# 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 2023

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

data_MAA24
_database_code_depnum_ccdc_archive 'CCDC 2176927'
loop_
_audit_author_name
_audit_author_address
'Aijaz Dar'
;University of Kashmir
India
;
_audit_update_record             
;
2022-06-04 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H8 Br Cl I N O'
_chemical_formula_sum            'C13 H8 Br Cl I N O'
_chemical_formula_weight         436.45

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.0186(5)
_cell_length_b                   11.8251(6)
_cell_length_c                   14.9370(8)
_cell_angle_alpha                89.886(2)
_cell_angle_beta                 88.569(2)
_cell_angle_gamma                80.020(2)
_cell_volume                     1394.47(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4056
_cell_measurement_theta_min      2.3450
_cell_measurement_theta_max      25.0000

_exptl_crystal_description       Needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.079
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.0981
_exptl_crystal_size_min          0.0819
_exptl_absorpt_coefficient_mu    5.338
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91468
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27786
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.215
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_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             4923
_reflns_number_gt                4056
_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-2018/1 (Sheldrick, 2018)'
_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)+(0.1204P)²+3.1889P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4923
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0698
_refine_ls_wR_factor_ref         0.1962
_refine_ls_wR_factor_gt          0.1828
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_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
I1 I 0.51684(8) 0.30967(5) 0.24411(3) 0.0723(2) Uani 1 1 d . . . . .
I2 I 0.08486(11) 0.13258(5) 0.07980(5) 0.0884(3) Uani 1 1 d . . . . .
Br1 Br 1.04976(14) 0.97130(8) 0.68092(7) 0.0818(3) Uani 1 1 d . . . . .
Br2 Br 0.57725(13) 0.96995(8) 0.17952(6) 0.0760(3) Uani 1 1 d . . . . .
Cl2 Cl 0.0146(3) 0.30979(19) -0.26973(13) 0.0682(5) Uani 1 1 d . . . . .
Cl1 Cl 0.5683(3) 0.1066(2) 0.58524(14) 0.0745(6) Uani 1 1 d . . . . .
O1 O 0.6743(7) 0.4875(5) 0.3607(3) 0.0635(13) Uani 1 1 d . . . . .
H1 H 0.712676 0.535214 0.390049 0.095 Uiso 1 1 calc R U . . .
O2 O 0.2152(7) 0.3652(5) 0.0940(4) 0.0675(14) Uani 1 1 d . . . . .
H2 H 0.249179 0.425984 0.101226 0.101 Uiso 1 1 calc R U . . .
N2 N 0.2983(7) 0.5571(5) 0.0478(4) 0.0526(14) Uani 1 1 d . . . . .
N1 N 0.7897(7) 0.5743(5) 0.5042(4) 0.0526(14) Uani 1 1 d . . . . .
C15 C 0.4837(10) 0.7510(6) 0.1919(5) 0.0593(18) Uani 1 1 d . . . . .
H15 H 0.522868 0.750792 0.249953 0.071 Uiso 1 1 calc R U . . .
C16 C 0.4183(9) 0.6575(6) 0.1590(5) 0.0555(17) Uani 1 1 d . . . . .
H16 H 0.413560 0.594451 0.195635 0.067 Uiso 1 1 calc R U . . .
C8 C 0.6917(8) 0.3943(6) 0.5044(5) 0.0489(15) Uani 1 1 d . . . . .
C6 C 0.9760(10) 0.7465(7) 0.6737(6) 0.0611(19) Uani 1 1 d . . . . .
H6 H 1.017961 0.740059 0.731283 0.073 Uiso 1 1 calc R U . . .
C5 C 0.9205(9) 0.6542(6) 0.6343(6) 0.0593(18) Uani 1 1 d . . . . .
H5 H 0.928313 0.585056 0.665086 0.071 Uiso 1 1 calc R U . . .
C11 C 0.5655(8) 0.2157(6) 0.4274(5) 0.0493(15) Uani 1 1 d . . . . .
