# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc1hzxs5
_database_code_depnum_ccdc_archive 'CCDC 1400108'
_audit_update_record             
;
2015-05-09 deposited with the CCDC.	2026-02-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        'L-histidine Iodide'
_chemical_name_common            ?
_chemical_melting_point          293
_chemical_formula_moiety         'C6 H10 I N3 O2'
_chemical_formula_sum            'C6 H10 I N3 O2'
_chemical_formula_weight         282.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4740 1.8120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.8399(8)
_cell_length_b                   9.4995(8)
_cell_length_c                   24.376(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1815.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.071
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    3.494
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18694
_diffrn_reflns_av_unetI/netI     0.1732
_diffrn_reflns_av_R_equivalents  0.1178
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.299
_diffrn_reflns_theta_max         31.713
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5760
_reflns_number_gt                3375
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_max     0.954
_reflns_Friedel_fraction_full    1.000

_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    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0128P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1.05(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5760
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.0829
_refine_ls_wR_factor_gt          0.0739
_refine_ls_goodness_of_fit_ref   0.777
_refine_ls_restrained_S_all      0.777
_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 0.4412(7) 0.8638(6) 0.2213(2) 0.0205(13) Uani 1 1 d . . . . .
O2 O 0.4471(7) 0.6845(6) 0.2806(2) 0.0154(13) Uani 1 1 d . . . . .
N1 N 0.6672(9) 0.3772(8) 0.0440(3) 0.0243(19) Uani 1 1 d . . . . .
H1 H 0.6863 0.3617 0.0098 0.029 Uiso 1 1 d R U . . .
N2 N 0.6174(8) 0.3439(8) 0.1295(3) 0.0135(16) Uani 1 1 d . . . . .
H2 H 0.5986 0.3031 0.1604 0.016 Uiso 1 1 d R U . . .
N3 N 0.3414(8) 0.5036(7) 0.2023(3) 0.0147(15) Uani 1 1 d . . . . .
H3A H 0.3376 0.4424 0.1747 0.018 Uiso 1 1 d R U . . .
H3B H 0.2358 0.5277 0.2118 0.018 Uiso 1 1 d R U . . .
H3C H 0.3937 0.4643 0.2309 0.018 Uiso 1 1 d R U . . .
C1 C 0.6351(10) 0.2787(10) 0.0816(4) 0.018(2) Uani 1 1 d . . . . .
H1A H 0.6265 0.1823 0.0755 0.022 Uiso 1 1 calc R U . . .
C2 C 0.6639(10) 0.5069(9) 0.0685(4) 0.0175(18) Uani 1 1 d . . . . .
H2A H 0.6796 0.5932 0.0512 0.021 Uiso 1 1 calc R U . . .
C3 C 0.6335(10) 0.4862(9) 0.1224(4) 0.0128(19) Uani 1 1 d . . . . .
C4 C 0.6195(9) 0.5904(10) 0.1686(3) 0.0161(19) Uani 1 1 d . . . . .
H4A H 0.6806 0.6751 0.1583 0.019 Uiso 1 1 calc R U . . .
H4B H 0.6758 0.5513 0.2006 0.019 Uiso 1 1 calc R U . . .
C5 C 0.4368(11) 0.6315(9) 0.1848(3) 0.0130(17) Uani 1 1 d . . . . .
H5A H 0.3792 0.6749 0.1534 0.016 Uiso 1 1 calc R U . . .
C6 C 0.4429(11) 0.7368(8) 0.2331(3) 0.0139(18) Uani 1 1 d . . . . .
O3 O -0.0551(7) 1.1628(6) 0.2791(2) 0.0199(13) Uani 1 1 d . . . . .
O4 O 0.1589(7) 1.2824(6) 0.2419(2) 0.0214(14) Uani 1 1 d . . . . .
N4 N -0.0486(9) 0.8292(7) 0.0431(3) 0.0181(17) Uani 1 1 d . . . . .
