# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 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_393_pm-3m
_database_code_depnum_ccdc_archive 'CCDC 2234257'
loop_
_audit_author_name
_audit_author_address
'Wei-Xiong Zhang'
;SYSU
China
;
_audit_update_record             
;
2023-01-04 deposited with the CCDC.	2023-03-10 downloaded from the CCDC.
;
_audit_creation_date             2022-10-24
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2021.12.21 svn.raa29eb21 for OlexSys, GUI svn.r6440)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H20 Cl3 N3 O12'
_chemical_formula_sum            'C7 H20 Cl3 N3 O12'
_chemical_formula_weight         444.61
_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 0.0181 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      cubic
_space_group_IT_number           221
_space_group_name_H-M_alt        'P m -3 m'
_space_group_name_Hall           '-P 4 2 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z'
'x, -y, -z'
'z, x, y'
'z, -x, -y'
'-z, -x, y'
'-z, x, -y'
'y, z, x'
'-y, z, -x'
'y, -z, -x'
'-y, -z, x'
'y, x, -z'
'-y, -x, -z'
'y, -x, z'
'-y, x, z'
'x, z, -y'
'-x, z, y'
'-x, -z, -y'
'x, -z, y'
'z, y, -x'
'z, -y, x'
'-z, y, x'
'-z, -y, -x'
'-x, -y, -z'
'x, y, -z'
'x, -y, z'
'-x, y, z'
'-z, -x, -y'
'-z, x, y'
'z, x, -y'
'z, -x, y'
'-y, -z, -x'
'y, -z, x'
'-y, z, x'
'y, z, -x'
'-y, -x, z'
'y, x, z'
'-y, x, -z'
'y, -x, -z'
'-x, -z, y'
'x, -z, -y'
'x, z, y'
'-x, z, -y'
'-z, -y, x'
'-z, y, -x'
'z, -y, -x'
'z, y, x'

_cell_length_a                   7.5679(4)
_cell_length_b                   7.5679(4)
_cell_length_c                   7.5679(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     433.44(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    220
_cell_measurement_temperature    392.99(10)
_cell_measurement_theta_max      68.8200
_cell_measurement_theta_min      5.8820
_shelx_estimated_absorpt_T_max   0.496
_shelx_estimated_absorpt_T_min   0.410
_exptl_absorpt_coefficient_mu    5.429
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.40t (Rigaku Oxford Diffraction, 2015)
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    1.703
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             230
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0090
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            357
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.852
_diffrn_reflns_theta_min         5.847
_diffrn_ambient_temperature      393.00
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     19.00  81.00   1.00    5.00    --   41.14 -99.00-180.00   62
  2  ω     53.00 131.00   1.00   20.00    --  105.29  15.00  90.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                112
_reflns_number_total             116
_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 1.171.38.40t (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.40t (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.40t (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     46
_refine_ls_number_reflns         116
_refine_ls_number_restraints     238
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0598
_refine_ls_restrained_S_all      0.527
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1688P)²+0.0500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1741
_refine_ls_wR_factor_ref         0.1768
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C7-C3
 1.55 with sigma of 0.02
 C6-C4 = C5-C2
 1.56 with sigma of 0.02
 N2-C7 = N2-C5 = N1-C4
 1.48 with sigma of 0.02
 N2-C6 = N1-C3
 1.47 with sigma of 0.02
 N1-C2
 1.49 with sigma of 0.02
 N1-C1
 1.48 with sigma of 0.02
 N2-C3 = N2-C4
 2.48 with sigma of 0.04
 N2-C2 = C7-N1 = N1-C6 = N1-C5
 2.49 with sigma of 0.04
 C7-C4 \\sim C3-C6 \\sim C4-C5 \\sim C6-C2 \\sim C7-C2 \\sim C3-C5
 with sigma of 0.05
 C7-C3 \\sim C6-C4 \\sim C5-C2
 with sigma of 0.02
 C7-C6 \\sim C6-C5 \\sim C7-C5 \\sim C3-C4 \\sim C3-C2 \\sim C4-C2
 with sigma of 0.04
 N2-C7 \\sim N2-C6 \\sim N2-C5 \\sim N1-C3 \\sim N1-C4 \\sim N1-C2
 with sigma of 0.02
 C1-C3 \\sim C1-C4 \\sim C1-C2
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
N1 \\sim N2 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(C3) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(N1)
\\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms
of 0.04
Uanis(C6) = Uanis(N2) = Uanis(C7) = Uanis(C5) = Uanis(C3) = Uanis(C4) =
Uanis(C2) = Uanis(N1) = Uanis(C1)
4. Rigid body (RIGU) restrains
 N1, N2, C2, C3, C4, C5, C6, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: O1(0.25) N1(0.02083) N2(0.02083) H2(0.02083) C1(0.02083)
 H1A(0.02083) H1B(0.02083) H1C(0.02083) C2(0.02083) H2A(0.02083) H2B(0.02083)
 C3(0.02083) H3A(0.02083) H3B(0.02083) C4(0.02083) H4A(0.02083) H4B(0.02083)
 C5(0.02083) H5A(0.02083) H5B(0.02083) C6(0.02083) H6A(0.02083) H6B(0.02083)
 C7(0.02083) H7A(0.02083) H7B(0.02083) H3C(0.02083) H3D(0.02083) H3E(0.02083)
 H3F(0.02083)
6.a Riding coordinates:
 C1(H1A,H1B,H1C), N3(H3C,H3D,H3E), N3(H3F)
6.b Ternary CH refined with riding coordinates:
 N2(H2)
6.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Cl1 Cl 0.000000 1.000000 0.500000 0.1085(16) Uani 1 16 d S T P . .