H11 H 0.524399 0.154191 0.402589 0.059 Uiso 1 1 calc R U . . .
C21 C 0.1719(8) 0.3565(6) 0.0087(5) 0.0496(16) Uani 1 1 d . . . . .
C7 C 0.7569(9) 0.4900(6) 0.5461(5) 0.0534(16) Uani 1 1 d . . . . .
H7 H 0.774463 0.486971 0.607473 0.064 Uiso 1 1 calc R U . . .
C25 C 0.1344(9) 0.4266(8) -0.1422(5) 0.0617(19) Uani 1 1 d . . . . .
H25 H 0.141648 0.483111 -0.184839 0.074 Uiso 1 1 calc R U . . .
C1 C 0.9690(9) 0.8472(6) 0.6274(5) 0.0548(17) Uani 1 1 d . . . . .
C10 C 0.5871(8) 0.3063(6) 0.3769(5) 0.0499(16) Uani 1 1 d . . . . .
C23 C 0.0605(8) 0.2435(7) -0.1019(5) 0.0545(17) Uani 1 1 d . . . . .
H23 H 0.018537 0.178161 -0.118154 0.065 Uiso 1 1 calc R U . . .
C20 C 0.1838(8) 0.4397(6) -0.0544(5) 0.0494(15) Uani 1 1 d . . . . .
C9 C 0.6527(8) 0.3996(6) 0.4132(5) 0.0479(15) Uani 1 1 d . . . . .
C14 C 0.4887(9) 0.8443(6) 0.1355(5) 0.0537(16) Uani 1 1 d . . . . .
C22 C 0.1090(9) 0.2577(6) -0.0164(5) 0.0550(17) Uani 1 1 d . . . . .
C17 C 0.3608(8) 0.6577(6) 0.0730(5) 0.0480(15) Uani 1 1 d . . . . .
C4 C 0.8540(7) 0.6639(6) 0.5502(5) 0.0453(14) Uani 1 1 d . . . . .
C24 C 0.0752(9) 0.3287(7) -0.1641(5) 0.0561(17) Uani 1 1 d . . . . .
C12 C 0.6058(9) 0.2152(6) 0.5181(5) 0.0548(17) Uani 1 1 d . . . . .
C13 C 0.6656(9) 0.3029(6) 0.5561(5) 0.0558(17) Uani 1 1 d . . . . .
H13 H 0.688964 0.301355 0.616777 0.067 Uiso 1 1 calc R U . . .
C3 C 0.8515(10) 0.7660(7) 0.5041(5) 0.0590(18) Uani 1 1 d . . . . .
H3 H 0.811050 0.772812 0.446188 0.071 Uiso 1 1 calc R U . . .
C2 C 0.9071(11) 0.8564(7) 0.5423(5) 0.0625(19) Uani 1 1 d . . . . .
H2A H 0.903213 0.924614 0.510683 0.075 Uiso 1 1 calc R U . . .
C19 C 0.2488(8) 0.5423(6) -0.0309(5) 0.0525(16) Uani 1 1 d . . . . .
H19 H 0.254579 0.598270 -0.074143 0.063 Uiso 1 1 calc R U . . .
C18 C 0.4307(11) 0.8434(7) 0.0502(5) 0.0618(19) Uani 1 1 d . . . . .
H18 H 0.434004 0.906312 0.013111 0.074 Uiso 1 1 calc R U . . .
C26 C 0.3687(11) 0.7520(7) 0.0192(5) 0.0627(19) Uani 1 1 d . . . . .
H26 H 0.330867 0.752530 -0.039213 0.075 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C10 2.074(7) . ?
I2 C22 2.090(8) . ?
Br1 C1 1.890(7) . ?
Br2 C14 1.880(7) . ?
Cl2 C24 1.689(7) . ?
Cl1 C12 1.691(7) . ?
O1 C9 1.334(8) . ?
