# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2407244'
loop_
_audit_author_name
_audit_author_address
'Alexander Medvedev'
;Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-12-03 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C10 H18 N), 3(H2 O2), 2(Cl)'
_chemical_formula_sum            'C20 H42 Cl2 N2 O6'
_chemical_formula_weight         477.45

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           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   18.7063(9)
_cell_length_b                   6.3312(3)
_cell_length_c                   20.0829(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.413(2)
_cell_angle_gamma                90
_cell_volume                     2281.56(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3701
_cell_measurement_theta_min      2.629
_cell_measurement_theta_max      29.682

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.324
_shelx_estimated_absorpt_T_min   0.881
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8906
_exptl_absorpt_correction_T_max  0.9257
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33522
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_av_R_equivalents  0.0771
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.756
_diffrn_reflns_theta_max         28.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6053
_reflns_number_gt                4801
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0359P)²+0.9709P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6053
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1014
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.79215(2) 0.90386(6) 0.67331(2) 0.01452(10) Uani 1 1 d . . . . .
Cl2 Cl 0.45865(2) 0.53727(6) 0.57983(2) 0.01633(10) Uani 1 1 d . . . . .
O1 O 0.65655(7) 0.23784(19) 0.70850(6) 0.0166(3) Uani 1 1 d . . . . .
H1 H 0.6772(13) 0.152(4) 0.7383(12) 0.042(7) Uiso 1 1 d . . . . .
O2 O 0.65051(7) 0.41075(19) 0.75592(6) 0.0184(3) Uani 1 1 d . . . . .
H2 H 0.6505(13) 0.522(4) 0.7286(13) 0.041(7) Uiso 1 1 d . . . . .
O3 O 0.61770(7) 0.66177(19) 0.59297(6) 0.0164(2) Uani 1 1 d . . . . .
H3 H 0.5740(13) 0.617(3) 0.5882(11) 0.031(6) Uiso 1 1 d . . . . .
O4 O 0.63586(7) 0.75019(19) 0.66386(6) 0.0171(3) Uani 1 1 d . . . . .
H4 H 0.6763(14) 0.802(4) 0.6658(12) 0.043(7) Uiso 1 1 d . . . . .
O5 O 0.60839(8) 1.0007(2) 0.50208(7) 0.0209(3) Uani 1 1 d . . . . .
H5 H 0.6068(14) 0.899(4) 0.5290(13) 0.046(7) Uiso 1 1 d . . . . .
O6 O 0.59256(7) 1.1711(2) 0.54579(6) 0.0180(3) Uani 1 1 d . . . . .
H6 H 0.5731(14) 1.255(4) 0.5115(13) 0.048(7) Uiso 1 1 d . . . . .
N1 N 0.50300(8) 0.0779(2) 0.64563(7) 0.0136(3) Uani 1 1 d . . . . .
H11 H 0.4851(11) 0.185(3) 0.6219(10) 0.021(5) Uiso 1 1 d . . . . .
H12 H 0.4974(12) -0.036(3) 0.6172(11) 0.025(6) Uiso 1 1 d . . . . .
H13 H 0.5538(12) 0.095(3) 0.6645(11) 0.027(6) Uiso 1 1 d . . . . .
C11 C 0.46503(9) 0.0437(2) 0.70156(8) 0.0106(3) Uani 1 1 d . . . . .
C12 C 0.50075(9) -0.1468(2) 0.74510(8) 0.0128(3) Uani 1 1 d . . . . .
H121 H 0.554469 -0.120143 0.766704 0.015 Uiso 1 1 calc R U . . .
H122 H 0.495669 -0.273580 0.715282 0.015 Uiso 1 1 calc R U . . .
C13 C 0.46129(9) -0.1828(3) 0.80151(8) 0.0142(3) Uani 1 1 d . . . . .
H131 H 0.483837 -0.307730 0.830286 0.017 Uiso 1 1 calc R U . . .
C14 C 0.37823(9) -0.2239(2) 0.76753(8) 0.0145(3) Uani 1 1 d . . . . .
H141 H 0.372051 -0.351063 0.737771 0.017 Uiso 1 1 calc R U . . .
H142 H 0.352802 -0.249583 0.803835 0.017 Uiso 1 1 calc R U . . .
C15 C 0.34328(9) -0.0329(2) 0.72371(8) 0.0138(3) Uani 1 1 d . . . . .
H151 H 0.289058 -0.059995 0.701733 0.017 Uiso 1 1 calc R U . . .
C16 C 0.38231(9) 0.0034(3) 0.66687(8) 0.0132(3) Uani 1 1 d . . . . .
H161 H 0.376155 -0.122229 0.636441 0.016 Uiso 1 1 calc R U . . .
H162 H 0.359953 0.126457 0.638033 0.016 Uiso 1 1 calc R U . . .
C17 C 0.47448(9) 0.2417(2) 0.74669(8) 0.0137(3) Uani 1 1 d . . . . .
H171 H 0.452031 0.364864 0.717979 0.016 Uiso 1 1 calc R U . . .
H172 H 0.528090 0.270883 0.767913 0.016 Uiso 1 1 calc R U . . .
C18 C 0.43569(9) 0.2048(3) 0.80370(8) 0.0146(3) Uani 1 1 d . . . . .
H181 H 0.441733 0.332941 0.833903 0.018 Uiso 1 1 calc R U . . .
C19 C 0.35254(9) 0.1633(3) 0.77018(9) 0.0161(3) Uani 1 1 d . . . . .
H191 H 0.329498 0.287072 0.742133 0.019 Uiso 1 1 calc R U . . .
H192 H 0.327174 0.140718 0.806703 0.019 Uiso 1 1 calc R U . . .
C20 C 0.47082(10) 0.0134(3) 0.84795(8) 0.0167(3) Uani 1 1 d . . . . .
H201 H 0.524455 0.039989 0.870048 0.020 Uiso 1 1 calc R U . . .
H202 H 0.446343 -0.009710 0.885081 0.020 Uiso 1 1 calc R U . . .
N2 N 0.74422(8) 1.3551(2) 0.60252(7) 0.0136(3) Uani 1 1 d . . . . .
H21 H 0.6947(12) 1.342(3) 0.5850(11) 0.028(6) Uiso 1 1 d . . . . .
H22 H 0.7614(13) 1.230(4) 0.6228(12) 0.040(7) Uiso 1 1 d . . . . .
H23 H 0.7518(14) 1.461(4) 0.6349(13) 0.044(7) Uiso 1 1 d . . . . .
C21 C 0.78235(8) 1.4061(2) 0.54780(8) 0.0105(3) Uani 1 1 d . . . . .
C22 C 0.77186(9) 1.2201(2) 0.49743(8) 0.0124(3) Uani 1 1 d . . . . .
H221 H 0.718109 1.196375 0.475090 0.015 Uiso 1 1 calc R U . . .
H222 H 0.793032 1.090186 0.522849 0.015 Uiso 1 1 calc R U . . .
C23 C 0.81162(9) 1.2705(2) 0.44202(8) 0.0132(3) Uani 1 1 d . . . . .
H231 H 0.804967 1.149876 0.408664 0.016 Uiso 1 1 calc R U . . .
C24 C 0.89478(9) 1.3048(3) 0.47684(8) 0.0145(3) Uani 1 1 d . . . . .
H241 H 0.920531 1.336913 0.441208 0.017 Uiso 1 1 calc R U . . .
H242 H 0.916937 1.174758 0.501557 0.017 Uiso 1 1 calc R U . . .
C25 C 0.90507(9) 1.4885(2) 0.52833(8) 0.0137(3) Uani 1 1 d . . . . .
H251 H 0.959404 1.510558 0.551248 0.016 Uiso 1 1 calc R U . . .
C26 C 0.86506(9) 1.4399(2) 0.58372(8) 0.0125(3) Uani 1 1 d . . . . .
H261 H 0.886543 1.311331 0.609871 0.015 Uiso 1 1 calc R U . . .
H262 H 0.871615 1.558895 0.616873 0.015 Uiso 1 1 calc R U . . .
C27 C 0.74793(9) 1.6062(2) 0.50903(8) 0.0120(3) Uani 1 1 d . . . . .
H271 H 0.753457 1.725534 0.541953 0.014 Uiso 1 1 calc R U . . .
H272 H 0.694142 1.583969 0.486439 0.014 Uiso 1 1 calc R U . . .
C28 C 0.78835(9) 1.6564(2) 0.45399(8) 0.0135(3) Uani 1 1 d . . . . .
H281 H 0.766782 1.787614 0.428376 0.016 Uiso 1 1 calc R U . . .
C29 C 0.77768(10) 1.4712(3) 0.40275(8) 0.0151(3) Uani 1 1 d . . . . .
H291 H 0.723895 1.449198 0.380064 0.018 Uiso 1 1 calc R U . . .
H292 H 0.802296 1.503386 0.366300 0.018 Uiso 1 1 calc R U . . .
C30 C 0.87159(9) 1.6900(2) 0.48927(9) 0.0154(3) Uani 1 1 d . . . . .
H301 H 0.878453 1.809697 0.522186 0.018 Uiso 1 1 calc R U . . .
H302 H 0.897476 1.724419 0.453927 0.018 Uiso 1 1 calc R U . . .


