# 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 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_exp_8893
_audit_block_doi                 10.5517/ccdc.csd.cc2j1hmq
_database_code_depnum_ccdc_archive 'CCDC 2325143'
loop_
_audit_author_name
_audit_author_address
'Baolong Kuang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2024-01-12 deposited with the CCDC.	2024-03-25 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_exp_8893            
;
PROBLEM: Short Inter D...A Contact  O10      ..O10      .       2.77 Ang.
RESPONSE: There is no H-bond between O10 and O10 in deed, and the distance between O10 and O10 of 2.77 Ang. is reasonable.
;
# Added during the CSD deposition process: Friday 12 January 2024 12:15 PM
# end Validation Reply Form

_audit_creation_date             2024-01-11
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H16 Cu N8 O8, 2(Cl O4)'
_chemical_formula_sum            'C12 H16 Cl2 Cu N8 O16'
_chemical_formula_weight         662.77
_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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   10.1057(8)
_cell_length_b                   15.7064(10)
_cell_length_c                   14.8468(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.467(7)
_cell_angle_gamma                90.00
_cell_volume                     2271.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1427
_cell_measurement_temperature    115.30(10)
_cell_measurement_theta_max      24.7270
_cell_measurement_theta_min      3.9470
_exptl_absorpt_coefficient_mu    1.296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.938
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1340
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_unetI/netI     0.1112
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10376
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.96
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      115.30(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9972
_diffrn_measured_fraction_theta_max 0.8223
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   16.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852   57.0000  -30.0000 61

#__ type_ start__ end____ width___ exp.time_
  2 omega   15.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852   37.0000  -90.0000 70

