0.73567(5) 0.0927(6) Uani 1 1 d . . . . .
Cl3 Cl 0.35885(5) 1.0873(3) 0.69707(3) 0.0646(4) Uani 1 1 d . . . . .
Cl4 Cl 0.31306(5) 1.0131(2) 0.52479(3) 0.0513(3) Uani 1 1 d . . . . .
Cl5 Cl 0.32190(6) 1.4307(2) 0.48482(5) 0.0776(5) Uani 1 1 d . . . . .
Cl6 Cl 0.39935(6) 1.0283(2) 0.48407(3) 0.0613(4) Uani 1 1 d . . . . .
S1 S 0.21164(4) 0.84189(19) 0.58483(2) 0.0401(3) Uani 1 1 d . . . . .
S2 S 0.72388(5) 0.7572(3) 0.69524(3) 0.0561(3) Uani 1 1 d . . . . .
O1 O 0.45649(10) 0.6104(4) 0.65505(6) 0.0286(5) Uani 1 1 d . . . . .
N1 N 0.41656(12) 0.2787(5) 0.62955(7) 0.0283(6) Uani 1 1 d . . . . .
N2 N 0.42404(12) 0.0597(5) 0.61236(8) 0.0305(7) Uani 1 1 d . . . . .
H2 H 0.411868 -0.073883 0.620094 0.037 Uiso 1 1 d R . . . .
N3 N 0.51919(12) 0.0462(5) 0.63297(7) 0.0290(6) Uani 1 1 d . . . . .
H3 H 0.518794 -0.088642 0.643359 0.035 Uiso 1 1 d R . . . .
N4 N 0.50987(12) 0.2676(5) 0.64968(7) 0.0276(6) Uani 1 1 d . . . . .
C1 C 0.46077(14) 0.3976(6) 0.64551(8) 0.0273(7) Uani 1 1 d . . . . .
C2 C 0.48181(14) 0.0460(6) 0.60547(9) 0.0286(7) Uani 1 1 d . . . . .
H2A H 0.489550 0.196138 0.594073 0.034 Uiso 1 1 calc R . . . .
C3 C 0.49159(14) -0.1744(6) 0.58564(8) 0.0288(7) Uani 1 1 d . . . . .
C4 C 0.45092(17) -0.2475(7) 0.56310(9) 0.0380(9) Uani 1 1 d . . . . .
H4 H 0.416402 -0.170778 0.561707 0.046 Uiso 1 1 calc R . . . .
C5 C 0.46140(19) -0.4325(8) 0.54287(10) 0.0427(9) Uani 1 1 d . . . . .
H5 H 0.433859 -0.479404 0.527973 0.051 Uiso 1 1 calc R . . . .
C6 C 0.51261(19) -0.5495(7) 0.54450(10) 0.0404(9) Uani 1 1 d . . . . .
H6 H 0.519552 -0.673350 0.530711 0.048 Uiso 1 1 calc R . . . .
C7 C 0.55313(17) -0.4801(7) 0.56680(10) 0.0403(9) Uani 1 1 d . . . . .
H7 H 0.587502 -0.558018 0.568071 0.048 Uiso 1 1 calc R . . . .
C8 C 0.54290(16) -0.2941(7) 0.58739(10) 0.0350(8) Uani 1 1 d . . . . .
H8 H 0.570397 -0.249353 0.602409 0.042 Uiso 1 1 calc R . . . .
C9 C 0.36746(14) 0.4174(6) 0.61971(9) 0.0292(7) Uani 1 1 d . . . . .
C10 C 0.34574(15) 0.4014(7) 0.58981(9) 0.0327(8) Uani 1 1 d . . . . .
H10 H 0.362659 0.300012 0.576386 0.039 Uiso 1 1 calc R . . . .
C11 C 0.29879(16) 0.5362(7) 0.57980(9) 0.0349(8) Uani 1 1 d . . . . .
H11 H 0.284444 0.523955 0.559685 0.042 Uiso 1 1 calc R . . . .
C12 C 0.27288(14) 0.6896(7) 0.59950(9) 0.0307(7) Uani 1 1 d . . . . .
C13 C 0.29426(14) 0.7031(7) 0.62969(9) 0.0304(7) Uani 1 1 d . . . . .
H13 H 0.277335 0.804698 0.643092 0.037 Uiso 1 1 calc R . . . .
C14 C 0.34108(14) 0.5645(7) 0.63991(9) 0.0309(8) Uani 1 1 d . . . . .
H14 H 0.354632 0.570492 0.660198 0.037 Uiso 1 1 calc R . . . .
C15 C 0.55984(14) 0.3876(6) 0.66181(8) 0.0291(7) Uani 1 1 d . . . . .
C16 C 0.60815(15) 0.3530(7) 0.64746(9) 0.0320(8) Uani 1 1 d . . . . .
H16 H 0.607683 0.252193 0.630404 0.038 Uiso 1 1 calc R . . . .
C17 C 0.65683(16) 0.4692(8) 0.65869(10) 0.0390(9) Uani 1 1 d . . . . .
H17 H 0.688852 0.443700 0.649066 0.047 Uiso 1 1 calc R . . . .
C18 C 0.65893(16) 0.6221(8) 0.68384(10) 0.0377(9) Uani 1 1 d . . . . .
C19 C 0.61093(17) 0.6522(8) 0.69851(10) 0.0400(9) Uani 1 1 d . . . . .
H19 H 0.611688 0.751541 0.715696 0.048 Uiso 1 1 calc R . . . .
C20 C 0.56146(16) 0.5340(7) 0.68757(9) 0.0336(8) Uani 1 1 d . . . . .
H20 H 0.529748 0.553965 0.697633 0.040 Uiso 1 1 calc R . . . .
C21 C 0.20559(17) 1.0963(8) 0.61077(11) 0.0421(9) Uani 1 1 d . . . . .
H21A H 0.177305 1.208659 0.602587 0.063 Uiso 1 1 calc GR . . . .
H21B H 0.240298 1.182855 0.613724 0.063 Uiso 1 1 calc GR . . . .
H21C H 0.195956 1.032891 0.629823 0.063 Uiso 1 1 calc GR . . . .
C22 C 0.7084(2) 0.9863(10) 0.72246(13) 0.0609(14) Uani 1 1 d . . . . .
H22A H 0.680304 1.096521 0.713588 0.091 Uiso 1 1 calc GR . . . .
H22B H 0.741263 1.079665 0.728644 0.091 Uiso 1 1 calc GR . . . .
H22C H 0.695381 0.905600 0.739756 0.091 Uiso 1 1 calc GR . . . .
C23 C 0.41560(17) 0.9024(9) 0.70904(10) 0.0434(10) Uani 1 1 d . . . . .
H23 H 0.426631 0.810135 0.691517 0.052 Uiso 1 1 calc R . . . .
C24 C 0.33088(19) 1.1100(8) 0.48923(11) 0.0448(10) Uani 1 1 d . . . . .
H24 H 0.306314 1.026080 0.473652 0.054 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
Cl1 C23 1.754(4) . ?
Cl2 C23 1.729(5) . ?
Cl3 C23 1.741(4) . ?
Cl4 C24 1.753(5) . ?
Cl5 C24 1.747(5) . ?
Cl6 C24 1.753(5) . ?
S1 C12 1.767(4) . ?
S1 C21 1.802(5) . ?
S2 C18 1.765(4) . ?
S2 C22 1.789(5) . ?
O1 C1 1.227(4) . ?
N1 N2 1.423(4) . ?
N1 C1 1.386(4) . ?
N1 C9 1.438(4) . ?
N2 H2 0.8598 . ?
N2 C2 1.463(4) . ?
N3 H3 0.8598 . ?
N3 N4 1.431(4) . ?
N3 C2 1.451(5) . ?
N4 C1 1.378(4) . ?
N4 C15 1.433(4) . ?
C2 H2A 0.9800 . ?
C2 C3 1.508(5) . ?
C3 C4 1.395(5) . ?
C3 C8 1.396(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.392(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.384(5) . ?
C9 C14 1.394(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.388(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.393(5) . ?
C12 C13 1.393(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.398(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.396(5) . ?
C15 C20 1.385(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(6) . ?
C18 C19 1.394(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.404(5) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9800 . ?
C24 H24 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 S1 C21 103.4(2) . . ?
C18 S2 C22 103.9(2) . . ?
N2 N1 C9 114.1(3) . . ?
C1 N1 N2 121.7(3) . . ?
C1 N1 C9 119.7(3) . . ?
N1 N2 H2 114.3 . . ?
N1 N2 C2 109.0(3) . . ?
C2 N2 H2 114.3 . . ?
N4 N3 H3 114.4 . . ?
N4 N3 C2 108.7(3) . . ?
C2 N3 H3 114.4 . . ?
N3 N4 C15 113.6(3) . . ?
C1 N4 N3 121.9(3) . . ?
C1 N4 C15 120.8(3) . . ?
O1 C1 N1 121.4(3) . . ?
O1 C1 N4 121.7(3) . . ?
N4 C1 N1 116.9(3) . . ?
N2 C2 H2A 107.4 . . ?
N2 C2 C3 111.5(3) . . ?
N3 C2 N2 111.1(3) . . ?
N3 C2 H2A 107.4 . . ?
N3 C2 C3 111.8(3) . . ?
C3 C2 H2A 107.4 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 C8 118.5(4) . . ?
C8 C3 C2 121.1(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.7(4) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.3(4) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.5(4) . . ?
C8 C7 H7 119.8 . . ?
C3 C8 H8 119.8 . . ?
C7 C8 C3 120.4(4) . . ?
C7 C8 H8 119.8 . . ?
C10 C9 N1 119.4(3) . . ?
C10 C9 C14 119.6(3) . . ?
C14 C9 N1 121.0(3) . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.2(4) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.8(4) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 S1 117.1(3) . . ?
C11 C12 C13 119.0(3) . . ?
C13 C12 S1 123.8(3) . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 120.1(4) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 N4 119.0(3) . . ?
C20 C15 N4 121.6(3) . . ?
C20 C15 C16 119.4(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.9(4) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.6(4) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 S2 116.2(3) . . ?
C17 C18 C19 118.4(4) . . ?
C19 C18 S2 125.4(3) . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.6(4) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 120.0(4) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
S1 C21 H21A 109.5 . . ?
S1 C21 H21B 109.5 . . ?
S1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
S2 C22 H22A 109.5 . . ?
S2 C22 H22B 109.5 . . ?
S2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Cl1 C23 H23 108.2 . . ?
Cl2 C23 Cl1 109.9(2) . . ?
Cl2 C23 Cl3 110.0(2) . . ?
Cl2 C23 H23 108.2 . . ?
Cl3 C23 Cl1 112.1(3) . . ?
Cl3 C23 H23 108.2 . . ?
Cl4 C24 H24 108.3 . . ?
Cl5 C24 Cl4 110.8(3) . . ?
Cl5 C24 Cl6 110.0(3) . . ?
Cl5 C24 H24 108.3 . . ?
Cl6 C24 Cl4 111.0(3) . . ?
Cl6 C24 H24 108.3 . . ?

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 C12 C13 C14 176.0(3) . . . . ?
S2 C18 C19 C20 -179.5(3) . . . . ?
N1 N2 C2 N3 58.0(4) . . . . ?
N1 N2 C2 C3 -176.5(3) . . . . ?
N1 C9 C10 C11 -179.2(3) . . . . ?
N1 C9 C14 C13 178.3(3) . . . . ?
N2 N1 C1 O1 164.8(3) . . . . ?
N2 N1 C1 N4 -14.1(5) . . . . ?
N2 N1 C9 C10 -26.9(4) . . . . ?
N2 N1 C9 C14 152.2(3) . . . . ?
N2 C2 C3 C4 36.5(5) . . . . ?
N2 C2 C3 C8 -149.7(3) . . . . ?
N3 N4 C1 O1 -165.2(3) . . . . ?
N3 N4 C1 N1 13.7(5) . . . . ?
N3 N4 C15 C16 26.0(5) . . . . ?
N3 N4 C15 C20 -153.1(3) . . . . ?
N3 C2 C3 C4 161.6(3) . . . . ?
N3 C2 C3 C8 -24.6(5) . . . . ?
N4 N3 C2 N2 -58.2(3) . . . . ?
N4 N3 C2 C3 176.5(3) . . . . ?
N4 C15 C16 C17 179.4(3) . . . . ?
N4 C15 C20 C19 -178.9(4) . . . . ?
C1 N1 N2 C2 -21.0(4) . . . . ?
C1 N1 C9 C10 129.7(4) . . . . ?
C1 N1 C9 C14 -51.2(5) . . . . ?
C1 N4 C15 C16 -132.6(4) . . . . ?
C1 N4 C15 C20 48.2(5) . . . . ?
C2 N3 N4 C1 21.9(4) . . . . ?
C2 N3 N4 C15 -136.4(3) . . . . ?
C2 C3 C4 C5 173.5(4) . . . . ?
C2 C3 C8 C7 -173.2(3) . . . . ?
C3 C4 C5 C6 -0.1(7) . . . . ?
C4 C3 C8 C7 0.8(6) . . . . ?
C4 C5 C6 C7 0.4(7) . . . . ?
C5 C6 C7 C8 -0.2(6) . . . . ?
C6 C7 C8 C3 -0.4(6) . . . . ?
C8 C3 C4 C5 -0.5(6) . . . . ?
C9 N1 N2 C2 135.1(3) . . . . ?
C9 N1 C1 O1 10.0(5) . . . . ?
C9 N1 C1 N4 -168.9(3) . . . . ?
C9 C10 C11 C12 0.2(6) . . . . ?
C10 C9 C14 C13 -2.6(5) . . . . ?
C10 C11 C12 S1 -177.2(3) . . . . ?
C10 C11 C12 C13 -1.0(6) . . . . ?
C11 C12 C13 C14 0.1(5) . . . . ?
C12 C13 C14 C9 1.8(5) . . . . ?
C14 C9 C10 C11 1.7(5) . . . . ?
C15 N4 C1 O1 -8.4(5) . . . . ?
C15 N4 C1 N1 170.5(3) . . . . ?
C15 C16 C17 C18 -0.6(6) . . . . ?
C16 C15 C20 C19 2.0(6) . . . . ?
C16 C17 C18 S2 -179.8(3) . . . . ?
C16 C17 C18 C19 1.9(6) . . . . ?
C17 C18 C19 C20 -1.3(6) . . . . ?
C18 C19 C20 C15 -0.6(6) . . . . ?
C20 C15 C16 C17 -1.4(6) . . . . ?
C21 S1 C12 C11 -159.8(3) . . . . ?
C21 S1 C12 C13 24.2(4) . . . . ?
C22 S2 C18 C17 168.5(4) . . . . ?
C22 S2 C18 C19 -13.3(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
;

