# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_sh36_150_auto
_database_code_depnum_ccdc_archive 'CCDC 2156456'
loop_
_audit_author_name
_audit_author_address
'Frederick P. Malan'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2022-03-04 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2022-02-24
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 Br N2 O3'
_chemical_formula_sum            'C13 H8 Br0.25 Cl N2 O3'
_chemical_formula_weight         295.64
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N4 O4 Cl'
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'
Br Br -0.6763 1.2805 '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                   7.44030(10)
_cell_length_b                   11.5220(2)
_cell_length_c                   14.0179(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.6690(10)
_cell_angle_gamma                90
_cell_volume                     1199.25(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12756
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      78.2260
_cell_measurement_theta_min      3.1770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.876
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             599
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14931
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.955
_diffrn_reflns_theta_min         4.973
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     27.00 119.00   0.50    0.05    --   46.83  71.00 141.00  184
  2  ω     32.00 118.00   0.50    0.05    --   46.83  57.00  90.00  172
  3  ω     32.00 118.00   0.50    0.05    --   46.83  57.00 -90.00  172
  4  ω     32.00 118.00   0.50    0.05    --   46.83  57.00-150.00  172
  5  ω     -5.00  29.00   0.50    0.05    --  -46.83  19.00-120.00   68
  6  ω     -5.00  29.00   0.50    0.05    --  -46.83  19.00 -60.00   68
  7  ω    -67.00  26.00   0.50    0.05    --  -46.83  71.00 141.00  186
  8  ω     90.00 178.00   0.50    0.06    --  110.25  71.00 141.00  176
  9  ω     97.00 175.00   0.50    0.06    --  110.25  15.00 120.00  156
 10  ω     98.00 178.00   0.50    0.06    --  110.25  45.00  60.00  160
 11  ω     94.00 178.00   0.50    0.06    --  110.25  61.00  90.00  168
 12  ω     97.00 175.00   0.50    0.06    --  110.25  15.00  30.00  156
 13  ω     97.00 175.00   0.50    0.06    --  110.25  15.00 -90.00  156
 14  ω     97.00 175.00   0.50    0.06    --  110.25  15.00-150.00  156
 15  ω    -25.00  67.00   0.50    0.05    --   46.83 -71.00  11.00  184
 16  ω     38.00  80.00   0.50    0.06    --  110.25 -61.00-120.00   84
 17  ω     38.00 131.00   0.50    0.06    --  110.25 -71.00  11.00  186
 18  ω     38.00  80.00   0.50    0.06    --  110.25 -61.00  30.00   84
 19  ω     38.00  80.00   0.50    0.06    --  110.25 -61.00  90.00   84
 20  ω     38.00  80.00   0.50    0.06    --  110.25 -61.00 150.00   84
 21  ω    -27.00  13.00   0.50    0.05    --   46.83 -19.00   0.00   80
 22  ω     38.00 106.00   0.50    0.06    --  110.25 -94.00   0.00  136
 23  ω     38.00 106.00   0.50    0.06    --  110.25 -94.00 -90.00  136
 24  ω     38.00 111.00   0.50    0.06    --  110.25-125.00-150.00  146
 25  ω     38.00 106.00   0.50    0.06    --  110.25 -94.00-120.00  136
 26  ω     18.00  95.00   0.50    0.05    --   46.83-125.00-120.00  154
 27  ω   -122.00 -29.00   0.50    0.06    -- -102.00  71.00 141.00  186
 28  ω    -72.00 -29.00   0.50    0.06    -- -102.00  61.00   0.00   86
 29  ω    -72.00 -29.00   0.50    0.06    -- -102.00  61.00 -30.00   86
 30  ω   -175.00 -82.00   0.50    0.06    -- -102.00 -71.00  11.00  186
 31  ω   -118.00 -24.00   0.50    0.05    --  -46.83 -77.00  30.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1596821000
_diffrn_orient_matrix_UB_12      -0.0251499000
_diffrn_orient_matrix_UB_13      0.0616433000
_diffrn_orient_matrix_UB_21      0.1024219000
_diffrn_orient_matrix_UB_22      -0.1044571000
_diffrn_orient_matrix_UB_23      0.0453954000
_diffrn_orient_matrix_UB_31      0.0840860000
_diffrn_orient_matrix_UB_32      0.0795360000
_diffrn_orient_matrix_UB_33      0.0791782000
_diffrn_oxdiff_digest_frames     
;
01d72d15dfc8ca018cf6ffa3eef2a36f71000411571
;
_diffrn_oxdiff_digest_hkl        
;
01b2799e446788e5c44ce6ca9240cd1490504e
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2429
_reflns_number_total             2522
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2522
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0256
_refine_ls_restrained_S_all      1.037
_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)+(0.0349P)²+1.0760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0677
_refine_ls_wR_factor_ref         0.0683
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C4(H4), C13(H13), C7(H7), C11(H11), C10(H10), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O19(H19)
;
_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
Br1 Br 0.91070(3) 0.60402(2) 0.76032(2) 0.03005(9) Uani 1 1 d . . . . .
O19 O 0.88965(19) 0.35546(12) 0.59477(9) 0.0282(3) Uani 1 1 d . . . . .
H19 H 0.880864 0.427641 0.601516 0.042 Uiso 1 1 calc GR . . . .
O21 O 0.5795(2) 0.11430(13) 0.22177(12) 0.0369(4) Uani 1 1 d . . . . .
O20 O 0.5481(2) 0.29427(15) 0.18052(11) 0.0425(4) Uani 1 1 d . . . . .
N8 N 0.7846(2) 0.56622(14) 0.55223(11) 0.0223(3) Uani 1 1 d . . . . .
N16 N 0.5937(2) 0.21870(16) 0.23863(11) 0.0289(4) Uani 1 1 d . . . . .
C3 C 0.6676(2) 0.25483(16) 0.33270(13) 0.0234(4) Uani 1 1 d . . . . .
C2 C 0.6546(2) 0.37008(17) 0.35773(13) 0.0235(4) Uani 1 1 d . . . . .
H2 H 0.596857 0.424026 0.314632 0.028 Uiso 1 1 calc R . . . .
C1 C 0.7270(2) 0.40680(15) 0.44714(13) 0.0212(4) Uani 1 1 d . . . . .
C9 C 0.7721(2) 0.68450(16) 0.57722(13) 0.0223(4) Uani 1 1 d . . . . .
C6 C 0.8134(2) 0.32443(16) 0.50948(13) 0.0228(4) Uani 1 1 d . . . . .
C14 C 0.8248(2) 0.71780(16) 0.67115(13) 0.0225(4) Uani 1 1 d . . . . .
C5 C 0.8205(3) 0.20736(17) 0.48274(14) 0.0268(4) Uani 1 1 d . . . . .
H5 H 0.875323 0.151968 0.525550 0.032 Uiso 1 1 calc R . . . .
C4 C 0.7481(3) 0.17254(17) 0.39442(14) 0.0258(4) Uani 1 1 d . . . . .
H4 H 0.752943 0.093364 0.375861 0.031 Uiso 1 1 calc R . . . .
C13 C 0.8169(3) 0.83201(17) 0.70078(14) 0.0273(4) Uani 1 1 d . . . . .
H13 H 0.854932 0.852476 0.764551 0.033 Uiso 1 1 calc R . . . .
C7 C 0.7124(2) 0.52798(16) 0.47294(13) 0.0231(4) Uani 1 1 d . . . . .
H7 H 0.648297 0.579852 0.430485 0.028 Uiso 1 1 calc R . . . .
C11 C 0.7028(3) 0.88596(17) 0.54323(16) 0.0308(4) Uani 1 1 d . . . . .
H11 H 0.660427 0.943873 0.499074 0.037 Uiso 1 1 calc R . . . .
C10 C 0.7136(3) 0.77197(17) 0.51367(14) 0.0278(4) Uani 1 1 d . . . . .
H10 H 0.680773 0.752759 0.448991 0.033 Uiso 1 1 calc R . . . .
C12 C 0.7531(3) 0.91657(18) 0.63676(16) 0.0303(4) Uani 1 1 d . . . . .
H12 H 0.743893 0.994949 0.656923 0.036 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
Br1 C14 1.8940(18) . ?
O19 C6 1.339(2) . ?
O21 N16 1.229(2) . ?
O20 N16 1.225(2) . ?
N8 C9 1.412(2) . ?
N8 C7 1.281(2) . ?
N16 C3 1.457(2) . ?
C3 C2 1.379(3) . ?
C3 C4 1.393(3) . ?
C2 C1 1.398(3) . ?
C1 C6 1.416(3) . ?
C1 C7 1.448(3) . ?
C9 C14 1.403(2) . ?
C9 C10 1.396(3) . ?
C6 C5 1.402(3) . ?
C14 C13 1.382(3) . ?
C5 C4 1.378(3) . ?
C13 C12 1.388(3) . ?
C11 C10 1.381(3) . ?
C11 C12 1.386(3) . ?

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 N8 C9 121.10(16) . . ?
O21 N16 C3 118.47(18) . . ?
O20 N16 O21 123.42(17) . . ?
O20 N16 C3 118.11(17) . . ?
C2 C3 N16 118.49(17) . . ?
C2 C3 C4 122.15(17) . . ?
C4 C3 N16 119.35(17) . . ?
C3 C2 C1 119.36(17) . . ?
C2 C1 C6 118.96(17) . . ?
C2 C1 C7 119.01(17) . . ?
C6 C1 C7 122.03(17) . . ?
C14 C9 N8 118.55(16) . . ?
C10 C9 N8 124.16(17) . . ?
C10 C9 C14 117.28(17) . . ?
O19 C6 C1 121.45(17) . . ?
O19 C6 C5 118.34(17) . . ?
C5 C6 C1 120.21(17) . . ?
C9 C14 Br1 119.49(14) . . ?
C13 C14 Br1 118.66(14) . . ?
C13 C14 C9 121.84(17) . . ?
C4 C5 C6 120.07(18) . . ?
C5 C4 C3 119.20(17) . . ?
C14 C13 C12 119.57(18) . . ?
N8 C7 C1 120.94(17) . . ?
C10 C11 C12 120.55(19) . . ?
C11 C10 C9 121.13(18) . . ?
C11 C12 C13 119.58(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.970
_oxdiff_exptl_absorpt_empirical_full_min 0.621
_chemical_properties_physical    Light-sensitive,Photo-sensitive
####################################################################### 
# 
# 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_sh36_210_auto
_database_code_depnum_ccdc_archive 'CCDC 2156458'
loop_
_audit_author_name
_audit_author_address
'Frederick P. Malan'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2022-03-04 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2022-02-24
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 Br N2 O3'
_chemical_formula_sum            'C13 H8 Br N2 O3'
_chemical_formula_weight         320.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N4 O4 Br'
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      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                   7.49820(10)
_cell_length_b                   11.5476(2)
_cell_length_c                   14.0374(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.8690(10)
_cell_angle_gamma                90
_cell_volume                     1212.68(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12726
_cell_measurement_temperature    210.00(10)
_cell_measurement_theta_max      78.5220
_cell_measurement_theta_min      3.1200
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             636
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15147
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.855
_diffrn_reflns_theta_min         4.964
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      210.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     26.00 119.00   0.50    0.05    --   46.83  73.00 139.00  186
  2  ω     24.00 119.00   0.50    0.05    --   46.83  77.00  60.00  190
  3  ω     32.00 118.00   0.50    0.05    --   46.83  57.00-120.00  172
  4  ω    -27.00  13.00   0.50    0.05    --   46.83 -19.00   0.00   80
  5  ω    -27.00  13.00   0.50    0.05    --   46.83 -19.00 -60.00   80
  6  ω    -25.00  68.00   0.50    0.05    --   46.83 -73.00  10.00  186
  7  ω     38.00 133.00   0.50    0.06    --  110.25 -77.00 -90.00  190
  8  ω     38.00  80.00   0.50    0.06    --  110.25 -61.00   0.00   84
  9  ω     38.00 131.00   0.50    0.06    --  110.25 -73.00  10.00  186
 10  ω     38.00  80.00   0.50    0.06    --  110.25 -61.00 150.00   84
 11  ω     38.00 106.00   0.50    0.06    --  110.25 -94.00 150.00  136
 12  ω     38.00 106.00   0.50    0.06    --  110.25 -94.00 -90.00  136
 13  ω     38.00 111.00   0.50    0.06    --  110.25-125.00-180.00  146
 14  ω     98.00 178.00   0.50    0.06    --  110.25  30.00 -90.00  160
 15  ω     98.00 178.00   0.50    0.06    --  110.25  30.00 -30.00  160
 16  ω     98.00 178.00   0.50    0.06    --  110.25  30.00-150.00  160
 17  ω     88.00 140.00   0.50    0.06    --  110.25  77.00   0.00  104
 18  ω     98.00 178.00   0.50    0.06    --  110.25  30.00  60.00  160
 19  ω     89.00 178.00   0.50    0.06    --  110.25  73.00 139.00  178
 20  ω     -5.00  29.00   0.50    0.05    --  -46.83  19.00-120.00   68
 21  ω     -5.00  29.00   0.50    0.05    --  -46.83  19.00 -60.00   68
 22  ω    -68.00  26.00   0.50    0.05    --  -46.83  73.00 139.00  188
 23  ω   -123.00 -29.00   0.50    0.06    -- -102.00  73.00 139.00  188
 24  ω    -72.00 -29.00   0.50    0.06    -- -102.00  61.00 120.00   86
 25  ω    -72.00 -29.00   0.50    0.06    -- -102.00  61.00  90.00   86
 26  ω    -72.00 -29.00   0.50    0.06    -- -102.00  61.00   0.00   86
 27  ω    -72.00 -29.00   0.50    0.06    -- -102.00  61.00 -30.00   86
 28  ω   -112.00 -29.00   0.50    0.06    -- -102.00 125.00-120.00  166
 29  ω   -118.00 -24.00   0.50    0.05    --  -46.83 -77.00 -60.00  188
 30  ω   -118.00 -24.00   0.50    0.05    --  -46.83 -77.00  30.00  188
 31  ω   -175.00 -81.00   0.50    0.06    -- -102.00 -73.00  10.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1556919000
_diffrn_orient_matrix_UB_12      -0.0289614000
_diffrn_orient_matrix_UB_13      0.0621287000
_diffrn_orient_matrix_UB_21      0.1051217000
_diffrn_orient_matrix_UB_22      -0.1048397000
_diffrn_orient_matrix_UB_23      0.0421446000
_diffrn_orient_matrix_UB_31      0.0842154000
_diffrn_orient_matrix_UB_32      0.0773318000
_diffrn_orient_matrix_UB_33      0.0803833000
_diffrn_oxdiff_digest_frames     
;
01af40cdf37c4d69c79936b26c90f38c92000410690
;
_diffrn_oxdiff_digest_hkl        
;
01b9340e8b04aa4e9960c8d3459395b68173ce
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2399
_reflns_number_total             2542
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2542
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.091
_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)+(0.0484P)²+0.7965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0881
_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:
 C2(H2), C4(H4), C7(H7), C5(H5), C13(H13), C10(H10), C11(H11), C12(H12)
;
_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
Br15 Br 0.08918(3) 0.60446(2) 0.24027(2) 0.04275(12) Uani 1 1 d . . . . .
O19 O 0.1105(2) 0.35741(15) 0.40570(11) 0.0404(4) Uani 1 1 d . . . . .
O18 O 0.4204(3) 0.11607(16) 0.77795(15) 0.0521(5) Uani 1 1 d . . . . .
N8 N 0.2162(2) 0.56686(16) 0.44802(12) 0.0310(4) Uani 1 1 d . . . . .
O17 O 0.4525(3) 0.29511(19) 0.81892(13) 0.0599(5) Uani 1 1 d . . . . .
N16 N 0.4066(2) 0.2200(2) 0.76092(13) 0.0409(5) Uani 1 1 d . . . . .
C1 C 0.2731(3) 0.40760(17) 0.55300(15) 0.0292(4) Uani 1 1 d . . . . .
C14 C 0.1753(3) 0.71778(18) 0.32929(15) 0.0312(4) Uani 1 1 d . . . . .
C2 C 0.3459(3) 0.37053(19) 0.64212(15) 0.0324(4) Uani 1 1 d . . . . .
H2 H 0.403675 0.423584 0.684578 0.039 Uiso 1 1 calc R . . . .
C9 C 0.2287(3) 0.68479(18) 0.42284(15) 0.0312(4) Uani 1 1 d . . . . .
C6 C 0.1868(3) 0.32580(19) 0.49076(15) 0.0313(4) Uani 1 1 d . . . . .
C3 C 0.3323(3) 0.25596(19) 0.66726(15) 0.0328(4) Uani 1 1 d . . . . .
C4 C 0.2515(3) 0.17439(19) 0.60554(16) 0.0364(5) Uani 1 1 d . . . . .
H4 H 0.246537 0.096202 0.623794 0.044 Uiso 1 1 calc R . . . .
C7 C 0.2877(3) 0.52820(18) 0.52717(14) 0.0314(4) Uani 1 1 d . . . . .
H7 H 0.350881 0.579270 0.569261 0.038 Uiso 1 1 calc R . . . .
C5 C 0.1792(3) 0.2091(2) 0.51777(16) 0.0374(5) Uani 1 1 d . . . . .
H5 H 0.124528 0.154445 0.475619 0.045 Uiso 1 1 calc R . . . .
C13 C 0.1829(3) 0.8317(2) 0.29971(17) 0.0384(5) Uani 1 1 d . . . . .
H13 H 0.145401 0.851765 0.236613 0.046 Uiso 1 1 calc R . . . .
C10 C 0.2874(3) 0.7721(2) 0.48624(16) 0.0386(5) Uani 1 1 d . . . . .
H10 H 0.320440 0.753130 0.550132 0.046 Uiso 1 1 calc R . . . .
C11 C 0.2979(4) 0.8856(2) 0.45679(19) 0.0431(5) Uani 1 1 d . . . . .
H11 H 0.340489 0.942816 0.500228 0.052 Uiso 1 1 calc R . . . .
C12 C 0.2459(3) 0.9160(2) 0.3633(2) 0.0423(5) Uani 1 1 d . . . . .
H12 H 0.253423 0.993460 0.343340 0.051 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
Br15 C14 1.893(2) . ?
O19 C6 1.339(3) . ?
O18 N16 1.226(3) . ?
N8 C9 1.412(3) . ?
N8 C7 1.281(3) . ?
O17 N16 1.223(3) . ?
N16 C3 1.454(3) . ?
C1 C2 1.398(3) . ?
C1 C6 1.414(3) . ?
C1 C7 1.445(3) . ?
C14 C9 1.400(3) . ?
C14 C13 1.382(3) . ?
C2 C3 1.375(3) . ?
C9 C10 1.396(3) . ?
C6 C5 1.402(3) . ?
C3 C4 1.390(3) . ?
C4 C5 1.372(3) . ?
C13 C12 1.382(4) . ?
C10 C11 1.378(3) . ?
C11 C12 1.389(4) . ?

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 N8 C9 121.49(18) . . ?
O18 N16 C3 118.6(2) . . ?
O17 N16 O18 123.2(2) . . ?
O17 N16 C3 118.2(2) . . ?
C2 C1 C6 118.90(19) . . ?
C2 C1 C7 119.22(19) . . ?
C6 C1 C7 121.88(19) . . ?
C9 C14 Br15 119.64(16) . . ?
C13 C14 Br15 118.62(16) . . ?
C13 C14 C9 121.7(2) . . ?
C3 C2 C1 119.6(2) . . ?
C14 C9 N8 118.55(18) . . ?
C10 C9 N8 124.08(19) . . ?
C10 C9 C14 117.4(2) . . ?
O19 C6 C1 121.26(19) . . ?
O19 C6 C5 118.72(19) . . ?
C5 C6 C1 120.0(2) . . ?
C2 C3 N16 118.5(2) . . ?
C2 C3 C4 121.9(2) . . ?
C4 C3 N16 119.6(2) . . ?
C5 C4 C3 119.4(2) . . ?
N8 C7 C1 121.28(19) . . ?
C4 C5 C6 120.2(2) . . ?
C14 C13 C12 119.7(2) . . ?
C11 C10 C9 121.2(2) . . ?
C10 C11 C12 120.4(2) . . ?
C13 C12 C11 119.6(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 1.483
_oxdiff_exptl_absorpt_empirical_full_min 0.630
####################################################################### 
# 
# 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_sh36_240_auto
_database_code_depnum_ccdc_archive 'CCDC 2156459'
loop_
_audit_author_name
_audit_author_address
'Frederick P. Malan'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2022-03-04 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2022-02-24
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 Br N2 O3'
_chemical_formula_sum            'C13 H8 Br N2 O3'
_chemical_formula_weight         320.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N4 O4 Br'
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      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                   7.53090(10)
_cell_length_b                   11.5580(2)
_cell_length_c                   14.0459(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.0040(10)
_cell_angle_gamma                90
_cell_volume                     1219.60(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11988
_cell_measurement_temperature    239.99(10)
_cell_measurement_theta_max      78.5830
_cell_measurement_theta_min      3.1580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.668
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             636
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14419
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.922
_diffrn_reflns_theta_min         4.960
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      239.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00 119.00   0.50    0.05    --   46.83  77.00-150.00  190
  2  ω     24.00 119.00   0.50    0.05    --   46.83  77.00 -90.00  190
  3  ω     32.00  77.00   0.50    0.05    --   46.83  57.00 -90.00   90
  4  ω     24.00 119.00   0.50    0.05    --   46.83  77.00 -30.00  190
  5  ω     24.00 119.00   0.50    0.05    --   46.83  77.00  30.00  190
  6  ω     26.00 119.00   0.50    0.05    --   46.83  74.00 138.00  186
  7  ω     32.00 118.00   0.50    0.05    --   46.83  57.00 120.00  172
  8  ω    -68.00  26.00   0.50    0.05    --  -46.83  74.00 138.00  188
  9  ω     -5.00  29.00   0.50    0.05    --  -46.83  19.00-120.00   68
 10  ω     -5.00  29.00   0.50    0.05    --  -46.83  19.00 -60.00   68
 11  ω     89.00 178.00   0.50    0.06    --  110.25  74.00 138.00  178
 12  ω     98.00 178.00   0.50    0.06    --  110.25  45.00  90.00  160
 13  ω     98.00 178.00   0.50    0.06    --  110.25  30.00  60.00  160
 14  ω     94.00 178.00   0.50    0.06    --  110.25  61.00  90.00  168
 15  ω     97.00 175.00   0.50    0.06    --  110.25  15.00  30.00  156
 16  ω     97.00 175.00   0.50    0.06    --  110.25  15.00-150.00  156
 17  ω     38.00 106.00   0.50    0.06    --  110.25 -94.00-150.00  136
 18  ω     38.00 106.00   0.50    0.06    --  110.25 -94.00-120.00  136
 19  ω     38.00 106.00   0.50    0.06    --  110.25 -94.00 -90.00  136
 20  ω     18.00  95.00   0.50    0.05    --   46.83-125.00-120.00  154
 21  ω    -25.00  68.00   0.50    0.05    --   46.83 -74.00   9.00  186
 22  ω     38.00 132.00   0.50    0.06    --  110.25 -74.00   9.00  188
 23  ω     38.00  80.00   0.50    0.06    --  110.25 -61.00  30.00   84
 24  ω     38.00  80.00   0.50    0.06    --  110.25 -61.00  90.00   84
 25  ω     38.00  80.00   0.50    0.06    --  110.25 -61.00 -90.00   84
 26  ω    -27.00  13.00   0.50    0.05    --   46.83 -19.00   0.00   80
 27  ω   -175.00 -80.00   0.50    0.06    -- -102.00 -74.00   9.00  190
 28  ω    -72.00 -29.00   0.50    0.06    -- -102.00  61.00 -60.00   86
 29  ω    -72.00 -29.00   0.50    0.06    -- -102.00  61.00   0.00   86
 30  ω   -123.00 -29.00   0.50    0.06    -- -102.00  74.00 138.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1540994000
_diffrn_orient_matrix_UB_12      -0.0302476000
_diffrn_orient_matrix_UB_13      0.0621928000
_diffrn_orient_matrix_UB_21      0.1060740000
_diffrn_orient_matrix_UB_22      -0.1047299000
_diffrn_orient_matrix_UB_23      0.0412111000
_diffrn_orient_matrix_UB_31      0.0838956000
_diffrn_orient_matrix_UB_32      0.0767327000
_diffrn_orient_matrix_UB_33      0.0807621000
_diffrn_oxdiff_digest_frames     
;
01a6bb1f70c0caca9dd5c483759d24239a00042c807
;
_diffrn_oxdiff_digest_hkl        
;
01dfa1c412f0edcac7e648371848be1bd4d2a3
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2361
_reflns_number_total             2564
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2564
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.048
_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)+(0.0581P)²+0.7367P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1033
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C4(H4), C5(H5), C10(H10), C13(H13), C12(H12), C11(H11)
2.b Idealised tetrahedral OH refined as rotating group:
 O19(H19)
;
_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
Br15 Br 0.91083(4) 0.60470(2) 0.75940(2) 0.04961(14) Uani 1 1 d . . . . .
O19 O 0.8894(3) 0.35721(17) 0.59395(12) 0.0465(4) Uani 1 1 d . . . . .
H19 H 0.880282 0.428252 0.600722 0.070 Uiso 1 1 calc GR . . . .
N8 N 0.7832(3) 0.56718(17) 0.55177(13) 0.0354(4) Uani 1 1 d . . . . .
O18 O 0.5793(3) 0.11695(19) 0.22235(18) 0.0607(6) Uani 1 1 d . . . . .
O17 O 0.5466(3) 0.2953(2) 0.18147(15) 0.0698(6) Uani 1 1 d . . . . .
N16 N 0.5932(3) 0.2204(2) 0.23931(15) 0.0476(6) Uani 1 1 d . . . . .
C1 C 0.7272(3) 0.40828(19) 0.44692(16) 0.0336(5) Uani 1 1 d . . . . .
C14 C 0.8245(3) 0.7179(2) 0.67057(16) 0.0355(5) Uani 1 1 d . . . . .
C9 C 0.7708(3) 0.6848(2) 0.57711(16) 0.0353(5) Uani 1 1 d . . . . .
C2 C 0.6538(3) 0.3709(2) 0.35795(17) 0.0369(5) Uani 1 1 d . . . . .
H2 H 0.595658 0.423786 0.315599 0.044 Uiso 1 1 calc R . . . .
C3 C 0.6671(3) 0.2565(2) 0.33270(17) 0.0380(5) Uani 1 1 d . . . . .
C7 C 0.7120(3) 0.5286(2) 0.47283(16) 0.0363(5) Uani 1 1 d . . . . .
H7 H 0.648446 0.579477 0.430833 0.044 Uiso 1 1 calc R . . . .
C6 C 0.8135(3) 0.3264(2) 0.50918(16) 0.0360(5) Uani 1 1 d . . . . .
C4 C 0.7491(3) 0.1751(2) 0.39436(18) 0.0416(5) Uani 1 1 d . . . . .
H4 H 0.754996 0.097084 0.376002 0.050 Uiso 1 1 calc R . . . .
C5 C 0.8209(3) 0.2100(2) 0.48204(19) 0.0438(5) Uani 1 1 d . . . . .
H5 H 0.875481 0.155403 0.524215 0.053 Uiso 1 1 calc R . . . .
C10 C 0.7122(4) 0.7723(2) 0.51386(19) 0.0446(6) Uani 1 1 d . . . . .
H10 H 0.679442 0.753537 0.449913 0.054 Uiso 1 1 calc R . . . .
C13 C 0.8175(3) 0.8315(2) 0.70003(19) 0.0441(6) Uani 1 1 d . . . . .
H13 H 0.855472 0.851606 0.763032 0.053 Uiso 1 1 calc R . . . .
C12 C 0.7541(4) 0.9158(2) 0.6363(2) 0.0485(6) Uani 1 1 d . . . . .
H12 H 0.746924 0.993297 0.656082 0.058 Uiso 1 1 calc R . . . .
C11 C 0.7016(4) 0.8853(2) 0.5435(2) 0.0499(7) Uani 1 1 d . . . . .
H11 H 0.658248 0.942385 0.500182 0.060 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
Br15 C14 1.892(2) . ?
O19 C6 1.333(3) . ?
N8 C9 1.410(3) . ?
N8 C7 1.278(3) . ?
O18 N16 1.222(3) . ?
O17 N16 1.223(3) . ?
N16 C3 1.451(3) . ?
C1 C2 1.399(3) . ?
C1 C7 1.444(3) . ?
C1 C6 1.416(3) . ?
C14 C9 1.400(3) . ?
C14 C13 1.379(3) . ?
C9 C10 1.397(3) . ?
C2 C3 1.374(3) . ?
C3 C4 1.393(4) . ?
C6 C5 1.401(4) . ?
C4 C5 1.371(4) . ?
C10 C11 1.376(4) . ?
C13 C12 1.386(4) . ?
C12 C11 1.381(4) . ?

