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

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

data_exp_218_auto
_database_code_depnum_ccdc_archive 'CCDC 2129908'
loop_
_audit_author_name
_audit_author_address
'Ahmed Alzamly'
;UAEU
United Arab Emirates
;
_audit_update_record             
;
2021-12-20 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_audit_creation_date             2021-12-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H5 Br N2 O'
_chemical_formula_sum            'C8 H5 Br N2 O'
_chemical_formula_weight         225.05
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C32  H20  Br4  N8  O4  '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.65259(19)
_cell_length_b                   9.7551(2)
_cell_length_c                   10.0315(3)
_cell_angle_alpha                82.229(2)
_cell_angle_beta                 85.282(2)
_cell_angle_gamma                79.1919(19)
_cell_volume                     822.66(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7063
_cell_measurement_temperature    297.00(10)
_cell_measurement_theta_max      76.7990
_cell_measurement_theta_min      4.4720
_shelx_estimated_absorpt_T_max   0.645
_shelx_estimated_absorpt_T_min   0.389
_exptl_absorpt_coefficient_mu    6.405
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.817
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -1 0.0294
0 1 1 0.0455
-1 -1 0 0.0392
1 1 0 0.0426
1 2 1 0.0477
-1 0 -1 0.0768
1 0 2 0.0602
-1 0 1 0.0566
1 0 -1 0.0449
1 1 2 0.0434
-2 -1 -1 0.0637
-1 2 1 0.0729
0 1 0 0.0828
-2 1 0 0.0794
-1 1 -1 0.0872
2 -1 0 0.0636

_exptl_crystal_size_max          0.182
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.075
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
-0.0005 -0.9992 -1.0002 0.0263 0.1673 -0.1244
0.0005 0.9992 1.0002 -0.0263 -0.1673 0.1244
-0.9999 -1.0015 -0.0001 0.0242 0.1833 0.1207
0.9999 1.0015 0.0001 -0.0242 -0.1833 -0.1207
1.0004 2.0007 1.0004 -0.0505 -0.3506 0.0037
-1.0013 -0.0019 -0.9997 0.2169 0.0753 0.0331
1.0022 0.0017 1.9996 -0.3264 -0.1049 0.0729
-0.9994 -0.0024 1.0001 -0.0020 0.0160 0.2451
0.9994 0.0024 -1.0001 0.0020 -0.0160 -0.2451
1.0018 1.0011 1.9999 -0.2432 -0.2426 0.0913
-2.0011 -1.0035 -0.9998 0.2411 0.2586 0.1538
-1.0003 1.9964 1.0008 0.1643 -0.2594 0.2819
-0.0005 0.9994 0.0003 0.0832 -0.1377 0.0184
-2.0011 0.9951 0.0008 0.2981 -0.0464 0.2966
-1.0017 0.9974 -0.9993 0.3001 -0.0624 0.0515
2.0011 -0.9951 -0.0008 -0.2981 0.0464 -0.2966

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14176
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.459
_diffrn_reflns_theta_min         4.456
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     45.00 122.00   0.50    0.05    --   49.76  19.00 -30.00  154
  2  ω     45.00 122.00   0.50    0.05    --   49.76  19.00 -60.00  154
  3  ω     45.00 122.00   0.50    0.05    --   49.76  19.00 -90.00  154
  4  ω     45.00 122.00   0.50    0.05    --   49.76  19.00-150.00  154
  5  ω     45.00 122.00   0.50    0.05    --   49.76  19.00  60.00  154
  6  ω      1.00  56.00   0.50    0.05    --   49.76   0.00  90.00  110
  7  ω     36.00 121.00   0.50    0.05    --   49.76  64.00  87.00  170
  8  ω    -64.00  22.00   0.50    0.05    --  -49.76  64.00  87.00  172
  9  ω    -76.00 -18.00   0.50    0.17    --  -90.00  64.00  87.00  116
 10  ω    -26.00  22.00   0.50    0.05    --  -49.76  19.00   0.00   96
 11  ω    -66.00 -18.00   0.50    0.17    --  -90.00  57.00 -90.00   96
 12  ω    -66.00 -18.00   0.50    0.17    --  -90.00  57.00-120.00   96
 13  ω     56.00 111.00   0.50    0.17    --  104.80   0.00 120.00  110
 14  ω    131.00 177.00   0.50    0.17    --  104.80  37.00 120.00   92
 15  ω     91.00 177.00   0.50    0.17    --  104.80  64.00  87.00  172
 16  ω    131.00 177.00   0.50    0.17    --  104.80  37.00-180.00   92
 17  ω     56.00 111.00   0.50    0.17    --  104.80   0.00 -60.00  110
 18  ω    131.00 177.00   0.50    0.17    --  104.80  37.00 -30.00   92
 19  ω    137.00 177.00   0.50    0.17    --  104.80  57.00 -60.00   80
 20  ω    113.00 177.00   0.50    0.17    --  104.80 125.00  30.00  128
 21  ω     33.00  66.00   0.50    0.17    --  104.80 -57.00  30.00   66
 22  ω     33.00  76.00   0.50    0.17    --  104.80 -64.00 -48.00   86
 23  ω    -21.00  64.00   0.50    0.05    --   49.76 -64.00 -48.00  170
 24  ω     33.00  66.00   0.50    0.17    --  104.80 -57.00  90.00   66
 25  ω     33.00  66.00   0.50    0.17    --  104.80 -57.00 150.00   66
 26  ω     33.00 106.00   0.50    0.17    --  104.80 -99.00 120.00  146
 27  ω     33.00 106.00   0.50    0.17    --  104.80 -99.00  60.00  146
 28  ω     33.00 106.00   0.50    0.17    --  104.80 -99.00   0.00  146
 29  ω     33.00 106.00   0.50    0.17    --  104.80 -99.00 -30.00  146
 30  ω     35.00 111.00   0.50    0.17    --  104.80-125.00 -60.00  152
 31  ω     33.00 106.00   0.50    0.17    --  104.80 -99.00-180.00  146
 32  ω     35.00  94.00   0.50    0.05    --   49.76-125.00-180.00  118
 33  ω   -120.00 -36.00   0.50    0.05    --  -49.76 -64.00 -48.00  168
 34  ω   -161.00-134.00   0.50    0.17    --  -90.00 -77.00 -90.00   54
 35  ω   -161.00-134.00   0.50    0.17    --  -90.00 -77.00 -60.00   54
 36  ω   -161.00-134.00   0.50    0.17    --  -90.00 -77.00   0.00   54
 37  ω   -161.00 -76.00   0.50    0.17    --  -90.00 -64.00 -48.00  170
 38  ω   -121.00 -45.00   0.50    0.05    --  -49.76 -19.00  60.00  152
 39  ω   -121.00 -45.00   0.50    0.05    --  -49.76 -21.00 141.26  152
 40  ω   -161.00-131.00   0.50    0.17    --  -90.00 -37.00  90.00   60
 41  ω   -161.00-126.00   0.50    0.17    --  -90.00 -99.00  90.00   70
 42  ω   -161.00-126.00   0.50    0.17    --  -90.00 -99.00-120.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1075989000
_diffrn_orient_matrix_UB_12      0.0832345000
_diffrn_orient_matrix_UB_13      -0.1093683000
_diffrn_orient_matrix_UB_21      -0.0453359000
_diffrn_orient_matrix_UB_22      -0.1377648000
_diffrn_orient_matrix_UB_23      -0.0296390000
_diffrn_orient_matrix_UB_31      -0.1390525000
_diffrn_orient_matrix_UB_32      0.0182962000
_diffrn_orient_matrix_UB_33      0.1061431000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2977
_reflns_number_total             3283
_reflns_odcompleteness_completeness 99.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.071
_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)+(0.0381P)²+0.3986P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0807
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C5(H5), C7(H7), C4(H4), C19(H19), C8(H8), C16(H16), C15(H15)
;
_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
Br11 Br 0.06144(3) 0.61880(3) 1.20384(3) 0.05332(11) Uani 1 1 d . . . . .
Br1 Br 1.14329(4) 0.12253(3) 0.09613(3) 0.05664(11) Uani 1 1 d . . . . .
O11 O 0.5706(2) 0.42628(19) 0.64520(19) 0.0536(4) Uani 1 1 d . . . . .
