# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_22020923tj_0m_4
_database_code_depnum_ccdc_archive 'CCDC 2053151'
loop_
_audit_author_name
_audit_author_address
'jie Tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2021-08-20 deposited with the CCDC.	2021-08-24 downloaded from the CCDC.
;
_audit_creation_date             2021-08-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Cl O4), 3(H2 O), C7 H10 N10'
_chemical_formula_sum            'C7 H16 Cl2 N10 O11'
_chemical_formula_weight         487.20
_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 0.0033 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'
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.9672(3)
_cell_length_b                   12.7852(10)
_cell_length_c                   14.3081(13)
_cell_angle_alpha                88.990(3)
_cell_angle_beta                 81.510(2)
_cell_angle_gamma                86.431(2)
_cell_volume                     896.93(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2267
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.267
_cell_measurement_theta_min      3.195
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.446
_exptl_absorpt_correction_T_max  0.745373
_exptl_absorpt_correction_T_min  0.364216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 13275 reflections, Rint = 0.0794
 (7172 with I > 3sig(I), Rint = 0.0632)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0772
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2957
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        24.708
_diffrn_reflns_theta_max         24.708
_diffrn_reflns_theta_min         2.158
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2321
_reflns_number_total             2957
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0694
_refine_ls_restrained_S_all      1.044
_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)+(0.1220P)²+0.8247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1758
_refine_ls_wR_factor_ref         0.1968
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.796(3)
 0.204(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
3. Restrained distances
 H6A-H5B
 2.2 with sigma of 0.02
 H6A-H6A_$1
 2.2 with sigma of 0.02
4.a Free rotating group:
 O7(H7A,H7B), O5(H5A,H5B), O6(H6A,H6B)
4.b Aromatic/amide H refined with riding coordinates:
 N7(H7), N2(H2), N5(H5), N9(H9), N3(H3), C4(H4)
4.c X=CH2 refined with riding coordinates:
 N10(H10A,H10B), N1(H1A,H1B)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl2 Cl 0.2071(2) 0.90223(10) 0.37485(10) 0.0231(4) Uani 1 1 d . . . . .
Cl1 Cl -0.6983(2) 1.15142(10) 0.08836(10) 0.0257(4) Uani 1 1 d . . . . .
O10 O -0.0838(7) 0.8966(3) 0.3980(3) 0.0287(9) Uani 1 1 d . . . . .
O4 O -0.4071(7) 1.1401(3) 0.0774(3) 0.0392(11) Uani 1 1 d . . . . .
O7 O 0.3688(8) 0.6187(3) 0.4787(3) 0.0374(11) Uani 1 1 d . . . . .
H7A H 0.257200 0.673464 0.475443 0.056 Uiso 1 1 d G . . . .
H7B H 0.518772 0.626870 0.440114 0.056 Uiso 1 1 d G . . . .
O2 O -0.8070(8) 1.1767(3) 0.1850(3) 0.0405(11) Uani 1 1 d . . . . .
O9 O 0.2649(8) 0.9686(3) 0.2936(3) 0.0413(11) Uani 1 1 d . . . . .
O8 O 0.3315(7) 0.7988(3) 0.3540(3) 0.0331(10) Uani 1 1 d . . . . .
O3 O -0.7768(8) 1.2353(3) 0.0281(3) 0.0414(11) Uani 1 1 d . . . . .
N7 N -0.1573(8) 0.7624(3) 0.2284(3) 0.0242(10) Uani 1 1 d . . . . .
H7 H -0.301465 0.761797 0.272238 0.029 Uiso 1 1 calc R . . . .
N2 N 0.5106(8) 0.2885(3) 0.3114(3) 0.0264(11) Uani 1 1 d . . . . .
H2 H 0.620069 0.314625 0.263919 0.032 Uiso 1 1 calc R . . . .
O11 O 0.3138(8) 0.9458(3) 0.4526(3) 0.0383(11) Uani 1 1 d . . . . .
O1 O -0.8043(8) 1.0560(3) 0.0628(3) 0.0422(11) Uani 1 1 d . . . . .
N6 N -0.1454(8) 0.5741(4) 0.3400(3) 0.0279(11) Uani 1 1 d . . . . .
N5 N -0.0746(9) 0.4805(3) 0.3752(4) 0.0297(11) Uani 1 1 d . . . . .
H5 H -0.173371 0.449899 0.422814 0.036 Uiso 1 1 calc R . . . .
N9 N 0.1379(9) 0.8074(4) 0.1135(3) 0.0285(11) Uani 1 1 d . . . . .
H9 H 0.224194 0.844790 0.067591 0.034 Uiso 1 1 calc R . . . .
N10 N -0.2466(9) 0.9276(4) 0.1569(3) 0.0294(11) Uani 1 1 d . . . . .