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 N8 C9 121.6(2) . . ?
O18 N16 O17 123.2(2) . . ?
O18 N16 C3 118.7(3) . . ?
O17 N16 C3 118.1(2) . . ?
C2 C1 C7 119.3(2) . . ?
C2 C1 C6 118.7(2) . . ?
C6 C1 C7 122.0(2) . . ?
C9 C14 Br15 119.53(17) . . ?
C13 C14 Br15 118.64(18) . . ?
C13 C14 C9 121.8(2) . . ?
C14 C9 N8 118.7(2) . . ?
C10 C9 N8 124.1(2) . . ?
C10 C9 C14 117.1(2) . . ?
C3 C2 C1 119.8(2) . . ?
C2 C3 N16 118.7(2) . . ?
C2 C3 C4 121.8(2) . . ?
C4 C3 N16 119.5(2) . . ?
N8 C7 C1 121.3(2) . . ?
O19 C6 C1 121.5(2) . . ?
O19 C6 C5 118.5(2) . . ?
C5 C6 C1 120.0(2) . . ?
C5 C4 C3 119.3(2) . . ?
C4 C5 C6 120.4(2) . . ?
C11 C10 C9 121.2(2) . . ?
C14 C13 C12 119.7(2) . . ?
C11 C12 C13 119.5(2) . . ?
C10 C11 C12 120.6(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 5.140
_oxdiff_exptl_absorpt_empirical_full_min 0.625
####################################################################### 
# 
# 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_sh36_270_auto
_database_code_depnum_ccdc_archive 'CCDC 2156460'
loop_
_audit_author_name
_audit_author_address
'Frederick P. Malan'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2022-03-04 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2022-02-24
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 Br N2 O3'
_chemical_formula_sum            'C13 H8 Br N2 O3'
_chemical_formula_weight         320.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N4 O4 Br'
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      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                   7.5635(2)
_cell_length_b                   11.5743(3)
_cell_length_c                   14.0536(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.109(2)
_cell_angle_gamma                90
_cell_volume                     1227.12(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6458
_cell_measurement_temperature    269.99(10)
_cell_measurement_theta_max      78.2640
_cell_measurement_theta_min      3.1240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             636
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8199
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.718
_diffrn_reflns_theta_min         4.955
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      269.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    104.00 129.00   0.50    0.06    --  110.25  61.00-150.00   50
  2  ω    151.00 177.00   0.50    0.06    --  110.25  61.00-150.00   52
  3  ω     97.00 175.00   0.50    0.06    --  110.25  15.00-120.00  156
  4  ω    103.00 168.00   0.50    0.06    --  110.25  74.00 130.00  130
  5  ω     28.00 107.00   0.50    0.05    --   46.83  74.00 130.00  158
  6  ω   -100.00 -75.00   0.50    0.06    -- -102.00  74.00 130.00   50
  7  ω    -54.00 -29.00   0.50    0.06    -- -102.00  61.00 -30.00   50
  8  ω    -72.00 -41.00   0.50    0.06    -- -102.00  61.00-120.00   62
  9  ω    -72.00 -47.00   0.50    0.06    -- -102.00  61.00-150.00   50
 10  ω      4.00  29.00   0.50    0.05    --  -46.83  19.00 -90.00   50
 11  ω    -65.00 -40.00   0.50    0.05    --  -46.83  74.00 130.00   50
 12  ω    -28.00   1.00   0.50    0.05    --  -46.83  74.00 130.00   58
 13  ω     -3.00  28.00   0.50    0.05    --  -46.83  19.00 120.00   62
 14  ω     51.00  79.00   0.50    0.06    --  110.25 -61.00 -60.00   56
 15  ω     47.00  80.00   0.50    0.06    --  110.25 -61.00   0.00   66
 16  ω     38.00 131.00   0.50    0.06    --  110.25 -74.00   2.00  186
 17  ω    -23.00  68.00   0.50    0.05    --   46.83 -74.00   2.00  182
 18  ω     47.00  74.00   0.50    0.06    --  110.25 -61.00  90.00   54
 19  ω    120.00 148.00   0.50    0.06    --  110.25 125.00   0.00   56
 20  ω     80.00 109.00   0.50    0.06    --  110.25 125.00   0.00   58
 21  ω     39.00 106.00   0.50    0.06    --  110.25 -94.00-180.00  134
 22  ω     38.00 107.00   0.50    0.06    --  110.25-125.00   0.00  138
 23  ω     75.00 105.00   0.50    0.06    --  110.25 -94.00 120.00   60
 24  ω   -174.00-127.00   0.50    0.06    -- -102.00 -74.00   2.00   94
 25  ω   -174.00-124.00   0.50    0.06    -- -102.00 -45.00  60.00  100
 26  ω   -119.00 -89.00   0.50    0.06    -- -102.00 -45.00  60.00   60
 27  ω   -139.00 -90.00   0.50    0.06    -- -102.00-125.00 150.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1395374000
_diffrn_orient_matrix_UB_12      -0.0425690000
_diffrn_orient_matrix_UB_13      0.0666331000
_diffrn_orient_matrix_UB_21      0.1236800000
_diffrn_orient_matrix_UB_22      -0.0998127000
_diffrn_orient_matrix_UB_23      0.0339437000
_diffrn_orient_matrix_UB_31      0.0833727000
_diffrn_orient_matrix_UB_32      0.0770663000
_diffrn_orient_matrix_UB_33      0.0805201000
_diffrn_oxdiff_digest_frames     
;
010c4077dc9fc24d25eb512b07af4700290003883fa
;
_diffrn_oxdiff_digest_hkl        
;
01aeba4a060e8670ad432fe32e78fad5e8ab07
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2275
_reflns_number_total             2530
_reflns_odcompleteness_completeness 99.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.775
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2530
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0531P)²+0.5807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0964
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C5(H5), C4(H4), C10(H10), C13(H13), C11(H11), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O19(H19)
;
_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
Br15 Br 0.91093(4) 0.39505(2) 0.75906(2) 0.05709(14) Uani 1 1 d . . . . .
O19 O 0.8894(3) 0.64203(16) 0.59384(12) 0.0532(4) Uani 1 1 d . . . . .
H19 H 0.878020 0.572203 0.601130 0.080 Uiso 1 1 calc GR . . . .
N8 N 0.7827(3) 0.43249(16) 0.55182(13) 0.0402(4) Uani 1 1 d . . . . .
O18 O 0.5792(3) 0.88227(19) 0.22249(18) 0.0705(6) Uani 1 1 d . . . . .
O17 O 0.5461(3) 0.7041(2) 0.18194(15) 0.0796(7) Uani 1 1 d . . . . .
N16 N 0.5925(3) 0.7786(2) 0.23945(15) 0.0542(6) Uani 1 1 d . . . . .
C1 C 0.7268(3) 0.59131(19) 0.44712(16) 0.0380(5) Uani 1 1 d . . . . .
C9 C 0.7706(3) 0.31475(19) 0.57689(16) 0.0402(5) Uani 1 1 d . . . . .
C14 C 0.8245(3) 0.2820(2) 0.67020(16) 0.0408(5) Uani 1 1 d . . . . .
C2 C 0.6538(3) 0.6286(2) 0.35810(16) 0.0420(5) Uani 1 1 d . . . . .
H2 H 0.596372 0.576404 0.316149 0.050 Uiso 1 1 calc R . . . .
C7 C 0.7119(3) 0.47129(19) 0.47291(16) 0.0410(5) Uani 1 1 d . . . . .
H7 H 0.649409 0.421055 0.431226 0.049 Uiso 1 1 calc R . . . .
C6 C 0.8135(3) 0.6730(2) 0.50887(16) 0.0406(5) Uani 1 1 d . . . . .
C3 C 0.6672(3) 0.7428(2) 0.33300(16) 0.0429(5) Uani 1 1 d . . . . .
C5 C 0.8210(3) 0.7891(2) 0.48189(18) 0.0493(6) Uani 1 1 d . . . . .
H5 H 0.875203 0.842955 0.523571 0.059 Uiso 1 1 calc R . . . .
C4 C 0.7488(3) 0.8240(2) 0.39437(18) 0.0485(5) Uani 1 1 d . . . . .
H4 H 0.754395 0.901090 0.376235 0.058 Uiso 1 1 calc R . . . .
C10 C 0.7117(4) 0.2278(2) 0.51396(19) 0.0511(6) Uani 1 1 d . . . . .
H10 H 0.678539 0.246330 0.450796 0.061 Uiso 1 1 calc R . . . .
C13 C 0.8176(4) 0.1684(2) 0.69970(18) 0.0506(6) Uani 1 1 d . . . . .
H13 H 0.855149 0.148470 0.761997 0.061 Uiso 1 1 calc R . . . .
C11 C 0.7018(4) 0.1145(2) 0.5438(2) 0.0570(7) Uani 1 1 d . . . . .
H11 H 0.659115 0.058017 0.501065 0.068 Uiso 1 1 calc R . . . .
C12 C 0.7544(4) 0.0845(2) 0.6360(2) 0.0556(6) Uani 1 1 d . . . . .
H12 H 0.747514 0.007917 0.655516 0.067 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
Br15 C14 1.893(2) . ?
O19 C6 1.336(3) . ?
N8 C9 1.412(3) . ?
N8 C7 1.278(3) . ?
O18 N16 1.226(3) . ?
O17 N16 1.216(3) . ?
N16 C3 1.454(3) . ?
C1 C2 1.399(3) . ?
C1 C7 1.442(3) . ?
C1 C6 1.412(3) . ?
C9 C14 1.397(3) . ?
C9 C10 1.392(3) . ?
C14 C13 1.381(3) . ?
C2 C3 1.374(3) . ?
C6 C5 1.399(3) . ?
C3 C4 1.389(4) . ?
C5 C4 1.370(4) . ?
C10 C11 1.381(4) . ?
C13 C12 1.383(4) . ?
C11 C12 1.372(4) . ?

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 N8 C9 121.7(2) . . ?
O18 N16 C3 118.4(2) . . ?
O17 N16 O18 123.3(2) . . ?
O17 N16 C3 118.3(2) . . ?
C2 C1 C7 119.3(2) . . ?
C2 C1 C6 118.6(2) . . ?
C6 C1 C7 122.1(2) . . ?
C14 C9 N8 118.4(2) . . ?
C10 C9 N8 124.2(2) . . ?
C10 C9 C14 117.3(2) . . ?
C9 C14 Br15 119.70(17) . . ?
C13 C14 Br15 118.62(18) . . ?
C13 C14 C9 121.7(2) . . ?
C3 C2 C1 119.7(2) . . ?
N8 C7 C1 121.4(2) . . ?
O19 C6 C1 121.4(2) . . ?
O19 C6 C5 118.5(2) . . ?
C5 C6 C1 120.2(2) . . ?
C2 C3 N16 118.4(2) . . ?
C2 C3 C4 121.9(2) . . ?
C4 C3 N16 119.7(2) . . ?
C4 C5 C6 120.3(2) . . ?
C5 C4 C3 119.3(2) . . ?
C11 C10 C9 121.0(2) . . ?
C14 C13 C12 119.6(2) . . ?
C12 C11 C10 120.6(3) . . ?
C11 C12 C13 119.8(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 2.036
_oxdiff_exptl_absorpt_empirical_full_min 0.602
####################################################################### 
# 
# 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_sh36_300b_auto
_database_code_depnum_ccdc_archive 'CCDC 2156461'
loop_
_audit_author_name
_audit_author_address
'Frederick P. Malan'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2022-03-04 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2022-02-25
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 Br N2 O3'
_chemical_formula_sum            'C13 H8 Br N2 O3'
_chemical_formula_weight         320.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N4 O4 Br'
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      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                   7.59950(10)
_cell_length_b                   11.5868(2)
_cell_length_c                   14.0731(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.2470(10)
_cell_angle_gamma                90
_cell_volume                     1235.79(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12463
_cell_measurement_temperature    299.95(13)
_cell_measurement_theta_max      78.5800
_cell_measurement_theta_min      3.1410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.607
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             636
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15577
_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         78.657
_diffrn_reflns_theta_min         4.950
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.95(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_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     30.00 119.00   0.50    0.05    --   46.83  63.00-104.00  178
  2  ω     24.00 119.00   0.50    0.05    --   46.83  77.00 -60.00  190
  3  ω     24.00 119.00   0.50    0.05    --   46.83  77.00  30.00  190
  4  ω     24.00 119.00   0.50    0.05    --   46.83  77.00 150.00  190
  5  ω    -64.00  26.00   0.50    0.05    --  -46.83  63.00-104.00  180
  6  ω     -5.00  29.00   0.50    0.05    --  -46.83  19.00  30.00   68
  7  ω     -5.00  29.00   0.50    0.05    --  -46.83  19.00-120.00   68
  8  ω     -5.00  29.00   0.50    0.05    --  -46.83  19.00-150.00   68
  9  ω     93.00 178.00   0.50    0.07    --  110.25  63.00-104.00  170
 10  ω     94.00 178.00   0.50    0.07    --  110.25  61.00-180.00  168
 11  ω     98.00 178.00   0.50    0.07    --  110.25  45.00-150.00  160
 12  ω     97.00 175.00   0.50    0.07    --  110.25  15.00-180.00  156
 13  ω     98.00 178.00   0.50    0.07    --  110.25  45.00 -60.00  160
 14  ω     98.00 178.00   0.50    0.07    --  110.25  30.00  90.00  160
 15  ω     38.00 106.00   0.50    0.07    --  110.25 -94.00 -90.00  136
 16  ω     38.00 106.00   0.50    0.07    --  110.25 -94.00-180.00  136
 17  ω     18.00  95.00   0.50    0.05    --   46.83-125.00 -30.00  154
 18  ω     38.00 106.00   0.50    0.07    --  110.25 -94.00   0.00  136
 19  ω     38.00  80.00   0.50    0.07    --  110.25 -61.00  60.00   84
 20  ω     38.00  85.00   0.50    0.07    --  110.25 -63.00 119.00   94
 21  ω     38.00 133.00   0.50    0.07    --  110.25 -77.00   0.00  190
 22  ω     38.00  80.00   0.50    0.07    --  110.25 -61.00 -90.00   84
 23  ω     38.00  80.00   0.50    0.07    --  110.25 -61.00   0.00   84
 24  ω    -25.00  64.00   0.50    0.05    --   46.83 -63.00 119.00  178
 25  ω   -175.00-110.00   0.50    0.07    -- -102.00 -77.00  90.00  130
 26  ω   -118.00 -30.00   0.50    0.05    --  -46.83 -63.00 119.00  176
 27  ω   -175.00 -85.00   0.50    0.07    -- -102.00 -63.00 119.00  180
 28  ω   -167.00 -88.00   0.50    0.07    -- -102.00 -15.00   0.00  158
 29  ω    -77.00 -29.00   0.50    0.07    -- -102.00  63.00-104.00   96
 30  ω    -72.00 -29.00   0.50    0.07    -- -102.00  61.00  30.00   86
 31  ω    -72.00 -29.00   0.50    0.07    -- -102.00  61.00  60.00   86
 32  ω    -72.00 -29.00   0.50    0.07    -- -102.00  61.00  90.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0971505000
_diffrn_orient_matrix_UB_12      0.0960874000
_diffrn_orient_matrix_UB_13      0.0507843000
_diffrn_orient_matrix_UB_21      0.1627433000
_diffrn_orient_matrix_UB_22      0.0165617000
_diffrn_orient_matrix_UB_23      0.0706498000
_diffrn_orient_matrix_UB_31      0.0733924000
_diffrn_orient_matrix_UB_32      0.0903984000
_diffrn_orient_matrix_UB_33      -0.0669445000
_diffrn_oxdiff_digest_frames     
;
010f92fff3b06126a72b392c26ce056799000473cfb
;
_diffrn_oxdiff_digest_hkl        
;
01db5c8e36fff3d65d3be19ddd639682f72558
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2372
_reflns_number_total             2596
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.801
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2596
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.077
_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)+(0.0576P)²+0.4774P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1046
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2), C5(H5), C10(H10), C4(H4), C13(H13), C11(H11), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O19(H19)
;
_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
Br15 Br 0.91098(4) 0.39476(2) 0.75870(2) 0.06709(15) Uani 1 1 d . . . . .
O19 O 0.8893(3) 0.64120(16) 0.59343(12) 0.0632(4) Uani 1 1 d . . . . .
H19 H 0.876164 0.571678 0.601168 0.095 Uiso 1 1 calc GR . . . .
N8 N 0.7821(2) 0.43221(16) 0.55166(12) 0.0474(4) Uani 1 1 d . . . . .
O18 O 0.5792(3) 0.8812(2) 0.22261(18) 0.0825(7) Uani 1 1 d . . . . .
O17 O 0.5454(4) 0.7035(2) 0.18215(16) 0.0930(7) Uani 1 1 d . . . . .
N16 N 0.5926(3) 0.7784(2) 0.23978(15) 0.0641(6) Uani 1 1 d . . . . .
C9 C 0.7701(3) 0.31477(19) 0.57673(15) 0.0469(4) Uani 1 1 d . . . . .
C1 C 0.7265(3) 0.59064(18) 0.44694(15) 0.0444(4) Uani 1 1 d . . . . .
C14 C 0.8243(3) 0.28193(19) 0.66980(15) 0.0483(5) Uani 1 1 d . . . . .
C6 C 0.8134(3) 0.67207(19) 0.50888(16) 0.0483(5) Uani 1 1 d . . . . .
C3 C 0.6671(3) 0.7420(2) 0.33313(16) 0.0505(5) Uani 1 1 d . . . . .
C7 C 0.7117(3) 0.47069(19) 0.47282(15) 0.0482(5) Uani 1 1 d . . . . .
H7 H 0.649589 0.420401 0.431168 0.058 Uiso 1 1 calc R . . . .
C2 C 0.6536(3) 0.6280(2) 0.35816(16) 0.0500(5) Uani 1 1 d . . . . .
H2 H 0.596154 0.575861 0.316231 0.060 Uiso 1 1 calc R . . . .
C5 C 0.8213(3) 0.7882(2) 0.48169(18) 0.0587(6) Uani 1 1 d . . . . .
H5 H 0.875796 0.842015 0.523149 0.070 Uiso 1 1 calc R . . . .
C10 C 0.7114(4) 0.2276(2) 0.51388(18) 0.0600(6) Uani 1 1 d . . . . .
H10 H 0.678285 0.245980 0.450736 0.072 Uiso 1 1 calc R . . . .
C4 C 0.7491(3) 0.8226(2) 0.39410(18) 0.0571(6) Uani 1 1 d . . . . .
H4 H 0.755053 0.899573 0.375774 0.069 Uiso 1 1 calc R . . . .
C13 C 0.8179(4) 0.1684(2) 0.69933(19) 0.0596(6) Uani 1 1 d . . . . .
H13 H 0.856221 0.148411 0.761450 0.071 Uiso 1 1 calc R . . . .
C11 C 0.7016(4) 0.1149(2) 0.5437(2) 0.0673(7) Uani 1 1 d . . . . .
H11 H 0.658810 0.058463 0.501069 0.081 Uiso 1 1 calc R . . . .
C12 C 0.7543(4) 0.0849(2) 0.6358(2) 0.0650(7) Uani 1 1 d . . . . .
H12 H 0.747121 0.008476 0.655400 0.078 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
Br15 C14 1.894(2) . ?
O19 C6 1.332(3) . ?
N8 C9 1.410(3) . ?
N8 C7 1.276(3) . ?
O18 N16 1.219(3) . ?
O17 N16 1.223(3) . ?
N16 C3 1.454(3) . ?
C9 C14 1.397(3) . ?
C9 C10 1.394(3) . ?
C1 C6 1.415(3) . ?
C1 C7 1.443(3) . ?
C1 C2 1.397(3) . ?
C14 C13 1.382(3) . ?
C6 C5 1.401(3) . ?
C3 C2 1.373(3) . ?
C3 C4 1.385(4) . ?
C5 C4 1.371(4) . ?
C10 C11 1.376(4) . ?
C13 C12 1.380(4) . ?
C11 C12 1.373(4) . ?

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 N8 C9 121.60(19) . . ?
O18 N16 O17 123.1(2) . . ?
O18 N16 C3 118.9(3) . . ?
O17 N16 C3 118.0(2) . . ?
C14 C9 N8 118.51(19) . . ?
C10 C9 N8 124.3(2) . . ?
C10 C9 C14 117.1(2) . . ?
C6 C1 C7 121.9(2) . . ?
C2 C1 C6 118.7(2) . . ?
C2 C1 C7 119.4(2) . . ?
C9 C14 Br15 119.71(17) . . ?
C13 C14 Br15 118.48(18) . . ?
C13 C14 C9 121.8(2) . . ?
O19 C6 C1 121.5(2) . . ?
O19 C6 C5 118.5(2) . . ?
C5 C6 C1 120.0(2) . . ?
C2 C3 N16 118.6(2) . . ?
C2 C3 C4 121.9(2) . . ?
C4 C3 N16 119.4(2) . . ?
N8 C7 C1 121.4(2) . . ?
C3 C2 C1 119.7(2) . . ?
C4 C5 C6 120.2(2) . . ?
C11 C10 C9 121.1(2) . . ?
C5 C4 C3 119.5(2) . . ?
C12 C13 C14 119.4(2) . . ?
C12 C11 C10 120.7(3) . . ?
C11 C12 C13 119.8(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 1.877
_oxdiff_exptl_absorpt_empirical_full_min 0.688
####################################################################### 
# 
# 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_sh36_180_auto
_database_code_depnum_ccdc_archive 'CCDC 2156457'
loop_
_audit_author_name
_audit_author_address
'Frederick P. Malan'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2022-03-04 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2022-02-24
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 Br N2 O3'
_chemical_formula_sum            'C13 H8 Br N2 O3'
_chemical_formula_weight         320.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N4 O4 Br'
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      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                   7.46880(10)
_cell_length_b                   11.5368(2)
_cell_length_c                   14.0272(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.7640(10)
_cell_angle_gamma                90
_cell_volume                     1206.06(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12302
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      78.5320
_cell_measurement_theta_min      3.2910
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.720
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             636
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14426
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.820
_diffrn_reflns_theta_min         4.968
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     26.00 119.00   0.50    0.05    --   46.83  72.00 140.00  186
  2  ω     24.00 119.00   0.50    0.05    --   46.83  77.00 -30.00  190
  3  ω     32.00 118.00   0.50    0.05    --   46.83  57.00 -90.00  172
  4  ω    -27.00  13.00   0.50    0.05    --   46.83 -19.00-150.00   80
  5  ω    -27.00  13.00   0.50    0.05    --   46.83 -19.00   0.00   80
  6  ω    -27.00  13.00   0.50    0.05    --   46.83 -19.00  30.00   80
  7  ω    -25.00  68.00   0.50    0.05    --   46.83 -72.00  10.00  186
  8  ω     38.00 111.00   0.50    0.06    --  110.25-125.00 -90.00  146
  9  ω     38.00 106.00   0.50    0.06    --  110.25 -94.00-120.00  136
 10  ω     38.00 106.00   0.50    0.06    --  110.25 -94.00 -90.00  136
 11  ω     38.00 106.00   0.50    0.06    --  110.25 -94.00 -30.00  136
 12  ω     38.00  80.00   0.50    0.06    --  110.25 -61.00 -90.00   84
 13  ω     38.00 131.00   0.50    0.06    --  110.25 -72.00  10.00  186
 14  ω     97.00 175.00   0.50    0.06    --  110.25  15.00-120.00  156
 15  ω     88.00 178.00   0.50    0.06    --  110.25  77.00  60.00  180
 16  ω     90.00 178.00   0.50    0.06    --  110.25  72.00 140.00  176
 17  ω     98.00 178.00   0.50    0.06    --  110.25  45.00 120.00  160
 18  ω     94.00 178.00   0.50    0.06    --  110.25  61.00  90.00  168
 19  ω     98.00 178.00   0.50    0.06    --  110.25  45.00  60.00  160
 20  ω    -67.00  26.00   0.50    0.05    --  -46.83  72.00 140.00  186
 21  ω   -123.00 -29.00   0.50    0.06    -- -102.00  72.00 140.00  188
 22  ω    -72.00 -29.00   0.50    0.06    -- -102.00  61.00   0.00   86
 23  ω     -5.00  29.00   0.50    0.05    --  -46.83  19.00 -60.00   68
 24  ω    -72.00 -29.00   0.50    0.06    -- -102.00  61.00 -60.00   86
 25  ω   -175.00 -81.00   0.50    0.06    -- -102.00 -72.00  10.00  188
 26  ω   -118.00 -24.00   0.50    0.05    --  -46.83 -77.00  30.00  188
 27  ω   -175.00 -84.00   0.50    0.06    -- -102.00 -94.00  60.00  182
 28  ω   -175.00 -74.00   0.50    0.06    -- -102.00-125.00-150.00  202
 29  ω   -118.00 -24.00   0.50    0.05    --  -46.83 -77.00-180.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1573356000
_diffrn_orient_matrix_UB_12      -0.0270858000
_diffrn_orient_matrix_UB_13      0.0621299000
_diffrn_orient_matrix_UB_21      0.1041978000
_diffrn_orient_matrix_UB_22      -0.1046196000
_diffrn_orient_matrix_UB_23      0.0437266000
_diffrn_orient_matrix_UB_31      0.0841759000
_diffrn_orient_matrix_UB_32      0.0785049000
_diffrn_orient_matrix_UB_33      0.0796464000
_diffrn_oxdiff_digest_frames     
;
018a3de4632df2973ae0cfdc3079a10bc1000394e6d
;
_diffrn_oxdiff_digest_hkl        
;
0178967e321f20073e684191efed20a017485e
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2390
_reflns_number_total             2529
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.790
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2529
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.085
_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)+(0.0589P)²+1.1339P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1034
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C7(H7), C5(H5), C13(H13), C10(H10), C11(H11), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O19(H19)
;
_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
Br15 Br 0.91075(4) 0.39579(2) 0.76004(2) 0.03593(13) Uani 1 1 d . . . . .
O19 O 0.8893(3) 0.64388(16) 0.59462(12) 0.0335(4) Uani 1 1 d . . . . .
H19 H 0.875406 0.572391 0.602714 0.050 Uiso 1 1 calc GR . . . .
O18 O 0.5796(3) 0.88477(18) 0.22183(17) 0.0438(5) Uani 1 1 d . . . . .
O17 O 0.5480(3) 0.7054(2) 0.18056(15) 0.0509(6) Uani 1 1 d . . . . .
N8 N 0.7842(3) 0.43339(18) 0.55215(14) 0.0260(4) Uani 1 1 d . . . . .
N16 N 0.5934(3) 0.7808(2) 0.23902(15) 0.0342(5) Uani 1 1 d . . . . .
C1 C 0.7270(3) 0.5929(2) 0.44684(18) 0.0255(5) Uani 1 1 d . . . . .
C14 C 0.8249(3) 0.2823(2) 0.67097(17) 0.0271(5) Uani 1 1 d . . . . .
C2 C 0.6543(3) 0.6296(2) 0.35772(18) 0.0277(5) Uani 1 1 d . . . . .
H2 H 0.596077 0.575815 0.314733 0.033 Uiso 1 1 calc R . . . .
C9 C 0.7715(3) 0.3153(2) 0.57732(17) 0.0260(5) Uani 1 1 d . . . . .
C6 C 0.8129(3) 0.6749(2) 0.50913(17) 0.0267(5) Uani 1 1 d . . . . .
C3 C 0.6678(3) 0.7446(2) 0.33279(17) 0.0276(5) Uani 1 1 d . . . . .
C4 C 0.7484(3) 0.8267(2) 0.39448(18) 0.0307(5) Uani 1 1 d . . . . .
H4 H 0.753494 0.905792 0.375931 0.037 Uiso 1 1 calc R . . . .
C7 C 0.7122(3) 0.4720(2) 0.47273(17) 0.0269(5) Uani 1 1 d . . . . .
H7 H 0.648081 0.420278 0.430252 0.032 Uiso 1 1 calc R . . . .
C5 C 0.8206(4) 0.7919(2) 0.48252(19) 0.0324(5) Uani 1 1 d . . . . .
H5 H 0.875673 0.847082 0.525327 0.039 Uiso 1 1 calc R . . . .
C13 C 0.8168(4) 0.1680(2) 0.70032(19) 0.0326(5) Uani 1 1 d . . . . .
H13 H 0.854711 0.147575 0.764076 0.039 Uiso 1 1 calc R . . . .
C10 C 0.7130(4) 0.2280(2) 0.51373(19) 0.0331(5) Uani 1 1 d . . . . .
H10 H 0.680046 0.247318 0.449099 0.040 Uiso 1 1 calc R . . . .
C11 C 0.7021(4) 0.1141(2) 0.5431(2) 0.0365(6) Uani 1 1 d . . . . .
H11 H 0.659232 0.056289 0.499087 0.044 Uiso 1 1 calc R . . . .
C12 C 0.7534(4) 0.0836(2) 0.6367(2) 0.0359(6) Uani 1 1 d . . . . .
H12 H 0.745018 0.005333 0.656884 0.043 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
Br15 C14 1.892(2) . ?
O19 C6 1.342(3) . ?
O18 N16 1.227(3) . ?
O17 N16 1.228(3) . ?
N8 C9 1.412(3) . ?
N8 C7 1.285(3) . ?
N16 C3 1.455(3) . ?
C1 C2 1.396(3) . ?
C1 C6 1.413(3) . ?
C1 C7 1.448(3) . ?
C14 C9 1.400(3) . ?
C14 C13 1.384(3) . ?
C2 C3 1.378(3) . ?
C9 C10 1.396(3) . ?
C6 C5 1.403(3) . ?
C3 C4 1.393(4) . ?
C4 C5 1.375(4) . ?
C13 C12 1.383(4) . ?
C10 C11 1.382(4) . ?
C11 C12 1.388(4) . ?