_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
O1 O2 1.4762(16) . ?
O1 H1 0.82(2) . ?
O2 H2 0.89(2) . ?
O3 O4 1.4773(16) . ?
O3 H3 0.84(2) . ?
O4 H4 0.82(2) . ?
O5 O6 1.4727(16) . ?
O5 H5 0.85(3) . ?
O6 H6 0.87(3) . ?
N1 C11 1.505(2) . ?
N1 H11 0.84(2) . ?
N1 H12 0.90(2) . ?
N1 H13 0.92(2) . ?
C11 C17 1.528(2) . ?
C11 C12 1.528(2) . ?
C11 C16 1.528(2) . ?
C12 C13 1.534(2) . ?
C12 H121 0.9900 . ?
C12 H122 0.9900 . ?
C13 C14 1.532(2) . ?
C13 C20 1.533(2) . ?
C13 H131 1.0000 . ?
C14 C15 1.529(2) . ?
C14 H141 0.9900 . ?
C14 H142 0.9900 . ?
C15 C19 1.534(2) . ?
C15 C16 1.536(2) . ?
C15 H151 1.0000 . ?
C16 H161 0.9900 . ?
C16 H162 0.9900 . ?
C17 C18 1.537(2) . ?
C17 H171 0.9900 . ?
C17 H172 0.9900 . ?
C18 C19 1.533(2) . ?
C18 C20 1.536(2) . ?
C18 H181 1.0000 . ?
C19 H191 0.9900 . ?
C19 H192 0.9900 . ?
C20 H201 0.9900 . ?
C20 H202 0.9900 . ?
N2 C21 1.5045(19) . ?
N2 H21 0.90(2) . ?
N2 H22 0.91(2) . ?
N2 H23 0.92(3) . ?
C21 C26 1.526(2) . ?
C21 C22 1.528(2) . ?
C21 C27 1.531(2) . ?
C22 C23 1.536(2) . ?
C22 H221 0.9900 . ?
C22 H222 0.9900 . ?
C23 C24 1.530(2) . ?
C23 C29 1.535(2) . ?
C23 H231 1.0000 . ?
C24 C25 1.532(2) . ?
C24 H241 0.9900 . ?
C24 H242 0.9900 . ?
C25 C30 1.535(2) . ?
C25 C26 1.537(2) . ?
C25 H251 1.0000 . ?
C26 H261 0.9900 . ?
C26 H262 0.9900 . ?
C27 C28 1.538(2) . ?
C27 H271 0.9900 . ?
C27 H272 0.9900 . ?
C28 C30 1.532(2) . ?
C28 C29 1.535(2) . ?
C28 H281 1.0000 . ?
C29 H291 0.9900 . ?
C29 H292 0.9900 . ?
C30 H301 0.9900 . ?
C30 H302 0.9900 . ?

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 O1 H1 97.4(17) . . ?
O1 O2 H2 100.0(15) . . ?
O4 O3 H3 100.7(15) . . ?
O3 O4 H4 99.0(17) . . ?
O6 O5 H5 97.4(17) . . ?
O5 O6 H6 94.9(17) . . ?
C11 N1 H11 110.1(14) . . ?
C11 N1 H12 111.2(13) . . ?
H11 N1 H12 108.9(18) . . ?
C11 N1 H13 111.0(13) . . ?
H11 N1 H13 109.5(18) . . ?
H12 N1 H13 106.0(18) . . ?
N1 C11 C17 108.96(12) . . ?
N1 C11 C12 108.57(13) . . ?
C17 C11 C12 110.45(13) . . ?
N1 C11 C16 108.33(12) . . ?
C17 C11 C16 109.86(13) . . ?
C12 C11 C16 110.62(13) . . ?
C11 C12 C13 108.43(13) . . ?
C11 C12 H121 110.0 . . ?
C13 C12 H121 110.0 . . ?
C11 C12 H122 110.0 . . ?
C13 C12 H122 110.0 . . ?
H121 C12 H122 108.4 . . ?
C14 C13 C20 109.72(14) . . ?
C14 C13 C12 109.59(13) . . ?
C20 C13 C12 109.35(13) . . ?
C14 C13 H131 109.4 . . ?
C20 C13 H131 109.4 . . ?
C12 C13 H131 109.4 . . ?
C15 C14 C13 109.68(13) . . ?
C15 C14 H141 109.7 . . ?
C13 C14 H141 109.7 . . ?
C15 C14 H142 109.7 . . ?
C13 C14 H142 109.7 . . ?
H141 C14 H142 108.2 . . ?
C14 C15 C19 109.49(13) . . ?
C14 C15 C16 109.29(13) . . ?
C19 C15 C16 109.59(13) . . ?
C14 C15 H151 109.5 . . ?
C19 C15 H151 109.5 . . ?
C16 C15 H151 109.5 . . ?
C11 C16 C15 108.60(13) . . ?
C11 C16 H161 110.0 . . ?
C15 C16 H161 110.0 . . ?
C11 C16 H162 110.0 . . ?
C15 C16 H162 110.0 . . ?
H161 C16 H162 108.4 . . ?
C11 C17 C18 108.52(12) . . ?
C11 C17 H171 110.0 . . ?
C18 C17 H171 110.0 . . ?
C11 C17 H172 110.0 . . ?
C18 C17 H172 110.0 . . ?
H171 C17 H172 108.4 . . ?
C19 C18 C20 109.51(13) . . ?
C19 C18 C17 109.45(13) . . ?
C20 C18 C17 109.63(13) . . ?
C19 C18 H181 109.4 . . ?
C20 C18 H181 109.4 . . ?
C17 C18 H181 109.4 . . ?
C18 C19 C15 109.40(13) . . ?
C18 C19 H191 109.8 . . ?
C15 C19 H191 109.8 . . ?
C18 C19 H192 109.8 . . ?
C15 C19 H192 109.8 . . ?
H191 C19 H192 108.2 . . ?
C13 C20 C18 109.26(13) . . ?
C13 C20 H201 109.8 . . ?
C18 C20 H201 109.8 . . ?
C13 C20 H202 109.8 . . ?
C18 C20 H202 109.8 . . ?
H201 C20 H202 108.3 . . ?
C21 N2 H21 112.5(13) . . ?
C21 N2 H22 109.5(15) . . ?
H21 N2 H22 106.9(19) . . ?
C21 N2 H23 110.6(15) . . ?
H21 N2 H23 106.4(19) . . ?
H22 N2 H23 111(2) . . ?
N2 C21 C26 108.14(12) . . ?
N2 C21 C22 108.64(12) . . ?
C26 C21 C22 110.14(13) . . ?
N2 C21 C27 109.33(12) . . ?
C26 C21 C27 110.43(13) . . ?
C22 C21 C27 110.12(12) . . ?
C21 C22 C23 108.77(12) . . ?
C21 C22 H221 109.9 . . ?
C23 C22 H221 109.9 . . ?
C21 C22 H222 109.9 . . ?
C23 C22 H222 109.9 . . ?
H221 C22 H222 108.3 . . ?
C24 C23 C29 109.66(13) . . ?
C24 C23 C22 109.65(13) . . ?
C29 C23 C22 109.21(13) . . ?
C24 C23 H231 109.4 . . ?
C29 C23 H231 109.4 . . ?
C22 C23 H231 109.4 . . ?
C23 C24 C25 109.51(13) . . ?
C23 C24 H241 109.8 . . ?
C25 C24 H241 109.8 . . ?
C23 C24 H242 109.8 . . ?
C25 C24 H242 109.8 . . ?
H241 C24 H242 108.2 . . ?
C24 C25 C30 109.31(13) . . ?
C24 C25 C26 110.02(13) . . ?
C30 C25 C26 108.94(13) . . ?
C24 C25 H251 109.5 . . ?
C30 C25 H251 109.5 . . ?
C26 C25 H251 109.5 . . ?
C21 C26 C25 108.77(12) . . ?
C21 C26 H261 109.9 . . ?
C25 C26 H261 109.9 . . ?
C21 C26 H262 109.9 . . ?
C25 C26 H262 109.9 . . ?
H261 C26 H262 108.3 . . ?
C21 C27 C28 108.36(12) . . ?
C21 C27 H271 110.0 . . ?
C28 C27 H271 110.0 . . ?
C21 C27 H272 110.0 . . ?
C28 C27 H272 110.0 . . ?
H271 C27 H272 108.4 . . ?
C30 C28 C29 109.78(13) . . ?
C30 C28 C27 109.75(13) . . ?
C29 C28 C27 109.05(13) . . ?
C30 C28 H281 109.4 . . ?
C29 C28 H281 109.4 . . ?
C27 C28 H281 109.4 . . ?
C23 C29 C28 109.35(13) . . ?
C23 C29 H291 109.8 . . ?
C28 C29 H291 109.8 . . ?
C23 C29 H292 109.8 . . ?
C28 C29 H292 109.8 . . ?
H291 C29 H292 108.3 . . ?
C28 C30 C25 109.61(13) . . ?
C28 C30 H301 109.7 . . ?
C25 C30 H301 109.7 . . ?
C28 C30 H302 109.7 . . ?
C25 C30 H302 109.7 . . ?
H301 C30 H302 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C11 C12 C13 -179.34(12) . . . . ?
C17 C11 C12 C13 61.25(16) . . . . ?
C16 C11 C12 C13 -60.60(16) . . . . ?
C11 C12 C13 C14 59.68(16) . . . . ?
C11 C12 C13 C20 -60.63(16) . . . . ?
C20 C13 C14 C15 59.73(16) . . . . ?
C12 C13 C14 C15 -60.35(16) . . . . ?
C13 C14 C15 C19 -59.78(17) . . . . ?
C13 C14 C15 C16 60.26(16) . . . . ?
N1 C11 C16 C15 179.68(12) . . . . ?
C17 C11 C16 C15 -61.40(16) . . . . ?
C12 C11 C16 C15 60.80(16) . . . . ?
C14 C15 C16 C11 -59.87(16) . . . . ?
C19 C15 C16 C11 60.11(16) . . . . ?
N1 C11 C17 C18 -179.86(13) . . . . ?
C12 C11 C17 C18 -60.68(17) . . . . ?
C16 C11 C17 C18 61.61(16) . . . . ?
C11 C17 C18 C19 -60.52(16) . . . . ?
C11 C17 C18 C20 59.61(16) . . . . ?
C20 C18 C19 C15 -60.24(17) . . . . ?
C17 C18 C19 C15 59.97(17) . . . . ?
C14 C15 C19 C18 60.07(17) . . . . ?
C16 C15 C19 C18 -59.79(17) . . . . ?
C14 C13 C20 C18 -59.63(17) . . . . ?
C12 C13 C20 C18 60.59(17) . . . . ?
C19 C18 C20 C13 59.96(17) . . . . ?
C17 C18 C20 C13 -60.14(17) . . . . ?
N2 C21 C22 C23 -179.27(12) . . . . ?
C26 C21 C22 C23 -61.00(16) . . . . ?
C27 C21 C22 C23 61.03(16) . . . . ?
C21 C22 C23 C24 60.14(16) . . . . ?
C21 C22 C23 C29 -60.04(16) . . . . ?
C29 C23 C24 C25 60.33(16) . . . . ?
C22 C23 C24 C25 -59.58(16) . . . . ?
C23 C24 C25 C30 -60.28(16) . . . . ?
C23 C24 C25 C26 59.30(16) . . . . ?
N2 C21 C26 C25 179.08(12) . . . . ?
C22 C21 C26 C25 60.50(16) . . . . ?
C27 C21 C26 C25 -61.34(16) . . . . ?
C24 C25 C26 C21 -59.40(16) . . . . ?
C30 C25 C26 C21 60.41(16) . . . . ?
N2 C21 C27 C28 179.38(12) . . . . ?
C26 C21 C27 C28 60.52(16) . . . . ?
C22 C21 C27 C28 -61.33(16) . . . . ?
C21 C27 C28 C30 -59.50(16) . . . . ?
C21 C27 C28 C29 60.80(16) . . . . ?
C24 C23 C29 C28 -59.62(16) . . . . ?
C22 C23 C29 C28 60.55(17) . . . . ?
C30 C28 C29 C23 59.27(17) . . . . ?
C27 C28 C29 C23 -61.00(17) . . . . ?
C29 C28 C30 C25 -59.59(17) . . . . ?
C27 C28 C30 C25 60.26(16) . . . . ?
C24 C25 C30 C28 59.91(16) . . . . ?
C26 C25 C30 C28 -60.34(16) . . . . ?
H1 O1 O2 H2 153(2) . . . . ?
H3 O3 O4 H4 -175(2) . . . . ?
H5 O5 O6 H6 -153(2) . . . . ?

