# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_b
_database_code_depnum_ccdc_archive 'CCDC 2289223'
loop_
_audit_author_name
_audit_author_address
'Alexander Medvedev'
;Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-08-17 deposited with the CCDC.	2024-01-10 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         'C13 H20 Br2 N2 O2, H2 O2'
_chemical_formula_sum            'C13 H22 Br2 N2 O4'
_chemical_formula_weight         430.14

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'
Br Br -0.2901 2.4595 '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                   15.8307(10)
_cell_length_b                   7.7891(5)
_cell_length_c                   26.3237(17)
_cell_angle_alpha                90
_cell_angle_beta                 90.248(2)
_cell_angle_gamma                90
_cell_volume                     3245.9(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8653
_cell_measurement_theta_min      2.573
_cell_measurement_theta_max      27.544

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    5.011
_shelx_estimated_absorpt_T_min   0.434
_shelx_estimated_absorpt_T_max   0.634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5908
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS (Bruker, 2018)'
_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            35478
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.008
_diffrn_reflns_theta_max         25.147
_diffrn_reflns_theta_full        25.147
_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             5811
_reflns_number_gt                4704
_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)+(0.0325P)²+14.1060P] 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         5811
_refine_ls_number_parameters     405
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
Br1 Br 0.89583(3) -0.46352(6) 0.53588(2) 0.02092(12) Uani 1 1 d . . . . .
Br2 Br 0.88360(3) 0.41005(7) 0.37386(2) 0.02753(14) Uani 1 1 d . . . . .
N1 N 0.7874(2) -0.0797(5) 0.51158(14) 0.0135(8) Uani 1 1 d . . . . .
N2 N 0.7591(2) 0.0857(5) 0.41804(14) 0.0153(8) Uani 1 1 d . . . . .
C1 C 0.9065(3) -0.2695(6) 0.48958(18) 0.0192(10) Uani 1 1 d . . . . .
H1A H 0.966790 -0.250546 0.481374 0.023 Uiso 1 1 calc R U . . .
H1B H 0.875835 -0.294107 0.457560 0.023 Uiso 1 1 calc R U . . .
C2 C 0.8704(3) -0.1103(6) 0.51420(16) 0.0152(9) Uani 1 1 d . . . . .
C3 C 0.7241(3) -0.2014(6) 0.49259(17) 0.0156(9) Uani 1 1 d . . . . .
H3A H 0.695288 -0.255136 0.521883 0.019 Uiso 1 1 calc R U . . .
H3B H 0.753025 -0.293511 0.473494 0.019 Uiso 1 1 calc R U . . .
C4 C 0.6577(3) -0.1183(6) 0.45815(17) 0.0161(10) Uani 1 1 d . . . . .
C5 C 0.5908(3) -0.2519(6) 0.44492(18) 0.0206(10) Uani 1 1 d . . . . .
H5A H 0.550089 -0.202329 0.420872 0.031 Uiso 1 1 calc R U . . .
H5B H 0.561279 -0.286929 0.475892 0.031 Uiso 1 1 calc R U . . .
H5C H 0.617831 -0.352143 0.429489 0.031 Uiso 1 1 calc R U . . .
C6 C 0.6966(3) -0.0509(6) 0.40848(17) 0.0179(10) Uani 1 1 d . . . . .
H6A H 0.724290 -0.147016 0.390405 0.021 Uiso 1 1 calc R U . . .
H6B H 0.651129 -0.005698 0.386301 0.021 Uiso 1 1 calc R U . . .
C7 C 0.6189(3) 0.0335(6) 0.48673(17) 0.0151(9) Uani 1 1 d . . . . .
H7A H 0.574391 0.087471 0.465597 0.018 Uiso 1 1 calc R U . . .
H7B H 0.592746 -0.007404 0.518598 0.018 Uiso 1 1 calc R U . . .
C8 C 0.6876(3) 0.1648(6) 0.49889(16) 0.0133(9) Uani 1 1 d . . . . .
C9 C 0.6517(3) 0.3203(6) 0.52666(18) 0.0180(10) Uani 1 1 d . . . . .
H9A H 0.697206 0.402151 0.533818 0.027 Uiso 1 1 calc R U . . .
H9B H 0.626107 0.283066 0.558655 0.027 Uiso 1 1 calc R U . . .
H9C H 0.608668 0.375444 0.505329 0.027 Uiso 1 1 calc R U . . .
C10 C 0.7275(3) 0.2279(6) 0.44923(17) 0.0153(9) Uani 1 1 d . . . . .
H10A H 0.684891 0.293266 0.429540 0.018 Uiso 1 1 calc R U . . .
H10B H 0.774796 0.306624 0.457319 0.018 Uiso 1 1 calc R U . . .
C11 C 0.7531(3) 0.0790(5) 0.53385(16) 0.0140(9) Uani 1 1 d . . . . .
H11A H 0.799996 0.160271 0.540367 0.017 Uiso 1 1 calc R U . . .
H11B H 0.726437 0.051754 0.566825 0.017 Uiso 1 1 calc R U . . .
C12 C 0.8391(3) 0.0660(6) 0.40242(16) 0.0166(10) Uani 1 1 d . . . . .
C13 C 0.9035(3) 0.2047(6) 0.41458(18) 0.0205(10) Uani 1 1 d . . . . .
H13A H 0.961030 0.160564 0.407798 0.025 Uiso 1 1 calc R U . . .
H13B H 0.900185 0.234433 0.451081 0.025 Uiso 1 1 calc R U . . .
O1 O 0.9205(2) -0.0109(4) 0.53549(13) 0.0253(8) Uani 1 1 d . . . . .
O2 O 0.8624(2) -0.0639(4) 0.37919(12) 0.0231(8) Uani 1 1 d . . . . .
Br3 Br 0.64569(4) 0.99894(7) 0.82491(2) 0.04115(18) Uani 1 1 d . . . . .
Br4 Br 0.52290(3) 0.69282(7) 0.59065(2) 0.03177(15) Uani 1 1 d . . . . .
N3 N 0.7111(2) 0.6275(4) 0.76177(13) 0.0122(8) Uani 1 1 d . . . . .
N4 N 0.7493(2) 0.6106(5) 0.65661(13) 0.0134(8) Uani 1 1 d . . . . .
