# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_zf231125-1-300k_auto
_database_code_depnum_ccdc_archive 'CCDC 2321879'
loop_
_audit_author_name
_audit_author_address
'Yanran Weng '
;Nanchang University
China
;
_audit_update_record             
;
2023-12-26 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;
_audit_creation_date             2023-12-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl1 O4, C4 H12 N1 O3'
_chemical_formula_sum            'C4 H12 Cl N O7'
_chemical_formula_weight         221.60
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Cl'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   8.0483(2)
_cell_length_b                   8.0483(2)
_cell_length_c                   23.8037(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1335.31(7)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    1214
_cell_measurement_temperature    299.98(10)
_cell_measurement_theta_max      74.1390
_cell_measurement_theta_min      5.5570
_shelx_estimated_absorpt_T_max   0.690
_shelx_estimated_absorpt_T_min   0.380
_exptl_absorpt_coefficient_mu    4.003
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38407
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0105
_diffrn_reflns_av_unetI/netI     0.0085
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            1186
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.330
_diffrn_reflns_theta_min         5.576
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     86.00 114.00   0.50    0.50    --  108.36 125.00 120.00   56
  2  ω    131.00 178.00   0.50    0.50    --  108.36 125.00 120.00   94
  3  ω     35.00  92.00   0.50    0.50    --  108.36 -77.00 -90.00  114
  4  ω     47.00  72.00   0.50    0.50    --  108.36 -61.00 -60.00   50
  5  ω    -32.00  12.00   0.50    1.00    --   45.20 -19.00-180.00   88
  6  ω    -23.00  28.00   0.50    1.00    --   45.20 -18.00  48.00  102
  7  ω    -18.00   7.00   0.50    1.00    --  -45.20  18.00-143.00   50
  8  ω    -67.00 -28.00   0.50    0.50    -- -102.00  61.00 138.00   78
  9  ω   -174.00 -96.00   0.50    0.50    -- -102.00 -37.00   4.00  156
 10  ω   -167.00-107.00   0.50    0.50    -- -102.00-107.00 -82.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0786183000
_diffrn_orient_matrix_UB_12      -0.0522211000
_diffrn_orient_matrix_UB_13      0.0519744000
_diffrn_orient_matrix_UB_21      0.0217157000
_diffrn_orient_matrix_UB_22      -0.1490111000
_diffrn_orient_matrix_UB_23      -0.0350115000
_diffrn_orient_matrix_UB_31      0.2054552000
_diffrn_orient_matrix_UB_32      0.1546306000
_diffrn_orient_matrix_UB_33      -0.0161773000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                582
_reflns_number_total             584
_reflns_odcompleteness_completeness 98.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.023(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     43
_refine_ls_number_reflns         584
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0547
_refine_ls_restrained_S_all      1.065
_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)+(0.0826P)²+5.7118P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1439
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: H1C(0.33333) H1B(0.33333) H1A(0.33333)
3.a Secondary CH2 refined with riding coordinates:
 C005(H00A,H00B)
3.b Idealised Me refined as rotating group:
 N1(H1C,H1B,H1A)
3.c Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_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
Cl01 Cl 0.666667 0.333333 0.48207(4) 0.0278(6) Uani 1 3 d S T P . .
O002 O 0.3584(3) 0.3225(3) 0.71264(7) 0.0284(6) Uani 1 1 d . . . . .
H002 H 0.359160 0.407595 0.731783 0.043 Uiso 1 1 calc R U . . .
N1 N 0.666667 0.333333 0.65822(14) 0.0213(9) Uani 1 3 d S T P . .
H1C H 0.657773 0.432860 0.645753 0.026 Uiso 0.3333 1 calc R U P A -1
H1B H 0.567140 0.224913 0.645753 0.026 Uiso 0.3333 1 calc R U P A -1
H1A H 0.775087 0.342227 0.645753 0.026 Uiso 0.3333 1 calc R U P A -1
C004 C 0.666667 0.333333 0.72164(17) 0.0209(9) Uani 1 3 d S T P . .
C005 C 0.4589(4) 0.2439(4) 0.74148(11) 0.0268(7) Uani 1 1 d . . . . .
H00A H 0.393777 0.106470 0.735269 0.032 Uiso 1 1 calc R U . . .
H00B H 0.457148 0.265777 0.781498 0.032 Uiso 1 1 calc R U . . .
O4 O 0.8055(5) 0.2884(6) 0.46321(17) 0.0925(14) Uani 1 1 d . . . . .
O5 O 0.666667 0.333333 0.5408(2) 0.0834(19) Uani 1 3 d S T 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
Cl01 0.0296(6) 0.0296(6) 0.0240(7) 0.000 0.000 0.0148(3)
O002 0.0264(10) 0.0295(11) 0.0327(11) -0.0055(7) -0.0020(7) 0.0165(8)
N1 0.0223(12) 0.0223(12) 0.0194(18) 0.000 0.000 0.0111(6)
C004 0.0233(13) 0.0233(13) 0.0160(19) 0.000 0.000 0.0116(7)
C005 0.0256(14) 0.0301(14) 0.0246(13) 0.0028(10) 0.0032(9) 0.0139(11)
O4 0.074(2) 0.112(3) 0.111(3) -0.033(2) 0.0123(19) 0.061(2)
O5 0.112(3) 0.112(3) 0.026(2) 0.000 0.000 0.0560(15)

_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
Cl01 O4 1.409(3) . ?
Cl01 O4 1.409(3) 2_655 ?
Cl01 O4 1.409(3) 3_665 ?
Cl01 O5 1.399(5) . ?
O002 H002 0.8200 . ?
O002 C005 1.427(3) . ?
N1 H1C 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1A 0.8900 . ?
N1 C004 1.510(5) . ?
C004 C005 1.528(3) 3_665 ?
C004 C005 1.528(3) . ?
C004 C005 1.528(3) 2_655 ?
C005 H00A 0.9700 . ?
C005 H00B 0.9700 . ?