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
_geom_hbond_publ_flag
O1 H1 Cl1 0.82(2) 2.32(2) 3.1207(13) 166(2) 2_646 yes
O2 H2 O4 0.89(2) 1.91(2) 2.7974(17) 172(2) . yes
O3 H3 Cl2 0.84(2) 2.18(2) 3.0164(13) 174(2) . yes
O4 H4 Cl1 0.82(2) 2.22(2) 3.0359(13) 173(2) . yes
O5 H5 O3 0.85(3) 1.95(3) 2.7905(17) 172(2) . yes
O6 H6 Cl2 0.87(3) 2.20(3) 3.0537(13) 170(2) 3_676 yes
N1 H13 O1 0.92(2) 2.08(2) 2.9699(19) 160.8(18) . yes
N2 H21 O6 0.90(2) 2.14(2) 2.9794(19) 154.9(19) . yes
N1 H11 Cl2 0.84(2) 2.39(2) 3.2054(15) 164.2(18) . yes
N2 H22 Cl1 0.91(2) 2.30(3) 3.2043(15) 174(2) . yes

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_b
_database_code_depnum_ccdc_archive 'CCDC 2455698'
loop_
_audit_author_name
_audit_author_address
'Alexander Medvedev'
;Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Russia
;

_audit_update_record             
;
2025-06-01 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 H10 N2, 0.871(H2 O2), 0.129(H2 O), 2(Cl)'
_chemical_formula_sum            'C2 H12 Cl2 N2 O1.87'
_chemical_formula_weight         164.96

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.1837(4)
_cell_length_b                   5.9656(2)
_cell_length_c                   11.0793(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.9640(10)
_cell_angle_gamma                90
_cell_volume                     730.15(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4046
_cell_measurement_theta_min      3.689
_cell_measurement_theta_max      30.507

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.814
_shelx_estimated_absorpt_T_min   0.822
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7902
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5774
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.689
_diffrn_reflns_theta_max         30.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1098
_reflns_number_gt                995
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0130P)²+0.4926P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1098
_refine_ls_number_parameters     67
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0221
_refine_ls_wR_factor_ref         0.0598
_refine_ls_wR_factor_gt          0.0581
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_restrained_S_all      1.175
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.39947(2) 0.74526(4) 0.39620(2) 0.01213(9) Uani 1 1 d . . . . .
N1 N 0.16778(8) 0.43163(15) 0.37490(8) 0.01236(18) Uani 1 1 d . . . . .
H11 H 0.1008(15) 0.460(3) 0.4084(14) 0.031(4) Uiso 1 1 d . . . . .
H12 H 0.1445(13) 0.409(3) 0.2957(14) 0.024(4) Uiso 1 1 d . . . . .
H13 H 0.2165(14) 0.552(3) 0.3830(13) 0.024(4) Uiso 1 1 d . . . . .
C1 C 0.23462(10) 0.23343(16) 0.43149(10) 0.0123(2) Uani 1 1 d . . . . .
H21 H 0.1867(14) 0.105(3) 0.4118(13) 0.023(4) Uiso 1 1 d . . . . .
H22 H 0.3082(13) 0.216(2) 0.3936(13) 0.016(4) Uiso 1 1 d . . . . .
O1 O 0.52893(11) 0.31856(18) 0.31422(14) 0.0180(4) Uani 0.871(7) 1 d . . P A 1
H1 H 0.4908(18) 0.430(4) 0.3435(16) 0.030(5) Uiso 0.871(7) 1 d . . P A 1
O2 O 0.500000 0.3063(17) 0.250000 0.026(5) Uani 0.129(7) 2 d S T P A 2
H2 H 0.436740 0.362722 0.277050 0.039 Uiso 0.129(7) 1 d R U P A 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
N1 C1 1.4845(13) . ?
N1 H11 0.903(17) . ?
N1 H12 0.886(16) . ?
N1 H13 0.897(17) . ?
C1 C1 1.516(2) 7_556 ?
C1 H21 0.941(16) . ?
C1 H22 0.986(14) . ?
O1 O1 1.469(3) 2_655 ?
O1 H1 0.88(2) . ?
O1 H2 1.166(3) 2_655 ?
O2 H2 0.8774 . ?
O2 H2 0.8774 2_655 ?

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 H11 111.8(11) . . ?
C1 N1 H12 110.2(10) . . ?
H11 N1 H12 107.6(14) . . ?
C1 N1 H13 109.7(10) . . ?
H11 N1 H13 109.8(13) . . ?
H12 N1 H13 107.6(13) . . ?
N1 C1 C1 109.86(10) . 7_556 ?
N1 C1 H21 108.7(9) . . ?
C1 C1 H21 111.7(9) 7_556 . ?
N1 C1 H22 107.8(8) . . ?
C1 C1 H22 111.5(9) 7_556 . ?
H21 C1 H22 107.2(12) . . ?
O1 O1 H1 101.1(12) 2_655 . ?
O1 O1 H2 46.75(13) 2_655 2_655 ?
H1 O1 H2 113.3(13) . 2_655 ?
H2 O2 H2 134.9 . 2_655 ?
H1 O2 H2 48.4(9) 2_655 2_655 ?

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
H1 O1 O1 H1 79(2) . . 2_655 2_655 ?

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
_geom_hbond_publ_flag
O1^a H1^a Cl1 0.88(2) 2.26(2) 3.1322(12) 171.7(17) . yes
O2^b H2^b Cl1 0.88 2.70 3.364(8) 133.3 . yes
N1 H13 Cl1 0.897(17) 2.334(16) 3.1749(10) 156.2(13) . yes
N1 H11 Cl1 0.903(17) 2.576(17) 3.2429(10) 131.2(13) 3_445 yes
N1 H11 Cl1 0.903(17) 2.788(16) 3.3626(10) 122.6(12) 7_566 yes
N1 H12 Cl1 0.886(16) 2.321(16) 3.1812(10) 163.6(14) 4_545 yes

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.058




_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2455704'
loop_
_audit_author_name
_audit_author_address
'Alexander Medvedev'
;Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-06-01 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H14 N2, H2 O2, 2(Cl)'
_chemical_formula_sum            'C6 H16 Cl2 N2 O2'
_chemical_formula_weight         219.11

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   9.7834(6)
_cell_length_b                   9.3257(6)
_cell_length_c                   10.6627(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.935(2)
_cell_angle_gamma                90
_cell_volume                     961.03(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3104
_cell_measurement_theta_min      3.036
_cell_measurement_theta_max      30.507

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.641
_shelx_estimated_absorpt_T_min   0.784
_shelx_estimated_absorpt_T_max   0.883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8323
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6400
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.035
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1277
_reflns_number_gt                1132
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0231P)²+1.3180P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1277
_refine_ls_number_parameters     63
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0718
_refine_ls_wR_factor_gt          0.0683
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.21994(3) 0.55728(4) 0.49781(3) 0.01242(11) Uani 1 1 d . . . . .
O1 O -0.02413(14) 0.68835(18) 0.31033(11) 0.0355(4) Uani 1 1 d . . . . .
H1 H 0.042(3) 0.645(3) 0.359(2) 0.052(8) Uiso 1 1 d . . . . .
N1 N 0.41869(12) 0.68630(13) 0.32948(11) 0.0103(2) Uani 1 1 d . . . . .
H11 H 0.356(2) 0.681(2) 0.3870(18) 0.020(5) Uiso 1 1 d . . . . .
C1 C 0.43976(17) 0.53539(16) 0.28778(14) 0.0151(3) Uani 1 1 d . . . . .
H111 H 0.354767 0.499813 0.234229 0.018 Uiso 1 1 calc R U . . .
H112 H 0.460910 0.471855 0.362658 0.018 Uiso 1 1 calc R U . . .
C2 C 0.35886(15) 0.77531(17) 0.21693(14) 0.0146(3) Uani 1 1 d . . . . .
H211 H 0.361417 0.878162 0.240181 0.017 Uiso 1 1 calc R U . . .
H212 H 0.261391 0.747693 0.187793 0.017 Uiso 1 1 calc R U . . .
C3 C 0.55426(15) 0.74896(16) 0.38894(13) 0.0122(3) Uani 1 1 d . . . . .
H311 H 0.602935 0.681871 0.452725 0.015 Uiso 1 1 calc R U . . .
H312 H 0.538950 0.840297 0.431991 0.015 Uiso 1 1 calc R U . . .


_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
O1 O1 1.438(2) 2 ?
O1 H1 0.87(3) . ?
N1 C3 1.4972(18) . ?
N1 C1 1.4998(18) . ?
N1 C2 1.5012(18) . ?
N1 H11 0.93(2) . ?
C1 C1 1.527(3) 2_655 ?
C1 H111 0.9900 . ?
C1 H112 0.9900 . ?
C2 C3 1.535(2) 2_655 ?
C2 H211 0.9900 . ?
C2 H212 0.9900 . ?
C3 H311 0.9900 . ?
C3 H312 0.9900 . ?