C14 C 0.6164(3) 0.8781(6) 0.76313(19) 0.0216(11) Uani 1 1 d . . . . .
H14A H 0.555862 0.897323 0.755354 0.026 Uiso 1 1 calc R U . . .
H14B H 0.649798 0.925249 0.734664 0.026 Uiso 1 1 calc R U . . .
C15 C 0.6325(3) 0.6887(6) 0.76730(16) 0.0144(9) Uani 1 1 d . . . . .
C16 C 0.7880(3) 0.7333(5) 0.76275(17) 0.0137(9) Uani 1 1 d . . . . .
H16A H 0.813106 0.728352 0.797228 0.016 Uiso 1 1 calc R U . . .
H16B H 0.772320 0.854209 0.755884 0.016 Uiso 1 1 calc R U . . .
C17 C 0.8548(3) 0.6769(5) 0.72395(17) 0.0126(9) Uani 1 1 d . . . . .
C18 C 0.9360(3) 0.7783(6) 0.73373(18) 0.0182(10) Uani 1 1 d . . . . .
H18A H 0.954763 0.759533 0.768817 0.027 Uiso 1 1 calc R U . . .
H18B H 0.925224 0.900844 0.728342 0.027 Uiso 1 1 calc R U . . .
H18C H 0.979960 0.739399 0.710309 0.027 Uiso 1 1 calc R U . . .
C19 C 0.8260(3) 0.7093(6) 0.66931(17) 0.0155(9) Uani 1 1 d . . . . .
H19A H 0.814436 0.833221 0.664704 0.019 Uiso 1 1 calc R U . . .
H19B H 0.871836 0.676745 0.645753 0.019 Uiso 1 1 calc R U . . .
C20 C 0.8708(3) 0.4835(5) 0.73037(17) 0.0142(9) Uani 1 1 d . . . . .
H20A H 0.914109 0.444953 0.705889 0.017 Uiso 1 1 calc R U . . .
H20B H 0.891803 0.459708 0.765132 0.017 Uiso 1 1 calc R U . . .
C21 C 0.7886(3) 0.3866(5) 0.72109(16) 0.0128(9) Uani 1 1 d . . . . .
C22 C 0.8020(3) 0.1930(5) 0.72494(17) 0.0164(10) Uani 1 1 d . . . . .
H22A H 0.749258 0.133633 0.716285 0.025 Uiso 1 1 calc R U . . .
H22B H 0.818835 0.163164 0.759696 0.025 Uiso 1 1 calc R U . . .
H22C H 0.846392 0.157871 0.701297 0.025 Uiso 1 1 calc R U . . .
C23 C 0.7577(3) 0.4247(6) 0.66683(17) 0.0145(9) Uani 1 1 d . . . . .
H23A H 0.798(3) 0.380(6) 0.6437(18) 0.017 Uiso 1 1 d . U . . .
H23B H 0.706(3) 0.368(6) 0.6613(16) 0.012(12) Uiso 1 1 d . . . . .
C24 C 0.7244(3) 0.4404(5) 0.76127(17) 0.0124(9) Uani 1 1 d . . . . .
H24A H 0.669887 0.382375 0.754369 0.015 Uiso 1 1 calc R U . . .
H24B H 0.744524 0.402942 0.795151 0.015 Uiso 1 1 calc R U . . .
C25 C 0.6779(3) 0.6935(6) 0.64545(16) 0.0140(9) Uani 1 1 d . . . . .
C26 C 0.5981(3) 0.5859(6) 0.63882(18) 0.0208(11) Uani 1 1 d . . . . .
H26A H 0.569287 0.573861 0.671947 0.025 Uiso 1 1 calc R U . . .
H26B H 0.613378 0.469635 0.626732 0.025 Uiso 1 1 calc R U . . .
O3 O 0.57044(19) 0.5917(4) 0.77247(13) 0.0226(8) Uani 1 1 d . . . . .
O4 O 0.67510(19) 0.8522(4) 0.64187(12) 0.0193(7) Uani 1 1 d . . . . .
O5 O 0.4258(2) 0.6386(5) 0.86348(13) 0.0296(8) Uani 1 1 d D . . . .
H5 H 0.403(3) 0.541(4) 0.859(2) 0.045(19) Uiso 1 1 d D . . . .
O6 O 0.4209(2) 0.6977(4) 0.81093(13) 0.0213(7) Uani 1 1 d D . . . .
H6 H 0.4718(14) 0.676(8) 0.803(2) 0.044(18) Uiso 1 1 d D . . . .
O7 O 0.9744(3) 0.1193(6) 0.65069(16) 0.0287(9) Uani 0.796(6) 1 d D . P A 1
H7 H 1.0251(17) 0.090(9) 0.645(3) 0.043 Uiso 0.796(6) 1 d D U P A 1
O8 O 0.9416(3) 0.2282(6) 0.60975(18) 0.0287(9) Uani 0.796(6) 1 d D . P A 1
H8 H 0.926(4) 0.175(8) 0.5832(16) 0.043 Uiso 0.796(6) 1 d D U P A 1
O9 O 0.9776(12) 0.234(2) 0.6285(7) 0.0287(9) Uani 0.204(6) 1 d D . P A 2
H9 H 1.025056 0.183967 0.626293 0.043 Uiso 0.204(6) 1 d R U P A 2
O10 O 0.9272(11) 0.079(2) 0.6298(7) 0.0287(9) Uani 0.204(6) 1 d D . P A 2
H10 H 0.925023 0.049686 0.598732 0.043 Uiso 0.204(6) 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
Br1 C1 1.949(5) . ?
Br2 C13 1.951(5) . ?
N1 C2 1.336(5) . ?
N1 C3 1.466(5) . ?
N1 C11 1.472(5) . ?
N2 C12 1.341(6) . ?
N2 C10 1.468(6) . ?
N2 C6 1.474(6) . ?
C1 C2 1.513(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 O1 1.240(5) . ?
C3 C4 1.528(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.525(6) . ?
C4 C7 1.531(6) . ?
C4 C6 1.540(6) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.526(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.526(6) . ?
C8 C10 1.535(6) . ?
C8 C11 1.536(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O2 1.239(6) . ?
C12 C13 1.519(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
Br3 C14 1.934(5) . ?
Br4 C26 1.925(4) . ?
N3 C15 1.340(5) . ?
N3 C16 1.471(5) . ?
N3 C24 1.472(5) . ?
N4 C25 1.334(6) . ?
N4 C19 1.473(5) . ?
N4 C23 1.479(6) . ?
C14 C15 1.501(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O3 1.248(5) . ?
C16 C17 1.538(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C19 1.528(6) . ?
C17 C18 1.529(6) . ?
C17 C20 1.537(6) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.522(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.526(6) . ?
C21 C24 1.529(6) . ?
C21 C23 1.537(6) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.96(5) . ?
C23 H23B 0.94(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 O4 1.241(5) . ?
C25 C26 1.526(6) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
O5 O6 1.459(5) . ?
O5 H5 0.847(10) . ?
O6 H6 0.848(10) . ?
O7 O8 1.464(6) . ?
O7 H7 0.849(10) . ?
O8 H8 0.848(10) . ?
O9 O10 1.448(17) . ?
O9 H9 0.8500 . ?
O10 H10 0.8499 . ?

