# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_mix6
_database_code_depnum_ccdc_archive 'CCDC 2004829'
loop_
_audit_author_name
_audit_author_address
'Kyrill Yu. Suponitsky'
;A N Nesmeyanov Institute of Organoelement Compounds, Moscow
Russia
;
_audit_update_record             
;
2020-05-20 deposited with the CCDC.	2021-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H9 N O, Cl I'
_chemical_formula_sum            'C3 H9 Cl I N O'
_chemical_formula_weight         237.46

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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   9.60490(10)
_cell_length_b                   7.63670(10)
_cell_length_c                   9.63370(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     706.629(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4950
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      29.96

_exptl_crystal_description       prizm
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.232
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    4.812
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.401
_exptl_absorpt_correction_T_max  0.486
_exptl_absorpt_process_details   'SADABS-2014/5 (Bruker,2014/5)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17016
_diffrn_reflns_av_unetI/netI     0.0100
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.012
_diffrn_reflns_theta_max         30.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             1187
_reflns_number_gt                1182
_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       'APEX (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2015)'
_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)+(0.0125P)²+0.6885P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1187
_refine_ls_number_parameters     59
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0140
_refine_ls_R_factor_gt           0.0140
_refine_ls_wR_factor_ref         0.0343
_refine_ls_wR_factor_gt          0.0343
_refine_ls_goodness_of_fit_ref   1.281
_refine_ls_restrained_S_all      1.281
_refine_ls_shift/su_max          0.001
_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 0.54074(2) 0.2500 0.57977(2) 0.00871(5) Uani 1 2 d S T P . .
Cl1 Cl 0.48195(5) 0.2500 0.83987(5) 0.01255(9) Uani 1 2 d S T P . .
O1 O 0.56309(16) 0.2500 0.35360(16) 0.0120(3) Uani 1 2 d S T P . .
N1 N 0.69803(18) 0.2500 0.29296(18) 0.0101(3) Uani 1 2 d S T P . .
C1 C 0.6714(3) 0.2500 0.1405(2) 0.0182(4) Uani 1 2 d S T P . .
C2 C 0.77701(16) 0.0892(2) 0.33305(17) 0.0149(3) Uani 1 1 d . . . . .
H2A H 0.865(2) 0.090(3) 0.280(2) 0.020(6) Uiso 1 1 d . . . . .
H2B H 0.796(3) 0.094(3) 0.433(2) 0.022(6) Uiso 1 1 d . . . . .
H2C H 0.722(2) -0.007(3) 0.306(3) 0.024(6) Uiso 1 1 d . . . . .
H1A H 0.618(3) 0.153(3) 0.120(2) 0.025(6) Uiso 1 1 d . . . . .
H1B H 0.757(4) 0.2500 0.096(3) 0.018(8) Uiso 1 2 d S . P . .

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 0.00846(7) 0.01026(7) 0.00742(7) 0.000 0.00030(4) 0.000
Cl1 0.0148(2) 0.0151(2) 0.0078(2) 0.000 0.00124(16) 0.000
O1 0.0056(6) 0.0214(7) 0.0089(6) 0.000 0.0012(5) 0.000
N1 0.0076(7) 0.0136(7) 0.0092(7) 0.000 0.0012(5) 0.000
C1 0.0163(10) 0.0301(12) 0.0083(9) 0.000 0.0014(7) 0.000
C2 0.0139(6) 0.0127(6) 0.0182(7) 0.0007(5) 0.0017(5) 0.0023(5)

_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 2.1895(15) . ?
I1 Cl1 2.5685(5) . ?
O1 N1 1.422(2) . ?
N1 C1 1.491(3) . ?
N1 C2 1.4943(18) 7_565 ?
N1 C2 1.4943(18) . ?
C1 H1A 0.93(3) . ?
C1 H1B 0.93(3) . ?
C2 H2A 0.99(2) . ?
C2 H2B 0.98(2) . ?
C2 H2C 0.94(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
O1 I1 Cl1 172.93(4) . . ?
N1 O1 I1 119.89(11) . . ?
O1 N1 C1 104.37(16) . . ?
O1 N1 C2 110.89(10) . 7_565 ?
C1 N1 C2 109.99(11) . 7_565 ?
O1 N1 C2 110.89(10) . . ?
C1 N1 C2 109.99(11) . . ?
C2 N1 C2 110.55(17) 7_565 . ?
N1 C1 H1A 108.0(15) . . ?
N1 C1 H1B 107(2) . . ?
H1A C1 H1B 113.3(18) . . ?
N1 C2 H2A 107.1(14) . . ?
N1 C2 H2B 108.3(15) . . ?
H2A C2 H2B 111(2) . . ?
N1 C2 H2C 106.3(15) . . ?
H2A C2 H2C 110(2) . . ?
H2B C2 H2C 114(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
I1 O1 N1 C1 180.000(0) . . . . ?
I1 O1 N1 C2 -61.61(11) . . . 7_565 ?
I1 O1 N1 C2 61.61(11) . . . . ?