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 O1 H1 102.5(17) 2 . ?
C3 N1 C1 109.77(11) . . ?
C3 N1 C2 109.42(11) . . ?
C1 N1 C2 109.66(11) . . ?
C3 N1 H11 111.7(12) . . ?
C1 N1 H11 106.3(12) . . ?
C2 N1 H11 109.9(12) . . ?
N1 C1 C1 108.01(8) . 2_655 ?
N1 C1 H111 110.1 . . ?
C1 C1 H111 110.1 2_655 . ?
N1 C1 H112 110.1 . . ?
C1 C1 H112 110.1 2_655 . ?
H111 C1 H112 108.4 . . ?
N1 C2 C3 107.92(11) . 2_655 ?
N1 C2 H211 110.1 . . ?
C3 C2 H211 110.1 2_655 . ?
N1 C2 H212 110.1 . . ?
C3 C2 H212 110.1 2_655 . ?
H211 C2 H212 108.4 . . ?
N1 C3 C2 107.85(11) . 2_655 ?
N1 C3 H311 110.1 . . ?
C2 C3 H311 110.1 2_655 . ?
N1 C3 H312 110.1 . . ?
C2 C3 H312 110.1 2_655 . ?
H311 C3 H312 108.5 . . ?

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
C3 N1 C1 C1 -49.04(18) . . . 2_655 ?
C2 N1 C1 C1 71.20(18) . . . 2_655 ?
C3 N1 C2 C3 71.56(13) . . . 2_655 ?
C1 N1 C2 C3 -48.88(15) . . . 2_655 ?
C1 N1 C3 C2 71.19(14) . . . 2_655 ?
C2 N1 C3 C2 -49.19(13) . . . 2_655 ?
H1 O1 O1 H1 123(4) . . 2 2 ?

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
_geom_hbond_publ_flag
O1 H1 Cl1 0.87(3) 2.25(3) 3.1160(14) 173(2) . yes
N1 H11 Cl1 0.93(2) 2.24(2) 3.0878(13) 151.7(17) . yes

_refine_diff_density_max         0.375
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_b_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2455700'
loop_
_audit_author_name
_audit_author_address
'Alexander Medvedev'
;Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-06-01 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H12 N2, H2 O2, 2(Cl)'
_chemical_formula_sum            'C4 H14 Cl2 N2 O2'
_chemical_formula_weight         193.07

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   10.7011(9)
_cell_length_b                   6.1485(7)
_cell_length_c                   13.6061(15)
_cell_angle_alpha                90
_cell_angle_beta                 111.074(3)
_cell_angle_gamma                90
_cell_volume                     835.35(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2049
_cell_measurement_theta_min      3.209
_cell_measurement_theta_max      30.518

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.725
_shelx_estimated_absorpt_T_min   0.760
_shelx_estimated_absorpt_T_max   0.812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8525
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4720
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.209
_diffrn_reflns_theta_max         28.988
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1120
_reflns_number_gt                980
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0169P)²+1.1053P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1120
_refine_ls_number_parameters     58
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0634
_refine_ls_wR_factor_gt          0.0586
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.55135(11) 0.5064(2) 0.72593(9) 0.0173(3) Uani 1 1 d . . . . .
H1 H 0.602(2) 0.401(4) 0.7578(19) 0.043(7) Uiso 1 1 d . . . . .
N1 N 0.54770(13) 0.9015(2) 0.60297(10) 0.0100(3) Uani 1 1 d . . . . .
H11 H 0.4983(18) 0.963(3) 0.6359(14) 0.013(4) Uiso 1 1 d . . . . .
H12 H 0.5996(19) 0.811(3) 0.6501(15) 0.022(5) Uiso 1 1 d . . . . .
C1 C 0.62960(15) 1.0672(2) 0.57304(12) 0.0106(3) Uani 1 1 d . . . . .
H111 H 0.691113 0.993521 0.544084 0.013 Uiso 1 1 calc R U . . .
H112 H 0.684292 1.150079 0.636259 0.013 Uiso 1 1 calc R U . . .
C2 C 0.46057(15) 0.7786(2) 0.50836(11) 0.0110(3) Uani 1 1 d . . . . .
H211 H 0.405263 0.672739 0.529553 0.013 Uiso 1 1 calc R U . . .
H212 H 0.517220 0.696807 0.477494 0.013 Uiso 1 1 calc R U . . .
Cl1 Cl 0.30426(3) 1.08617(6) 0.65728(3) 0.01142(11) 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
O1 O1 1.468(2) 2_656 ?
O1 H1 0.86(2) . ?
N1 C1 1.4929(19) . ?
N1 C2 1.4947(19) . ?
N1 H11 0.890(18) . ?
N1 H12 0.88(2) . ?
C1 C2 1.512(2) 5_676 ?
C1 H111 0.9900 . ?
C1 H112 0.9900 . ?
C2 H211 0.9900 . ?
C2 H212 0.9900 . ?

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 O1 H1 102.5(16) 2_656 . ?
C1 N1 C2 110.83(11) . . ?
C1 N1 H11 111.2(12) . . ?
C2 N1 H11 110.4(12) . . ?
C1 N1 H12 110.6(13) . . ?
C2 N1 H12 110.0(13) . . ?
H11 N1 H12 103.6(16) . . ?
N1 C1 C2 110.17(12) . 5_676 ?
N1 C1 H111 109.6 . . ?
C2 C1 H111 109.6 5_676 . ?
N1 C1 H112 109.6 . . ?
C2 C1 H112 109.6 5_676 . ?
H111 C1 H112 108.1 . . ?
N1 C2 C1 110.49(12) . 5_676 ?
N1 C2 H211 109.6 . . ?
C1 C2 H211 109.6 5_676 . ?
N1 C2 H212 109.6 . . ?
C1 C2 H212 109.6 5_676 . ?
H211 C2 H212 108.1 . . ?

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
H1 O1 O1 H1 -79(3) 2_656 2_656 . . ?

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
_geom_hbond_publ_flag
N1 H12 O1 0.88(2) 2.29(2) 2.9419(18) 131.4(16) . yes
O1 H1 Cl1 0.86(2) 2.29(3) 3.1342(13) 167(2) 2_646 yes
N1 H11 Cl1 0.890(18) 2.325(19) 3.1633(14) 156.9(16) . yes
N1 H12 Cl1 0.88(2) 2.56(2) 3.2223(14) 132.6(16) 3_545 yes

_refine_diff_density_max         0.478
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.071




_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2407245'
loop_
_audit_author_name
_audit_author_address
'Alexander Medvedev'
;Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-12-03 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C10 H18 N), H2 O2, 2(Cl)'
_chemical_formula_sum            'C20 H38 Cl2 N2 O2'
_chemical_formula_weight         409.42

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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7122(5)
_cell_length_b                   11.2178(9)
_cell_length_c                   14.5863(12)
_cell_angle_alpha                78.253(2)
_cell_angle_beta                 78.616(2)
_cell_angle_gamma                87.474(3)
_cell_volume                     1054.13(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7473
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      30.57