####################################################################### 
# 
# 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_vjk2033
_database_code_depnum_ccdc_archive 'CCDC 2109620'
loop_
_audit_author_name
_audit_author_address
'Stephen A. Moggach'
;University of Western Australia
Australia
;
_audit_update_record             
;
2021-09-14 deposited with the CCDC.	2021-12-16 downloaded from the CCDC.
;
_audit_creation_date             2021-08-29
_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         'C22 H19 N4 O'
_chemical_formula_sum            'C22 H19 N4 O'
_chemical_formula_weight         355.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N4 O1 C22 H20'
_chemical_oxdiff_usercomment     'Varshini for Low'
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                   7.1902(2)
_cell_length_b                   11.2885(3)
_cell_length_c                   21.8846(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.343(3)
_cell_angle_gamma                90
_cell_volume                     1776.27(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5827
_cell_measurement_temperature    99.8(6)
_cell_measurement_theta_max      73.6200
_cell_measurement_theta_min      4.0430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48493
_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            'clear dark red'
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             748
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -3 -2 0.1064
1 4 -11 0.0342
-2 -3 11 0.0427
0 3 -13 0.0285
-1 -2 13 0.0313
0 0 -14 0.0306
0 1 -14 0.0285
0 -2 -14 0.0392
-1 -1 -13 0.0363
-4 3 2 0.1330
0 2 14 0.0269
0 -6 -9 0.0565
1 7 5 0.0425
0 -7 -1 0.0632
-3 -5 4 0.0572
1 7 -4 0.0422
0 -6 7 0.0553
0 -3 13 0.0323
0 3 -13 0.0286
0 -1 14 0.0285
-2 -1 -13 0.0392
1 4 12 0.0380
1 6 5 0.0456
-4 -4 -4 0.0587

_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.057
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.3493 -2.5525 -1.5925 -0.0090 0.0015 -1.0000
0.6425 4.4654 -11.0990 -0.9724 -0.2330 0.0090
-2.1473 -3.2602 10.9501 0.9119 0.2182 0.3475
0.1200 2.6377 -13.2468 -0.8529 -0.5221 0.0090
-1.1692 -1.9333 13.2507 0.8294 0.5075 0.2337
0.1229 0.2275 -14.1933 -0.6456 -0.7550 -0.1151
-0.4181 0.5540 -14.0965 -0.6498 -0.7601 0.0090
0.1588 -2.1691 -13.5618 -0.3727 -0.8980 -0.2337
-1.3675 -1.2989 -13.3170 -0.3806 -0.9177 0.1137
-4.3312 2.6173 1.6567 0.0042 0.0080 1.0000
0.2974 1.9358 13.6629 0.3799 0.9155 0.1325
-0.0732 -5.7773 -8.7342 0.2198 -0.9188 -0.3278
0.9537 6.6800 5.0417 -0.5144 0.8406 0.1700
-0.0441 -7.3082 -1.0256 0.7111 -0.6083 -0.3525
-2.9968 -5.1976 4.1665 0.8568 -0.3550 0.3741
0.9230 6.9329 -3.6453 -0.9163 0.3802 0.1262
0.0572 -6.3195 7.1840 0.9609 -0.0763 -0.2660
-0.1984 -2.5905 13.2745 0.8529 0.5221 0.0090
-0.0904 2.7601 -13.1510 -0.8515 -0.5212 0.0575
0.3396 -0.5068 14.1242 0.6498 0.7601 0.0090
-1.8693 -0.9498 -12.8461 -0.3727 -0.8980 0.2338
1.2555 3.6072 11.7320 0.0789 0.9968 0.0090
1.4941 6.4532 4.9211 -0.5214 0.8518 0.0507
-3.5800 -4.3132 -3.5349 0.4583 -0.7495 0.4777

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0855
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15068
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.096
_diffrn_reflns_theta_min         4.040
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.8(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     23.00 119.00   0.50    0.20    --   45.95  77.00  90.00  192
  2  ω     23.00 119.00   0.50    0.20    --   45.95  77.00  30.00  192
  3  ω     23.00 119.00   0.50    0.20    --   45.95  77.00 -90.00  192
  4  ω     34.00 121.00   0.50    0.20    --   45.95  29.00-154.00  174
  5  ω     90.00 177.00   0.50    0.80    --  102.41  29.00-154.00  174
  6  ω     54.00 119.00   0.50    0.20    --   45.95 154.00  71.00  130
  7  ω     74.00 119.00   0.50    0.20    --   45.95 125.00 150.00   90
  8  ω     74.00 119.00   0.50    0.20    --   45.95 125.00 -60.00   90
  9  ω     30.00  71.00   0.50    0.80    --  102.41 -61.00-180.00   82
 10  ω     30.00 105.00   0.50    0.80    --  102.41 -77.00 -90.00  150
 11  ω     30.00  71.00   0.50    0.80    --  102.41 -61.00 -30.00   82
 12  ω    -28.00  26.00   0.50    0.20    --   45.95 -19.00 -90.00  108
 13  ω   -177.00 -90.00   0.50    0.80    -- -102.41 -30.00-150.00  174
 14  ω   -177.00 -89.00   0.50    0.80    -- -102.41 -15.00 -30.00  176
 15  ω   -177.00-135.00   0.50    0.80    -- -102.41 -15.00  90.00   84
 16  ω   -105.00 -30.00   0.50    0.80    -- -102.41  96.00  18.00  150
 17  ω    -71.00 -30.00   0.50    0.80    -- -102.41  61.00 -60.00   82
 18  ω   -105.00 -30.00   0.50    0.80    -- -102.41  77.00-180.00  150
 19  ω     30.00 111.00   0.50    0.80    --  102.41-125.00  30.00  162
 20  ω     30.00 109.00   0.50    0.80    --  102.41-120.00-170.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0466728000
_diffrn_orient_matrix_UB_12      -0.1031142000
_diffrn_orient_matrix_UB_13      0.0434279000
_diffrn_orient_matrix_UB_21      0.0645669000
_diffrn_orient_matrix_UB_22      0.0751359000
_diffrn_orient_matrix_UB_23      0.0549560000
_diffrn_orient_matrix_UB_31      -0.1988638000
_diffrn_orient_matrix_UB_32      0.0484352000
_diffrn_orient_matrix_UB_33      0.0071603000
_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                2857
_reflns_number_total             3465
_reflns_odcompleteness_completeness 98.22
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3465
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0568
_refine_ls_restrained_S_all      1.034
_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)+(0.1027P)²+0.2093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1476
_refine_ls_wR_factor_ref         0.1590
_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:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C16(H16), C17(H17), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O1 O 0.73753(16) 0.09092(10) 0.47788(5) 0.0292(3) Uani 1 1 d . . . . .
N1 N 0.77569(17) 0.27743(12) 0.43833(6) 0.0229(3) Uani 1 1 d . . . . .
N2 N 0.77619(17) 0.39832(12) 0.44499(6) 0.0243(3) Uani 1 1 d . . . . .
N3 N 0.72114(18) 0.37124(12) 0.55128(6) 0.0244(3) Uani 1 1 d . . . . .
N4 N 0.71588(18) 0.25136(12) 0.54150(6) 0.0233(3) Uani 1 1 d . . . . .
C1 C 0.7429(2) 0.19755(15) 0.48527(7) 0.0238(4) Uani 1 1 d . . . . .
C2 C 0.74967(19) 0.43662(14) 0.50175(7) 0.0217(3) Uani 1 1 d . . . . .
C3 C 0.75238(19) 0.56687(14) 0.51093(7) 0.0224(4) Uani 1 1 d . . . . .
C4 C 0.8131(2) 0.64165(15) 0.46425(7) 0.0252(4) Uani 1 1 d . . . . .
H4 H 0.853853 0.609647 0.427532 0.030 Uiso 1 1 calc R . . . .
C5 C 0.8128(2) 0.76385(15) 0.47253(8) 0.0277(4) Uani 1 1 d . . . . .
H5 H 0.852273 0.813160 0.441130 0.033 Uiso 1 1 calc R . . . .
C6 C 0.7544(2) 0.81236(15) 0.52694(8) 0.0278(4) Uani 1 1 d . . . . .
H6 H 0.753853 0.894102 0.532211 0.033 Uiso 1 1 calc R . . . .
C7 C 0.6963(2) 0.73848(15) 0.57382(8) 0.0290(4) Uani 1 1 d . . . . .
H7 H 0.658229 0.770981 0.610738 0.035 Uiso 1 1 calc R . . . .
C8 C 0.6946(2) 0.61662(15) 0.56599(8) 0.0261(4) Uani 1 1 d . . . . .
H8 H 0.654782 0.567856 0.597568 0.031 Uiso 1 1 calc R . . . .
C9 C 0.7964(2) 0.23851(14) 0.37636(7) 0.0234(4) Uani 1 1 d . . . . .
C10 C 0.7176(2) 0.30698(15) 0.33011(8) 0.0268(4) Uani 1 1 d . . . . .
H10 H 0.648526 0.373913 0.339948 0.032 Uiso 1 1 calc R . . . .
C11 C 0.7414(2) 0.27593(15) 0.26985(8) 0.0278(4) Uani 1 1 d . . . . .
H11 H 0.688634 0.322822 0.239412 0.033 Uiso 1 1 calc R . . . .
C12 C 0.8430(2) 0.17582(15) 0.25339(7) 0.0254(4) Uani 1 1 d . . . . .
C13 C 0.9198(2) 0.10781(15) 0.30031(8) 0.0266(4) Uani 1 1 d . . . . .
H13 H 0.987383 0.040303 0.290441 0.032 Uiso 1 1 calc R . . . .
C14 C 0.8983(2) 0.13794(15) 0.36131(7) 0.0255(4) Uani 1 1 d . . . . .
H14 H 0.951513 0.091424 0.391825 0.031 Uiso 1 1 calc R . . . .
C15 C 0.6942(2) 0.18262(14) 0.59623(7) 0.0226(4) Uani 1 1 d . . . . .
C16 C 0.7892(2) 0.22015(15) 0.64823(7) 0.0249(4) Uani 1 1 d . . . . .
H16 H 0.871470 0.283570 0.646062 0.030 Uiso 1 1 calc R . . . .
C17 C 0.7608(2) 0.16252(15) 0.70343(7) 0.0264(4) Uani 1 1 d . . . . .
H17 H 0.822664 0.188839 0.738308 0.032 Uiso 1 1 calc R . . . .
C18 C 0.6411(2) 0.06597(15) 0.70739(8) 0.0262(4) Uani 1 1 d . . . . .
C19 C 0.5501(2) 0.02879(14) 0.65453(8) 0.0264(4) Uani 1 1 d . . . . .
H19 H 0.470942 -0.036228 0.656359 0.032 Uiso 1 1 calc R . . . .
C20 C 0.5747(2) 0.08655(14) 0.59886(7) 0.0249(4) Uani 1 1 d . . . . .
H20 H 0.511832 0.060970 0.564021 0.030 Uiso 1 1 calc R . . . .
C21 C 0.8646(2) 0.14231(17) 0.18756(8) 0.0310(4) Uani 1 1 d . . . . .
H21A H 0.981179 0.102352 0.182137 0.047 Uiso 1 1 calc GR . . . .
H21B H 0.861725 0.212446 0.162765 0.047 Uiso 1 1 calc GR . . . .
H21C H 0.764711 0.090675 0.175619 0.047 Uiso 1 1 calc GR . . . .
C22 C 0.6117(2) 0.00327(17) 0.76740(8) 0.0337(4) Uani 1 1 d . . . . .
H22A H 0.506899 -0.049059 0.763900 0.051 Uiso 1 1 calc GR . . . .
H22B H 0.588592 0.060637 0.798837 0.051 Uiso 1 1 calc GR . . . .
H22C H 0.720802 -0.041678 0.777666 0.051 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
O1 C1 1.215(2) . ?
N1 N2 1.3725(19) . ?
N1 C1 1.388(2) . ?
N1 C9 1.434(2) . ?
N2 C2 1.330(2) . ?
N3 N4 1.3706(19) . ?
N3 C2 1.328(2) . ?
N4 C1 1.387(2) . ?
N4 C15 1.4363(19) . ?
C2 C3 1.484(2) . ?
C3 C4 1.397(2) . ?
C3 C8 1.395(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.391(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.388(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.392(2) . ?
C9 C14 1.392(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.394(2) . ?
C12 C13 1.394(2) . ?
C12 C21 1.498(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.390(2) . ?
C15 C20 1.385(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.388(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.392(2) . ?
C18 C19 1.390(2) . ?
C18 C22 1.508(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.394(2) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
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
N2 N1 C1 124.59(13) . . ?
N2 N1 C9 113.88(12) . . ?
C1 N1 C9 121.32(13) . . ?
C2 N2 N1 114.97(13) . . ?
C2 N3 N4 115.17(13) . . ?
N3 N4 C1 124.55(13) . . ?
N3 N4 C15 113.96(12) . . ?
C1 N4 C15 121.31(13) . . ?
O1 C1 N1 123.39(14) . . ?
O1 C1 N4 123.19(14) . . ?
N4 C1 N1 113.41(14) . . ?
N2 C2 C3 116.53(14) . . ?
N3 C2 N2 127.24(15) . . ?
N3 C2 C3 116.22(14) . . ?
C4 C3 C2 120.23(14) . . ?
C8 C3 C2 120.81(14) . . ?
C8 C3 C4 118.97(15) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.20(15) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.47(15) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.63(15) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.47(15) . . ?
C8 C7 H7 119.8 . . ?
C3 C8 H8 119.9 . . ?
C7 C8 C3 120.25(15) . . ?
C7 C8 H8 119.9 . . ?
C10 C9 N1 118.26(14) . . ?
C10 C9 C14 119.58(15) . . ?
C14 C9 N1 122.11(14) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.19(15) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.50(16) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C21 120.71(16) . . ?
C13 C12 C11 117.53(15) . . ?
C13 C12 C21 121.76(15) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 C12 121.88(15) . . ?
C14 C13 H13 119.1 . . ?
C9 C14 H14 120.3 . . ?
C13 C14 C9 119.31(15) . . ?
C13 C14 H14 120.3 . . ?
C16 C15 N4 117.58(14) . . ?
C20 C15 N4 121.86(14) . . ?
C20 C15 C16 120.44(15) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.70(15) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.03(15) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C22 120.77(16) . . ?
C19 C18 C17 118.20(15) . . ?
C19 C18 C22 121.03(15) . . ?
C18 C19 H19 119.2 . . ?
C18 C19 C20 121.65(15) . . ?
C20 C19 H19 119.2 . . ?
C15 C20 C19 118.97(15) . . ?
C15 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C12 C21 H21A 109.5 . . ?
C12 C21 H21B 109.5 . . ?
C12 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C2 N3 -0.9(2) . . . . ?
N1 N2 C2 C3 179.03(12) . . . . ?
N1 C9 C10 C11 176.97(13) . . . . ?
N1 C9 C14 C13 -177.26(13) . . . . ?
N2 N1 C1 O1 177.68(13) . . . . ?
N2 N1 C1 N4 -2.1(2) . . . . ?
N2 N1 C9 C10 -34.23(18) . . . . ?
N2 N1 C9 C14 143.17(14) . . . . ?
N2 C2 C3 C4 -11.1(2) . . . . ?
N2 C2 C3 C8 168.83(14) . . . . ?
N3 N4 C1 O1 179.97(14) . . . . ?
N3 N4 C1 N1 -0.3(2) . . . . ?
N3 N4 C15 C16 -38.96(18) . . . . ?
N3 N4 C15 C20 137.12(14) . . . . ?
N3 C2 C3 C4 168.80(13) . . . . ?
N3 C2 C3 C8 -11.2(2) . . . . ?
N4 N3 C2 N2 -1.2(2) . . . . ?
N4 N3 C2 C3 178.88(12) . . . . ?
N4 C15 C16 C17 174.68(13) . . . . ?
N4 C15 C20 C19 -175.46(13) . . . . ?
C1 N1 N2 C2 2.6(2) . . . . ?
C1 N1 C9 C10 140.74(15) . . . . ?
C1 N1 C9 C14 -41.9(2) . . . . ?
C1 N4 C15 C16 136.43(15) . . . . ?
C1 N4 C15 C20 -47.5(2) . . . . ?
C2 N3 N4 C1 1.8(2) . . . . ?
C2 N3 N4 C15 177.03(12) . . . . ?
C2 C3 C4 C5 178.96(13) . . . . ?
C2 C3 C8 C7 -179.45(14) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C4 C3 C8 C7 0.5(2) . . . . ?
C4 C5 C6 C7 0.3(2) . . . . ?
C5 C6 C7 C8 -0.8(2) . . . . ?
C6 C7 C8 C3 0.4(2) . . . . ?
C8 C3 C4 C5 -1.0(2) . . . . ?
C9 N1 N2 C2 177.42(12) . . . . ?
C9 N1 C1 O1 3.3(2) . . . . ?
C9 N1 C1 N4 -176.47(13) . . . . ?
C9 C10 C11 C12 0.4(2) . . . . ?
C10 C9 C14 C13 0.1(2) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
C10 C11 C12 C21 178.92(14) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?
C12 C13 C14 C9 0.4(2) . . . . ?
C14 C9 C10 C11 -0.5(2) . . . . ?
C15 N4 C1 O1 5.1(2) . . . . ?
C15 N4 C1 N1 -175.18(13) . . . . ?
C15 C16 C17 C18 1.3(2) . . . . ?
C16 C15 C20 C19 0.5(2) . . . . ?
C16 C17 C18 C19 -0.1(2) . . . . ?
C16 C17 C18 C22 179.61(14) . . . . ?
C17 C18 C19 C20 -0.8(2) . . . . ?
C18 C19 C20 C15 0.6(2) . . . . ?
C20 C15 C16 C17 -1.4(2) . . . . ?
C21 C12 C13 C14 -179.31(14) . . . . ?
C22 C18 C19 C20 179.43(14) . . . . ?