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 N8 C9 121.3(2) . . ?
O18 N16 O17 123.1(2) . . ?
O18 N16 C3 118.7(2) . . ?
O17 N16 C3 118.2(2) . . ?
C2 C1 C6 119.0(2) . . ?
C2 C1 C7 119.0(2) . . ?
C6 C1 C7 121.9(2) . . ?
C9 C14 Br15 119.65(18) . . ?
C13 C14 Br15 118.83(19) . . ?
C13 C14 C9 121.5(2) . . ?
C3 C2 C1 119.2(2) . . ?
C14 C9 N8 118.5(2) . . ?
C10 C9 N8 124.0(2) . . ?
C10 C9 C14 117.5(2) . . ?
O19 C6 C1 121.5(2) . . ?
O19 C6 C5 118.1(2) . . ?
C5 C6 C1 120.3(2) . . ?
C2 C3 N16 118.4(2) . . ?
C2 C3 C4 122.2(2) . . ?
C4 C3 N16 119.4(2) . . ?
C5 C4 C3 119.2(2) . . ?
N8 C7 C1 121.1(2) . . ?
C4 C5 C6 120.0(2) . . ?
C12 C13 C14 119.9(2) . . ?
C11 C10 C9 121.2(3) . . ?
C10 C11 C12 120.3(3) . . ?
C13 C12 C11 119.6(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 5.490
_oxdiff_exptl_absorpt_empirical_full_min 0.615
####################################################################### 
# 
# 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_sh37_180_auto
_database_code_depnum_ccdc_archive 'CCDC 2156463'
loop_
_audit_author_name
_audit_author_address
'Frederick P. Malan'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2022-03-04 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2022-02-25
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 Cl N2 O3'
_chemical_formula_sum            'C13 H8 Cl N2 O3'
_chemical_formula_weight         275.66
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N4 O4 Cl'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.6708(2)
_cell_length_b                   3.74710(10)
_cell_length_c                   21.4612(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.028(2)
_cell_angle_gamma                90
_cell_volume                     1179.05(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8798
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      78.6400
_cell_measurement_theta_min      3.0180
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.942
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             564
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12250
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.916
_diffrn_reflns_theta_min         3.591
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00 118.00   0.50    0.06    --   46.83  57.00 150.00  172
  2  ω     24.00 119.00   0.50    0.06    --   46.83  77.00  60.00  190
  3  ω     34.00 121.00   0.50    0.06    --   46.83  18.00 -11.00  174
  4  ω     24.00 119.00   0.50    0.06    --   46.83  77.00 -30.00  190
  5  ω     24.00 119.00   0.50    0.06    --   46.83  77.00-150.00  190
  6  ω     79.00 178.00   0.50    0.25    --  110.25 125.00-120.00  198
  7  ω    -27.00  11.00   0.50    0.06    --   46.83 -18.00-179.00   76
  8  ω    -27.00  13.00   0.50    0.06    --   46.83 -19.00-150.00   80
  9  ω    -26.00  41.00   0.50    0.06    --   46.83 -37.00  30.00  134
 10  ω     38.00 133.00   0.50    0.25    --  110.25 -77.00  30.00  190
 11  ω     38.00  80.00   0.50    0.25    --  110.25 -61.00 120.00   84
 12  ω     38.00  80.00   0.50    0.25    --  110.25 -61.00 -30.00   84
 13  ω     38.00  80.00   0.50    0.25    --  110.25 -61.00-120.00   84
 14  ω     38.00 106.00   0.50    0.25    --  110.25 -94.00-120.00  136
 15  ω     38.00 111.00   0.50    0.25    --  110.25-125.00-180.00  146
 16  ω     38.00 106.00   0.50    0.25    --  110.25 -94.00 -90.00  136
 17  ω     18.00  95.00   0.50    0.06    --   46.83-125.00-150.00  154
 18  ω     18.00  95.00   0.50    0.06    --   46.83-125.00 -60.00  154
 19  ω     38.00 106.00   0.50    0.25    --  110.25 -94.00  30.00  136
 20  ω     97.00 175.00   0.50    0.25    --  110.25  15.00-120.00  156
 21  ω     94.00 178.00   0.50    0.25    --  110.25  61.00  60.00  168
 22  ω     97.00 178.00   0.50    0.25    --  110.25  18.00 -11.00  162
 23  ω     -3.00  29.00   0.50    0.06    --  -46.83  18.00 -11.00   64
 24  ω    -72.00 -29.00   0.50    0.25    -- -102.00  61.00  30.00   86
 25  ω   -112.00 -29.00   0.50    0.25    -- -102.00 125.00   0.00  166
 26  ω   -171.00 -89.00   0.50    0.25    -- -102.00 -18.00-179.00  164
 27  ω   -175.00 -89.00   0.50    0.25    -- -102.00 -30.00 -90.00  172
 28  ω   -121.00 -34.00   0.50    0.06    --  -46.83 -18.00-179.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0172330000
_diffrn_orient_matrix_UB_12      -0.0094260000
_diffrn_orient_matrix_UB_13      0.0712130000
_diffrn_orient_matrix_UB_21      -0.1008448000
_diffrn_orient_matrix_UB_22      -0.0960394000
_diffrn_orient_matrix_UB_23      0.0086575000
_diffrn_orient_matrix_UB_31      0.0238411000
_diffrn_orient_matrix_UB_32      -0.3997133000
_diffrn_orient_matrix_UB_33      -0.0037510000
_diffrn_oxdiff_digest_frames     
;
018968c2f9e1263f7ba0d6c034564aa484000411ae7
;
_diffrn_oxdiff_digest_hkl        
;
01469c2c70a03d670002a475b549e499e45745
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2270
_reflns_number_total             2475
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2475
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.078
_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)+(0.0523P)²+0.5421P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1030
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C14(H14), C7(H7), C10(H10), C4(H4), C5(H5), C12(H12), C11(H11)
2.b Idealised tetrahedral OH refined as rotating group:
 O19(H19)
;
_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
Cl15 Cl 0.52653(3) 0.35970(13) 0.07107(2) 0.03973(15) Uani 1 1 d . . . . .
O19 O 0.24249(8) 0.2775(4) 0.32058(5) 0.0353(3) Uani 1 1 d . . . . .
H19 H 0.288573 0.258978 0.298665 0.053 Uiso 1 1 calc GR . . . .
O18 O 0.41506(8) 0.9646(4) 0.56180(5) 0.0417(3) Uani 1 1 d . . . . .
O17 O 0.27607(9) 0.9046(4) 0.58932(6) 0.0488(4) Uani 1 1 d . . . . .
N8 N 0.41327(9) 0.3209(3) 0.29302(6) 0.0269(3) Uani 1 1 d . . . . .
N16 N 0.33584(9) 0.8678(4) 0.55138(6) 0.0305(3) Uani 1 1 d . . . . .
C2 C 0.38027(10) 0.6569(4) 0.44919(7) 0.0260(3) Uani 1 1 d . . . . .
H2 H 0.441355 0.723166 0.459841 0.031 Uiso 1 1 calc R . . . .
C14 C 0.47171(10) 0.3224(4) 0.18973(7) 0.0267(3) Uani 1 1 d . . . . .
H14 H 0.414642 0.410824 0.174158 0.032 Uiso 1 1 calc R . . . .
C1 C 0.35867(10) 0.5107(4) 0.39107(7) 0.0251(3) Uani 1 1 d . . . . .
C3 C 0.31243(10) 0.7055(4) 0.49149(7) 0.0259(3) Uani 1 1 d . . . . .
C9 C 0.48658(10) 0.2534(4) 0.25297(7) 0.0258(3) Uani 1 1 d . . . . .
C7 C 0.43082(10) 0.4532(4) 0.34719(7) 0.0263(3) Uani 1 1 d . . . . .
H7 H 0.491853 0.514830 0.358932 0.032 Uiso 1 1 calc R . . . .
C10 C 0.56922(10) 0.1133(4) 0.27527(7) 0.0284(3) Uani 1 1 d . . . . .
H10 H 0.578778 0.065129 0.318472 0.034 Uiso 1 1 calc R . . . .
C6 C 0.26705(10) 0.4157(4) 0.37595(7) 0.0272(3) Uani 1 1 d . . . . .
C4 C 0.22211(10) 0.6098(4) 0.47738(7) 0.0293(3) Uani 1 1 d . . . . .
H4 H 0.176460 0.644313 0.507105 0.035 Uiso 1 1 calc R . . . .
C13 C 0.54244(11) 0.2587(4) 0.15009(7) 0.0286(3) Uani 1 1 d . . . . .
C5 C 0.19998(10) 0.4651(4) 0.42003(8) 0.0307(3) Uani 1 1 d . . . . .
H5 H 0.138719 0.397859 0.410172 0.037 Uiso 1 1 calc R . . . .
C12 C 0.62523(11) 0.1183(4) 0.17081(8) 0.0314(3) Uani 1 1 d . . . . .
H12 H 0.672369 0.073683 0.142598 0.038 Uiso 1 1 calc R . . . .
C11 C 0.63766(10) 0.0442(4) 0.23384(8) 0.0310(3) Uani 1 1 d . . . . .
H11 H 0.693793 -0.055138 0.248894 0.037 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
Cl15 C13 1.7451(16) . ?
O19 C6 1.3342(19) . ?
O18 N16 1.2303(18) . ?
O17 N16 1.2255(18) . ?
N8 C9 1.4231(19) . ?
N8 C7 1.281(2) . ?
N16 C3 1.452(2) . ?
C2 C1 1.389(2) . ?
C2 C3 1.383(2) . ?
C14 C9 1.391(2) . ?
C14 C13 1.386(2) . ?
C1 C7 1.458(2) . ?
C1 C6 1.417(2) . ?
C3 C4 1.396(2) . ?
C9 C10 1.391(2) . ?
C10 C11 1.389(2) . ?
C6 C5 1.401(2) . ?
C4 C5 1.373(2) . ?
C13 C12 1.383(2) . ?
C12 C11 1.386(2) . ?

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 N8 C9 119.00(13) . . ?
O18 N16 C3 118.47(13) . . ?
O17 N16 O18 122.66(14) . . ?
O17 N16 C3 118.87(13) . . ?
C3 C2 C1 119.68(13) . . ?
C13 C14 C9 118.15(14) . . ?
C2 C1 C7 119.40(13) . . ?
C2 C1 C6 119.29(13) . . ?
C6 C1 C7 121.31(14) . . ?
C2 C3 N16 118.89(13) . . ?
C2 C3 C4 121.57(14) . . ?
C4 C3 N16 119.52(13) . . ?
C14 C9 N8 117.41(13) . . ?
C10 C9 N8 121.84(13) . . ?
C10 C9 C14 120.72(14) . . ?
N8 C7 C1 121.07(14) . . ?
C11 C10 C9 119.41(14) . . ?
O19 C6 C1 121.71(14) . . ?
O19 C6 C5 118.59(13) . . ?
C5 C6 C1 119.69(14) . . ?
C5 C4 C3 119.24(14) . . ?
C14 C13 Cl15 118.81(12) . . ?
C12 C13 Cl15 118.74(12) . . ?
C12 C13 C14 122.45(14) . . ?
C4 C5 C6 120.52(14) . . ?
C13 C12 C11 118.27(14) . . ?
C12 C11 C10 120.95(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.553
_oxdiff_exptl_absorpt_empirical_full_min 0.608
####################################################################### 
# 
# 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_sh37_150b_auto
_database_code_depnum_ccdc_archive 'CCDC 2156462'
loop_
_audit_author_name
_audit_author_address
'Frederick P. Malan'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2022-03-04 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2022-02-25
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 Cl N2 O3'
_chemical_formula_sum            'C13 H8 Cl N2 O3'
_chemical_formula_weight         275.66
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N4 O4 Cl'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.6564(3)
_cell_length_b                   3.73740(10)
_cell_length_c                   21.4431(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.109(2)
_cell_angle_gamma                90
_cell_volume                     1173.79(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8482
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      78.2230
_cell_measurement_theta_min      3.5600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.955
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             564
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11943
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.361
_diffrn_reflns_theta_min         3.592
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00 121.00   0.50    0.06    --   46.83  17.00  -9.00  174
  2  ω     24.00 119.00   0.50    0.06    --   46.83  77.00  60.00  190
  3  ω     24.00 119.00   0.50    0.06    --   46.83  77.00 -30.00  190
  4  ω     24.00  82.00   0.50    0.06    --   46.83  77.00-120.00  116
  5  ω    -27.00   9.00   0.50    0.06    --   46.83 -17.00-178.00   72
  6  ω    -25.00  70.00   0.50    0.06    --   46.83 -77.00 -90.00  190
  7  ω    -27.00  13.00   0.50    0.06    --   46.83 -19.00  30.00   80
  8  ω    -26.00  41.00   0.50    0.06    --   46.83 -37.00  60.00  134
  9  ω     79.00 178.00   0.50    0.23    --  110.25 125.00-180.00  198
 10  ω     38.00 106.00   0.50    0.23    --  110.25 -94.00 120.00  136
 11  ω     38.00 111.00   0.50    0.23    --  110.25-125.00  90.00  146
 12  ω     38.00 106.00   0.50    0.23    --  110.25 -94.00  90.00  136
 13  ω     38.00  80.00   0.50    0.23    --  110.25 -61.00 120.00   84
 14  ω     38.00  80.00   0.50    0.23    --  110.25 -61.00  90.00   84
 15  ω     38.00  80.00   0.50    0.23    --  110.25 -61.00  60.00   84
 16  ω     38.00  80.00   0.50    0.23    --  110.25 -61.00 -30.00   84
 17  ω     97.00 175.00   0.50    0.23    --  110.25  15.00 120.00  156
 18  ω     97.00 178.00   0.50    0.23    --  110.25  17.00  -9.00  162
 19  ω     94.00 178.00   0.50    0.23    --  110.25  61.00 -90.00  168
 20  ω     98.00 178.00   0.50    0.23    --  110.25  30.00-120.00  160
 21  ω     -1.00  29.00   0.50    0.06    --  -46.83  17.00  -9.00   60
 22  ω    -32.00  26.00   0.50    0.06    --  -46.83  37.00 120.00  116
 23  ω    -72.00 -29.00   0.50    0.23    -- -102.00  61.00  60.00   86
 24  ω    -72.00 -29.00   0.50    0.23    -- -102.00  61.00  30.00   86
 25  ω    -72.00 -29.00   0.50    0.23    -- -102.00  61.00 -60.00   86
 26  ω   -112.00 -29.00   0.50    0.23    -- -102.00 125.00   0.00  166
 27  ω   -121.00 -34.00   0.50    0.06    --  -46.83 -17.00-178.00  174
 28  ω   -170.00 -89.00   0.50    0.23    -- -102.00 -17.00-178.00  162
 29  ω   -167.00 -88.00   0.50    0.23    -- -102.00 -15.00-120.00  158
 30  ω   -120.00 -34.00   0.50    0.06    --  -46.83 -37.00 150.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0209631000
_diffrn_orient_matrix_UB_12      -0.0069488000
_diffrn_orient_matrix_UB_13      0.0709424000
_diffrn_orient_matrix_UB_21      -0.1004813000
_diffrn_orient_matrix_UB_22      -0.0932519000
_diffrn_orient_matrix_UB_23      0.0112078000
_diffrn_orient_matrix_UB_31      0.0228860000
_diffrn_orient_matrix_UB_32      -0.4013354000
_diffrn_orient_matrix_UB_33      -0.0038107000
_diffrn_oxdiff_digest_frames     
;
0192b2f16a1c2bfa58a409947da5d5895e0004297fc
;
_diffrn_oxdiff_digest_hkl        
;
0188cb8b99caa381a41092ef8d1d63d5d3a6ed
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2235
_reflns_number_total             2454
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2454
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.088
_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)+(0.0851P)²+0.5325P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1364
_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:
 C2(H2), C14(H14), C7(H7), C10(H10), C4(H4), C5(H5), C12(H12), C11(H11)
;
_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
Cl15 Cl 0.52667(3) 0.35804(14) 0.07092(2) 0.03479(19) Uani 1 1 d . . . . .
O19 O 0.24259(9) 0.2750(4) 0.32026(6) 0.0317(3) Uani 1 1 d . . . . .
O18 O 0.41507(9) 0.9665(5) 0.56189(6) 0.0371(4) Uani 1 1 d . . . . .
O17 O 0.27572(10) 0.9068(5) 0.58945(7) 0.0425(4) Uani 1 1 d . . . . .
N8 N 0.41330(10) 0.3189(4) 0.29314(7) 0.0245(3) Uani 1 1 d . . . . .
N16 N 0.33575(11) 0.8694(4) 0.55148(7) 0.0272(4) Uani 1 1 d . . . . .
C2 C 0.38035(12) 0.6567(5) 0.44933(8) 0.0238(4) Uani 1 1 d . . . . .
H2 H 0.441498 0.723158 0.460048 0.029 Uiso 1 1 calc R . . . .
C14 C 0.47152(12) 0.3211(5) 0.18957(8) 0.0247(4) Uani 1 1 d . . . . .
H14 H 0.414443 0.410031 0.173901 0.030 Uiso 1 1 calc R . . . .
C1 C 0.35874(12) 0.5101(5) 0.39119(8) 0.0236(4) Uani 1 1 d . . . . .
C3 C 0.31228(12) 0.7055(5) 0.49167(8) 0.0240(4) Uani 1 1 d . . . . .
C7 C 0.43060(12) 0.4517(5) 0.34729(8) 0.0247(4) Uani 1 1 d . . . . .
H7 H 0.491704 0.513465 0.359083 0.030 Uiso 1 1 calc R . . . .
C9 C 0.48638(12) 0.2514(5) 0.25305(8) 0.0236(4) Uani 1 1 d . . . . .
C6 C 0.26655(12) 0.4144(5) 0.37607(8) 0.0248(4) Uani 1 1 d . . . . .
C10 C 0.56926(12) 0.1099(5) 0.27549(8) 0.0257(4) Uani 1 1 d . . . . .
H10 H 0.578807 0.061175 0.318722 0.031 Uiso 1 1 calc R . . . .
C4 C 0.22157(12) 0.6105(5) 0.47756(9) 0.0266(4) Uani 1 1 d . . . . .
H4 H 0.175800 0.646262 0.507171 0.032 Uiso 1 1 calc R . . . .
C5 C 0.19976(12) 0.4642(5) 0.42003(9) 0.0279(4) Uani 1 1 d . . . . .
H5 H 0.138477 0.396220 0.410101 0.034 Uiso 1 1 calc R . . . .
C13 C 0.54246(12) 0.2568(5) 0.14995(8) 0.0259(4) Uani 1 1 d . . . . .
C12 C 0.62535(13) 0.1145(5) 0.17103(9) 0.0286(4) Uani 1 1 d . . . . .
H12 H 0.672546 0.068802 0.142886 0.034 Uiso 1 1 calc R . . . .
C11 C 0.63775(12) 0.0407(5) 0.23403(9) 0.0281(4) Uani 1 1 d . . . . .
H11 H 0.693957 -0.058730 0.249161 0.034 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
Cl15 C13 1.7435(18) . ?
O19 C6 1.340(2) . ?
O18 N16 1.231(2) . ?
O17 N16 1.229(2) . ?
N8 C7 1.280(2) . ?
N8 C9 1.420(2) . ?
N16 C3 1.451(2) . ?
C2 C1 1.388(2) . ?
C2 C3 1.385(2) . ?
C14 C9 1.395(2) . ?
C14 C13 1.388(2) . ?
C1 C7 1.455(2) . ?
C1 C6 1.424(2) . ?
C3 C4 1.398(3) . ?
C9 C10 1.394(2) . ?
C6 C5 1.396(3) . ?
C10 C11 1.389(3) . ?
C4 C5 1.376(3) . ?
C13 C12 1.387(3) . ?
C12 C11 1.384(3) . ?

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 N8 C9 119.30(15) . . ?
O18 N16 C3 118.46(15) . . ?
O17 N16 O18 122.75(16) . . ?
O17 N16 C3 118.79(15) . . ?
C3 C2 C1 119.65(16) . . ?
C13 C14 C9 118.13(16) . . ?
C2 C1 C7 119.59(15) . . ?
C2 C1 C6 119.15(16) . . ?
C6 C1 C7 121.25(16) . . ?
C2 C3 N16 118.80(15) . . ?
C2 C3 C4 121.77(16) . . ?
C4 C3 N16 119.41(16) . . ?
N8 C7 C1 121.43(16) . . ?
C14 C9 N8 117.59(15) . . ?
C10 C9 N8 121.69(15) . . ?
C10 C9 C14 120.69(16) . . ?
O19 C6 C1 121.09(16) . . ?
O19 C6 C5 119.18(16) . . ?
C5 C6 C1 119.73(16) . . ?
C11 C10 C9 119.37(16) . . ?
C5 C4 C3 118.85(17) . . ?
C4 C5 C6 120.84(17) . . ?
C14 C13 Cl15 118.80(14) . . ?
C12 C13 Cl15 118.91(14) . . ?
C12 C13 C14 122.29(16) . . ?
C11 C12 C13 118.45(17) . . ?
C12 C11 C10 121.03(17) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.669
_oxdiff_exptl_absorpt_empirical_full_min 0.533
####################################################################### 
# 
# 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_sh37_210_auto
_database_code_depnum_ccdc_archive 'CCDC 2156464'
loop_
_audit_author_name
_audit_author_address
'Frederick P. Malan'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2022-03-04 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2022-02-25
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 Cl N2 O3'
_chemical_formula_sum            'C13 H8 Cl N2 O3'
_chemical_formula_weight         275.66
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N4 O4 Cl'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.6907(2)
_cell_length_b                   3.75723(5)
_cell_length_c                   21.4853(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.9844(13)
_cell_angle_gamma                90
_cell_volume                     1185.20(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8767
_cell_measurement_temperature    210.00(10)
_cell_measurement_theta_max      78.7510
_cell_measurement_theta_min      3.5640
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.927
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             564
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12380
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.097
_diffrn_reflns_theta_min         3.588
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      210.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00 119.00   0.50    0.05    --   46.83  77.00  30.00  190
  2  ω     24.00 119.00   0.50    0.05    --   46.83  77.00 -60.00  190
  3  ω     24.00  53.00   0.50    0.05    --   46.83  77.00-150.00   58
  4  ω     34.00 121.00   0.50    0.05    --   46.83  18.00 -12.00  174
  5  ω    -26.00  41.00   0.50    0.05    --   46.83 -37.00  60.00  134
  6  ω    -26.00  41.00   0.50    0.05    --   46.83 -37.00  30.00  134
  7  ω     18.00  95.00   0.50    0.05    --   46.83-125.00 -90.00  154
  8  ω     38.00 111.00   0.50    0.25    --  110.25-125.00 -30.00  146
  9  ω     38.00 106.00   0.50    0.25    --  110.25 -94.00   0.00  136
 10  ω     38.00 106.00   0.50    0.25    --  110.25 -94.00  60.00  136
 11  ω     38.00 106.00   0.50    0.25    --  110.25 -94.00  90.00  136
 12  ω    -27.00  11.00   0.50    0.05    --   46.83 -18.00 179.00   76
 13  ω     38.00 106.00   0.50    0.25    --  110.25 -94.00 -90.00  136
 14  ω     38.00  80.00   0.50    0.25    --  110.25 -61.00 -30.00   84
 15  ω     38.00  80.00   0.50    0.25    --  110.25 -61.00  90.00   84
 16  ω     38.00  80.00   0.50    0.25    --  110.25 -61.00   0.00   84
 17  ω     38.00  80.00   0.50    0.25    --  110.25 -61.00 120.00   84
 18  ω     38.00  80.00   0.50    0.25    --  110.25 -61.00 -60.00   84
 19  ω     38.00  80.00   0.50    0.25    --  110.25 -61.00 -90.00   84
 20  ω     38.00  80.00   0.50    0.25    --  110.25 -61.00-180.00   84
 21  ω     97.00 175.00   0.50    0.25    --  110.25  15.00 -90.00  156
 22  ω     97.00 178.00   0.50    0.25    --  110.25  18.00 -12.00  162
 23  ω     98.00 178.00   0.50    0.25    --  110.25  30.00  90.00  160
 24  ω     -3.00  29.00   0.50    0.05    --  -46.83  18.00 -12.00   64
 25  ω     -5.00  29.00   0.50    0.05    --  -46.83  19.00 120.00   68
 26  ω   -112.00 -29.00   0.50    0.25    -- -102.00 125.00   0.00  166
 27  ω   -171.00 -89.00   0.50    0.25    -- -102.00 -18.00 179.00  164
 28  ω   -121.00 -34.00   0.50    0.05    --  -46.83 -18.00 179.00  174
 29  ω   -121.00 -34.00   0.50    0.05    --  -46.83 -19.00  90.00  174
 30  ω   -175.00 -89.00   0.50    0.25    -- -102.00 -30.00 -90.00  172
 31  ω   -175.00 -74.00   0.50    0.25    -- -102.00-125.00 -60.00  202
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0147568000
_diffrn_orient_matrix_UB_12      -0.0110088000
_diffrn_orient_matrix_UB_13      0.0713083000
_diffrn_orient_matrix_UB_21      -0.1009687000
_diffrn_orient_matrix_UB_22      -0.0979024000
_diffrn_orient_matrix_UB_23      0.0069782000
_diffrn_orient_matrix_UB_31      0.0244259000
_diffrn_orient_matrix_UB_32      -0.3980425000
_diffrn_orient_matrix_UB_33      -0.0036901000
_diffrn_oxdiff_digest_frames     
;
01d5e901f5f1388bc200506fc09ffc49aa00040e70b
;
_diffrn_oxdiff_digest_hkl        
;
010cfd2948325d8c173c634589f5e5b0b29d62
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2244
_reflns_number_total             2484
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.044
_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     173
_refine_ls_number_reflns         2484
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.074
_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)+(0.0412P)²+0.6192P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0956
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C14(H14), C7(H7), C10(H10), C4(H4), C5(H5), C12(H12), C11(H11)
2.b Idealised tetrahedral OH refined as rotating group:
 O19(H19)
;
_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
Cl15 Cl 0.52643(3) 0.63873(13) 0.07122(2) 0.04527(15) Uani 1 1 d . . . . .
O19 O 0.24280(8) 0.7205(4) 0.32057(5) 0.0400(3) Uani 1 1 d . . . . .
H19 H 0.288230 0.735959 0.298819 0.060 Uiso 1 1 calc GR . . . .
O18 O 0.41512(8) 0.0377(4) 0.56160(6) 0.0474(3) Uani 1 1 d . . . . .
N8 N 0.41345(9) 0.6772(4) 0.29296(6) 0.0301(3) Uani 1 1 d . . . . .
O17 O 0.27646(9) 0.0984(5) 0.58917(6) 0.0555(4) Uani 1 1 d . . . . .
N16 N 0.33596(9) 0.1345(4) 0.55122(6) 0.0342(3) Uani 1 1 d . . . . .
C1 C 0.35879(10) 0.4890(4) 0.39092(7) 0.0274(3) Uani 1 1 d . . . . .
C2 C 0.38029(10) 0.3429(4) 0.44905(7) 0.0286(3) Uani 1 1 d . . . . .
H2 H 0.440617 0.277067 0.459533 0.034 Uiso 1 1 calc R . . . .
C9 C 0.48657(10) 0.7446(4) 0.25296(7) 0.0284(3) Uani 1 1 d . . . . .
C14 C 0.47187(10) 0.6758(4) 0.18975(7) 0.0298(3) Uani 1 1 d . . . . .
H14 H 0.415470 0.588735 0.174381 0.036 Uiso 1 1 calc R . . . .
C7 C 0.43074(10) 0.5448(4) 0.34709(7) 0.0293(3) Uani 1 1 d . . . . .
H7 H 0.490954 0.482716 0.358663 0.035 Uiso 1 1 calc R . . . .
C3 C 0.31268(10) 0.2950(4) 0.49133(7) 0.0291(3) Uani 1 1 d . . . . .
C10 C 0.56931(11) 0.8837(4) 0.27506(7) 0.0318(3) Uani 1 1 d . . . . .
H10 H 0.578864 0.931507 0.317727 0.038 Uiso 1 1 calc R . . . .
C6 C 0.26714(10) 0.5829(4) 0.37594(7) 0.0305(3) Uani 1 1 d . . . . .
C4 C 0.22243(10) 0.3904(4) 0.47735(8) 0.0326(3) Uani 1 1 d . . . . .
H4 H 0.177338 0.356967 0.506784 0.039 Uiso 1 1 calc R . . . .
C13 C 0.54233(11) 0.7386(4) 0.15012(7) 0.0315(3) Uani 1 1 d . . . . .
C5 C 0.20048(10) 0.5338(5) 0.42000(8) 0.0342(4) Uani 1 1 d . . . . .
H5 H 0.139927 0.599669 0.410259 0.041 Uiso 1 1 calc R . . . .
C12 C 0.62515(11) 0.8784(4) 0.17085(8) 0.0348(4) Uani 1 1 d . . . . .
H12 H 0.671739 0.922649 0.142957 0.042 Uiso 1 1 calc R . . . .
C11 C 0.63753(10) 0.9512(4) 0.23368(8) 0.0348(4) Uani 1 1 d . . . . .
H11 H 0.693122 1.048013 0.248563 0.042 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
Cl15 C13 1.7440(16) . ?
O19 C6 1.3344(19) . ?
O18 N16 1.2314(18) . ?
N8 C9 1.4213(19) . ?
N8 C7 1.282(2) . ?
O17 N16 1.2234(18) . ?
N16 C3 1.451(2) . ?
C1 C2 1.391(2) . ?
C1 C7 1.455(2) . ?
C1 C6 1.418(2) . ?
C2 C3 1.381(2) . ?
C9 C14 1.392(2) . ?
C9 C10 1.391(2) . ?
C14 C13 1.383(2) . ?
C3 C4 1.396(2) . ?
C10 C11 1.386(2) . ?
C6 C5 1.398(2) . ?
C4 C5 1.373(2) . ?
C13 C12 1.385(2) . ?
C12 C11 1.383(2) . ?