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.325
_shelx_estimated_absorpt_T_min   0.909
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8317
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12068
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.854
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5064
_reflns_number_gt                4473
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0537P)²+0.5815P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5064
_refine_ls_number_parameters     265
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.82381(6) 0.48422(3) 0.41167(3) 0.02161(11) Uani 1 1 d . . . . .
Cl2 Cl 0.39872(6) 0.91195(4) 0.41425(3) 0.02116(11) Uani 1 1 d . . . . .
O1 O 0.7127(2) 0.76813(13) 0.52273(9) 0.0319(3) Uani 1 1 d D . . . .
H1 H 0.613(3) 0.819(2) 0.4929(16) 0.048 Uiso 1 1 d D U . . .
O2 O 0.8647(2) 0.74746(13) 0.44093(10) 0.0327(3) Uani 1 1 d D . . . .
H2 H 0.849(4) 0.6554(19) 0.4532(17) 0.049 Uiso 1 1 d D U . . .
N1 N 0.4129(2) 0.64097(13) 0.38146(10) 0.0208(3) Uani 1 1 d D . . . .
H11 H 0.523(3) 0.603(2) 0.3945(17) 0.039(6) Uiso 1 1 d D . . . .
H12 H 0.308(3) 0.6027(18) 0.4188(14) 0.030(6) Uiso 1 1 d D . . . .
H13 H 0.408(4) 0.7168(16) 0.3927(17) 0.040(6) Uiso 1 1 d D . . . .
C1 C 0.4128(2) 0.64586(13) 0.27765(10) 0.0140(3) Uani 1 1 d . . . . .
C2 C 0.2276(2) 0.71831(13) 0.25046(11) 0.0159(3) Uani 1 1 d . . . . .
H2A H 0.231292 0.801744 0.262688 0.019 Uiso 1 1 calc R U . . .
H2B H 0.101333 0.678482 0.289304 0.019 Uiso 1 1 calc R U . . .
C3 C 0.2315(2) 0.72359(14) 0.14389(11) 0.0173(3) Uani 1 1 d . . . . .
H3 H 0.111132 0.770785 0.124979 0.021 Uiso 1 1 calc R U . . .
C4 C 0.2239(2) 0.59316(14) 0.12638(12) 0.0202(3) Uani 1 1 d . . . . .
H4A H 0.097353 0.552742 0.164374 0.024 Uiso 1 1 calc R U . . .
H4B H 0.224472 0.595742 0.058079 0.024 Uiso 1 1 calc R U . . .
C5 C 0.4091(2) 0.52106(13) 0.15529(11) 0.0176(3) Uani 1 1 d . . . . .
H5 H 0.404569 0.436434 0.143766 0.021 Uiso 1 1 calc R U . . .
C6 C 0.4042(2) 0.51594(13) 0.26169(11) 0.0177(3) Uani 1 1 d . . . . .
H6A H 0.277966 0.475799 0.300326 0.021 Uiso 1 1 calc R U . . .
H6B H 0.521630 0.468314 0.281498 0.021 Uiso 1 1 calc R U . . .
C7 C 0.6081(2) 0.70871(13) 0.21961(10) 0.0159(3) Uani 1 1 d . . . . .
H7A H 0.727641 0.662953 0.238801 0.019 Uiso 1 1 calc R U . . .
H7B H 0.613049 0.792200 0.231551 0.019 Uiso 1 1 calc R U . . .
C8 C 0.6123(2) 0.71379(13) 0.11310(10) 0.0163(3) Uani 1 1 d . . . . .
H8 H 0.739936 0.754501 0.074325 0.020 Uiso 1 1 calc R U . . .
C9 C 0.6053(2) 0.58344(14) 0.09597(11) 0.0185(3) Uani 1 1 d . . . . .
H9A H 0.609851 0.585667 0.027387 0.022 Uiso 1 1 calc R U . . .
H9B H 0.724693 0.536750 0.114443 0.022 Uiso 1 1 calc R U . . .
C10 C 0.4275(2) 0.78585(13) 0.08408(10) 0.0182(3) Uani 1 1 d . . . . .
H10A H 0.429763 0.789707 0.015469 0.022 Uiso 1 1 calc R U . . .
H10B H 0.432301 0.870111 0.094447 0.022 Uiso 1 1 calc R U . . .
N2 N 1.0678(2) 0.80050(14) 0.59071(10) 0.0208(3) Uani 1 1 d . . . . .
H21 H 1.167(4) 0.844(2) 0.5450(18) 0.042(6) Uiso 1 1 d . . . . .
H22 H 1.091(4) 0.720(2) 0.5927(18) 0.046(7) Uiso 1 1 d . . . . .
H23 H 0.945(4) 0.827(2) 0.5748(16) 0.034(6) Uiso 1 1 d . . . . .
C11 C 1.0662(2) 0.82858(13) 0.68712(10) 0.0153(3) Uani 1 1 d . . . . .
C12 C 1.2524(2) 0.76861(15) 0.72361(11) 0.0204(3) Uani 1 1 d . . . . .
H12A H 1.378087 0.801743 0.679451 0.024 Uiso 1 1 calc R U . . .
H12B H 1.249931 0.679681 0.726749 0.024 Uiso 1 1 calc R U . . .
C13 C 1.2499(2) 0.79427(14) 0.82336(11) 0.0198(3) Uani 1 1 d . . . . .
H4 H 1.370851 0.755073 0.847891 0.024 Uiso 1 1 calc R U . . .
C14 C 1.2566(2) 0.93177(15) 0.81712(12) 0.0216(3) Uani 1 1 d . . . . .
H14A H 1.382784 0.965613 0.773819 0.026 Uiso 1 1 calc R U . . .
H14B H 1.256059 0.949157 0.881038 0.026 Uiso 1 1 calc R U . . .
C15 C 1.0708(2) 0.99130(13) 0.77926(12) 0.0200(3) Uani 1 1 d . . . . .
H15 H 1.074919 1.081219 0.775367 0.024 Uiso 1 1 calc R U . . .
C16 C 1.0732(2) 0.96601(13) 0.67957(11) 0.0185(3) Uani 1 1 d . . . . .
H16A H 0.954337 1.005188 0.654673 0.022 Uiso 1 1 calc R U . . .
H16B H 1.198186 0.999773 0.635178 0.022 Uiso 1 1 calc R U . . .
C17 C 0.8721(2) 0.77575(14) 0.75389(11) 0.0176(3) Uani 1 1 d . . . . .
H17A H 0.867564 0.686844 0.757245 0.021 Uiso 1 1 calc R U . . .
H17B H 0.751776 0.813349 0.729371 0.021 Uiso 1 1 calc R U . . .
C18 C 0.8687(2) 0.80149(14) 0.85347(11) 0.0180(3) Uani 1 1 d . . . . .
H18 H 0.741694 0.767577 0.897728 0.022 Uiso 1 1 calc R U . . .
C19 C 1.0546(3) 0.74177(15) 0.89105(11) 0.0220(3) Uani 1 1 d . . . . .
H19A H 1.050902 0.652625 0.895491 0.026 Uiso 1 1 calc R U . . .
H19B H 1.052372 0.757266 0.955681 0.026 Uiso 1 1 calc R U . . .
C20 C 0.8752(2) 0.93965(15) 0.84685(12) 0.0217(3) Uani 1 1 d . . . . .
H20A H 0.755454 0.978595 0.822658 0.026 Uiso 1 1 calc R U . . .
H20B H 0.871174 0.957330 0.910983 0.026 Uiso 1 1 calc R U . . .


_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
O1 O2 1.4590(19) . ?
O1 H1 0.97(2) . ?
O2 H2 1.02(2) . ?
N1 C1 1.5040(19) . ?
N1 H11 0.869(16) . ?
N1 H12 0.869(16) . ?
N1 H13 0.896(16) . ?
C1 C7 1.527(2) . ?
C1 C6 1.527(2) . ?
C1 C2 1.529(2) . ?
C2 C3 1.539(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C10 1.536(2) . ?
C3 C4 1.540(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.535(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.535(2) . ?
C5 C9 1.535(2) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.538(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.534(2) . ?
C8 C9 1.537(2) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N2 C11 1.5004(19) . ?
N2 H21 0.92(3) . ?
N2 H22 0.91(3) . ?
N2 H23 0.92(2) . ?
C11 C16 1.525(2) . ?
C11 C17 1.526(2) . ?
C11 C12 1.530(2) . ?
C12 C13 1.536(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.529(2) . ?
C13 C19 1.536(2) . ?
C13 H4 1.0000 . ?
C14 C15 1.534(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.534(2) . ?
C15 C20 1.535(2) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.533(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.534(2) . ?
C18 C20 1.535(2) . ?
C18 H18 1.0000 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?

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 O1 H1 102.7(13) . . ?
O1 O2 H2 96.8(13) . . ?
C1 N1 H11 107.8(16) . . ?
C1 N1 H12 112.5(15) . . ?
H11 N1 H12 109(2) . . ?
C1 N1 H13 109.6(15) . . ?
H11 N1 H13 111(2) . . ?
H12 N1 H13 107(2) . . ?
N1 C1 C7 107.89(12) . . ?
N1 C1 C6 108.70(12) . . ?
C7 C1 C6 110.73(12) . . ?
N1 C1 C2 109.26(12) . . ?
C7 C1 C2 110.13(12) . . ?
C6 C1 C2 110.08(12) . . ?
C1 C2 C3 108.52(12) . . ?
C1 C2 H2A 110.0 . . ?
C3 C2 H2A 110.0 . . ?
C1 C2 H2B 110.0 . . ?
C3 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
C10 C3 C2 109.69(12) . . ?
C10 C3 C4 109.42(12) . . ?
C2 C3 C4 109.26(12) . . ?
C10 C3 H3 109.5 . . ?
C2 C3 H3 109.5 . . ?
C4 C3 H3 109.5 . . ?
C5 C4 C3 109.35(12) . . ?
C5 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
C5 C4 H4B 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
C6 C5 C9 109.61(12) . . ?
C6 C5 C4 109.21(13) . . ?
C9 C5 C4 109.77(12) . . ?
C6 C5 H5 109.4 . . ?
C9 C5 H5 109.4 . . ?
C4 C5 H5 109.4 . . ?
C1 C6 C5 108.59(12) . . ?
C1 C6 H6A 110.0 . . ?
C5 C6 H6A 110.0 . . ?
C1 C6 H6B 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
C1 C7 C8 108.84(12) . . ?
C1 C7 H7A 109.9 . . ?
C8 C7 H7A 109.9 . . ?
C1 C7 H7B 109.9 . . ?
C8 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C10 C8 C9 109.56(12) . . ?
C10 C8 C7 109.40(12) . . ?
C9 C8 C7 109.13(12) . . ?
C10 C8 H8 109.6 . . ?
C9 C8 H8 109.6 . . ?
C7 C8 H8 109.6 . . ?
C5 C9 C8 109.57(12) . . ?
C5 C9 H9A 109.8 . . ?
C8 C9 H9A 109.8 . . ?
C5 C9 H9B 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
C8 C10 C3 109.59(12) . . ?
C8 C10 H10A 109.8 . . ?
C3 C10 H10A 109.8 . . ?
C8 C10 H10B 109.8 . . ?
C3 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C11 N2 H21 111.0(15) . . ?
C11 N2 H22 109.6(16) . . ?
H21 N2 H22 109(2) . . ?
C11 N2 H23 106.6(14) . . ?
H21 N2 H23 107(2) . . ?
H22 N2 H23 114(2) . . ?
N2 C11 C16 109.87(12) . . ?
N2 C11 C17 108.02(12) . . ?
C16 C11 C17 110.52(13) . . ?
N2 C11 C12 108.48(12) . . ?
C16 C11 C12 109.87(12) . . ?
C17 C11 C12 110.04(12) . . ?
C11 C12 C13 108.98(12) . . ?
C11 C12 H12A 109.9 . . ?
C13 C12 H12A 109.9 . . ?
C11 C12 H12B 109.9 . . ?
C13 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C14 C13 C19 109.77(13) . . ?
C14 C13 C12 109.27(13) . . ?
C19 C13 C12 109.22(13) . . ?
C14 C13 H4 109.5 . . ?
C19 C13 H4 109.5 . . ?
C12 C13 H4 109.5 . . ?
C13 C14 C15 109.23(12) . . ?
C13 C14 H14A 109.8 . . ?
C15 C14 H14A 109.8 . . ?
C13 C14 H14B 109.8 . . ?
C15 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
C14 C15 C16 109.87(13) . . ?
C14 C15 C20 109.83(13) . . ?
C16 C15 C20 109.34(12) . . ?
C14 C15 H15 109.3 . . ?
C16 C15 H15 109.3 . . ?
C20 C15 H15 109.3 . . ?
C11 C16 C15 108.43(12) . . ?
C11 C16 H16A 110.0 . . ?
C15 C16 H16A 110.0 . . ?
C11 C16 H16B 110.0 . . ?
C15 C16 H16B 110.0 . . ?
H16A C16 H16B 108.4 . . ?
C11 C17 C18 108.96(12) . . ?
C11 C17 H17A 109.9 . . ?
C18 C17 H17A 109.9 . . ?
C11 C17 H17B 109.9 . . ?
C18 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
C17 C18 C19 109.39(13) . . ?
C17 C18 C20 109.12(12) . . ?
C19 C18 C20 109.49(13) . . ?
C17 C18 H18 109.6 . . ?
C19 C18 H18 109.6 . . ?
C20 C18 H18 109.6 . . ?
C18 C19 C13 109.65(12) . . ?
C18 C19 H19A 109.7 . . ?
C13 C19 H19A 109.7 . . ?
C18 C19 H19B 109.7 . . ?
C13 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
C15 C20 C18 109.47(12) . . ?
C15 C20 H20A 109.8 . . ?
C18 C20 H20A 109.8 . . ?
C15 C20 H20B 109.8 . . ?
C18 C20 H20B 109.8 . . ?
H20A C20 H20B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
H1 O1 O2 H2 -117(2) . . . . ?