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 C3 125.0(4) . . ?
C2 N1 C11 119.5(4) . . ?
C3 N1 C11 115.2(3) . . ?
C12 N2 C10 125.6(4) . . ?
C12 N2 C6 119.9(4) . . ?
C10 N2 C6 114.2(3) . . ?
C2 C1 Br1 109.5(3) . . ?
C2 C1 H1A 109.8 . . ?
Br1 C1 H1A 109.8 . . ?
C2 C1 H1B 109.8 . . ?
Br1 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
O1 C2 N1 122.6(4) . . ?
O1 C2 C1 117.5(4) . . ?
N1 C2 C1 119.9(4) . . ?
N1 C3 C4 113.3(4) . . ?
N1 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
N1 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C3 108.8(4) . . ?
C5 C4 C7 111.0(4) . . ?
C3 C4 C7 108.1(4) . . ?
C5 C4 C6 108.6(4) . . ?
C3 C4 C6 111.9(4) . . ?
C7 C4 C6 108.5(4) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C4 111.8(4) . . ?
N2 C6 H6A 109.3 . . ?
C4 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C4 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C4 109.5(3) . . ?
C8 C7 H7A 109.8 . . ?
C4 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
C4 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C7 111.5(4) . . ?
C9 C8 C10 108.0(4) . . ?
C7 C8 C10 109.4(4) . . ?
C9 C8 C11 108.1(4) . . ?
C7 C8 C11 108.2(4) . . ?
C10 C8 C11 111.7(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C8 112.2(4) . . ?
N2 C10 H10A 109.2 . . ?
C8 C10 H10A 109.2 . . ?
N2 C10 H10B 109.2 . . ?
C8 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N1 C11 C8 112.1(3) . . ?
N1 C11 H11A 109.2 . . ?
C8 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
C8 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
O2 C12 N2 121.9(4) . . ?
O2 C12 C13 118.9(4) . . ?
N2 C12 C13 119.2(4) . . ?
C12 C13 Br2 111.1(3) . . ?
C12 C13 H13A 109.4 . . ?
Br2 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
Br2 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C15 N3 C16 124.5(4) . . ?
C15 N3 C24 119.1(4) . . ?
C16 N3 C24 115.9(3) . . ?
C25 N4 C19 119.6(4) . . ?
C25 N4 C23 126.1(4) . . ?
C19 N4 C23 113.4(3) . . ?
C15 C14 Br3 112.1(3) . . ?
C15 C14 H14A 109.2 . . ?
Br3 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
Br3 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
O3 C15 N3 121.9(4) . . ?
O3 C15 C14 118.0(4) . . ?
N3 C15 C14 120.0(4) . . ?
N3 C16 C17 113.6(3) . . ?
N3 C16 H16A 108.9 . . ?
C17 C16 H16A 108.9 . . ?
N3 C16 H16B 108.9 . . ?
C17 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C19 C17 C18 108.7(4) . . ?
C19 C17 C20 108.3(4) . . ?
C18 C17 C20 110.5(3) . . ?
C19 C17 C16 112.0(3) . . ?
C18 C17 C16 108.7(4) . . ?
C20 C17 C16 108.7(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N4 C19 C17 111.7(3) . . ?
N4 C19 H19A 109.3 . . ?
C17 C19 H19A 109.3 . . ?
N4 C19 H19B 109.3 . . ?
C17 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
C21 C20 C17 109.2(3) . . ?
C21 C20 H20A 109.8 . . ?
C17 C20 H20A 109.8 . . ?
C21 C20 H20B 109.8 . . ?
C17 C20 H20B 109.8 . . ?
H20A C20 H20B 108.3 . . ?
C20 C21 C22 111.2(4) . . ?
C20 C21 C24 108.9(4) . . ?
C22 C21 C24 108.5(3) . . ?
C20 C21 C23 108.8(3) . . ?
C22 C21 C23 107.2(4) . . ?
C24 C21 C23 112.3(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N4 C23 C21 112.7(4) . . ?
N4 C23 H23A 108(3) . . ?
C21 C23 H23A 108(3) . . ?
N4 C23 H23B 111(3) . . ?
C21 C23 H23B 109(3) . . ?
H23A C23 H23B 108(4) . . ?
N3 C24 C21 111.9(3) . . ?
N3 C24 H24A 109.2 . . ?
C21 C24 H24A 109.2 . . ?
N3 C24 H24B 109.2 . . ?
C21 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
O4 C25 N4 121.9(4) . . ?
O4 C25 C26 120.6(4) . . ?
N4 C25 C26 117.4(4) . . ?
C25 C26 Br4 110.3(3) . . ?
C25 C26 H26A 109.6 . . ?
Br4 C26 H26A 109.6 . . ?
C25 C26 H26B 109.6 . . ?
Br4 C26 H26B 109.6 . . ?
H26A C26 H26B 108.1 . . ?
O6 O5 H5 97(4) . . ?
O5 O6 H6 97(4) . . ?
O8 O7 H7 111(5) . . ?
O7 O8 H8 115(5) . . ?
O10 O9 H9 96.0 . . ?
O9 O10 H10 103.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
H6 O6 O5 H5 -100(6) . . . . ?
H7 O7 O8 H8 80(8) . . . . ?
H9 O9 O10 H10 -79.1 . . . . ?