O1 O 0.6050(2) -0.07936(18) 0.62332(19) 0.0547(5) Uani 1 1 d . . . . .
N13 N 0.5277(3) 0.6435(2) 0.7185(2) 0.0443(5) Uani 1 1 d . . . . .
N2 N 0.6753(3) 0.1386(2) 0.5814(2) 0.0452(5) Uani 1 1 d . . . . .
C12 C 0.5936(3) 0.5468(3) 0.6386(3) 0.0442(5) Uani 1 1 d . . . . .
N1 N 0.4045(3) 0.1279(3) 0.8460(3) 0.0738(8) Uani 1 1 d . . . . .
C17 C 0.2091(3) 0.6213(3) 1.0522(3) 0.0423(5) Uani 1 1 d . . . . .
C14 C 0.4199(3) 0.6297(2) 0.8311(2) 0.0404(5) Uani 1 1 d . . . . .
C6 C 0.9971(3) 0.1234(3) 0.2486(3) 0.0444(5) Uani 1 1 d . . . . .
C3 C 0.7851(3) 0.1259(2) 0.4690(2) 0.0407(5) Uani 1 1 d . . . . .
N11 N 0.7917(4) 0.6332(3) 0.4492(3) 0.0724(8) Uani 1 1 d . . . . .
C2 C 0.5968(3) 0.0422(3) 0.6464(3) 0.0448(5) Uani 1 1 d . . . . .
C18 C 0.2413(3) 0.5105(3) 0.9778(3) 0.0494(6) Uani 1 1 d . . . . .
H18 H 0.192086 0.433082 1.002118 0.059 Uiso 1 1 calc R U . . .
C11 C 0.7038(3) 0.5995(3) 0.5327(3) 0.0517(6) Uani 1 1 d . . . . .
C1 C 0.4892(3) 0.0944(3) 0.7585(3) 0.0532(6) Uani 1 1 d . . . . .
C5 C 0.9667(3) 0.2381(3) 0.3184(3) 0.0532(6) Uani 1 1 d . . . . .
H5 H 1.017221 0.314301 0.291363 0.064 Uiso 1 1 calc R U . . .
C7 C 0.9245(3) 0.0089(3) 0.2889(3) 0.0505(6) Uani 1 1 d . . . . .
H7 H 0.946730 -0.068716 0.241414 0.061 Uiso 1 1 calc R U . . .
C4 C 0.8609(3) 0.2399(3) 0.4287(3) 0.0513(6) Uani 1 1 d . . . . .
H4 H 0.840044 0.317365 0.476443 0.062 Uiso 1 1 calc R U . . .
C19 C 0.3467(3) 0.5134(3) 0.8664(3) 0.0487(6) Uani 1 1 d . . . . .
H19 H 0.368508 0.438351 0.815528 0.058 Uiso 1 1 calc R U . . .
C8 C 0.8184(3) 0.0097(3) 0.4002(3) 0.0489(6) Uani 1 1 d . . . . .
H8 H 0.769947 -0.067632 0.428226 0.059 Uiso 1 1 calc R U . . .
C16 C 0.2812(3) 0.7372(3) 1.0187(3) 0.0524(6) Uani 1 1 d . . . . .
H16 H 0.258794 0.812018 1.069853 0.063 Uiso 1 1 calc R U . . .
C15 C 0.3868(3) 0.7402(3) 0.9082(3) 0.0510(6) Uani 1 1 d . . . . .
H15 H 0.436497 0.817522 0.885148 0.061 Uiso 1 1 calc R U . . .
H2 H 0.650(3) 0.214(3) 0.606(3) 0.047(8) Uiso 1 1 d . . . . .
H13 H 0.547(4) 0.715(4) 0.702(3) 0.060(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br11 C17 1.905(2) . ?
Br1 C6 1.903(3) . ?
O11 C12 1.220(3) . ?
O1 C2 1.227(3) . ?
N13 C12 1.337(3) . ?
N13 C14 1.413(3) . ?
N13 H13 0.74(4) . ?
N2 C3 1.416(3) . ?
N2 C2 1.331(3) . ?
N2 H2 0.79(3) . ?
C12 C11 1.474(4) . ?
N1 C1 1.139(4) . ?
C17 C18 1.369(4) . ?
C17 C16 1.381(3) . ?
C14 C19 1.392(3) . ?
C14 C15 1.384(3) . ?
C6 C5 1.372(4) . ?
C6 C7 1.381(4) . ?
C3 C4 1.393(3) . ?
C3 C8 1.379(3) . ?
N11 C11 1.141(4) . ?
C2 C1 1.481(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.384(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.377(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.385(4) . ?
C4 H4 0.9300 . ?
C19 H19 0.9300 . ?
C8 H8 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.378(4) . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N13 C14 128.5(2) . . ?
C12 N13 H13 118(3) . . ?
C14 N13 H13 114(3) . . ?
C3 N2 H2 117(2) . . ?
C2 N2 C3 128.3(2) . . ?
C2 N2 H2 114(2) . . ?
O11 C12 N13 127.3(2) . . ?
O11 C12 C11 120.0(2) . . ?
N13 C12 C11 112.8(2) . . ?
C18 C17 Br11 120.26(19) . . ?
C18 C17 C16 121.1(2) . . ?
C16 C17 Br11 118.69(19) . . ?
C19 C14 N13 123.7(2) . . ?
C15 C14 N13 116.7(2) . . ?
C15 C14 C19 119.6(2) . . ?
C5 C6 Br1 119.23(19) . . ?
C5 C6 C7 120.7(2) . . ?
C7 C6 Br1 120.04(19) . . ?
C4 C3 N2 116.1(2) . . ?
C8 C3 N2 123.9(2) . . ?
C8 C3 C4 120.0(2) . . ?
O1 C2 N2 127.6(2) . . ?
O1 C2 C1 119.3(2) . . ?
N2 C2 C1 113.2(2) . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
N11 C11 C12 176.3(3) . . ?
N1 C1 C2 176.5(3) . . ?
C6 C5 H5 120.2 . . ?
C6 C5 C4 119.7(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 119.9(2) . . ?
C8 C7 H7 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 120.0 . . ?
C14 C19 H19 120.3 . . ?
C18 C19 C14 119.4(2) . . ?
C18 C19 H19 120.3 . . ?
C3 C8 C7 119.5(2) . . ?
C3 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C17 C16 H16 120.5 . . ?
C15 C16 C17 118.9(2) . . ?
C15 C16 H16 120.5 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15 119.6 . . ?

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
Br11 C17 C18 C19 179.0(2) . . . . ?
Br11 C17 C16 C15 -179.3(2) . . . . ?
Br1 C6 C5 C4 179.9(2) . . . . ?
Br1 C6 C7 C8 179.8(2) . . . . ?
N13 C14 C19 C18 -179.2(2) . . . . ?
N13 C14 C15 C16 178.9(3) . . . . ?
N2 C3 C4 C5 -178.4(3) . . . . ?
N2 C3 C8 C7 178.1(3) . . . . ?
C12 N13 C14 C19 -9.4(4) . . . . ?
C12 N13 C14 C15 171.1(3) . . . . ?
C17 C18 C19 C14 0.2(4) . . . . ?
C17 C16 C15 C14 0.4(4) . . . . ?
C14 N13 C12 O11 1.8(5) . . . . ?
C14 N13 C12 C11 -178.6(2) . . . . ?
C6 C5 C4 C3 -0.1(5) . . . . ?
C6 C7 C8 C3 0.6(4) . . . . ?
C3 N2 C2 O1 1.1(5) . . . . ?
C3 N2 C2 C1 -179.0(2) . . . . ?
C2 N2 C3 C4 -174.2(3) . . . . ?
C2 N2 C3 C8 5.9(4) . . . . ?
C18 C17 C16 C15 0.1(4) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
C7 C6 C5 C4 -0.9(4) . . . . ?
C4 C3 C8 C7 -1.7(4) . . . . ?
C19 C14 C15 C16 -0.6(4) . . . . ?
C8 C3 C4 C5 1.4(4) . . . . ?
C16 C17 C18 C19 -0.4(4) . . . . ?