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
O4 Cl01 O4 110.35(17) . 3_665 ?
O4 Cl01 O4 110.35(17) 3_665 2_655 ?
O4 Cl01 O4 110.35(17) . 2_655 ?
O5 Cl01 O4 108.57(17) . 2_655 ?
O5 Cl01 O4 108.58(17) . . ?
O5 Cl01 O4 108.57(17) . 3_665 ?
C005 O002 H002 109.5 . . ?
H1C N1 H1B 109.5 . . ?
H1C N1 H1A 109.5 . . ?
H1B N1 H1A 109.5 . . ?
C004 N1 H1C 109.5 . . ?
C004 N1 H1B 109.5 . . ?
C004 N1 H1A 109.5 . . ?
N1 C004 C005 108.01(17) . . ?
N1 C004 C005 108.01(17) . 2_655 ?
N1 C004 C005 108.01(17) . 3_665 ?
C005 C004 C005 110.90(16) 2_655 3_665 ?
C005 C004 C005 110.90(16) 3_665 . ?
C005 C004 C005 110.90(16) 2_655 . ?
O002 C005 C004 111.8(2) . . ?
O002 C005 H00A 109.2 . . ?
O002 C005 H00B 109.2 . . ?
C004 C005 H00A 109.2 . . ?
C004 C005 H00B 109.2 . . ?
H00A C005 H00B 107.9 . . ?

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
N1 C004 C005 O002 -47.5(2) . . . . ?
C005 C004 C005 O002 70.6(4) 3_665 . . . ?
C005 C004 C005 O002 -165.7(2) 2_655 . . . ?

_shelx_res_file                  
;
TITL zf231125-1-300k_auto_a.res in R-3
    zf231125-1-300k_auto.res
    created by SHELXL-2018/3 at 20:16:30 on 11-Dec-2023
REM Old TITL ZF231125-1-300K_auto in R-3
REM SHELXT solution in R-3: R1 0.171, Rweak 0.014, Alpha 0.039
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Formula found by SHELXT: C8 O4 Cl
CELL 1.54184 8.0483 8.0483 23.8037 90 90 120
ZERR 6 0.0002 0.0002 0.0005 0 0 0
LATT 3
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SFAC C H Cl N O
UNIT 24 72 6 6 42

L.S. 4 0 0
PLAN  5
SIZE 0.1 0.2 0.3
TEMP 27
CONF
list 4
MORE -1
fmap 2 53
acta
BOND $H
REM <olex2.extras>
REM <HklSrc "%.\\ZF231125-1-300K_auto.hkl">
REM </olex2.extras>

WGHT    0.082600    5.711800
EXTI    0.023204
FVAR       0.87050
CL01  3    0.666667    0.333333    0.482068    10.33333    0.02964    0.02964 =
         0.02400    0.00000    0.00000    0.01482
O002  5    0.358409    0.322524    0.712636    11.00000    0.02639    0.02952 =
         0.03271   -0.00546   -0.00204    0.01655
AFIX 147
H002  2    0.359160    0.407595    0.731783    11.00000   -1.50000
AFIX   0
N1    4    0.666667    0.333333    0.658216    10.33333    0.02229    0.02229 =
         0.01942    0.00000    0.00000    0.01115
PART -1
AFIX 137
H1C   2    0.657773    0.432860    0.645753    10.33333   -1.20000
H1B   2    0.567140    0.224913    0.645753    10.33333   -1.20000
H1A   2    0.775087    0.342227    0.645753    10.33333   -1.20000
AFIX   0
PART 0
C004  1    0.666667    0.333333    0.721637    10.33333    0.02328    0.02328 =
         0.01602    0.00000    0.00000    0.01164
C005  1    0.458866    0.243947    0.741480    11.00000    0.02561    0.03010 =
         0.02459    0.00276    0.00316    0.01394
AFIX  23
H00A  2    0.393777    0.106470    0.735269    11.00000   -1.20000
H00B  2    0.457148    0.265777    0.781498    11.00000   -1.20000
AFIX   0

O4    5    0.805508    0.288390    0.463213    11.00000    0.07449    0.11171 =
         0.11094   -0.03318    0.01227    0.06137
O5    5    0.666667    0.333333    0.540837    10.33333    0.11192    0.11192 =
         0.02636    0.00000    0.00000    0.05596
HKLF 4




REM  zf231125-1-300k_auto_a.res in R-3
REM wR2 = 0.1439, GooF = S = 1.065, Restrained GooF = 1.065 for all data
REM R1 = 0.0547 for 582 Fo > 4sig(Fo) and 0.0548 for all 584 data
REM 43 parameters refined using 0 restraints

END

WGHT      0.0826      5.7117

REM Highest difference peak  0.478,  deepest hole -0.723,  1-sigma level  0.083
Q1    1   0.7757  0.3408  0.4306  11.00000  0.05    0.48
Q2    1   0.8294  0.4136  0.4687  11.00000  0.05    0.31
Q3    1   0.5568  0.2692  0.7333  11.00000  0.05    0.30
Q4    1   0.7291  0.2499  0.4792  11.00000  0.05    0.30
Q5    1   0.7575  0.2890  0.4872  11.00000  0.05    0.26
;
_shelx_res_checksum              78193
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.509
_oxdiff_exptl_absorpt_empirical_full_min 0.626