#__ type_ start__ end____ width___ exp.time_
  3 omega   -5.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -57.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -19.00    7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.8508  -99.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   -3.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -99.0000  120.0000 49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0605432000
_diffrn_orient_matrix_UB_12      0.0249391000
_diffrn_orient_matrix_UB_13      -0.0077298000
_diffrn_orient_matrix_UB_21      0.0210212000
_diffrn_orient_matrix_UB_22      0.0240647000
_diffrn_orient_matrix_UB_23      -0.0342233000
_diffrn_orient_matrix_UB_31      -0.0346216000
_diffrn_orient_matrix_UB_32      -0.0289662000
_diffrn_orient_matrix_UB_33      -0.0350666000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2786
_reflns_number_total             4360
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.792
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4360
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0556
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0227P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.1129
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.78270(5) 0.11338(4) 0.76357(3) 0.01791(18) Uani 1 1 d . . .
Cl2 Cl 0.45798(12) -0.11381(8) 0.59316(7) 0.0211(3) Uani 1 1 d . . .
O2 O 0.9615(3) 0.1573(2) 0.75724(19) 0.0166(8) Uani 1 1 d . . .
O1 O 0.5991(3) 0.0763(2) 0.76778(19) 0.0172(8) Uani 1 1 d . . .
O4 O 0.5854(3) 0.3257(2) 0.5744(2) 0.0223(8) Uani 1 1 d . . .
O3 O 0.6513(3) 0.2276(2) 0.67925(19) 0.0204(8) Uani 1 1 d . . .
N2 N 0.6618(4) 0.1433(3) 0.9079(2) 0.0197(10) Uani 1 1 d . . .
H2 H 0.6474 0.1543 0.9612 0.024 Uiso 1 1 calc R . .
O6 O 0.9172(3) 0.0000(2) 0.8460(2) 0.0249(9) Uani 1 1 d . . .
N7 N 0.6764(4) 0.2726(3) 0.6158(2) 0.0206(10) Uani 1 1 d . . .
N5 N 0.9064(3) 0.0861(3) 0.6201(2) 0.0175(9) Uani 1 1 d . . .
H5 H 0.9257 0.0714 0.5692 0.021 Uiso 1 1 calc R . .
N3 N 0.7821(3) 0.1710(3) 0.8843(2) 0.0178(9) Uani 1 1 d . . .
H3A H 0.8575 0.1564 0.9295 0.021 Uiso 1 1 calc R . .
H3B H 0.7811 0.2279 0.8774 0.021 Uiso 1 1 calc R . .
O5 O 0.7848(3) 0.2666(3) 0.5928(2) 0.0292(9) Uani 1 1 d . . .
O7 O 0.7677(3) -0.0526(3) 0.9111(2) 0.0328(10) Uani 1 1 d . . .
N8 N 0.8871(4) -0.0485(3) 0.9065(2) 0.0225(10) Uani 1 1 d . . .
N6 N 0.7857(3) 0.0577(3) 0.6421(2) 0.0174(9) Uani 1 1 d . . .
H6A H 0.7867 0.0006 0.6480 0.021 Uiso 1 1 calc R . .
H6B H 0.7109 0.0726 0.5966 0.021 Uiso 1 1 calc R . .
C9 C 1.2019(4) 0.1093(3) 0.6292(3) 0.0195(12) Uani 1 1 d . . .
H9 H 1.1710 0.0548 0.6098 0.023 Uiso 1 1 calc R . .
C7 C 0.9880(4) 0.1365(3) 0.6825(3) 0.0168(11) Uani 1 1 d . . .
C8 C 1.1212(4) 0.1646(3) 0.6652(3) 0.0152(11) Uani 1 1 d . . .
C3 C 0.3663(4) 0.1365(4) 0.8971(3) 0.0219(12) Uani 1 1 d . . .
H3 H 0.4049 0.1890 0.9180 0.026 Uiso 1 1 calc R . .
O8 O 0.9813(3) -0.0906(2) 0.9595(2) 0.0345(10) Uani 1 1 d . . .
C2 C 0.4381(4) 0.0777(3) 0.8587(3) 0.0184(11) Uani 1 1 d . . .
N4 N 1.3689(4) 0.2162(3) 0.6520(3) 0.0266(11) Uani 1 1 d . . .
H4 H 1.4484 0.2325 0.6479 0.032 Uiso 1 1 calc R . .
C4 C 0.2369(5) 0.1157(4) 0.9037(3) 0.0266(13) Uani 1 1 d . . .
H4A H 0.1868 0.1540 0.9292 0.032 Uiso 1 1 calc R . .
C12 C 1.1668(5) 0.2464(3) 0.6934(3) 0.0209(12) Uani 1 1 d . . .
H12 H 1.1124 0.2837 0.7166 0.025 Uiso 1 1 calc R . .
C6 C 0.3793(5) -0.0014(3) 0.8252(3) 0.0218(12) Uani 1 1 d . . .
H6 H 0.4260 -0.0405 0.7980 0.026 Uiso 1 1 calc R . .
C1 C 0.5734(4) 0.0995(3) 0.8427(3) 0.0181(11) Uani 1 1 d . . .
N1 N 0.1839(4) 0.0391(3) 0.8726(2) 0.0240(10) Uani 1 1 d . . .
H1 H 0.1034 0.0266 0.8778 0.029 Uiso 1 1 calc R . .
C10 C 1.3267(5) 0.1367(4) 0.6233(3) 0.0205(12) Uani 1 1 d . . .
H10 H 1.3828 0.1010 0.5996 0.025 Uiso 1 1 calc R . .
C11 C 1.2936(5) 0.2706(4) 0.6862(3) 0.0284(14) Uani 1 1 d . . .
H11 H 1.3270 0.3247 0.7051 0.034 Uiso 1 1 calc R . .
C5 C 0.2494(5) -0.0182(4) 0.8344(3) 0.0276(13) Uani 1 1 d . . .
H5A H 0.2075 -0.0699 0.8137 0.033 Uiso 1 1 calc R . .
Cl1 Cl 1.00540(12) 0.35488(8) 0.89025(8) 0.0229(3) Uani 1 1 d . . .
O10 O 0.9828(3) 0.4270(2) 0.94551(19) 0.0231(8) Uani 1 1 d . . .
O12 O 0.8829(4) 0.3381(3) 0.8182(2) 0.0523(13) Uani 1 1 d . . .
O9 O 1.0385(4) 0.2812(2) 0.9485(2) 0.0384(10) Uani 1 1 d . . .
O11 O 1.1144(5) 0.3751(3) 0.8514(3) 0.0844(18) Uani 1 1 d . . .
O13 O 0.5802(4) -0.0718(3) 0.6419(2) 0.0498(12) Uani 1 1 d . . .
O14 O 0.4320(4) -0.1821(3) 0.6494(3) 0.0541(13) Uani 1 1 d . . .
O16 O 0.4700(4) -0.1462(3) 0.5061(2) 0.0651(15) Uani 1 1 d . . .
O15 O 0.3439(4) -0.0569(3) 0.5737(3) 0.0543(13) Uani 1 1 d . . .


_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
Cu1 O2 1.960(3) . ?
Cu1 O1 1.962(3) . ?
Cu1 O3 2.379(3) . ?
Cu1 O6 2.373(3) . ?
Cu1 N3 2.009(3) . ?
Cu1 N6 2.012(3) . ?
Cl2 O13 1.417(3) . ?
Cl2 O14 1.426(4) . ?
Cl2 O16 1.425(4) . ?
Cl2 O15 1.426(4) . ?
O2 C7 1.253(5) . ?
O1 C1 1.262(5) . ?
O4 N7 1.271(5) . ?
O3 N7 1.257(5) . ?
N2 H2 0.8600 . ?
N2 N3 1.420(5) . ?
N2 C1 1.321(5) . ?
O6 N8 1.275(5) . ?
N7 O5 1.235(5) . ?
N5 H5 0.8600 . ?
N5 N6 1.416(5) . ?
N5 C7 1.327(5) . ?
N3 H3A 0.9000 . ?
N3 H3B 0.9000 . ?
O7 N8 1.228(5) . ?
N8 O8 1.249(5) . ?
N6 H6A 0.9000 . ?
N6 H6B 0.9000 . ?
C9 H9 0.9300 . ?
C9 C8 1.392(6) . ?
C9 C10 1.358(6) . ?
C7 C8 1.502(6) . ?
C8 C12 1.390(7) . ?
C3 H3 0.9300 . ?
C3 C2 1.387(6) . ?
C3 C4 1.376(6) . ?
C2 C6 1.409(7) . ?
C2 C1 1.489(6) . ?
N4 H4 0.8600 . ?
N4 C10 1.351(6) . ?
N4 C11 1.332(7) . ?
C4 H4A 0.9300 . ?
C4 N1 1.346(7) . ?
C12 H12 0.9300 . ?
C12 C11 1.368(6) . ?
C6 H6 0.9300 . ?
C6 C5 1.381(6) . ?
N1 H1 0.8600 . ?
N1 C5 1.331(6) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C5 H5A 0.9300 . ?
Cl1 O10 1.452(3) . ?
Cl1 O12 1.428(3) . ?
Cl1 O9 1.431(4) . ?
Cl1 O11 1.409(4) . ?