O1 O -0.033(3) 0.8506(13) 0.6097(9) 0.136(6) Uani 0.25 1 d . . P A -1
N1 N 0.542(4) 0.443(4) 0.419(4) 0.076(6) Uani 0.0208 1 d D U P B -1
N2 N 0.409(4) 0.643(6) 0.654(7) 0.076(6) Uani 0.0208 1 d D U P B -1
H2 H 0.357581 0.720583 0.743911 0.091 Uiso 0.0208 1 calc R U P B -1
C1 C 0.619(6) 0.326(7) 0.281(6) 0.076(6) Uani 0.0208 1 d D U P B -1
H1A H 0.614269 0.384284 0.169182 0.114 Uiso 0.0208 1 d R U P B -1
H1B H 0.553569 0.217224 0.275542 0.114 Uiso 0.0208 1 d R U P B -1
H1C H 0.740159 0.300124 0.310522 0.114 Uiso 0.0208 1 d R U P B -1
C2 C 0.355(5) 0.484(6) 0.368(6) 0.076(6) Uani 0.0208 1 d D U P B -1
H2A H 0.287842 0.375029 0.357821 0.091 Uiso 0.0208 1 calc R U P B -1
H2B H 0.352259 0.544179 0.255467 0.091 Uiso 0.0208 1 calc R U P B -1
C3 C 0.650(6) 0.608(5) 0.429(5) 0.076(6) Uani 0.0208 1 d D U P B -1
H3A H 0.653164 0.664979 0.314396 0.091 Uiso 0.0208 1 calc R U P B -1
H3B H 0.769592 0.579652 0.464070 0.091 Uiso 0.0208 1 calc R U P B -1
C4 C 0.544(6) 0.348(5) 0.592(5) 0.076(6) Uani 0.0208 1 d D U P B -1
H4A H 0.663799 0.312038 0.620712 0.091 Uiso 0.0208 1 calc R U P B -1
H4B H 0.471197 0.242427 0.584740 0.091 Uiso 0.0208 1 calc R U P B -1
C5 C 0.274(4) 0.604(6) 0.516(8) 0.076(6) Uani 0.0208 1 d D U P B -1
H5A H 0.232096 0.713196 0.463629 0.091 Uiso 0.0208 1 calc R U P B -1
H5B H 0.173550 0.544252 0.569064 0.091 Uiso 0.0208 1 calc R U P B -1
C6 C 0.471(6) 0.476(6) 0.737(4) 0.076(6) Uani 0.0208 1 d D U P B -1
H6A H 0.373381 0.419839 0.798724 0.091 Uiso 0.0208 1 calc R U P B -1
H6B H 0.562718 0.501720 0.822211 0.091 Uiso 0.0208 1 calc R U P B -1
C7 C 0.562(6) 0.733(4) 0.568(7) 0.076(6) Uani 0.0208 1 d D U P B -1
H7A H 0.648521 0.764481 0.657322 0.091 Uiso 0.0208 1 calc R U P B -1
H7B H 0.522726 0.840042 0.510541 0.091 Uiso 0.0208 1 calc R U P B -1
N3 N 0.000000 1.000000 1.000000 0.080(3) Uani 1 48 d S T P . .
H3C H -0.070750 1.060680 0.928300 0.096 Uiso 0.0208 1 d R U P C -1
H3D H 0.060440 1.074660 1.067840 0.096 Uiso 0.0208 1 d R U P C -1
H3E H -0.064580 0.928890 1.067840 0.096 Uiso 0.0208 1 d R U P C -1
H3F H 0.074900 0.935760 0.936020 0.096 Uiso 0.0208 1 d R U P C -1


_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
Cl1 O1 1.425(10) . ?
N1 C1 1.49(2) . ?
N1 C2 1.496(15) . ?
N1 C3 1.491(16) . ?
N1 C4 1.494(16) . ?
N2 H2 0.9800 . ?
N2 C5 1.491(16) . ?
N2 C6 1.489(16) . ?
N2 C7 1.493(16) . ?
C1 H1A 0.9599 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9601 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C5 1.565(18) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C7 1.562(18) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C6 1.569(18) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N3 H3C 0.8899 . ?
N3 H3D 0.8900 . ?
N3 H3E 0.8900 . ?
N3 H3F 0.8900 . ?

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 108.5(14) . . ?
C1 N1 C3 108.7(14) . . ?
C1 N1 C4 108.6(14) . . ?
C3 N1 C2 111(2) . . ?
C3 N1 C4 111(2) . . ?
C4 N1 C2 109(2) . . ?
C5 N2 H2 109.8 . . ?
C5 N2 C7 109(2) . . ?
C6 N2 H2 109.8 . . ?
C6 N2 C5 110(2) . . ?
C6 N2 C7 109(2) . . ?
C7 N2 H2 109.8 . . ?
N1 C1 H1A 109.0 . . ?
N1 C1 H1B 109.8 . . ?
N1 C1 H1C 109.6 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 110.1 . . ?
N1 C2 H2B 110.1 . . ?
N1 C2 C5 108.1(16) . . ?
H2A C2 H2B 108.4 . . ?
C5 C2 H2A 110.1 . . ?
C5 C2 H2B 110.1 . . ?
N1 C3 H3A 110.1 . . ?
N1 C3 H3B 110.1 . . ?
N1 C3 C7 108.1(17) . . ?
H3A C3 H3B 108.4 . . ?
C7 C3 H3A 110.1 . . ?
C7 C3 H3B 110.1 . . ?
N1 C4 H4A 110.1 . . ?
N1 C4 H4B 110.1 . . ?
N1 C4 C6 108.1(16) . . ?
H4A C4 H4B 108.4 . . ?
C6 C4 H4A 110.1 . . ?
C6 C4 H4B 110.1 . . ?
N2 C5 C2 110.2(19) . . ?
N2 C5 H5A 109.6 . . ?
N2 C5 H5B 109.6 . . ?
C2 C5 H5A 109.6 . . ?
C2 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
N2 C6 C4 109.9(18) . . ?
N2 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C4 C6 H6A 109.7 . . ?
C4 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C3 110.3(18) . . ?
N2 C7 H7A 109.6 . . ?
N2 C7 H7B 109.6 . . ?
C3 C7 H7A 109.6 . . ?
C3 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
H3C N3 H3D 109.5 . . ?
H3C N3 H3E 109.5 . . ?
H3C N3 H3F 109.5 . . ?
H3D N3 H3E 109.5 . . ?
H3D N3 H3F 109.5 . . ?
H3E N3 H3F 109.5 . . ?

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
N1 C2 C5 N2 2(4) . . . . ?
N1 C3 C7 N2 4(3) . . . . ?
N1 C4 C6 N2 5(4) . . . . ?
C1 N1 C2 C5 179(2) . . . . ?
C1 N1 C3 C7 178(2) . . . . ?
C1 N1 C4 C6 177(2) . . . . ?
C2 N1 C3 C7 59(3) . . . . ?
C2 N1 C4 C6 -64(3) . . . . ?
C3 N1 C2 C5 -62(3) . . . . ?
C3 N1 C4 C6 58(3) . . . . ?
C4 N1 C2 C5 60(3) . . . . ?
C4 N1 C3 C7 -63(3) . . . . ?
C5 N2 C6 C4 56(3) . . . . ?
C5 N2 C7 C3 -62(3) . . . . ?
C6 N2 C5 C2 -60(3) . . . . ?
C6 N2 C7 C3 58(3) . . . . ?
C7 N2 C5 C2 59(3) . . . . ?