C15 C14 C19 C18 0.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   361
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.686
_oxdiff_exptl_absorpt_empirical_full_min 0.601
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_235_auto
_database_code_depnum_ccdc_archive 'CCDC 2131409'
_audit_update_record             
;
2021-12-28 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_audit_creation_date             2021-12-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
ahmed.alzamly@uaeu.ac.ae
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 N2 O2 S'
_chemical_formula_sum            'C10 H8 N2 O2 S'
_chemical_formula_weight         220.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   3.9979(2)
_cell_length_b                   15.5449(11)
_cell_length_c                   15.9729(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.509(4)
_cell_angle_gamma                90
_cell_volume                     992.63(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3863
_cell_measurement_temperature    297.00(10)
_cell_measurement_theta_max      76.6170
_cell_measurement_theta_min      5.4810
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.515
_exptl_absorpt_coefficient_mu    2.752
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 0 1 0.1353
-3 0 -1 0.1383
0 5 -1 0.0143
0 -5 1 0.0120
0 -1 -5 0.0234
0 1 5 0.0074
-2 7 -2 0.0960
2 -7 2 0.0960

_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.026
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
3.0001 -0.0162 1.0482 0.0972 0.0582 -1.1556
-3.0001 0.0162 -1.0482 -0.0972 -0.0582 1.1556
0.0002 5.0115 -1.0165 -0.2461 -0.4412 -0.0331
-0.0002 -5.0115 1.0165 0.2461 0.4412 0.0331
0.0030 -0.9943 -5.0135 0.4265 -0.2386 0.0687
-0.0030 0.9943 5.0135 -0.4265 0.2386 -0.0687
-1.9998 7.0268 -2.0551 -0.4141 -0.6523 0.7233
1.9998 -7.0268 2.0551 0.4141 0.6523 -0.7233

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7605
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.364
_diffrn_reflns_theta_min         5.540
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00 -25.00   0.50    1.39    --  -49.51 149.00  73.00  156
  2  ω    -84.00 -11.00   0.50    1.39    --  -49.51 123.00 -90.00  146
  3  ω   -120.00 -57.00   0.50    1.39    --  -49.51-149.00  26.00  126
  4  ω     47.00 109.00   0.50    1.39    --   49.51-149.00  26.00  124
  5  ω     33.00  93.00   0.50    1.39    --   49.51-123.00-170.00  120
  6  ω   -103.00 -25.00   0.50    5.54    --  -90.00 149.00  73.00  156
  7  ω   -161.00 -75.00   0.50    5.54    --  -90.00-123.00-170.00  172
  8  ω     33.00 110.00   0.50    5.54    --  104.80-123.00-170.00  154
  9  ω     47.00 129.00   0.50    5.54    --  104.80-149.00  26.00  164
 10  ω    122.00 158.00   0.50    5.54    --  104.80 149.00  73.00   72
 11  ω    -23.00  18.00   0.50    1.39    --  -49.51  19.00-150.00   82
 12  ω    -26.00  13.00   0.50    1.39    --  -49.51  19.00 120.00   78
 13  ω    -10.00  20.00   0.50    1.39    --  -49.51  19.00  60.00   60
 14  ω     -5.00  21.00   0.50    1.39    --   49.51 -19.00 120.00   52
 15  ω   -160.00-131.00   0.50    5.54    --  -90.00 -37.00-120.00   58
 16  ω   -160.00-131.00   0.50    5.54    --  -90.00 -37.00-180.00   58
 17  ω   -159.00-127.00   0.50    5.54    --  -90.00 -99.00 -30.00   64
 18  ω   -159.00-132.00   0.50    5.54    --  -90.00 -37.00 -90.00   54
 19  ω   -161.00-136.00   0.50    5.54    --  -90.00 -77.00  30.00   50
 20  ω   -160.00-133.00   0.50    5.54    --  -90.00 -37.00-150.00   54
 21  ω   -161.00-133.00   0.50    5.54    --  -90.00 -37.00 -60.00   56
 22  ω   -161.00-128.00   0.50    5.54    --  -90.00 -99.00 120.00   66
 23  ω     57.00 106.00   0.50    5.54    --  104.80 -99.00-120.00   98
 24  ω    115.00 175.00   0.50    5.54    --  104.80 125.00 -30.00  120
 25  ω     33.00  58.00   0.50    5.54    --  104.80 -57.00  60.00   50
 26  ω     38.00  63.00   0.50    5.54    --  104.80 -57.00 -30.00   50
 27  ω    137.00 162.00   0.50    5.54    --  104.80  57.00-180.00   50
 28  ω     38.00  63.00   0.50    5.54    --  104.80 -57.00 -90.00   50
 29  ω     37.00  65.00   0.50    5.54    --  104.80 -57.00-120.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0573435000
_diffrn_orient_matrix_UB_12      -0.0637842000
_diffrn_orient_matrix_UB_13      -0.0723861000
_diffrn_orient_matrix_UB_21      -0.0028702000
_diffrn_orient_matrix_UB_22      -0.0753605000
_diffrn_orient_matrix_UB_23      0.0625373000
_diffrn_orient_matrix_UB_31      -0.3810061000
_diffrn_orient_matrix_UB_32      -0.0090450000
_diffrn_orient_matrix_UB_33      -0.0121376000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1491
_reflns_number_total             1900
_reflns_odcompleteness_completeness 97.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.047
_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     138
_refine_ls_number_reflns         1900
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      1.063
_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)+(0.0752P)²+0.1720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1349
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S5 S 0.36317(15) 0.31238(4) 0.73209(4) 0.0566(2) Uani 1 1 d . . . . .
O10 O 0.4994(4) 0.30854(11) 0.36912(10) 0.0585(5) Uani 1 1 d . . . . .
O12 O 0.7434(5) 0.18078(11) 0.44660(11) 0.0598(5) Uani 1 1 d . . . . .
N7 N 0.1504(5) 0.43523(14) 0.63390(13) 0.0528(5) Uani 1 1 d . . . . .
C8 C 0.2953(5) 0.37396(15) 0.58331(14) 0.0478(5) Uani 1 1 d . . . . .
C1 C 0.4629(6) 0.31278(15) 0.45339(15) 0.0484(5) Uani 1 1 d . . . . .
C4 C 0.4284(6) 0.30241(16) 0.62571(15) 0.0491(5) Uani 1 1 d . . . . .
C2 C 0.6012(5) 0.24057(16) 0.49738(15) 0.0490(6) Uani 1 1 d . . . . .
C3 C 0.5815(5) 0.23457(16) 0.58277(15) 0.0504(6) Uani 1 1 d . . . . .
H3 H 0.666899 0.187119 0.611260 0.061 Uiso 1 1 calc R U . . .
C9 C 0.3124(6) 0.37900(15) 0.49589(15) 0.0493(5) Uani 1 1 d . . . . .
H9 H 0.224027 0.426027 0.467291 0.059 Uiso 1 1 calc R U . . .
C6 C 0.1722(6) 0.41041(17) 0.71171(15) 0.0534(6) Uani 1 1 d . . . . .
N15 N -0.0474(8) 0.50529(19) 0.83161(16) 0.0830(8) Uani 1 1 d . . . . .
C14 C 0.0490(7) 0.46266(19) 0.77919(17) 0.0626(7) Uani 1 1 d . . . . .
C11 C 0.3420(7) 0.37457(19) 0.32058(16) 0.0599(6) Uani 1 1 d . . . . .
H11A H 0.385654 0.365125 0.262297 0.090 Uiso 1 1 calc R U . . .
H11B H 0.429463 0.429584 0.337074 0.090 Uiso 1 1 calc R U . . .
H11C H 0.105030 0.373344 0.329759 0.090 Uiso 1 1 calc R U . . .
C13 C 0.8818(7) 0.10591(18) 0.48554(18) 0.0605(7) Uani 1 1 d . . . . .
H13A H 0.988758 0.070987 0.444058 0.091 Uiso 1 1 calc R U . . .
H13B H 0.706379 0.073550 0.511485 0.091 Uiso 1 1 calc R U . . .
H13C H 1.043130 0.122873 0.527230 0.091 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S5 C4 1.728(2) . ?
S5 C6 1.734(3) . ?
O10 C1 1.357(3) . ?
O10 C11 1.429(3) . ?
O12 C2 1.361(3) . ?
O12 C13 1.429(3) . ?