H4 H -0.0583 0.8079 0.0089 0.022 Uiso 1 1 d R U . . .
N5 N -0.0069(8) 0.8094(7) 0.1290(3) 0.0155(17) Uani 1 1 d . . . . .
H5 H 0.0143 0.7732 0.1606 0.019 Uiso 1 1 d R U . . .
N6 N 0.2451(8) 1.0856(8) 0.1702(3) 0.0144(16) Uani 1 1 d . . . . .
H6A H 0.2593 1.0163 0.1461 0.017 Uiso 1 1 d R U . . .
H6B H 0.3348 1.0892 0.1925 0.017 Uiso 1 1 d R U . . .
H6C H 0.2351 1.1671 0.1525 0.017 Uiso 1 1 d R U . . .
C7 C -0.0764(11) 0.9605(9) 0.0650(4) 0.020(2) Uani 1 1 d . . . . .
H7 H -0.1073 1.0418 0.0462 0.024 Uiso 1 1 calc R U . . .
C8 C -0.0049(10) 0.7419(10) 0.0820(4) 0.021(2) Uani 1 1 d . . . . .
H8 H 0.0229 0.6475 0.0772 0.025 Uiso 1 1 calc R U . . .
C9 C -0.0497(11) 0.9470(8) 0.1194(3) 0.0113(17) Uani 1 1 d . . . . .
C10 C -0.0680(11) 1.0525(9) 0.1644(3) 0.0141(18) Uani 1 1 d . . . . .
H10A H -0.1683 1.0294 0.1860 0.017 Uiso 1 1 calc R U . . .
H10B H -0.0861 1.1447 0.1484 0.017 Uiso 1 1 calc R U . . .
C11 C 0.0881(10) 1.0592(9) 0.2029(3) 0.0147(19) Uani 1 1 d . . . . .
H11 H 0.0994 0.9698 0.2226 0.018 Uiso 1 1 calc R U . . .
C12 C 0.0645(11) 1.1797(8) 0.2444(3) 0.0124(17) Uani 1 1 d . . . . .
I1 I 0.43926(8) 0.90003(6) 0.06391(2) 0.02298(16) Uani 1 1 d . . . . .
I2 I 0.17079(7) 0.35618(6) 0.07310(3) 0.02417(16) 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
O1 C6 1.241(9) . ?
O2 C6 1.259(9) . ?
N1 C1 1.335(11) . ?
N1 C2 1.369(11) . ?
N1 H1 0.8599 . ?
N2 C1 1.329(11) . ?
N2 C3 1.368(10) . ?
N2 H2 0.8600 . ?
N3 C5 1.489(10) . ?
N3 H3A 0.8901 . ?
N3 H3B 0.8901 . ?
N3 H3C 0.8899 . ?
C1 H1A 0.9300 . ?
C2 C3 1.350(12) . ?
C2 H2A 0.9300 . ?
C3 C4 1.504(11) . ?
C4 C5 1.536(11) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.547(10) . ?
C5 H5A 0.9800 . ?
O3 C12 1.273(9) . ?
O4 C12 1.225(9) . ?
N4 C8 1.307(11) . ?
N4 C7 1.374(10) . ?
N4 H4 0.8600 . ?
N5 C8 1.313(11) . ?
N5 C9 1.370(10) . ?
N5 H5 0.8599 . ?
N6 C11 1.488(9) . ?
N6 H6A 0.8900 . ?
N6 H6B 0.8899 . ?
N6 H6C 0.8901 . ?
C7 C9 1.350(11) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.493(10) . ?
C10 C11 1.543(11) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.540(11) . ?
C11 H11 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
C1 N1 C2 109.1(7) . . ?
C1 N1 H1 125.4 . . ?
C2 N1 H1 125.5 . . ?
C1 N2 C3 109.9(8) . . ?
C1 N2 H2 125.2 . . ?
C3 N2 H2 124.9 . . ?
C5 N3 H3A 109.4 . . ?
C5 N3 H3B 109.3 . . ?