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
O5 H5 O4 0.847(10) 1.93(2) 2.748(5) 163(6) 2_646 yes
O6 H6 O3 0.848(10) 1.881(19) 2.708(4) 165(6) . yes
O8^a H8^a O1 0.848(10) 1.92(3) 2.719(6) 156(7) . yes
O10^b H10^b O1 0.85 1.73 2.582(18) 179.9 . yes
O7^a H7^a O2 0.849(10) 1.90(2) 2.738(5) 167(7) 3_756 yes
O9^b H9^b O2 0.85 2.02 2.87(2) 179.8 3_756 yes

_refine_diff_density_max         2.548
_refine_diff_density_min         -1.821
_refine_diff_density_rms         0.112

####################################################################### 
# 
# 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 2289225'
loop_
_audit_author_name
_audit_author_address
'Alexander Medvedev'
;Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-08-17 deposited with the CCDC.	2024-01-10 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         'C13 H20 Br2 N2 O5, H2 O2'
_chemical_formula_sum            'C13 H22 Br2 N2 O7'
_chemical_formula_weight         478.14

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'
Br Br -0.2901 2.4595 '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                   7.1669(7)
_cell_length_b                   20.9465(16)
_cell_length_c                   11.2346(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.934(4)
_cell_angle_gamma                90
_cell_volume                     1682.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3564
_cell_measurement_theta_min      2.668
_cell_measurement_theta_max      29.655