O1 H1 0.8200 . ?
O2 C21 1.338(8) . ?
O2 H2 0.8200 . ?
N2 C19 1.273(9) . ?
N2 C17 1.424(9) . ?
N1 C7 1.239(9) . ?
N1 C4 1.439(8) . ?
C15 C14 1.392(11) . ?
C15 C16 1.398(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(10) . ?
C16 H16 0.9300 . ?
C8 C13 1.370(10) . ?
C8 C9 1.404(10) . ?
C8 C7 1.472(10) . ?
C6 C1 1.369(11) . ?
C6 C5 1.386(10) . ?
C6 H6 0.9300 . ?
C5 C4 1.375(11) . ?
C5 H5 0.9300 . ?
C11 C10 1.343(10) . ?
C11 C12 1.400(10) . ?
C11 H11 0.9300 . ?
C21 C20 1.375(10) . ?
C21 C22 1.405(10) . ?
C7 H7 0.9300 . ?
C25 C24 1.369(11) . ?
C25 C20 1.396(10) . ?
C25 H25 0.9300 . ?
C1 C2 1.374(11) . ?
C10 C9 1.415(10) . ?
C23 C22 1.363(10) . ?
C23 C24 1.387(11) . ?
C23 H23 0.9300 . ?
C20 C19 1.447(10) . ?
C14 C18 1.369(11) . ?
C17 C26 1.383(11) . ?
C4 C3 1.386(11) . ?
C12 C13 1.347(10) . ?
C13 H13 0.9300 . ?
C3 C2 1.358(11) . ?
C3 H3 0.9300 . ?
C2 H2A 0.9300 . ?
C19 H19 0.9300 . ?
C18 C26 1.353(11) . ?
C18 H18 0.9300 . ?
C26 H26 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
C9 O1 H1 109.5 . . ?
C21 O2 H2 109.5 . . ?
C19 N2 C17 122.3(7) . . ?
C7 N1 C4 120.2(7) . . ?
C14 C15 C16 118.4(7) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C17 C16 C15 120.8(7) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C13 C8 C9 121.1(6) . . ?
C13 C8 C7 119.2(6) . . ?
C9 C8 C7 119.7(7) . . ?
C1 C6 C5 119.8(7) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C4 C5 C6 120.5(7) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C10 C11 C12 118.9(6) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
O2 C21 C20 123.2(7) . . ?
O2 C21 C22 117.8(7) . . ?
C20 C21 C22 119.0(6) . . ?
N1 C7 C8 123.7(7) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C24 C25 C20 118.4(8) . . ?
C24 C25 H25 120.8 . . ?
C20 C25 H25 120.8 . . ?
C6 C1 C2 120.0(7) . . ?
C6 C1 Br1 119.3(6) . . ?
C2 C1 Br1 120.7(6) . . ?
C11 C10 C9 121.3(7) . . ?
C11 C10 I1 118.6(5) . . ?
C9 C10 I1 120.0(5) . . ?
C22 C23 C24 118.6(7) . . ?
C22 C23 H23 120.7 . . ?
C24 C23 H23 120.7 . . ?
C21 C20 C25 120.7(7) . . ?
C21 C20 C19 120.5(6) . . ?
C25 C20 C19 118.8(7) . . ?
O1 C9 C8 123.0(6) . . ?
O1 C9 C10 119.6(7) . . ?
C8 C9 C10 117.3(6) . . ?
C18 C14 C15 120.2(7) . . ?
C18 C14 Br2 121.4(6) . . ?
C15 C14 Br2 118.4(6) . . ?
C23 C22 C21 121.0(7) . . ?
C23 C22 I2 119.7(6) . . ?
C21 C22 I2 119.2(5) . . ?
C16 C17 C26 119.0(6) . . ?
C16 C17 N2 115.1(6) . . ?
C26 C17 N2 125.9(7) . . ?
C5 C4 C3 118.5(6) . . ?
C5 C4 N1 124.9(6) . . ?