N7 C8 1.380(3) . ?
N7 C6 1.303(3) . ?
C8 C4 1.405(3) . ?
C8 C9 1.401(3) . ?
C1 C2 1.433(3) . ?
C1 C9 1.375(3) . ?
C4 C3 1.402(3) . ?
C2 C3 1.370(3) . ?
C3 H3 0.9300 . ?
C9 H9 0.9300 . ?
C6 C14 1.440(4) . ?
N15 C14 1.138(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
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
C4 S5 C6 87.95(12) . . ?
C1 O10 C11 116.92(18) . . ?
C2 O12 C13 117.3(2) . . ?
C6 N7 C8 109.2(2) . . ?
N7 C8 C4 115.1(2) . . ?
N7 C8 C9 124.7(2) . . ?
C9 C8 C4 120.2(2) . . ?
O10 C1 C2 113.84(19) . . ?
O10 C1 C9 125.3(2) . . ?
C9 C1 C2 120.9(2) . . ?
C8 C4 S5 110.07(17) . . ?
C3 C4 S5 128.2(2) . . ?
C3 C4 C8 121.7(2) . . ?
O12 C2 C1 113.8(2) . . ?
O12 C2 C3 125.1(2) . . ?
C3 C2 C1 121.1(2) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 C4 117.7(2) . . ?
C2 C3 H3 121.1 . . ?
C8 C9 H9 120.8 . . ?
C1 C9 C8 118.4(2) . . ?
C1 C9 H9 120.8 . . ?
N7 C6 S5 117.69(18) . . ?
N7 C6 C14 121.8(2) . . ?
C14 C6 S5 120.5(2) . . ?
N15 C14 C6 178.7(3) . . ?
O10 C11 H11A 109.5 . . ?
O10 C11 H11B 109.5 . . ?
O10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O12 C13 H13A 109.5 . . ?
O12 C13 H13B 109.5 . . ?
O12 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
S5 C4 C3 C2 179.20(18) . . . . ?
O10 C1 C2 O12 -0.1(3) . . . . ?
O10 C1 C2 C3 -179.2(2) . . . . ?
O10 C1 C9 C8 -179.8(2) . . . . ?
O12 C2 C3 C4 179.6(2) . . . . ?
N7 C8 C4 S5 0.8(3) . . . . ?
N7 C8 C4 C3 179.6(2) . . . . ?
N7 C8 C9 C1 -179.6(2) . . . . ?
C8 N7 C6 S5 -0.4(3) . . . . ?
C8 N7 C6 C14 178.4(2) . . . . ?
C8 C4 C3 C2 0.7(3) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C4 S5 C6 N7 0.7(2) . . . . ?
C4 S5 C6 C14 -178.1(2) . . . . ?
C4 C8 C9 C1 -0.3(3) . . . . ?
C2 C1 C9 C8 -0.4(3) . . . . ?
C9 C8 C4 S5 -178.58(18) . . . . ?
C9 C8 C4 C3 0.2(3) . . . . ?
C9 C1 C2 O12 -179.6(2) . . . . ?
C9 C1 C2 C3 1.3(4) . . . . ?
C6 S5 C4 C8 -0.81(18) . . . . ?
C6 S5 C4 C3 -179.4(2) . . . . ?
C6 N7 C8 C4 -0.3(3) . . . . ?
C6 N7 C8 C9 179.1(2) . . . . ?
C11 O10 C1 C2 174.7(2) . . . . ?
C11 O10 C1 C9 -5.9(3) . . . . ?
C13 O12 C2 C1 -178.9(2) . . . . ?
C13 O12 C2 C3 0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.558
_oxdiff_exptl_absorpt_empirical_full_min 0.531
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_240_auto
_database_code_depnum_ccdc_archive 'CCDC 2131718'
loop_
_audit_author_name
_audit_author_address
'Ahmed Alzamly' UAEU
_audit_update_record             
;
2021-12-30 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_audit_creation_date             2021-12-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 N2 O2 S'
_chemical_formula_sum            'C10 H8 N2 O2 S'
_chemical_formula_weight         220.24
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   13.7218(16)
_cell_length_b                   18.260(2)
_cell_length_c                   3.9580(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     991.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2265
_cell_measurement_temperature    297.00(10)
_cell_measurement_theta_max      72.9700
_cell_measurement_theta_min      3.9770
_shelx_estimated_absorpt_T_max   0.879
_shelx_estimated_absorpt_T_min   0.541
_exptl_absorpt_coefficient_mu    2.754
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.048
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            4966
_diffrn_reflns_point_group_measured_fraction_full 0.892
_diffrn_reflns_point_group_measured_fraction_max 0.821
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.921
_diffrn_reflns_theta_min         4.030
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9928
_diffrn_measured_fraction_theta_max 0.8194
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -57.00 -18.00   0.50   14.40    --  -90.00  50.00 148.00   78
  2  ω   -161.00 -81.00   0.50   14.40    --  -90.00-111.00 133.00  160
  3  ω   -161.00 -81.00   0.50   14.40    --  -90.00 -50.00   1.00  160
  4  ω     87.00 177.00   0.50   14.40    --  104.80  74.00 -17.00  180
  5  ω    -86.00 -35.00   0.50    3.60    --  -48.51 125.00 150.00  102
  6  ω    -86.00 -35.00   0.50    3.60    --  -48.51 125.00 -90.00  102
  7  ω    -26.00  23.00   0.50    3.60    --  -48.51  19.00  90.00   98
  8  ω    -23.00  26.00   0.50    3.60    --   48.51 -19.00 -60.00   98
  9  ω   -161.00-131.00   0.50   14.40    --  -90.00 -37.00 150.00   60
 10  ω   -161.00-131.00   0.50   14.40    --  -90.00 -37.00 120.00   60
 11  ω   -161.00-113.00   0.50   14.40    --  -90.00-125.00 120.00   96
 12  ω    131.00 177.00   0.50   14.40    --  104.80  37.00-150.00   92
 13  ω     33.00  66.00   0.50   14.40    --  104.80 -57.00-150.00   66
 14  ω   -120.00 -44.00   0.50    3.60    --  -48.51 -19.00 120.00  152
 15  ω     44.00  91.00   0.50    3.60    --   48.51  19.00 -60.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0196388000
_diffrn_orient_matrix_UB_12      -0.0823843000
_diffrn_orient_matrix_UB_13      -0.0493570000
_diffrn_orient_matrix_UB_21      0.0648837000
_diffrn_orient_matrix_UB_22      -0.0002363000
_diffrn_orient_matrix_UB_23      0.3174510000
_diffrn_orient_matrix_UB_31      -0.0894906000
_diffrn_orient_matrix_UB_32      -0.0181579000
_diffrn_orient_matrix_UB_33      0.2198233000
_diffrn_oxdiff_digest_frames     
;
014985b5738fa606a317642c4979a6368900025107a
;
_diffrn_oxdiff_digest_hkl        
;
011ac7e986689df2ecbf23b9215d7236cd10c4
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.525
_reflns_Friedel_fraction_full    0.757
_reflns_Friedel_fraction_max     0.666
_reflns_number_gt                1298
_reflns_number_total             1696
_reflns_odcompleteness_completeness 99.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 
;
 Flack x determined using 395 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1696
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0704
_refine_ls_restrained_S_all      1.121
_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)+(0.1196P)²+0.6250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1981
_refine_ls_wR_factor_ref         0.2219
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S8 S -0.55444(13) -0.57664(10) -0.5385(7) 0.0649(6) Uani 1 1 d . . . . .
O12 O -0.5709(4) -0.8449(3) -0.6091(19) 0.072(2) Uani 1 1 d . . . . .
O10 O -0.3605(4) -0.6015(3) -0.187(2) 0.0731(16) Uani 1 1 d . . . . .
N6 N -0.6390(4) -0.7001(3) -0.704(2) 0.0589(16) Uani 1 1 d . . . . .
C5 C -0.5512(5) -0.7171(4) -0.552(3) 0.0556(16) Uani 1 1 d . . . . .
C1 C -0.4051(6) -0.6653(5) -0.281(2) 0.061(2) Uani 1 1 d . . . . .
C9 C -0.4948(6) -0.6577(4) -0.443(2) 0.060(2) Uani 1 1 d . . . . .