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
O2 Cu1 O1 176.57(14) . . ?
O2 Cu1 O3 95.86(12) . . ?
O2 Cu1 O6 83.11(12) . . ?
O2 Cu1 N3 96.11(13) . . ?
O2 Cu1 N6 82.85(13) . . ?
O1 Cu1 O3 80.84(12) . . ?
O1 Cu1 O6 100.19(12) . . ?
O1 Cu1 N3 82.97(13) . . ?
O1 Cu1 N6 98.04(13) . . ?
O6 Cu1 O3 178.85(11) . . ?
N3 Cu1 O3 89.78(13) . . ?
N3 Cu1 O6 90.86(13) . . ?
N3 Cu1 N6 178.81(16) . . ?
N6 Cu1 O3 89.76(13) . . ?
N6 Cu1 O6 89.58(13) . . ?
O13 Cl2 O14 108.9(2) . . ?
O13 Cl2 O16 110.8(2) . . ?
O13 Cl2 O15 111.0(3) . . ?
O14 Cl2 O15 109.0(3) . . ?
O16 Cl2 O14 109.7(3) . . ?
O16 Cl2 O15 107.4(3) . . ?
C7 O2 Cu1 111.6(3) . . ?
C1 O1 Cu1 111.2(3) . . ?
N7 O3 Cu1 128.5(3) . . ?
N3 N2 H2 122.1 . . ?
C1 N2 H2 122.1 . . ?
C1 N2 N3 115.8(4) . . ?
N8 O6 Cu1 126.9(3) . . ?
O3 N7 O4 117.8(4) . . ?
O5 N7 O4 119.8(4) . . ?
O5 N7 O3 122.4(4) . . ?
N6 N5 H5 121.9 . . ?
C7 N5 H5 121.9 . . ?
C7 N5 N6 116.1(4) . . ?
Cu1 N3 H3A 110.4 . . ?
Cu1 N3 H3B 110.4 . . ?
N2 N3 Cu1 106.7(2) . . ?
N2 N3 H3A 110.4 . . ?
N2 N3 H3B 110.4 . . ?
H3A N3 H3B 108.6 . . ?
O7 N8 O6 119.5(4) . . ?
O7 N8 O8 122.2(4) . . ?
O8 N8 O6 118.3(4) . . ?
Cu1 N6 H6A 110.4 . . ?
Cu1 N6 H6B 110.4 . . ?
N5 N6 Cu1 106.8(2) . . ?
N5 N6 H6A 110.4 . . ?
N5 N6 H6B 110.4 . . ?
H6A N6 H6B 108.6 . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C10 C9 C8 118.4(5) . . ?
O2 C7 N5 122.3(4) . . ?
O2 C7 C8 119.2(4) . . ?
N5 C7 C8 118.4(4) . . ?
C9 C8 C7 121.7(5) . . ?
C12 C8 C9 120.7(4) . . ?
C12 C8 C7 117.4(4) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C4 C3 C2 118.8(5) . . ?
C3 C2 C6 121.0(5) . . ?
C3 C2 C1 121.0(5) . . ?
C6 C2 C1 117.7(4) . . ?
C10 N4 H4 118.4 . . ?
C11 N4 H4 118.4 . . ?
C11 N4 C10 123.3(4) . . ?
C3 C4 H4A 120.4 . . ?
N1 C4 C3 119.1(5) . . ?
N1 C4 H4A 120.4 . . ?
C8 C12 H12 120.8 . . ?
C11 C12 C8 118.4(5) . . ?
C11 C12 H12 120.8 . . ?
C2 C6 H6 121.5 . . ?
C5 C6 C2 117.1(5) . . ?
C5 C6 H6 121.5 . . ?
O1 C1 N2 122.5(4) . . ?
O1 C1 C2 119.2(4) . . ?
N2 C1 C2 118.3(4) . . ?
C4 N1 H1 118.2 . . ?
C5 N1 C4 123.5(5) . . ?
C5 N1 H1 118.2 . . ?
C9 C10 H10 120.2 . . ?
N4 C10 C9 119.5(5) . . ?
N4 C10 H10 120.2 . . ?
N4 C11 C12 119.6(5) . . ?
N4 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C6 C5 H5A 119.8 . . ?
N1 C5 C6 120.5(5) . . ?
N1 C5 H5A 119.8 . . ?
O12 Cl1 O10 109.4(2) . . ?
O12 Cl1 O9 108.6(2) . . ?
O9 Cl1 O10 109.7(2) . . ?
O11 Cl1 O10 108.3(2) . . ?
O11 Cl1 O12 110.5(3) . . ?
O11 Cl1 O9 110.3(3) . . ?