H10A H -0.191282 0.973923 0.113192 0.035 Uiso 1 1 calc R . . . .
H10B H -0.400418 0.940128 0.195285 0.035 Uiso 1 1 calc R . . . .
N8 N 0.2302(9) 0.7090(4) 0.1408(3) 0.0281(11) Uani 1 1 d . . . . .
N3 N 0.3321(9) 0.1895(4) 0.4243(3) 0.0290(11) Uani 1 1 d . . . . .
H3 H 0.307747 0.136458 0.464077 0.035 Uiso 1 1 calc R . . . .
N1 N 0.7422(9) 0.1219(3) 0.3327(4) 0.0314(12) Uani 1 1 d . . . . .
H1A H 0.745822 0.063136 0.365588 0.038 Uiso 1 1 calc R . . . .
H1B H 0.871955 0.132459 0.285142 0.038 Uiso 1 1 calc R . . . .
N4 N 0.1581(9) 0.2782(3) 0.4259(4) 0.0293(11) Uani 1 1 d . . . . .
O5 O 0.8047(10) 0.3653(4) 0.1552(4) 0.0561(14) Uani 1 1 d . . . . .
H5A H 0.951895 0.336409 0.122815 0.084 Uiso 1 1 d G . . . .
H5B H 0.830310 0.432019 0.152807 0.084 Uiso 1 1 d DG . . . .
C1 C 0.5416(10) 0.1943(4) 0.3546(4) 0.0257(12) Uani 1 1 d . . . . .
C6 C 0.0500(10) 0.6847(4) 0.2122(4) 0.0229(12) Uani 1 1 d . . . . .
C3 C 0.1628(10) 0.4381(4) 0.3303(4) 0.0263(13) Uani 1 1 d . . . . .
C4 C 0.2553(10) 0.5065(4) 0.2601(4) 0.0277(13) Uani 1 1 d . . . . .
H4 H 0.416698 0.499276 0.215321 0.033 Uiso 1 1 calc R . . . .
C2 C 0.2718(10) 0.3345(4) 0.3576(4) 0.0270(13) Uani 1 1 d . . . . .
C7 C -0.0978(10) 0.8387(4) 0.1651(4) 0.0252(12) Uani 1 1 d . . . . .
C5 C 0.0566(10) 0.5898(4) 0.2694(4) 0.0260(13) Uani 1 1 d . . . . .
O6 O 0.7055(16) 0.5428(5) 0.0456(5) 0.101(2) Uani 1 1 d . . . . .
H6A H 0.706390 0.483026 0.017380 0.152 Uiso 1 1 d DG . . . .
H6B H 0.638719 0.598933 0.017268 0.152 Uiso 1 1 d G . . . .


_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
Cl2 O10 1.440(4) . ?
Cl2 O9 1.432(4) . ?
Cl2 O8 1.442(4) . ?
Cl2 O11 1.436(4) . ?
Cl1 O4 1.430(4) . ?
Cl1 O2 1.442(4) . ?
Cl1 O3 1.435(4) . ?
Cl1 O1 1.432(4) . ?
O7 H7A 0.8703 . ?
O7 H7B 0.8702 . ?
N7 H7 0.8800 . ?
N7 C6 1.383(6) . ?
N7 C7 1.335(7) . ?
N2 H2 0.8800 . ?
N2 C1 1.355(7) . ?
N2 C2 1.373(7) . ?
N6 N5 1.337(6) . ?
N6 C5 1.336(7) . ?
N5 H5 0.8800 . ?
N5 C3 1.344(7) . ?
N9 H9 0.8800 . ?
N9 N8 1.382(7) . ?
N9 C7 1.331(7) . ?
N10 H10A 0.8800 . ?
N10 H10B 0.8800 . ?
N10 C7 1.330(7) . ?
N8 C6 1.302(7) . ?
N3 H3 0.8800 . ?
N3 N4 1.382(6) . ?
N3 C1 1.334(7) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C1 1.323(7) . ?
N4 C2 1.287(7) . ?
O5 H5A 0.8702 . ?
O5 H5B 0.8700 . ?
C6 C5 1.453(8) . ?
C3 C4 1.367(8) . ?
C3 C2 1.467(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.401(7) . ?
O6 H6A 0.8700 . ?
O6 H6B 0.8882 . ?

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
O10 Cl2 O8 109.5(2) . . ?
O9 Cl2 O10 109.0(2) . . ?
O9 Cl2 O8 109.4(3) . . ?
O9 Cl2 O11 109.0(3) . . ?
O11 Cl2 O10 109.8(3) . . ?
O11 Cl2 O8 110.2(3) . . ?
O4 Cl1 O2 110.1(3) . . ?