C7 N2 C6 C4 -63(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
;
# start Validation Reply Form
_vrf_PLAT088_393_pm-3m           
;
PROBLEM: Poor Data / Parameter Ratio ....................       2.52 Note  
RESPONSE: ...The crystal structure is highly disordered at higher temperature, 
                     and multi-parameter restraints were to be enforced.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_a22010904a0248
_database_code_depnum_ccdc_archive 'CCDC 2234259'
loop_
_audit_author_name
_audit_author_address
'Wei-Xiong Zhang'
;SYSU
China
;
_audit_update_record             
;
2023-01-04 deposited with the CCDC.	2023-03-10 downloaded from the CCDC.
;
_audit_creation_date             2023-01-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H20 Cl3 N3 O12'
_chemical_formula_sum            'C7 H20 Cl3 N3 O12'
_chemical_formula_weight         444.61
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C7H20O12N3Cl3
_chemical_oxdiff_usercomment     'DAP-M4 293'
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.20664(11)
_cell_length_b                   11.00567(11)
_cell_length_c                   14.84750(16)
_cell_angle_alpha                90
_cell_angle_beta                 90.1263(10)
_cell_angle_gamma                90
_cell_volume                     1667.83(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10580
_cell_measurement_temperature    293.00(10)
_cell_measurement_theta_max      72.8180
_cell_measurement_theta_min      4.3140
_shelx_estimated_absorpt_T_max   0.728
_shelx_estimated_absorpt_T_min   0.265
_exptl_absorpt_coefficient_mu    5.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.771
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12895
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.960
_diffrn_reflns_theta_min         2.976
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -28.00   1.00    1.00    --  -41.14 -38.00  90.00   86
  2  ω    -92.00 -57.00   1.00    1.00    --  -41.14-163.00 -86.00   35
  3  ω    -50.00  25.00   1.00    1.00    --  -41.14  38.00-120.00   75
  4  ω     24.00  55.00   1.00    1.00    --   41.14 -99.00 -60.00   31
  5  ω    114.00 147.00   1.00    2.00    --  105.29  61.00-180.00   33
  6  ω     97.00 161.00   1.00    2.00    --  105.29 125.00 -60.00   64
  7  ω     30.00 105.00   1.00    2.00    --  105.29 -30.00 -60.00   75
  8  ω    121.00 164.00   1.00    2.00    --  105.29  77.00  90.00   43
  9  ω     39.00 103.00   1.00    2.00    --  105.29-125.00-180.00   64
 10  ω    105.00 157.00   1.00    2.00    --  105.29  77.00-150.00   52
 11  ω     82.00 171.00   1.00    2.00    --  105.29  45.00 120.00   89
 12  ω    -92.00 -18.00   1.00    1.00    --  -41.52 -38.00 150.00   74
 13  ω   -117.00 -91.00   1.00    1.00    --  -41.52-164.00 -85.00   26
 14  ω    -46.00 -12.00   1.00    1.00    --  -41.52 125.00-120.00   34
 15  ω     30.00  56.00   1.00    1.00    --   41.52-125.00-180.00   26
 16  ω     76.00 113.00   1.00    2.00    --  105.29  61.00-150.00   37
 17  ω     81.00 107.00   1.00    2.00    --  105.29  45.00-150.00   26
 18  ω     77.00 174.00   1.00    2.00    --  105.29  30.00  60.00   97
 19  ω     76.00 101.00   1.00    2.00    --  105.29  61.00-180.00   25
 20  ω     34.00  82.00   1.00    2.00    --  105.29 -94.00   0.00   48
 21  ω    107.00 140.00   1.00    2.00    --  105.29  77.00 -60.00   33
 22  ω     77.00 103.00   1.00    2.00    --  105.29  61.00-120.00   26
 23  ω    125.00 164.00   1.00    2.00    --  105.29  77.00   0.00   39
 24  ω     79.00 105.00   1.00    2.00    --  105.29  45.00 150.00   26
 25  ω     76.00 102.00   1.00    2.00    --  105.29  61.00 150.00   26
 26  ω     80.00 125.00   1.00    2.00    --  105.29  45.00-180.00   45
 27  ω     23.00  48.00   1.00    2.00    --  105.29 -94.00 -60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1090243000
_diffrn_orient_matrix_UB_12      0.0881758000
_diffrn_orient_matrix_UB_13      0.0294343000
_diffrn_orient_matrix_UB_21      -0.0478706000
_diffrn_orient_matrix_UB_22      0.0090647000
_diffrn_orient_matrix_UB_23      -0.0982452000
_diffrn_orient_matrix_UB_31      -0.0927669000
_diffrn_orient_matrix_UB_32      -0.1083322000
_diffrn_orient_matrix_UB_33      0.0157300000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                6387
_reflns_number_total             6453
_reflns_odcompleteness_completeness 100.00
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Twinning involves inversion, so Flack parameter cannot be determined
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_extinction_coef       0.0021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         6453
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0766P)²+0.0863P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1032
_refine_special_details          
;
 Refined as a 4-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.65(2)
 0.010(10) 0.314(15) 0.024(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H,H,H,H) groups
3.a Riding coordinates:
 N5(H5C,H5D,H5E,H5F), N6(H6C,H6D,H6E,H6F)
3.b Ternary CH refined with riding coordinates:
 N2(H2), N4(H4)
3.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B)
3.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
Cl1 Cl 0.00096(8) 0.21797(9) 0.49210(6) 0.0322(2) Uani 1 1 d . . . . .
O1 O 0.0206(4) 0.0897(3) 0.4866(3) 0.0583(10) Uani 1 1 d . . . . .
O2 O 0.0780(3) 0.2665(4) 0.5647(2) 0.0503(8) Uani 1 1 d . . . . .
O3 O -0.1350(3) 0.2417(3) 0.5093(2) 0.0485(8) Uani 1 1 d . . . . .
O4 O 0.0407(4) 0.2742(4) 0.4097(2) 0.0598(9) Uani 1 1 d . . . . .
Cl2 Cl 0.22119(8) 0.51062(8) 0.24785(6) 0.0288(2) Uani 1 1 d . . . . .
O5 O 0.2868(3) 0.4217(3) 0.3020(2) 0.0470(7) Uani 1 1 d . . . . .
O6 O 0.1629(3) 0.6010(3) 0.3052(2) 0.0468(8) Uani 1 1 d . . . . .
O7 O 0.3146(3) 0.5678(3) 0.1896(2) 0.0467(7) Uani 1 1 d . . . . .
O8 O 0.1224(3) 0.4540(3) 0.1938(2) 0.0504(8) Uani 1 1 d . . . . .
Cl3 Cl 0.49386(8) 0.77734(9) -0.00163(6) 0.0308(2) Uani 1 1 d . . . . .
O9 O 0.5269(4) 0.6522(3) -0.0134(3) 0.0544(9) Uani 1 1 d . . . . .