C3 C4 N1 116.6(6) . . ?
C25 C24 C23 122.3(7) . . ?
C25 C24 Cl2 119.8(7) . . ?
C23 C24 Cl2 118.0(5) . . ?
C13 C12 C11 122.0(7) . . ?
C13 C12 Cl1 117.7(6) . . ?
C11 C12 Cl1 120.2(5) . . ?
C12 C13 C8 119.3(7) . . ?
C12 C13 H13 120.3 . . ?
C8 C13 H13 120.3 . . ?
C2 C3 C4 121.0(7) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C2 C1 120.1(7) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
N2 C19 C20 121.1(7) . . ?
N2 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C26 C18 C14 120.7(7) . . ?
C26 C18 H18 119.6 . . ?
C14 C18 H18 119.6 . . ?
C18 C26 C17 120.9(7) . . ?
C18 C26 H26 119.5 . . ?
C17 C26 H26 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C15 C16 C17 0.2(12) . . . . ?
C1 C6 C5 C4 -1.8(12) . . . . ?
C4 N1 C7 C8 -179.6(6) . . . . ?
C13 C8 C7 N1 177.5(7) . . . . ?
C9 C8 C7 N1 -4.4(10) . . . . ?
C5 C6 C1 C2 0.0(12) . . . . ?
C5 C6 C1 Br1 -178.6(6) . . . . ?
C12 C11 C10 C9 1.3(10) . . . . ?
C12 C11 C10 I1 -177.3(5) . . . . ?
O2 C21 C20 C25 -179.1(6) . . . . ?
C22 C21 C20 C25 -0.1(10) . . . . ?
O2 C21 C20 C19 1.3(10) . . . . ?
C22 C21 C20 C19 -179.7(6) . . . . ?
C24 C25 C20 C21 -0.5(10) . . . . ?
C24 C25 C20 C19 179.1(6) . . . . ?
C13 C8 C9 O1 179.2(6) . . . . ?
C7 C8 C9 O1 1.2(10) . . . . ?
C13 C8 C9 C10 -0.6(10) . . . . ?
C7 C8 C9 C10 -178.7(6) . . . . ?
C11 C10 C9 O1 179.2(6) . . . . ?
I1 C10 C9 O1 -2.3(8) . . . . ?
C11 C10 C9 C8 -0.9(9) . . . . ?
I1 C10 C9 C8 177.6(4) . . . . ?
C16 C15 C14 C18 0.0(12) . . . . ?
C16 C15 C14 Br2 -179.8(6) . . . . ?
C24 C23 C22 C21 0.3(10) . . . . ?
C24 C23 C22 I2 178.9(5) . . . . ?
O2 C21 C22 C23 179.3(6) . . . . ?
C20 C21 C22 C23 0.2(10) . . . . ?
O2 C21 C22 I2 0.6(8) . . . . ?
C20 C21 C22 I2 -178.5(5) . . . . ?
C15 C16 C17 C26 0.1(11) . . . . ?
C15 C16 C17 N2 179.7(7) . . . . ?
C19 N2 C17 C16 -176.4(6) . . . . ?
C19 N2 C17 C26 3.1(10) . . . . ?
C6 C5 C4 C3 3.1(11) . . . . ?
C6 C5 C4 N1 -178.6(7) . . . . ?
C7 N1 C4 C5 15.8(10) . . . . ?
C7 N1 C4 C3 -165.9(7) . . . . ?
C20 C25 C24 C23 0.9(11) . . . . ?
C20 C25 C24 Cl2 -179.9(5) . . . . ?
C22 C23 C24 C25 -0.8(11) . . . . ?
C22 C23 C24 Cl2 -180.0(5) . . . . ?
C10 C11 C12 C13 0.0(11) . . . . ?
C10 C11 C12 Cl1 176.0(5) . . . . ?
C11 C12 C13 C8 -1.5(12) . . . . ?
Cl1 C12 C13 C8 -177.7(6) . . . . ?