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.888
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    4.857
_shelx_estimated_absorpt_T_min   0.529
_shelx_estimated_absorpt_T_max   0.793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6327
_exptl_absorpt_correction_T_max  0.7461
_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            6415
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.944
_diffrn_reflns_theta_max         25.992
_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             1657
_reflns_number_gt                1366
_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)+5.1446P] 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         1657
_refine_ls_number_parameters     127
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_restrained_S_all      1.153
_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 0.47275(6) 0.17161(2) 0.43439(4) 0.02446(16) Uani 1 1 d . . . . .
O1 O 0.2400(4) 0.26910(14) 0.2982(3) 0.0234(7) Uani 1 1 d . . . . .
N1 N 0.3900(5) 0.36105(17) 0.3476(3) 0.0164(8) Uani 1 1 d . . . . .
C1 C 0.5073(6) 0.2626(2) 0.4402(4) 0.0189(9) Uani 1 1 d . . . . .
H11 H 0.494651 0.277718 0.522799 0.023 Uiso 1 1 calc R U . . .
H12 H 0.635363 0.273006 0.418482 0.023 Uiso 1 1 calc R U . . .
C2 C 0.3669(6) 0.2974(2) 0.3565(4) 0.0157(9) Uani 1 1 d . . . . .
C3 C 0.5422(6) 0.3979(2) 0.4082(4) 0.0170(9) Uani 1 1 d . . . . .
H31 H 0.632638 0.368261 0.449554 0.020 Uiso 1 1 calc R U . . .
H32 H 0.490675 0.425765 0.469066 0.020 Uiso 1 1 calc R U . . .
C4 C 0.2577(6) 0.3982(2) 0.2709(4) 0.0187(9) Uani 1 1 d . . . . .
H41 H 0.184323 0.426211 0.321155 0.022 Uiso 1 1 calc R U . . .
H42 H 0.169506 0.368773 0.227065 0.022 Uiso 1 1 calc R U . . .
C5 C 0.3552(6) 0.43943(19) 0.1808(4) 0.0157(9) Uani 1 1 d . . . . .
C6 C 0.2040(6) 0.4771(2) 0.1065(4) 0.0239(10) Uani 1 1 d . . . . .
H61 H 0.123791 0.447311 0.059111 0.036 Uiso 1 1 calc R U . . .
H62 H 0.263822 0.506555 0.053085 0.036 Uiso 1 1 calc R U . . .
H63 H 0.127989 0.501359 0.159940 0.036 Uiso 1 1 calc R U . . .
C7 C 0.500000 0.4825(3) 0.250000 0.0214(14) Uani 1 2 d S T P . .
O2 O 0.4221(5) 0.52098(17) 0.3371(3) 0.0319(9) Uani 1 1 d D . . . .
H2 H 0.46(2) 0.558(3) 0.320(12) 0.09(6) Uiso 0.5 1 d D . P . .
O3 O 0.2394(8) 0.5542(3) 0.3005(6) 0.0226(14) Uani 0.5 1 d D . P . .
H3 H 0.288(14) 0.589(3) 0.279(10) 0.04(3) Uiso 0.5 1 d D . P . .
O4 O 0.4208(5) 0.66168(16) 0.2862(3) 0.0308(8) Uani 1 1 d D . . . .
H4 H 0.354(7) 0.690(2) 0.251(4) 0.046(18) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.923(4) . ?
O1 C2 1.235(5) . ?
N1 C2 1.349(5) . ?
N1 C4 1.462(5) . ?
N1 C3 1.465(5) . ?
C1 C2 1.516(6) . ?
C1 H11 0.9900 . ?
C1 H12 0.9900 . ?
C3 C5 1.549(5) 2_655 ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
C4 C5 1.534(5) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
C5 C6 1.540(6) . ?
C5 C7 1.543(5) . ?
C6 H61 0.9800 . ?
C6 H62 0.9800 . ?
C6 H63 0.9800 . ?
C7 O2 1.413(5) . ?
C7 O2 1.413(5) 2_655 ?
O2 O3 1.514(7) . ?
O2 H2 0.850(10) . ?
O3 H3 0.848(10) . ?
O4 O4 1.441(6) 2_655 ?
O4 H4 0.848(10) . ?