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 N8 C9 119.17(13) . . ?
O18 N16 C3 118.39(13) . . ?
O17 N16 O18 122.60(14) . . ?
O17 N16 C3 119.01(14) . . ?
C2 C1 C7 119.39(13) . . ?
C2 C1 C6 119.10(13) . . ?
C6 C1 C7 121.51(14) . . ?
C3 C2 C1 119.74(13) . . ?
C14 C9 N8 117.51(13) . . ?
C10 C9 N8 122.02(14) . . ?
C10 C9 C14 120.45(14) . . ?
C13 C14 C9 118.35(14) . . ?
N8 C7 C1 121.16(14) . . ?
C2 C3 N16 118.99(13) . . ?
C2 C3 C4 121.63(14) . . ?
C4 C3 N16 119.37(14) . . ?
C11 C10 C9 119.51(15) . . ?
O19 C6 C1 121.44(14) . . ?
O19 C6 C5 118.86(14) . . ?
C5 C6 C1 119.70(14) . . ?
C5 C4 C3 119.05(14) . . ?
C14 C13 Cl15 118.93(12) . . ?
C14 C13 C12 122.32(15) . . ?
C12 C13 Cl15 118.75(12) . . ?
C4 C5 C6 120.76(14) . . ?
C11 C12 C13 118.25(15) . . ?
C12 C11 C10 121.09(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.449
_oxdiff_exptl_absorpt_empirical_full_min 0.569
####################################################################### 
# 
# 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_sh37_270b_auto
_database_code_depnum_ccdc_archive 'CCDC 2156466'
loop_
_audit_author_name
_audit_author_address
'Frederick P. Malan'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2022-03-04 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2022-02-25
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 Cl N2 O3'
_chemical_formula_sum            'C13 H8 Cl N2 O3'
_chemical_formula_weight         275.66
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N3 O4 Cl'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.7251(3)
_cell_length_b                   3.77870(10)
_cell_length_c                   21.5304(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.869(2)
_cell_angle_gamma                90
_cell_volume                     1197.35(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8288
_cell_measurement_temperature    269.99(10)
_cell_measurement_theta_max      78.4520
_cell_measurement_theta_min      2.9980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.897
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             564
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12528
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.528
_diffrn_reflns_theta_min         3.583
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      269.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     97.00 178.00   0.50    0.31    --  110.25  18.00 -14.00  162
  2  ω     97.00 175.00   0.50    0.31    --  110.25  15.00 -90.00  156
  3  ω     34.00 121.00   0.50    0.07    --   46.83  18.00 -14.00  174
  4  ω     35.00 120.00   0.50    0.07    --   46.83  37.00  30.00  170
  5  ω     24.00  78.00   0.50    0.07    --   46.83  77.00  60.00  108
  6  ω     -3.00  29.00   0.50    0.07    --  -46.83  18.00 -14.00   64
  7  ω     -5.00  29.00   0.50    0.07    --  -46.83  19.00 120.00   68
  8  ω   -125.00 -29.00   0.50    0.31    -- -102.00  77.00 120.00  192
  9  ω    -72.00 -29.00   0.50    0.31    -- -102.00  61.00 -90.00   86
 10  ω     38.00  80.00   0.50    0.31    --  110.25 -61.00-120.00   84
 11  ω     38.00  80.00   0.50    0.31    --  110.25 -61.00-180.00   84
 12  ω     38.00  80.00   0.50    0.31    --  110.25 -61.00 -30.00   84
 13  ω     38.00  80.00   0.50    0.31    --  110.25 -61.00   0.00   84
 14  ω     38.00  80.00   0.50    0.31    --  110.25 -61.00  30.00   84
 15  ω     38.00  80.00   0.50    0.31    --  110.25 -61.00  90.00   84
 16  ω     38.00  80.00   0.50    0.31    --  110.25 -61.00 120.00   84
 17  ω     38.00 106.00   0.50    0.31    --  110.25 -94.00  90.00  136
 18  ω     38.00 111.00   0.50    0.31    --  110.25-125.00  60.00  146
 19  ω     18.00  95.00   0.50    0.07    --   46.83-125.00 -60.00  154
 20  ω     38.00 106.00   0.50    0.31    --  110.25 -94.00 -30.00  136
 21  ω     38.00 106.00   0.50    0.31    --  110.25 -94.00  30.00  136
 22  ω    -27.00  11.00   0.50    0.07    --   46.83 -18.00 177.00   76
 23  ω     79.00 178.00   0.50    0.31    --  110.25 125.00-120.00  198
 24  ω    -26.00  41.00   0.50    0.07    --   46.83 -37.00  60.00  134
 25  ω    -26.00  41.00   0.50    0.07    --   46.83 -37.00  30.00  134
 26  ω   -118.00 -24.00   0.50    0.07    --  -46.83 -77.00 120.00  188
 27  ω   -175.00 -85.00   0.50    0.31    -- -102.00 -61.00  90.00  180
 28  ω   -121.00 -34.00   0.50    0.07    --  -46.83 -18.00 177.00  174
 29  ω   -171.00 -89.00   0.50    0.31    -- -102.00 -18.00 177.00  164
 30  ω   -175.00 -89.00   0.50    0.31    -- -102.00 -30.00  90.00  172
 31  ω   -118.00 -24.00   0.50    0.07    --  -46.83 -77.00-150.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0062565000
_diffrn_orient_matrix_UB_12      -0.0149776000
_diffrn_orient_matrix_UB_13      0.0715162000
_diffrn_orient_matrix_UB_21      -0.1015518000
_diffrn_orient_matrix_UB_22      -0.0966537000
_diffrn_orient_matrix_UB_23      0.0012795000
_diffrn_orient_matrix_UB_31      0.0245582000
_diffrn_orient_matrix_UB_32      -0.3958293000
_diffrn_orient_matrix_UB_33      -0.0030331000
_diffrn_oxdiff_digest_frames     
;
012c292d7ef24a1e739153f60b81a1ca6500040ab03
;
_diffrn_oxdiff_digest_hkl        
;
01efc7a4bc0a1c2191f6d66115c9e545bce121
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2176
_reflns_number_total             2503
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.047
_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         2503
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0407
_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)+(0.0691P)²+0.4293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1263
_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:
 C2(H2), C14(H14), C7(H7), C10(H10), C4(H4), C11(H11), C5(H5), C12(H12)
;
_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
Cl15 Cl 0.52613(4) 0.63544(17) 0.07152(2) 0.0604(2) Uani 1 1 d . . . . .
O19 O 0.24392(9) 0.7159(4) 0.32023(6) 0.0531(4) Uani 1 1 d . . . . .
N8 N 0.41374(10) 0.6726(4) 0.29285(7) 0.0388(3) Uani 1 1 d . . . . .
O18 O 0.41493(10) 0.0431(5) 0.56138(6) 0.0623(4) Uani 1 1 d . . . . .
N16 N 0.33652(11) 0.1389(4) 0.55091(7) 0.0452(4) Uani 1 1 d . . . . .
O17 O 0.27714(11) 0.1047(6) 0.58894(7) 0.0737(5) Uani 1 1 d . . . . .
C2 C 0.38058(11) 0.3434(4) 0.44869(8) 0.0375(4) Uani 1 1 d . . . . .
H2 H 0.440180 0.279780 0.459027 0.045 Uiso 1 1 calc R . . . .
C9 C 0.48686(11) 0.7388(5) 0.25288(8) 0.0374(4) Uani 1 1 d . . . . .
C3 C 0.31306(12) 0.2960(5) 0.49106(8) 0.0380(4) Uani 1 1 d . . . . .
C14 C 0.47202(12) 0.6710(5) 0.18989(8) 0.0393(4) Uani 1 1 d . . . . .
H14 H 0.416335 0.585323 0.174821 0.047 Uiso 1 1 calc R . . . .
C1 C 0.35906(11) 0.4864(5) 0.39068(8) 0.0364(4) Uani 1 1 d . . . . .
C7 C 0.43069(11) 0.5419(5) 0.34683(8) 0.0383(4) Uani 1 1 d . . . . .
H7 H 0.490120 0.481176 0.358250 0.046 Uiso 1 1 calc R . . . .
C10 C 0.56929(12) 0.8767(5) 0.27475(8) 0.0413(4) Uani 1 1 d . . . . .
H10 H 0.578741 0.923681 0.316869 0.050 Uiso 1 1 calc R . . . .
C6 C 0.26775(12) 0.5799(5) 0.37578(8) 0.0396(4) Uani 1 1 d . . . . .
C13 C 0.54235(13) 0.7344(5) 0.15015(8) 0.0414(4) Uani 1 1 d . . . . .
C4 C 0.22329(12) 0.3908(5) 0.47700(9) 0.0432(4) Uani 1 1 d . . . . .
H4 H 0.178751 0.358586 0.506126 0.052 Uiso 1 1 calc R . . . .
C11 C 0.63728(12) 0.9436(5) 0.23341(9) 0.0462(4) Uani 1 1 d . . . . .
H11 H 0.692192 1.038580 0.248018 0.055 Uiso 1 1 calc R . . . .
C5 C 0.20124(12) 0.5321(5) 0.41984(9) 0.0455(4) Uani 1 1 d . . . . .
H5 H 0.141464 0.596694 0.410300 0.055 Uiso 1 1 calc R . . . .
C12 C 0.62481(13) 0.8716(5) 0.17074(9) 0.0463(4) Uani 1 1 d . . . . .
H12 H 0.670852 0.914446 0.143160 0.056 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
Cl15 C13 1.7425(18) . ?
O19 C6 1.338(2) . ?
N8 C9 1.422(2) . ?
N8 C7 1.280(2) . ?
O18 N16 1.224(2) . ?
N16 O17 1.224(2) . ?
N16 C3 1.450(2) . ?
C2 C3 1.383(2) . ?
C2 C1 1.388(2) . ?
C9 C14 1.391(2) . ?
C9 C10 1.389(2) . ?
C3 C4 1.393(3) . ?
C14 C13 1.386(2) . ?
C1 C7 1.454(2) . ?
C1 C6 1.417(2) . ?
C10 C11 1.384(3) . ?
C6 C5 1.397(2) . ?
C13 C12 1.380(3) . ?
C4 C5 1.371(3) . ?
C11 C12 1.383(3) . ?

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 N8 C9 119.22(15) . . ?
O18 N16 O17 122.40(16) . . ?
O18 N16 C3 118.73(15) . . ?
O17 N16 C3 118.87(16) . . ?
C3 C2 C1 119.74(15) . . ?
C14 C9 N8 117.37(15) . . ?
C10 C9 N8 122.09(15) . . ?
C10 C9 C14 120.51(16) . . ?
C2 C3 N16 118.92(15) . . ?
C2 C3 C4 121.39(16) . . ?
C4 C3 N16 119.68(15) . . ?
C13 C14 C9 118.26(16) . . ?
C2 C1 C7 119.43(15) . . ?
C2 C1 C6 119.20(15) . . ?
C6 C1 C7 121.36(15) . . ?
N8 C7 C1 121.42(15) . . ?
C11 C10 C9 119.53(17) . . ?
O19 C6 C1 121.16(16) . . ?
O19 C6 C5 119.16(16) . . ?
C5 C6 C1 119.67(16) . . ?
C14 C13 Cl15 118.76(14) . . ?
C12 C13 Cl15 118.95(14) . . ?
C12 C13 C14 122.28(17) . . ?
C5 C4 C3 119.37(16) . . ?
C12 C11 C10 121.03(17) . . ?
C4 C5 C6 120.61(16) . . ?
C13 C12 C11 118.35(17) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.403
_oxdiff_exptl_absorpt_empirical_full_min 0.547
####################################################################### 
# 
# 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_SH01_133_auto
_database_code_depnum_ccdc_archive 'CCDC 2191107'
loop_
_audit_author_name
_audit_author_address
'Siya T. Hulushe'
;Rhodes University
South Africa
;
_audit_update_record             
;
2022-07-18 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H4 F1.50 N O1.50'
_chemical_formula_weight         154.61

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'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   14.3244(3)
_cell_length_b                   6.58850(10)
_cell_length_c                   14.1537(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.249(2)
_cell_angle_gamma                90
_cell_volume                     1275.70(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    141(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_F_000             628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.259
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      141(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6765
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.270
_diffrn_reflns_theta_max         78.918
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1456
_reflns_number_gt                1288
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0528P)²+1.3485P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1456
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1173
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
F6 F 0.96283(7) 0.66176(17) 0.11002(8) 0.0437(3) Uani 1 1 d . . . . .
F20 F 0.87995(11) 0.500000 -0.01923(10) 0.0487(4) Uani 1 2 d S T P . .
O16 O 0.91302(11) 0.500000 0.53855(12) 0.0397(5) Uani 1 2 d S T P . .
O5 O 0.63008(13) 0.500000 0.79801(11) 0.0393(4) Uani 1 2 d S T P . .
N11 N 0.78166(13) 0.500000 0.36460(12) 0.0253(4) Uani 1 2 d S T P . .
N4 N 0.60956(14) 0.500000 0.70782(13) 0.0317(4) Uani 1 2 d S T P . .
O21 O 0.52546(13) 0.500000 0.65424(14) 0.0694(8) Uani 1 2 d S T P . .
C10 C 0.75717(15) 0.500000 0.25968(14) 0.0242(4) Uani 1 2 d S T P . .
C2 C 0.66521(16) 0.500000 0.56023(15) 0.0263(5) Uani 1 2 d S T P . .
H2 H 0.598809 0.500000 0.520659 0.032 Uiso 1 2 calc R U P . .
C8 C 0.81886(16) 0.500000 0.11859(15) 0.0265(5) Uani 1 2 d S T P . .
C3 C 0.68810(16) 0.500000 0.66218(15) 0.0261(5) Uani 1 2 d S T P . .
C12 C 0.71490(15) 0.500000 0.40834(15) 0.0254(4) Uani 1 2 d S T P . .
H12 H 0.648111 0.500000 0.369933 0.030 Uiso 1 2 calc R U P . .
C1 C 0.73985(15) 0.500000 0.51565(14) 0.0245(4) Uani 1 2 d S T P . .
H1 H 0.885(3) 0.500000 0.474(3) 0.070(11) Uiso 1 2 d S . P . .
C15 C 0.83826(16) 0.500000 0.57671(16) 0.0293(5) Uani 1 2 d S T P . .
C9 C 0.83527(15) 0.500000 0.22066(15) 0.0253(4) Uani 1 2 d S T P . .
H9 H 0.900286 0.500000 0.263749 0.030 Uiso 1 2 calc R U P . .
C14 C 0.85853(17) 0.500000 0.67943(16) 0.0347(5) Uani 1 2 d S T P . .
H14 H 0.924539 0.500000 0.720076 0.042 Uiso 1 2 calc R U P . .
C7 C 0.90517(16) 0.500000 0.07926(15) 0.0299(5) Uani 1 2 d S T P . .
C13 C 0.78420(17) 0.500000 0.72266(15) 0.0300(5) Uani 1 2 d S T P . .
H13 H 0.798380 0.500000 0.792617 0.036 Uiso 1 2 calc R U P . .
C18 C 0.64663(17) 0.500000 0.09420(16) 0.0354(5) Uani 1 2 d S T P . .
H18 H 0.581703 0.500000 0.050914 0.042 Uiso 1 2 calc R U P . .
C17 C 0.66156(16) 0.500000 0.19499(15) 0.0306(5) Uani 1 2 d S T P . .
H17 H 0.607301 0.500000 0.220602 0.037 Uiso 1 2 calc R U P . .
C19 C 0.72446(17) 0.500000 0.05458(15) 0.0312(5) Uani 1 2 d S T P . .
H19 H 0.713252 0.500000 -0.015022 0.037 Uiso 1 2 calc R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F6 C7 1.3395(17) . ?
F20 C7 1.332(2) . ?
O16 C15 1.335(3) . ?
O5 N4 1.222(2) . ?
N11 C12 1.284(3) . ?
N11 C10 1.421(3) . ?
N4 O21 1.218(3) . ?
N4 C3 1.454(3) . ?
C10 C9 1.387(3) . ?
C10 C17 1.404(3) . ?
C2 C3 1.382(3) . ?
C2 C1 1.393(3) . ?
C8 C19 1.387(3) . ?
C8 C9 1.393(3) . ?
C8 C7 1.499(3) . ?
C3 C13 1.389(3) . ?
C12 C1 1.453(3) . ?
C1 C15 1.418(3) . ?
C15 C14 1.396(3) . ?
C14 C13 1.376(3) . ?
C18 C17 1.378(3) . ?
C18 C19 1.389(3) . ?

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 N11 C10 121.03(18) . . ?
O21 N4 O5 122.5(2) . . ?
O21 N4 C3 118.42(18) . . ?
O5 N4 C3 119.08(19) . . ?
C9 C10 C17 119.12(18) . . ?
C9 C10 N11 115.97(18) . . ?
C17 C10 N11 124.92(19) . . ?
C3 C2 C1 119.78(19) . . ?
C19 C8 C9 120.63(19) . . ?
C19 C8 C7 120.62(18) . . ?
C9 C8 C7 118.75(18) . . ?
C2 C3 C13 121.9(2) . . ?
C2 C3 N4 119.26(19) . . ?
C13 C3 N4 118.83(18) . . ?
N11 C12 C1 121.09(19) . . ?
C2 C1 C15 118.78(18) . . ?
C2 C1 C12 119.30(19) . . ?
C15 C1 C12 121.92(19) . . ?
O16 C15 C14 118.53(19) . . ?
O16 C15 C1 121.68(19) . . ?
C14 C15 C1 119.8(2) . . ?
C10 C9 C8 120.33(19) . . ?
C13 C14 C15 120.9(2) . . ?
F20 C7 F6 106.85(12) . . ?
F20 C7 F6 106.85(12) . 6_565 ?
F6 C7 F6 105.44(18) . 6_565 ?
F20 C7 C8 113.01(18) . . ?
F6 C7 C8 112.10(12) . . ?
F6 C7 C8 112.10(12) 6_565 . ?
C14 C13 C3 118.82(19) . . ?
C17 C18 C19 121.4(2) . . ?
C18 C17 C10 119.8(2) . . ?
C8 C19 C18 118.71(19) . . ?

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
C12 N11 C10 C9 180.000(0) . . . . ?
C12 N11 C10 C17 0.000(0) . . . . ?
C1 C2 C3 C13 0.000(1) . . . . ?
C1 C2 C3 N4 180.000(1) . . . . ?
O21 N4 C3 C2 0.000(1) . . . . ?
O5 N4 C3 C2 180.000(1) . . . . ?
O21 N4 C3 C13 180.000(1) . . . . ?
O5 N4 C3 C13 0.000(1) . . . . ?
C10 N11 C12 C1 180.000(0) . . . . ?
C3 C2 C1 C15 0.000(1) . . . . ?
C3 C2 C1 C12 180.000(1) . . . . ?
N11 C12 C1 C2 180.000(0) . . . . ?
N11 C12 C1 C15 0.000(1) . . . . ?
C2 C1 C15 O16 180.000(1) . . . . ?
C12 C1 C15 O16 0.000(1) . . . . ?
C2 C1 C15 C14 0.000(1) . . . . ?
C12 C1 C15 C14 180.000(1) . . . . ?
C17 C10 C9 C8 0.000(0) . . . . ?
N11 C10 C9 C8 180.000(0) . . . . ?
C19 C8 C9 C10 0.000(0) . . . . ?
C7 C8 C9 C10 180.000(0) . . . . ?
O16 C15 C14 C13 180.000(1) . . . . ?
C1 C15 C14 C13 0.000(1) . . . . ?
C19 C8 C7 F20 0.000(0) . . . . ?
C9 C8 C7 F20 180.000(0) . . . . ?
C19 C8 C7 F6 120.82(13) . . . . ?
C9 C8 C7 F6 -59.18(13) . . . . ?
C19 C8 C7 F6 -120.82(13) . . . 6_565 ?
C9 C8 C7 F6 59.18(13) . . . 6_565 ?
C15 C14 C13 C3 0.000(1) . . . . ?
C2 C3 C13 C14 0.000(1) . . . . ?
N4 C3 C13 C14 180.000(1) . . . . ?
C19 C18 C17 C10 0.000(0) . . . . ?
C9 C10 C17 C18 0.000(0) . . . . ?
N11 C10 C17 C18 180.000(0) . . . . ?
C9 C8 C19 C18 0.000(0) . . . . ?
C7 C8 C19 C18 180.0 . . . . ?
C17 C18 C19 C8 0.000(0) . . . . ?

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_sh37_240_auto
_database_code_depnum_ccdc_archive 'CCDC 2156465'
loop_
_audit_author_name
_audit_author_address
'Frederick P. Malan'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2022-03-04 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2022-02-25
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 Cl N2 O3'
_chemical_formula_sum            'C13 H8 Cl N2 O3'
_chemical_formula_weight         275.66
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N4 O4 Cl'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.7034(3)
_cell_length_b                   3.76610(10)
_cell_length_c                   21.5036(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.924(2)
_cell_angle_gamma                90
_cell_volume                     1190.08(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8278
_cell_measurement_temperature    240.00(10)
_cell_measurement_theta_max      78.7810
_cell_measurement_theta_min      3.6000
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.915
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             564
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12317
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.037
_diffrn_reflns_theta_min         3.586
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      240.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00  94.00   0.50    0.05    --   46.71  57.00  60.00  124
  2  ω     24.00 118.00   0.50    0.05    --   46.71  77.00  90.00  188
  3  ω     24.00 118.00   0.50    0.05    --   46.71  77.00   0.00  188
  4  ω     24.00 118.00   0.50    0.05    --   46.71  77.00 -90.00  188
  5  ω     24.00 118.00   0.50    0.05    --   46.71  77.00-180.00  188
  6  ω     34.00 121.00   0.50    0.05    --   46.71  18.00 -12.00  174
  7  ω    -26.00  41.00   0.50    0.05    --   46.71 -37.00  60.00  134
  8  ω    -28.00  13.00   0.50    0.05    --   46.71 -19.00  30.00   82
  9  ω    -28.00  11.00   0.50    0.05    --   46.71 -18.00 178.00   78
 10  ω     38.00  80.00   0.50    0.25    --  110.25 -61.00 120.00   84
 11  ω     38.00  80.00   0.50    0.25    --  110.25 -61.00  90.00   84
 12  ω     38.00 133.00   0.50    0.25    --  110.25 -77.00  30.00  190
 13  ω     38.00 133.00   0.50    0.25    --  110.25 -77.00-150.00  190
 14  ω     38.00  80.00   0.50    0.25    --  110.25 -61.00-120.00   84
 15  ω     38.00 106.00   0.50    0.25    --  110.25 -94.00 -30.00  136
 16  ω     38.00 106.00   0.50    0.25    --  110.25 -94.00  30.00  136
 17  ω     38.00 111.00   0.50    0.25    --  110.25-125.00  60.00  146
 18  ω     18.00  94.00   0.50    0.05    --   46.71-125.00 -90.00  152
 19  ω     97.00 178.00   0.50    0.25    --  110.25  18.00 -12.00  162
 20  ω     94.00 178.00   0.50    0.25    --  110.25  61.00  60.00  168
 21  ω     98.00 178.00   0.50    0.25    --  110.25  30.00  30.00  160
 22  ω     98.00 178.00   0.50    0.25    --  110.25  30.00 -90.00  160
 23  ω     -3.00  29.00   0.50    0.05    --  -46.71  18.00 -12.00   64
 24  ω   -121.00 -34.00   0.50    0.05    --  -46.71 -18.00 178.00  174
 25  ω   -171.00 -89.00   0.50    0.25    -- -102.00 -18.00 178.00  164
 26  ω    -32.00  27.00   0.50    0.05    --  -46.71  37.00 150.00  118
 27  ω   -112.00 -29.00   0.50    0.25    -- -102.00 125.00   0.00  166
 28  ω   -167.00 -88.00   0.50    0.25    -- -102.00 -15.00-120.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0118346000
_diffrn_orient_matrix_UB_12      -0.0120438000
_diffrn_orient_matrix_UB_13      0.0714284000
_diffrn_orient_matrix_UB_21      -0.1012675000
_diffrn_orient_matrix_UB_22      -0.0969680000
_diffrn_orient_matrix_UB_23      0.0050459000
_diffrn_orient_matrix_UB_31      0.0243791000
_diffrn_orient_matrix_UB_32      -0.3972096000
_diffrn_orient_matrix_UB_33      -0.0033972000
_diffrn_oxdiff_digest_frames     
;
01305d944fc6b44d0437f403e1b9700788000418120
;
_diffrn_oxdiff_digest_hkl        
;
01d439f83cebc172779849356ed43052230d03
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2193
_reflns_number_total             2507
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2507
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.080
_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)+(0.0482P)²+0.5093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1045
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C14(H14), C7(H7), C10(H10), C4(H4), C11(H11), C5(H5), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O19(H19)
;
_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
Cl15 Cl 0.52629(3) 0.63716(15) 0.07136(2) 0.05241(17) Uani 1 1 d . . . . .
O19 O 0.24310(8) 0.7182(4) 0.32063(6) 0.0461(3) Uani 1 1 d . . . . .
H19 H 0.288437 0.733421 0.298807 0.069 Uiso 1 1 calc GR . . . .
O18 O 0.41503(9) 0.0403(5) 0.56147(6) 0.0546(4) Uani 1 1 d . . . . .
N8 N 0.41369(9) 0.6750(4) 0.29297(6) 0.0341(3) Uani 1 1 d . . . . .
N16 N 0.33620(10) 0.1365(4) 0.55105(6) 0.0393(3) Uani 1 1 d . . . . .
O17 O 0.27682(10) 0.1013(5) 0.58906(6) 0.0640(4) Uani 1 1 d . . . . .
C2 C 0.38043(10) 0.3431(4) 0.44878(7) 0.0328(3) Uani 1 1 d . . . . .
H2 H 0.440731 0.277674 0.459200 0.039 Uiso 1 1 calc R . . . .
C9 C 0.48665(10) 0.7416(4) 0.25287(7) 0.0323(3) Uani 1 1 d . . . . .
C3 C 0.31290(11) 0.2955(4) 0.49121(7) 0.0332(3) Uani 1 1 d . . . . .
C14 C 0.47198(11) 0.6737(4) 0.18990(7) 0.0340(3) Uani 1 1 d . . . . .
H14 H 0.415570 0.587251 0.174624 0.041 Uiso 1 1 calc R . . . .
C1 C 0.35899(10) 0.4877(4) 0.39081(7) 0.0317(3) Uani 1 1 d . . . . .
C7 C 0.43078(10) 0.5434(4) 0.34691(7) 0.0333(3) Uani 1 1 d . . . . .
H7 H 0.490937 0.481293 0.358422 0.040 Uiso 1 1 calc R . . . .
C6 C 0.26746(11) 0.5818(4) 0.37580(7) 0.0346(3) Uani 1 1 d . . . . .
C10 C 0.56929(11) 0.8802(4) 0.27488(8) 0.0361(4) Uani 1 1 d . . . . .
H10 H 0.578828 0.927910 0.317508 0.043 Uiso 1 1 calc R . . . .
C4 C 0.22281(11) 0.3911(5) 0.47710(8) 0.0379(4) Uani 1 1 d . . . . .
H4 H 0.177687 0.358252 0.506508 0.046 Uiso 1 1 calc R . . . .
C13 C 0.54232(11) 0.7362(5) 0.15009(8) 0.0365(4) Uani 1 1 d . . . . .
C11 C 0.63739(11) 0.9475(5) 0.23356(9) 0.0400(4) Uani 1 1 d . . . . .
H11 H 0.692979 1.043760 0.248385 0.048 Uiso 1 1 calc R . . . .
C5 C 0.20095(11) 0.5331(5) 0.41997(8) 0.0392(4) Uani 1 1 d . . . . .
H5 H 0.140436 0.598775 0.410296 0.047 Uiso 1 1 calc R . . . .
C12 C 0.62490(11) 0.8752(5) 0.17082(8) 0.0406(4) Uani 1 1 d . . . . .
H12 H 0.671446 0.919595 0.142932 0.049 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
Cl15 C13 1.7419(17) . ?
O19 C6 1.331(2) . ?
O18 N16 1.2278(19) . ?
N8 C9 1.4210(19) . ?
N8 C7 1.279(2) . ?
N16 O17 1.2231(19) . ?
N16 C3 1.450(2) . ?
C2 C3 1.382(2) . ?
C2 C1 1.387(2) . ?
C9 C14 1.388(2) . ?
C9 C10 1.391(2) . ?
C3 C4 1.396(2) . ?
C14 C13 1.385(2) . ?
C1 C7 1.455(2) . ?
C1 C6 1.418(2) . ?
C6 C5 1.398(2) . ?
C10 C11 1.384(2) . ?
C4 C5 1.368(2) . ?
C13 C12 1.382(2) . ?
C11 C12 1.382(3) . ?