O4 Cl1 O3 108.7(3) . . ?
O4 Cl1 O1 109.8(3) . . ?
O3 Cl1 O2 108.8(3) . . ?
O1 Cl1 O2 109.7(3) . . ?
O1 Cl1 O3 109.7(3) . . ?
H7A O7 H7B 109.4 . . ?
C6 N7 H7 126.4 . . ?
C7 N7 H7 126.4 . . ?
C7 N7 C6 107.2(4) . . ?
C1 N2 H2 127.4 . . ?
C1 N2 C2 105.2(5) . . ?
C2 N2 H2 127.4 . . ?
C5 N6 N5 103.6(4) . . ?
N6 N5 H5 123.5 . . ?
N6 N5 C3 113.1(5) . . ?
C3 N5 H5 123.5 . . ?
N8 N9 H9 124.2 . . ?
C7 N9 H9 124.2 . . ?
C7 N9 N8 111.6(5) . . ?
H10A N10 H10B 120.0 . . ?
C7 N10 H10A 120.0 . . ?
C7 N10 H10B 120.0 . . ?
C6 N8 N9 104.0(4) . . ?
N4 N3 H3 124.3 . . ?
C1 N3 H3 124.3 . . ?
C1 N3 N4 111.4(4) . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
C2 N4 N3 103.5(4) . . ?
H5A O5 H5B 104.5 . . ?
N3 C1 N2 106.5(5) . . ?
N1 C1 N2 126.7(5) . . ?
N1 C1 N3 126.8(5) . . ?
N7 C6 C5 122.6(5) . . ?
N8 C6 N7 111.0(5) . . ?
N8 C6 C5 126.4(5) . . ?
N5 C3 C4 107.1(5) . . ?
N5 C3 C2 121.1(5) . . ?
C4 C3 C2 131.7(5) . . ?
C3 C4 H4 128.1 . . ?
C3 C4 C5 103.9(5) . . ?
C5 C4 H4 128.1 . . ?
N2 C2 C3 122.2(5) . . ?
N4 C2 N2 113.4(5) . . ?
N4 C2 C3 124.5(5) . . ?
N9 C7 N7 106.1(5) . . ?
N10 C7 N7 126.0(5) . . ?
N10 C7 N9 127.8(5) . . ?
N6 C5 C6 120.1(5) . . ?
N6 C5 C4 112.3(5) . . ?
C4 C5 C6 127.7(5) . . ?
H6A O6 H6B 117.0 . . ?

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
N7 C6 C5 N6 1.2(8) . . . . ?
N7 C6 C5 C4 -179.6(5) . . . . ?
N6 N5 C3 C4 -0.8(6) . . . . ?
N6 N5 C3 C2 -178.8(5) . . . . ?
N5 N6 C5 C6 179.1(5) . . . . ?
N5 N6 C5 C4 -0.1(6) . . . . ?
N5 C3 C4 C5 0.6(6) . . . . ?
N5 C3 C2 N2 178.5(5) . . . . ?
N5 C3 C2 N4 -1.9(8) . . . . ?
N9 N8 C6 N7 2.2(6) . . . . ?
N9 N8 C6 C5 -177.6(5) . . . . ?
N8 N9 C7 N7 1.8(6) . . . . ?
N8 N9 C7 N10 -178.5(5) . . . . ?
N8 C6 C5 N6 -178.9(5) . . . . ?
N8 C6 C5 C4 0.2(9) . . . . ?
N3 N4 C2 N2 -0.4(6) . . . . ?
N3 N4 C2 C3 180.0(5) . . . . ?
N4 N3 C1 N2 1.7(6) . . . . ?
N4 N3 C1 N1 -179.0(5) . . . . ?
C1 N2 C2 N4 1.4(6) . . . . ?
C1 N2 C2 C3 -178.9(5) . . . . ?
C1 N3 N4 C2 -0.9(6) . . . . ?
C6 N7 C7 N9 -0.4(5) . . . . ?
C6 N7 C7 N10 179.9(5) . . . . ?
C3 C4 C5 N6 -0.3(6) . . . . ?
C3 C4 C5 C6 -179.5(5) . . . . ?
C4 C3 C2 N2 1.1(9) . . . . ?
C4 C3 C2 N4 -179.3(6) . . . . ?
C2 N2 C1 N3 -1.9(6) . . . . ?
C2 N2 C1 N1 178.8(5) . . . . ?
C2 C3 C4 C5 178.3(6) . . . . ?
C7 N7 C6 N8 -1.2(6) . . . . ?
C7 N7 C6 C5 178.6(5) . . . . ?
C7 N9 N8 C6 -2.5(6) . . . . ?
C5 N6 N5 C3 0.6(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.796(3)
2 0.204(3)