_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
;

####################################################################### 
# 
# 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_JW-805-2-Ver
_database_code_depnum_ccdc_archive 'CCDC 2109622'
loop_
_audit_author_name
_audit_author_address
'Stephen A. Moggach'
;University of Western Australia
Australia
;
_audit_update_record             
;
2021-09-14 deposited with the CCDC.	2021-12-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H13 I2 N4 O'
_chemical_formula_sum            'C20 H13 I2 N4 O'
_chemical_formula_weight         579.14

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.0177(2)
_cell_length_b                   10.1392(5)
_cell_length_c                   23.1774(9)
_cell_angle_alpha                87.900(4)
_cell_angle_beta                 86.840(4)
_cell_angle_gamma                80.762(4)
_cell_volume                     930.13(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    99.95(10)
_cell_measurement_reflns_used    3204
_cell_measurement_theta_min      4.3910
_cell_measurement_theta_max      28.6420

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.068
_exptl_crystal_F_000             550
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    3.399
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.87254
_exptl_absorpt_correction_T_max  1.00000
_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.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.874
_oxdiff_exptl_absorpt_empirical_full_max 1.207
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      99.95(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4738
_diffrn_reflns_number            6834
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.290
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             6834
_reflns_number_gt                4765
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6834
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0821
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_restrained_S_all      0.877
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1176438000
_diffrn_orient_matrix_UB_12      0.0383315000
_diffrn_orient_matrix_UB_13      0.0192054000
_diffrn_orient_matrix_UB_21      -0.0998857000
_diffrn_orient_matrix_UB_22      0.0245116000
_diffrn_orient_matrix_UB_23      -0.0235568000
_diffrn_orient_matrix_UB_31      -0.0908525000
_diffrn_orient_matrix_UB_32      -0.0543804000
_diffrn_orient_matrix_UB_33      0.0040472000

_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.6947 8471 2556 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.3053 8509 2556 nmt -0.9967 -0.0031 0.0187 0.0213 -1.0011 0.0284 -0.0036
-0.0214 1.0006
_oxdiff_twin_integration_method  simultaneous
_twin_special_details            
;
Component 2 rotated by 179.5217° 
 around [0.01 0.01 1.00] (reciprocal) or [-0.00 -0.01 1.00] (direct)
;

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
C14 C 0.3592(15) 0.2685(6) -0.1417(2) 0.0190(12) Uani 1 1 d . . . . .
H14 H 0.258978 0.328688 -0.169264 0.023 Uiso 1 1 calc R U . . .
C1 C 0.3981(15) 0.1460(6) -0.2581(2) 0.0198(13) Uani 1 1 d . . . . .
C2 C 0.1391(13) -0.0883(5) -0.2486(2) 0.0140(11) Uani 1 1 d . . . . .
C3 C 0.0113(14) -0.2180(5) -0.2435(2) 0.0152(12) Uani 1 1 d . . . . .
C4 C -0.0282(14) -0.2801(5) -0.1897(2) 0.0170(12) Uani 1 1 d . . . . .
H4 H 0.019392 -0.238985 -0.156627 0.020 Uiso 1 1 calc R U . . .
C5 C -0.1376(15) -0.4027(6) -0.1851(2) 0.0214(13) Uani 1 1 d . . . . .
H5 H -0.162142 -0.443766 -0.148922 0.026 Uiso 1 1 calc R U . . .
C6 C -0.2113(15) -0.4648(6) -0.2343(2) 0.0212(13) Uani 1 1 d . . . . .
H6 H -0.285363 -0.547256 -0.231240 0.025 Uiso 1 1 calc R U . . .
C7 C -0.1736(15) -0.4033(6) -0.2876(2) 0.0221(13) Uani 1 1 d . . . . .
H7 H -0.221204 -0.444761 -0.320652 0.027 Uiso 1 1 calc R U . . .
C8 C -0.0654(14) -0.2803(6) -0.2926(2) 0.0201(13) Uani 1 1 d . . . . .
H8 H -0.043848 -0.239047 -0.328797 0.024 Uiso 1 1 calc R U . . .
C9 C 0.4217(13) 0.1334(5) -0.1522(2) 0.0151(11) Uani 1 1 d . . . . .
C10 C 0.5668(14) 0.0418(5) -0.1109(2) 0.0178(12) Uani 1 1 d . . . . .
H10 H 0.602991 -0.049330 -0.117745 0.021 Uiso 1 1 calc R U . . .
C11 C 0.6561(14) 0.0887(6) -0.0595(2) 0.0175(12) Uani 1 1 d . . . . .
H11 H 0.757882 0.028856 -0.031940 0.021 Uiso 1 1 calc R U . . .
C12 C 0.5949(14) 0.2234(6) -0.0491(2) 0.0188(12) Uani 1 1 d . . . . .
C13 C 0.4458(14) 0.3135(5) -0.0902(2) 0.0183(12) Uani 1 1 d . . . . .
H13 H 0.404579 0.404421 -0.082983 0.022 Uiso 1 1 calc R U . . .
C15 C 0.3437(14) 0.1397(5) -0.3615(2) 0.0174(12) Uani 1 1 d . . . . .
C16 C 0.5527(15) 0.0632(6) -0.4016(2) 0.0225(13) Uani 1 1 d . . . . .
H16 H 0.658750 -0.022354 -0.391638 0.027 Uiso 1 1 calc R U . . .
C17 C 0.6005(16) 0.1170(6) -0.4569(2) 0.0269(14) Uani 1 1 d . . . . .
H17 H 0.743070 0.068184 -0.484182 0.032 Uiso 1 1 calc R U . . .
C18 C 0.4361(15) 0.2430(6) -0.4712(2) 0.0218(13) Uani 1 1 d . . . . .
C19 C 0.2237(15) 0.3182(6) -0.4313(2) 0.0224(13) Uani 1 1 d . . . . .
H19 H 0.112821 0.402826 -0.441447 0.027 Uiso 1 1 calc R U . . .
C20 C 0.1794(15) 0.2649(6) -0.3759(2) 0.0226(13) Uani 1 1 d . . . . .
H20 H 0.038599 0.314134 -0.348469 0.027 Uiso 1 1 calc R U . . .
N1 N 0.3274(12) 0.0821(4) -0.20509(17) 0.0160(10) Uani 1 1 d . . . . .
N2 N 0.2090(12) -0.0364(4) -0.19953(18) 0.0170(10) Uani 1 1 d . . . . .
N3 N 0.1659(12) -0.0337(4) -0.30196(18) 0.0185(10) Uani 1 1 d . . . . .
N4 N 0.2921(12) 0.0838(4) -0.30455(18) 0.0176(10) Uani 1 1 d . . . . .
O1 O 0.5414(10) 0.2417(4) -0.26303(15) 0.0219(9) Uani 1 1 d . . . . .
I1 I 0.73224(10) 0.28984(4) 0.02950(2) 0.02575(13) Uani 1 1 d . . . . .
I2 I 0.52352(11) 0.32080(4) -0.55490(2) 0.03189(14) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C14 C13 1.374(7) . ?
C14 C9 1.381(8) . ?
C1 O1 1.204(6) . ?
C1 N4 1.388(7) . ?
C1 N1 1.404(7) . ?
C2 N2 1.331(6) . ?
C2 N3 1.343(7) . ?
C2 C3 1.485(7) . ?
C3 C4 1.389(7) . ?
C3 C8 1.393(7) . ?
C4 C5 1.381(7) . ?
C5 C6 1.392(8) . ?
C6 C7 1.375(8) . ?
C7 C8 1.384(8) . ?
C9 C10 1.393(8) . ?
C9 N1 1.441(6) . ?
C10 C11 1.384(7) . ?
C11 C12 1.376(7) . ?
C12 C13 1.388(8) . ?
C12 I1 2.097(5) . ?
C15 C20 1.372(8) . ?
C15 C16 1.388(8) . ?
C15 N4 1.435(7) . ?
C16 C17 1.391(8) . ?
C17 C18 1.378(8) . ?
C18 C19 1.386(8) . ?
C18 I2 2.101(5) . ?
C19 C20 1.389(8) . ?
N1 N2 1.361(6) . ?
N3 N4 1.365(6) . ?

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 C14 C9 119.7(5) . . ?
O1 C1 N4 123.6(5) . . ?
O1 C1 N1 124.2(5) . . ?
N4 C1 N1 112.1(5) . . ?
N2 C2 N3 126.5(5) . . ?
N2 C2 C3 116.7(4) . . ?
N3 C2 C3 116.8(4) . . ?
C4 C3 C8 119.0(5) . . ?
C4 C3 C2 120.3(5) . . ?
C8 C3 C2 120.7(5) . . ?
C5 C4 C3 120.4(5) . . ?
C4 C5 C6 120.3(5) . . ?
C7 C6 C5 119.4(5) . . ?
C6 C7 C8 120.7(5) . . ?
C7 C8 C3 120.3(5) . . ?
C14 C9 C10 120.8(5) . . ?
C14 C9 N1 121.3(5) . . ?
C10 C9 N1 117.9(5) . . ?
C11 C10 C9 118.9(5) . . ?
C12 C11 C10 120.3(5) . . ?
C11 C12 C13 120.3(5) . . ?
C11 C12 I1 119.0(4) . . ?
C13 C12 I1 120.7(4) . . ?
C14 C13 C12 120.0(5) . . ?
C20 C15 C16 121.4(5) . . ?
C20 C15 N4 119.8(5) . . ?
C16 C15 N4 118.7(5) . . ?
C15 C16 C17 118.7(6) . . ?
C18 C17 C16 119.8(5) . . ?
C17 C18 C19 121.3(5) . . ?
C17 C18 I2 118.2(4) . . ?
C19 C18 I2 120.5(4) . . ?
C18 C19 C20 118.8(5) . . ?
C15 C20 C19 120.0(5) . . ?
N2 N1 C1 124.6(4) . . ?
N2 N1 C9 115.4(4) . . ?
C1 N1 C9 119.6(4) . . ?
C2 N2 N1 115.8(4) . . ?
C2 N3 N4 114.6(4) . . ?
N3 N4 C1 125.9(4) . . ?
N3 N4 C15 115.7(4) . . ?
C1 N4 C15 118.3(4) . . ?