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
_geom_hbond_publ_flag
O1 H1 Cl2 0.97(2) 2.12(2) 3.0863(14) 172(2) . yes
O2 H2 Cl1 1.02(2) 2.15(2) 3.0998(14) 154.3(19) . yes
N1 H11 Cl1 0.869(16) 2.399(16) 3.2606(15) 171(2) . yes
N1 H12 Cl1 0.869(16) 2.466(19) 3.1906(15) 141.3(18) 2_666 yes
N1 H13 Cl2 0.896(16) 2.271(16) 3.1665(15) 178(2) . yes
N2 H22 Cl1 0.91(3) 2.34(3) 3.2499(16) 175(2) 2_766 yes
N2 H23 O1 0.92(2) 2.05(2) 2.8199(19) 140.4(19) . yes
N2 H21 Cl2 0.92(3) 2.23(3) 3.1303(15) 165(2) 1_655 yes

_refine_diff_density_max         0.877
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_a_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2455699'
loop_
_audit_author_name
_audit_author_address
'Alexander Medvedev'
;Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-06-01 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H12 N2, 2(H2 O2), 2(Cl)'
_chemical_formula_sum            'C4 H16 Cl2 N2 O4'
_chemical_formula_weight         227.09

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.3636(4)
_cell_length_b                   11.0879(6)
_cell_length_c                   6.0534(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.808(2)
_cell_angle_gamma                90
_cell_volume                     487.02(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3561
_cell_measurement_theta_min      3.356
_cell_measurement_theta_max      30.469

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.649
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8197
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5409
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.355
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1287
_reflns_number_gt                1175
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0244P)²+0.1194P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1287
_refine_ls_number_parameters     87
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0197
_refine_ls_wR_factor_ref         0.0502
_refine_ls_wR_factor_gt          0.0491
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.25097(3) 0.36591(2) 0.11303(3) 0.01063(8) Uani 1 1 d . . . . .
O1 O 0.45613(10) 0.60453(7) 0.25481(12) 0.01448(16) Uani 1 1 d . . . . .
H1 H 0.401(2) 0.5415(14) 0.205(3) 0.032(4) Uiso 1 1 d . . . . .
O2 O 0.37715(10) 0.69243(7) 0.08551(13) 0.01599(16) Uani 1 1 d . . . . .
H2 H 0.460(2) 0.6989(13) 0.012(3) 0.032(4) Uiso 1 1 d . . . . .
N1 N 0.85256(11) 0.58029(7) 0.40979(13) 0.00849(16) Uani 1 1 d . . . . .
H3 H 0.8125(19) 0.6055(12) 0.529(2) 0.017(3) Uiso 1 1 d . . . . .
H4 H 0.788(2) 0.6154(12) 0.287(2) 0.022(3) Uiso 1 1 d . . . . .
C1 C 0.83038(13) 0.44669(8) 0.38537(16) 0.00971(18) Uani 1 1 d . . . . .
H11 H 0.8645(17) 0.4277(11) 0.243(2) 0.013(3) Uiso 1 1 d . . . . .
H12 H 0.7023(18) 0.4256(12) 0.387(2) 0.014(3) Uiso 1 1 d . . . . .
C2 C 1.04916(13) 0.61709(8) 0.42260(16) 0.00979(18) Uani 1 1 d . . . . .
H21 H 1.0811(17) 0.5964(10) 0.281(2) 0.010(3) Uiso 1 1 d . . . . .
H22 H 1.0569(17) 0.7053(11) 0.442(2) 0.015(3) Uiso 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
O1 O2 1.4613(10) . ?
O1 H1 0.837(16) . ?
O2 H2 0.820(16) . ?
N1 C2 1.4934(12) . ?
N1 C1 1.4948(12) . ?
N1 H3 0.868(14) . ?
N1 H4 0.897(15) . ?
C1 C2 1.5123(13) 3_766 ?
C1 H11 0.963(12) . ?
C1 H12 0.974(13) . ?
C2 H21 0.956(12) . ?
C2 H22 0.985(12) . ?

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 O1 H1 101.3(10) . . ?
O1 O2 H2 101.3(11) . . ?
C2 N1 C1 111.38(7) . . ?
C2 N1 H3 109.4(9) . . ?
C1 N1 H3 110.7(9) . . ?
C2 N1 H4 107.2(9) . . ?
C1 N1 H4 108.3(9) . . ?
H3 N1 H4 109.8(13) . . ?
N1 C1 C2 110.33(8) . 3_766 ?
N1 C1 H11 105.4(7) . . ?
C2 C1 H11 112.2(8) 3_766 . ?
N1 C1 H12 109.1(8) . . ?
C2 C1 H12 108.7(7) 3_766 . ?
H11 C1 H12 111.1(10) . . ?
N1 C2 C1 110.40(7) . 3_766 ?
N1 C2 H21 105.8(7) . . ?
C1 C2 H21 112.1(7) 3_766 . ?
N1 C2 H22 108.2(7) . . ?
C1 C2 H22 111.0(7) 3_766 . ?
H21 C2 H22 109.1(10) . . ?

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
C2 N1 C1 C2 57.02(11) . . . 3_766 ?
C1 N1 C2 C1 -57.06(11) . . . 3_766 ?
H1 O1 O2 H2 -102.0(15) . . . . ?

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
_geom_hbond_publ_flag
O1 H1 Cl1 0.837(16) 2.262(16) 3.0947(8) 173.4(14) . yes
O2 H2 Cl1 0.820(16) 2.481(16) 3.2377(8) 154.0(14) 3_665 yes
N1 H4 Cl1 0.897(15) 2.401(15) 3.1830(8) 145.8(12) 3_665 yes
N1 H3 Cl1 0.868(14) 2.318(14) 3.1672(8) 165.9(12) 3_666 yes

_refine_diff_density_max         0.446
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_a_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2407246'
loop_
_audit_author_name
_audit_author_address
'Alexander Medvedev'
;Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-12-03 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 H10 N2, H2 O2, 2(Cl)'
_chemical_formula_sum            'C2 H12 Cl2 N2 O2'
_chemical_formula_weight         167.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.231(2)
_cell_length_b                   5.9850(13)
_cell_length_c                   11.134(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.835(3)
_cell_angle_gamma                90
_cell_volume                     739.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1783
_cell_measurement_theta_min      3.672
_cell_measurement_theta_max      30.523

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   0.6221
_exptl_transmission_factor_max   0.7461
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.806
_shelx_estimated_absorpt_T_min   0.739
_shelx_estimated_absorpt_T_max   0.794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3160
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.672
_diffrn_reflns_theta_max         27.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             890
_reflns_number_gt                827
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0319P)²+0.2595P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.123(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         890
_refine_ls_number_parameters     62
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0669
_refine_ls_wR_factor_gt          0.0659
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.39813(3) 0.74466(4) 0.39466(3) 0.01842(17) Uani 1 1 d . . . . .
O1 O 0.52813(10) 0.31756(19) 0.31349(9) 0.0298(3) Uani 1 1 d . . . . .
N1 N 0.16725(9) 0.42968(18) 0.37581(10) 0.0181(3) Uani 1 1 d . . . . .
C1 C 0.23405(12) 0.23262(19) 0.43194(12) 0.0180(3) Uani 1 1 d . . . . .
H1 H 0.4876(19) 0.438(4) 0.3394(18) 0.056(6) Uiso 1 1 d . . . . .
H11 H 0.2135(15) 0.546(3) 0.3828(14) 0.027(4) Uiso 1 1 d . . . . .
H12 H 0.1009(16) 0.458(3) 0.4087(15) 0.032(4) Uiso 1 1 d . . . . .
H13 H 0.1445(14) 0.399(3) 0.2993(16) 0.033(4) Uiso 1 1 d . . . . .
H21 H 0.1831(16) 0.102(3) 0.4164(16) 0.038(5) Uiso 1 1 d . . . . .
H22 H 0.3077(17) 0.213(3) 0.3949(16) 0.027(4) Uiso 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
O1 O1 1.4572(19) 2_655 ?
O1 H1 0.92(2) . ?
N1 C1 1.4834(15) . ?
N1 H11 0.865(18) . ?
N1 H12 0.895(18) . ?
N1 H13 0.871(18) . ?
C1 C1 1.517(3) 7_556 ?
C1 H21 0.97(2) . ?
C1 H22 0.986(18) . ?

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 O1 H1 98.2(13) 2_655 . ?
C1 N1 H11 110.1(11) . . ?
C1 N1 H12 112.1(11) . . ?
H11 N1 H12 109.8(14) . . ?
C1 N1 H13 107.3(11) . . ?
H11 N1 H13 110.0(15) . . ?
H12 N1 H13 107.6(15) . . ?
N1 C1 C1 109.78(12) . 7_556 ?
N1 C1 H21 108.6(11) . . ?
C1 C1 H21 109.4(11) 7_556 . ?
N1 C1 H22 108.6(10) . . ?
C1 C1 H22 110.5(11) 7_556 . ?
H21 C1 H22 110.0(14) . . ?

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
H1 O1 O1 H1 76(3) . . 2_655 2_655 ?