O10 O 0.5584(4) 0.8233(4) 0.0778(2) 0.0544(8) Uani 1 1 d . . . . .
O11 O 0.3552(3) 0.7879(4) 0.0091(3) 0.0564(9) Uani 1 1 d . . . . .
O12 O 0.5354(4) 0.8483(4) -0.0771(2) 0.0547(9) Uani 1 1 d . . . . .
Cl4 Cl 0.50560(8) 0.70803(9) 0.48692(6) 0.0311(2) Uani 1 1 d . . . . .
O13 O 0.4286(3) 0.6904(4) 0.4071(2) 0.0512(8) Uani 1 1 d . . . . .
O14 O 0.6382(3) 0.6752(5) 0.4705(3) 0.0695(12) Uani 1 1 d . . . . .
O15 O 0.4996(4) 0.8347(3) 0.5114(3) 0.0571(9) Uani 1 1 d . . . . .
O16 O 0.4535(3) 0.6365(3) 0.5587(2) 0.0460(7) Uani 1 1 d . . . . .
Cl5 Cl 0.27415(8) 0.48200(8) 0.74646(6) 0.0315(2) Uani 1 1 d . . . . .
O17 O 0.3589(4) 0.4054(4) 0.6953(3) 0.0627(10) Uani 1 1 d . . . . .
O18 O 0.1878(3) 0.5444(3) 0.6853(2) 0.0448(7) Uani 1 1 d . . . . .
O19 O 0.3498(4) 0.5682(4) 0.7974(3) 0.0625(10) Uani 1 1 d . . . . .
O20 O 0.1984(3) 0.4095(3) 0.8074(2) 0.0496(8) Uani 1 1 d . . . . .
Cl6 Cl -0.00513(8) 0.27897(9) 0.98113(6) 0.0315(2) Uani 1 1 d . . . . .
O21 O 0.1357(3) 0.2664(3) 0.9767(2) 0.0435(7) Uani 1 1 d . . . . .
O22 O -0.0364(4) 0.4058(3) 0.9814(3) 0.0593(9) Uani 1 1 d . . . . .
O23 O -0.0631(3) 0.2211(4) 0.9044(2) 0.0576(9) Uani 1 1 d . . . . .
O24 O -0.0527(3) 0.2231(4) 1.0613(2) 0.0529(9) Uani 1 1 d . . . . .
N1 N 0.2653(3) -0.0634(3) 0.7299(2) 0.0259(6) Uani 1 1 d . . . . .
N2 N 0.2565(3) 0.1320(3) 0.8175(2) 0.0360(7) Uani 1 1 d . . . . .
H2 H 0.2528 0.2082 0.8516 0.043 Uiso 1 1 calc R . . . .
C1 C 0.1738(4) 0.0250(4) 0.6854(3) 0.0385(9) Uani 1 1 d . . . . .
H1A H 0.2083 0.0481 0.6270 0.046 Uiso 1 1 calc R . . . .
H1B H 0.0891 -0.0130 0.6762 0.046 Uiso 1 1 calc R . . . .
C2 C 0.1585(5) 0.1358(4) 0.7431(4) 0.0506(11) Uani 1 1 d . . . . .
H2A H 0.1715 0.2083 0.7071 0.061 Uiso 1 1 calc R . . . .
H2B H 0.0707 0.1385 0.7679 0.061 Uiso 1 1 calc R . . . .
C3 C 0.3993(4) -0.0069(4) 0.7353(3) 0.0375(9) Uani 1 1 d . . . . .
H3A H 0.4353 0.0021 0.6753 0.045 Uiso 1 1 calc R . . . .
H3B H 0.4575 -0.0588 0.7699 0.045 Uiso 1 1 calc R . . . .
C4 C 0.3889(4) 0.1164(5) 0.7801(4) 0.0524(12) Uani 1 1 d . . . . .
H4A H 0.4535 0.1228 0.8279 0.063 Uiso 1 1 calc R . . . .
H4B H 0.4062 0.1798 0.7363 0.063 Uiso 1 1 calc R . . . .
C5 C 0.2173(5) -0.0874(4) 0.8235(3) 0.0414(9) Uani 1 1 d . . . . .
H5A H 0.2700 -0.1504 0.8513 0.050 Uiso 1 1 calc R . . . .
H5B H 0.1272 -0.1153 0.8214 0.050 Uiso 1 1 calc R . . . .
C6 C 0.2259(6) 0.0282(5) 0.8787(3) 0.0586(14) Uani 1 1 d . . . . .
H6A H 0.1434 0.0427 0.9091 0.070 Uiso 1 1 calc R . . . .
H6B H 0.2940 0.0202 0.9240 0.070 Uiso 1 1 calc R . . . .
C7 C 0.2714(6) -0.1790(4) 0.6777(4) 0.0553(13) Uani 1 1 d . . . . .
H7A H 0.1900 -0.2218 0.6838 0.083 Uiso 1 1 calc GR . . . .
H7B H 0.3415 -0.2284 0.7003 0.083 Uiso 1 1 calc GR . . . .
H7C H 0.2865 -0.1610 0.6153 0.083 Uiso 1 1 calc GR . . . .
N3 N 0.2380(3) 1.0630(3) 0.2291(2) 0.0246(6) Uani 1 1 d . . . . .
N4 N 0.2396(4) 0.8686(3) 0.3164(2) 0.0363(7) Uani 1 1 d . . . . .
H4 H 0.2401 0.7924 0.3505 0.044 Uiso 1 1 calc R . . . .
C8 C 0.3109(4) 0.9672(4) 0.1778(3) 0.0393(9) Uani 1 1 d . . . . .
H8A H 0.3963 0.9977 0.1602 0.047 Uiso 1 1 calc R . . . .
H8B H 0.2629 0.9459 0.1236 0.047 Uiso 1 1 calc R . . . .
C9 C 0.3269(5) 0.8559(4) 0.2372(3) 0.0443(10) Uani 1 1 d . . . . .
H9A H 0.3040 0.7833 0.2036 0.053 Uiso 1 1 calc R . . . .
H9B H 0.4172 0.8487 0.2569 0.053 Uiso 1 1 calc R . . . .
C10 C 0.3034(4) 1.0821(4) 0.3182(3) 0.0411(9) Uani 1 1 d . . . . .
H10A H 0.2643 1.1511 0.3486 0.049 Uiso 1 1 calc R . . . .
H10B H 0.3957 1.0990 0.3093 0.049 Uiso 1 1 calc R . . . .
C11 C 0.2874(5) 0.9685(5) 0.3756(3) 0.0483(11) Uani 1 1 d . . . . .
H11A H 0.3707 0.9463 0.4025 0.058 Uiso 1 1 calc R . . . .