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
Cu1 O2 C7 N5 -4.3(5) . . . . ?
Cu1 O2 C7 C8 180.0(3) . . . . ?
Cu1 O1 C1 N2 0.1(6) . . . . ?
Cu1 O1 C1 C2 179.6(3) . . . . ?
Cu1 O3 N7 O4 173.9(3) . . . . ?
Cu1 O3 N7 O5 -5.7(6) . . . . ?
Cu1 O6 N8 O7 17.4(6) . . . . ?
Cu1 O6 N8 O8 -162.7(3) . . . . ?
O2 Cu1 O1 C1 -79(2) . . . . ?
O2 Cu1 O3 N7 30.5(3) . . . . ?
O2 Cu1 O6 N8 153.8(3) . . . . ?
O2 Cu1 N3 N2 -176.1(3) . . . . ?
O2 Cu1 N6 N5 -3.7(3) . . . . ?
O2 C7 C8 C9 135.7(4) . . . . ?
O2 C7 C8 C12 -39.3(6) . . . . ?
O1 Cu1 O2 C7 -101(2) . . . . ?
O1 Cu1 O3 N7 -150.5(3) . . . . ?
O1 Cu1 O6 N8 -25.3(3) . . . . ?
O1 Cu1 N3 N2 7.2(3) . . . . ?
O1 Cu1 N6 N5 172.9(3) . . . . ?
O3 Cu1 O2 C7 -84.6(3) . . . . ?
O3 Cu1 O1 C1 -95.4(3) . . . . ?
O3 Cu1 O6 N8 -178(100) . . . . ?
O3 Cu1 N3 N2 88.0(3) . . . . ?
O3 Cu1 N6 N5 92.2(3) . . . . ?
O6 Cu1 O2 C7 94.8(3) . . . . ?
O6 Cu1 O1 C1 85.2(3) . . . . ?
O6 Cu1 O3 N7 3(6) . . . . ?
O6 Cu1 N3 N2 -92.9(3) . . . . ?
O6 Cu1 N6 N5 -86.9(3) . . . . ?
N5 C7 C8 C9 -40.2(6) . . . . ?
N5 C7 C8 C12 144.7(4) . . . . ?
N3 Cu1 O2 C7 -175.0(3) . . . . ?
N3 Cu1 O1 C1 -4.5(3) . . . . ?
N3 Cu1 O3 N7 126.6(3) . . . . ?
N3 Cu1 O6 N8 57.8(3) . . . . ?
N3 Cu1 N6 N5 25(7) . . . . ?
N3 N2 C1 O1 6.7(7) . . . . ?
N3 N2 C1 C2 -172.8(4) . . . . ?
N6 Cu1 O2 C7 4.4(3) . . . . ?
N6 Cu1 O1 C1 176.2(3) . . . . ?
N6 Cu1 O3 N7 -52.3(3) . . . . ?
N6 Cu1 O6 N8 -123.3(3) . . . . ?
N6 Cu1 N3 N2 155(7) . . . . ?
N6 N5 C7 O2 0.9(6) . . . . ?
N6 N5 C7 C8 176.7(4) . . . . ?
C9 C8 C12 C11 -1.0(6) . . . . ?
C7 N5 N6 Cu1 2.8(4) . . . . ?
C7 C8 C12 C11 174.2(4) . . . . ?
C8 C9 C10 N4 -0.1(6) . . . . ?
C8 C12 C11 N4 0.6(6) . . . . ?
C3 C2 C6 C5 -1.6(6) . . . . ?
C3 C2 C1 O1 -138.0(5) . . . . ?
C3 C2 C1 N2 41.5(6) . . . . ?
C3 C4 N1 C5 -0.8(7) . . . . ?
C2 C3 C4 N1 -0.1(6) . . . . ?
C2 C6 C5 N1 0.7(6) . . . . ?
C4 C3 C2 C6 1.3(7) . . . . ?
C4 C3 C2 C1 174.9(4) . . . . ?
C4 N1 C5 C6 0.5(7) . . . . ?
C6 C2 C1 O1 35.8(6) . . . . ?
C6 C2 C1 N2 -144.7(4) . . . . ?
C1 N2 N3 Cu1 -9.4(5) . . . . ?
C1 C2 C6 C5 -175.4(4) . . . . ?
C10 C9 C8 C7 -174.2(4) . . . . ?
C10 C9 C8 C12 0.7(6) . . . . ?
C10 N4 C11 C12 0.0(7) . . . . ?
C11 N4 C10 C9 -0.3(7) . . . . ?