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
_geom_hbond_publ_flag
O1 H1 Cl1 0.92(2) 2.23(2) 3.1445(12) 175.7(18) . yes
N1 H11 Cl1 0.865(18) 2.376(17) 3.1866(12) 156.2(14) . yes
N1 H12 Cl1 0.895(18) 2.594(17) 3.2557(13) 131.4(13) 3_445 yes
N1 H12 Cl1 0.895(18) 2.821(17) 3.3832(13) 122.1(13) 7_566 yes
N1 H13 Cl1 0.871(18) 2.329(18) 3.1866(13) 168.1(15) 4_545 yes

_refine_diff_density_max         0.266
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_d
_database_code_depnum_ccdc_archive 'CCDC 2455702'
loop_
_audit_author_name
_audit_author_address
'Alexander Medvedev'
;Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-06-01 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H12 N2, 0.617(H2 O), 0.383(H2 O2), 2(Cl)'
_chemical_formula_sum            'C4 H14 Cl2 N2 O1.38'
_chemical_formula_weight         183.15

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   10.4790(10)
_cell_length_b                   6.1798(6)
_cell_length_c                   13.5150(16)
_cell_angle_alpha                90
_cell_angle_beta                 109.635(3)
_cell_angle_gamma                90
_cell_volume                     824.31(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2899
_cell_measurement_theta_min      3.891
_cell_measurement_theta_max      30.407

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.725
_shelx_estimated_absorpt_T_min   0.760
_shelx_estimated_absorpt_T_max   0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8209
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5877
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.201
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             993
_reflns_number_gt                884
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0147P)²+0.7040P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         993
_refine_ls_number_parameters     66
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0567
_refine_ls_wR_factor_gt          0.0542
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.30248(3) 1.09400(6) 0.65973(3) 0.01599(11) Uani 1 1 d . . . . .
N1 N 0.54867(12) 0.9059(2) 0.60365(9) 0.0132(3) Uani 1 1 d . . . . .
H11 H 0.6056(18) 0.820(3) 0.6483(15) 0.029(5) Uiso 1 1 d . . . . .
H12 H 0.4908(18) 0.969(3) 0.6355(14) 0.023(5) Uiso 1 1 d . . . . .
C1 C 0.62871(14) 1.0751(2) 0.57137(11) 0.0142(3) Uani 1 1 d . . . . .
H111 H 0.693607 1.004976 0.542558 0.017 Uiso 1 1 calc R U . . .
H112 H 0.681035 1.161545 0.633421 0.017 Uiso 1 1 calc R U . . .
C2 C 0.46481(14) 0.7778(2) 0.51081(10) 0.0142(3) Uani 1 1 d . . . . .
H211 H 0.410525 0.669769 0.533472 0.017 Uiso 1 1 calc R U . . .
H212 H 0.524913 0.699060 0.480165 0.017 Uiso 1 1 calc R U . . .
O1 O 0.5524(4) 0.5086(6) 0.7248(3) 0.0177(12) Uani 0.383(10) 1 d D . P A 1
H1 H 0.609(5) 0.413(7) 0.756(4) 0.027 Uiso 0.383(10) 1 d D U P A 1
O2 O 0.500000 0.5326(6) 0.750000 0.0294(13) Uani 0.617(10) 2 d DS T P A 2
H2 H 0.566(3) 0.448(6) 0.764(4) 0.044 Uiso 0.617(10) 1 d D U P A 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
N1 C1 1.4943(18) . ?
N1 C2 1.4943(17) . ?
N1 H11 0.872(19) . ?
N1 H12 0.938(19) . ?
C1 C2 1.5128(19) 5_676 ?
C1 H111 0.9900 . ?
C1 H112 0.9900 . ?
C2 H211 0.9900 . ?
C2 H212 0.9900 . ?
O1 O1 1.474(9) 2_656 ?
O1 H1 0.84(2) . ?
O2 H2 0.835(19) . ?
O2 H2 0.835(19) 2_656 ?

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 110.80(11) . . ?
C1 N1 H11 107.9(12) . . ?
C2 N1 H11 109.3(12) . . ?
C1 N1 H12 110.9(11) . . ?
C2 N1 H12 108.5(11) . . ?
H11 N1 H12 109.4(16) . . ?
N1 C1 C2 110.25(11) . 5_676 ?
N1 C1 H111 109.6 . . ?
C2 C1 H111 109.6 5_676 . ?
N1 C1 H112 109.6 . . ?
C2 C1 H112 109.6 5_676 . ?
H111 C1 H112 108.1 . . ?
N1 C2 C1 110.55(11) . 5_676 ?
N1 C2 H211 109.5 . . ?
C1 C2 H211 109.5 5_676 . ?
N1 C2 H212 109.5 . . ?
C1 C2 H212 109.5 5_676 . ?
H211 C2 H212 108.1 . . ?
O1 O1 H1 106(4) 2_656 . ?
H2 O2 H2 103(7) . 2_656 ?

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
C2 N1 C1 C2 57.29(16) . . . 5_676 ?
C1 N1 C2 C1 -57.47(16) . . . 5_676 ?
H1 O1 O1 H1 -86(8) . . 2_656 2_656 ?

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
_geom_hbond_publ_flag
N1 H12 Cl1 0.938(19) 2.244(19) 3.1455(14) 161.0(15) . yes
N1 H11 Cl1 0.872(19) 2.453(19) 3.1639(13) 139.1(16) 3_545 yes
N1 H11 O1^a 0.872(19) 2.338(19) 2.944(4) 126.7(15) . yes
N1 H11 O2^b 0.872(19) 2.700(19) 3.190(3) 116.8(14) . yes
O1^a H1^a Cl1 0.84(2) 2.31(3) 3.118(4) 161(5) 2_646 yes
O2^b H2^b Cl1 0.835(19) 2.61(3) 3.379(3) 155(5) 2_646 yes

_refine_diff_density_max         0.386
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_c
_database_code_depnum_ccdc_archive 'CCDC 2455701'
loop_
_audit_author_name
_audit_author_address
'Alexander Medvedev'
;Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-06-01 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H12 N2, 0.731(H2 O2), 0.269(H2 O), 2(Cl)'
_chemical_formula_sum            'C4 H14 Cl2 N2 O1.73'
_chemical_formula_weight         188.75

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   10.6313(7)
_cell_length_b                   6.1567(4)
_cell_length_c                   13.5716(12)
_cell_angle_alpha                90
_cell_angle_beta                 110.665(2)
_cell_angle_gamma                90
_cell_volume                     831.16(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4906
_cell_measurement_theta_min      3.208
_cell_measurement_theta_max      30.541

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_F_000             399
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.725
_shelx_estimated_absorpt_T_min   0.760
_shelx_estimated_absorpt_T_max   0.812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8648
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7820
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.209
_diffrn_reflns_theta_max         30.541
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1277
_reflns_number_gt                1184
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0139P)²+0.8239P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1277
_refine_ls_number_parameters     67
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0224
_refine_ls_wR_factor_ref         0.0528
_refine_ls_wR_factor_gt          0.0514
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.30372(2) 1.08853(4) 0.65793(2) 0.01187(7) Uani 1 1 d . . . . .
N1 N 0.54813(9) 0.90221(15) 0.60322(7) 0.01020(16) Uani 1 1 d . . . . .
H11 H 0.6042(14) 0.809(3) 0.6503(12) 0.020(4) Uiso 1 1 d . . . . .
H12 H 0.4966(15) 0.962(2) 0.6353(11) 0.017(3) Uiso 1 1 d . . . . .
C1 C 0.62968(10) 1.06936(17) 0.57271(8) 0.01127(19) Uani 1 1 d . . . . .
H111 H 0.692245 0.996908 0.543765 0.014 Uiso 1 1 calc R U . . .
H112 H 0.683653 1.153255 0.635669 0.014 Uiso 1 1 calc R U . . .
C2 C 0.46184(10) 0.77845(16) 0.50901(8) 0.01136(19) Uani 1 1 d . . . . .
H211 H 0.406891 0.671662 0.530594 0.014 Uiso 1 1 calc R U . . .
H212 H 0.519482 0.697744 0.478087 0.014 Uiso 1 1 calc R U . . .
O1 O 0.55180(17) 0.5064(2) 0.72537(12) 0.0158(5) Uani 0.731(9) 1 d . . P A 1
H1 H 0.602(3) 0.403(5) 0.759(3) 0.035(7) Uiso 0.731(9) 1 d . . P A 1
O2 O 0.500000 0.5262(9) 0.750000 0.031(3) Uani 0.269(9) 2 d DS T P A 2
H2 H 0.572(6) 0.452(15) 0.765(10) 0.046 Uiso 0.269(9) 1 d D U P A 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
N1 C2 1.4930(13) . ?
N1 C1 1.4951(13) . ?
N1 H11 0.908(15) . ?
N1 H12 0.892(15) . ?
C1 C2 1.5143(14) 5_676 ?
C1 H111 0.9900 . ?
C1 H112 0.9900 . ?
C2 H211 0.9900 . ?
C2 H212 0.9900 . ?
O1 O1 1.476(4) 2_656 ?
O1 H1 0.85(3) . ?
O2 H2 0.85(2) . ?
O2 H2 0.85(2) 2_656 ?

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
C2 N1 C1 110.81(8) . . ?
C2 N1 H11 109.4(10) . . ?
C1 N1 H11 109.2(9) . . ?
C2 N1 H12 109.4(10) . . ?
C1 N1 H12 111.6(10) . . ?
H11 N1 H12 106.4(13) . . ?
N1 C1 C2 110.07(8) . 5_676 ?
N1 C1 H111 109.6 . . ?
C2 C1 H111 109.6 5_676 . ?
N1 C1 H112 109.6 . . ?
C2 C1 H112 109.6 5_676 . ?
H111 C1 H112 108.2 . . ?
N1 C2 C1 110.68(8) . 5_676 ?
N1 C2 H211 109.5 . . ?
C1 C2 H211 109.5 5_676 . ?
N1 C2 H212 109.5 . . ?
C1 C2 H212 109.5 5_676 . ?
H211 C2 H212 108.1 . . ?
O1 O1 H1 100(2) 2_656 . ?
H2 O2 H2 115(10) . 2_656 ?

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
C2 N1 C1 C2 57.23(11) . . . 5_676 ?
C1 N1 C2 C1 -57.59(12) . . . 5_676 ?
H1 O1 O1 H1 -81(4) 2_656 2_656 . . ?