_refine_diff_density_max         1.194
_refine_diff_density_min         -0.814
_refine_diff_density_rms         0.132

####################################################################### 
# 
# 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_VJK004
_database_code_depnum_ccdc_archive 'CCDC 2109619'
loop_
_audit_author_name
_audit_author_address
'Stephen A. Moggach'
;University of Western Australia
Australia
;
_audit_update_record             
;
2021-09-14 deposited with the CCDC.	2021-12-16 downloaded from the CCDC.
;
_audit_creation_date             2021-09-06
_audit_creation_method           'CRYSTALS_ver_14.61_build_7809 '
_chemical_formula_moiety         'C20 H16 I2 N4 O1'
# Given Formula = C20 H16 I2 N4 O1 
# Dc =      1.95 Fooo =   1112.00 Mu =    250.92 M =    582.18
# Found Formula = C20 H16 I2 N4 O1 
# Dc =      1.95 FOOO =   1112.00 Mu =    250.92 M =    582.18
_chemical_formula_sum            'C20 H16 I2 N4 O1'
_chemical_formula_weight         582.18
_chemical_compound_source        .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
I -0.3257 6.8362 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
# end of ARCHIVE-HKL.CIF 
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   8.6930(5)
_cell_length_b                   12.8412(7)
_cell_length_c                   18.8190(8)
_cell_angle_alpha                74.349(4)
_cell_angle_beta                 82.296(4)
_cell_angle_gamma                79.321(5)
_cell_volume                     1979.95(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7002
_cell_measurement_temperature    100
_cell_measurement_theta_max      44.80
_cell_measurement_theta_min      3.78
_exptl_absorpt_coefficient_mu    25.092
_exptl_absorpt_correction_T_max  0.38
_exptl_absorpt_correction_T_min  0.13
# Sheldrick geometric approximatio 0.33 0.38 
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
 Gaussian Integration (Busing and Levy, 1957) 
;
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.953
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
# Non-dispersive F(000): 
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.181
_exptl_crystal_size_mid          0.044
_exptl_crystal_size_min          0.039
_diffrn_reflns_av_R_equivalents  0.158
_diffrn_reflns_av_unetI/netI     0.089
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            31524
_diffrn_reflns_theta_full        44.123
_diffrn_reflns_theta_max         45.024
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3153 
# Theoretical number of reflections is about 6408 
_diffrn_reflns_theta_min         2.448
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_standards_decay_%        .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                2536
_reflns_number_total             3153
# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(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_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         1.91
_refine_diff_density_min         -1.31
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9921
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         3153
_refine_ls_number_restraints     504
_refine_ls_R_factor_all          0.1187
_refine_ls_R_factor_gt           0.1055
_refine_ls_shift/su_max          0.0001725
_refine_ls_shift/su_mean         0.0000085
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.13P)² +84.74P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
#undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2812
_refine_ls_wR_factor_gt          0.2719
_refine_ls_wR_factor_ref         0.2812
_refine_special_details          
;The crystal was poorly scattering, the reflections were broad and a 4-component
twin.  Integration as a twin produced poor results, with the best 
solution obtained applying those post-data reduction using ROTAX using 
the refinemnt program CRYSTALS.

Comments on the checkcif output are given below. 

023_ALERT_3_A Resolution (too) Low [sin(theta)/Lambda < 0.6]..       0.46 Ang-1
027_ALERT_3_A _diffrn_reflns_theta_full value (too) Low ......      44.12 Degree
088_ALERT_3_B Poor Data / Parameter Ratio ....................       6.45 Note
342_ALERT_3_B Low Bond Precision on  C-C Bonds ...............    0.04026 Ang.
020_ALERT_3_C The Value of Rint is Greater Than 0.12 .........      0.158 Report
082_ALERT_2_C High R1 Value ..................................       0.11 Report
084_ALERT_3_C High wR2 Value (i.e. > 0.25) ...................       0.28 Report
#===============================================================================

Data were only integrated to 1 Angstrom, as the reflections were very broad.
Giving rise to these alerts.

241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of       C160 Check
334_ALERT_2_C Small Aver. Benzene C-C Dist C9       -C14             1.37 Ang.
334_ALERT_2_C Small Aver. Benzene C-C Dist C90      -C140            1.36 Ang.
906_ALERT_3_C Large K Value in the Analysis of Variance ......      8.855 Check
906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.379 Check
911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.459         32 Report

Vibrational and thermal similarity restraints were applied, as the data were 
poor and of low resolution.

923_ALERT_1_B S    Values in the CIF and FCF Differ by .......      0.989 Check

Reflections close to the beamstop were removed with a Sqrt(W) range of 0.0000001

#===============================================================================
003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         54 Report
072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.13 Report
083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large      84.74 Why ?
720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         16 Note
722_ALERT_1_G Angle   Calc      121.00, Rep      119.80 Dev...       1.20 Degree
              C90     -C140    -H1401      1_555  1_555  1_555     #   97 Check
760_ALERT_1_G CIF Contains no Torsion Angles .................          ? Info
769_ALERT_4_G CIF Embedded explicitly supplied scattering data     Please Note
793_ALERT_4_G Model has Chirality at C2          (Centro SPGR)          S Verify
860_ALERT_3_G Number of Least-Squares Restraints .............        504 Note
870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed ..          ! Info
909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        63% Note
992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by          4 Check
#===============================================================================