####################################################################### 
# 
# 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_exp_8894
_audit_block_doi                 10.5517/ccdc.csd.cc2j3bkk
_database_code_depnum_ccdc_archive 'CCDC 2326908'
loop_
_audit_author_name
_audit_author_address
'Binshan Zhao'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2024-01-20 deposited with the CCDC.	2024-03-25 downloaded from the CCDC.
;
_audit_creation_date             2024-01-11
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(Cl O4), C6 H9 N3 O, H2 O'
_chemical_formula_sum            'C6 H11 Cl2 N3 O10'
_chemical_formula_weight         356.08
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.3108(10)
_cell_length_b                   8.3745(12)
_cell_length_c                   11.0926(16)
_cell_angle_alpha                82.288(12)
_cell_angle_beta                 89.995(11)
_cell_angle_gamma                74.587(12)
_cell_volume                     648.34(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1586
_cell_measurement_temperature    115.25(10)
_cell_measurement_theta_max      28.2960
_cell_measurement_theta_min      3.3610
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.824
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4505
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.35
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      115.25(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.8220
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    1.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2414   57.0000    0.0000 81

#__ type_ start__ end____ width___ exp.time_
  2 omega   49.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2414   57.0000  -90.0000 30

#__ type_ start__ end____ width___ exp.time_
  3 omega   13.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2414   57.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega   -3.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2414   37.0000 -180.0000 48

#__ type_ start__ end____ width___ exp.time_
  5 omega   -9.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2414   77.0000 -150.0000 88