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
_geom_hbond_publ_flag
N1 H12 Cl1 0.892(15) 2.312(15) 3.1592(9) 158.6(13) . yes
N1 H11 Cl1 0.908(15) 2.489(15) 3.2001(9) 135.5(12) 3_545 yes
N1 H11 O1^a 0.908(15) 2.285(15) 2.9398(16) 128.8(12) . yes
N1 H11 O2^b 0.908(15) 2.674(15) 3.211(4) 118.8(11) . yes
O1^a H1^a Cl1 0.85(3) 2.29(3) 3.1257(15) 169(3) 2_646 yes
O2^b H2^b Cl1 0.85(2) 2.62(7) 3.367(4) 147(10) 2_646 yes

_refine_diff_density_max         0.399
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_a_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2455703'
loop_
_audit_author_name
_audit_author_address
'Alexander Medvedev'
;Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-06-01 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H12 N2, H2 O2, 2(Br)'
_chemical_formula_sum            'C4 H14 Br2 N2 O2'
_chemical_formula_weight         281.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.1916(9)
_cell_length_b                   6.2618(5)
_cell_length_c                   13.9442(12)
_cell_angle_alpha                90
_cell_angle_beta                 111.211(3)
_cell_angle_gamma                90
_cell_volume                     911.00(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3710
_cell_measurement_theta_min      3.134
_cell_measurement_theta_max      30.517

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.056
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    8.851
_shelx_estimated_absorpt_T_min   0.299
_shelx_estimated_absorpt_T_max   0.619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6549
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6168
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.134
_diffrn_reflns_theta_max         28.988
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1211
_reflns_number_gt                1093
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0206P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1211
_refine_ls_number_parameters     58
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0231
_refine_ls_wR_factor_ref         0.0570
_refine_ls_wR_factor_gt          0.0547
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_restrained_S_all      1.165
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.69914(2) 0.58738(3) 0.34456(2) 0.00858(9) Uani 1 1 d . . . . .
N1 N 0.4535(2) 0.4068(3) 0.39884(16) 0.0087(4) Uani 1 1 d . . . . .
H11 H 0.507(3) 0.472(5) 0.369(2) 0.013(7) Uiso 1 1 d . . . . .
H12 H 0.399(3) 0.313(5) 0.351(2) 0.024(8) Uiso 1 1 d . . . . .
C1 C 0.5344(2) 0.2809(3) 0.49042(16) 0.0090(4) Uani 1 1 d . . . . .
H111 H 0.586001 0.175541 0.469234 0.011 Uiso 1 1 calc R U . . .
H112 H 0.478529 0.201937 0.519313 0.011 Uiso 1 1 calc R U . . .
C2 C 0.3772(2) 0.5722(3) 0.42810(18) 0.0085(4) Uani 1 1 d . . . . .
H211 H 0.316431 0.502120 0.454980 0.010 Uiso 1 1 calc R U . . .
H212 H 0.327037 0.656565 0.366685 0.010 Uiso 1 1 calc R U . . .
O1 O 0.45264(17) 0.0212(3) 0.27532(15) 0.0176(4) Uani 1 1 d . . . . .
H1 H 0.391(4) -0.076(6) 0.240(3) 0.054(13) Uiso 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
N1 C2 1.490(3) . ?
N1 C1 1.495(3) . ?
N1 H11 0.93(3) . ?
N1 H12 0.93(3) . ?
C1 C2 1.517(3) 5_666 ?
C1 H111 0.9900 . ?
C1 H112 0.9900 . ?
C2 H211 0.9900 . ?
C2 H212 0.9900 . ?
O1 O1 1.471(4) 2_655 ?
O1 H1 0.92(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
C2 N1 C1 111.24(18) . . ?
C2 N1 H11 109.9(18) . . ?
C1 N1 H11 108.7(17) . . ?
C2 N1 H12 110.2(18) . . ?
C1 N1 H12 108.7(19) . . ?
H11 N1 H12 108(3) . . ?
N1 C1 C2 110.45(18) . 5_666 ?
N1 C1 H111 109.6 . . ?
C2 C1 H111 109.6 5_666 . ?
N1 C1 H112 109.6 . . ?
C2 C1 H112 109.6 5_666 . ?
H111 C1 H112 108.1 . . ?
N1 C2 C1 110.08(18) . 5_666 ?
N1 C2 H211 109.6 . . ?
C1 C2 H211 109.6 5_666 . ?
N1 C2 H212 109.6 . . ?
C1 C2 H212 109.6 5_666 . ?
H211 C2 H212 108.2 . . ?
O1 O1 H1 106(3) 2_655 . ?

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
C2 N1 C1 C2 -57.4(3) . . . 5_666 ?
C1 N1 C2 C1 57.2(3) . . . 5_666 ?
H1 O1 O1 H1 -93(5) . . 2_655 2_655 ?

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
_geom_hbond_publ_flag
N1 H11 Br1 0.93(3) 2.41(3) 3.304(2) 160(2) . yes
N1 H12 O1 0.93(3) 2.29(3) 2.964(3) 128(2) . yes
N1 H12 Br1 0.93(3) 2.62(3) 3.334(2) 134(2) 3_445 yes
O1 H1 Br1 0.92(4) 2.45(4) 3.3173(19) 158(3) 2_645 yes

_refine_diff_density_max         0.430
_refine_diff_density_min         -0.724
_refine_diff_density_rms         0.146

####################################################################### 
# 
# 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_a_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 2489952'
loop_
_audit_author_name
_audit_author_address
'Alexander Medvedev'
;Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-09-20 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H14 N2, 0.712(H2 O), 0.288(H2 O2), 2(Cl)'
_chemical_formula_sum            'C6 H16 Cl2 N2 O1.29'
_chemical_formula_weight         207.71

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   9.7389(8)
_cell_length_b                   9.5339(8)
_cell_length_c                   10.3448(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.768(3)
_cell_angle_gamma                90
_cell_volume                     946.59(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4029
_cell_measurement_theta_min      3.012
_cell_measurement_theta_max      30.413

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_F_000             441
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.641
_shelx_estimated_absorpt_T_min   0.883
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8374
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7093
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.012
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1260
_reflns_number_gt                1140
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0249P)²+0.9321P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1260
_refine_ls_number_parameters     72
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0666
_refine_ls_wR_factor_gt          0.0638
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.78860(3) 0.55921(3) 0.50664(3) 0.01978(11) Uani 1 1 d . . . . .
N1 N 0.58012(10) 0.68270(11) 0.66789(10) 0.0151(2) Uani 1 1 d . . . . .
H3 H 0.6413(17) 0.6812(18) 0.6086(16) 0.023(4) Uiso 1 1 d . . . . .
C1 C 0.64247(13) 0.76928(15) 0.78375(13) 0.0212(3) Uani 1 1 d . . . . .
H11 H 0.640404 0.869823 0.759576 0.025 Uiso 1 1 calc R U . . .
H12 H 0.740613 0.741467 0.813922 0.025 Uiso 1 1 calc R U . . .
C2 C 0.44343(12) 0.74470(14) 0.60660(13) 0.0184(3) Uani 1 1 d . . . . .
H21 H 0.393536 0.679844 0.539951 0.022 Uiso 1 1 calc R U . . .
H22 H 0.458494 0.834537 0.563083 0.022 Uiso 1 1 calc R U . . .
C3 C 0.55904(14) 0.53534(14) 0.70995(13) 0.0204(3) Uani 1 1 d . . . . .
H31 H 0.645678 0.499361 0.763768 0.024 Uiso 1 1 calc R U . . .
H32 H 0.534784 0.474091 0.632147 0.024 Uiso 1 1 calc R U . . .
O1 O 0.4759(7) 0.1950(9) 0.8132(6) 0.0406(19) Uani 0.288(11) 1 d D . P A 2
H1 H 0.534(8) 0.155(9) 0.866(8) 0.061 Uiso 0.288(11) 1 d D U P A 2
O2 O 0.500000 0.2217(3) 0.750000 0.0411(14) Uani 0.712(11) 2 d DS T P A 1
H2 H 0.537(5) 0.173(5) 0.810(4) 0.060(14) Uiso 0.712(11) 1 d D . P A 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
N1 C3 1.4952(16) . ?
N1 C2 1.4957(15) . ?
N1 C1 1.4965(17) . ?
N1 H3 0.925(17) . ?
C1 C2 1.5373(18) 2_656 ?
C1 H11 0.9900 . ?
C1 H12 0.9900 . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
C3 C3 1.527(3) 2_656 ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
O1 O1 1.462(13) 2_656 ?
O1 H1 0.81(4) . ?
O1 H2 1.27(4) 2_656 ?
O2 H2 0.80(4) . ?
O2 H2 0.80(4) 2_656 ?

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
C3 N1 C2 109.78(10) . . ?
C3 N1 C1 110.02(10) . . ?
C2 N1 C1 109.43(10) . . ?
C3 N1 H3 108.3(11) . . ?
C2 N1 H3 110.7(10) . . ?
C1 N1 H3 108.6(10) . . ?
N1 C1 C2 108.01(10) . 2_656 ?
N1 C1 H11 110.1 . . ?
C2 C1 H11 110.1 2_656 . ?
N1 C1 H12 110.1 . . ?
C2 C1 H12 110.1 2_656 . ?
H11 C1 H12 108.4 . . ?
N1 C2 C1 107.70(10) . 2_656 ?
N1 C2 H21 110.2 . . ?
C1 C2 H21 110.2 2_656 . ?
N1 C2 H22 110.2 . . ?
C1 C2 H22 110.2 2_656 . ?
H21 C2 H22 108.5 . . ?
N1 C3 C3 108.12(6) . 2_656 ?
N1 C3 H31 110.1 . . ?
C3 C3 H31 110.1 2_656 . ?
N1 C3 H32 110.1 . . ?
C3 C3 H32 110.1 2_656 . ?
H31 C3 H32 108.4 . . ?
O1 O1 H1 108(7) 2_656 . ?
H1 O1 H2 123(7) . 2_656 ?
H2 O2 H2 110(6) . 2_656 ?

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
C3 N1 C1 C2 -49.32(13) . . . 2_656 ?
C2 N1 C1 C2 71.38(12) . . . 2_656 ?
C3 N1 C2 C1 70.91(13) . . . 2_656 ?
C1 N1 C2 C1 -49.92(12) . . . 2_656 ?
C2 N1 C3 C3 -50.13(16) . . . 2_656 ?
C1 N1 C3 C3 70.34(16) . . . 2_656 ?

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
_geom_hbond_publ_flag
N1 H3 Cl1 0.925(17) 2.244(17) 3.0726(11) 148.8(15) . yes
O1^b H1^b Cl1 0.81(4) 2.19(4) 2.993(6) 172(10) 4_646 yes
O2^a H2^a Cl1 0.80(4) 2.57(4) 3.3492(14) 165(5) 4_646 yes

_refine_diff_density_max         0.415
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.051


_chemical_properties_physical    Moisture-sensitive