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 N8 C9 119.30(13) . . ?
O18 N16 C3 118.52(13) . . ?
O17 N16 O18 122.45(15) . . ?
O17 N16 C3 119.02(14) . . ?
C3 C2 C1 119.82(14) . . ?
C14 C9 N8 117.62(14) . . ?
C14 C9 C10 120.44(14) . . ?
C10 C9 N8 121.91(14) . . ?
C2 C3 N16 119.05(14) . . ?
C2 C3 C4 121.36(15) . . ?
C4 C3 N16 119.58(14) . . ?
C13 C14 C9 118.50(15) . . ?
C2 C1 C7 119.46(14) . . ?
C2 C1 C6 119.21(14) . . ?
C6 C1 C7 121.33(14) . . ?
N8 C7 C1 121.32(14) . . ?
O19 C6 C1 121.61(14) . . ?
O19 C6 C5 118.87(14) . . ?
C5 C6 C1 119.52(15) . . ?
C11 C10 C9 119.53(15) . . ?
C5 C4 C3 119.24(15) . . ?
C14 C13 Cl15 119.01(13) . . ?
C12 C13 Cl15 118.91(13) . . ?
C12 C13 C14 122.08(15) . . ?
C12 C11 C10 121.00(15) . . ?
C4 C5 C6 120.84(15) . . ?
C13 C12 C11 118.41(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.462
_oxdiff_exptl_absorpt_empirical_full_min 0.610
####################################################################### 
# 
# 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_SH01_150_auto
_database_code_depnum_ccdc_archive 'CCDC 2191108'
loop_
_audit_author_name
_audit_author_address
'Siya T. Hulushe'
;Rhodes University
South Africa
;
_audit_update_record             
;
2022-07-18 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 F1.50 N O1.50'
_chemical_formula_sum            'C7 H4 F1.50 N O1.50'
_chemical_formula_weight         154.61

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'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   14.3165(4)
_cell_length_b                   6.5939(2)
_cell_length_c                   14.1523(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.224(3)
_cell_angle_gamma                90
_cell_volume                     1276.09(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       platelets
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_F_000             628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.343
_exptl_crystal_size_mid          0.284
_exptl_crystal_size_min          0.212
_exptl_absorpt_coefficient_mu    1.259
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6528
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.269
_diffrn_reflns_theta_max         79.129
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1442
_reflns_number_gt                1311
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0416P)²+1.6317P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1442
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1205
_refine_ls_wR_factor_gt          0.1185
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_restrained_S_all      1.208
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
F6 F 0.96270(8) 0.66148(19) 0.10991(8) 0.0448(3) Uani 1 1 d . . . . .
F20 F 0.87981(12) 0.500000 -0.01915(11) 0.0502(5) Uani 1 2 d S T P . .
O16 O 0.91294(13) 0.500000 0.53844(13) 0.0404(5) Uani 1 2 d S T P . .
O5 O 0.63011(15) 0.500000 0.79793(13) 0.0401(5) Uani 1 2 d S T P . .
N11 N 0.78179(14) 0.500000 0.36473(14) 0.0251(4) Uani 1 2 d S T P . .
N4 N 0.60955(16) 0.500000 0.70797(15) 0.0322(5) Uani 1 2 d S T P . .
O21 O 0.52550(15) 0.500000 0.65428(15) 0.0703(9) Uani 1 2 d S T P . .
C1 C 0.73978(17) 0.500000 0.51572(16) 0.0253(5) Uani 1 2 d S T P . .
H1 H 0.887(3) 0.500000 0.474(3) 0.061(11) Uiso 1 2 d S . P . .
C10 C 0.75722(17) 0.500000 0.25975(16) 0.0245(5) Uani 1 2 d S T P . .
C8 C 0.81890(17) 0.500000 0.11869(16) 0.0265(5) Uani 1 2 d S T P . .
C12 C 0.71497(17) 0.500000 0.40843(16) 0.0258(5) Uani 1 2 d S T P . .
H12 H 0.648170 0.500000 0.369989 0.031 Uiso 1 2 calc R U P . .
C3 C 0.68815(18) 0.500000 0.66220(17) 0.0270(5) Uani 1 2 d S T P . .
C9 C 0.83521(17) 0.500000 0.22077(16) 0.0252(5) Uani 1 2 d S T P . .
H9 H 0.900242 0.500000 0.263861 0.030 Uiso 1 2 calc R U P . .
C13 C 0.78430(19) 0.500000 0.72251(17) 0.0306(5) Uani 1 2 d S T P . .
H13 H 0.798528 0.500000 0.792474 0.037 Uiso 1 2 calc R U P . .
C2 C 0.66537(17) 0.500000 0.56039(17) 0.0269(5) Uani 1 2 d S T P . .
H2 H 0.598934 0.500000 0.520862 0.032 Uiso 1 2 calc R U P . .
C14 C 0.85838(18) 0.500000 0.67939(18) 0.0358(6) Uani 1 2 d S T P . .
H14 H 0.924418 0.500000 0.720026 0.043 Uiso 1 2 calc R U P . .
C18 C 0.64664(19) 0.500000 0.09434(18) 0.0365(6) Uani 1 2 d S T P . .
H18 H 0.581701 0.500000 0.051036 0.044 Uiso 1 2 calc R U P . .
C15 C 0.83816(18) 0.500000 0.57662(18) 0.0302(5) Uani 1 2 d S T P . .
C7 C 0.90501(18) 0.500000 0.07936(17) 0.0306(5) Uani 1 2 d S T P . .
C17 C 0.66162(18) 0.500000 0.19539(17) 0.0314(6) Uani 1 2 d S T P . .
H17 H 0.607399 0.500000 0.221106 0.038 Uiso 1 2 calc R U P . .
C19 C 0.72435(19) 0.500000 0.05497(17) 0.0318(6) Uani 1 2 d S T P . .
H19 H 0.713091 0.500000 -0.014640 0.038 Uiso 1 2 calc R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F6 C7 1.3384(19) . ?
F20 C7 1.333(3) . ?
O16 C15 1.334(3) . ?
O5 N4 1.219(3) . ?
N11 C12 1.284(3) . ?
N11 C10 1.422(3) . ?
N4 O21 1.218(3) . ?
N4 C3 1.455(3) . ?
C1 C2 1.390(3) . ?
C1 C15 1.417(3) . ?
C1 C12 1.453(3) . ?
C10 C9 1.384(3) . ?
C10 C17 1.402(3) . ?
C8 C19 1.387(3) . ?
C8 C9 1.393(3) . ?
C8 C7 1.495(3) . ?
C3 C2 1.380(3) . ?
C3 C13 1.388(3) . ?
C13 C14 1.371(4) . ?
C14 C15 1.396(3) . ?
C18 C17 1.382(3) . ?
C18 C19 1.384(4) . ?

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 N11 C10 121.0(2) . . ?
O21 N4 O5 122.7(2) . . ?
O21 N4 C3 118.3(2) . . ?
O5 N4 C3 119.1(2) . . ?
C2 C1 C15 118.7(2) . . ?
C2 C1 C12 119.5(2) . . ?
C15 C1 C12 121.8(2) . . ?
C9 C10 C17 119.2(2) . . ?
C9 C10 N11 115.9(2) . . ?
C17 C10 N11 124.8(2) . . ?
C19 C8 C9 120.4(2) . . ?
C19 C8 C7 120.8(2) . . ?
C9 C8 C7 118.8(2) . . ?
N11 C12 C1 121.1(2) . . ?
C2 C3 C13 121.8(2) . . ?
C2 C3 N4 119.3(2) . . ?
C13 C3 N4 118.9(2) . . ?
C10 C9 C8 120.4(2) . . ?
C14 C13 C3 118.9(2) . . ?
C3 C2 C1 119.9(2) . . ?
C13 C14 C15 121.0(2) . . ?
C17 C18 C19 121.3(2) . . ?
O16 C15 C14 118.6(2) . . ?
O16 C15 C1 121.7(2) . . ?
C14 C15 C1 119.7(2) . . ?
F20 C7 F6 106.74(14) . 6_565 ?
F20 C7 F6 106.73(14) . . ?
F6 C7 F6 105.4(2) 6_565 . ?
F20 C7 C8 113.1(2) . . ?
F6 C7 C8 112.19(13) 6_565 . ?
F6 C7 C8 112.19(13) . . ?
C18 C17 C10 119.7(2) . . ?
C18 C19 C8 119.0(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N11 C10 C9 180.000(0) . . . . ?
C12 N11 C10 C17 0.000(0) . . . . ?
C10 N11 C12 C1 180.000(0) . . . . ?
C2 C1 C12 N11 180.000(1) . . . . ?
C15 C1 C12 N11 0.000(1) . . . . ?
O21 N4 C3 C2 0.000(1) . . . . ?
O5 N4 C3 C2 180.000(1) . . . . ?
O21 N4 C3 C13 180.000(1) . . . . ?
O5 N4 C3 C13 0.000(1) . . . . ?
C17 C10 C9 C8 0.000(0) . . . . ?
N11 C10 C9 C8 180.000(0) . . . . ?
C19 C8 C9 C10 0.000(0) . . . . ?
C7 C8 C9 C10 180.000(0) . . . . ?
C2 C3 C13 C14 0.000(1) . . . . ?
N4 C3 C13 C14 180.000(1) . . . . ?
C13 C3 C2 C1 0.000(1) . . . . ?
N4 C3 C2 C1 180.000(1) . . . . ?
C15 C1 C2 C3 0.000(1) . . . . ?
C12 C1 C2 C3 180.000(1) . . . . ?
C3 C13 C14 C15 0.000(1) . . . . ?
C13 C14 C15 O16 180.000(1) . . . . ?
C13 C14 C15 C1 0.000(1) . . . . ?
C2 C1 C15 O16 180.000(1) . . . . ?
C12 C1 C15 O16 0.000(1) . . . . ?
C2 C1 C15 C14 0.000(1) . . . . ?
C12 C1 C15 C14 180.000(1) . . . . ?
C19 C8 C7 F20 0.000(0) . . . . ?
C9 C8 C7 F20 180.000(0) . . . . ?
C19 C8 C7 F6 -120.78(14) . . . 6_565 ?
C9 C8 C7 F6 59.22(14) . . . 6_565 ?
C19 C8 C7 F6 120.78(14) . . . . ?
C9 C8 C7 F6 -59.22(14) . . . . ?
C19 C18 C17 C10 0.000(0) . . . . ?
C9 C10 C17 C18 0.000(0) . . . . ?
N11 C10 C17 C18 180.000(0) . . . . ?
C17 C18 C19 C8 0.000(0) . . . . ?
C9 C8 C19 C18 0.000(0) . . . . ?
C7 C8 C19 C18 180.0 . . . . ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_SH01_180_auto
_database_code_depnum_ccdc_archive 'CCDC 2191109'
loop_
_audit_author_name
_audit_author_address
'Siya T. Hulushe'
;Rhodes University
South Africa
;
_audit_update_record             
;
2022-07-18 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 F1.50 N O1.50'
_chemical_formula_sum            'C7 H4 F1.50 N O1.50'
_chemical_formula_weight         154.61

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'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   14.3145(4)
_cell_length_b                   6.6220(2)
_cell_length_c                   14.1681(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.166(3)
_cell_angle_gamma                90
_cell_volume                     1283.18(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       platelets
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_F_000             628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.343
_exptl_crystal_size_mid          0.284
_exptl_crystal_size_min          0.212
_exptl_absorpt_coefficient_mu    1.252
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6866
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.265
_diffrn_reflns_theta_max         79.250
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1447
_reflns_number_gt                1303
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0492P)²+1.2761P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1447
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1241
_refine_ls_wR_factor_gt          0.1224
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.162
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
F6 F 0.03797(8) 0.3397(2) 0.89031(8) 0.0551(4) Uani 1 1 d . . . . .
F20 F 0.12096(12) 0.500000 1.01876(10) 0.0610(5) Uani 1 2 d S T P . .
O16 O 0.08710(12) 0.500000 0.46160(13) 0.0491(5) Uani 1 2 d S T P . .
O5 O 0.36994(15) 0.500000 0.20228(12) 0.0487(5) Uani 1 2 d S T P . .
N11 N 0.21831(13) 0.500000 0.63499(13) 0.0308(4) Uani 1 2 d S T P . .
N4 N 0.39030(15) 0.500000 0.29199(14) 0.0390(5) Uani 1 2 d S T P . .
O21 O 0.47428(14) 0.500000 0.34536(15) 0.0834(10) Uani 1 2 d S T P . .
C1 C 0.26007(16) 0.500000 0.48407(15) 0.0302(5) Uani 1 2 d S T P . .
H1 H 0.113(3) 0.500000 0.523(3) 0.069(11) Uiso 1 2 d S . P . .
C3 C 0.31181(17) 0.500000 0.33775(16) 0.0321(5) Uani 1 2 d S T P . .
C8 C 0.18164(16) 0.500000 0.88107(15) 0.0317(5) Uani 1 2 d S T P . .
C9 C 0.16510(16) 0.500000 0.77914(15) 0.0303(5) Uani 1 2 d S T P . .
H9 H 0.100023 0.500000 0.736296 0.036 Uiso 1 2 calc R U P . .
C7 C 0.09562(18) 0.500000 0.92066(16) 0.0375(6) Uani 1 2 d S T P . .
C10 C 0.24307(16) 0.500000 0.73983(15) 0.0295(5) Uani 1 2 d S T P . .
C2 C 0.33463(16) 0.500000 0.43950(16) 0.0321(5) Uani 1 2 d S T P . .
H2 H 0.401041 0.500000 0.478943 0.039 Uiso 1 2 calc R U P . .
C14 C 0.14164(18) 0.500000 0.32075(17) 0.0429(6) Uani 1 2 d S T P . .
H14 H 0.075614 0.500000 0.280234 0.051 Uiso 1 2 calc R U P . .
C12 C 0.28504(16) 0.500000 0.59121(15) 0.0313(5) Uani 1 2 d S T P . .
H12 H 0.351855 0.500000 0.629471 0.038 Uiso 1 2 calc R U P . .
C15 C 0.16186(17) 0.500000 0.42341(17) 0.0356(5) Uani 1 2 d S T P . .
C17 C 0.33851(17) 0.500000 0.80396(17) 0.0377(6) Uani 1 2 d S T P . .
H17 H 0.392679 0.500000 0.778141 0.045 Uiso 1 2 calc R U P . .
C13 C 0.21574(18) 0.500000 0.27757(16) 0.0372(5) Uani 1 2 d S T P . .
H13 H 0.201538 0.500000 0.207702 0.045 Uiso 1 2 calc R U P . .
C18 C 0.35372(18) 0.500000 0.90473(17) 0.0436(6) Uani 1 2 d S T P . .
H18 H 0.418703 0.500000 0.947796 0.052 Uiso 1 2 calc R U P . .
C19 C 0.27592(18) 0.500000 0.94441(16) 0.0383(6) Uani 1 2 d S T P . .
H19 H 0.287251 0.500000 1.013943 0.046 Uiso 1 2 calc R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F6 C7 1.3355(19) . ?
F20 C7 1.329(3) . ?
O16 C15 1.334(3) . ?
O5 N4 1.217(3) . ?
N11 C12 1.283(3) . ?
N11 C10 1.422(3) . ?
N4 O21 1.217(3) . ?
N4 C3 1.454(3) . ?
C1 C2 1.391(3) . ?
C1 C15 1.415(3) . ?
C1 C12 1.453(3) . ?
C3 C2 1.381(3) . ?
C3 C13 1.388(3) . ?
C8 C19 1.383(3) . ?
C8 C9 1.393(3) . ?
C8 C7 1.496(3) . ?
C9 C10 1.387(3) . ?
C10 C17 1.400(3) . ?
C14 C13 1.372(3) . ?
C14 C15 1.397(3) . ?
C17 C18 1.379(3) . ?
C18 C19 1.388(3) . ?

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 N11 C10 120.89(19) . . ?
O21 N4 O5 122.5(2) . . ?
O21 N4 C3 118.35(19) . . ?
O5 N4 C3 119.2(2) . . ?
C2 C1 C15 118.82(19) . . ?
C2 C1 C12 119.3(2) . . ?
C15 C1 C12 121.9(2) . . ?
C2 C3 C13 121.8(2) . . ?
C2 C3 N4 119.3(2) . . ?
C13 C3 N4 118.8(2) . . ?
C19 C8 C9 120.5(2) . . ?
C19 C8 C7 120.69(19) . . ?
C9 C8 C7 118.81(19) . . ?
C10 C9 C8 120.4(2) . . ?
F20 C7 F6 106.78(13) . . ?
F20 C7 F6 106.78(13) . 6_565 ?
F6 C7 F6 105.3(2) . 6_565 ?
F20 C7 C8 113.04(19) . . ?
F6 C7 C8 112.21(12) . . ?
F6 C7 C8 112.21(12) 6_565 . ?
C9 C10 C17 119.10(19) . . ?
C9 C10 N11 115.95(19) . . ?
C17 C10 N11 124.9(2) . . ?
C3 C2 C1 119.8(2) . . ?
C13 C14 C15 121.0(2) . . ?
N11 C12 C1 121.1(2) . . ?
O16 C15 C14 118.5(2) . . ?
O16 C15 C1 121.7(2) . . ?
C14 C15 C1 119.7(2) . . ?
C18 C17 C10 119.8(2) . . ?
C14 C13 C3 118.8(2) . . ?
C17 C18 C19 121.3(2) . . ?
C8 C19 C18 118.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O21 N4 C3 C2 0.000(1) . . . . ?
O5 N4 C3 C2 180.000(0) . . . . ?
O21 N4 C3 C13 180.000(0) . . . . ?
O5 N4 C3 C13 0.000(0) . . . . ?
C19 C8 C9 C10 0.000(1) . . . . ?
C7 C8 C9 C10 180.000(1) . . . . ?
C19 C8 C7 F20 0.000(1) . . . . ?
C9 C8 C7 F20 180.000(1) . . . . ?
C19 C8 C7 F6 -120.83(14) . . . . ?
C9 C8 C7 F6 59.17(14) . . . . ?
C19 C8 C7 F6 120.83(14) . . . 6_565 ?
C9 C8 C7 F6 -59.17(14) . . . 6_565 ?
C8 C9 C10 C17 0.000(1) . . . . ?
C8 C9 C10 N11 180.000(1) . . . . ?
C12 N11 C10 C9 180.000(1) . . . . ?
C12 N11 C10 C17 0.000(1) . . . . ?
C13 C3 C2 C1 0.000(1) . . . . ?
N4 C3 C2 C1 180.000(0) . . . . ?
C15 C1 C2 C3 0.000(1) . . . . ?
C12 C1 C2 C3 180.000(0) . . . . ?
C10 N11 C12 C1 180.000(1) . . . . ?
C2 C1 C12 N11 180.000(1) . . . . ?
C15 C1 C12 N11 0.000(1) . . . . ?
C13 C14 C15 O16 180.000(0) . . . . ?
C13 C14 C15 C1 0.000(1) . . . . ?
C2 C1 C15 O16 180.000(0) . . . . ?
C12 C1 C15 O16 0.000(1) . . . . ?
C2 C1 C15 C14 0.000(1) . . . . ?
C12 C1 C15 C14 180.000(0) . . . . ?
C9 C10 C17 C18 0.000(1) . . . . ?
N11 C10 C17 C18 180.000(1) . . . . ?
C15 C14 C13 C3 0.000(0) . . . . ?
C2 C3 C13 C14 0.000(1) . . . . ?
N4 C3 C13 C14 180.000(0) . . . . ?
C10 C17 C18 C19 0.000(1) . . . . ?
C9 C8 C19 C18 0.000(1) . . . . ?
C7 C8 C19 C18 180.000(1) . . . . ?
C17 C18 C19 C8 0.000(1) . . . . ?

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_SH01_210_auto
_database_code_depnum_ccdc_archive 'CCDC 2191110'
loop_
_audit_author_name
_audit_author_address
'Siya T. Hulushe'
;Rhodes University
South Africa
;
_audit_update_record             
;
2022-07-18 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 F1.50 N O1.50'
_chemical_formula_sum            'C7 H4 F1.50 N O1.50'
_chemical_formula_weight         154.61

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'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   14.3133(3)
_cell_length_b                   6.65740(10)
_cell_length_c                   14.1840(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.075(2)
_cell_angle_gamma                90
_cell_volume                     1292.01(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       platelets
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_F_000             628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.343
_exptl_crystal_size_mid          0.284
_exptl_crystal_size_min          0.212
_exptl_absorpt_coefficient_mu    1.243
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_diffrn_ambient_temperature      210(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6927
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.259
_diffrn_reflns_theta_max         78.915
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1461
_reflns_number_gt                1309
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0575P)²+1.1420P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1461
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1397
_refine_ls_wR_factor_gt          0.1372
_refine_ls_goodness_of_fit_ref   1.204
_refine_ls_restrained_S_all      1.204
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
F6 F 0.03858(9) 0.6590(2) 0.89051(9) 0.0634(4) Uani 1 1 d . . . . .
F20 F 0.12167(13) 0.500000 1.01835(11) 0.0708(6) Uani 1 2 d S T P . .
O16 O 0.08719(13) 0.500000 0.46162(14) 0.0557(6) Uani 1 2 d S T P . .
O5 O 0.36999(16) 0.500000 0.20244(13) 0.0560(6) Uani 1 2 d S T P . .
N11 N 0.21836(14) 0.500000 0.63476(13) 0.0338(5) Uani 1 2 d S T P . .
N4 N 0.39023(17) 0.500000 0.29186(15) 0.0438(5) Uani 1 2 d S T P . .
C9 C 0.16557(17) 0.500000 0.77897(16) 0.0334(5) Uani 1 2 d S T P . .
H9 H 0.101191 0.500000 0.736759 0.040 Uiso 1 2 calc R U P . .
C10 C 0.24318(17) 0.500000 0.73948(15) 0.0321(5) Uani 1 2 d S T P . .
C1 C 0.26002(17) 0.500000 0.48396(15) 0.0328(5) Uani 1 2 d S T P . .
H1 H 0.110(3) 0.500000 0.521(3) 0.069(11) Uiso 1 2 d S . P . .
C3 C 0.31171(18) 0.500000 0.33770(17) 0.0351(5) Uani 1 2 d S T P . .
C12 C 0.28496(17) 0.500000 0.59087(16) 0.0341(5) Uani 1 2 d S T P . .
H12 H 0.351047 0.500000 0.628547 0.041 Uiso 1 2 calc R U P . .
C8 C 0.18199(17) 0.500000 0.88065(16) 0.0353(5) Uani 1 2 d S T P . .
C2 C 0.33455(17) 0.500000 0.43919(16) 0.0355(5) Uani 1 2 d S T P . .
H2 H 0.400248 0.500000 0.478024 0.043 Uiso 1 2 calc R U P . .
C14 C 0.14187(19) 0.500000 0.32106(18) 0.0484(7) Uani 1 2 d S T P . .
H14 H 0.076574 0.500000 0.281118 0.058 Uiso 1 2 calc R U P . .
C15 C 0.16195(18) 0.500000 0.42352(17) 0.0395(6) Uani 1 2 d S T P . .
C13 C 0.21578(19) 0.500000 0.27778(17) 0.0413(6) Uani 1 2 d S T P . .
H13 H 0.201711 0.500000 0.208745 0.050 Uiso 1 2 calc R U P . .
C18 C 0.35395(19) 0.500000 0.90385(18) 0.0491(7) Uani 1 2 d S T P . .
H18 H 0.418238 0.500000 0.946256 0.059 Uiso 1 2 calc R U P . .
C7 C 0.09618(19) 0.500000 0.92059(17) 0.0415(6) Uani 1 2 d S T P . .
C17 C 0.33865(18) 0.500000 0.80322(17) 0.0416(6) Uani 1 2 d S T P . .
H17 H 0.392168 0.500000 0.777520 0.050 Uiso 1 2 calc R U P . .
O21 O 0.47398(16) 0.500000 0.34491(16) 0.0938(12) Uani 1 2 d S T P . .
C19 C 0.27636(19) 0.500000 0.94365(17) 0.0422(6) Uani 1 2 d S T P . .
H19 H 0.287663 0.500000 1.012365 0.051 Uiso 1 2 calc R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F6 C7 1.333(2) . ?
F20 C7 1.326(3) . ?
O16 C15 1.333(3) . ?
O5 N4 1.215(3) . ?
N11 C12 1.282(3) . ?
N11 C10 1.422(3) . ?
N4 O21 1.214(3) . ?
N4 C3 1.454(3) . ?
C9 C10 1.383(3) . ?
C9 C8 1.392(3) . ?
C10 C17 1.400(3) . ?
C1 C2 1.392(3) . ?
C1 C15 1.414(3) . ?
C1 C12 1.452(3) . ?
C3 C2 1.379(3) . ?
C3 C13 1.387(4) . ?
C8 C19 1.383(3) . ?
C8 C7 1.496(3) . ?
C14 C13 1.370(4) . ?
C14 C15 1.396(3) . ?
C18 C17 1.379(3) . ?
C18 C19 1.386(4) . ?

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 N11 C10 120.9(2) . . ?
O21 N4 O5 122.4(2) . . ?
O21 N4 C3 118.4(2) . . ?
O5 N4 C3 119.2(2) . . ?
C10 C9 C8 120.6(2) . . ?
C9 C10 C17 119.1(2) . . ?
C9 C10 N11 116.0(2) . . ?
C17 C10 N11 124.9(2) . . ?
C2 C1 C15 118.7(2) . . ?
C2 C1 C12 119.3(2) . . ?
C15 C1 C12 121.9(2) . . ?
C2 C3 C13 121.9(2) . . ?
C2 C3 N4 119.3(2) . . ?
C13 C3 N4 118.8(2) . . ?
N11 C12 C1 121.1(2) . . ?
C19 C8 C9 120.3(2) . . ?
C19 C8 C7 120.7(2) . . ?
C9 C8 C7 119.0(2) . . ?
C3 C2 C1 119.8(2) . . ?
C13 C14 C15 121.1(2) . . ?
O16 C15 C14 118.5(2) . . ?
O16 C15 C1 121.8(2) . . ?
C14 C15 C1 119.7(2) . . ?
C14 C13 C3 118.8(2) . . ?
C17 C18 C19 121.3(2) . . ?
F20 C7 F6 106.81(14) . . ?
F20 C7 F6 106.80(14) . 6_565 ?
F6 C7 F6 105.2(2) . 6_565 ?
F20 C7 C8 113.0(2) . . ?
F6 C7 C8 112.23(13) . . ?
F6 C7 C8 112.23(13) 6_565 . ?
C18 C17 C10 119.8(2) . . ?
C8 C19 C18 119.0(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C9 C10 C17 0.000(1) . . . . ?
C8 C9 C10 N11 180.000(1) . . . . ?
C12 N11 C10 C9 180.000(1) . . . . ?
C12 N11 C10 C17 0.000(1) . . . . ?
O21 N4 C3 C2 0.000(1) . . . . ?
O5 N4 C3 C2 180.000(0) . . . . ?
O21 N4 C3 C13 180.000(0) . . . . ?
O5 N4 C3 C13 0.000(0) . . . . ?
C10 N11 C12 C1 180.000(1) . . . . ?
C2 C1 C12 N11 180.000(1) . . . . ?
C15 C1 C12 N11 0.000(1) . . . . ?
C10 C9 C8 C19 0.000(1) . . . . ?
C10 C9 C8 C7 180.000(1) . . . . ?
C13 C3 C2 C1 0.000(1) . . . . ?
N4 C3 C2 C1 180.000(0) . . . . ?
C15 C1 C2 C3 0.000(1) . . . . ?
C12 C1 C2 C3 180.000(1) . . . . ?
C13 C14 C15 O16 180.000(0) . . . . ?
C13 C14 C15 C1 0.000(1) . . . . ?
C2 C1 C15 O16 180.000(0) . . . . ?
C12 C1 C15 O16 0.000(1) . . . . ?
C2 C1 C15 C14 0.000(1) . . . . ?
C12 C1 C15 C14 180.000(0) . . . . ?
C15 C14 C13 C3 0.000(1) . . . . ?
C2 C3 C13 C14 0.000(1) . . . . ?
N4 C3 C13 C14 180.000(0) . . . . ?
C19 C8 C7 F20 0.000(1) . . . . ?
C9 C8 C7 F20 180.000(1) . . . . ?
C19 C8 C7 F6 120.88(15) . . . . ?
C9 C8 C7 F6 -59.12(15) . . . . ?
C19 C8 C7 F6 -120.88(15) . . . 6_565 ?
C9 C8 C7 F6 59.12(15) . . . 6_565 ?
C19 C18 C17 C10 0.000(1) . . . . ?
C9 C10 C17 C18 0.000(1) . . . . ?
N11 C10 C17 C18 180.000(1) . . . . ?
C9 C8 C19 C18 0.000(1) . . . . ?
C7 C8 C19 C18 180.000(1) . . . . ?
C17 C18 C19 C8 0.000(1) . . . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_SH01_240_auto
_database_code_depnum_ccdc_archive 'CCDC 2191111'
loop_
_audit_author_name
_audit_author_address
'Siya T. Hulushe'
;Rhodes University
South Africa
;
_audit_update_record             
;
2022-07-18 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 F1.50 N O1.50'
_chemical_formula_sum            'C7 H4 F1.50 N O1.50'
_chemical_formula_weight         154.61

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'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   14.3118(4)
_cell_length_b                   6.6925(2)
_cell_length_c                   14.1987(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.993(3)
_cell_angle_gamma                90
_cell_volume                     1300.60(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       platelets
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_F_000             628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.343
_exptl_crystal_size_mid          0.284
_exptl_crystal_size_min          0.212
_exptl_absorpt_coefficient_mu    1.235
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_diffrn_ambient_temperature      240(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6938
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.255
_diffrn_reflns_theta_max         78.899
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1483
_reflns_number_gt                1299
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0420P)²+2.1250P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1483
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1495
_refine_ls_wR_factor_gt          0.1475
_refine_ls_goodness_of_fit_ref   1.214
_refine_ls_restrained_S_all      1.214
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
F6 F 0.96074(12) 0.6573(3) 0.10932(12) 0.0749(6) Uani 1 1 d . . . . .
F20 F 0.87780(17) 0.500000 -0.01784(14) 0.0832(9) Uani 1 2 d S T P . .
O16 O 0.91258(17) 0.500000 0.53832(19) 0.0649(9) Uani 1 2 d S T P . .
O5 O 0.6301(2) 0.500000 0.79743(17) 0.0650(8) Uani 1 2 d S T P . .
N11 N 0.78158(18) 0.500000 0.36550(17) 0.0383(6) Uani 1 2 d S T P . .
N4 N 0.6098(2) 0.500000 0.7083(2) 0.0507(7) Uani 1 2 d S T P . .
C9 C 0.8340(2) 0.500000 0.2212(2) 0.0383(7) Uani 1 2 d S T P . .
H9 H 0.898413 0.500000 0.263181 0.046 Uiso 1 2 calc R U P . .
C10 C 0.7565(2) 0.500000 0.2610(2) 0.0361(7) Uani 1 2 d S T P . .
C1 C 0.7400(2) 0.500000 0.5163(2) 0.0370(7) Uani 1 2 d S T P . .
H1 H 0.891(3) 0.500000 0.481(3) 0.076(15) Uiso 1 2 d S . P . .
C3 C 0.6886(2) 0.500000 0.6625(2) 0.0403(7) Uani 1 2 d S T P . .
C2 C 0.6657(2) 0.500000 0.5611(2) 0.0406(7) Uani 1 2 d S T P . .
H2 H 0.599961 0.500000 0.522435 0.049 Uiso 1 2 calc R U P . .
C12 C 0.7152(2) 0.500000 0.4096(2) 0.0393(7) Uani 1 2 d S T P . .
H12 H 0.649091 0.500000 0.372080 0.047 Uiso 1 2 calc R U P . .
C14 C 0.8579(3) 0.500000 0.6786(2) 0.0572(10) Uani 1 2 d S T P . .
H14 H 0.923216 0.500000 0.718426 0.069 Uiso 1 2 calc R U P . .
C8 C 0.8175(2) 0.500000 0.1196(2) 0.0406(7) Uani 1 2 d S T P . .
C15 C 0.8377(2) 0.500000 0.5765(2) 0.0459(8) Uani 1 2 d S T P . .
C13 C 0.7839(3) 0.500000 0.7218(2) 0.0470(8) Uani 1 2 d S T P . .
H13 H 0.797912 0.500000 0.790695 0.056 Uiso 1 2 calc R U P . .
C18 C 0.6458(2) 0.500000 0.0972(2) 0.0571(10) Uani 1 2 d S T P . .
H18 H 0.581518 0.500000 0.054996 0.069 Uiso 1 2 calc R U P . .
C7 C 0.9031(3) 0.500000 0.0797(2) 0.0490(9) Uani 1 2 d S T P . .
C17 C 0.6613(2) 0.500000 0.1976(2) 0.0483(9) Uani 1 2 d S T P . .
H17 H 0.607841 0.500000 0.223380 0.058 Uiso 1 2 calc R U P . .
O21 O 0.5264(2) 0.500000 0.6555(2) 0.1050(16) Uani 1 2 d S T P . .
C19 C 0.7234(2) 0.500000 0.0574(2) 0.0490(9) Uani 1 2 d S T P . .
H19 H 0.712022 0.500000 -0.011246 0.059 Uiso 1 2 calc R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F6 C7 1.328(3) . ?
F20 C7 1.325(3) . ?
O16 C15 1.335(4) . ?
O5 N4 1.213(3) . ?
N11 C12 1.282(4) . ?
N11 C10 1.421(3) . ?
N4 O21 1.210(4) . ?
N4 C3 1.458(4) . ?
C9 C10 1.384(4) . ?
C9 C8 1.391(4) . ?
C10 C17 1.397(4) . ?
C1 C2 1.391(4) . ?
C1 C15 1.409(4) . ?
C1 C12 1.452(4) . ?
C3 C13 1.378(5) . ?
C3 C2 1.380(4) . ?
C14 C13 1.370(5) . ?
C14 C15 1.393(4) . ?
C8 C19 1.378(4) . ?
C8 C7 1.494(4) . ?
C18 C17 1.376(4) . ?
C18 C19 1.386(5) . ?