H3A N3 H3B 109.5 . . ?
C5 N3 H3C 109.7 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
N2 C1 N1 107.2(8) . . ?
N2 C1 H1A 126.4 . . ?
N1 C1 H1A 126.4 . . ?
C3 C2 N1 107.3(7) . . ?
C3 C2 H2A 126.4 . . ?
N1 C2 H2A 126.4 . . ?
C2 C3 N2 106.5(8) . . ?
C2 C3 C4 130.3(8) . . ?
N2 C3 C4 123.3(8) . . ?
C3 C4 C5 115.3(6) . . ?
C3 C4 H4A 108.4 . . ?
C5 C4 H4A 108.4 . . ?
C3 C4 H4B 108.4 . . ?
C5 C4 H4B 108.4 . . ?
H4A C4 H4B 107.5 . . ?
N3 C5 C4 109.5(7) . . ?
N3 C5 C6 108.9(6) . . ?
C4 C5 C6 109.3(7) . . ?
N3 C5 H5A 109.7 . . ?
C4 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
O1 C6 O2 126.7(7) . . ?
O1 C6 C5 116.8(7) . . ?
O2 C6 C5 116.5(7) . . ?
C8 N4 C7 109.6(7) . . ?
C8 N4 H4 125.2 . . ?
C7 N4 H4 125.1 . . ?
C8 N5 C9 108.6(7) . . ?
C8 N5 H5 125.8 . . ?
C9 N5 H5 125.6 . . ?
C11 N6 H6A 109.4 . . ?
C11 N6 H6B 109.5 . . ?
H6A N6 H6B 109.5 . . ?
C11 N6 H6C 109.5 . . ?
H6A N6 H6C 109.5 . . ?
H6B N6 H6C 109.5 . . ?
C9 C7 N4 105.7(8) . . ?
C9 C7 H7 127.1 . . ?
N4 C7 H7 127.1 . . ?
N4 C8 N5 108.7(8) . . ?
N4 C8 H8 125.6 . . ?
N5 C8 H8 125.6 . . ?
C7 C9 N5 107.3(7) . . ?
C7 C9 C10 130.1(8) . . ?
N5 C9 C10 122.6(7) . . ?
C9 C10 C11 113.4(7) . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
N6 C11 C12 109.0(7) . . ?
N6 C11 C10 109.8(6) . . ?
C12 C11 C10 109.6(7) . . ?
N6 C11 H11 109.5 . . ?
C12 C11 H11 109.5 . . ?
C10 C11 H11 109.5 . . ?
O4 C12 O3 125.4(8) . . ?
O4 C12 C11 119.0(7) . . ?
O3 C12 C11 115.5(7) . . ?

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
C3 N2 C1 N1 1.8(9) . . . . ?
C2 N1 C1 N2 -2.1(9) . . . . ?
C1 N1 C2 C3 1.6(9) . . . . ?
N1 C2 C3 N2 -0.5(9) . . . . ?
N1 C2 C3 C4 178.9(8) . . . . ?
C1 N2 C3 C2 -0.8(9) . . . . ?
C1 N2 C3 C4 179.8(7) . . . . ?
C2 C3 C4 C5 98.4(11) . . . . ?
N2 C3 C4 C5 -82.3(10) . . . . ?
C3 C4 C5 N3 59.9(9) . . . . ?
C3 C4 C5 C6 179.1(7) . . . . ?
N3 C5 C6 O1 -147.1(8) . . . . ?
C4 C5 C6 O1 93.3(9) . . . . ?
N3 C5 C6 O2 32.1(10) . . . . ?
C4 C5 C6 O2 -87.5(9) . . . . ?
C8 N4 C7 C9 -0.9(10) . . . . ?
C7 N4 C8 N5 1.6(9) . . . . ?
C9 N5 C8 N4 -1.6(9) . . . . ?
N4 C7 C9 N5 0.0(10) . . . . ?
N4 C7 C9 C10 -177.1(9) . . . . ?