No action taken.,Twin
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: I2(0.0692) I200(0.0754) I1(0.0753) I100(0.0879) O1(0.0607)
 O100(0.0597) N1(0.058) N4(0.0604) C9(0.057) C800(0.0506) N300(0.0607)
 N400(0.0572) N100(0.0586) C120(0.0705) C300(0.0514) C400(0.0564) N3(0.0595)
 N200(0.0612) C12(0.0529) C180(0.0548) C18(0.0599) C700(0.0594) N2(0.0666)
 C100(0.0577) C90(0.0624) C5(0.0584) C1(0.0539) C2(0.0715) C8(0.0592)
 C7(0.0562) C190(0.0584) C130(0.0667) C4(0.0587) C3(0.059) C600(0.0603)
 C6(0.0558) C19(0.0641) C10(0.0568) C200(0.062) C140(0.0639) C150(0.0527)
 C14(0.0612) C170(0.0605) C13(0.0679) C17(0.0582) C11(0.0667) C15(0.0585)
 C16(0.0535) C500(0.0635) C1a(0.0611) C1b(0.0609) C20(0.0671) C110(0.0731)
 C160(0.0731) H800(0.0617) H400(0.0672) H700(0.0707) H51(0.0691) H100(0.0845)
 H81(0.0706) H71(0.0672) H190(0.0712) H130(0.0799) H41(0.0694) H600(0.0728)
 H61(0.0676) H191(0.0782) H200(0.0743) H140(0.0775) H141(0.0727) H170(0.0731)
 H131(0.0815) H171(0.0711) H101(0.0793) H161(0.0651) H500(0.0759) H111(0.0731)
 H201(0.082) H110(0.0865) H160(0.0867) H1(0.0705) H21(0.0705) H300(0.0733)
 H2(0.0738) H31(0.0712) H22(0.0794)
 Fixed X: H800(0.6519) H400(0.7521) H700(0.8061) H51(1.3324) H100(0.5259)
 H81(1.2309) H71(1.3983) H190(0.243) H130(0.3855) H41(1.1532) H600(0.9291)
 H61(1.4199) H191(0.9262) H200(0.4064) H140(0.4617) H141(0.9183) H170(0.1836)
 H131(0.743) H171(0.9105) H101(0.8254) H161(0.971) H500(0.9112) H111(0.6657)
 H201(1.0111) H110(0.4482) H160(0.3193) H1(0.4813) H21(0.9781) H300(0.6388)
 H2(0.7196) H31(1.2237) H22(1.1307)
 Fixed Y: H800(0.5943) H400(0.3342) H700(0.6889) H51(0.0764) H100(0.0302) H81(-
 0.1027) H71(-0.1907) H190(0.4308) H130(0.0483) H41(0.1626) H600(0.6165) H61(-
 0.1155) H191(0.0524) H200(0.3161) H140(0.1954) H141(0.4716) H170(0.6725)
 H131(0.6297) H171(-0.1837) H101(0.3115) H161(-0.0667) H500(0.4306)
 H111(0.4608) H201(0.1717) H110(-0.1266) H160(0.556) H1(0.4092) H21(0.0881)
 H300(0.4798) H2(0.2459) H31(0.0167) H22(0.2524)
 Fixed Z: H800(0.5777) H400(0.4872) H700(0.4842) H51(1.0968) H100(0.7654)
 H81(0.9248) H71(1.0214) H190(0.9477) H130(0.5352) H41(1.0108) H600(0.3821)
 H61(1.1163) H191(0.561) H200(0.8742) H140(0.5591) H141(0.7238) H170(0.7606)
 H131(0.7494) H171(0.7515) H101(0.9351) H161(0.8151) H500(0.3942) H111(0.9601)
 H201(0.6222) H110(0.7436) H160(0.6904) H1(0.5904) H21(0.9077) H300(0.6784)
 H2(0.5923) H31(0.8227) H22(0.9042)
;
#heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
I2 I 0.8520(3) -0.18162(16) 0.59531(11) 0.0692 1.0000 Uani . U . . . .
I200 I 0.0388(3) 0.66145(18) 0.91588(12) 0.0754 1.0000 Uani . U . . . .
I1 I 0.5480(3) 0.69440(17) 0.88492(12) 0.0753 1.0000 Uani . U . . . .
I100 I 0.3449(3) -0.18522(18) 0.60668(14) 0.0879 1.0000 Uani . U . . . .
O1 O 0.876(2) 0.2768(14) 0.7175(10) 0.0607 1.0000 Uani . U . . . .
O100 O 0.382(2) 0.2152(15) 0.7815(10) 0.0597 1.0000 Uani . U . . . .
N1 N 0.991(3) 0.2789(19) 0.8167(12) 0.0580 1.0000 Uani . U . . . .
N4 N 1.044(3) 0.1249(18) 0.7660(12) 0.0604 1.0000 Uani . U . . . .
C9 C 0.884(4) 0.375(2) 0.8302(15) 0.0570 1.0000 Uani . U . . . .
C800 C 0.705(3) 0.560(2) 0.5399(15) 0.0506 1.0000 Uani . U . . . .
N300 N 0.589(3) 0.4280(18) 0.6738(13) 0.0607 1.0000 Uani . U . . . .
N400 N 0.493(3) 0.3676(18) 0.7327(12) 0.0572 1.0000 Uani . U . . . .
N100 N 0.546(3) 0.2168(18) 0.6784(12) 0.0586 1.0000 Uani . U . . . .
C120 C 0.409(4) -0.054(2) 0.6373(18) 0.0705 1.0000 Uani . U . . . .
C300 C 0.690(3) 0.455(2) 0.5434(15) 0.0514 1.0000 Uani . U . . . .
C400 C 0.764(4) 0.407(2) 0.4863(16) 0.0564 1.0000 Uani . U . . . .
N3 N 1.141(3) 0.0680(18) 0.8264(12) 0.0595 1.0000 Uani . U . . . .
N200 N 0.640(3) 0.2770(18) 0.6183(12) 0.0612 1.0000 Uani . U . . . .
C12 C 0.691(3) 0.557(2) 0.8567(15) 0.0529 1.0000 Uani . U . . . .
C180 C 0.187(4) 0.561(2) 0.8580(15) 0.0548 1.0000 Uani . U . . . .
C18 C 0.915(4) -0.078(2) 0.6506(14) 0.0599 1.0000 Uani . U . . . .
C700 C 0.795(4) 0.617(2) 0.4836(16) 0.0594 1.0000 Uani . U . . . .
N2 N 1.084(3) 0.2207(19) 0.8787(13) 0.0666 1.0000 Uani . U . . . .
C1001 C 0.461(4) 0.269(2) 0.7335(16) 0.0577 1.0000 Uani . U . . . .
C90 C 0.496(4) 0.125(2) 0.6640(16) 0.0624 1.0000 Uani . U . . . .
C5 C 1.306(3) 0.037(2) 1.0651(16) 0.0584 1.0000 Uani . U . . . .
C1 C 0.965(4) 0.230(2) 0.7643(16) 0.0539 1.0000 Uani . U . . . .
C100 C 0.497(4) 0.034(2) 0.7178(16) 0.0715 1.0000 Uani . U . . . .
C8 C 1.250(4) -0.065(2) 0.9592(16) 0.0592 1.0000 Uani . U . . . .
C7 C 1.346(3) -0.118(2) 1.0202(16) 0.0562 1.0000 Uani . U . . . .
C190 C 0.261(4) 0.457(2) 0.8955(15) 0.0584 1.0000 Uani . U . . . .
C130 C 0.415(4) 0.044(2) 0.5831(17) 0.0667 1.0000 Uani . U . . . .
C4 C 1.208(4) 0.091(2) 1.0106(15) 0.0587 1.0000 Uani . U . . . .
C2 C 1.087(4) 0.104(2) 0.8924(16) 0.0590 1.0000 Uani . U . . . .
C600 C 0.872(4) 0.575(2) 0.4230(16) 0.0603 1.0000 Uani . U . . . .
C6 C 1.368(3) -0.074(2) 1.0744(16) 0.0558 1.0000 Uani . U . . . .
C19 C 0.943(4) 0.028(2) 0.6123(15) 0.0641 1.0000 Uani . U . . . .
C3 C 1.188(3) 0.044(2) 0.9536(16) 0.0568 1.0000 Uani . U . . . .
C200 C 0.363(4) 0.390(2) 0.8527(16) 0.0620 1.0000 Uani . U . . . .
C140 C 0.458(4) 0.130(2) 0.5971(16) 0.0639 1.0000 Uani . U . . . .
C150 C 0.392(3) 0.435(2) 0.7786(15) 0.0527 1.0000 Uani . U . . . .
C14 C 0.865(4) 0.469(2) 0.7717(15) 0.0612 1.0000 Uani . U . . . .
C170 C 0.223(4) 0.599(2) 0.7842(16) 0.0605 1.0000 Uani . U . . . .
C13 C 0.762(4) 0.564(2) 0.7875(17) 0.0679 1.0000 Uani . U . . . .
C17 C 0.929(4) -0.113(2) 0.7254(15) 0.0582 1.0000 Uani . U . . . .
C10 C 0.810(4) 0.377(2) 0.8962(17) 0.0667 1.0000 Uani . U . . . .
C2001 C 0.591(4) 0.393(2) 0.6048(16) 0.0585 1.0000 Uani . U . . . .
C16 C 0.967(4) -0.044(2) 0.7628(14) 0.0535 1.0000 Uani . U . . . .
C500 C 0.856(4) 0.466(2) 0.4302(17) 0.0635 1.0000 Uani . U . . . .
C15 C 1.001(4) 0.053(2) 0.7261(16) 0.0611 1.0000 Uani . U . . . .
C11 C 0.715(4) 0.464(2) 0.9113(16) 0.0609 1.0000 Uani . U . . . .
C20 C 0.989(4) 0.100(2) 0.6475(16) 0.0671 1.0000 Uani . U . . . .
C110 C 0.449(4) -0.061(2) 0.7055(18) 0.0731 1.0000 Uani . U . . . .
C160 C 0.312(4) 0.534(2) 0.7433(16) 0.0731 1.0000 Uani . U . . . .
H8001 H 0.6519 0.5943 0.5777 0.0617 1.0000 Uiso . . . . . .
H4001 H 0.7521 0.3342 0.4872 0.0672 1.0000 Uiso . . . . . .
H7001 H 0.8061 0.6889 0.4842 0.0707 1.0000 Uiso . . . . . .
H51 H 1.3324 0.0764 1.0968 0.0691 1.0000 Uiso . . . . . .
H1001 H 0.5259 0.0302 0.7654 0.0845 1.0000 Uiso . . . . . .
H81 H 1.2309 -0.1027 0.9248 0.0706 1.0000 Uiso . . . . . .
H71 H 1.3983 -0.1907 1.0214 0.0672 1.0000 Uiso . . . . . .
H1901 H 0.2430 0.4308 0.9477 0.0712 1.0000 Uiso . . . . . .
H1301 H 0.3855 0.0483 0.5352 0.0799 1.0000 Uiso . . . . . .
H41 H 1.1532 0.1626 1.0108 0.0694 1.0000 Uiso . . . . . .
H6001 H 0.9291 0.6165 0.3821 0.0728 1.0000 Uiso . . . . . .
H61 H 1.4199 -0.1155 1.1163 0.0676 1.0000 Uiso . . . . . .
H191 H 0.9262 0.0524 0.5610 0.0782 1.0000 Uiso . . . . . .
H2001 H 0.4064 0.3161 0.8742 0.0743 1.0000 Uiso . . . . . .
H1401 H 0.4617 0.1954 0.5591 0.0775 1.0000 Uiso . . . . . .
H141 H 0.9183 0.4716 0.7238 0.0727 1.0000 Uiso . . . . . .
H1701 H 0.1836 0.6725 0.7606 0.0731 1.0000 Uiso . . . . . .
H131 H 0.7430 0.6297 0.7494 0.0815 1.0000 Uiso . . . . . .
H171 H 0.9105 -0.1837 0.7515 0.0711 1.0000 Uiso . . . . . .
H101 H 0.8254 0.3115 0.9351 0.0793 1.0000 Uiso . . . . . .
H161 H 0.9710 -0.0667 0.8151 0.0651 1.0000 Uiso . . . . . .
H5001 H 0.9112 0.4306 0.3942 0.0759 1.0000 Uiso . . . . . .
H111 H 0.6657 0.4608 0.9601 0.0731 1.0000 Uiso . . . . . .
H201 H 1.0111 0.1717 0.6222 0.0820 1.0000 Uiso . . . . . .
H1101 H 0.4482 -0.1266 0.7436 0.0865 1.0000 Uiso . . . . . .
H1601 H 0.3193 0.5560 0.6904 0.0867 1.0000 Uiso . . . . . .
H20011 H 0.4813 0.4092 0.5904 0.0705 1.0000 Uiso . . . . . .
H21 H 0.9781 0.0881 0.9077 0.0705 1.0000 Uiso . . . . . .
H3001 H 0.6388 0.4798 0.6784 0.0733 1.0000 Uiso . . . . . .
H2002 H 0.7196 0.2459 0.5923 0.0738 1.0000 Uiso . . . . . .
H31 H 1.2237 0.0167 0.8227 0.0712 1.0000 Uiso . . . . . .
H22 H 1.1307 0.2524 0.9042 0.0794 1.0000 Uiso . . . . . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I2 . C18 . 2.08(3) yes
I200 . C180 . 2.07(3) yes
I1 . C12 . 2.11(3) yes
I100 . C120 . 2.11(3) yes
O1 . C1 . 1.21(3) yes
O100 . C1001 . 1.20(3) yes
N1 . C9 . 1.46(4) yes
N1 . N2 . 1.46(3) yes
N1 . C1 . 1.37(3) yes
N4 . N3 . 1.45(3) yes
N4 . C1 . 1.39(3) yes
N4 . C15 . 1.46(4) yes
C9 . C14 . 1.40(4) yes
C9 . C10 . 1.32(4) yes
C800 . C300 . 1.37(4) yes
C800 . C700 . 1.36(4) yes
C800 . H8001 . 0.955 no
N300 . N400 . 1.43(3) yes
N300 . C2001 . 1.48(4) yes
N300 . H3001 . 0.889 no
N400 . C1001 . 1.34(3) yes
N400 . C150 . 1.48(3) yes
N100 . N200 . 1.43(3) yes
N100 . C1001 . 1.43(4) yes
N100 . C90 . 1.43(4) yes
C120 . C130 . 1.39(4) yes
C120 . C110 . 1.35(4) yes
C300 . C400 . 1.41(4) yes
C300 . C2001 . 1.48(4) yes
C400 . C500 . 1.38(4) yes
C400 . H4001 . 0.950 no
N3 . C2 . 1.43(4) yes
N3 . H31 . 0.889 no
N200 . C2001 . 1.44(3) yes
N200 . H2002 . 0.891 no
C12 . C13 . 1.35(4) yes
C12 . C11 . 1.35(4) yes
C180 . C190 . 1.41(4) yes
C180 . C170 . 1.35(4) yes
C18 . C19 . 1.40(4) yes
C18 . C17 . 1.37(4) yes
C700 . C600 . 1.42(4) yes
C700 . H7001 . 0.951 no
N2 . C2 . 1.45(4) yes
N2 . H22 . 0.883 no
C90 . C100 . 1.32(4) yes
C90 . C140 . 1.32(4) yes
C5 . C4 . 1.37(4) yes
C5 . C6 . 1.40(4) yes
C5 . H51 . 0.950 no
C100 . C110 . 1.44(4) yes
C100 . H1001 . 0.950 no
C8 . C7 . 1.45(4) yes
C8 . C3 . 1.39(4) yes
C8 . H81 . 0.949 no
C7 . C6 . 1.34(4) yes
C7 . H71 . 0.953 no
C190 . C200 . 1.44(4) yes
C190 . H1901 . 0.950 no
C130 . C140 . 1.33(4) yes
C130 . H1301 . 0.953 no
C4 . C3 . 1.41(4) yes
C4 . H41 . 0.952 no
C2 . C3 . 1.50(4) yes
C2 . H21 . 0.991 no
C600 . C500 . 1.39(4) yes
C600 . H6001 . 0.948 no
C6 . H61 . 0.945 no
C19 . C20 . 1.41(4) yes
C19 . H191 . 0.954 no
C200 . C150 . 1.37(4) yes
C200 . H2001 . 0.950 no
C140 . H1401 . 0.947 no
C150 . C160 . 1.37(4) yes
C14 . C13 . 1.45(4) yes
C14 . H141 . 0.950 no
C170 . C160 . 1.36(4) yes
C170 . H1701 . 0.950 no
C13 . H131 . 0.949 no
C17 . C16 . 1.38(4) yes
C17 . H171 . 0.944 no
C10 . C11 . 1.34(4) yes
C10 . H101 . 0.952 no
C2001 . H20011 . 0.992 no
C16 . C15 . 1.31(4) yes
C16 . H161 . 0.952 no
C500 . H5001 . 0.949 no
C15 . C20 . 1.45(4) yes
C11 . H111 . 0.952 no
C20 . H201 . 0.952 no
C110 . H1101 . 0.950 no
C160 . H1601 . 0.955 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 . N1 . N2 . 113(2) yes
C9 . N1 . C1 . 121(2) yes
N2 . N1 . C1 . 122(2) yes
N3 . N4 . C1 . 119(2) yes
N3 . N4 . C15 . 114.1(20) yes
C1 . N4 . C15 . 124(2) yes
N1 . C9 . C14 . 118(2) yes
N1 . C9 . C10 . 122(3) yes
C14 . C9 . C10 . 120(3) yes
C300 . C800 . C700 . 120(3) yes
C300 . C800 . H8001 . 119.8 no
C700 . C800 . H8001 . 119.7 no
N400 . N300 . C2001 . 111(2) yes
N400 . N300 . H3001 . 124.1 no
C2001 . N300 . H3001 . 124.9 no
N300 . N400 . C1001 . 123(2) yes
N300 . N400 . C150 . 114(2) yes
C1001 . N400 . C150 . 121(2) yes
N200 . N100 . C1001 . 120(2) yes
N200 . N100 . C90 . 115(2) yes
C1001 . N100 . C90 . 121(2) yes
I100 . C120 . C130 . 118(2) yes
I100 . C120 . C110 . 124(2) yes
C130 . C120 . C110 . 119(3) yes
C800 . C300 . C400 . 119(3) yes
C800 . C300 . C2001 . 120(3) yes
C400 . C300 . C2001 . 120(3) yes
C300 . C400 . C500 . 118(3) yes
C300 . C400 . H4001 . 120.3 no
C500 . C400 . H4001 . 121.4 no
N4 . N3 . C2 . 112(2) yes
N4 . N3 . H31 . 123.9 no
C2 . N3 . H31 . 124.0 no
N100 . N200 . C2001 . 112(2) yes
N100 . N200 . H2002 . 123.8 no
C2001 . N200 . H2002 . 123.7 no
I1 . C12 . C13 . 121(2) yes
I1 . C12 . C11 . 117(2) yes
C13 . C12 . C11 . 122(3) yes
I200 . C180 . C190 . 121(2) yes
I200 . C180 . C170 . 119(2) yes
C190 . C180 . C170 . 120(3) yes
I2 . C18 . C19 . 120.9(20) yes
I2 . C18 . C17 . 120(2) yes
C19 . C18 . C17 . 119(3) yes
C800 . C700 . C600 . 124(3) yes
C800 . C700 . H7001 . 118.0 no
C600 . C700 . H7001 . 118.4 no
N1 . N2 . C2 . 110(2) yes
N1 . N2 . H22 . 124.8 no
C2 . N2 . H22 . 125.2 no
N400 . C1001 . O100 . 125(3) yes
N100 . C1001 . O100 . 117(3) yes
N100 . C1001 . N400 . 117(3) yes
N100 . C90 . C100 . 118(3) yes
N100 . C90 . C140 . 120(3) yes
C100 . C90 . C140 . 121(3) yes
C4 . C5 . C6 . 121(3) yes
C4 . C5 . H51 . 119.3 no
C6 . C5 . H51 . 119.5 no
N1 . C1 . O1 . 121(3) yes
N4 . C1 . O1 . 121(3) yes
N4 . C1 . N1 . 118(3) yes
C90 . C100 . C110 . 120(3) yes
C90 . C100 . H1001 . 121.0 no
C110 . C100 . H1001 . 118.8 no
C7 . C8 . C3 . 116(3) yes
C7 . C8 . H81 . 122.4 no
C3 . C8 . H81 . 121.8 no
C8 . C7 . C6 . 126(3) yes
C8 . C7 . H71 . 116.3 no
C6 . C7 . H71 . 118.0 no
C180 . C190 . C200 . 119(2) yes
C180 . C190 . H1901 . 120.8 no
C200 . C190 . H1901 . 120.6 no
C120 . C130 . C140 . 122(3) yes
C120 . C130 . H1301 . 118.3 no
C140 . C130 . H1301 . 120.1 no
C5 . C4 . C3 . 121(3) yes
C5 . C4 . H41 . 119.2 no
C3 . C4 . H41 . 119.3 no
N3 . C2 . C3 . 111(2) yes
N3 . C2 . H21 . 108.2 no
N2 . C2 . N3 . 111(2) yes
N2 . C2 . C3 . 110(2) yes
N2 . C2 . H21 . 108.3 no
C3 . C2 . H21 . 108.9 no
C700 . C600 . C500 . 113(3) yes
C700 . C600 . H6001 . 123.3 no
C500 . C600 . H6001 . 123.4 no
C5 . C6 . C7 . 116(3) yes
C5 . C6 . H61 . 122.5 no
C7 . C6 . H61 . 121.8 no
C18 . C19 . C20 . 123(3) yes
C18 . C19 . H191 . 117.9 no
C20 . C19 . H191 . 119.4 no
C4 . C3 . C8 . 119(3) yes
C2 . C3 . C8 . 119(3) yes
C2 . C3 . C4 . 122(3) yes
C190 . C200 . C150 . 117(2) yes
C190 . C200 . H2001 . 122.1 no
C150 . C200 . H2001 . 120.7 no
C90 . C140 . H1401 . 119.9 no
C130 . C140 . C90 . 120(3) yes
C130 . C140 . H1401 . 119.8 no
N400 . C150 . C200 . 119(2) yes
N400 . C150 . C160 . 118(2) yes
C200 . C150 . C160 . 122(3) yes
C9 . C14 . C13 . 117(3) yes
C9 . C14 . H141 . 122.0 no
C13 . C14 . H141 . 121.3 no
C180 . C170 . C160 . 121(3) yes
C180 . C170 . H1701 . 119.3 no
C160 . C170 . H1701 . 119.3 no
C12 . C13 . H131 . 121.2 no
C14 . C13 . C12 . 119(3) yes
C14 . C13 . H131 . 119.9 no
C18 . C17 . C16 . 120(3) yes
C18 . C17 . H171 . 120.0 no
C16 . C17 . H171 . 119.8 no
C9 . C10 . C11 . 124(3) yes
C9 . C10 . H101 . 118.1 no
C11 . C10 . H101 . 118.3 no
N300 . C2001 . C300 . 112(2) yes
N300 . C2001 . N200 . 110(2) yes
N300 . C2001 . H20011 . 107.8 no
C300 . C2001 . N200 . 112(2) yes
C300 . C2001 . H20011 . 108.3 no
N200 . C2001 . H20011 . 107.3 no
C17 . C16 . C15 . 120(3) yes
C17 . C16 . H161 . 120.3 no
C15 . C16 . H161 . 119.8 no
C400 . C500 . H5001 . 117.1 no
C600 . C500 . C400 . 125(3) yes
C600 . C500 . H5001 . 118.4 no
N4 . C15 . C16 . 120(2) yes
N4 . C15 . C20 . 115(2) yes
C16 . C15 . C20 . 125(3) yes
C12 . C11 . C10 . 119(3) yes
C12 . C11 . H111 . 120.9 no
C10 . C11 . H111 . 120.0 no
C19 . C20 . H201 . 123.7 no
C15 . C20 . C19 . 112(2) yes
C15 . C20 . H201 . 123.9 no
C120 . C110 . H1101 . 121.1 no
C100 . C110 . C120 . 118(3) yes
C100 . C110 . H1101 . 121.2 no
C150 . C160 . C170 . 119(3) yes
C150 . C160 . H1601 . 120.1 no
C170 . C160 . H1601 . 120.7 no