H11B H 0.2251 0.9834 0.4235 0.058 Uiso 1 1 calc R . . . .
C12 C 0.1006(4) 1.0209(4) 0.2446(3) 0.0403(9) Uani 1 1 d . . . . .
H12A H 0.0531 1.0195 0.1880 0.048 Uiso 1 1 calc R . . . .
H12B H 0.0563 1.0766 0.2850 0.048 Uiso 1 1 calc R . . . .
C13 C 0.1027(4) 0.8946(5) 0.2854(3) 0.0476(11) Uani 1 1 d . . . . .
H13A H 0.0427 0.8905 0.3359 0.057 Uiso 1 1 calc R . . . .
H13B H 0.0757 0.8351 0.2410 0.057 Uiso 1 1 calc R . . . .
C14 C 0.2375(6) 1.1791(4) 0.1763(4) 0.0556(13) Uani 1 1 d . . . . .
H14A H 0.2135 1.1625 0.1150 0.083 Uiso 1 1 calc GR . . . .
H14B H 0.3233 1.2149 0.1780 0.083 Uiso 1 1 calc GR . . . .
H14C H 0.1753 1.2345 0.2022 0.083 Uiso 1 1 calc GR . . . .
N5 N 0.2468(3) 0.4698(3) 0.49571(19) 0.0341(7) Uani 1 1 d . . . . .
H5C H 0.2130 0.5484 0.4732 0.051 Uiso 1 1 d R . . . .
H5D H 0.2992 0.4351 0.4459 0.051 Uiso 1 1 d R . . . .
H5E H 0.1727 0.4147 0.5095 0.051 Uiso 1 1 d R . . . .
H5F H 0.3049 0.4830 0.5482 0.051 Uiso 1 1 d R . . . .
N6 N 0.2495(3) 0.5238(3) -0.0049(2) 0.0342(7) Uani 1 1 d . . . . .
H6C H 0.1905 0.5299 0.0477 0.051 Uiso 1 1 d R . . . .
H6D H 0.2024 0.4829 -0.0547 0.051 Uiso 1 1 d R . . . .
H6E H 0.2766 0.6059 -0.0247 0.051 Uiso 1 1 d R . . . .
H6F H 0.3281 0.4758 0.0114 0.051 Uiso 1 1 d R . . . .


_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
Cl1 O1 1.429(4) . ?
Cl1 O2 1.436(3) . ?
Cl1 O3 1.435(3) . ?
Cl1 O4 1.431(3) . ?
Cl2 O5 1.432(3) . ?
Cl2 O6 1.439(3) . ?
Cl2 O7 1.434(3) . ?
Cl2 O8 1.430(3) . ?
Cl3 O9 1.429(4) . ?
Cl3 O10 1.441(3) . ?
Cl3 O11 1.429(3) . ?
Cl3 O12 1.431(3) . ?
Cl4 O13 1.434(3) . ?
Cl4 O14 1.423(3) . ?
Cl4 O15 1.442(4) . ?
Cl4 O16 1.429(3) . ?
Cl5 O17 1.427(4) . ?
Cl5 O18 1.439(3) . ?
Cl5 O19 1.437(4) . ?
Cl5 O20 1.434(3) . ?
Cl6 O21 1.446(3) . ?
Cl6 O22 1.431(4) . ?
Cl6 O23 1.432(3) . ?
Cl6 O24 1.426(3) . ?
N1 C1 1.500(5) . ?
N1 C3 1.504(5) . ?
N1 C5 1.499(5) . ?
N1 C7 1.491(5) . ?
N2 H2 0.9800 . ?
N2 C2 1.490(6) . ?
N2 C4 1.472(6) . ?
N2 C6 1.494(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.499(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.515(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.515(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
N3 C8 1.499(5) . ?
N3 C10 1.495(5) . ?
N3 C12 1.495(5) . ?
N3 C14 1.499(5) . ?
N4 H4 0.9800 . ?
N4 C9 1.484(5) . ?
N4 C11 1.488(6) . ?
N4 C13 1.498(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.518(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.522(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.516(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N5 H5C 0.9902 . ?
N5 H5D 0.9904 . ?
N5 H5E 0.9907 . ?
N5 H5F 0.9894 . ?
N6 H6C 0.9897 . ?
N6 H6D 0.9904 . ?
N6 H6E 0.9897 . ?
N6 H6F 0.9896 . ?

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 Cl1 O2 109.5(2) . . ?
O1 Cl1 O3 109.0(2) . . ?
O1 Cl1 O4 109.8(3) . . ?
O3 Cl1 O2 109.1(2) . . ?
O4 Cl1 O2 109.0(2) . . ?
O4 Cl1 O3 110.5(2) . . ?
O5 Cl2 O6 109.5(2) . . ?
O5 Cl2 O7 109.1(2) . . ?
O7 Cl2 O6 109.3(2) . . ?
O8 Cl2 O5 110.2(2) . . ?
O8 Cl2 O6 109.9(2) . . ?
O8 Cl2 O7 108.7(2) . . ?
O9 Cl3 O10 109.3(2) . . ?
O9 Cl3 O12 111.1(2) . . ?
O11 Cl3 O9 109.1(2) . . ?
O11 Cl3 O10 109.3(2) . . ?
O11 Cl3 O12 109.8(2) . . ?
O12 Cl3 O10 108.3(2) . . ?
O13 Cl4 O15 108.4(2) . . ?
O14 Cl4 O13 110.1(2) . . ?
O14 Cl4 O15 109.3(3) . . ?
O14 Cl4 O16 110.1(2) . . ?
O16 Cl4 O13 109.8(2) . . ?
O16 Cl4 O15 109.2(2) . . ?
O17 Cl5 O18 108.5(2) . . ?
O17 Cl5 O19 110.1(3) . . ?
O17 Cl5 O20 109.6(2) . . ?
O19 Cl5 O18 110.1(2) . . ?
O20 Cl5 O18 109.5(2) . . ?
O20 Cl5 O19 109.0(2) . . ?
O22 Cl6 O21 108.3(2) . . ?
O22 Cl6 O23 110.1(2) . . ?
O23 Cl6 O21 109.3(2) . . ?
O24 Cl6 O21 109.7(2) . . ?
O24 Cl6 O22 110.0(2) . . ?
O24 Cl6 O23 109.3(2) . . ?
C1 N1 C3 108.7(3) . . ?
C5 N1 C1 108.5(3) . . ?
C5 N1 C3 108.9(3) . . ?
C7 N1 C1 110.5(3) . . ?
C7 N1 C3 110.0(3) . . ?
C7 N1 C5 110.2(4) . . ?
C2 N2 H2 109.4 . . ?
C2 N2 C6 109.4(4) . . ?
C4 N2 H2 109.4 . . ?