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 N11 C10 120.9(3) . . ?
O21 N4 O5 122.7(3) . . ?
O21 N4 C3 118.3(3) . . ?
O5 N4 C3 119.0(3) . . ?
C10 C9 C8 120.6(3) . . ?
C9 C10 C17 119.0(3) . . ?
C9 C10 N11 116.0(3) . . ?
C17 C10 N11 125.0(3) . . ?
C2 C1 C15 118.6(3) . . ?
C2 C1 C12 119.4(3) . . ?
C15 C1 C12 122.0(3) . . ?
C13 C3 C2 121.9(3) . . ?
C13 C3 N4 119.0(3) . . ?
C2 C3 N4 119.1(3) . . ?
C3 C2 C1 119.8(3) . . ?
N11 C12 C1 121.3(3) . . ?
C13 C14 C15 120.8(3) . . ?
C19 C8 C9 120.2(3) . . ?
C19 C8 C7 120.8(3) . . ?
C9 C8 C7 118.9(3) . . ?
O16 C15 C14 118.4(3) . . ?
O16 C15 C1 121.7(3) . . ?
C14 C15 C1 119.9(3) . . ?
C14 C13 C3 119.0(3) . . ?
C17 C18 C19 121.1(3) . . ?
F20 C7 F6 106.63(19) . . ?
F20 C7 F6 106.63(19) . 6_565 ?
F6 C7 F6 104.9(3) . 6_565 ?
F20 C7 C8 113.1(3) . . ?
F6 C7 C8 112.47(18) . . ?
F6 C7 C8 112.47(18) 6_565 . ?
C18 C17 C10 119.9(3) . . ?
C8 C19 C18 119.2(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
C8 C9 C10 C17 0.000(0) . . . . ?
C8 C9 C10 N11 180.000(0) . . . . ?
C12 N11 C10 C9 180.000(0) . . . . ?
C12 N11 C10 C17 0.000(1) . . . . ?
O21 N4 C3 C13 180.000(1) . . . . ?
O5 N4 C3 C13 0.000(1) . . . . ?
O21 N4 C3 C2 0.000(1) . . . . ?
O5 N4 C3 C2 180.000(1) . . . . ?
C13 C3 C2 C1 0.000(1) . . . . ?
N4 C3 C2 C1 180.000(1) . . . . ?
C15 C1 C2 C3 0.000(1) . . . . ?
C12 C1 C2 C3 180.000(1) . . . . ?
C10 N11 C12 C1 180.000(1) . . . . ?
C2 C1 C12 N11 180.000(1) . . . . ?
C15 C1 C12 N11 0.000(1) . . . . ?
C10 C9 C8 C19 0.000(0) . . . . ?
C10 C9 C8 C7 180.000(0) . . . . ?
C13 C14 C15 O16 180.000(1) . . . . ?
C13 C14 C15 C1 0.000(1) . . . . ?
C2 C1 C15 O16 180.000(1) . . . . ?
C12 C1 C15 O16 0.000(1) . . . . ?
C2 C1 C15 C14 0.000(1) . . . . ?
C12 C1 C15 C14 180.000(1) . . . . ?
C15 C14 C13 C3 0.000(1) . . . . ?
C2 C3 C13 C14 0.000(1) . . . . ?
N4 C3 C13 C14 180.000(1) . . . . ?
C19 C8 C7 F20 0.000(0) . . . . ?
C9 C8 C7 F20 180.000(0) . . . . ?
C19 C8 C7 F6 120.9(2) . . . . ?
C9 C8 C7 F6 -59.1(2) . . . . ?
C19 C8 C7 F6 -120.9(2) . . . 6_565 ?
C9 C8 C7 F6 59.1(2) . . . 6_565 ?
C19 C18 C17 C10 0.000(0) . . . . ?
C9 C10 C17 C18 0.000(0) . . . . ?
N11 C10 C17 C18 180.000(0) . . . . ?
C9 C8 C19 C18 0.000(0) . . . . ?
C7 C8 C19 C18 180.000(0) . . . . ?
C17 C18 C19 C8 0.000(0) . . . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_SH01_270_auto
_database_code_depnum_ccdc_archive 'CCDC 2191112'
loop_
_audit_author_name
_audit_author_address
'Siya T. Hulushe'
;Rhodes University
South Africa
;
_audit_update_record             
;
2022-07-18 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 F1.50 N O1.50'
_chemical_formula_sum            'C7 H4 F1.50 N O1.50'
_chemical_formula_weight         154.61

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'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   14.3128(6)
_cell_length_b                   6.7327(2)
_cell_length_c                   14.2071(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.952(4)
_cell_angle_gamma                90
_cell_volume                     1309.56(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       platelets
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_F_000             628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.343
_exptl_crystal_size_mid          0.284
_exptl_crystal_size_min          0.212
_exptl_absorpt_coefficient_mu    1.227
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_diffrn_ambient_temperature      270(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6685
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.252
_diffrn_reflns_theta_max         78.712
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1476
_reflns_number_gt                1251
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0363P)²+2.5176P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1476
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.1616
_refine_ls_wR_factor_gt          0.1574
_refine_ls_goodness_of_fit_ref   1.261
_refine_ls_restrained_S_all      1.261
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
F6 F 0.03985(14) 0.3443(4) 0.89075(15) 0.0869(7) Uani 1 1 d . . . . .
F20 F 0.1229(2) 0.500000 1.01727(17) 0.0974(12) Uani 1 2 d S T P . .
N11 N 0.2186(2) 0.500000 0.63421(19) 0.0429(7) Uani 1 2 d S T P . .
O16 O 0.0876(2) 0.500000 0.4618(2) 0.0747(11) Uani 1 2 d S T P . .
O5 O 0.3701(3) 0.500000 0.2026(2) 0.0744(10) Uani 1 2 d S T P . .
N4 N 0.3902(3) 0.500000 0.2917(2) 0.0580(9) Uani 1 2 d S T P . .
C9 C 0.1664(3) 0.500000 0.7786(2) 0.0434(9) Uani 1 2 d S T P . .
H9 H 0.102703 0.500000 0.737262 0.052 Uiso 1 2 calc R U P . .
C10 C 0.2435(3) 0.500000 0.7386(2) 0.0409(8) Uani 1 2 d S T P . .
C1 C 0.2600(3) 0.500000 0.4834(2) 0.0412(8) Uani 1 2 d S T P . .
H1 H 0.110(4) 0.500000 0.520(4) 0.084(18) Uiso 1 2 d S . P . .
C3 C 0.3115(3) 0.500000 0.3373(3) 0.0448(9) Uani 1 2 d S T P . .
C8 C 0.1829(3) 0.500000 0.8799(2) 0.0457(9) Uani 1 2 d S T P . .
C12 C 0.2846(3) 0.500000 0.5900(2) 0.0448(9) Uani 1 2 d S T P . .
H12 H 0.350009 0.500000 0.627028 0.054 Uiso 1 2 calc R U P . .
C2 C 0.3339(3) 0.500000 0.4384(3) 0.0462(9) Uani 1 2 d S T P . .
H2 H 0.398874 0.500000 0.476695 0.055 Uiso 1 2 calc R U P . .
C14 C 0.1423(3) 0.500000 0.3215(3) 0.0650(13) Uani 1 2 d S T P . .
H14 H 0.077720 0.500000 0.282167 0.078 Uiso 1 2 calc R U P . .
C13 C 0.2163(3) 0.500000 0.2785(3) 0.0546(10) Uani 1 2 d S T P . .
H13 H 0.202407 0.500000 0.210335 0.065 Uiso 1 2 calc R U P . .
C18 C 0.3543(3) 0.500000 0.9017(3) 0.0648(13) Uani 1 2 d S T P . .
H18 H 0.417973 0.500000 0.943289 0.078 Uiso 1 2 calc R U P . .
C15 C 0.1624(3) 0.500000 0.4235(3) 0.0517(10) Uani 1 2 d S T P . .
C7 C 0.0977(3) 0.500000 0.9202(3) 0.0557(11) Uani 1 2 d S T P . .
C17 C 0.3387(3) 0.500000 0.8015(3) 0.0544(11) Uani 1 2 d S T P . .
H17 H 0.391448 0.500000 0.775825 0.065 Uiso 1 2 calc R U P . .
O21 O 0.4734(2) 0.500000 0.3442(2) 0.118(2) Uani 1 2 d S T P . .
C19 C 0.2770(3) 0.500000 0.9417(3) 0.0559(11) Uani 1 2 d S T P . .
H19 H 0.288487 0.500000 1.009570 0.067 Uiso 1 2 calc R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F6 C7 1.326(3) . ?
F20 C7 1.319(4) . ?
N11 C12 1.278(5) . ?
N11 C10 1.420(4) . ?
O16 C15 1.335(5) . ?
O5 N4 1.213(4) . ?
N4 O21 1.208(5) . ?
N4 C3 1.454(5) . ?
C9 C10 1.382(5) . ?
C9 C8 1.389(4) . ?
C10 C17 1.394(5) . ?
C1 C2 1.386(5) . ?
C1 C15 1.408(5) . ?
C1 C12 1.452(4) . ?
C3 C13 1.375(5) . ?
C3 C2 1.378(5) . ?
C8 C19 1.377(5) . ?
C8 C7 1.491(5) . ?
C14 C13 1.370(6) . ?
C14 C15 1.393(5) . ?
C18 C17 1.374(5) . ?
C18 C19 1.384(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
C12 N11 C10 121.1(3) . . ?
O21 N4 O5 122.4(4) . . ?
O21 N4 C3 118.5(3) . . ?
O5 N4 C3 119.1(4) . . ?
C10 C9 C8 120.8(3) . . ?
C9 C10 C17 118.9(3) . . ?
C9 C10 N11 116.3(3) . . ?
C17 C10 N11 124.8(3) . . ?
C2 C1 C15 118.6(3) . . ?
C2 C1 C12 119.7(3) . . ?
C15 C1 C12 121.8(3) . . ?
C13 C3 C2 121.4(3) . . ?
C13 C3 N4 119.2(3) . . ?
C2 C3 N4 119.4(3) . . ?
C19 C8 C9 120.0(3) . . ?
C19 C8 C7 120.9(3) . . ?
C9 C8 C7 119.2(3) . . ?
N11 C12 C1 121.5(3) . . ?
C3 C2 C1 120.3(3) . . ?
C13 C14 C15 120.8(4) . . ?
C14 C13 C3 119.2(3) . . ?
C17 C18 C19 121.1(4) . . ?
O16 C15 C14 118.5(3) . . ?
O16 C15 C1 121.8(3) . . ?
C14 C15 C1 119.8(3) . . ?
F20 C7 F6 106.6(2) . . ?
F20 C7 F6 106.6(2) . 6_565 ?
F6 C7 F6 104.5(4) . 6_565 ?
F20 C7 C8 113.4(3) . . ?
F6 C7 C8 112.6(2) . . ?
F6 C7 C8 112.6(2) 6_565 . ?
C18 C17 C10 119.9(4) . . ?
C8 C19 C18 119.3(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
C8 C9 C10 C17 0.000(2) . . . . ?
C8 C9 C10 N11 180.000(1) . . . . ?
C12 N11 C10 C9 180.000(1) . . . . ?
C12 N11 C10 C17 0.000(2) . . . . ?
O21 N4 C3 C13 180.000(1) . . . . ?
O5 N4 C3 C13 0.000(1) . . . . ?
O21 N4 C3 C2 0.000(1) . . . . ?
O5 N4 C3 C2 180.000(1) . . . . ?
C10 C9 C8 C19 0.000(2) . . . . ?
C10 C9 C8 C7 180.000(1) . . . . ?
C10 N11 C12 C1 180.000(1) . . . . ?
C2 C1 C12 N11 180.000(1) . . . . ?
C15 C1 C12 N11 0.000(1) . . . . ?
C13 C3 C2 C1 0.000(1) . . . . ?
N4 C3 C2 C1 180.000(1) . . . . ?
C15 C1 C2 C3 0.000(1) . . . . ?
C12 C1 C2 C3 180.000(1) . . . . ?
C15 C14 C13 C3 0.000(1) . . . . ?
C2 C3 C13 C14 0.000(1) . . . . ?
N4 C3 C13 C14 180.000(1) . . . . ?
C13 C14 C15 O16 180.000(1) . . . . ?
C13 C14 C15 C1 0.000(1) . . . . ?
C2 C1 C15 O16 180.000(1) . . . . ?
C12 C1 C15 O16 0.000(1) . . . . ?
C2 C1 C15 C14 0.000(1) . . . . ?
C12 C1 C15 C14 180.000(1) . . . . ?
C19 C8 C7 F20 0.000(2) . . . . ?
C9 C8 C7 F20 180.000(1) . . . . ?
C19 C8 C7 F6 -121.1(2) . . . . ?
C9 C8 C7 F6 58.9(2) . . . . ?
C19 C8 C7 F6 121.1(2) . . . 6_565 ?
C9 C8 C7 F6 -58.9(2) . . . 6_565 ?
C19 C18 C17 C10 0.000(2) . . . . ?
C9 C10 C17 C18 0.000(2) . . . . ?
N11 C10 C17 C18 180.000(1) . . . . ?
C9 C8 C19 C18 0.000(2) . . . . ?
C7 C8 C19 C18 180.000(2) . . . . ?
C17 C18 C19 C8 0.000(2) . . . . ?

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_sh01_300_auto
_database_code_depnum_ccdc_archive 'CCDC 2191113'
loop_
_audit_author_name
_audit_author_address
'Siya T. Hulushe'
;Rhodes University
South Africa
;
_audit_update_record             
;
2022-07-18 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2021-04-07
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H4.5 F1.5 N O1.5'
_chemical_formula_sum            'C7 H4 F1.50 N O1.50'
_chemical_formula_weight         154.61
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
F F 0.0727 0.0534 '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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   14.3168(6)
_cell_length_b                   6.7716(3)
_cell_length_c                   14.2320(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.790(4)
_cell_angle_gamma                90
_cell_volume                     1320.94(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4246
_cell_measurement_temperature    299.97(12)
_cell_measurement_theta_max      77.4950
_cell_measurement_theta_min      3.2120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.216
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.97a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       platelets
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.343
_exptl_crystal_size_mid          0.284
_exptl_crystal_size_min          0.212
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6419
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         83.762
_diffrn_reflns_theta_min         3.244
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.97(12)
_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 0.901
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00 119.00   0.50    0.28    --   46.82  42.00  32.00  168
  2  ω     24.00 120.00   0.50    0.28    --   46.82  77.00  90.00  192
  3  ω     24.00 118.00   0.50    0.28    --   46.82  77.00 -60.00  188
  4  ω     79.00 178.00   0.50    1.13    --  110.25 125.00-120.00  198
  5  ω     98.00 178.00   0.50    1.13    --  110.25  42.00  32.00  160
  6  ω    -27.00  13.00   0.50    0.28    --   46.82 -19.00  60.00   80
  7  ω    -25.00  48.00   0.50    0.28    --   46.82 -42.00-119.00  146
  8  ω     38.00  80.00   0.50    1.13    --  110.25 -61.00 -60.00   84
  9  ω     38.00  80.00   0.50    1.13    --  110.25 -61.00-120.00   84
 10  ω     38.00  80.00   0.50    1.13    --  110.25 -61.00-180.00   84
 11  ω     38.00 106.00   0.50    1.13    --  110.25 -94.00-180.00  136
 12  ω     38.00 111.00   0.50    1.13    --  110.25-125.00-180.00  146
 13  ω     38.00 106.00   0.50    1.13    --  110.25 -94.00-120.00  136
 14  ω     38.00 106.00   0.50    1.13    --  110.25 -94.00 -60.00  136
 15  ω     38.00 111.00   0.50    1.13    --  110.25-125.00  30.00  146
 16  ω    -40.00  25.00   0.50    0.28    --  -46.82  42.00  32.00  130
 17  ω     -5.00  29.00   0.50    0.28    --  -46.82  19.00 150.00   68
 18  ω     -5.00  29.00   0.50    0.28    --  -46.82  19.00-150.00   68
 19  ω     -5.00  29.00   0.50    0.28    --  -46.82  19.00-180.00   68
 20  ω   -119.00 -24.00   0.50    0.28    --  -46.82 -77.00-180.00  190
 21  ω   -174.00 -89.00   0.50    1.13    -- -102.00 -42.00-119.00  170
 22  ω   -119.00 -34.00   0.50    0.28    --  -46.82 -42.00-119.00  170
 23  ω   -174.00 -89.00   0.50    1.13    -- -102.00 -45.00 150.00  170
 24  ω    -72.00 -29.00   0.50    1.13    -- -102.00  61.00  60.00   86
 25  ω    -72.00 -29.00   0.50    1.13    -- -102.00  61.00 120.00   86
 26  ω    -72.00 -29.00   0.50    1.13    -- -102.00  61.00 150.00   86
 27  ω   -125.00 -29.00   0.50    1.13    -- -102.00  77.00  60.00  192
 28  ω    -72.00 -29.00   0.50    1.13    -- -102.00  61.00-150.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0597759000
_diffrn_orient_matrix_UB_12      -0.0795797000
_diffrn_orient_matrix_UB_13      -0.1008986000
_diffrn_orient_matrix_UB_21      -0.0944711000
_diffrn_orient_matrix_UB_22      0.0748930000
_diffrn_orient_matrix_UB_23      0.0191172000
_diffrn_orient_matrix_UB_31      0.0117094000
_diffrn_orient_matrix_UB_32      0.1995032000
_diffrn_orient_matrix_UB_33      -0.0473329000
_diffrn_oxdiff_digest_frames     
;
01f203b30d18f3ebd198937fdf4ca71d820005189e0
;
_diffrn_oxdiff_digest_hkl        
;
0146843d9690de31a3e2cd2921f9e33b6824e5
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1180
_reflns_number_total             1460
_reflns_odcompleteness_completeness 98.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.41.97a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.97a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.97a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1460
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0655
_refine_ls_restrained_S_all      1.183
_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)+(0.1432P)²+0.2926P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2135
_refine_ls_wR_factor_ref         0.2377
_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:
 C12(H12), C18(H18), C9(H9), C2(H2), C14(H14), C13(H13), C17(H17), C19(H19)
;
_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
F6 F 0.04059(13) 0.3457(3) 0.89104(13) 0.1085(7) Uani 1 1 d . . . . .
N11 N 0.21877(16) 0.500000 0.63409(15) 0.0576(6) Uani 1 2 d S T P . .
F20 F 0.12362(18) 0.500000 1.01708(14) 0.1178(10) Uani 1 2 d S T P . .
O16 O 0.08802(16) 0.500000 0.46218(17) 0.0921(9) Uani 1 2 d S T P . .
O5 O 0.3701(2) 0.500000 0.20307(16) 0.0925(8) Uani 1 2 d S T P . .
N4 N 0.3897(2) 0.500000 0.29117(19) 0.0744(8) Uani 1 2 d S T P . .
C3 C 0.3112(2) 0.500000 0.3374(2) 0.0602(7) Uani 1 2 d S T P . .
C10 C 0.24382(19) 0.500000 0.73792(18) 0.0553(6) Uani 1 2 d S T P . .
C8 C 0.1835(2) 0.500000 0.87916(18) 0.0608(7) Uani 1 2 d S T P . .
C1 C 0.2595(2) 0.500000 0.48330(18) 0.0558(7) Uani 1 2 d S T P . .
C12 C 0.2843(2) 0.500000 0.58921(19) 0.0584(7) Uani 1 2 d S T P . .
H12 H 0.349695 0.500000 0.625683 0.070 Uiso 1 2 calc RS T P . .
C15 C 0.1628(2) 0.500000 0.4236(2) 0.0675(8) Uani 1 2 d S T P . .
C18 C 0.3551(2) 0.500000 0.9012(2) 0.0818(10) Uani 1 2 d S T P . .
H18 H 0.418767 0.500000 0.942384 0.098 Uiso 1 2 calc RS T P . .
O21 O 0.4736(2) 0.500000 0.3439(2) 0.1394(17) Uani 1 2 d S T P . .
C9 C 0.1666(2) 0.500000 0.77810(18) 0.0571(7) Uani 1 2 d S T P . .
H9 H 0.102849 0.500000 0.737097 0.069 Uiso 1 2 calc RS T P . .
C2 C 0.3338(2) 0.500000 0.43782(19) 0.0605(7) Uani 1 2 d S T P . .
H2 H 0.398744 0.500000 0.475690 0.073 Uiso 1 2 calc RS T P . .
C14 C 0.1426(2) 0.500000 0.3218(2) 0.0813(10) Uani 1 2 d S T P . .
H14 H 0.078113 0.500000 0.282805 0.098 Uiso 1 2 calc RS T P . .
C13 C 0.2168(2) 0.500000 0.27821(19) 0.0703(8) Uani 1 2 d S T P . .
H13 H 0.203148 0.500000 0.210234 0.084 Uiso 1 2 calc RS T P . .
C7 C 0.0979(2) 0.500000 0.9200(2) 0.0706(8) Uani 1 2 d S T P . .
C17 C 0.3386(2) 0.500000 0.8008(2) 0.0702(8) Uani 1 2 d S T P . .
H17 H 0.391275 0.500000 0.774864 0.084 Uiso 1 2 calc RS T P . .
C19 C 0.2771(2) 0.500000 0.9414(2) 0.0712(8) Uani 1 2 d S T P . .
H19 H 0.288159 0.500000 1.009077 0.085 Uiso 1 2 calc RS T P . .
H20 H 0.110(3) 0.500000 0.528(3) 0.096(12) Uiso 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F6 C7 1.319(3) . ?
N11 C10 1.416(3) . ?
N11 C12 1.279(4) . ?
F20 C7 1.324(3) . ?
O16 C15 1.337(4) . ?
O5 N4 1.203(3) . ?
N4 C3 1.457(4) . ?
N4 O21 1.218(4) . ?
C3 C2 1.371(4) . ?
C3 C13 1.372(4) . ?
C10 C9 1.384(4) . ?
C10 C17 1.394(4) . ?
C8 C9 1.388(3) . ?
C8 C7 1.501(4) . ?
C8 C19 1.376(4) . ?
C1 C12 1.445(3) . ?
C1 C15 1.400(4) . ?
C1 C2 1.396(4) . ?
C15 C14 1.392(4) . ?
C18 C17 1.379(4) . ?
C18 C19 1.394(5) . ?
C14 C13 1.376(4) . ?

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 N11 C10 121.3(2) . . ?
O5 N4 C3 119.5(3) . . ?
O5 N4 O21 122.3(3) . . ?
O21 N4 C3 118.2(2) . . ?
C2 C3 N4 119.4(3) . . ?
C2 C3 C13 122.3(3) . . ?
C13 C3 N4 118.3(2) . . ?
C9 C10 N11 116.1(2) . . ?
C9 C10 C17 118.8(2) . . ?
C17 C10 N11 125.2(2) . . ?
C9 C8 C7 118.9(3) . . ?
C19 C8 C9 120.9(2) . . ?
C19 C8 C7 120.2(2) . . ?
C15 C1 C12 122.4(2) . . ?
C2 C1 C12 119.5(2) . . ?
C2 C1 C15 118.1(2) . . ?
N11 C12 C1 121.8(3) . . ?
O16 C15 C1 121.3(3) . . ?
O16 C15 C14 118.5(3) . . ?
C14 C15 C1 120.2(3) . . ?
C17 C18 C19 120.5(3) . . ?
C10 C9 C8 120.4(2) . . ?
C3 C2 C1 120.1(3) . . ?
C13 C14 C15 120.9(3) . . ?
C3 C13 C14 118.4(2) . . ?
F6 C7 F6 104.8(3) 6_565 . ?
F6 C7 F20 106.64(17) . . ?
F6 C7 F20 106.64(17) 6_565 . ?
F6 C7 C8 112.54(15) . . ?
F6 C7 C8 112.54(15) 6_565 . ?
F20 C7 C8 113.1(3) . . ?
C18 C17 C10 120.6(3) . . ?
C8 C19 C18 118.8(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 4.388
_oxdiff_exptl_absorpt_empirical_full_min 0.571
####################################################################### 
# 
# 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_SOLVE_1A_a
_database_code_depnum_ccdc_archive 'CCDC 2191114'
loop_
_audit_author_name
_audit_author_address
'Siya T. Hulushe'
;Rhodes University
South Africa
;
_audit_update_record             
;
2022-07-18 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        
2-((E)-(2-hydroxyphenyliminio)methyl)-4-nitrophenolate
_chemical_name_common            5-nitrosalicylaldehyde-o-aminophenol
_chemical_formula_moiety         'C13 H10 N2 O4'
_chemical_formula_sum            'C13 H10 N2 O4'
_chemical_compound_source        Synthesised
_exptl_crystal_recrystallization_method 'slow evaporation from ethanol'
_chemical_melting_point          ?
_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_diffrn_ambient_temperature      298(2)
_chemical_formula_weight         258.23

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration ?

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'

_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.
;

_cell_length_a                   6.3334(9)
_cell_length_b                   23.683(3)
_cell_length_c                   7.8211(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.769(5)
_cell_angle_gamma                90
_cell_volume                     1170.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2736
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      19.85
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.781
_exptl_crystal_size_mid          0.279
_exptl_crystal_size_min          0.116
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.918
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6490
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-IV CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.89
_diffrn_reflns_number            23657
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.1021
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.748
_diffrn_reflns_theta_max         21.308
_diffrn_reflns_theta_full        21.308
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1186
_reflns_number_gt                696
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Carbon-bound H atoms were placed in calculated positions and were included in
the refinement in the riding model approximation, with Uiso(H) set to
1.2 Ueq(C).