C8 N5 C9 C7 1.0(10) . . . . ?
C8 N5 C9 C10 178.3(8) . . . . ?
C7 C9 C10 C11 -131.0(10) . . . . ?
N5 C9 C10 C11 52.3(11) . . . . ?
C9 C10 C11 N6 55.0(9) . . . . ?
C9 C10 C11 C12 174.8(7) . . . . ?
N6 C11 C12 O4 7.5(10) . . . . ?
C10 C11 C12 O4 -112.7(8) . . . . ?
N6 C11 C12 O3 -172.8(6) . . . . ?
C10 C11 C12 O3 67.1(9) . . . . ?

_refine_diff_density_max         1.102
_refine_diff_density_min         -0.740
_refine_diff_density_rms         0.173

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2504992'
loop_
_audit_author_name
_audit_author_address
'SANDRA WALHA'
;University of sfax
Tunisia
;
_audit_update_record             
;
2025-11-23 deposited with the CCDC.	2026-02-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H12 Cl N O2'
_chemical_formula_weight         201.65

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   5.3830(17)
_cell_length_b                   7.045(2)
_cell_length_c                   27.746(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1052.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(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    1.273
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.332
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24476
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0941
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.937
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_full        25.048
_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             1869
_reflns_number_gt                1591
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.644
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0302P)²+0.4921P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.04(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1869
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0868
_refine_ls_wR_factor_gt          0.0815
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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 0.77546(16) 0.89985(13) 0.30628(3) 0.0448(3) Uani 1 1 d . . . . .
O1 O 0.3905(5) 0.6201(4) 0.33633(11) 0.0619(9) Uani 1 1 d . . . . .
H1 H 0.516377 0.685203 0.334409 0.093 Uiso 1 1 calc R U . . .
O2 O 0.6172(4) 0.4093(4) 0.29550(9) 0.0414(6) Uani 1 1 d . . . . .
N10 N 0.2573(6) 0.1513(4) 0.29258(11) 0.0356(7) Uani 1 1 d . . . . .
H10A H 0.401(7) 0.094(6) 0.3018(13) 0.043 Uiso 1 1 d . U . . .
H10B H 0.129(7) 0.065(5) 0.2972(13) 0.043 Uiso 1 1 d . U . . .
H10C H 0.262(8) 0.183(5) 0.2590(14) 0.043 Uiso 1 1 d . U . . .
C1 C 0.4300(6) 0.4543(5) 0.31552(13) 0.0325(8) Uani 1 1 d . . . . .
C2 C 0.2026(6) 0.3290(5) 0.31893(12) 0.0326(8) Uani 1 1 d . . . . .
H2 H 0.067511 0.393444 0.301809 0.039 Uiso 1 1 calc R U . . .
C3 C 0.1135(7) 0.2918(5) 0.37057(13) 0.0383(9) Uani 1 1 d . . . . .
H3A H 0.072845 0.412633 0.385356 0.046 Uiso 1 1 calc R U . . .
H3B H -0.038311 0.217785 0.369081 0.046 Uiso 1 1 calc R U . . .
C4 C 0.2942(8) 0.1902(6) 0.40249(12) 0.0406(10) Uani 1 1 d . . . . .
C5 C 0.2790(12) -0.0023(6) 0.40973(15) 0.0672(14) Uani 1 1 d . . . . .
H5 H 0.155486 -0.071761 0.394291 0.081 Uiso 1 1 calc R U . . .
C6 C 0.4451(16) -0.0939(10) 0.4397(2) 0.104(2) Uani 1 1 d . . . . .
H6 H 0.433254 -0.224210 0.444500 0.125 Uiso 1 1 calc R U . . .
C7 C 0.6288(15) 0.0092(13) 0.4624(2) 0.104(3) Uani 1 1 d . . . . .
H7 H 0.740646 -0.052399 0.482633 0.124 Uiso 1 1 calc R U . . .