# looking for ARCHIVE-HKL.CIF 
_oxford_diffrn_Wilson_B_factor   5.91
_oxford_diffrn_Wilson_scale      81.71
_oxford_refine_ls_R_factor_all   0.1187
_oxford_refine_ls_R_factor_ref   0.1187
_oxford_refine_ls_scale          0.1350(3)
_oxford_refine_ls_wR_factor_all  0.2812
# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 
# Explicitly named reflections are ALWAYS excluded from R&wR 
# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
# Computed with I/sigma = -10 
_oxford_reflns_number_all        3153
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.562(11) 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000 1.0000
2 0.342(11) 1.0000 0.0000 0.0000 0.5470 -1.0000 0.0000 0.5800 0.0000 -1.0000
3 0.096(10) -1.0000 -0.0060 0.0060 0.0000 -0.4870 -0.5130 0.0000 -1.4870 0.4870

# start Validation Reply Form
_vrf_THETM01_VJK004              
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The crystal was poorly scattering, the reflections were broad 
and a 4-component twin.  Integration as a twin produced poor results, with the best 
solution obtained applying those post-data reduction using ROTAX using 
the refinemnt program CRYSTALS.
Data were only integrated to 1 Angstrom, as the reflections were very broad.
Giving rise to these alerts.
;
_vrf_PLAT027_VJK004              
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      44.12 Degree
RESPONSE: The crystal was poorly scattering, the reflections were broad 
and a 4-component twin.  Integration as a twin produced poor results, with the best 
solution obtained applying those post-data reduction using ROTAX using 
the refinemnt program CRYSTALS.
Data were only integrated to 1 Angstrom, as the reflections were very broad.
Giving rise to these alerts.
;
_vrf_PLAT088_VJK004              
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.45 Note  
RESPONSE: The crystal was poorly scattering, the reflections were broad 
and a 4-component twin.  Integration as a twin produced poor results, with the best 
solution obtained applying those post-data reduction using ROTAX using 
the refinemnt program CRYSTALS.
Data were only integrated to 1 Angstrom, as the reflections were very broad.
Giving rise to these alerts.
;
_vrf_PLAT342_VJK004              
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.04026 Ang.  
RESPONSE: The crystal was poorly scattering, the reflections were broad 
and a 4-component twin.  Integration as a twin produced poor results, with the best 
solution obtained applying those post-data reduction using ROTAX using 
the refinemnt program CRYSTALS.
Data were only integrated to 1 Angstrom, as the reflections were very broad.
Giving rise to these alerts.
;
_vrf_PLAT923_VJK004              
;
PROBLEM: S    Values in the CIF and FCF Differ by .......      0.992 Check 
RESPONSE: The crystal was poorly scattering, the reflections were broad 
and a 4-component twin.  Integration as a twin produced poor results, with the best 
solution obtained applying those post-data reduction using ROTAX using 
the refinemnt program CRYSTALS.
Data were only integrated to 1 Angstrom, as the reflections were very broad.
Giving rise to these alerts.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_vjk2032
_database_code_depnum_ccdc_archive 'CCDC 2109617'
loop_
_audit_author_name
_audit_author_address
'Stephen A. Moggach'
;University of Western Australia
Australia
;
_audit_update_record             
;
2021-09-14 deposited with the CCDC.	2021-12-16 downloaded from the CCDC.
;
_audit_creation_date             2021-08-29
_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         'C22 H22 N4 O'
_chemical_formula_sum            'C22 H22 N4 O'
_chemical_formula_weight         358.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N4 O1 C20 H20'
_chemical_oxdiff_usercomment     'Varshinil for Low'
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           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.1113(2)
_cell_length_b                   22.2891(9)
_cell_length_c                   8.3663(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.156(5)
_cell_angle_gamma                90
_cell_volume                     919.99(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4426
_cell_measurement_temperature    99.8(6)
_cell_measurement_theta_max      74.8310
_cell_measurement_theta_min      3.9610
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70626
_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            'clear light colourless'
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             380
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -13 -1 0.0332
0 -14 1 0.0282
0 9 -4 0.0295
-1 9 -4 0.0209
0 -9 4 0.0212
0 6 -5 0.0272
0 1 -5 0.0209
-3 -3 2 0.1083
0 -1 5 0.0210
0 -4 -5 0.0209
0 4 5 0.0209
0 -8 -4 0.0266
0 -8 -4 0.0229
0 8 4 0.0209
-1 14 1 0.0266
1 -14 -1 0.0500
3 3 -2 0.0817
0 -14 1 0.0291
0 -9 4 0.0210
-1 -8 -4 0.0253

_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.042
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.7421 -13.3415 -1.3332 -0.3953 0.8305 0.3925
-0.3638 -13.9116 1.4813 -0.8299 0.4514 0.3278
0.2054 9.3918 -4.0669 0.9603 0.1257 -0.2489
-0.6484 8.8727 -3.7373 0.9915 0.1300 0.0090
0.0604 -9.2980 3.9935 -0.9771 -0.1280 0.1700
0.1938 5.5922 -4.9114 0.8845 0.4212 -0.2007
-0.2938 0.7214 -5.0905 0.7257 0.6880 0.0090
-3.2314 -3.1060 1.7836 -0.0071 -0.0056 1.0000
0.0001 -0.9997 5.2311 -0.7233 -0.6857 0.0815
-0.0680 -3.6759 -5.0393 0.4776 0.8785 0.0090
0.0680 3.6759 5.0393 -0.4776 -0.8785 -0.0090
0.1617 -7.7161 -4.4933 0.1827 0.9831 0.0090
-0.1075 -7.9409 -4.3299 0.1819 0.9790 0.0921
-0.1617 7.7161 4.4933 -0.1827 -0.9831 -0.0090
-0.6598 14.1392 0.6273 0.6880 -0.7257 -0.0090
1.1449 -13.5246 -0.8858 -0.6808 0.7183 -0.1431
3.2409 2.9614 -1.7333 -0.0076 0.0050 -1.0000
0.0585 -13.9953 1.3029 -0.8600 0.4673 0.2050
0.2941 -9.1634 3.9078 -0.9866 -0.1295 0.0995
-0.5124 -8.1719 -4.0277 0.1786 0.9599 0.2160