The nitrogen and oxygen-bound hydrogen atoms were located on a difference
Fourier map and refined freely.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1924P)²+1.2649P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1186
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1486
_refine_ls_R_factor_gt           0.0885
_refine_ls_wR_factor_ref         0.3586
_refine_ls_wR_factor_gt          0.2445
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_restrained_S_all      1.198
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.7381(10) 0.5593(3) 0.1642(8) 0.109(3) Uani 1 1 d . . . . .
O4 O 0.9726(11) 0.4339(3) 0.0519(9) 0.110(3) Uani 1 1 d . . . . .
O3 O -0.0836(11) 0.5837(3) 0.5483(9) 0.117(4) Uani 1 1 d . . . . .
O2 O -0.0139(11) 0.6712(3) 0.5015(9) 0.125(4) Uani 1 1 d . . . . .
N1 N 0.6209(11) 0.4550(3) 0.1865(8) 0.087(3) Uani 1 1 d . . . . .
N2 N 0.0249(13) 0.6203(4) 0.4882(10) 0.102(4) Uani 1 1 d . . . . .
C15 C 0.2112(13) 0.6048(4) 0.4012(10) 0.085(3) Uani 1 1 d . . . . .
C17 C 0.4204(14) 0.5331(4) 0.2867(10) 0.088(4) Uani 1 1 d . . . . .
C21 C 0.6650(14) 0.3974(4) 0.1518(10) 0.088(4) Uani 1 1 d . . . . .
C22 C 0.8567(14) 0.3870(4) 0.0775(11) 0.088(4) Uani 1 1 d . . . . .
C16 C 0.2409(14) 0.5495(4) 0.3679(10) 0.092(4) Uani 1 1 d . . . . .
H16 H 0.142875 0.522726 0.398736 0.111 Uiso 1 1 calc R U . . .
C12 C 0.5730(15) 0.5744(4) 0.2381(11) 0.093(4) Uani 1 1 d . . . . .
C1 C 0.4566(14) 0.4734(4) 0.2559(11) 0.096(4) Uani 1 1 d . . . . .
H1A H 0.356183 0.447480 0.287935 0.116 Uiso 1 1 calc R U . . .
C26 C 0.5378(16) 0.3535(4) 0.1873(12) 0.102(4) Uani 1 1 d . . . . .
H26 H 0.412341 0.360100 0.239464 0.122 Uiso 1 1 calc R U . . .
C14 C 0.3556(16) 0.6458(4) 0.3543(11) 0.102(4) Uani 1 1 d . . . . .
H14 H 0.330808 0.683546 0.378432 0.122 Uiso 1 1 calc R U . . .
C13 C 0.5294(15) 0.6314(4) 0.2749(12) 0.103(4) Uani 1 1 d . . . . .
H13 H 0.622415 0.659371 0.243667 0.124 Uiso 1 1 calc R U . . .
C23 C 0.9077(17) 0.3325(5) 0.0385(12) 0.105(4) Uani 1 1 d . . . . .
H23 H 1.034694 0.325126 -0.010477 0.126 Uiso 1 1 calc R U . . .
C24 C 0.7771(17) 0.2894(4) 0.0699(13) 0.116(4) Uani 1 1 d . . . . .
H24 H 0.812284 0.252807 0.039246 0.139 Uiso 1 1 calc R U . . .
C25 C 0.5939(18) 0.2993(4) 0.1463(13) 0.122(4) Uani 1 1 d . . . . .
H25 H 0.506087 0.269297 0.170855 0.147 Uiso 1 1 calc R U . . .
H1 H 0.756(16) 0.494(4) 0.140(11) 0.14(3) Uiso 1 1 d . . . . .
H4 H 1.090(17) 0.426(5) -0.010(13) 0.14(4) 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
O1 C12 1.278(10) . ?
O4 C22 1.353(10) . ?
O4 H4 0.93(11) . ?
O3 N2 1.220(9) . ?
O2 N2 1.236(10) . ?
N1 C1 1.282(10) . ?
N1 C21 1.423(11) . ?
N1 H1 1.32(10) . ?
N2 C15 1.448(11) . ?
C15 C16 1.351(12) . ?
C15 C14 1.399(12) . ?
C17 C16 1.393(12) . ?
C17 C12 1.443(12) . ?
C17 C1 1.455(13) . ?
C21 C26 1.354(11) . ?
C21 C22 1.402(12) . ?
C22 C23 1.369(13) . ?
C16 H16 0.9300 . ?
C12 C13 1.412(13) . ?
C1 H1A 0.9300 . ?
C26 C25 1.376(13) . ?
C26 H26 0.9300 . ?
C14 C13 1.343(12) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C23 C24 1.346(13) . ?
C23 H23 0.9300 . ?
C24 C25 1.360(13) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 O4 H4 112(7) . . ?
C1 N1 C21 125.6(8) . . ?
C1 N1 H1 116(4) . . ?
C21 N1 H1 119(4) . . ?
O3 N2 O2 122.7(9) . . ?
O3 N2 C15 119.9(8) . . ?
O2 N2 C15 117.4(9) . . ?
C16 C15 C14 121.4(8) . . ?
C16 C15 N2 117.7(9) . . ?
C14 C15 N2 120.9(9) . . ?
C16 C17 C12 120.8(9) . . ?
C16 C17 C1 119.2(8) . . ?
C12 C17 C1 119.9(9) . . ?
C26 C21 C22 119.6(9) . . ?
C26 C21 N1 124.7(8) . . ?
C22 C21 N1 115.7(8) . . ?
O4 C22 C23 127.0(9) . . ?
O4 C22 C21 114.2(8) . . ?
C23 C22 C21 118.8(9) . . ?
C15 C16 C17 119.1(8) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
O1 C12 C13 122.4(9) . . ?
O1 C12 C17 120.8(9) . . ?
C13 C12 C17 116.8(9) . . ?
N1 C1 C17 122.8(8) . . ?
N1 C1 H1A 118.6 . . ?
C17 C1 H1A 118.6 . . ?
C21 C26 C25 120.1(10) . . ?
C21 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C13 C14 C15 121.0(9) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C13 C12 120.9(9) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C24 C23 C22 121.1(10) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 120.1(10) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C26 120.3(9) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C16 H16 O3 0.93 2.59 3.385(12) 144.3 3_566
C1 H1A O3 0.93 2.34 3.198(12) 154.1 3_566
N1 H1 O1 1.32(10) 1.56(10) 2.588(9) 127(7) .
O4 H4 O1 0.93(11) 1.71(11) 2.578(8) 154(10) 3_765

_refine_diff_density_max         0.333
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_SOLVE_1E_a
_database_code_depnum_ccdc_archive 'CCDC 2191116'
loop_
_audit_author_name
_audit_author_address
'Siya T. Hulushe'
;Rhodes University
South Africa
;
_audit_update_record             
;
2022-07-18 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        
2-((E)-(2-methoxyphenyliminio)methyl)-4-nitrophenolate
_chemical_name_common            5-nitrosalicylaldehyde-o-anisidine
_chemical_formula_moiety         'C14 H14 N2 O6'
_chemical_formula_sum            'C14 H14 N2 O6'
_exptl_crystal_recrystallization_method 
'slow evaporation from water/methanol mixture'
_chemical_melting_point          ?
_exptl_crystal_description       prism
_exptl_crystal_colour            red-orange
_diffrn_ambient_temperature      298(2)
_chemical_formula_weight         306.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yn'
_chemical_absolute_configuration unk

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'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_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.
;

_cell_length_a                   26.121(3)
_cell_length_b                   7.0281(7)
_cell_length_c                   15.8739(17)
_cell_angle_alpha                90
_cell_angle_beta                 111.639(4)
_cell_angle_gamma                90
_cell_volume                     2708.8(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2135
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      20.75
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.167
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6255
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-IV CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.03
_diffrn_reflns_number            14279
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_av_R_equivalents  0.1243
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.650
_diffrn_reflns_theta_max         21.263
_diffrn_reflns_theta_full        21.263
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1506
_reflns_number_gt                875
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Carbon-bound H atoms were placed in calculated positions and were included in
the refinement in the riding model approximation, with Uiso(H) set to
1.2 Ueq(C).

The nitrogen-bound hydrogen atom was located on a difference
Fourier map and refined freely.

The H atoms of the methyl group were allowed to rotate with a fixed angle around
the C---O bond to best fit the experimental electron density (HFIX 137 in the
SHELX program suite (Sheldrick, 2015)), with Uiso(H) set to 1.5
Ueq(C).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0985P)²+0.0204P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1506
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1247
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.2331
_refine_ls_wR_factor_gt          0.1502
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.135
_refine_ls_shift/su_mean         0.009

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 0.48711(18) 0.2600(6) 0.3866(3) 0.121(3) Uani 1 1 d . . . . .
O4 O 0.61842(18) 0.3556(7) 0.4553(3) 0.124(3) Uani 1 1 d . . . . .
N1 N 0.5577(2) 0.2948(7) 0.5485(3) 0.104(3) Uani 1 1 d . . . . .
H1 H 0.548302 0.293380 0.490593 0.125 Uiso 1 1 calc R U . . .
O2 O 0.3420(2) 0.0891(8) 0.6135(4) 0.145(3) Uani 1 1 d . . . . .
O3 O 0.2842(2) 0.0404(9) 0.4776(4) 0.157(3) Uani 1 1 d . . . . .
N2 N 0.3303(3) 0.0842(8) 0.5316(5) 0.127(3) Uani 1 1 d . . . . .
C11 C 0.4640(2) 0.2174(8) 0.5169(4) 0.100(3) Uani 1 1 d . . . . .
C12 C 0.4506(3) 0.2186(8) 0.4203(4) 0.104(3) Uani 1 1 d . . . . .
C21 C 0.6133(2) 0.3381(8) 0.5979(4) 0.101(3) Uani 1 1 d . . . . .
C15 C 0.3724(3) 0.1300(8) 0.4952(5) 0.106(3) Uani 1 1 d . . . . .
C1 C 0.5182(3) 0.2565(8) 0.5776(4) 0.107(3) Uani 1 1 d . . . . .
H1A H 0.525897 0.254780 0.639628 0.129 Uiso 1 1 calc R U . . .
C16 C 0.4241(3) 0.1722(9) 0.5521(4) 0.109(3) Uani 1 1 d . . . . .
H16 H 0.432933 0.170878 0.614453 0.130 Uiso 1 1 calc R U . . .
C22 C 0.6458(3) 0.3714(8) 0.5477(4) 0.106(3) Uani 1 1 d . . . . .
C13 C 0.3959(3) 0.1673(10) 0.3660(4) 0.115(3) Uani 1 1 d . . . . .
H13 H 0.385979 0.162615 0.303403 0.138 Uiso 1 1 calc R U . . .
C26 C 0.6365(3) 0.3425(10) 0.6906(4) 0.116(3) Uani 1 1 d . . . . .
H26 H 0.615125 0.316885 0.724844 0.140 Uiso 1 1 calc R U . . .
C14 C 0.3579(3) 0.1249(9) 0.4015(5) 0.116(3) Uani 1 1 d . . . . .
H14 H 0.322210 0.092597 0.363849 0.139 Uiso 1 1 calc R U . . .
C23 C 0.7012(3) 0.4163(9) 0.5900(5) 0.117(3) Uani 1 1 d . . . . .
H23 H 0.722853 0.441591 0.556095 0.140 Uiso 1 1 calc R U . . .
C24 C 0.7233(3) 0.4225(11) 0.6825(5) 0.129(3) Uani 1 1 d . . . . .
H24 H 0.760343 0.452755 0.711734 0.155 Uiso 1 1 calc R U . . .
C25 C 0.6917(3) 0.3848(10) 0.7330(5) 0.127(3) Uani 1 1 d . . . . .
H25 H 0.707433 0.387796 0.795958 0.153 Uiso 1 1 calc R U . . .
C27 C 0.6482(3) 0.3953(11) 0.3974(5) 0.131(3) Uani 1 1 d . . . . .
H27A H 0.662171 0.523011 0.407819 0.197 Uiso 1 1 calc R U . . .
H27B H 0.624056 0.381769 0.335255 0.197 Uiso 1 1 calc R U . . .
H27C H 0.678341 0.307676 0.410419 0.197 Uiso 1 1 calc R U . . .
O5 O 0.500000 0.0169(10) 0.250000 0.198(4) Uani 1 2 d GS T P . .
H5WA H 0.525741 -0.050079 0.286523 0.297 Uiso 0.5 1 d G U P . .
H5WB H 0.503647 0.131739 0.268092 0.297 Uiso 0.5 1 d G U P . .
O6 O 0.491(4) 0.5116(11) 0.249(7) 0.165(18) Uani 0.5 1 d G . P . .
H6WA H 0.493671 0.466684 0.300598 0.247 Uiso 0.5 1 d G U P . .
H6WB H 0.492415 0.421267 0.214765 0.247 Uiso 0.5 1 d G U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.286(7) . ?
O4 C22 1.379(7) . ?
O4 C27 1.433(7) . ?
N1 C1 1.302(7) . ?
N1 C21 1.407(7) . ?
N1 H1 0.8600 . ?
O2 N2 1.221(7) . ?
O3 N2 1.231(7) . ?
N2 C15 1.454(8) . ?
C11 C16 1.389(8) . ?
C11 C1 1.416(8) . ?
C11 C12 1.442(8) . ?
C12 C13 1.416(8) . ?
C21 C26 1.369(8) . ?
C21 C22 1.383(8) . ?
C15 C16 1.353(8) . ?
C15 C14 1.394(9) . ?
C1 H1A 0.9300 . ?
C16 H16 0.9300 . ?
C22 C23 1.388(8) . ?
C13 C14 1.345(8) . ?
C13 H13 0.9300 . ?
C26 C25 1.379(9) . ?
C26 H26 0.9300 . ?
C14 H14 0.9300 . ?
C23 C24 1.366(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.373(9) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
O5 H5WA 0.8500 . ?
O5 H5WB 0.8499 . ?
O5 H5WA 0.85(3) 2_655 ?
O5 H5WB 0.850(19) 2_655 ?
O6 H6WA 0.8501 . ?
O6 H6WB 0.8499 . ?
O6 H6WB 0.86(11) 2_655 ?

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
C22 O4 C27 118.3(5) . . ?
C1 N1 C21 129.5(5) . . ?
C1 N1 H1 115.2 . . ?
C21 N1 H1 115.2 . . ?
O2 N2 O3 123.0(6) . . ?
O2 N2 C15 119.2(6) . . ?
O3 N2 C15 117.8(7) . . ?
C16 C11 C1 118.8(5) . . ?
C16 C11 C12 120.4(5) . . ?
C1 C11 C12 120.8(5) . . ?
O1 C12 C13 122.7(6) . . ?
O1 C12 C11 121.1(6) . . ?
C13 C12 C11 116.1(6) . . ?
C26 C21 C22 119.5(6) . . ?
C26 C21 N1 124.1(5) . . ?
C22 C21 N1 116.3(5) . . ?
C16 C15 C14 122.0(5) . . ?
C16 C15 N2 120.0(6) . . ?
C14 C15 N2 118.1(6) . . ?
N1 C1 C11 121.5(6) . . ?
N1 C1 H1A 119.3 . . ?
C11 C1 H1A 119.2 . . ?
C15 C16 C11 119.6(6) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
O4 C22 C21 114.3(5) . . ?
O4 C22 C23 124.9(6) . . ?
C21 C22 C23 120.8(6) . . ?
C14 C13 C12 122.5(6) . . ?
C14 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
C21 C26 C25 119.9(6) . . ?
C21 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C13 C14 C15 119.3(6) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C24 C23 C22 118.6(6) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
C23 C24 C25 121.0(6) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C24 C25 C26 120.1(7) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
O4 C27 H27A 109.5 . . ?
O4 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O4 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
H5WA O5 H5WB 109.5 . . ?
H5WA O5 H5WA 112.7 . 2_655 ?
H5WB O5 H5WA 135.9 . 2_655 ?
H5WA O5 H5WB 135.9 . 2_655 ?
H5WB O5 H5WB 36.6 . 2_655 ?
H5WA O5 H5WB 109.5 2_655 2_655 ?
H6WA O6 H6WB 109.5 . . ?
H6WA O6 H6WB 41.1 . 2_655 ?
H6WB O6 H6WB 75.1 . 2_655 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 1.84 2.563(6) 140.4 .
C1 H1A O6 0.93 2.56 3.28(15) 134.1 5_666
C16 H16 O5 0.93 2.58 3.312(7) 135.9 5_656
C23 H23 O3 0.93 2.47 3.391(8) 173.4 3
N1 H1 O4 0.86 2.15 2.574(6) 110.1 .

_refine_diff_density_max         0.011
_refine_diff_density_min         -0.010
_refine_diff_density_rms         0.002

####################################################################### 
# 
# 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_SOLVE_1G
_database_code_depnum_ccdc_archive 'CCDC 2191118'
loop_
_audit_author_name
_audit_author_address
'Siya T. Hulushe'
;Rhodes University
South Africa
;
_audit_update_record             
;
2022-07-18 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        
2-((E)-(3-chlorophenylimino)methyl-4-nitrophenol
_chemical_name_common            5-nitro-N-[3-(chloro)phenyl]salicylaldimine
_chemical_formula_moiety         'C13 H8 Cl N2 O3'
_chemical_formula_sum            'C13 H8 Cl N2 O3'
_exptl_crystal_recrystallization_method 'slow evaporation from MeCN'
_chemical_melting_point          ?
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         275.66

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration unk

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'

_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.
;

_cell_length_a                   14.6564(3)
_cell_length_b                   3.73740(10)
_cell_length_c                   21.4431(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.109(2)
_cell_angle_gamma                90
_cell_volume                     1173.79(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1861
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      18.43
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_F_000             564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.073
_exptl_absorpt_coefficient_mu    2.955
_shelx_estimated_absorpt_T_min   0.518
_shelx_estimated_absorpt_T_max   0.813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-IV CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            11919
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.592
_diffrn_reflns_theta_max         78.361
_diffrn_reflns_theta_full        25.125
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             2449
_reflns_number_gt                2230
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Carbon-bound H atoms were placed in calculated positions and were included in
the refinement in the riding model approximation, with Uiso(H) set to
1.2 Ueq(C).

The oxygen-bound hydrogen atoms were located on a difference Fourier map and 
refined freely.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0764P)²+0.4868P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2449
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1264
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.52665(3) 0.35805(13) 0.07092(2) 0.03492(18) Uani 1 1 d . . . . .
O1 O 0.24228(9) 0.2749(4) 0.32052(6) 0.0317(3) Uani 1 1 d . . . . .
O3 O 0.41512(9) 0.9668(4) 0.56189(6) 0.0372(3) Uani 1 1 d . . . . .
O2 O 0.27574(10) 0.9070(5) 0.58942(6) 0.0425(4) Uani 1 1 d . . . . .
N1 N 0.41332(10) 0.3189(4) 0.29312(6) 0.0247(3) Uani 1 1 d . . . . .
N2 N 0.33568(10) 0.8698(4) 0.55151(7) 0.0273(3) Uani 1 1 d . . . . .
C16 C 0.38025(11) 0.6570(4) 0.44932(8) 0.0238(4) Uani 1 1 d . . . . .
H16 H 0.441365 0.724025 0.460020 0.029 Uiso 1 1 calc R U . . .
C22 C 0.47159(11) 0.3211(4) 0.18958(8) 0.0249(4) Uani 1 1 d . . . . .
H22 H 0.414521 0.410093 0.173915 0.030 Uiso 1 1 calc R U . . .
C11 C 0.35881(11) 0.5098(5) 0.39119(7) 0.0237(3) Uani 1 1 d . . . . .
C15 C 0.31231(11) 0.7057(5) 0.49164(8) 0.0240(3) Uani 1 1 d . . . . .
C1 C 0.43067(11) 0.4517(5) 0.34733(8) 0.0248(4) Uani 1 1 d . . . . .
H1A H 0.491770 0.513550 0.359120 0.030 Uiso 1 1 calc R U . . .
C21 C 0.48640(11) 0.2514(5) 0.25306(8) 0.0238(3) Uani 1 1 d . . . . .
C12 C 0.26656(11) 0.4142(5) 0.37608(8) 0.0250(4) Uani 1 1 d . . . . .
C26 C 0.56929(12) 0.1095(4) 0.27550(8) 0.0259(4) Uani 1 1 d . . . . .
H26 H 0.578798 0.060249 0.318709 0.031 Uiso 1 1 calc R U . . .
C14 C 0.22154(12) 0.6104(5) 0.47752(8) 0.0267(4) Uani 1 1 d . . . . .
H14 H 0.175756 0.646086 0.507130 0.032 Uiso 1 1 calc R U . . .
C13 C 0.19980(11) 0.4643(5) 0.42004(8) 0.0281(4) Uani 1 1 d . . . . .
H13 H 0.138512 0.396515 0.410102 0.034 Uiso 1 1 calc R U . . .
C23 C 0.54242(12) 0.2569(5) 0.14999(8) 0.0260(4) Uani 1 1 d . . . . .
C24 C 0.62538(12) 0.1148(5) 0.17106(9) 0.0288(4) Uani 1 1 d . . . . .
H24 H 0.672589 0.069211 0.142924 0.035 Uiso 1 1 calc R U . . .
C25 C 0.63772(12) 0.0410(5) 0.23408(8) 0.0282(4) Uani 1 1 d . . . . .
H25 H 0.693969 -0.058106 0.249215 0.034 Uiso 1 1 calc R U . . .
H1 H 0.290(2) 0.257(8) 0.3007(13) 0.052(7) 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
Cl1 C23 1.7443(17) . ?
O1 C12 1.337(2) . ?
O3 N2 1.232(2) . ?
O2 N2 1.227(2) . ?
N1 C1 1.281(2) . ?
N1 C21 1.420(2) . ?
N2 C15 1.452(2) . ?
C16 C15 1.384(2) . ?
C16 C11 1.388(2) . ?
C22 C23 1.386(2) . ?
C22 C21 1.395(2) . ?
C11 C12 1.424(2) . ?
C11 C1 1.454(2) . ?
C15 C14 1.400(2) . ?
C21 C26 1.395(2) . ?
C12 C13 1.396(2) . ?
C26 C25 1.388(2) . ?
C14 C13 1.375(2) . ?
C23 C24 1.387(2) . ?
C24 C25 1.384(3) . ?

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 C21 119.26(14) . . ?
O2 N2 O3 122.82(15) . . ?
O2 N2 C15 118.84(15) . . ?
O3 N2 C15 118.33(14) . . ?
C15 C16 C11 119.76(15) . . ?
C23 C22 C21 118.18(15) . . ?
C16 C11 C12 119.05(15) . . ?
C16 C11 C1 119.65(14) . . ?
C12 C11 C1 121.30(15) . . ?
C16 C15 C14 121.74(15) . . ?
C16 C15 N2 118.90(15) . . ?
C14 C15 N2 119.34(15) . . ?
N1 C1 C11 121.37(15) . . ?
C26 C21 C22 120.65(15) . . ?
C26 C21 N1 121.71(15) . . ?
C22 C21 N1 117.60(14) . . ?
O1 C12 C13 118.95(15) . . ?
O1 C12 C11 121.34(15) . . ?
C13 C12 C11 119.72(15) . . ?
C25 C26 C21 119.36(16) . . ?
C13 C14 C15 118.82(16) . . ?
C14 C13 C12 120.91(16) . . ?
C22 C23 C24 122.29(16) . . ?
C22 C23 Cl1 118.84(13) . . ?
C24 C23 Cl1 118.87(13) . . ?
C25 C24 C23 118.40(16) . . ?
C24 C25 C26 121.08(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C16 H16 O3 0.95 2.46 3.329(2) 152.0 3_676
C26 H26 O3 0.95 2.56 3.498(2) 168.9 3_666
C24 H24 O2 0.95 2.63 3.465(2) 147.5 4_665
O1 H1 N1 0.84(3) 1.83(3) 2.6009(19) 152(3) .

_refine_diff_density_max         0.415
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_SOLVE_1D_a
_database_code_depnum_ccdc_archive 'CCDC 2191115'
loop_
_audit_author_name
_audit_author_address
'Siya T. Hulushe'
;Rhodes University
South Africa
;
_audit_update_record             
;
2022-07-18 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        
2-((E)-(2-methoxyphenyliminio)methyl)-4-nitrophenolate
_chemical_name_common            5-nitrosalicylaldehyde-o-anisidine
_chemical_formula_moiety         'C14 H14 N2 O6'
_chemical_formula_sum            'C14 H14 N2 O6'
_exptl_crystal_recrystallization_method 
'slow evaporation from water/methanol mixture'
_chemical_melting_point          ?
_exptl_crystal_description       prism
_exptl_crystal_colour            red-orange
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         306.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yn'
_chemical_absolute_configuration unk

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'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_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.
;

_cell_length_a                   26.0543(14)
_cell_length_b                   6.9252(4)
_cell_length_c                   15.7729(9)
_cell_angle_alpha                90
_cell_angle_beta                 111.788(2)
_cell_angle_gamma                90
_cell_volume                     2642.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3540
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      23.23
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.167
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6338
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-IV CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.98
_diffrn_reflns_number            34814
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.1147
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.664
_diffrn_reflns_theta_max         23.572
_diffrn_reflns_theta_full        23.572
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1970
_reflns_number_gt                1278
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Carbon-bound H atoms were placed in calculated positions and were included in
the refinement in the riding model approximation, with Uiso(H) set to
1.2 Ueq(C).

The nitrogen-bound hydrogen atom was located on a difference
Fourier map and refined freely.

The H atoms of the methyl group were allowed to rotate with a fixed angle around
the C---O bond to best fit the experimental electron density (HFIX 137 in the
SHELX program suite (Sheldrick, 2015)), with Uiso(H) set to 1.5
Ueq(C).

The structure contains partially occupied water molecules. The hydrogen atoms
of the water molecules could not be located on the difference Fourier map.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0878P)²+0.0701P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1970
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1179
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.2317
_refine_ls_wR_factor_gt          0.1506
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.153
_refine_ls_shift/su_mean         0.013

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 0.51300(14) 0.2591(5) 0.6136(2) 0.0872(17) Uani 1 1 d . . . . .
O4 O 0.38197(14) 0.3535(5) 0.5448(2) 0.0885(18) Uani 1 1 d . . . . .
O2 O 0.65978(15) 0.0872(6) 0.3866(2) 0.0966(18) Uani 1 1 d . . . . .
N1 N 0.44276(15) 0.2965(5) 0.4504(3) 0.0789(18) Uani 1 1 d . . . . .
H1 H 0.452489 0.294337 0.510073 0.095 Uiso 1 1 calc R U . . .
O3 O 0.71715(15) 0.0318(6) 0.5239(3) 0.1047(19) Uani 1 1 d . . . . .
N2 N 0.67073(17) 0.0793(6) 0.4692(3) 0.0878(18) Uani 1 1 d . . . . .
O5 O 0.500000 0.5120(9) 0.750000 0.124(3) Uani 1 2 d S T P . .
O6 O 0.500000 0.0123(9) 0.750000 0.119(2) Uani 1 2 d S T P . .
C11 C 0.53646(18) 0.2173(6) 0.4822(3) 0.0767(18) Uani 1 1 d . . . . .
C15 C 0.62918(19) 0.1255(7) 0.5058(3) 0.0806(18) Uani 1 1 d . . . . .
C1 C 0.48213(19) 0.2576(6) 0.4205(3) 0.0777(18) Uani 1 1 d . . . . .
H1A H 0.474243 0.256436 0.356632 0.093 Uiso 1 1 calc R U . . .
C12 C 0.5497(2) 0.2165(7) 0.5801(3) 0.0799(18) Uani 1 1 d . . . . .
C22 C 0.35450(19) 0.3744(7) 0.4527(3) 0.0795(18) Uani 1 1 d . . . . .
C21 C 0.38684(18) 0.3414(7) 0.4003(3) 0.0779(18) Uani 1 1 d . . . . .
C16 C 0.57711(19) 0.1727(7) 0.4474(3) 0.0799(18) Uani 1 1 d . . . . .
H16 H 0.568613 0.175130 0.383422 0.096 Uiso 1 1 calc R U . . .
C13 C 0.6044(2) 0.1630(7) 0.6358(3) 0.0836(19) Uani 1 1 d . . . . .
H13 H 0.614243 0.157006 0.700114 0.100 Uiso 1 1 calc R U . . .
C14 C 0.6431(2) 0.1201(7) 0.6005(3) 0.0846(19) Uani 1 1 d . . . . .
H14 H 0.679596 0.086554 0.639731 0.101 Uiso 1 1 calc R U . . .
C23 C 0.29893(19) 0.4237(7) 0.4106(3) 0.0854(19) Uani 1 1 d . . . . .
H23 H 0.277011 0.449991 0.445776 0.102 Uiso 1 1 calc R U . . .
C26 C 0.3631(2) 0.3478(7) 0.3064(3) 0.0839(19) Uani 1 1 d . . . . .
H26 H 0.384670 0.320988 0.270745 0.101 Uiso 1 1 calc R U . . .
C24 C 0.2765(2) 0.4335(8) 0.3166(3) 0.090(2) Uani 1 1 d . . . . .
H24 H 0.238770 0.468509 0.286990 0.108 Uiso 1 1 calc R U . . .
C25 C 0.3078(2) 0.3934(8) 0.2645(3) 0.090(2) Uani 1 1 d . . . . .
H25 H 0.291157 0.397233 0.199724 0.108 Uiso 1 1 calc R U . . .
C27 C 0.3520(2) 0.3970(8) 0.6030(3) 0.090(2) Uani 1 1 d . . . . .
H27A H 0.338964 0.530899 0.593039 0.136 Uiso 1 1 calc R U . . .
H27B H 0.376381 0.379815 0.666972 0.136 Uiso 1 1 calc R U . . .
H27C H 0.320253 0.309816 0.588535 0.136 Uiso 1 1 calc R U . . .
H5WA H 0.502(3) 0.444(12) 0.701(5) 0.15(3) Uiso 1 1 d . . . . .
H6WA H 0.506(5) 0.127(17) 0.700(7) 0.24(5) 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
O1 C12 1.286(6) . ?
O4 C22 1.368(5) . ?
O4 C27 1.440(6) . ?
O2 N2 1.226(5) . ?
N1 C1 1.306(6) . ?
N1 C21 1.410(6) . ?
N1 H1 0.8800 . ?
O3 N2 1.242(5) . ?
N2 C15 1.440(6) . ?
O5 H5WA 0.92(7) . ?
O6 H6WA 1.16(11) . ?
C11 C16 1.396(6) . ?
C11 C1 1.417(6) . ?
C11 C12 1.452(6) . ?
C15 C16 1.367(7) . ?
C15 C14 1.400(7) . ?
C1 H1A 0.9500 . ?
C12 C13 1.420(7) . ?
C22 C23 1.393(7) . ?
C22 C21 1.401(6) . ?
C21 C26 1.377(6) . ?
C16 H16 0.9500 . ?
C13 C14 1.354(7) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C23 C24 1.379(7) . ?
C23 H23 0.9500 . ?
C26 C25 1.381(7) . ?
C26 H26 0.9500 . ?
C24 C25 1.383(7) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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
C22 O4 C27 117.4(4) . . ?
C1 N1 C21 129.1(4) . . ?
C1 N1 H1 115.5 . . ?
C21 N1 H1 115.5 . . ?
O2 N2 O3 122.2(4) . . ?
O2 N2 C15 120.2(4) . . ?
O3 N2 C15 117.6(4) . . ?
C16 C11 C1 118.9(4) . . ?
C16 C11 C12 120.1(4) . . ?
C1 C11 C12 120.9(4) . . ?
C16 C15 C14 121.7(4) . . ?
C16 C15 N2 119.2(4) . . ?
C14 C15 N2 119.1(4) . . ?
N1 C1 C11 120.7(4) . . ?
N1 C1 H1A 119.6 . . ?
C11 C1 H1A 119.6 . . ?
O1 C12 C13 122.3(4) . . ?
O1 C12 C11 121.2(4) . . ?
C13 C12 C11 116.5(4) . . ?
O4 C22 C23 125.0(4) . . ?
O4 C22 C21 114.6(4) . . ?
C23 C22 C21 120.3(4) . . ?
C26 C21 C22 120.0(4) . . ?
C26 C21 N1 124.6(4) . . ?
C22 C21 N1 115.4(4) . . ?
C15 C16 C11 119.7(4) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
C14 C13 C12 122.2(4) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C13 C14 C15 119.6(4) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C24 C23 C22 118.4(5) . . ?
C24 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?
C21 C26 C25 119.7(4) . . ?
C21 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C23 C24 C25 121.4(5) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C26 C25 C24 120.1(5) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
O4 C27 H27A 109.5 . . ?
O4 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O4 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.88 1.82 2.559(5) 140.7 .
N1 H1 O4 0.88 2.14 2.576(5) 109.7 .
C1 H1A O5 0.95 2.59 3.305(6) 132.7 5_666
C16 H16 O6 0.95 2.55 3.276(5) 133.1 5_656
C23 H23 O3 0.95 2.39 3.335(6) 175.3 3_455
O5 H5WA O1 0.92(7) 1.98(8) 2.890(5) 169(7) .
O6 H6WA O1 1.16(11) 1.71(11) 2.865(5) 169(9) .