C7 C -0.6464(5) -0.6293(4) -0.712(2) 0.0570(18) Uani 1 1 d . . . . .
C4 C -0.5145(6) -0.7891(4) -0.504(3) 0.066(2) Uani 1 1 d . . . . .
N15 N -0.7934(6) -0.5635(4) -0.984(3) 0.089(3) Uani 1 1 d . . . . .
C3 C -0.4258(6) -0.7959(5) -0.340(3) 0.070(2) Uani 1 1 d . . . . .
H3 H -0.401194 -0.842426 -0.297230 0.084 Uiso 1 1 calc R U . . .
C2 C -0.3723(6) -0.7348(5) -0.237(3) 0.070(2) Uani 1 1 d . . . . .
H2 H -0.312022 -0.741931 -0.134850 0.084 Uiso 1 1 calc R U . . .
C14 C -0.7284(7) -0.5933(5) -0.859(3) 0.069(2) Uani 1 1 d . . . . .
C13 C -0.5382(7) -0.9169(4) -0.562(4) 0.079(2) Uani 1 1 d . . . . .
H13A H -0.530479 -0.926339 -0.324669 0.119 Uiso 1 1 calc R U . . .
H13B H -0.476696 -0.923306 -0.673832 0.119 Uiso 1 1 calc R U . . .
H13C H -0.584931 -0.950471 -0.654585 0.119 Uiso 1 1 calc R U . . .
C11 C -0.2685(6) -0.6085(5) -0.027(3) 0.082(2) Uani 1 1 d . . . . .
H11A H -0.276780 -0.630901 0.190221 0.123 Uiso 1 1 calc R U . . .
H11B H -0.239762 -0.560938 -0.000117 0.123 Uiso 1 1 calc R U . . .
H11C H -0.226619 -0.638481 -0.163913 0.123 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S8 C9 1.732(8) . ?
S8 C7 1.729(7) . ?
O12 C4 1.345(10) . ?
O12 C13 1.403(9) . ?
O10 C1 1.369(10) . ?
O10 C11 1.418(10) . ?
N6 C5 1.381(10) . ?
N6 C7 1.298(9) . ?
C5 C9 1.400(11) . ?
C5 C4 1.421(11) . ?
C1 C9 1.395(12) . ?
C1 C2 1.357(11) . ?
C7 C14 1.427(12) . ?
C4 C3 1.385(13) . ?
N15 C14 1.156(12) . ?
C3 H3 0.9300 . ?
C3 C2 1.396(13) . ?
C2 H2 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
C7 S8 C9 87.5(4) . . ?
C4 O12 C13 119.0(7) . . ?
C1 O10 C11 116.2(7) . . ?
C7 N6 C5 107.6(6) . . ?
N6 C5 C9 116.2(7) . . ?
N6 C5 C4 125.0(7) . . ?
C9 C5 C4 118.7(7) . . ?
O10 C1 C9 115.7(7) . . ?
C2 C1 O10 127.8(8) . . ?
C2 C1 C9 116.5(8) . . ?
C5 C9 S8 109.5(6) . . ?
C1 C9 S8 127.1(6) . . ?
C1 C9 C5 123.4(7) . . ?
N6 C7 S8 119.1(5) . . ?
N6 C7 C14 122.1(7) . . ?
C14 C7 S8 118.8(6) . . ?
O12 C4 C5 117.1(8) . . ?
O12 C4 C3 125.7(7) . . ?
C3 C4 C5 117.2(7) . . ?
C4 C3 H3 119.1 . . ?
C4 C3 C2 121.8(8) . . ?
C2 C3 H3 119.1 . . ?
C1 C2 C3 122.3(8) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
N15 C14 C7 178.3(11) . . ?
O12 C13 H13A 109.5 . . ?
O12 C13 H13B 109.5 . . ?
O12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O10 C11 H11A 109.5 . . ?
O10 C11 H11B 109.5 . . ?
O10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
O12 C4 C3 C2 -179.5(10) . . . . ?
O10 C1 C9 S8 0.4(13) . . . . ?
O10 C1 C9 C5 -178.9(9) . . . . ?
O10 C1 C2 C3 178.8(10) . . . . ?
N6 C5 C9 S8 -0.3(11) . . . . ?
N6 C5 C9 C1 179.1(9) . . . . ?
N6 C5 C4 O12 -1.5(15) . . . . ?
N6 C5 C4 C3 -178.7(10) . . . . ?
C5 N6 C7 S8 -1.3(10) . . . . ?
C5 N6 C7 C14 179.0(9) . . . . ?
C5 C4 C3 C2 -2.5(15) . . . . ?
C9 S8 C7 N6 1.0(8) . . . . ?
C9 S8 C7 C14 -179.3(8) . . . . ?
C9 C5 C4 O12 179.6(8) . . . . ?
C9 C5 C4 C3 2.3(13) . . . . ?
C9 C1 C2 C3 -1.5(14) . . . . ?
C7 S8 C9 C5 -0.3(7) . . . . ?
C7 S8 C9 C1 -179.7(8) . . . . ?
C7 N6 C5 C9 1.0(11) . . . . ?
C7 N6 C5 C4 -178.0(9) . . . . ?
C4 C5 C9 S8 178.7(8) . . . . ?
C4 C5 C9 C1 -1.8(14) . . . . ?
C4 C3 C2 C1 2.2(17) . . . . ?
C2 C1 C9 S8 -179.3(8) . . . . ?
C2 C1 C9 C5 1.4(13) . . . . ?
C13 O12 C4 C5 -179.0(10) . . . . ?
C13 O12 C4 C3 -2.0(17) . . . . ?
C11 O10 C1 C9 -179.0(8) . . . . ?
C11 O10 C1 C2 0.7(15) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.196
_oxdiff_exptl_absorpt_empirical_full_min 0.231
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_229_auto
_database_code_depnum_ccdc_archive 'CCDC 2131717'
loop_
_audit_author_name
_audit_author_address
'Ahmed Alzamly'
;UAEU
United Arab Emirates
;
_audit_update_record             
;
2021-12-30 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_audit_creation_date             2021-12-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
ahmed.alzamly@uaeu.ac.ae
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 N2 O S'
_chemical_formula_sum            'C15 H10 N2 O S'
_chemical_formula_weight         266.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHON
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0053(3)
_cell_length_b                   8.4517(3)
_cell_length_c                   11.6853(6)
_cell_angle_alpha                86.836(3)
_cell_angle_beta                 77.121(4)
_cell_angle_gamma                71.464(4)
_cell_volume                     639.36(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8215
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      76.6260
_cell_measurement_theta_min      3.8460
_shelx_estimated_absorpt_T_max   0.805
_shelx_estimated_absorpt_T_min   0.506
_exptl_absorpt_coefficient_mu    2.182
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             276
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 0 -5 0.0658
2 0 5 0.0378
4 2 -3 0.0778
-4 -2 3 0.0690
0 5 2 0.1886
0 -5 -2 0.1616
0 -5 2 0.1307

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.104
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
-1.9971 -0.0019 -5.0017 0.1962 0.7100 0.0288
1.9971 0.0019 5.0017 -0.1962 -0.7100 -0.0288
4.0061 2.0017 -2.9966 -1.0034 0.2513 -0.2838
-4.0061 -2.0017 2.9966 1.0034 -0.2513 0.2838
-0.0051 4.9976 1.9998 0.3334 -0.0862 -0.9422
0.0051 -4.9976 -1.9998 -0.3334 0.0862 0.9422
0.0010 -4.9973 2.0001 -0.1176 -0.4083 0.8985

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12094
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.463
_diffrn_reflns_theta_min         3.881
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    113.00 177.00   0.50    0.10    --  104.80 125.00 150.00  128
  2  ω     79.00 167.00   0.50    0.10    --  104.80 148.00 136.00  176
  3  ω     96.00 177.00   0.50    0.10    --  104.80 123.00 -26.00  162
  4  ω    131.00 177.00   0.50    0.10    --  104.80  37.00-150.00   92
  5  ω     33.00 106.00   0.50    0.10    --  104.80 -99.00   0.00  146
  6  ω     47.00 108.00   0.50    0.05    --   49.51-148.00  89.00  122