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 C4 119.5(4) . . ?
C2 N1 C3 125.3(4) . . ?
C4 N1 C3 115.2(3) . . ?
C2 C1 Br1 112.1(3) . . ?
C2 C1 H11 109.2 . . ?
Br1 C1 H11 109.2 . . ?
C2 C1 H12 109.2 . . ?
Br1 C1 H12 109.2 . . ?
H11 C1 H12 107.9 . . ?
O1 C2 N1 121.7(4) . . ?
O1 C2 C1 122.2(4) . . ?
N1 C2 C1 116.2(4) . . ?
N1 C3 C5 111.6(3) . 2_655 ?
N1 C3 H31 109.3 . . ?
C5 C3 H31 109.3 2_655 . ?
N1 C3 H32 109.3 . . ?
C5 C3 H32 109.3 2_655 . ?
H31 C3 H32 108.0 . . ?
N1 C4 C5 112.5(3) . . ?
N1 C4 H41 109.1 . . ?
C5 C4 H41 109.1 . . ?
N1 C4 H42 109.1 . . ?
C5 C4 H42 109.1 . . ?
H41 C4 H42 107.8 . . ?
C4 C5 C6 108.1(3) . . ?
C4 C5 C7 108.5(3) . . ?
C6 C5 C7 113.5(4) . . ?
C4 C5 C3 111.6(3) . 2_655 ?
C6 C5 C3 106.6(3) . 2_655 ?
C7 C5 C3 108.7(3) . 2_655 ?
C5 C6 H61 109.5 . . ?
C5 C6 H62 109.5 . . ?
H61 C6 H62 109.5 . . ?
C5 C6 H63 109.5 . . ?
H61 C6 H63 109.5 . . ?
H62 C6 H63 109.5 . . ?
O2 C7 O2 110.3(5) . 2_655 ?
O2 C7 C5 105.6(2) . 2_655 ?
O2 C7 C5 113.5(2) 2_655 2_655 ?
O2 C7 C5 113.5(2) . . ?
O2 C7 C5 105.6(2) 2_655 . ?
C5 C7 C5 108.6(5) 2_655 . ?
C7 O2 O3 116.7(3) . . ?
C7 O2 H2 102(9) . . ?
O3 O2 H2 79(10) . . ?
O2 O3 H3 96(8) . . ?
O4 O4 H4 100(4) 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
C4 N1 C2 O1 2.5(6) . . . . ?
C3 N1 C2 O1 -176.4(4) . . . . ?
C4 N1 C2 C1 -178.6(3) . . . . ?
C3 N1 C2 C1 2.5(6) . . . . ?
Br1 C1 C2 O1 4.0(5) . . . . ?
Br1 C1 C2 N1 -174.9(3) . . . . ?
C2 N1 C3 C5 127.0(4) . . . 2_655 ?
C4 N1 C3 C5 -51.9(5) . . . 2_655 ?
C2 N1 C4 C5 -126.7(4) . . . . ?
C3 N1 C4 C5 52.3(5) . . . . ?
N1 C4 C5 C6 -179.1(4) . . . . ?
N1 C4 C5 C7 -55.7(5) . . . . ?
N1 C4 C5 C3 64.0(5) . . . 2_655 ?
C4 C5 C7 O2 -56.4(5) . . . . ?
C6 C5 C7 O2 63.7(4) . . . . ?
C3 C5 C7 O2 -177.9(3) 2_655 . . . ?
C4 C5 C7 O2 -177.4(3) . . . 2_655 ?
C6 C5 C7 O2 -57.2(4) . . . 2_655 ?
C3 C5 C7 O2 61.2(4) 2_655 . . 2_655 ?
C4 C5 C7 C5 60.7(3) . . . 2_655 ?
C6 C5 C7 C5 -179.2(4) . . . 2_655 ?
C3 C5 C7 C5 -60.8(3) 2_655 . . 2_655 ?
O2 C7 O2 O3 73.9(4) 2_655 . . . ?
C5 C7 O2 O3 -163.1(4) 2_655 . . . ?
C5 C7 O2 O3 -44.3(6) . . . . ?

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
O4 H4 O1 0.848(10) 1.85(2) 2.672(4) 162(6) 4 yes
O2 H2 O4 0.850(10) 2.22(7) 3.002(5) 152(14) . yes
O3 H3 O4 0.848(10) 1.80(4) 2.610(7) 160(11) . yes

_refine_diff_density_max         0.483
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.112

####################################################################### 
# 
# 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 2289226'
loop_
_audit_author_name
_audit_author_address
'Alexander Medvedev'
;Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-08-17 deposited with the CCDC.	2024-01-10 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         'C13 H20 Cl2 N2 O5, H2 O2'
_chemical_formula_sum            'C13 H22 Cl2 N2 O7'
_chemical_formula_weight         389.26

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                   7.1348(3)
_cell_length_b                   20.9560(8)
_cell_length_c                   11.0766(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.2510(10)
_cell_angle_gamma                90
_cell_volume                     1651.58(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5750
_cell_measurement_theta_min      2.680
_cell_measurement_theta_max      30.336