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13294
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.328
_diffrn_reflns_theta_min         3.967
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.8(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  26.00   0.50    0.42    --   45.95 -19.00  60.00  108
  2  ω    -28.00  26.00   0.50    0.42    --   45.95 -19.00   0.00  108
  3  ω    -25.00  61.00   0.50    0.42    --   45.95 -57.00 -60.00  172
  4  ω     30.00 108.00   0.50    1.80    --  102.41-110.00 -91.00  156
  5  ω     73.00 107.00   0.50    1.80    --  102.41-125.00-180.00   68
  6  ω     30.00  68.00   0.50    1.80    --  102.41-125.00-180.00   76
  7  ω     31.00  70.00   0.50    1.80    --  102.41 -61.00-180.00   78
  8  ω     33.00 121.00   0.50    0.42    --   45.95  19.00-120.00  176
  9  ω     86.00 175.00   0.50    1.80    --  102.41  61.00 -30.00  178
 10  ω    102.00 129.00   0.50    1.80    --  102.41 110.00   4.00   54
 11  ω     90.00 177.00   0.50    1.80    --  102.41  30.00  60.00  174
 12  ω     30.00 111.00   0.50    1.80    --  102.41-125.00   0.00  162
 13  ω     30.00 105.00   0.50    1.80    --  102.41 -77.00 150.00  150
 14  ω     30.00 105.00   0.50    1.80    --  102.41 -94.00  30.00  150
 15  ω      2.00  86.00   0.50    0.42    --   45.95-110.00 -91.00  168
 16  ω    -28.00  26.00   0.50    0.42    --   45.95 -19.00-120.00  108
 17  ω    -86.00  -1.00   0.50    0.42    --  -45.95 110.00   4.00  170
 18  ω   -119.00 -73.00   0.50    0.42    --  -45.95-125.00  30.00   92
 19  ω   -175.00 -82.00   0.50    1.80    -- -102.41-110.00 -91.00  186
 20  ω   -175.00 -89.00   0.50    1.80    -- -102.41 -50.00-176.79  172
 21  ω    -71.00 -30.00   0.50    1.80    -- -102.41  61.00 -30.00   82
 22  ω    -71.00 -30.00   0.50    1.80    -- -102.41  61.00  30.00   82
 23  ω    -71.00 -30.00   0.50    1.80    -- -102.41  61.00  90.00   82
 24  ω   -108.00 -30.00   0.50    1.80    -- -102.41 110.00   4.00  156
 25  ω   -111.00 -30.00   0.50    1.80    -- -102.41 125.00-120.00  162
 26  ω    -71.00 -30.00   0.50    1.80    -- -102.41  61.00-180.00   82
 27  ω   -108.00 -30.00   0.50    1.80    -- -102.41 108.00 -45.17  156
 28  ω   -105.00 -30.00   0.50    1.80    -- -102.41  77.00 120.00  150
 29  ω   -111.00 -30.00   0.50    1.80    -- -102.41 125.00 150.00  162
 30  ω   -175.00 -86.00   0.50    1.80    -- -102.41 -62.00  22.02  178
 31  ω   -177.00 -89.00   0.50    1.80    -- -102.41 -15.00  60.00  176
 32  ω   -175.00 -80.00   0.50    1.80    -- -102.41 -76.00 137.78  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1160213000
_diffrn_orient_matrix_UB_12      0.0489625000
_diffrn_orient_matrix_UB_13      -0.1289198000
_diffrn_orient_matrix_UB_21      -0.0307714000
_diffrn_orient_matrix_UB_22      -0.0465497000
_diffrn_orient_matrix_UB_23      -0.1399697000
_diffrn_orient_matrix_UB_31      -0.2883031000
_diffrn_orient_matrix_UB_32      -0.0146617000
_diffrn_orient_matrix_UB_33      0.0127882000
_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                1615
_reflns_number_total             1927
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0042(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1927
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0509
_refine_ls_restrained_S_all      1.112
_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)+(0.0927P)²+0.2236P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1585
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O1 O -0.0024(3) 0.250000 0.18887(19) 0.0247(4) Uani 1 2 d S T P . .
N1 N 0.3888(2) 0.30297(5) 0.28316(16) 0.0225(3) Uani 1 1 d . . . . .
N2 N 0.6566(2) 0.30437(6) 0.39190(17) 0.0237(4) Uani 1 1 d . . . . .
C1 C 0.2462(4) 0.250000 0.2480(3) 0.0221(5) Uani 1 2 d S T P . .
C2 C 0.6962(4) 0.250000 0.4922(3) 0.0229(5) Uani 1 2 d S T P . .
C3 C 0.9739(4) 0.250000 0.6153(3) 0.0247(5) Uani 1 2 d S T P . .
C4 C 1.0985(3) 0.30362(7) 0.6767(2) 0.0312(4) Uani 1 1 d . . . . .
H4 H 1.019738 0.339845 0.634383 0.037 Uiso 1 1 calc R . . . .
C5 C 1.3407(3) 0.30366(8) 0.8011(2) 0.0350(5) Uani 1 1 d . . . . .
H5 H 1.421536 0.339865 0.841922 0.042 Uiso 1 1 calc R . . . .
C6 C 1.4616(4) 0.250000 0.8644(3) 0.0325(6) Uani 1 2 d S T P . .
H6 H 1.622109 0.250000 0.948395 0.039 Uiso 1 2 calc RS T P . .
C7 C 0.2482(3) 0.35912(7) 0.26141(19) 0.0239(4) Uani 1 1 d . . . . .
C8 C 0.3192(3) 0.40389(7) 0.3806(2) 0.0273(4) Uani 1 1 d . . . . .
H8 H 0.461846 0.397845 0.474219 0.033 Uiso 1 1 calc R . . . .
C9 C 0.1767(3) 0.45772(7) 0.3597(2) 0.0291(4) Uani 1 1 d . . . . .
H9 H 0.227590 0.487498 0.439674 0.035 Uiso 1 1 calc R . . . .
C10 C -0.0399(3) 0.46819(7) 0.2223(2) 0.0295(4) Uani 1 1 d . . . . .
C11 C -0.1016(3) 0.42354(8) 0.1018(2) 0.0304(4) Uani 1 1 d . . . . .
H11 H -0.242418 0.429809 0.007312 0.036 Uiso 1 1 calc R . . . .
C12 C 0.0408(3) 0.37015(7) 0.1187(2) 0.0274(4) Uani 1 1 d . . . . .
H12 H -0.001602 0.341566 0.034860 0.033 Uiso 1 1 calc R . . . .
C13 C -0.2041(3) 0.52511(8) 0.2036(2) 0.0363(4) Uani 1 1 d . . . . .
H13A H -0.371173 0.517509 0.232229 0.054 Uiso 1 1 calc GR . . . .
H13B H -0.242559 0.538717 0.091011 0.054 Uiso 1 1 calc GR . . . .
H13C H -0.103360 0.555362 0.275747 0.054 Uiso 1 1 calc GR . . . .
H2A H 0.551(6) 0.250000 0.553(4) 0.044 Uiso 1 2 d RS T P . .
H2 H 0.772(5) 0.3038(10) 0.327(3) 0.044 Uiso 1 1 d 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
O1 C1 1.237(2) . ?
N1 N2 1.4322(16) . ?
N1 C1 1.3782(15) . ?
N1 C7 1.4309(18) . ?
N2 C2 1.4575(17) . ?
N2 H2 0.90(2) . ?
C2 C3 1.520(3) . ?
C2 H2A 1.00(3) . ?
C3 C4 1.3882(19) . ?
C3 C4 1.3882(19) 4_565 ?
C4 H4 0.9300 . ?
C4 C5 1.394(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.390(2) . ?
C7 C12 1.396(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.390(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(2) . ?
C10 C11 1.393(2) . ?
C10 C13 1.507(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(2) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C1 N1 N2 121.23(12) . . ?
C1 N1 C7 120.14(12) . . ?
C7 N1 N2 115.25(11) . . ?
N1 N2 C2 108.26(12) . . ?
N1 N2 H2 106.7(15) . . ?
C2 N2 H2 108.6(14) . . ?
O1 C1 N1 121.06(8) . 4_565 ?
O1 C1 N1 121.06(8) . . ?
N1 C1 N1 117.87(17) . 4_565 ?
N2 C2 N2 112.48(18) 4_565 . ?
N2 C2 C3 110.77(11) . . ?
N2 C2 C3 110.77(11) 4_565 . ?
N2 C2 H2A 106.3(9) . . ?
N2 C2 H2A 106.3(9) 4_565 . ?
C3 C2 H2A 110.0(18) . . ?
C4 C3 C2 120.51(10) 4_565 . ?
C4 C3 C2 120.51(10) . . ?
C4 C3 C4 118.8(2) 4_565 . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.60(15) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.34(16) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C5 119.2(2) 4_565 . ?
C5 C6 H6 120.4 . . ?
C5 C6 H6 120.4 4_565 . ?
C8 C7 N1 120.56(13) . . ?
C8 C7 C12 118.99(14) . . ?
C12 C7 N1 120.44(14) . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.96(14) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 119.1 . . ?
C8 C9 C10 121.73(15) . . ?
C10 C9 H9 119.1 . . ?
C9 C10 C11 117.30(14) . . ?
C9 C10 C13 121.90(16) . . ?
C11 C10 C13 120.79(15) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.83(14) . . ?
C12 C11 H11 119.1 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 120.04(15) . . ?
C11 C12 H12 120.0 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C2 N2 57.7(2) . . . 4_565 ?
N1 N2 C2 C3 -177.78(13) . . . . ?
N1 C7 C8 C9 -178.51(13) . . . . ?
N1 C7 C12 C11 177.29(13) . . . . ?
N2 N1 C1 O1 162.26(17) . . . . ?
N2 N1 C1 N1 -16.8(3) . . . 4_565 ?
N2 N1 C7 C8 -23.36(19) . . . . ?
N2 N1 C7 C12 155.47(14) . . . . ?
N2 C2 C3 C4 -29.4(3) 4_565 . . 4_565 ?
N2 C2 C3 C4 154.98(18) 4_565 . . . ?
N2 C2 C3 C4 -154.98(18) . . . 4_565 ?
N2 C2 C3 C4 29.4(3) . . . . ?
C1 N1 N2 C2 -19.4(2) . . . . ?
C1 N1 C7 C8 136.15(17) . . . . ?
C1 N1 C7 C12 -45.0(2) . . . . ?
C2 C3 C4 C5 173.84(18) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C3 C4 C5 -1.8(3) 4_565 . . . ?
C4 C5 C6 C5 0.8(4) . . . 4_565 ?
C7 N1 N2 C2 139.82(14) . . . . ?
C7 N1 C1 O1 4.0(3) . . . . ?
C7 N1 C1 N1 -175.05(12) . . . 4_565 ?
C7 C8 C9 C10 0.8(2) . . . . ?
C8 C7 C12 C11 -3.9(2) . . . . ?
C8 C9 C10 C11 -2.9(2) . . . . ?
C8 C9 C10 C13 176.68(15) . . . . ?
C9 C10 C11 C12 1.6(2) . . . . ?
C10 C11 C12 C7 1.7(2) . . . . ?
C12 C7 C8 C9 2.7(2) . . . . ?
C13 C10 C11 C12 -177.93(15) . . . . ?

_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
;

####################################################################### 
# 
# 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_vjk2024
_database_code_depnum_ccdc_archive 'CCDC 2109621'
loop_
_audit_author_name
_audit_author_address
'Stephen A. Moggach'
;University of Western Australia
Australia
;
_audit_update_record             
;
2021-09-14 deposited with the CCDC.	2021-12-16 downloaded from the CCDC.
;
_audit_creation_date             2021-08-29
_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         'C22 H19 N4 O S2'
_chemical_formula_sum            'C22 H19 N4 O S2'
_chemical_formula_weight         419.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         'S2 N4 O1 C50 H40'
_chemical_oxdiff_usercomment     'Varshini for Low'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.2557(2)
_cell_length_b                   24.1715(7)
_cell_length_c                   11.2028(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.330(2)
_cell_angle_gamma                90
_cell_volume                     1961.44(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14224
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      74.4930
_cell_measurement_theta_min      3.6620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.636
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63460
_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            'clear light green'
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             876
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -2 1 0.2327
0 -7 -7 0.0665
1 10 5 0.0726
0 -11 -5 0.0667
1 13 4 0.0727
0 -15 -1 0.0585
-1 -15 1 0.0718
2 15 -1 0.0767
2 13 -3 0.0788
0 -11 5 0.0644
-5 -2 1 0.1944
0 -7 6 0.0682
1 2 -7 0.0730
1 2 7 0.0717
1 -2 -7 0.0703
0 -2 -7 0.0750
-1 3 7 0.0860
0 11 5 0.0747
0 -11 -5 0.0663
0 14 3 0.0732
-3 12 2 0.0995
1 15 1 0.0733
0 -16 -1 0.0604
-3 13 0 0.1027
-1 15 1 0.0800
0 -15 1 0.0583
0 -14 3 0.0604
-3 11 -3 0.1030
-1 14 -3 0.0788
0 -11 5 0.0616
1 11 -5 0.0764
0 -7 6 0.0665
-2 7 -6 0.0906

_exptl_crystal_size_max          0.434
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.138
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.5426 -2.3799 1.1571 0.0024 0.0087 -1.0000
0.0550 -6.8365 -6.5351 -0.1817 -0.9770 0.1113
1.3170 9.6207 5.2328 -0.1224 0.9356 -0.3311
-0.3075 -10.7123 -5.2500 0.1291 -0.9854 0.1113
1.4336 12.6569 3.5347 -0.4131 0.8678 -0.2763
-0.1837 -15.4767 -1.1414 0.6858 -0.7233 -0.0803
-0.6950 -15.3692 1.0541 0.8780 -0.4772 -0.0368
1.5948 14.6869 -0.8205 -0.8667 0.4713 -0.1635
1.5938 13.3939 -3.0198 -0.9770 0.1817 -0.1121
-0.3106 -11.1327 5.1207 0.9728 0.1277 -0.1932
-4.6283 -2.4795 1.1551 0.4260 0.0551 0.9030
-0.3862 -7.2421 6.4461 0.8883 0.4233 -0.1779
0.9335 2.3823 -7.1147 -0.7252 -0.6876 0.0361
0.5349 1.7066 7.1144 0.4553 0.8380 -0.3009
0.7027 -2.4605 -7.1507 -0.4772 -0.8780 0.0376
-0.2395 -1.8999 -7.1700 -0.4636 -0.8532 0.2393
-1.3920 2.8149 6.9412 0.4745 0.8727 0.1151
0.2837 10.7333 5.2463 -0.1294 0.9859 -0.1061
0.3011 -11.1040 -5.1341 0.1300 -0.9913 -0.0222
0.2254 13.8482 3.3710 -0.4301 0.9028 -0.0090
-2.6748 12.3910 1.9619 -0.3371 0.7088 0.6197
1.2758 14.7392 1.3933 -0.6791 0.7162 -0.1610
0.2164 -15.5215 -1.0346 0.6782 -0.7156 -0.1669
-2.7951 12.6419 0.1162 -0.4905 0.5182 0.7007
-1.2955 15.0409 0.7014 -0.6316 0.6666 0.3959
0.1026 -15.4621 1.2190 0.8593 -0.4673 -0.2081
0.1585 -13.9060 3.3394 0.9477 -0.1763 -0.2660
-2.5492 11.2357 -2.9687 -0.6766 0.1263 0.7254
-0.8814 13.5353 -3.3316 -0.8957 0.1668 0.4122
0.1481 -11.1122 5.1050 0.9496 0.1243 -0.2878
1.2532 10.8466 -4.9923 -0.9915 -0.1300 -0.0090
0.4669 -7.3391 6.3296 0.8450 0.4022 -0.3525
-1.7349 7.0153 -5.7527 -0.7252 -0.3449 0.5959

