# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_2
_database_code_depnum_ccdc_archive 'CCDC 2300002'
loop_
_audit_author_name
_audit_author_address
Lily
;Fujian Institute of Research on the Structure of Matter
China
;
_audit_update_record             
;
2023-10-09 deposited with the CCDC.	2023-11-27 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            'C5 H6.16 Cl2.84 I N2 O2'
_chemical_formula_weight         353.86

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                   7.5387(5)
_cell_length_b                   8.2803(5)
_cell_length_c                   8.4979(5)
_cell_angle_alpha                83.344(5)
_cell_angle_beta                 89.699(5)
_cell_angle_gamma                70.311(6)
_cell_volume                     495.76(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4545
_cell_measurement_theta_min      4.0650
_cell_measurement_theta_max      29.2030

_exptl_crystal_description       Clubbed
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.370
_exptl_crystal_F_000             335
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    3.962
_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      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8792
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.350
_diffrn_reflns_theta_max         26.357
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2030
_reflns_number_gt                1844
_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)+(0.0224P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2030
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0536
_refine_ls_wR_factor_gt          0.0512
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.26013(3) 0.97455(3) 0.01367(2) 0.02131(9) Uani 1 1 d . . . . .
Cl1 Cl 0.23015(14) 0.97475(13) -0.27878(9) 0.0375(2) Uani 1 1 d . . . . .
Cl2 Cl 0.27189(14) 1.01489(12) 0.29914(10) 0.0361(2) Uani 1 1 d . . . . .
Cl3 Cl 0.1118(2) 0.55050(19) 0.82082(13) 0.0511(5) Uani 0.840(4) 1 d . . . . .
N1 N 0.1904(4) 0.6306(4) 0.3639(3) 0.0296(7) Uani 1 1 d . . . . .
H1 H 0.150725 0.714200 0.288468 0.036 Uiso 1 1 calc R U . . .
N2 N 0.3610(5) 0.4623(4) 0.1800(3) 0.0408(8) Uani 1 1 d . . . . .
H2A H 0.317416 0.548456 0.107384 0.049 Uiso 1 1 calc R U . . .
H2B H 0.437480 0.365598 0.156203 0.049 Uiso 1 1 calc R U . . .
C1 C 0.1283(5) 0.6599(5) 0.5120(4) 0.0330(8) Uani 1 1 d . . . . .
H1A H 0.044565 0.767145 0.530435 0.040 Uiso 1 1 calc R U . . .
C2 C 0.1912(6) 0.5291(5) 0.6323(4) 0.0357(9) Uani 1 1 d . . . . .
C3 C 0.3201(6) 0.3702(5) 0.6019(4) 0.0368(9) Uani 1 1 d . . . . .
H3 H 0.366051 0.281675 0.684751 0.044 Uiso 1 1 calc R U . . .
C4 C 0.3783(5) 0.3443(5) 0.4543(4) 0.0337(9) Uani 1 1 d . . . . .
H4 H 0.463349 0.237909 0.435172 0.040 Uiso 1 1 calc R U . . .
C5 C 0.3102(5) 0.4785(4) 0.3284(4) 0.0281(8) Uani 1 1 d . . . . .
O1 O 0.4949(3) 0.8241(3) 0.0228(3) 0.0295(5) Uani 1 1 d . . . . .
O2 O 0.1330(3) 0.8276(3) 0.0554(2) 0.0287(5) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.01836(14) 0.02059(13) 0.02347(13) -0.00201(8) 0.00014(8) -0.00483(9)
Cl1 0.0362(6) 0.0501(6) 0.0265(4) -0.0054(4) 0.0016(4) -0.0147(5)
Cl2 0.0377(6) 0.0422(6) 0.0295(4) -0.0115(4) 0.0008(4) -0.0124(4)
Cl3 0.0515(9) 0.0706(10) 0.0299(7) -0.0132(5) 0.0033(5) -0.0169(7)
N1 0.0342(19) 0.0240(16) 0.0288(15) 0.0005(12) -0.0039(13) -0.0085(14)
N2 0.048(2) 0.0358(19) 0.0339(18) -0.0092(14) 0.0064(15) -0.0071(17)
C1 0.030(2) 0.033(2) 0.035(2) -0.0115(15) -0.0005(15) -0.0054(17)
C2 0.031(2) 0.048(2) 0.0302(19) -0.0060(16) -0.0005(15) -0.0162(19)
C3 0.036(2) 0.038(2) 0.037(2) 0.0077(16) -0.0093(17) -0.0160(19)
C4 0.034(2) 0.023(2) 0.041(2) -0.0013(15) -0.0047(16) -0.0067(17)
C5 0.028(2) 0.0254(19) 0.0341(19) -0.0054(14) -0.0017(15) -0.0122(16)
O1 0.0181(13) 0.0298(14) 0.0357(13) -0.0057(10) 0.0007(10) -0.0013(11)
O2 0.0281(14) 0.0280(13) 0.0321(12) 0.0010(10) -0.0014(10) -0.0136(11)