  7  ω     47.00 128.00   0.50    0.10    --  104.80-148.00  89.00  162
  8  ω     33.00 106.00   0.50    0.10    --  104.80 -99.00 120.00  146
  9  ω     33.00 106.00   0.50    0.10    --  104.80 -99.00 -60.00  146
 10  ω     33.00 110.00   0.50    0.10    --  104.80-123.00-106.00  154
 11  ω     33.00 106.00   0.50    0.10    --  104.80 -99.00 -90.00  146
 12  ω     35.00 111.00   0.50    0.10    --  104.80-125.00-150.00  152
 13  ω     33.00  93.00   0.50    0.05    --   49.51-123.00-106.00  120
 14  ω     33.00 106.00   0.50    0.10    --  104.80 -99.00  90.00  146
 15  ω     33.00  66.00   0.50    0.10    --  104.80 -57.00 120.00   66
 16  ω     33.00  66.00   0.50    0.10    --  104.80 -57.00  90.00   66
 17  ω     33.00  66.00   0.50    0.10    --  104.80 -57.00 -60.00   66
 18  ω     33.00  66.00   0.50    0.10    --  104.80 -57.00 -90.00   66
 19  ω    -26.00  22.00   0.50    0.05    --  -49.51  19.00-120.00   96
 20  ω    -98.00 -43.00   0.50    0.05    --  -49.51   0.00-150.00  110
 21  ω    -26.00  22.00   0.50    0.05    --  -49.51  19.00 -90.00   96
 22  ω    -26.00  22.00   0.50    0.05    --  -49.51  19.00   0.00   96
 23  ω    -84.00 -11.00   0.50    0.05    --  -49.51 123.00 -26.00  146
 24  ω    -66.00 -18.00   0.50    0.10    --  -90.00  57.00 -30.00   96
 25  ω   -102.00 -25.00   0.50    0.05    --  -49.51 148.00 136.00  154
 26  ω   -102.00 -25.00   0.50    0.10    --  -90.00 148.00 136.00  154
 27  ω    -66.00 -18.00   0.50    0.10    --  -90.00  57.00  90.00   96
 28  ω   -138.00 -83.00   0.50    0.10    --  -90.00   0.00  90.00  110
 29  ω   -121.00 -45.00   0.50    0.05    --  -49.51 -19.00 -60.00  152
 30  ω   -161.00-134.00   0.50    0.10    --  -90.00 -77.00-150.00   54
 31  ω   -161.00-134.00   0.50    0.10    --  -90.00 -77.00 -90.00   54
 32  ω   -161.00-131.00   0.50    0.10    --  -90.00 -37.00 -90.00   60
 33  ω   -161.00-131.00   0.50    0.10    --  -90.00 -37.00 -60.00   60
 34  ω   -121.00 -45.00   0.50    0.05    --  -49.51 -19.00-180.00  152
 35  ω   -161.00-131.00   0.50    0.10    --  -90.00 -37.00   0.00   60
 36  ω   -161.00-131.00   0.50    0.10    --  -90.00 -37.00  30.00   60
 37  ω   -161.00-134.00   0.50    0.10    --  -90.00 -77.00  30.00   54
 38  ω   -161.00-126.00   0.50    0.10    --  -90.00 -99.00 -30.00   70
 39  ω   -161.00 -75.00   0.50    0.10    --  -90.00-123.00-106.00  172
 40  ω   -120.00 -57.00   0.50    0.05    --  -49.51-148.00  89.00  126
 41  ω   -151.00 -57.00   0.50    0.10    --  -90.00-148.00  89.00  188
 42  ω   -161.00-113.00   0.50    0.10    --  -90.00-125.00 120.00   96
 43  ω   -161.00-126.00   0.50    0.10    --  -90.00 -99.00 150.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2327709000
_diffrn_orient_matrix_UB_12      0.0449788000
_diffrn_orient_matrix_UB_13      0.0537025000
_diffrn_orient_matrix_UB_21      -0.0458607000
_diffrn_orient_matrix_UB_22      0.0321949000
_diffrn_orient_matrix_UB_23      -0.1236620000
_diffrn_orient_matrix_UB_31      0.0130191000
_diffrn_orient_matrix_UB_32      -0.1841516000
_diffrn_orient_matrix_UB_33      -0.0108970000
_diffrn_oxdiff_digest_frames     
;
01c7c045c5f0dd209dab8b60ceef37c63e000626151
;
_diffrn_oxdiff_digest_hkl        
;
01b03f2a82989fdee6a68829be65f0339c8042
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2331
_reflns_number_total             2576
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2576
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.062
_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)+(0.0588P)²+0.1012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1089
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C17(H17), C9(H9), C13(H13), C15(H15), C16(H16), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S6 S 0.41176(7) 0.03989(5) 0.28823(4) 0.05801(16) Uani 1 1 d . . . . .
O10 O -0.01349(17) 0.45481(15) 0.71004(11) 0.0611(3) Uani 1 1 d . . . . .
N4 N 0.5846(2) 0.19562(16) 0.39922(12) 0.0510(3) Uani 1 1 d . . . . .
C12 C 0.2412(2) 0.43429(18) 0.83004(14) 0.0498(3) Uani 1 1 d . . . . .
C3 C 0.3826(2) 0.23012(18) 0.46030(13) 0.0457(3) Uani 1 1 d . . . . .
C7 C 0.2639(2) 0.15611(18) 0.41269(14) 0.0479(3) Uani 1 1 d . . . . .
C1 C 0.0926(2) 0.35673(19) 0.61326(14) 0.0496(4) Uani 1 1 d . . . . .
C2 C 0.2971(2) 0.33149(19) 0.56123(14) 0.0501(4) Uani 1 1 d . . . . .
H2 H 0.376129 0.380614 0.592434 0.060 Uiso 1 1 calc R U . . .
C5 C 0.6163(3) 0.09901(19) 0.30918(14) 0.0520(4) Uani 1 1 d . . . . .
C8 C 0.0570(3) 0.1821(2) 0.46614(16) 0.0554(4) Uani 1 1 d . . . . .
H8 H -0.023004 0.133651 0.435194 0.066 Uiso 1 1 calc R U . . .
C17 C 0.1846(3) 0.3213(2) 0.91015(15) 0.0572(4) Uani 1 1 d . . . . .
H17 H 0.053935 0.310330 0.920147 0.069 Uiso 1 1 calc R U . . .
C9 C -0.0250(2) 0.2806(2) 0.56510(16) 0.0557(4) Uani 1 1 d . . . . .
H9 H -0.162401 0.298028 0.601848 0.067 Uiso 1 1 calc R U . . .
C11 C 0.0923(3) 0.5435(2) 0.76121(16) 0.0586(4) Uani 1 1 d . . . . .
H11A H -0.008981 0.631302 0.812740 0.070 Uiso 1 1 calc R U . . .
H11B H 0.167088 0.595976 0.699082 0.070 Uiso 1 1 calc R U . . .
N19 N 0.9697(3) 0.0148(3) 0.16505(18) 0.0883(6) Uani 1 1 d . . . . .
C13 C 0.4363(3) 0.4479(2) 0.81739(16) 0.0597(4) Uani 1 1 d . . . . .
H13 H 0.477247 0.522809 0.763933 0.072 Uiso 1 1 calc R U . . .
C15 C 0.5126(3) 0.2409(2) 0.96172(17) 0.0660(5) Uani 1 1 d . . . . .
H15 H 0.603408 0.176510 1.006014 0.079 Uiso 1 1 calc R U . . .
C16 C 0.3202(3) 0.2249(2) 0.97523(16) 0.0629(4) Uani 1 1 d . . . . .
H16 H 0.281024 0.148870 1.028309 0.075 Uiso 1 1 calc R U . . .
C18 C 0.8133(3) 0.0484(2) 0.22827(17) 0.0620(4) Uani 1 1 d . . . . .
C14 C 0.5710(3) 0.3522(2) 0.88281(18) 0.0694(5) Uani 1 1 d . . . . .
H14 H 0.701616 0.362923 0.873482 0.083 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S6 C7 1.7299(17) . ?
S6 C5 1.7282(16) . ?
O10 C1 1.362(2) . ?
O10 C11 1.438(2) . ?
N4 C3 1.381(2) . ?
N4 C5 1.303(2) . ?
C12 C17 1.387(2) . ?