C4 N2 C2 109.8(4) . . ?
C4 N2 C6 109.5(4) . . ?
C6 N2 H2 109.4 . . ?
N1 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C2 C1 N1 110.0(3) . . ?
C2 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
N2 C2 C1 109.2(3) . . ?
N2 C2 H2A 109.8 . . ?
N2 C2 H2B 109.8 . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
N1 C3 H3A 109.8 . . ?
N1 C3 H3B 109.8 . . ?
N1 C3 C4 109.2(3) . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
N2 C4 C3 109.6(3) . . ?
N2 C4 H4A 109.7 . . ?
N2 C4 H4B 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N1 C5 H5A 109.8 . . ?
N1 C5 H5B 109.8 . . ?
N1 C5 C6 109.6(3) . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 H5A 109.8 . . ?
C6 C5 H5B 109.8 . . ?
N2 C6 C5 109.0(3) . . ?
N2 C6 H6A 109.9 . . ?
N2 C6 H6B 109.9 . . ?
C5 C6 H6A 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C10 N3 C8 109.1(3) . . ?
C10 N3 C14 110.1(3) . . ?
C12 N3 C8 109.1(3) . . ?
C12 N3 C10 108.9(3) . . ?
C12 N3 C14 110.0(3) . . ?
C14 N3 C8 109.6(3) . . ?
C9 N4 H4 109.0 . . ?
C9 N4 C11 109.9(4) . . ?
C9 N4 C13 109.6(3) . . ?
C11 N4 H4 109.0 . . ?
C11 N4 C13 110.2(4) . . ?
C13 N4 H4 109.0 . . ?
N3 C8 H8A 109.9 . . ?
N3 C8 H8B 109.9 . . ?
N3 C8 C9 109.0(3) . . ?
H8A C8 H8B 108.3 . . ?
C9 C8 H8A 109.9 . . ?
C9 C8 H8B 109.9 . . ?
N4 C9 C8 108.7(3) . . ?
N4 C9 H9A 110.0 . . ?
N4 C9 H9B 110.0 . . ?
C8 C9 H9A 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.3 . . ?
N3 C10 H10A 109.8 . . ?
N3 C10 H10B 109.8 . . ?
N3 C10 C11 109.4(3) . . ?
H10A C10 H10B 108.2 . . ?
C11 C10 H10A 109.8 . . ?
C11 C10 H10B 109.8 . . ?
N4 C11 C10 108.2(3) . . ?
N4 C11 H11A 110.1 . . ?
N4 C11 H11B 110.1 . . ?
C10 C11 H11A 110.1 . . ?
C10 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
N3 C12 H12A 109.8 . . ?
N3 C12 H12B 109.8 . . ?
N3 C12 C13 109.5(3) . . ?
H12A C12 H12B 108.2 . . ?
C13 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
N4 C13 C12 108.0(3) . . ?
N4 C13 H13A 110.1 . . ?
N4 C13 H13B 110.1 . . ?
C12 C13 H13A 110.1 . . ?
C12 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H5C N5 H5D 105.9 . . ?
H5C N5 H5E 109.8 . . ?
H5C N5 H5F 110.2 . . ?
H5D N5 H5E 109.4 . . ?
H5D N5 H5F 108.8 . . ?
H5E N5 H5F 112.6 . . ?
H6C N6 H6D 108.9 . . ?
H6C N6 H6E 110.1 . . ?
H6C N6 H6F 109.7 . . ?
H6D N6 H6E 109.2 . . ?
H6D N6 H6F 109.4 . . ?
H6E N6 H6F 109.5 . . ?

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
N2 H2 O20 0.98 2.38 3.115(5) 131.6 .
N2 H2 O21 0.98 2.30 3.051(4) 132.5 .
N4 H4 O3 0.98 2.41 3.131(5) 130.0 2_556
N4 H4 O6 0.98 2.35 3.052(5) 128.2 .
N4 H4 O13 0.98 2.38 3.061(5) 126.1 .
N5 H5D O5 0.99 2.14 2.954(4) 137.7 .
N5 H5E O2 0.99 2.07 3.005(5) 157.3 .
N5 H5F O16 0.99 2.28 2.947(5) 124.2 .
N6 H6D O20 0.99 2.20 3.101(5) 150.4 1_554
N6 H6E O11 0.99 2.22 3.107(5) 149.3 .
N6 H6F O10 0.99 2.43 3.145(5) 128.4 2_645
N6 H6F O12 0.99 2.20 3.166(5) 163.6 2_645

_olex2_date_sample_data_collection 2022-01-09
_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 1.498
_oxdiff_exptl_absorpt_empirical_full_min 0.733
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.65(2)
2 0.010(10)
3 0.314(15)
4 0.024(10)

####################################################################### 
# 
# 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_358_r-3m
_database_code_depnum_ccdc_archive 'CCDC 2234258'
loop_
_audit_author_name
_audit_author_address
'Wei-Xiong Zhang'
;SYSU
China
;
_audit_update_record             
;
2023-01-04 deposited with the CCDC.	2023-03-10 downloaded from the CCDC.