_refine_diff_density_max         0.019
_refine_diff_density_min         -0.013
_refine_diff_density_rms         0.004

####################################################################### 
# 
# 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_SOLVE_1F_a
_database_code_depnum_ccdc_archive 'CCDC 2191117'
loop_
_audit_author_name
_audit_author_address
'Siya T. Hulushe'
;Rhodes University
South Africa
;
_audit_update_record             
;
2022-07-18 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        2-((E)-(p-tolylimino)methyl)-4-nitrophenol
_chemical_name_common            5-nitrosalicylaldehyde-p-toluidine
_chemical_formula_moiety         'C14 H12 N2 O3'
_chemical_formula_sum            'C14 H12 N2 O3'
_exptl_crystal_recrystallization_method 
'slow evaporation from methano/hexane mixture'
_chemical_melting_point          ?
_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         256.26

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration unk

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'

_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.
;

_cell_length_a                   14.0746(8)
_cell_length_b                   13.9715(7)
_cell_length_c                   6.1944(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.289(2)
_cell_angle_gamma                90
_cell_volume                     1212.90(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4844
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      21.68
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.219
_exptl_crystal_size_min          0.084
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6145
_exptl_absorpt_correction_T_max  0.7447
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-IV CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9.89
_diffrn_reflns_number            5853
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.058
_diffrn_reflns_theta_max         21.978
_diffrn_reflns_theta_full        21.978
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1474
_reflns_number_gt                904
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Carbon-bound H atoms were placed in calculated positions and were included in
the refinement in the riding model approximation, with Uiso(H) set to
1.2 Ueq(C).

The nitrogen-bound hydrogen atom was located on a difference
Fourier map and refined freely.

The H atoms of the methyl group were allowed to rotate with a fixed angle around
the C---C bond to best fit the experimental electron density (HFIX 137 in the
SHELX program suite (Sheldrick, 2015)), with Uiso(H) set to 1.5
Ueq(C).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0900P)²+0.0037P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1474
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1151
_refine_ls_R_factor_gt           0.0622
_refine_ls_wR_factor_ref         0.2187
_refine_ls_wR_factor_gt          0.1566
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.140
_refine_ls_shift/su_mean         0.006

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 0.3111(3) 0.3335(3) 0.6894(6) 0.089(2) Uani 1 1 d . . . . .
O2 O 0.6303(3) 0.4437(3) 0.1002(7) 0.095(2) Uani 1 1 d . . . . .
N1 N 0.2127(3) 0.3802(3) 0.3390(6) 0.079(2) Uani 1 1 d . . . . .
O3 O 0.7161(3) 0.4042(3) 0.3932(7) 0.108(2) Uani 1 1 d . . . . .
N2 N 0.6385(3) 0.4141(3) 0.2888(8) 0.086(2) Uani 1 1 d . . . . .
C11 C 0.3824(3) 0.3859(3) 0.3744(7) 0.073(2) Uani 1 1 d . . . . .
C16 C 0.4652(3) 0.4064(3) 0.2786(8) 0.074(2) Uani 1 1 d . . . . .
H16 H 0.461547 0.430074 0.134370 0.089 Uiso 1 1 calc R U . . .
C12 C 0.3887(4) 0.3516(3) 0.5907(8) 0.077(2) Uani 1 1 d . . . . .
C15 C 0.5522(3) 0.3924(3) 0.3922(8) 0.077(2) Uani 1 1 d . . . . .
C21 C 0.1223(3) 0.3792(3) 0.2151(8) 0.077(2) Uani 1 1 d . . . . .
C22 C 0.1113(4) 0.3437(3) 0.0051(8) 0.080(2) Uani 1 1 d . . . . .
H22 H 0.165516 0.323491 -0.063615 0.096 Uiso 1 1 calc R U . . .
C13 C 0.4789(4) 0.3381(3) 0.7005(8) 0.079(2) Uani 1 1 d . . . . .
H13 H 0.483782 0.315028 0.845379 0.094 Uiso 1 1 calc R U . . .
C1 C 0.2909(4) 0.3957(3) 0.2513(8) 0.080(2) Uani 1 1 d . . . . .
H1A H 0.288096 0.413837 0.103059 0.096 Uiso 1 1 calc R U . . .
C26 C 0.0425(4) 0.4073(3) 0.3135(8) 0.082(2) Uani 1 1 d . . . . .
H26 H 0.049173 0.430357 0.458437 0.098 Uiso 1 1 calc R U . . .
C14 C 0.5603(4) 0.3573(3) 0.6037(8) 0.080(2) Uani 1 1 d . . . . .
H14 H 0.621268 0.346943 0.679385 0.096 Uiso 1 1 calc R U . . .
C23 C 0.0213(4) 0.3379(3) -0.1035(8) 0.082(2) Uani 1 1 d . . . . .
H23 H 0.014486 0.314132 -0.247825 0.098 Uiso 1 1 calc R U . . .
C25 C -0.0467(4) 0.4019(4) 0.2021(8) 0.084(2) Uani 1 1 d . . . . .
H25 H -0.100582 0.423518 0.270250 0.101 Uiso 1 1 calc R U . . .
C24 C -0.0598(4) 0.3660(3) -0.0064(9) 0.084(2) Uani 1 1 d . . . . .
C27 C -0.1566(4) 0.3560(4) -0.1264(10) 0.100(3) Uani 1 1 d . . . . .
H27A H -0.171562 0.287944 -0.148455 0.149 Uiso 1 1 calc R U . . .
H27B H -0.157273 0.387899 -0.267422 0.149 Uiso 1 1 calc R U . . .
H27C H -0.204393 0.385473 -0.042024 0.149 Uiso 1 1 calc R U . . .
H1 H 0.246(4) 0.345(4) 0.565(10) 0.114(18) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.325(6) . ?
O1 H1 1.15(6) . ?
O2 N2 1.234(5) . ?
N1 C1 1.289(6) . ?
N1 C21 1.425(6) . ?
O3 N2 1.226(5) . ?
N2 C15 1.455(6) . ?
C11 C16 1.384(6) . ?
C11 C12 1.418(7) . ?
C11 C1 1.442(7) . ?
C16 C15 1.370(6) . ?
C16 H16 0.9500 . ?
C12 C13 1.396(7) . ?
C15 C14 1.394(7) . ?
C21 C26 1.384(7) . ?
C21 C22 1.387(7) . ?
C22 C23 1.381(7) . ?
C22 H22 0.9500 . ?
C13 C14 1.368(7) . ?
C13 H13 0.9500 . ?
C1 H1A 0.9500 . ?
C26 C25 1.378(7) . ?
C26 H26 0.9500 . ?
C14 H14 0.9500 . ?
C23 C24 1.395(7) . ?
C23 H23 0.9500 . ?
C25 C24 1.382(7) . ?
C25 H25 0.9500 . ?
C24 C27 1.497(7) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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 O1 H1 108(3) . . ?
C1 N1 C21 122.0(4) . . ?
O3 N2 O2 122.6(5) . . ?
O3 N2 C15 118.9(5) . . ?
O2 N2 C15 118.5(4) . . ?
C16 C11 C12 119.5(4) . . ?
C16 C11 C1 120.0(4) . . ?
C12 C11 C1 120.4(5) . . ?
C15 C16 C11 119.9(4) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
O1 C12 C13 120.0(4) . . ?
O1 C12 C11 121.2(4) . . ?
C13 C12 C11 118.7(5) . . ?
C16 C15 C14 121.6(5) . . ?
C16 C15 N2 119.2(4) . . ?
C14 C15 N2 119.2(4) . . ?
C26 C21 C22 119.4(5) . . ?
C26 C21 N1 118.7(5) . . ?
C22 C21 N1 121.7(4) . . ?
C23 C22 C21 119.7(5) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.2 . . ?
C14 C13 C12 121.4(5) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
N1 C1 C11 121.1(5) . . ?
N1 C1 H1A 119.4 . . ?
C11 C1 H1A 119.4 . . ?
C25 C26 C21 120.2(5) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?
C13 C14 C15 118.8(5) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C22 C23 C24 121.6(5) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C26 C25 C24 121.7(5) . . ?
C26 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C25 C24 C23 117.5(5) . . ?
C25 C24 C27 122.3(5) . . ?
C23 C24 C27 120.2(5) . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C16 H16 O2 0.95 2.56 3.334(6) 139.0 3_665
O1 H1 N1 1.15(6) 1.51(6) 2.550(5) 145(5) .

_refine_diff_density_max         0.012
_refine_diff_density_min         -0.009
_refine_diff_density_rms         0.002

####################################################################### 
# 
# 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_SOLVE_1G_a
_database_code_depnum_ccdc_archive 'CCDC 2191119'
loop_
_audit_author_name
_audit_author_address
'Siya T. Hulushe'
;Rhodes University
South Africa
;
_audit_update_record             
;
2022-07-18 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        2-((E)-(p-tolylimino)methyl)-4-nitrophenol
_chemical_name_common            5-nitrosalicylaldehyde-p-toluidine
_chemical_formula_moiety         'C14 H12 N2 O3'
_chemical_formula_sum            'C14 H12 N2 O3'
_exptl_crystal_recrystallization_method 
'slow evaporation from methanol/hexane mixture'
_chemical_melting_point          ?
_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_diffrn_ambient_temperature      298(2)
_chemical_formula_weight         256.26

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration unk

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'

_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.
;

_cell_length_a                   14.095(6)
_cell_length_b                   14.225(6)
_cell_length_c                   6.247(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.355(17)
_cell_angle_gamma                90
_cell_volume                     1247.2(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3950
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      21.87
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.078
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6933
_exptl_absorpt_correction_T_max  0.7447
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-IV CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9.99
_diffrn_reflns_number            34150
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_av_R_equivalents  0.0944
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.039
_diffrn_reflns_theta_max         21.997
_diffrn_reflns_theta_full        21.997
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1534
_reflns_number_gt                925
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Carbon-bound H atoms were placed in calculated positions and were included in
the refinement in the riding model approximation, with Uiso(H) set to
1.2 Ueq(C).

The nitrogen-bound hydrogen atom was located on a difference
Fourier map and refined freely.

The H atoms of the methyl group were allowed to rotate with a fixed angle around
the C---C bond to best fit the experimental electron density (HFIX 137 in the
SHELX program suite (Sheldrick, 2015)), with Uiso(H) set to 1.5
Ueq(C).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0794P)²+0.0181P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1534
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.2363
_refine_ls_wR_factor_gt          0.1542
_refine_ls_goodness_of_fit_ref   0.860
_refine_ls_restrained_S_all      0.860
_refine_ls_shift/su_max          0.165
_refine_ls_shift/su_mean         0.010

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 0.3126(3) 0.6666(3) 0.6848(7) 0.125(2) Uani 1 1 d . . . . .
N1 N 0.2138(3) 0.6200(3) 0.3364(7) 0.107(2) Uani 1 1 d . . . . .
O2 O 0.6312(3) 0.5562(4) 0.1040(8) 0.143(3) Uani 1 1 d . . . . .
N2 N 0.6388(3) 0.5863(4) 0.2895(9) 0.120(2) Uani 1 1 d . . . . .
C11 C 0.3830(3) 0.6148(4) 0.3721(8) 0.097(2) Uani 1 1 d . . . . .
C16 C 0.4661(4) 0.5949(4) 0.2787(8) 0.099(2) Uani 1 1 d . . . . .
H16 H 0.462568 0.572636 0.138255 0.119 Uiso 1 1 calc R U . . .
O3 O 0.7158(3) 0.5959(5) 0.3906(8) 0.163(3) Uani 1 1 d . . . . .
C12 C 0.3903(4) 0.6482(4) 0.5870(9) 0.105(2) Uani 1 1 d . . . . .
C15 C 0.5526(4) 0.6075(4) 0.3901(9) 0.103(2) Uani 1 1 d . . . . .
C21 C 0.1238(4) 0.6206(4) 0.2133(9) 0.101(2) Uani 1 1 d . . . . .
C1 C 0.2916(4) 0.6056(4) 0.2498(9) 0.106(2) Uani 1 1 d . . . . .
H1A H 0.289007 0.588797 0.105459 0.128 Uiso 1 1 calc R U . . .
C22 C 0.1120(4) 0.6555(4) 0.0059(9) 0.111(2) Uani 1 1 d . . . . .
H22 H 0.164901 0.674990 -0.060746 0.133 Uiso 1 1 calc R U . . .
C13 C 0.4805(4) 0.6613(4) 0.6968(9) 0.108(2) Uani 1 1 d . . . . .
H13 H 0.485307 0.683211 0.837722 0.129 Uiso 1 1 calc R U . . .
C26 C 0.0435(4) 0.5938(4) 0.3103(10) 0.112(2) Uani 1 1 d . . . . .
H26 H 0.049886 0.572103 0.451352 0.135 Uiso 1 1 calc R U . . .
C14 C 0.5613(4) 0.6426(4) 0.6013(9) 0.112(2) Uani 1 1 d . . . . .
H14 H 0.621042 0.652895 0.674199 0.135 Uiso 1 1 calc R U . . .
C25 C -0.0450(4) 0.5988(4) 0.2005(10) 0.117(3) Uani 1 1 d . . . . .
H25 H -0.097690 0.578238 0.266759 0.141 Uiso 1 1 calc R U . . .
C23 C 0.0224(4) 0.6617(4) -0.1032(10) 0.114(3) Uani 1 1 d . . . . .
H23 H 0.015816 0.684790 -0.243030 0.137 Uiso 1 1 calc R U . . .
C24 C -0.0580(4) 0.6338(4) -0.0072(10) 0.116(3) Uani 1 1 d . . . . .
C27 C -0.1555(4) 0.6429(6) -0.1264(13) 0.145(3) Uani 1 1 d . . . . .
H27A H -0.202550 0.620192 -0.037528 0.218 Uiso 1 1 calc R U . . .
H27B H -0.158121 0.606594 -0.256309 0.218 Uiso 1 1 calc R U . . .
H27C H -0.167895 0.707749 -0.161230 0.218 Uiso 1 1 calc R U . . .
H1 H 0.241(4) 0.655(4) 0.565(9) 0.124(17) 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
O1 C12 1.328(6) . ?
O1 H1 1.21(6) . ?
N1 C1 1.285(6) . ?
N1 C21 1.421(7) . ?
O2 N2 1.231(6) . ?
N2 O3 1.211(6) . ?
N2 C15 1.450(7) . ?
C11 C16 1.386(7) . ?
C11 C12 1.419(7) . ?
C11 C1 1.440(7) . ?
C16 C15 1.359(7) . ?
C16 H16 0.9300 . ?
C12 C13 1.400(7) . ?
C15 C14 1.406(8) . ?
C21 C22 1.383(7) . ?
C21 C26 1.386(7) . ?
C1 H1A 0.9300 . ?
C22 C23 1.380(8) . ?
C22 H22 0.9300 . ?
C13 C14 1.361(8) . ?
C13 H13 0.9300 . ?
C26 C25 1.369(8) . ?
C26 H26 0.9300 . ?
C14 H14 0.9300 . ?
C25 C24 1.386(8) . ?
C25 H25 0.9300 . ?
C23 C24 1.388(8) . ?
C23 H23 0.9300 . ?
C24 C27 1.507(8) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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 O1 H1 112(3) . . ?
C1 N1 C21 121.9(5) . . ?
O3 N2 O2 121.7(5) . . ?
O3 N2 C15 119.8(5) . . ?
O2 N2 C15 118.5(5) . . ?
C16 C11 C12 118.5(5) . . ?
C16 C11 C1 120.4(5) . . ?
C12 C11 C1 121.0(5) . . ?
C15 C16 C11 120.8(5) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
O1 C12 C13 119.9(5) . . ?
O1 C12 C11 120.7(5) . . ?
C13 C12 C11 119.4(5) . . ?
C16 C15 C14 121.6(5) . . ?
C16 C15 N2 119.9(5) . . ?
C14 C15 N2 118.5(5) . . ?
C22 C21 C26 118.5(5) . . ?
C22 C21 N1 122.2(5) . . ?
C26 C21 N1 119.0(5) . . ?
N1 C1 C11 121.2(5) . . ?
N1 C1 H1A 119.4 . . ?
C11 C1 H1A 119.4 . . ?
C23 C22 C21 120.7(5) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C14 C13 C12 121.2(5) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C25 C26 C21 120.6(5) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
C13 C14 C15 118.5(5) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
C26 C25 C24 121.5(5) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C22 C23 C24 120.9(6) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C25 C24 C23 117.8(5) . . ?
C25 C24 C27 121.8(6) . . ?
C23 C24 C27 120.4(6) . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C16 H16 O2 0.93 2.65 3.406(7) 139.0 3_665
O1 H1 N1 1.21(6) 1.53(6) 2.560(6) 138(4) .

_refine_diff_density_max         0.017
_refine_diff_density_min         -0.012
_refine_diff_density_rms         0.003

####################################################################### 
# 
# 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_sh37_300b_auto
_database_code_depnum_ccdc_archive 'CCDC 2156467'
loop_
_audit_author_name
_audit_author_address
'Frederick P. Malan'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2022-07-19 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2022-02-25
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_chemical_name_common            5-nitro-N-[3-(chloro)phenyl]salicylaldimine
_chemical_name_systematic        
2-((E)-(3-chlorophenylimino)methyl-4-nitrophenol
_chemical_formula_moiety         'C13 H9 Cl N2 O3'
_chemical_formula_sum            'C13 H9 Cl N2 O3'
_exptl_crystal_recrystallization_method 'slow evaporation from MeCN'
_chemical_formula_weight         276.66
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.7430(5)
_cell_length_b                   3.7894(10)
_cell_length_c                   21.5528(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.845(3)
_cell_angle_gamma                90
_cell_volume                     1203.47(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4183
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      77.6180
_cell_measurement_theta_min      3.5700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.882
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_description       Needles
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.073
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            6431
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.264
_diffrn_reflns_theta_min         3.579
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     98.00 160.00   0.50    0.28    --  110.25  18.00 -15.00  124
  2  ω    130.00 178.00   0.50    0.28    --  110.25  61.00 -90.00   96
  3  ω     97.00 173.00   0.50    0.28    --  110.25  15.00 -90.00  152
  4  ω     35.00 110.00   0.50    0.06    --   46.83  18.00 -15.00  150
  5  ω     -3.00  22.00   0.50    0.06    --  -46.83  18.00 -15.00   50
  6  ω    -72.00 -47.00   0.50    0.28    -- -102.00  61.00 -60.00   50
  7  ω    -27.00  24.00   0.50    0.06    --  -46.83  37.00 120.00  102
  8  ω     39.00  77.00   0.50    0.28    --  110.25 -61.00  90.00   76
  9  ω     42.00  67.00   0.50    0.28    --  110.25 -61.00 150.00   50
 10  ω    -26.00  13.00   0.50    0.06    --   46.83 -19.00  30.00   78
 11  ω    -27.00  -2.00   0.50    0.06    --   46.83 -18.00 175.00   50
 12  ω     49.00  80.00   0.50    0.28    --  110.25 -61.00   0.00   62
 13  ω     50.00  76.00   0.50    0.28    --  110.25 -61.00 -30.00   52
 14  ω     38.00  76.00   0.50    0.28    --  110.25 -61.00-180.00   76
 15  ω     46.00  90.00   0.50    0.06    --   46.83-125.00-120.00   88
 16  ω     71.00 110.00   0.50    0.28    --  110.25-125.00 -90.00   78
 17  ω     79.00 105.00   0.50    0.28    --  110.25 -94.00   0.00   52
 18  ω     38.00  65.00   0.50    0.28    --  110.25 -94.00   0.00   54
 19  ω     60.00 100.00   0.50    0.28    --  110.25-125.00  90.00   80
 20  ω     63.00 106.00   0.50    0.28    --  110.25 -94.00  90.00   86
 21  ω   -173.00 -99.00   0.50    0.28    -- -102.00 -45.00  90.00  148
 22  ω   -157.00 -92.00   0.50    0.28    -- -102.00 -30.00  90.00  130
 23  ω   -145.00 -92.00   0.50    0.28    -- -102.00 -18.00 175.00  106
 24  ω   -114.00 -41.00   0.50    0.06    --  -46.83 -18.00 175.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0048244000
_diffrn_orient_matrix_UB_12      -0.0160099000
_diffrn_orient_matrix_UB_13      0.0714589000
_diffrn_orient_matrix_UB_21      -0.1015806000
_diffrn_orient_matrix_UB_22      -0.0950064000
_diffrn_orient_matrix_UB_23      0.0003630000
_diffrn_orient_matrix_UB_31      0.0242457000
_diffrn_orient_matrix_UB_32      -0.3948737000
_diffrn_orient_matrix_UB_33      -0.0030101000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1983
_reflns_number_total             2461
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2461
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.047
_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)+(0.0507P)²+0.4850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1159
_refine_special_details          
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C14(H14), C7(H7), C10(H10), C4(H4), C11(H11), C5(H5), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O19(H19)
;
_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
Cl15 Cl 0.52603(4) 0.63359(19) 0.07171(2) 0.0676(2) Uani 1 1 d . . . . .
O19 O 0.24369(10) 0.7136(5) 0.32055(7) 0.0589(4) Uani 1 1 d . . . . .
H19 H 0.288702 0.735656 0.299514 0.088 Uiso 1 1 calc GR . . . .
N8 N 0.41402(10) 0.6709(4) 0.29284(7) 0.0431(4) Uani 1 1 d . . . . .
O18 O 0.41503(11) 0.0448(6) 0.56122(7) 0.0695(5) Uani 1 1 d . . . . .
N16 N 0.33672(12) 0.1409(5) 0.55080(7) 0.0502(4) Uani 1 1 d . . . . .
O17 O 0.27758(12) 0.1074(6) 0.58870(8) 0.0819(6) Uani 1 1 d . . . . .
C2 C 0.38061(12) 0.3426(5) 0.44849(8) 0.0411(4) Uani 1 1 d . . . . .
H2 H 0.440067 0.278080 0.458768 0.049 Uiso 1 1 calc R . . . .
C9 C 0.48684(12) 0.7362(5) 0.25285(9) 0.0405(4) Uani 1 1 d . . . . .
C14 C 0.47242(13) 0.6694(5) 0.18991(9) 0.0425(4) Uani 1 1 d . . . . .
H14 H 0.416775 0.584713 0.174805 0.051 Uiso 1 1 calc R . . . .
C1 C 0.35916(12) 0.4855(5) 0.39049(8) 0.0398(4) Uani 1 1 d . . . . .
C3 C 0.31318(13) 0.2969(5) 0.49082(8) 0.0414(4) Uani 1 1 d . . . . .
C7 C 0.43086(13) 0.5396(5) 0.34677(8) 0.0419(4) Uani 1 1 d . . . . .
H7 H 0.490123 0.477725 0.358159 0.050 Uiso 1 1 calc R . . . .
C6 C 0.26798(13) 0.5783(5) 0.37570(9) 0.0433(4) Uani 1 1 d . . . . .
C10 C 0.56949(13) 0.8729(5) 0.27457(9) 0.0459(4) Uani 1 1 d . . . . .
H10 H 0.579116 0.919440 0.316635 0.055 Uiso 1 1 calc R . . . .
C4 C 0.22354(13) 0.3909(6) 0.47681(9) 0.0478(5) Uani 1 1 d . . . . .
H4 H 0.179050 0.358685 0.505910 0.057 Uiso 1 1 calc R . . . .
C13 C 0.54219(14) 0.7313(5) 0.15034(9) 0.0461(4) Uani 1 1 d . . . . .
C11 C 0.63709(13) 0.9391(6) 0.23331(10) 0.0507(5) Uani 1 1 d . . . . .
H11 H 0.691993 1.033286 0.247871 0.061 Uiso 1 1 calc R . . . .
C5 C 0.20167(13) 0.5308(6) 0.41987(10) 0.0502(5) Uani 1 1 d . . . . .
H5 H 0.141957 0.595328 0.410376 0.060 Uiso 1 1 calc R . . . .
C12 C 0.62468(14) 0.8678(6) 0.17075(10) 0.0505(5) Uani 1 1 d . . . . .
H12 H 0.670616 0.910651 0.143149 0.061 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
Cl15 C13 1.743(2) . ?
O19 C6 1.333(2) . ?
N8 C9 1.420(2) . ?
N8 C7 1.281(2) . ?
O18 N16 1.224(2) . ?
N16 O17 1.220(2) . ?
N16 C3 1.453(3) . ?
C2 C1 1.389(3) . ?
C2 C3 1.382(2) . ?
C9 C14 1.390(3) . ?
C9 C10 1.391(3) . ?
C14 C13 1.377(3) . ?
C1 C7 1.453(2) . ?
C1 C6 1.416(3) . ?
C3 C4 1.392(3) . ?
C6 C5 1.398(3) . ?
C10 C11 1.380(3) . ?
C4 C5 1.366(3) . ?
C13 C12 1.380(3) . ?
C11 C12 1.381(3) . ?

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 N8 C9 119.35(16) . . ?
O18 N16 C3 118.74(16) . . ?
O17 N16 O18 122.42(18) . . ?
O17 N16 C3 118.84(17) . . ?
C3 C2 C1 119.68(17) . . ?
C14 C9 N8 117.78(17) . . ?
C14 C9 C10 120.07(17) . . ?
C10 C9 N8 122.12(17) . . ?
C13 C14 C9 118.67(18) . . ?
C2 C1 C7 119.29(16) . . ?
C2 C1 C6 119.09(16) . . ?
C6 C1 C7 121.61(17) . . ?
C2 C3 N16 118.82(17) . . ?
C2 C3 C4 121.53(18) . . ?
C4 C3 N16 119.64(17) . . ?
N8 C7 C1 121.29(17) . . ?
O19 C6 C1 121.48(17) . . ?
O19 C6 C5 118.88(17) . . ?
C5 C6 C1 119.64(17) . . ?
C11 C10 C9 119.58(18) . . ?
C5 C4 C3 119.28(17) . . ?
C14 C13 Cl15 118.97(16) . . ?
C14 C13 C12 122.30(18) . . ?
C12 C13 Cl15 118.73(15) . . ?
C10 C11 C12 121.19(19) . . ?
C4 C5 C6 120.77(18) . . ?
C13 C12 C11 118.16(18) . . ?


# start Validation Reply Form
_vrf_PLAT068_I                   
;
PROBLEM: Reported F000 Differs from Calcd (or Missing)...
RESPONSE: The output by SHELXL of population parameters to the CIF 
with only two decimals. Note: SHELXL counts the number of electrons 
in the unit cell. The result will in general be an integer.
;
_vrf_PLAT911_I                   
;
PROBLEM: Missing # FCF Refl Between THmin & STh/L= 0.600 3
RESPONSE: These reflections were probably affected by unexpected deviations
in their intensities for symmetry equivalent measurements and omitted during
initial data reduction.
;
# end Validation Reply Form