#__ type_ start__ end____ width___ exp.time_
  6 omega    4.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2414   57.0000   90.0000 69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0309492000
_diffrn_orient_matrix_UB_12      0.0640188000
_diffrn_orient_matrix_UB_13      -0.0359452000
_diffrn_orient_matrix_UB_21      -0.0049407000
_diffrn_orient_matrix_UB_22      -0.0389729000
_diffrn_orient_matrix_UB_23      -0.0525066000
_diffrn_orient_matrix_UB_31      -0.0958739000
_diffrn_orient_matrix_UB_32      0.0476512000
_diffrn_orient_matrix_UB_33      -0.0113880000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2057
_reflns_number_total             2483
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.037(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2483
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0257P)²+0.3643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0847
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.19926(8) 0.99247(7) 0.17821(5) 0.01585(18) Uani 1 1 d . . .
Cl1 Cl -0.47862(8) 0.35390(8) 0.30757(5) 0.01816(18) Uani 1 1 d . . .
O1 O -0.0109(2) 0.5373(2) 0.13366(15) 0.0177(4) Uani 1 1 d . . .
N1 N 0.0456(3) 0.6398(2) 0.34150(17) 0.0155(5) Uani 1 1 d . . .
H1 H 0.1310 0.5738 0.3047 0.019 Uiso 1 1 calc R . .
O10 O -0.2858(2) 0.3105(2) 0.03746(15) 0.0186(4) Uani 1 1 d . . .
H10A H -0.2194 0.2433 -0.0069 0.022 Uiso 1 1 d R . .
H10B H -0.2291 0.2805 0.1070 0.022 Uiso 1 1 d R . .
O8 O 0.0931(2) 1.1656(2) 0.16485(16) 0.0221(4) Uani 1 1 d . . .
N2 N -0.3048(3) 0.7120(2) 0.10041(17) 0.0150(5) Uani 1 1 d . . .
H2 H -0.3948 0.7882 0.1252 0.018 Uiso 1 1 calc R . .
O5 O -0.2885(2) 0.3696(2) 0.29260(16) 0.0263(5) Uani 1 1 d . . .
C1 C -0.1422(3) 0.6433(3) 0.1664(2) 0.0141(5) Uani 1 1 d . . .
O7 O 0.2511(2) 0.9314(2) 0.30361(15) 0.0249(4) Uani 1 1 d . . .
N3 N -0.3209(3) 0.6533(2) -0.01198(17) 0.0152(4) Uani 1 1 d . . .
H3A H -0.2470 0.6921 -0.0655 0.018 Uiso 1 1 calc R . .
H3B H -0.4410 0.6888 -0.0399 0.018 Uiso 1 1 calc R . .
H3C H -0.2848 0.5420 -0.0011 0.018 Uiso 1 1 calc R . .
C2 C -0.1290(3) 0.7029(3) 0.2875(2) 0.0140(5) Uani 1 1 d . . .
C3 C -0.2664(3) 0.8095(3) 0.3444(2) 0.0185(6) Uani 1 1 d . . .
H3 H -0.3872 0.8549 0.3084 0.022 Uiso 1 1 calc R . .
C5 C -0.0432(4) 0.7800(3) 0.5099(2) 0.0196(6) Uani 1 1 d . . .
H5 H -0.0141 0.8044 0.5858 0.024 Uiso 1 1 calc R . .
O6 O 0.0858(2) 0.8958(2) 0.13153(16) 0.0222(4) Uani 1 1 d . . .
O3 O -0.6079(2) 0.4896(2) 0.22927(17) 0.0299(5) Uani 1 1 d . . .
O2 O -0.4912(3) 0.1997(2) 0.27169(19) 0.0380(5) Uani 1 1 d . . .
O4 O -0.5305(3) 0.3626(2) 0.43162(16) 0.0306(5) Uani 1 1 d . . .
O9 O 0.3689(2) 0.9793(2) 0.10750(15) 0.0200(4) Uani 1 1 d . . .
C6 C 0.0914(3) 0.6752(3) 0.4491(2) 0.0176(5) Uani 1 1 d . . .
H6 H 0.2136 0.6295 0.4829 0.021 Uiso 1 1 calc R . .
C4 C -0.2224(4) 0.8485(3) 0.4562(2) 0.0218(6) Uani 1 1 d . . .
H4 H -0.3141 0.9213 0.4955 0.026 Uiso 1 1 calc 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
Cl2 O8 1.4389(17) . ?
Cl2 O7 1.4305(18) . ?
Cl2 O6 1.4425(17) . ?
Cl2 O9 1.4544(17) . ?
Cl1 O5 1.4382(18) . ?
Cl1 O3 1.4502(18) . ?
Cl1 O2 1.4266(19) . ?
Cl1 O4 1.4335(18) . ?
O1 C1 1.215(3) . ?
N1 H1 0.8600 . ?
N1 C2 1.351(3) . ?
N1 C6 1.331(3) . ?
O10 H10A 0.8500 . ?
O10 H10B 0.8500 . ?
N2 H2 0.8600 . ?
N2 C1 1.343(3) . ?
N2 N3 1.416(3) . ?
C1 C2 1.506(3) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 H3C 0.8900 . ?
C2 C3 1.371(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(3) . ?
C5 C4 1.382(3) . ?
C6 H6 0.9300 . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O8 Cl2 O6 109.42(10) . . ?
O8 Cl2 O9 108.26(10) . . ?
O7 Cl2 O8 110.15(11) . . ?
O7 Cl2 O6 109.99(11) . . ?
O7 Cl2 O9 109.98(11) . . ?
O6 Cl2 O9 109.00(10) . . ?
O5 Cl1 O3 108.85(11) . . ?
O2 Cl1 O5 109.64(12) . . ?
O2 Cl1 O3 108.28(12) . . ?
O2 Cl1 O4 110.65(12) . . ?
O4 Cl1 O5 110.13(11) . . ?
O4 Cl1 O3 109.26(11) . . ?
C2 N1 H1 118.5 . . ?
C6 N1 H1 118.5 . . ?
C6 N1 C2 123.0(2) . . ?
H10A O10 H10B 103.8 . . ?
C1 N2 H2 121.6 . . ?
C1 N2 N3 116.85(18) . . ?
N3 N2 H2 121.6 . . ?
O1 C1 N2 123.5(2) . . ?
O1 C1 C2 120.1(2) . . ?
N2 C1 C2 116.4(2) . . ?
N2 N3 H3A 109.5 . . ?
N2 N3 H3B 109.5 . . ?
N2 N3 H3C 109.5 . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
N1 C2 C1 112.1(2) . . ?
N1 C2 C3 119.2(2) . . ?
C3 C2 C1 128.7(2) . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 118.9(2) . . ?
C4 C3 H3 120.5 . . ?
C6 C5 H5 120.6 . . ?
C6 C5 C4 118.8(2) . . ?
C4 C5 H5 120.6 . . ?
N1 C6 C5 119.5(2) . . ?
N1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.8 . . ?

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
O1 C1 C2 N1 7.0(3) . . . . ?
O1 C1 C2 C3 -173.9(2) . . . . ?
N1 C2 C3 C4 -0.5(4) . . . . ?
N2 C1 C2 N1 -173.7(2) . . . . ?
N2 C1 C2 C3 5.4(4) . . . . ?
C1 C2 C3 C4 -179.6(2) . . . . ?
N3 N2 C1 O1 1.1(3) . . . . ?
N3 N2 C1 C2 -178.18(19) . . . . ?
C2 N1 C6 C5 0.3(4) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C6 N1 C2 C1 179.8(2) . . . . ?
C6 N1 C2 C3 0.6(4) . . . . ?
C6 C5 C4 C3 1.3(4) . . . . ?
C4 C5 C6 N1 -1.2(4) . . . . ?