C9 C8 C13 C12 1.8(11) . . . . ?
C7 C8 C13 C12 179.9(7) . . . . ?
C5 C4 C3 C2 -2.6(11) . . . . ?
N1 C4 C3 C2 179.0(7) . . . . ?
C4 C3 C2 C1 0.8(12) . . . . ?
C6 C1 C2 C3 0.6(12) . . . . ?
Br1 C1 C2 C3 179.1(6) . . . . ?
C17 N2 C19 C20 -179.2(6) . . . . ?
C21 C20 C19 N2 0.9(10) . . . . ?
C25 C20 C19 N2 -178.7(6) . . . . ?
C15 C14 C18 C26 -0.4(12) . . . . ?
Br2 C14 C18 C26 179.4(7) . . . . ?
C14 C18 C26 C17 0.6(13) . . . . ?
C16 C17 C26 C18 -0.5(12) . . . . ?
N2 C17 C26 C18 180.0(7) . . . . ?

_refine_diff_density_max         3.392
_refine_diff_density_min         -1.170
_refine_diff_density_rms         0.229

####################################################################### 
# 
# 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_MAA15
_database_code_depnum_ccdc_archive 'CCDC 2176928'
loop_
_audit_author_name
_audit_author_address
'Aijaz Dar'
;University of Kashmir
India
;
_audit_update_record             
;
2022-06-04 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H8 Cl I2 N O'
_chemical_formula_sum            'C13 H8 Cl I2 N O'
_chemical_formula_weight         483.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.9582(2)
_cell_length_b                   8.5499(2)
_cell_length_c                   11.2354(3)
_cell_angle_alpha                87.144(2)
_cell_angle_beta                 76.439(2)
_cell_angle_gamma                66.457(3)
_cell_volume                     680.48(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2251
_cell_measurement_theta_min      2.3450
_cell_measurement_theta_max      25.0000

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.364
_exptl_crystal_F_000             450
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    4.804
_shelx_estimated_absorpt_T_min   0.596
_shelx_estimated_absorpt_T_max   0.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91468
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4832
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.602
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2387
_reflns_number_gt                2251
_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 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0244P)²+1.0701P] 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         2387
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0228
_refine_ls_R_factor_gt           0.0210
_refine_ls_wR_factor_ref         0.0512
_refine_ls_wR_factor_gt          0.0501
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.054
_refine_ls_shift/su_mean         0.002

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
I1 I 0.71804(3) 0.13346(3) 0.99112(2) 0.03025(9) Uani 1 1 d . . . . .
I2 I 0.11719(3) 0.33103(3) 0.12351(2) 0.03067(9) Uani 1 1 d . . . . .
Cl1 Cl -0.19685(13) 1.02483(11) 0.30852(9) 0.0338(2) Uani 1 1 d . . . . .
O1 O 0.2884(3) 0.3084(3) 0.3483(2) 0.0285(6) Uani 1 1 d . . . . .
N1 N 0.3454(4) 0.3979(4) 0.5447(3) 0.0240(6) Uani 1 1 d . . . . .
C4 C 0.4274(4) 0.3486(4) 0.6471(3) 0.0218(7) Uani 1 1 d . . . . .
C3 C 0.4197(5) 0.4598(4) 0.7360(3) 0.0256(7) Uani 1 1 d . . . . .
H3 H 0.357087 0.579580 0.729916 0.031 Uiso 1 1 calc R U . . .
C5 C 0.5219(5) 0.1742(5) 0.6567(3) 0.0273(8) Uani 1 1 d . . . . .
H5 H 0.529874 0.097142 0.595486 0.033 Uiso 1 1 calc R U . . .
C1 C 0.5946(4) 0.2233(4) 0.8418(3) 0.0231(7) Uani 1 1 d . . . . .
C11 C -0.0309(5) 0.6922(4) 0.2353(3) 0.0244(7) Uani 1 1 d . . . . .