_refine_diff_density_max         0.508
_refine_diff_density_min         -0.876
_refine_diff_density_rms         0.100

_shelxl_version_number           2014/6

_shelx_res_file                  
;
TITL mix6 in Pnma
CELL 0.71073   9.6049   7.6367   9.6337  90.000  90.000  90.000
ZERR    4.00   0.0001   0.0001   0.0001   0.000   0.000   0.000
LATT  1
SYMM 0.5-X, -Y, 0.5+Z
SYMM -X, 0.5+Y, -Z
SYMM 0.5+X, 0.5-Y, 0.5-Z
SFAC C H N O CL I
UNIT 12 36 4 4 4 4
TEMP -173.0

ACTA
CONF
HTAB

OMIT -4 62

L.S. 4
BOND $H
FMAP 2
PLAN 10

OMIT     0   2   0
OMIT     1   0   1
OMIT     0   1   1
OMIT     2   2   0
OMIT     2   0   0
OMIT     0   4   0
OMIT     0   1   3
OMIT     1   1   4

WGHT    0.012500    0.688500
FVAR       0.40673
I1    6    0.540736    0.250000    0.579775    10.50000    0.00846    0.01026 =
         0.00742    0.00000    0.00030    0.00000
CL1   5    0.481948    0.250000    0.839869    10.50000    0.01483    0.01505 =
         0.00779    0.00000    0.00124    0.00000
O1    4    0.563088    0.250000    0.353600    10.50000    0.00564    0.02139 =
         0.00886    0.00000    0.00123    0.00000
N1    3    0.698033    0.250000    0.292964    10.50000    0.00765    0.01360 =
         0.00917    0.00000    0.00120    0.00000
C1    1    0.671374    0.250000    0.140474    10.50000    0.01628    0.03006 =
         0.00834    0.00000    0.00139    0.00000
C2    1    0.777011    0.089178    0.333052    11.00000    0.01386    0.01265 =
         0.01824    0.00071    0.00174    0.00229
H2A   2    0.864928    0.089904    0.279562    11.00000    0.01986
H2B   2    0.795797    0.094457    0.433116    11.00000    0.02163
H2C   2    0.721733   -0.006904    0.305669    11.00000    0.02374
H1A   2    0.617767    0.152697    0.119698    11.00000    0.02533
H1B   2    0.757469    0.250000    0.096344    10.50000    0.01767
HKLF 4

REM  mix6 in Pnma
REM R1 =  0.0140 for    1182 Fo > 4sig(Fo)  and  0.0140 for all    1187 data
REM     59 parameters refined using      0 restraints

END

WGHT      0.0127      0.6856

REM Instructions for potential hydrogen bonds
EQIV $1 x+1/2, y, -z+1/2
HTAB C2 O1_$1
EQIV $2 -x+1, -y, -z+1
HTAB C2 I1_$2
HTAB C1 I1_$1

REM Highest difference peak  0.508,  deepest hole -0.876,  1-sigma level  0.100
Q1    1   0.7041  0.2500  0.5837  10.50000  0.05    0.51
Q2    1   0.5294  0.2500  0.8600  10.50000  0.05    0.46
Q3    1   0.4802  0.2500  0.1607  10.50000  0.05    0.46
Q4    1   0.4615  0.2500  0.8696  10.50000  0.05    0.42
Q5    1   0.6210  0.2500  0.5879  10.50000  0.05    0.39
Q6    1   0.5519  0.2500  0.0486  10.50000  0.05    0.38
Q7    1   0.4943  0.2053  0.8239  11.00000  0.05    0.37
Q8    1   0.6800  0.2500  0.2251  10.50000  0.05    0.36
Q9    1   0.3610  0.2500  0.9057  10.50000  0.05    0.29
Q10   1   0.7388  0.1779  0.3093  11.00000  0.05    0.29
;
_shelx_res_checksum              62866