;
_audit_creation_date             2022-10-24
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2021.12.21 svn.raa29eb21 for OlexSys, GUI svn.r6440)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H20 Cl3 N3 O12'
_chemical_formula_sum            'C7 H20 Cl3 N3 O12'
_chemical_formula_weight         444.61
_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 0.0181 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           166
_space_group_name_H-M_alt        'R -3 m'
_space_group_name_Hall           '-R 3 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -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'
'y+2/3, x+1/3, -z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+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'
'y+1/3, x+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, 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'
'-y+2/3, -x+1/3, z+1/3'
'-x+y+2/3, y+1/3, z+1/3'
'x+2/3, x-y+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'
'-y+1/3, -x+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+2/3'
'x+1/3, x-y+2/3, z+2/3'

_cell_length_a                   10.6675(8)
_cell_length_b                   10.6675(8)
_cell_length_c                   13.0585(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1286.9(2)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    1637
_cell_measurement_temperature    358.49(10)
_cell_measurement_theta_max      71.2840
_cell_measurement_theta_min      5.7890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.485
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.40t (Rigaku Oxford Diffraction, 2015)
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    1.721
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             690
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3110
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.468
_diffrn_reflns_theta_min         5.867
_diffrn_ambient_temperature      358.49(10)
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     19.00  82.00   1.00    4.15    --   41.14 -99.00-180.00   63
  2  ω     78.00 159.00   1.00   16.61    --  105.29  15.00  90.00   81
  3  ω   -114.00 -89.00   1.00    2.00    --  -41.52-146.00 171.00   25
  4  ω    -29.00  46.00   1.00    2.00    --   41.52 -57.00 150.00   75
  5  ω     12.00  79.00   1.00    2.00    --   41.52 -99.00  30.00   67
  6  ω    124.00 171.00   1.00    4.00    --  105.29 125.00  90.00   47
  7  ω    103.00 133.00   1.00    4.00    --  105.29 -61.00 -30.00   30
  8  ω     43.00  75.00   1.00    4.00    --  105.29 -61.00 -30.00   32
  9  ω    143.00 176.00   1.00    4.00    --  105.29  77.00  60.00   33
 10  ω    102.00 128.00   1.00    4.00    --  105.29 -15.00 -60.00   26
 11  ω    102.00 171.00   1.00    4.00    --  105.29  45.00 120.00   69
 12  ω     28.00  79.00   1.00    4.00    --  105.29 -15.00 -60.00   51
 13  ω   -114.00 -50.00   1.00    2.00    --  -41.52 -57.00  30.00   64
 14  ω    -38.00   5.00   1.00    2.00    --  -41.52  77.00-180.00   43
 15  ω     45.00 101.00   1.00    4.00    --  105.29-125.00 150.00   56
 16  ω     43.00 112.00   1.00    4.00    --  105.29-125.00  90.00   69
 17  ω    -54.00   5.00   1.00    2.00    --  -41.52  38.00 150.00   59
 18  ω    -32.00  32.00   1.00    2.00    --   41.52 -38.00-120.00   64
 19  ω     36.00  62.00   1.00    2.00    --   41.52 -38.00-120.00   26
 20  ω     28.00  56.00   1.00    8.00    --  105.29 -94.00 -90.00   28
 21  ω     38.00 123.00   1.00    8.00    --  105.29 -45.00 120.00   85
 22  ω     60.00 106.00   1.00    8.00    --  105.29 -94.00 -90.00   46
 23  ω    126.00 170.00   1.00    8.00    --  105.29  77.00 -90.00   44
 24  ω     75.00 110.00   1.00    8.00    --  105.29-125.00-150.00   35
 25  ω     71.00  97.00   1.00    8.00    --  105.29 -61.00-180.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                316
_reflns_number_total             335
_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 1.171.38.40t (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.40t (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.40t (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     58
_refine_ls_number_reflns         335
_refine_ls_number_restraints     238
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0642
_refine_ls_restrained_S_all      0.847
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1426P)²+1.0175P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2083
_refine_ls_wR_factor_ref         0.2126
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-C2 = N1-C4 = N2-C6
 1.48 with sigma of 0.02
 N1-C1
 1.48 with sigma of 0.01
 N1-C3 = N2-C7
 1.47 with sigma of 0.02
 C2-C7
 1.55 with sigma of 0.02
 N2-C5
 1.49 with sigma of 0.02
 C3-C6 = C4-C5
 1.56 with sigma of 0.02
 N1-C7 = N1-C6
 2.48 with sigma of 0.04
 N1-C5 = C2-N2 = N2-C3 = N2-C4
 2.49 with sigma of 0.04
 C2-C6 \\sim C7-C3 \\sim C6-C4 \\sim C3-C5 \\sim C2-C5 \\sim C7-C4
 with sigma of 0.05
 C1-C2 \\sim C1-C3 \\sim C1-C4
 with sigma of 0.01
 N1-C2 \\sim N1-C3 \\sim N1-C4 \\sim N2-C7 \\sim N2-C6 \\sim N2-C5
 with sigma of 0.02
 C2-C7 \\sim C3-C6 \\sim C4-C5
 with sigma of 0.02
 C2-C3 \\sim C3-C4 \\sim C2-C4 \\sim C7-C6 \\sim C7-C5 \\sim C6-C5
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
N1 \\sim N2 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(C5) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim
Ueq, Uanis(C4) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C6)
\\sim Ueq, Uanis(N2) \\sim Ueq: with sigma of 0.03 and sigma for terminal atoms
of 0.06
Uanis(C1) = Uanis(N1) = Uanis(C3) = Uanis(C4) = Uanis(C2) = Uanis(C6) =
Uanis(C5) = Uanis(C7) = Uanis(N2)
4. Rigid body (RIGU) restrains
 N1, N2, C2, C3, C4, C5, C6, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: O1(0.5) O2(0.5) N1(0.08333) N2(0.08333) H2(0.08333) C1(0.08333)
 H1A(0.08333) H1B(0.08333) H1C(0.08333) C2(0.08333) H2A(0.08333) H2B(0.08333)
 C3(0.08333) H3A(0.08333) H3B(0.08333) C4(0.08333) H4A(0.08333) H4B(0.08333)
 C5(0.08333) H5A(0.08333) H5B(0.08333) C6(0.08333) H6A(0.08333) H6B(0.08333)
 C7(0.08333) H7A(0.08333) H7B(0.08333) H3D(0.08333) H3C(0.08333) H3E(0.08333)
 H3F(0.08333)
6.a Riding coordinates:
 C1(H1A,H1B,H1C), N3(H3D), N3(H3C,H3E,H3F)
6.b Ternary CH refined with riding coordinates:
 N2(H2)
6.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Cl1 Cl 0.333333 0.166667 0.666667 0.1029(10) Uani 1 4 d S T P . .