H11 H -0.090372 0.725313 0.168623 0.029 Uiso 1 1 calc R U . . .
C12 C -0.0564(5) 0.8118(4) 0.3228(3) 0.0247(7) Uani 1 1 d . . . . .
C9 C 0.1750(5) 0.4726(4) 0.3422(3) 0.0235(7) Uani 1 1 d . . . . .
C8 C 0.1448(5) 0.5979(4) 0.4306(3) 0.0230(7) Uani 1 1 d . . . . .
C2 C 0.5025(5) 0.3977(4) 0.8337(3) 0.0266(8) Uani 1 1 d . . . . .
H2 H 0.496007 0.474414 0.894602 0.032 Uiso 1 1 calc R U . . .
C6 C 0.6048(5) 0.1104(4) 0.7539(3) 0.0278(8) Uani 1 1 d . . . . .
H6 H 0.667802 -0.009267 0.760053 0.033 Uiso 1 1 calc R U . . .
C10 C 0.0836(5) 0.5216(4) 0.2461(3) 0.0228(7) Uani 1 1 d . . . . .
C7 C 0.2316(5) 0.5515(4) 0.5344(3) 0.0234(7) Uani 1 1 d . . . . .
H7 H 0.203588 0.636548 0.595841 0.028 Uiso 1 1 calc R U . . .
C13 C 0.0280(5) 0.7678(4) 0.4199(3) 0.0255(7) Uani 1 1 d . . . . .
H13 H 0.006933 0.852638 0.479608 0.031 Uiso 1 1 calc R U . . .
H1A H 0.337(8) 0.316(7) 0.418(6) 0.079(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
I1 C1 2.100(3) . ?
I2 C10 2.080(3) . ?
Cl1 C12 1.738(3) . ?
O1 C9 1.341(4) . ?
O1 H1A 0.96(6) . ?
N1 C7 1.281(4) . ?
N1 C4 1.419(4) . ?
C4 C5 1.388(5) . ?
C4 C3 1.388(5) . ?
C3 C2 1.386(5) . ?
C3 H3 0.9500 . ?
C5 C6 1.384(5) . ?
C5 H5 0.9500 . ?
C1 C6 1.381(5) . ?
C1 C2 1.384(5) . ?
C11 C12 1.377(5) . ?
C11 C10 1.395(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.373(5) . ?
C9 C10 1.397(5) . ?
C9 C8 1.407(5) . ?
C8 C13 1.394(5) . ?
C8 C7 1.452(5) . ?
C2 H2 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 H1A 101(3) . . ?
C7 N1 C4 122.1(3) . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 N1 115.9(3) . . ?
C3 C4 N1 125.3(3) . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C6 C1 C2 120.8(3) . . ?
C6 C1 I1 120.6(2) . . ?
C2 C1 I1 118.6(2) . . ?
C12 C11 C10 118.9(3) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C13 C12 C11 121.8(3) . . ?
C13 C12 Cl1 119.2(3) . . ?
C11 C12 Cl1 118.9(3) . . ?
O1 C9 C10 119.5(3) . . ?
O1 C9 C8 121.8(3) . . ?
C10 C9 C8 118.8(3) . . ?
C13 C8 C9 119.9(3) . . ?
C13 C8 C7 119.5(3) . . ?
C9 C8 C7 120.6(3) . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C1 C6 C5 119.1(3) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 I2 121.3(2) . . ?
C9 C10 I2 117.8(2) . . ?
N1 C7 C8 121.1(3) . . ?
N1 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C12 C13 C8 119.7(3) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?