C12 C11 1.506(2) . ?
C12 C13 1.382(2) . ?
C3 C7 1.403(2) . ?
C3 C2 1.398(2) . ?
C7 C8 1.396(2) . ?
C1 C2 1.378(2) . ?
C1 C9 1.412(2) . ?
C2 H2 0.9300 . ?
C5 C18 1.439(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.366(2) . ?
C17 H17 0.9300 . ?
C17 C16 1.381(3) . ?
C9 H9 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
N19 C18 1.136(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.370(3) . ?
C15 C14 1.372(3) . ?
C16 H16 0.9300 . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S6 C7 87.96(7) . . ?
C1 O10 C11 118.23(13) . . ?
C5 N4 C3 109.38(13) . . ?
C17 C12 C11 121.03(15) . . ?
C13 C12 C17 118.28(15) . . ?
C13 C12 C11 120.65(15) . . ?
N4 C3 C7 114.75(14) . . ?
N4 C3 C2 124.14(13) . . ?
C2 C3 C7 121.11(14) . . ?
C3 C7 S6 110.18(12) . . ?
C8 C7 S6 129.58(12) . . ?
C8 C7 C3 120.24(15) . . ?
O10 C1 C2 125.14(14) . . ?
O10 C1 C9 114.68(14) . . ?
C2 C1 C9 120.18(15) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 C3 118.25(14) . . ?
C1 C2 H2 120.9 . . ?
N4 C5 S6 117.73(13) . . ?
N4 C5 C18 120.76(15) . . ?
C18 C5 S6 121.48(13) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 C7 118.27(15) . . ?
C9 C8 H8 120.9 . . ?
C12 C17 H17 119.7 . . ?
C16 C17 C12 120.65(16) . . ?
C16 C17 H17 119.7 . . ?
C1 C9 H9 119.0 . . ?
C8 C9 C1 121.96(15) . . ?
C8 C9 H9 119.0 . . ?
O10 C11 C12 113.64(13) . . ?
O10 C11 H11A 108.8 . . ?
O10 C11 H11B 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 120.95(16) . . ?
C14 C13 H13 119.5 . . ?
C16 C15 H15 120.0 . . ?
C16 C15 C14 119.96(17) . . ?
C14 C15 H15 120.0 . . ?
C17 C16 H16 119.9 . . ?
C15 C16 C17 120.11(16) . . ?
C15 C16 H16 119.9 . . ?
N19 C18 C5 177.1(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.05(18) . . ?
C15 C14 H14 120.0 . . ?

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
S6 C7 C8 C9 -179.96(12) . . . . ?
O10 C1 C2 C3 -178.45(14) . . . . ?
O10 C1 C9 C8 178.20(14) . . . . ?
N4 C3 C7 S6 0.20(16) . . . . ?
N4 C3 C7 C8 -179.72(13) . . . . ?
N4 C3 C2 C1 179.53(13) . . . . ?
C12 C17 C16 C15 0.5(3) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C3 N4 C5 S6 -0.05(17) . . . . ?
C3 N4 C5 C18 177.96(14) . . . . ?
C3 C7 C8 C9 -0.1(2) . . . . ?
C7 S6 C5 N4 0.14(13) . . . . ?
C7 S6 C5 C18 -177.85(14) . . . . ?
C7 C3 C2 C1 0.2(2) . . . . ?
C7 C8 C9 C1 0.5(2) . . . . ?
C1 O10 C11 C12 -75.38(18) . . . . ?
C2 C3 C7 S6 179.61(11) . . . . ?
C2 C3 C7 C8 -0.3(2) . . . . ?
C2 C1 C9 C8 -0.7(2) . . . . ?
C5 S6 C7 C3 -0.18(11) . . . . ?
C5 S6 C7 C8 179.73(15) . . . . ?
C5 N4 C3 C7 -0.10(18) . . . . ?
C5 N4 C3 C2 -179.49(14) . . . . ?
C17 C12 C11 O10 -46.7(2) . . . . ?
C17 C12 C13 C14 -0.2(3) . . . . ?
C9 C1 C2 C3 0.3(2) . . . . ?
C11 O10 C1 C2 1.8(2) . . . . ?
C11 O10 C1 C9 -177.03(13) . . . . ?
C11 C12 C17 C16 -178.22(15) . . . . ?
C11 C12 C13 C14 177.92(16) . . . . ?
C13 C12 C17 C16 -0.1(2) . . . . ?
C13 C12 C11 O10 135.24(16) . . . . ?
C16 C15 C14 C13 0.2(3) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.437
_oxdiff_exptl_absorpt_empirical_full_min 0.708
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_233_auto
_database_code_depnum_ccdc_archive 'CCDC 2131722'
loop_
_audit_author_name
_audit_author_address
'Ahmed Alzamly' UAEU
_audit_update_record             
;
2021-12-30 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_audit_creation_date             2021-12-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H9 I N2 O3'
_chemical_formula_sum            'C10 H9 I N2 O3'
_chemical_formula_weight         332.09
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
I I -0.3257 6.8362 '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                   14.7562(4)
_cell_length_b                   4.73210(10)
_cell_length_c                   16.9571(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.469(2)
_cell_angle_gamma                90
_cell_volume                     1160.43(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7623
_cell_measurement_temperature    297.00(10)
_cell_measurement_theta_max      76.7000
_cell_measurement_theta_min      5.2720
_shelx_estimated_absorpt_T_max   0.671
_shelx_estimated_absorpt_T_min   0.221
_exptl_absorpt_coefficient_mu    21.669
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.901
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 3 -2 0.0896
0 -3 2 0.0896
5 0 -3 0.0347
-5 0 3 0.0347
-5 0 3 0.0297
5 0 -3 0.0297
-1 -1 1 0.0567
1 1 -1 0.0567

_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
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
0.0005 3.0020 -1.9978 0.0550 0.4143 -0.9024
-0.0005 -3.0020 1.9978 -0.0550 -0.4143 0.9024
5.0001 0.0009 -3.0057 -0.1286 -0.4682 -0.2583
-5.0001 -0.0009 3.0057 0.1286 0.4682 0.2583
-5.0001 -0.0009 3.0057 0.1286 0.4682 0.2583
5.0001 0.0009 -3.0057 -0.1286 -0.4682 -0.2583
-1.0003 -1.0007 1.0004 -0.0165 -0.0436 0.3463
1.0003 1.0007 -1.0004 0.0165 0.0436 -0.3463

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11384
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.660
_diffrn_reflns_theta_min         3.056
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9401
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     45.00 111.00   0.50    0.12    --   49.76  19.00  90.00  132
  2  ω     44.00 121.00   0.50    0.12    --   49.76  38.00 138.00  154
  3  ω     99.00 176.00   0.50    0.46    --  104.80  38.00 138.00  154
  4  ω    137.00 177.00   0.50    0.46    --  104.80  57.00   0.00   80
  5  ω     33.00  66.00   0.50    0.46    --  104.80 -57.00-150.00   66
  6  ω     33.00  66.00   0.50    0.46    --  104.80 -57.00-180.00   66
  7  ω     33.00  66.00   0.50    0.46    --  104.80 -57.00-120.00   66
  8  ω    -21.00  43.00   0.50    0.12    --   49.76 -38.00 -16.00  128
  9  ω     33.00  66.00   0.50    0.46    --  104.80 -57.00   0.00   66
 10  ω     33.00  66.00   0.50    0.46    --  104.80 -57.00  30.00   66
 11  ω     33.00  66.00   0.50    0.46    --  104.80 -57.00  60.00   66
 12  ω     33.00  66.00   0.50    0.46    --  104.80 -57.00 150.00   66
 13  ω     33.00 106.00   0.50    0.46    --  104.80 -99.00 -90.00  146
 14  ω    -26.00  22.00   0.50    0.12    --  -49.76  19.00 -90.00   96
 15  ω    -43.00  21.00   0.50    0.12    --  -49.76  38.00 138.00  128
 16  ω    -98.00 -43.00   0.50    0.12    --  -49.76   0.00  90.00  110
 17  ω   -161.00-134.00   0.50    0.46    --  -90.00 -77.00 120.00   54
 18  ω   -161.00-134.00   0.50    0.46    --  -90.00 -77.00  30.00   54
 19  ω   -161.00-134.00   0.50    0.46    --  -90.00 -77.00   0.00   54
 20  ω   -161.00-134.00   0.50    0.46    --  -90.00 -77.00 -30.00   54
 21  ω   -161.00-134.00   0.50    0.46    --  -90.00 -77.00 -90.00   54
 22  ω   -161.00-131.00   0.50    0.46    --  -90.00 -37.00-150.00   60
 23  ω   -161.00-131.00   0.50    0.46    --  -90.00 -37.00-120.00   60
 24  ω   -161.00 -84.00   0.50    0.46    --  -90.00 -38.00 -16.00  154
 25  ω   -120.00 -44.00   0.50    0.12    --  -49.76 -38.00 -16.00  152
 26  ω   -161.00-131.00   0.50    0.46    --  -90.00 -37.00 -60.00   60
 27  ω   -161.00-131.00   0.50    0.46    --  -90.00 -37.00 -90.00   60
 28  ω   -121.00 -45.00   0.50    0.12    --  -49.76 -19.00-150.00  152
 29  ω   -161.00-126.00   0.50    0.46    --  -90.00 -99.00-180.00   70
 30  ω   -161.00-126.00   0.50    0.46    --  -90.00 -99.00 150.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0282071000
_diffrn_orient_matrix_UB_12      0.0780245000
_diffrn_orient_matrix_UB_13      0.0897339000
_diffrn_orient_matrix_UB_21      -0.0955656000
_diffrn_orient_matrix_UB_22      0.1359362000
_diffrn_orient_matrix_UB_23      -0.0031641000
_diffrn_orient_matrix_UB_31      -0.0377563000
_diffrn_orient_matrix_UB_32      -0.2852677000
_diffrn_orient_matrix_UB_33      0.0230321000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2079
_reflns_number_total             2300
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.827
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0288
_refine_ls_restrained_S_all      1.051
_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)+(0.0363P)²+1.1012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0761
_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 Aromatic/amide H refined with riding coordinates:
 N8(H8), C6(H6), C3(H3)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I7 I 0.91071(2) 1.15912(5) 0.68408(2) 0.06012(12) Uani 1 1 d . . . . .