_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 O1 1.784(2) . ?
I1 O2 1.791(2) . ?
I1 Cl2 2.4929(8) . ?
I1 Cl1 2.4963(8) . ?
Cl3 C2 1.715(4) . ?
N1 C5 1.346(4) . ?
N1 C1 1.360(4) . ?
N1 H1 0.8600 . ?
N2 C5 1.325(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C1 C2 1.359(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.399(5) . ?
C3 C4 1.344(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.410(5) . ?
C4 H4 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
O1 I1 O2 99.63(11) . . ?
O1 I1 Cl2 93.01(7) . . ?
O2 I1 Cl2 91.48(7) . . ?
O1 I1 Cl1 92.11(7) . . ?
O2 I1 Cl1 92.72(7) . . ?
Cl2 I1 Cl1 172.75(3) . . ?
C5 N1 C1 123.9(3) . . ?
C5 N1 H1 118.0 . . ?
C1 N1 H1 118.0 . . ?
C5 N2 H2A 120.0 . . ?
C5 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C2 C1 N1 118.5(3) . . ?
C2 C1 H1A 120.7 . . ?
N1 C1 H1A 120.7 . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 Cl3 121.9(3) . . ?
C3 C2 Cl3 118.5(3) . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N2 C5 N1 119.4(3) . . ?
N2 C5 C4 123.3(3) . . ?
N1 C5 C4 117.3(3) . . ?

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 O2 0.86 2.08 2.875(3) 154.3 .
N2 H2A O2 0.86 2.25 2.999(4) 145.2 .
N2 H2B O1 0.86 2.25 2.994(4) 145.3 2_665

_refine_diff_density_max         0.732
_refine_diff_density_min         -0.775
_refine_diff_density_rms         0.116

_shelx_res_file                  
;
TITL 2_a.res in P-1
    2.res
    created by SHELXL-2016/6 at 10:47:40 on 25-Aug-2023
REM Old TITL 2 in P1
REM SHELXT solution in P-1
REM R1 0.060, Rweak 0.009, Alpha 0.038, Orientation as input
REM Formula found by SHELXT: C6 N O2 Cl2.84 I
CELL 0.71073 7.5387 8.2803 8.4979 83.344 89.699 70.311
ZERR 2 0.0005 0.0005 0.0005 0.005 0.005 0.006
LATT 1
SFAC C H Cl I N O
UNIT 10 12.32 5.68 2 4 4

L.S. 4 0 0
PLAN  2
TEMP 21
HTAB N1 O2
list 4
MORE -1
BOND $H
fmap 2 53
htab N2 O2
eqiv $1 -x+1, -y+1, -z
htab  N2 O1_$1
acta
REM <olex2.extras>
REM <HklSrc "%.\\2.hkl">
REM </olex2.extras>
WGHT    0.022400
FVAR       0.56465
I1    4    0.260127    0.974555    0.013665    11.00000    0.01836    0.02059 =
         0.02347   -0.00201    0.00014   -0.00483
CL1   3    0.230153    0.974750   -0.278778    11.00000    0.03624    0.05007 =
         0.02649   -0.00544    0.00163   -0.01467
CL2   3    0.271888    1.014892    0.299143    11.00000    0.03766    0.04223 =
         0.02947   -0.01150    0.00076   -0.01244
CL3   3    0.111775    0.550500    0.820817     0.84036    0.05153    0.07064 =
         0.02994   -0.01324    0.00327   -0.01688
N1    5    0.190383    0.630584    0.363931    11.00000    0.03416    0.02401 =
         0.02885    0.00052   -0.00389   -0.00849
AFIX  43
H1    2    0.150725    0.714200    0.288468    11.00000   -1.20000
AFIX   0
N2    5    0.360974    0.462292    0.179972    11.00000    0.04829    0.03582 =
         0.03386   -0.00918    0.00635   -0.00705
AFIX  93
H2A   2    0.317416    0.548456    0.107384    11.00000   -1.20000
H2B   2    0.437480    0.365598    0.156203    11.00000   -1.20000
AFIX   0
C1    1    0.128278    0.659921    0.511966    11.00000    0.02954    0.03263 =
         0.03478   -0.01145   -0.00055   -0.00540
AFIX  43
H1A   2    0.044565    0.767145    0.530435    11.00000   -1.20000
AFIX   0
C2    1    0.191217    0.529135    0.632306    11.00000    0.03133    0.04803 =
         0.03024   -0.00605   -0.00049   -0.01623
C3    1    0.320131    0.370245    0.601927    11.00000    0.03569    0.03787 =
         0.03666    0.00766   -0.00934   -0.01603
AFIX  43
H3    2    0.366051    0.281675    0.684751    11.00000   -1.20000
AFIX   0
C4    1    0.378295    0.344276    0.454316    11.00000    0.03398    0.02315 =
         0.04111   -0.00134   -0.00466   -0.00671
AFIX  43
H4    2    0.463349    0.237909    0.435172    11.00000   -1.20000
AFIX   0
C5    1    0.310205    0.478517    0.328444    11.00000    0.02768    0.02538 =
         0.03413   -0.00541   -0.00171   -0.01224
O1    6    0.494910    0.824095    0.022821    11.00000    0.01811    0.02983 =
         0.03566   -0.00574    0.00072   -0.00131
O2    6    0.133047    0.827589    0.055419    11.00000    0.02806    0.02802 =
         0.03206    0.00101   -0.00143   -0.01358

HKLF 4




REM  2_a.res in P-1
REM R1 =  0.0239 for    1844 Fo > 4sig(Fo)  and  0.0290 for all    2030 data
REM    119 parameters refined using      0 restraints

END

WGHT      0.0224      0.0000

REM Highest difference peak  0.732,  deepest hole -0.775,  1-sigma level  0.116
Q1    1   0.1455  0.4399  0.8393  11.00000  0.05    0.73
Q2    1   0.2058  0.8800  0.0492  11.00000  0.05    0.56
;
_shelx_res_checksum              27467