####################################################################### 
# 
# 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_exp_8898_twin1_hklf5
_database_code_depnum_ccdc_archive 'CCDC 2326909'
loop_
_audit_author_name
_audit_author_address
'Binshan Zhao' 'Beijing Institute of Technology'
_audit_update_record             
;
2024-01-20 deposited with the CCDC.	2024-03-25 downloaded from the CCDC.
;
_audit_creation_date             2024-01-11
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(Cl O4), H2 O, C6 H9 N3 O'
_chemical_formula_sum            'C6 H11 Cl2 N3 O10'
_chemical_formula_weight         356.08
_chemical_absolute_configuration ad
_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'

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

_cell_length_a                   4.9151(6)
_cell_length_b                   10.5757(16)
_cell_length_c                   12.470(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.788(16)
_cell_angle_gamma                90.00
_cell_volume                     645.93(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1546
_cell_measurement_temperature    115.45(10)
_cell_measurement_theta_max      26.1740
_cell_measurement_theta_min      3.7990
_exptl_absorpt_coefficient_mu    0.562
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.831
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3462
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.28
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      115.45(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.6286
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -45.00   45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  -19.0000   60.0000 90

#__ type_ start__ end____ width___ exp.time_
  2 omega  -12.00   27.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.8508  -99.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
  3 omega  -53.00  -27.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  -37.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   -7.00   27.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  -37.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega   41.00   88.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  178.0000  150.0000 47

#__ type_ start__ end____ width___ exp.time_
  6 omega   -2.00   70.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289   37.0000  -90.0000 72

#__ type_ start__ end____ width___ exp.time_
  7 omega  -12.00   40.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289   19.0000 -120.0000 52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0005425000
_diffrn_orient_matrix_UB_12      0.0593187000
_diffrn_orient_matrix_UB_13      -0.0267753000
_diffrn_orient_matrix_UB_21      -0.0545521000
_diffrn_orient_matrix_UB_22      -0.0292767000
_diffrn_orient_matrix_UB_23      -0.0483675000
_diffrn_orient_matrix_UB_31      -0.1344372000
_diffrn_orient_matrix_UB_32      0.0116122000
_diffrn_orient_matrix_UB_33      0.0146129000
loop_
_diffrn_oxdiff_twin_id
_diffrn_oxdiff_twin_ratio
_diffrn_oxdiff_twin_reflns_isolated
_diffrn_oxdiff_twin_reflns_overlapped
1 0.5310 1381 3460
2 0.4690 1355 3460

_diffrn_oxdiff_twin_integration_method simultaneous
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3044
_reflns_number_total             3462
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.49(8)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3462
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0510P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.0969
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.3811(2) -1.09885(10) -0.55665(9) 0.0219(3) Uani 1 1 d . . .
O4 O -0.2388(7) -1.1987(3) -0.6119(3) 0.0394(10) Uani 1 1 d . . .
O5 O -0.5112(6) -1.0183(3) -0.6370(3) 0.0267(8) Uani 1 1 d . . .
O2 O -0.1757(6) -1.0334(3) -0.4912(3) 0.0376(9) Uani 1 1 d . . .
O10 O -0.0237(7) -0.8117(3) -0.5998(2) 0.0205(7) Uani 1 1 d D . .
O3 O -0.5705(6) -1.1563(4) -0.4939(3) 0.0394(10) Uani 1 1 d . . .
Cl2 Cl -0.12540(18) -0.93177(10) -0.91053(8) 0.0145(2) Uani 1 1 d . . .
O1 O -0.1995(5) -0.6031(3) -0.7599(2) 0.0216(7) Uani 1 1 d . . .
O7 O -0.4132(5) -0.9320(3) -0.8917(2) 0.0178(6) Uani 1 1 d . . .
N3 N -0.5703(7) -0.7763(3) -0.7140(3) 0.0150(8) Uani 1 1 d . . .
H3A H -0.6913 -0.8045 -0.6681 0.018 Uiso 1 1 calc R . .
H3B H -0.3994 -0.7756 -0.6798 0.018 Uiso 1 1 calc R . .
H3C H -0.5737 -0.8284 -0.7722 0.018 Uiso 1 1 calc R . .
O9 O -0.0512(6) -0.8082(3) -0.9441(3) 0.0242(8) Uani 1 1 d . . .
C6 C -0.7246(8) -0.3747(4) -0.7379(4) 0.0161(10) Uani 1 1 d . . .
H6 H -0.8238 -0.4173 -0.6866 0.019 Uiso 1 1 calc R . .
N1 N -0.6338(7) -0.1918(3) -0.8350(3) 0.0187(9) Uani 1 1 d . . .
H1 H -0.6678 -0.1114 -0.8485 0.022 Uiso 1 1 calc R . .
C1 C -0.4408(8) -0.5722(4) -0.7655(3) 0.0148(10) Uani 1 1 d . . .
C5 C -0.7753(9) -0.2494(4) -0.7620(4) 0.0178(11) Uani 1 1 d . . .
H5 H -0.9097 -0.2042 -0.7271 0.021 Uiso 1 1 calc R . .
C3 C -0.3843(8) -0.3733(4) -0.8673(3) 0.0146(10) Uani 1 1 d . . .
H3 H -0.2491 -0.4156 -0.9041 0.018 Uiso 1 1 calc R . .
N2 N -0.6427(7) -0.6522(3) -0.7483(3) 0.0167(9) Uani 1 1 d . . .
H2 H -0.8147 -0.6286 -0.7580 0.020 Uiso 1 1 calc R . .
O6 O 0.0315(5) -0.9674(3) -0.8124(2) 0.0221(8) Uani 1 1 d . . .
O8 O -0.0792(5) -1.0225(3) -0.9929(2) 0.0204(7) Uani 1 1 d . . .
C2 C -0.5246(7) -0.4381(4) -0.7904(3) 0.0125(8) Uani 1 1 d . . .
C4 C -0.4439(9) -0.2487(4) -0.8889(4) 0.0181(11) Uani 1 1 d . . .
H4 H -0.3521 -0.2036 -0.9411 0.022 Uiso 1 1 calc R . .
H10A H -0.007(10) -0.760(3) -0.548(2) 0.027 Uiso 1 1 d D . .
H10B H -0.053(9) -0.8845(18) -0.574(3) 0.027 Uiso 1 1 d D . .