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.433
_shelx_estimated_absorpt_T_min   0.918
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6839
_exptl_absorpt_correction_T_max  0.7461
_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            13470
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.944
_diffrn_reflns_theta_max         28.992
_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             2199
_reflns_number_gt                1940
_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)+(0.0366P)²+2.0473P] 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         2199
_refine_ls_number_parameters     127
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0917
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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 0.47169(6) 0.82429(2) 0.43570(4) 0.03039(12) Uani 1 1 d . . . . .
O1 O 0.23619(16) 0.73359(5) 0.30053(10) 0.0265(3) Uani 1 1 d . . . . .
C1 C 0.5084(2) 0.74066(7) 0.44208(13) 0.0208(3) Uani 1 1 d . . . . .
H11 H 0.636720 0.730895 0.419068 0.025 Uiso 1 1 calc R U . . .
H12 H 0.498454 0.725662 0.526120 0.025 Uiso 1 1 calc R U . . .
C2 C 0.3657(2) 0.70524(7) 0.35781(13) 0.0181(3) Uani 1 1 d . . . . .
C3 C 0.5433(2) 0.60515(7) 0.40987(13) 0.0191(3) Uani 1 1 d . . . . .
H31 H 0.492135 0.577391 0.471855 0.023 Uiso 1 1 calc R U . . .
H32 H 0.634453 0.634809 0.451761 0.023 Uiso 1 1 calc R U . . .
C4 C 0.2565(2) 0.60461(7) 0.27054(14) 0.0220(3) Uani 1 1 d . . . . .
H41 H 0.167220 0.633942 0.226057 0.026 Uiso 1 1 calc R U . . .
H42 H 0.183431 0.576524 0.321474 0.026 Uiso 1 1 calc R U . . .
C5 C 0.3541(2) 0.56354(7) 0.17913(13) 0.0195(3) Uani 1 1 d . . . . .
C6 C 0.2024(3) 0.52598(8) 0.10372(16) 0.0320(4) Uani 1 1 d . . . . .
H61 H 0.122128 0.555689 0.055037 0.048 Uiso 1 1 calc R U . . .
H62 H 0.125728 0.501968 0.157867 0.048 Uiso 1 1 calc R U . . .
H63 H 0.262323 0.496290 0.050110 0.048 Uiso 1 1 calc R U . . .
C7 C 0.500000 0.52045(10) 0.250000 0.0238(4) Uani 1 2 d S T P B .
N1 N 0.38950(16) 0.64206(6) 0.34883(11) 0.0180(2) Uani 1 1 d . . . . .
O2 O 0.5781(2) 0.48251(6) 0.16143(11) 0.0348(3) Uani 1 1 d . . . . .
H2 H 0.584(6) 0.447(2) 0.202(4) 0.027(10) Uiso 0.5 1 d . . P A 1
O3 O 0.7619(3) 0.44869(11) 0.2012(2) 0.0251(5) Uani 0.5 1 d . . P B 2
H3 H 0.716(7) 0.411(2) 0.218(5) 0.053(14) Uiso 0.5 1 d . . P C 2
O4 O 0.58226(19) 0.34151(6) 0.21546(12) 0.0353(3) Uani 1 1 d D . . . .
H4 H 0.647(3) 0.3155(11) 0.257(2) 0.062(8) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7726(15) . ?
O1 C2 1.2338(18) . ?
C1 C2 1.522(2) . ?
C1 H11 0.9900 . ?
C1 H12 0.9900 . ?
C2 N1 1.3395(18) . ?
C3 N1 1.4660(18) . ?
C3 C5 1.5411(19) 2_655 ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
C4 N1 1.4650(18) . ?
C4 C5 1.535(2) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
C5 C6 1.535(2) . ?
C5 C7 1.5473(19) . ?
C6 H61 0.9800 . ?
C6 H62 0.9800 . ?
C6 H63 0.9800 . ?
C7 O2 1.4093(16) . ?
C7 O2 1.4093(16) 2_655 ?
O2 O3 1.527(2) . ?
O2 H2 0.87(4) . ?
O3 H3 0.89(5) . ?
O4 O4 1.448(2) 2_655 ?
O4 H4 0.829(17) . ?

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 C1 Cl1 111.57(10) . . ?
C2 C1 H11 109.3 . . ?
Cl1 C1 H11 109.3 . . ?
C2 C1 H12 109.3 . . ?
Cl1 C1 H12 109.3 . . ?
H11 C1 H12 108.0 . . ?
O1 C2 N1 122.14(13) . . ?
O1 C2 C1 121.45(13) . . ?
N1 C2 C1 116.40(12) . . ?
N1 C3 C5 112.23(12) . 2_655 ?
N1 C3 H31 109.2 . . ?
C5 C3 H31 109.2 2_655 . ?
N1 C3 H32 109.2 . . ?
C5 C3 H32 109.2 2_655 . ?
H31 C3 H32 107.9 . . ?
N1 C4 C5 112.66(11) . . ?
N1 C4 H41 109.1 . . ?
C5 C4 H41 109.1 . . ?
N1 C4 H42 109.1 . . ?
C5 C4 H42 109.1 . . ?
H41 C4 H42 107.8 . . ?
C4 C5 C6 108.08(12) . . ?
C4 C5 C3 111.41(12) . 2_655 ?
C6 C5 C3 106.95(12) . 2_655 ?
C4 C5 C7 108.28(11) . . ?
C6 C5 C7 113.43(13) . . ?
C3 C5 C7 108.73(11) 2_655 . ?
C5 C6 H61 109.5 . . ?
C5 C6 H62 109.5 . . ?
H61 C6 H62 109.5 . . ?
C5 C6 H63 109.5 . . ?
H61 C6 H63 109.5 . . ?
H62 C6 H63 109.5 . . ?
O2 C7 O2 111.31(18) . 2_655 ?
O2 C7 C5 105.18(7) . . ?
O2 C7 C5 113.37(8) 2_655 . ?
O2 C7 C5 113.37(8) . 2_655 ?
O2 C7 C5 105.19(7) 2_655 2_655 ?
C5 C7 C5 108.58(16) . 2_655 ?
C2 N1 C4 119.56(12) . . ?
C2 N1 C3 125.59(12) . . ?
C4 N1 C3 114.83(11) . . ?
C7 O2 O3 115.87(12) . . ?
C7 O2 H2 97(3) . . ?
O2 O3 H3 99(3) . . ?
O4 O4 H4 98.7(19) 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
Cl1 C1 C2 O1 -4.38(18) . . . . ?
Cl1 C1 C2 N1 175.15(10) . . . . ?
N1 C4 C5 C6 179.24(13) . . . . ?
N1 C4 C5 C3 -63.55(17) . . . 2_655 ?
N1 C4 C5 C7 55.98(16) . . . . ?
C4 C5 C7 O2 177.67(12) . . . . ?
C6 C5 C7 O2 57.71(15) . . . . ?
C3 C5 C7 O2 -61.13(15) 2_655 . . . ?
C4 C5 C7 O2 55.84(16) . . . 2_655 ?
C6 C5 C7 O2 -64.12(16) . . . 2_655 ?
C3 C5 C7 O2 177.04(12) 2_655 . . 2_655 ?
C4 C5 C7 C5 -60.67(9) . . . 2_655 ?
C6 C5 C7 C5 179.37(14) . . . 2_655 ?
C3 C5 C7 C5 60.53(9) 2_655 . . 2_655 ?
O1 C2 N1 C4 -1.2(2) . . . . ?
C1 C2 N1 C4 179.30(12) . . . . ?
O1 C2 N1 C3 177.50(14) . . . . ?
C1 C2 N1 C3 -2.0(2) . . . . ?
C5 C4 N1 C2 126.68(14) . . . . ?
C5 C4 N1 C3 -52.13(17) . . . . ?
C5 C3 N1 C2 -127.23(14) 2_655 . . . ?
C5 C3 N1 C4 51.49(16) 2_655 . . . ?
O2 C7 O2 O3 -72.94(13) 2_655 . . . ?
C5 C7 O2 O3 163.89(14) . . . . ?
C5 C7 O2 O3 45.4(2) 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
O2 H2^a O4 0.87(4) 2.22(4) 3.0145(18) 152(4) . yes
O3^b H3^b O4 0.89(5) 1.73(5) 2.597(3) 164(5) . yes
O4 H4 O1 0.829(17) 1.882(19) 2.6561(16) 155(3) 3_545 yes