O13 O 0.89724(19) 1.2367(7) 0.49996(17) 0.0642(7) Uani 1 1 d . . . . .
O15 O 0.6515(2) 0.5696(6) 0.39802(14) 0.0598(7) Uani 1 1 d . . . . .
N8 N 0.6374(2) 0.4260(6) 0.54225(16) 0.0441(6) Uani 1 1 d . . . . .
H8 H 0.606167 0.356871 0.498231 0.053 Uiso 1 1 calc R U . . .
O12 O 0.6523(2) 0.3931(6) 0.67909(15) 0.0699(8) Uani 1 1 d . . . . .
N11 N 0.4971(3) -0.0832(8) 0.5927(2) 0.0688(9) Uani 1 1 d . . . . .
C6 C 0.7602(2) 0.7695(7) 0.59931(19) 0.0426(7) Uani 1 1 d . . . . .
H6 H 0.755647 0.723469 0.651695 0.051 Uiso 1 1 calc R U . . .
C2 C 0.8315(2) 1.0408(8) 0.5077(2) 0.0488(8) Uani 1 1 d . . . . .
C5 C 0.7033(2) 0.6377(6) 0.53509(19) 0.0416(7) Uani 1 1 d . . . . .
C3 C 0.7737(3) 0.9139(7) 0.4433(2) 0.0506(8) Uani 1 1 d . . . . .
H3 H 0.777710 0.963255 0.391041 0.061 Uiso 1 1 calc R U . . .
C10 C 0.5487(3) 0.0931(8) 0.5981(2) 0.0520(8) Uani 1 1 d . . . . .
C1 C 0.8238(2) 0.9696(7) 0.5858(2) 0.0464(7) Uani 1 1 d . . . . .
C9 C 0.6191(3) 0.3231(7) 0.6113(2) 0.0476(8) Uani 1 1 d . . . . .
C4 C 0.7096(2) 0.7133(7) 0.45625(19) 0.0457(7) Uani 1 1 d . . . . .
C14 C 0.9135(3) 1.2893(10) 0.4213(3) 0.0762(13) Uani 1 1 d . . . . .
H14A H 0.858766 1.367640 0.388362 0.114 Uiso 1 1 calc R U . . .
H14B H 0.928945 1.115311 0.397986 0.114 Uiso 1 1 calc R U . . .
H14C H 0.963710 1.420472 0.424392 0.114 Uiso 1 1 calc R U . . .
C16 C 0.6458(4) 0.6495(11) 0.3160(2) 0.0774(14) Uani 1 1 d . . . . .
H16A H 0.594791 0.553462 0.282767 0.116 Uiso 1 1 calc R U . . .
H16B H 0.702149 0.598792 0.299331 0.116 Uiso 1 1 calc R U . . .
H16C H 0.636646 0.849980 0.310639 0.116 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I7 C1 2.091(3) . ?
O13 C2 1.367(4) . ?
O13 C14 1.424(5) . ?
O15 C4 1.355(4) . ?
O15 C16 1.428(4) . ?
N8 H8 0.8600 . ?
N8 C5 1.418(4) . ?
N8 C9 1.344(4) . ?
O12 C9 1.203(4) . ?
N11 C10 1.121(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.384(5) . ?
C6 C1 1.384(5) . ?
C2 C3 1.382(5) . ?
C2 C1 1.394(5) . ?
C5 C4 1.405(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(5) . ?
C10 C9 1.490(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O13 C14 117.6(3) . . ?
C4 O15 C16 118.9(3) . . ?
C5 N8 H8 116.9 . . ?
C9 N8 H8 116.9 . . ?
C9 N8 C5 126.2(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C1 C6 C5 120.3(3) . . ?
O13 C2 C3 123.9(3) . . ?
O13 C2 C1 116.6(3) . . ?
C3 C2 C1 119.5(3) . . ?
C6 C5 N8 124.8(3) . . ?
C6 C5 C4 119.3(3) . . ?
C4 C5 N8 116.0(3) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
N11 C10 C9 176.1(4) . . ?
C6 C1 I7 119.4(2) . . ?
C6 C1 C2 120.5(3) . . ?
C2 C1 I7 120.1(3) . . ?
N8 C9 C10 112.9(3) . . ?
O12 C9 N8 128.2(3) . . ?
O12 C9 C10 118.9(3) . . ?
O15 C4 C5 114.4(3) . . ?
O15 C4 C3 125.5(3) . . ?
C3 C4 C5 120.1(3) . . ?
O13 C14 H14A 109.5 . . ?
O13 C14 H14B 109.5 . . ?
O13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O15 C16 H16A 109.5 . . ?
O15 C16 H16B 109.5 . . ?
O15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
O13 C2 C3 C4 178.9(3) . . . . ?
O13 C2 C1 I7 -0.2(4) . . . . ?
O13 C2 C1 C6 -178.9(3) . . . . ?
N8 C5 C4 O15 -0.5(4) . . . . ?
N8 C5 C4 C3 -178.5(3) . . . . ?
C6 C5 C4 O15 179.4(3) . . . . ?
C6 C5 C4 C3 1.3(5) . . . . ?
C2 C3 C4 O15 -177.9(3) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C5 N8 C9 O12 2.1(6) . . . . ?
C5 N8 C9 C10 -177.5(3) . . . . ?
C5 C6 C1 I7 -178.7(2) . . . . ?
C5 C6 C1 C2 0.0(5) . . . . ?
C3 C2 C1 I7 180.0(3) . . . . ?
C3 C2 C1 C6 1.3(5) . . . . ?
C1 C6 C5 N8 178.6(3) . . . . ?
C1 C6 C5 C4 -1.3(5) . . . . ?
C1 C2 C3 C4 -1.2(5) . . . . ?
C9 N8 C5 C6 0.8(5) . . . . ?
C9 N8 C5 C4 -179.4(3) . . . . ?
C14 O13 C2 C3 -7.0(6) . . . . ?
C14 O13 C2 C1 173.1(3) . . . . ?
C16 O15 C4 C5 173.9(4) . . . . ?
C16 O15 C4 C3 -8.2(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.263
_oxdiff_exptl_absorpt_empirical_full_min 0.666