_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 O4 1.469(3) . ?
Cl1 O5 1.425(3) . ?
Cl1 O2 1.424(3) . ?
Cl1 O3 1.404(3) . ?
O10 H10A 0.847(10) . ?
O10 H10B 0.852(10) . ?
Cl2 O7 1.453(3) . ?
Cl2 O9 1.428(3) . ?
Cl2 O6 1.441(3) . ?
Cl2 O8 1.438(3) . ?
O1 C1 1.227(5) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
N3 N2 1.417(5) . ?
C6 H6 0.9500 . ?
C6 C5 1.378(6) . ?
C6 C2 1.396(6) . ?
N1 H1 0.8800 . ?
N1 C5 1.337(6) . ?
N1 C4 1.337(6) . ?
C1 N2 1.335(5) . ?
C1 C2 1.501(6) . ?
C5 H5 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.406(6) . ?
C3 C4 1.373(6) . ?
N2 H2 0.8800 . ?
C4 H4 0.9500 . ?

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
O5 Cl1 O4 107.7(2) . . ?
O2 Cl1 O4 106.0(2) . . ?
O2 Cl1 O5 111.6(2) . . ?
O3 Cl1 O4 108.3(2) . . ?
O3 Cl1 O5 111.76(19) . . ?
O3 Cl1 O2 111.3(2) . . ?
H10A O10 H10B 108(2) . . ?
O9 Cl2 O7 108.93(18) . . ?
O9 Cl2 O6 110.86(18) . . ?
O9 Cl2 O8 110.0(2) . . ?
O6 Cl2 O7 108.76(16) . . ?
O8 Cl2 O7 109.18(18) . . ?
O8 Cl2 O6 109.12(18) . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
N2 N3 H3A 109.5 . . ?
N2 N3 H3B 109.5 . . ?
N2 N3 H3C 109.5 . . ?
C5 C6 H6 120.6 . . ?
C5 C6 C2 118.8(4) . . ?
C2 C6 H6 120.6 . . ?
C5 N1 H1 117.9 . . ?
C5 N1 C4 124.2(4) . . ?
C4 N1 H1 117.9 . . ?
O1 C1 N2 123.4(4) . . ?
O1 C1 C2 120.7(4) . . ?
N2 C1 C2 115.9(3) . . ?
C6 C5 H5 120.3 . . ?
N1 C5 C6 119.4(4) . . ?
N1 C5 H5 120.3 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C4 C3 C2 119.5(4) . . ?
N3 N2 H2 121.2 . . ?
C1 N2 N3 117.7(3) . . ?
C1 N2 H2 121.2 . . ?
C6 C2 C1 123.2(4) . . ?
C6 C2 C3 119.4(4) . . ?
C3 C2 C1 117.3(4) . . ?
N1 C4 C3 118.7(4) . . ?
N1 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?

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
O1 C1 N2 N3 4.9(6) . . . . ?
O1 C1 C2 C6 -138.2(4) . . . . ?
O1 C1 C2 C3 39.0(5) . . . . ?
C5 C6 C2 C1 176.1(4) . . . . ?
C5 C6 C2 C3 -1.1(6) . . . . ?
C5 N1 C4 C3 -1.3(6) . . . . ?
N2 C1 C2 C6 40.5(6) . . . . ?
N2 C1 C2 C3 -142.2(4) . . . . ?
C2 C6 C5 N1 0.3(6) . . . . ?
C2 C1 N2 N3 -173.8(3) . . . . ?
C2 C3 C4 N1 0.5(6) . . . . ?
C4 N1 C5 C6 0.9(6) . . . . ?
C4 C3 C2 C6 0.6(6) . . . . ?
C4 C3 C2 C1 -176.7(4) . . . . ?