O1 O 0.4590(8) 0.3045(8) 0.6528(6) 0.145(3) Uani 0.5 1 d . . P A -1
O2 O 0.3104(8) 0.2308(9) 0.5790(6) 0.146(3) Uani 0.5 1 d . . P A -2
N1 N 0.388(2) 0.644(2) 0.6941(16) 0.114(4) Uani 0.0833 1 d D U P B -1
N2 N 0.253(3) 0.719(3) 0.5971(18) 0.114(4) Uani 0.0833 1 d D U P B -1
H2 H 0.196703 0.750238 0.556643 0.137 Uiso 0.0833 1 calc R U P B -1
C1 C 0.473(3) 0.595(3) 0.754(2) 0.114(4) Uani 0.0833 1 d D U P B -1
H1A H 0.455243 0.503403 0.729019 0.171 Uiso 0.0833 1 d R U P B -1
H1B H 0.444723 0.586123 0.824909 0.171 Uiso 0.0833 1 d R U P B -1
H1C H 0.574063 0.665133 0.748069 0.171 Uiso 0.0833 1 d R U P B -1
C2 C 0.308(3) 0.521(3) 0.622(3) 0.114(4) Uani 0.0833 1 d D U P B -1
H2A H 0.245572 0.431238 0.658201 0.137 Uiso 0.0833 1 calc R U P B -1
H2B H 0.373574 0.507030 0.578294 0.137 Uiso 0.0833 1 calc R U P B -1
C3 C 0.295(3) 0.657(5) 0.7735(17) 0.114(4) Uani 0.0833 1 d D U P B -1
H3A H 0.352939 0.727034 0.825774 0.137 Uiso 0.0833 1 calc R U P B -1
H3B H 0.230713 0.564926 0.805513 0.137 Uiso 0.0833 1 calc R U P B -1
C4 C 0.502(3) 0.783(3) 0.650(3) 0.114(4) Uani 0.0833 1 d D U P B -1
H4A H 0.569648 0.768503 0.608421 0.137 Uiso 0.0833 1 calc R U P B -1
H4B H 0.554832 0.853330 0.702721 0.137 Uiso 0.0833 1 calc R U P B -1
C5 C 0.410(3) 0.830(3) 0.582(2) 0.114(4) Uani 0.0833 1 d D U P B -1
H5A H 0.427318 0.924398 0.602189 0.137 Uiso 0.0833 1 calc R U P B -1
H5B H 0.435521 0.833634 0.509984 0.137 Uiso 0.0833 1 calc R U P B -1
C6 C 0.208(3) 0.713(4) 0.7066(18) 0.114(4) Uani 0.0833 1 d D U P B -1
H6A H 0.104914 0.647386 0.713562 0.137 Uiso 0.0833 1 calc R U P B -1
H6B H 0.230023 0.808241 0.729291 0.137 Uiso 0.0833 1 calc R U P B -1
C7 C 0.216(4) 0.573(3) 0.558(2) 0.114(4) Uani 0.0833 1 d D U P B -1
H7A H 0.239677 0.578229 0.486092 0.137 Uiso 0.0833 1 calc R U P B -1
H7B H 0.113693 0.505728 0.566897 0.137 Uiso 0.0833 1 calc R U P B -1
N3 N 0.000000 0.000000 0.500000 0.0785(19) Uani 1 12 d S T P . .
H3D H 0.065090 -0.022330 0.477300 0.094 Uiso 0.0833 1 d R U P C -2
H3C H -0.087400 -0.065080 0.477270 0.094 Uiso 0.0833 1 d R U P C -2
H3E H 0.022340 0.087410 0.477270 0.094 Uiso 0.0833 1 d R U P C -2
H3F H 0.005770 0.008600 0.568090 0.094 Uiso 0.0833 1 d R U P C -2


_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
Cl1 O1 1.421(8) . ?
Cl1 O2 1.417(7) . ?
N1 C1 1.476(11) . ?
N1 C2 1.488(13) . ?
N1 C3 1.488(13) . ?
N1 C4 1.489(13) . ?
N2 H2 0.9800 . ?
N2 C5 1.499(13) . ?
N2 C6 1.499(13) . ?
N2 C7 1.487(13) . ?
C1 H1A 0.9602 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9601 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C7 1.580(15) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C6 1.588(15) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.585(15) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N3 H3D 0.8900 . ?
N3 H3C 0.8900 . ?
N3 H3E 0.8900 . ?
N3 H3F 0.8928 . ?

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 102.2(11) . . ?
C1 N1 C3 102.6(11) . . ?
C1 N1 C4 102.2(11) . . ?
C2 N1 C4 117.0(17) . . ?
C3 N1 C2 114.4(18) . . ?
C3 N1 C4 115.3(17) . . ?
C5 N2 H2 106.8 . . ?
C5 N2 C6 111.6(17) . . ?
C6 N2 H2 106.8 . . ?
C7 N2 H2 106.8 . . ?
C7 N2 C5 112.8(18) . . ?
C7 N2 C6 111.7(18) . . ?
N1 C1 H1A 109.4 . . ?
N1 C1 H1B 109.4 . . ?
N1 C1 H1C 109.6 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 111.4 . . ?
N1 C2 H2B 111.4 . . ?
N1 C2 C7 101.7(14) . . ?
H2A C2 H2B 109.3 . . ?
C7 C2 H2A 111.4 . . ?
C7 C2 H2B 111.4 . . ?
N1 C3 H3A 111.6 . . ?
N1 C3 H3B 111.6 . . ?
N1 C3 C6 101.1(13) . . ?
H3A C3 H3B 109.4 . . ?
C6 C3 H3A 111.6 . . ?
C6 C3 H3B 111.6 . . ?
N1 C4 H4A 111.4 . . ?
N1 C4 H4B 111.4 . . ?
N1 C4 C5 101.7(13) . . ?
H4A C4 H4B 109.3 . . ?
C5 C4 H4A 111.4 . . ?
C5 C4 H4B 111.4 . . ?
N2 C5 C4 107.3(14) . . ?
N2 C5 H5A 110.3 . . ?
N2 C5 H5B 110.3 . . ?
C4 C5 H5A 110.3 . . ?
C4 C5 H5B 110.3 . . ?
H5A C5 H5B 108.5 . . ?
N2 C6 C3 107.8(14) . . ?
N2 C6 H6A 110.2 . . ?
N2 C6 H6B 110.2 . . ?
C3 C6 H6A 110.2 . . ?
C3 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
N2 C7 C2 107.6(14) . . ?
N2 C7 H7A 110.2 . . ?
N2 C7 H7B 110.2 . . ?
C2 C7 H7A 110.2 . . ?
C2 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
H3D N3 H3C 109.5 . . ?
H3D N3 H3E 109.5 . . ?
H3D N3 H3F 109.6 . . ?
H3C N3 H3E 109.5 . . ?
H3C N3 H3F 113.8 . . ?
H3E N3 H3F 104.8 . . ?

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 C2 C7 N2 1(3) . . . . ?
N1 C3 C6 N2 3(3) . . . . ?
N1 C4 C5 N2 3(3) . . . . ?
C1 N1 C2 C7 179.8(17) . . . . ?
C1 N1 C3 C6 178.6(18) . . . . ?
C1 N1 C4 C5 177.7(18) . . . . ?
C2 N1 C3 C6 -72(2) . . . . ?
C2 N1 C4 C5 67(3) . . . . ?
C3 N1 C2 C7 70(2) . . . . ?
C3 N1 C4 C5 -72(3) . . . . ?
C4 N1 C2 C7 -70(2) . . . . ?
C4 N1 C3 C6 68(2) . . . . ?
C5 N2 C6 C3 -65(2) . . . . ?
C5 N2 C7 C2 62(2) . . . . ?
C6 N2 C5 C4 62(3) . . . . ?
C6 N2 C7 C2 -64(3) . . . . ?
C7 N2 C5 C4 -65(3) . . . . ?
C7 N2 C6 C3 62(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
;
# start Validation Reply Form
_vrf_PLAT088_358_r-3m            
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.79 Note  
RESPONSE: The crystal structure is highly disordered at high temperature, 
                  and multi-parameter restraints were to be enforced.
;
# end Validation Reply Form