_refine_diff_density_max         0.623
_refine_diff_density_min         -0.809
_refine_diff_density_rms         0.099

####################################################################### 
# 
# 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_MAA28
_database_code_depnum_ccdc_archive 'CCDC 2176929'
loop_
_audit_author_name
_audit_author_address
'Aijaz Dar'
;University of Kashmir
India
;
_audit_update_record             
;
2022-06-04 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_audit_creation_date             2019-10-23
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 Cl2 I N O'
_chemical_formula_sum            'C13 H8 Cl2 I N O'
_chemical_formula_weight         392.00
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

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

_cell_length_a                   7.9091(5)
_cell_length_b                   8.4598(6)
_cell_length_c                   11.0761(7)
_cell_angle_alpha                86.407(5)
_cell_angle_beta                 74.604(6)
_cell_angle_gamma                64.696(7)
_cell_volume                     644.85(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4599
_cell_measurement_temperature    150
_cell_measurement_theta_max      31.1120
_cell_measurement_theta_min      2.6730
_shelx_estimated_absorpt_T_max   0.869
_shelx_estimated_absorpt_T_min   0.596
_exptl_absorpt_coefficient_mu    2.882
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.019
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7191
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.046
_diffrn_reflns_theta_min         2.668
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   1.00    4.00    --  -20.00   0.00  36.00  180
  2  ω    -62.00  19.00   1.00    4.00    --  -20.00 -72.00-180.00   81
  3  ω    -62.00  19.00   1.00    4.00    --  -20.00 -72.00  36.00   81
  4  ω    -39.00   4.00   1.00    4.00    --  -20.00  72.00 -36.00   43
  5  ω     -9.00  22.00   1.00    4.00    --  -20.00  72.00 108.00   31
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0009881000
_diffrn_orient_matrix_UB_12      0.0663778000
_diffrn_orient_matrix_UB_13      -0.0422332000
_diffrn_orient_matrix_UB_21      0.0474682000
_diffrn_orient_matrix_UB_22      -0.0638349000
_diffrn_orient_matrix_UB_23      -0.0509203000
_diffrn_orient_matrix_UB_31      -0.0912517000
_diffrn_orient_matrix_UB_32      0.0122193000
_diffrn_orient_matrix_UB_33      -0.0071037000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3141
_reflns_number_total             3698
_reflns_odcompleteness_completeness 89.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.98
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.878
_refine_diff_density_min         -1.483
_refine_diff_density_rms         0.239
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3698
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      0.936
_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)+(0.0637P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1080
_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:
 C13(H13), C3(H3), C1(H1A), C9(H9), C12(H12), C7(H7), C10(H10)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
I1 I 0.70551(3) 0.11640(3) 0.99742(2) 0.02584(10) Uani 1 1 d . . . . .
Cl1 Cl 0.12821(15) 0.36724(14) 0.12620(9) 0.0305(2) Uani 1 1 d . . . . .
Cl2 Cl -0.20391(15) 1.04059(12) 0.30332(9) 0.0300(2) Uani 1 1 d . . . . .
O1 O 0.2981(4) 0.3006(3) 0.3375(2) 0.0245(6) Uani 1 1 d . . . . .
H1 H 0.3525 0.2880 0.3953 0.037 Uiso 1 1 calc GR . . . .
N1 N 0.3470(4) 0.3890(4) 0.5408(3) 0.0186(6) Uani 1 1 d . . . . .
C13 C 0.5348(5) 0.1582(5) 0.6515(3) 0.0204(7) Uani 1 1 d . . . . .
H13 H 0.5558 0.0792 0.5860 0.024 Uiso 1 1 calc R . . . .
C3 C 0.0235(5) 0.7718(5) 0.4152(3) 0.0206(7) Uani 1 1 d . . . . .
H3 H -0.0030 0.8572 0.4779 0.025 Uiso 1 1 calc R . . . .
C4 C 0.1444(5) 0.5974(5) 0.4245(3) 0.0171(6) Uani 1 1 d . . . . .
C8 C 0.4253(5) 0.3377(5) 0.6452(3) 0.0172(6) Uani 1 1 d . . . . .
C1 C -0.0247(5) 0.6974(5) 0.2255(3) 0.0203(7) Uani 1 1 d . . . . .