C8 C 0.6482(10) 0.1977(12) 0.45573(17) 0.0829(19) Uani 1 1 d . . . . .
H8 H 0.773003 0.265877 0.471128 0.099 Uiso 1 1 calc R U . . .
C9 C 0.4821(8) 0.2893(8) 0.42591(15) 0.0555(12) Uani 1 1 d . . . . .
H9 H 0.495963 0.419702 0.421387 0.067 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
O1 C1 1.320(4) . ?
O1 H1 0.8200 . ?
O2 C1 1.193(4) . ?
N10 C2 1.480(4) . ?
N10 H10A 0.91(4) . ?
N10 H10B 0.93(4) . ?
N10 H10C 0.96(4) . ?
C1 C2 1.512(5) . ?
C2 C3 1.534(5) . ?
C2 H2 0.9800 . ?
C3 C4 1.497(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.374(5) . ?
C4 C9 1.390(6) . ?
C5 C6 1.381(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.380(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.345(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.379(7) . ?
C8 H8 0.9300 . ?
C9 H9 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
C1 O1 H1 109.5 . . ?
C2 N10 H10A 114(2) . . ?
C2 N10 H10B 110(2) . . ?
H10A N10 H10B 108(3) . . ?
C2 N10 H10C 107(2) . . ?
H10A N10 H10C 111(3) . . ?
H10B N10 H10C 108(3) . . ?
O2 C1 O1 125.0(3) . . ?
O2 C1 C2 123.9(3) . . ?
O1 C1 C2 111.0(3) . . ?
N10 C2 C1 107.6(3) . . ?
N10 C2 C3 112.3(3) . . ?
C1 C2 C3 114.3(3) . . ?
N10 C2 H2 107.5 . . ?
C1 C2 H2 107.5 . . ?
C3 C2 H2 107.5 . . ?
C4 C3 C2 115.5(3) . . ?
C4 C3 H3A 108.4 . . ?
C2 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
C2 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
C5 C4 C9 118.1(5) . . ?
C5 C4 C3 121.3(4) . . ?
C9 C4 C3 120.6(4) . . ?
C4 C5 C6 120.7(6) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 119.6(6) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C8 C7 C6 120.8(6) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 119.7(6) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C4 121.1(5) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 H9 119.4 . . ?

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
O2 C1 C2 N10 -1.3(5) . . . . ?
O1 C1 C2 N10 176.9(3) . . . . ?
O2 C1 C2 C3 124.1(4) . . . . ?
O1 C1 C2 C3 -57.7(4) . . . . ?
N10 C2 C3 C4 61.0(4) . . . . ?
C1 C2 C3 C4 -61.9(4) . . . . ?
C2 C3 C4 C5 -97.5(5) . . . . ?
C2 C3 C4 C9 82.9(4) . . . . ?
C9 C4 C5 C6 0.4(7) . . . . ?
C3 C4 C5 C6 -179.3(4) . . . . ?
C4 C5 C6 C7 -0.2(9) . . . . ?
C5 C6 C7 C8 -0.1(10) . . . . ?
C6 C7 C8 C9 0.2(10) . . . . ?
C7 C8 C9 C4 -0.1(8) . . . . ?
C5 C4 C9 C8 -0.3(6) . . . . ?
C3 C4 C9 C8 179.4(4) . . . . ?

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
_geom_hbond_publ_flag
O1 H1 Cl1 0.82 2.20 2.979(3) 158.6 . yes
N10 H10A Cl1 0.91(4) 2.44(4) 3.326(4) 165(3) 1_545 yes
N10 H10B Cl1 0.93(4) 2.24(4) 3.164(3) 170(3) 1_445 yes
N10 H10C Cl1 0.96(4) 2.38(4) 3.259(3) 153(3) 3_645 yes
N10 H10C O2 0.96(4) 2.53(3) 3.055(4) 114(2) 3_645 yes
C2 H2 O2 0.98 2.43 3.267(4) 142.7 1_455 yes

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.043