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1463
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            36258
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.311
_diffrn_reflns_theta_min         3.657
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(4)
_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 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -33.00   0.50    0.09    --  -46.20 166.00 152.00  174
  2  ω   -118.00 -47.00   0.50    0.09    --  -46.20-166.00 131.00  142
  3  ω    -89.00  -6.00   0.50    0.09    --  -46.20 116.00   6.00  166
  4  ω     34.00 120.00   0.50    0.09    --   46.20-166.00 131.00  172
  5  ω     47.00 118.00   0.50    0.09    --   46.20 166.00 152.00  142
  6  ω      7.00  89.00   0.50    0.09    --   46.20-116.00 -82.00  164
  7  ω   -139.00 -33.00   0.50    0.26    -- -102.41 166.00 152.00  212
  8  ω   -108.00 -30.00   0.50    0.26    -- -102.41 116.00   6.00  156
  9  ω   -175.00 -79.00   0.50    0.26    -- -102.41-116.00 -82.00  192
 10  ω     79.00 175.00   0.50    0.26    --  102.41 116.00   6.00  192
 11  ω     30.00 109.00   0.50    0.26    --  102.41-116.00 -82.00  158
 12  ω     34.00 140.00   0.50    0.26    --  102.41-166.00 131.00  212
 13  ω   -118.00 -73.00   0.50    0.09    --  -46.20-125.00 -60.00   90
 14  ω    -26.00  29.00   0.50    0.09    --  -46.20  19.00   0.00  110
 15  ω   -118.00 -73.00   0.50    0.09    --  -46.20-125.00 -30.00   90
 16  ω   -118.00 -73.00   0.50    0.09    --  -46.20-125.00 150.00   90
 17  ω   -118.00 -73.00   0.50    0.09    --  -46.20-125.00 120.00   90
 18  ω    -28.00  26.00   0.50    0.09    --   46.20 -19.00  90.00  108
 19  ω    -28.00  26.00   0.50    0.09    --   46.20 -19.00 -30.00  108
 20  ω    -28.00  26.00   0.50    0.09    --   46.20 -19.00-120.00  108
 21  ω    -71.00 -30.00   0.50    0.26    -- -102.41  61.00  30.00   82
 22  ω    -71.00 -30.00   0.50    0.26    -- -102.41  61.00   0.00   82
 23  ω    -71.00 -30.00   0.50    0.26    -- -102.41  61.00-180.00   82
 24  ω    -71.00 -30.00   0.50    0.26    -- -102.41  61.00 -30.00   82
 25  ω   -175.00 -84.00   0.50    0.26    -- -102.41 -66.00 -62.51  182
 26  ω   -111.00 -30.00   0.50    0.26    -- -102.41 125.00-120.00  162
 27  ω   -177.00 -90.00   0.50    0.26    -- -102.41 -30.00-180.00  174
 28  ω   -177.00 -90.00   0.50    0.26    -- -102.41 -30.00-120.00  174
 29  ω   -105.00 -30.00   0.50    0.26    -- -102.41  77.00   0.00  150
 30  ω   -153.00 -47.00   0.50    0.26    -- -102.41-166.00 131.00  212
 31  ω   -175.00 -91.00   0.50    0.26    -- -102.41 -61.00   0.00  168
 32  ω    -70.00 -30.00   0.50    0.26    -- -102.41  61.00-120.00   80
 33  ω   -172.00-117.00   0.50    0.26    -- -102.41 -64.00-158.96  110
 34  ω     72.00 108.00   0.50    0.26    --  102.41-111.00 170.27   72
 35  ω     30.00  57.00   0.50    0.26    --  102.41-111.00 170.27   54
 36  ω     69.00 105.00   0.50    0.26    --  102.41 -94.00  30.00   72
 37  ω     90.00 172.00   0.50    0.26    --  102.41  45.00  90.00  164
 38  ω     91.00 168.00   0.50    0.26    --  102.41  61.00 -30.00  154
 39  ω     30.00 101.00   0.50    0.26    --  102.41 -94.00  90.00  142
 40  ω     31.00  95.00   0.50    0.26    --  102.41-125.00-150.00  128
 41  ω     77.00 105.00   0.50    0.26    --  102.41 -77.00 -60.00   56
 42  ω    117.00 143.00   0.50    0.26    --  102.41  45.00 120.00   52
 43  ω     76.00 101.00   0.50    0.26    --  102.41 166.00 152.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0456654000
_diffrn_orient_matrix_UB_12      -0.0496215000
_diffrn_orient_matrix_UB_13      0.0793258000
_diffrn_orient_matrix_UB_21      -0.0055038000
_diffrn_orient_matrix_UB_22      0.0387702000
_diffrn_orient_matrix_UB_23      0.1089011000
_diffrn_orient_matrix_UB_31      -0.2076033000
_diffrn_orient_matrix_UB_32      0.0097922000
_diffrn_orient_matrix_UB_33      -0.0290296000
_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                3477
_reflns_number_total             3996
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.699
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3996
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0589
_refine_ls_restrained_S_all      1.074
_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)+(0.1158P)²+0.9246P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1612
_refine_ls_wR_factor_ref         0.1758
_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:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C16(H16), C17(H17), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.31044(8) 0.24991(3) 1.01268(6) 0.0305(2) Uani 1 1 d . . . . .
S2 S 0.20062(7) 0.79071(2) 0.89136(5) 0.0238(2) Uani 1 1 d . . . . .
O1 O 0.2819(2) 0.51972(7) 0.90335(15) 0.0267(4) Uani 1 1 d . . . . .
N1 N 0.2918(3) 0.46290(8) 0.73999(17) 0.0211(4) Uani 1 1 d . . . . .
N2 N 0.2825(3) 0.45545(8) 0.61831(17) 0.0222(4) Uani 1 1 d . . . . .
N3 N 0.2296(3) 0.55204(8) 0.59346(17) 0.0214(4) Uani 1 1 d . . . . .
N4 N 0.2361(3) 0.55732(8) 0.71584(17) 0.0201(4) Uani 1 1 d . . . . .
C1 C 0.2710(3) 0.51364(10) 0.7951(2) 0.0204(5) Uani 1 1 d . . . . .
C2 C 0.2530(3) 0.50105(9) 0.5540(2) 0.0199(5) Uani 1 1 d . . . . .
C3 C 0.2455(3) 0.49367(10) 0.4221(2) 0.0203(5) Uani 1 1 d . . . . .
C4 C 0.3073(3) 0.44477(10) 0.3726(2) 0.0235(5) Uani 1 1 d . . . . .
H4 H 0.354520 0.416652 0.422123 0.028 Uiso 1 1 calc R . . . .
C5 C 0.2986(3) 0.43784(11) 0.2487(2) 0.0259(5) Uani 1 1 d . . . . .
H5 H 0.339421 0.404980 0.216057 0.031 Uiso 1 1 calc R . . . .
C6 C 0.2294(3) 0.47969(11) 0.1739(2) 0.0253(5) Uani 1 1 d . . . . .
H6 H 0.223728 0.474995 0.091389 0.030 Uiso 1 1 calc R . . . .
C7 C 0.1688(3) 0.52853(11) 0.2234(2) 0.0258(5) Uani 1 1 d . . . . .
H7 H 0.124252 0.556905 0.173635 0.031 Uiso 1 1 calc R . . . .
C8 C 0.1741(3) 0.53546(10) 0.3466(2) 0.0233(5) Uani 1 1 d . . . . .
H8 H 0.129948 0.567979 0.378911 0.028 Uiso 1 1 calc R . . . .
C9 C 0.2964(3) 0.41260(10) 0.8076(2) 0.0211(5) Uani 1 1 d . . . . .
C10 C 0.1915(3) 0.36840(10) 0.7632(2) 0.0222(5) Uani 1 1 d . . . . .
H10 H 0.118936 0.372680 0.692557 0.027 Uiso 1 1 calc R . . . .
C11 C 0.1930(3) 0.31792(10) 0.8222(2) 0.0235(5) Uani 1 1 d . . . . .
H11 H 0.123007 0.288535 0.790833 0.028 Uiso 1 1 calc R . . . .
C12 C 0.3003(3) 0.31148(10) 0.9292(2) 0.0228(5) Uani 1 1 d . . . . .
C13 C 0.4066(3) 0.35622(10) 0.9731(2) 0.0229(5) Uani 1 1 d . . . . .
H13 H 0.479148 0.352080 1.043775 0.027 Uiso 1 1 calc R . . . .
C14 C 0.4063(3) 0.40648(10) 0.9137(2) 0.0231(5) Uani 1 1 d . . . . .
H14 H 0.478063 0.435738 0.943909 0.028 Uiso 1 1 calc R . . . .
C15 C 0.2264(3) 0.61320(10) 0.7578(2) 0.0214(5) Uani 1 1 d . . . . .
C16 C 0.3113(3) 0.65437(9) 0.6947(2) 0.0219(5) Uani 1 1 d . . . . .
H16 H 0.372705 0.645252 0.626836 0.026 Uiso 1 1 calc R . . . .
C17 C 0.3054(3) 0.70928(10) 0.7320(2) 0.0220(5) Uani 1 1 d . . . . .
H17 H 0.362303 0.736663 0.688863 0.026 Uiso 1 1 calc R . . . .
C18 C 0.2145(3) 0.72315(10) 0.8338(2) 0.0214(5) Uani 1 1 d . . . . .
C19 C 0.1262(3) 0.68132(10) 0.8958(2) 0.0232(5) Uani 1 1 d . . . . .
H19 H 0.062781 0.690322 0.962930 0.028 Uiso 1 1 calc R . . . .
C20 C 0.1321(3) 0.62678(10) 0.8583(2) 0.0227(5) Uani 1 1 d . . . . .
H20 H 0.073180 0.599360 0.900161 0.027 Uiso 1 1 calc R . . . .
C21 C 0.1862(4) 0.20141(11) 0.9166(3) 0.0352(6) Uani 1 1 d . . . . .
H21A H 0.241951 0.199737 0.840993 0.053 Uiso 1 1 calc GR . . . .
H21B H 0.060121 0.213144 0.904318 0.053 Uiso 1 1 calc GR . . . .
H21C H 0.190229 0.165462 0.953041 0.053 Uiso 1 1 calc GR . . . .
C22 C 0.3471(4) 0.82960(11) 0.7985(3) 0.0332(6) Uani 1 1 d . . . . .
H22A H 0.287704 0.833569 0.720093 0.050 Uiso 1 1 calc GR . . . .
H22B H 0.462217 0.810494 0.792776 0.050 Uiso 1 1 calc GR . . . .
H22C H 0.369542 0.865516 0.832857 0.050 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 C12 1.757(2) . ?
S1 C21 1.798(3) . ?
S2 C18 1.761(2) . ?
S2 C22 1.795(3) . ?
O1 C1 1.220(3) . ?
N1 N2 1.373(3) . ?
N1 C1 1.385(3) . ?
N1 C9 1.432(3) . ?
N2 C2 1.327(3) . ?
N3 N4 1.375(3) . ?
N3 C2 1.324(3) . ?
N4 C1 1.393(3) . ?
N4 C15 1.433(3) . ?
C2 C3 1.486(3) . ?
C3 C4 1.391(3) . ?
C3 C8 1.398(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.396(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.387(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.387(3) . ?
C9 C14 1.401(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.388(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.400(3) . ?
C12 C13 1.401(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.385(3) . ?
C15 C20 1.391(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.393(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.392(3) . ?
C18 C19 1.402(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.385(3) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
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
C12 S1 C21 103.27(13) . . ?
C18 S2 C22 103.00(12) . . ?
N2 N1 C1 123.93(19) . . ?
N2 N1 C9 114.35(18) . . ?
C1 N1 C9 121.06(19) . . ?
C2 N2 N1 115.30(19) . . ?
C2 N3 N4 114.97(19) . . ?
N3 N4 C1 124.01(19) . . ?
N3 N4 C15 114.52(18) . . ?
C1 N4 C15 121.05(19) . . ?
O1 C1 N1 123.2(2) . . ?
O1 C1 N4 122.8(2) . . ?
N1 C1 N4 114.05(19) . . ?
N2 C2 C3 115.8(2) . . ?
N3 C2 N2 127.7(2) . . ?
N3 C2 C3 116.5(2) . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 C8 119.3(2) . . ?
C8 C3 C2 120.4(2) . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.1(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.4(2) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C3 C8 H8 119.9 . . ?
C7 C8 C3 120.2(2) . . ?
C7 C8 H8 119.9 . . ?
C10 C9 N1 118.0(2) . . ?
C10 C9 C14 119.8(2) . . ?
C14 C9 N1 122.2(2) . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.1(2) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.6(2) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 S1 123.64(19) . . ?
C11 C12 C13 118.8(2) . . ?
C13 C12 S1 117.52(18) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 C12 121.5(2) . . ?
C14 C13 H13 119.2 . . ?
C9 C14 H14 120.5 . . ?
C13 C14 C9 119.0(2) . . ?
C13 C14 H14 120.5 . . ?
C16 C15 N4 118.5(2) . . ?
C16 C15 C20 119.9(2) . . ?
C20 C15 N4 121.6(2) . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.6(2) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.0(2) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 S2 124.29(18) . . ?
C17 C18 C19 119.0(2) . . ?
C19 C18 S2 116.74(18) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.9(2) . . ?
C20 C19 H19 119.6 . . ?
C15 C20 H20 120.2 . . ?
C19 C20 C15 119.7(2) . . ?
C19 C20 H20 120.2 . . ?
S1 C21 H21A 109.5 . . ?
S1 C21 H21B 109.5 . . ?
S1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
S2 C22 H22A 109.5 . . ?
S2 C22 H22B 109.5 . . ?
S2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 C12 C13 C14 -179.56(17) . . . . ?
S2 C18 C19 C20 -178.98(17) . . . . ?
N1 N2 C2 N3 -0.9(3) . . . . ?
N1 N2 C2 C3 179.10(17) . . . . ?
N1 C9 C10 C11 178.3(2) . . . . ?
N1 C9 C14 C13 -178.7(2) . . . . ?
N2 N1 C1 O1 -179.0(2) . . . . ?
N2 N1 C1 N4 1.0(3) . . . . ?
N2 N1 C9 C10 -36.7(3) . . . . ?
N2 N1 C9 C14 141.4(2) . . . . ?
N2 C2 C3 C4 -14.0(3) . . . . ?
N2 C2 C3 C8 165.2(2) . . . . ?
N3 N4 C1 O1 177.6(2) . . . . ?
N3 N4 C1 N1 -2.5(3) . . . . ?
N3 N4 C15 C16 -35.6(3) . . . . ?
N3 N4 C15 C20 143.4(2) . . . . ?
N3 C2 C3 C4 166.0(2) . . . . ?
N3 C2 C3 C8 -14.8(3) . . . . ?
N4 N3 C2 N2 -0.4(3) . . . . ?
N4 N3 C2 C3 179.57(17) . . . . ?
N4 C15 C16 C17 179.95(19) . . . . ?
N4 C15 C20 C19 180.0(2) . . . . ?
C1 N1 N2 C2 0.6(3) . . . . ?
C1 N1 C9 C10 134.3(2) . . . . ?
C1 N1 C9 C14 -47.6(3) . . . . ?
C1 N4 C15 C16 137.3(2) . . . . ?
C1 N4 C15 C20 -43.7(3) . . . . ?
C2 N3 N4 C1 2.3(3) . . . . ?
C2 N3 N4 C15 174.94(18) . . . . ?
C2 C3 C4 C5 179.5(2) . . . . ?
C2 C3 C8 C7 179.5(2) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C3 C8 C7 -1.4(3) . . . . ?
C4 C5 C6 C7 0.0(4) . . . . ?
C5 C6 C7 C8 -1.1(4) . . . . ?
C6 C7 C8 C3 1.8(4) . . . . ?
C8 C3 C4 C5 0.3(3) . . . . ?
C9 N1 N2 C2 171.26(18) . . . . ?
C9 N1 C1 O1 10.9(3) . . . . ?
C9 N1 C1 N4 -169.09(19) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C10 C9 C14 C13 -0.6(3) . . . . ?
C10 C11 C12 S1 179.09(17) . . . . ?
C10 C11 C12 C13 -1.1(3) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C9 0.2(3) . . . . ?
C14 C9 C10 C11 0.1(3) . . . . ?
C15 N4 C1 O1 5.3(3) . . . . ?
C15 N4 C1 N1 -174.73(18) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C16 C15 C20 C19 -1.0(3) . . . . ?
C16 C17 C18 S2 178.92(17) . . . . ?
C16 C17 C18 C19 -1.5(3) . . . . ?
C17 C18 C19 C20 1.4(3) . . . . ?
C18 C19 C20 C15 -0.1(3) . . . . ?
C20 C15 C16 C17 1.0(3) . . . . ?
C21 S1 C12 C11 8.2(2) . . . . ?
C21 S1 C12 C13 -171.67(18) . . . . ?
C22 S2 C18 C17 -6.0(2) . . . . ?
C22 S2 C18 C19 174.37(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
;