H1A H -0.0827 0.7317 0.1576 0.024 Uiso 1 1 calc R . . . .
C9 C 0.4011(5) 0.4505(5) 0.7402(4) 0.0232(7) Uani 1 1 d . . . . .
H9 H 0.3286 0.5729 0.7366 0.028 Uiso 1 1 calc R . . . .
C12 C 0.6129(5) 0.0943(5) 0.7518(4) 0.0235(7) Uani 1 1 d . . . . .
H12 H 0.6840 -0.0282 0.7564 0.028 Uiso 1 1 calc R . . . .
C2 C -0.0579(5) 0.8215(5) 0.3157(3) 0.0206(7) Uani 1 1 d . . . . .
C6 C 0.0920(5) 0.5253(5) 0.2353(3) 0.0201(7) Uani 1 1 d . . . . .
C5 C 0.1833(5) 0.4699(5) 0.3328(3) 0.0199(7) Uani 1 1 d . . . . .
C7 C 0.2284(5) 0.5471(5) 0.5310(3) 0.0197(7) Uani 1 1 d . . . . .
H7 H 0.1943 0.6336 0.5948 0.024 Uiso 1 1 calc R . . . .
C10 C 0.4806(5) 0.3884(5) 0.8405(4) 0.0230(7) Uani 1 1 d . . . . .
H10 H 0.4625 0.4675 0.9050 0.028 Uiso 1 1 calc R . . . .
C11 C 0.5866(5) 0.2100(5) 0.8458(3) 0.0195(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C11 2.090(3) . ?
Cl1 C6 1.739(3) . ?
Cl2 C2 1.735(4) . ?
O1 H1 0.8400 . ?
O1 C5 1.335(4) . ?
N1 C8 1.413(4) . ?
N1 C7 1.282(5) . ?
C13 H13 0.9500 . ?
C13 C8 1.399(5) . ?
C13 C12 1.383(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(5) . ?
C3 C2 1.376(5) . ?
C4 C5 1.405(5) . ?
C4 C7 1.458(5) . ?
C8 C9 1.384(5) . ?
C1 H1A 0.9500 . ?
C1 C2 1.388(5) . ?
C1 C6 1.367(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(5) . ?
C12 H12 0.9500 . ?
C12 C11 1.387(5) . ?
C6 C5 1.403(5) . ?
C7 H7 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.385(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
C5 O1 H1 109.5 . . ?
C7 N1 C8 122.2(3) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C8 120.8(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.3(3) . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 C7 119.5(3) . . ?
C5 C4 C7 120.2(3) . . ?
C13 C8 N1 116.4(3) . . ?
C9 C8 N1 125.2(3) . . ?
C9 C8 C13 118.4(3) . . ?
C2 C1 H1A 120.3 . . ?
C6 C1 H1A 120.3 . . ?
C6 C1 C2 119.4(3) . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121.3(3) . . ?
C10 C9 H9 119.3 . . ?
C13 C12 H12 120.2 . . ?
C13 C12 C11 119.6(4) . . ?
C11 C12 H12 120.2 . . ?
C3 C2 Cl2 119.8(3) . . ?
C3 C2 C1 120.4(3) . . ?
C1 C2 Cl2 119.8(3) . . ?
C1 C6 Cl1 120.0(3) . . ?
C1 C6 C5 122.0(3) . . ?
C5 C6 Cl1 118.0(3) . . ?
O1 C5 C4 122.7(3) . . ?
O1 C5 C6 119.8(3) . . ?
C6 C5 C4 117.5(3) . . ?
N1 C7 C4 121.7(3) . . ?
N1 C7 H7 119.2 . . ?
C4 C7 H7 119.2 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.4(3) . . ?
C11 C10 H10 120.3 . . ?
C12 C11 I1 120.2(3) . . ?
C12 C11 C10 120.4(3) . . ?
C10 C11 I1 119.3(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.439
_oxdiff_exptl_absorpt_empirical_full_min 0.738