_refine_diff_density_max         0.348
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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 2289224'
loop_
_audit_author_name
_audit_author_address
'Alexander Medvedev'
;Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-08-17 deposited with the CCDC.	2024-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H20 I2 N2 O5, 0.5(H2 O2)'
_chemical_formula_sum            'C13 H21 I2 N2 O6'
_chemical_formula_weight         555.12

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'
I I -0.4742 1.8119 '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                   13.6546(5)
_cell_length_b                   8.6106(3)
_cell_length_c                   15.3908(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.962(2)
_cell_angle_gamma                90
_cell_volume                     1748.21(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4030
_cell_measurement_theta_min      2.734
_cell_measurement_theta_max      29.673

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.109
_exptl_crystal_F_000             1068
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    3.628
_shelx_estimated_absorpt_T_min   0.713
_shelx_estimated_absorpt_T_max   0.899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6659
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS (Bruker, 2018)'
_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            12198
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.544
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_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             3075
_reflns_number_gt                2609
_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-2016/6 (Sheldrick, 2016)'
_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)+(0.0217P)²+11.7681P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3075
_refine_ls_number_parameters     220
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.0917
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_restrained_S_all      1.203
_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
I1 I 0.55430(4) 0.33894(6) 0.80919(3) 0.02687(16) Uani 1 1 d . . . . .
I2 I 0.90579(4) 0.19862(6) 0.43772(4) 0.02781(16) Uani 1 1 d . . . . .
N1 N 0.6631(4) 0.4998(7) 0.6420(4) 0.0158(13) Uani 1 1 d . . . . .
N2 N 0.8485(4) 0.4563(7) 0.5996(4) 0.0180(14) Uani 1 1 d . . . . .
O1 O 0.5779(4) 0.2961(6) 0.5677(3) 0.0262(13) Uani 1 1 d . . . . .
O2 O 0.8647(4) 0.2259(6) 0.6704(4) 0.0251(12) Uani 1 1 d . . . . .
C1 C 0.6471(6) 0.2606(9) 0.7245(5) 0.0200(17) Uani 1 1 d . . . . .
H11 H 0.719407 0.269676 0.757394 0.024 Uiso 1 1 calc R U . . .
H12 H 0.632533 0.149809 0.709355 0.024 Uiso 1 1 calc R U . . .
C2 C 0.6276(5) 0.3541(9) 0.6394(5) 0.0185(16) Uani 1 1 d . . . . .
C3 C 0.7236(5) 0.5781(8) 0.7224(5) 0.0167(16) Uani 1 1 d . . . . .
H31 H 0.744376 0.501270 0.771552 0.020 Uiso 1 1 calc R U . . .
H32 H 0.681201 0.657469 0.741739 0.020 Uiso 1 1 calc R U . . .
C4 C 0.8197(6) 0.6576(9) 0.7069(5) 0.0230(18) Uani 1 1 d . . . . .
C5 C 0.8714(7) 0.7368(10) 0.7960(6) 0.035(2) Uani 1 1 d . . . . .
H51 H 0.832607 0.829075 0.803898 0.053 Uiso 1 1 calc R U . . .
H52 H 0.940329 0.767635 0.795323 0.053 Uiso 1 1 calc R U . . .
H53 H 0.874468 0.664445 0.845753 0.053 Uiso 1 1 calc R U . . .
C6 C 0.7832(6) 0.7711(9) 0.6266(6) 0.0268(19) Uani 1 1 d . . . . .
C7 C 0.6392(6) 0.5935(9) 0.5597(5) 0.0231(18) Uani 1 1 d . . . . .
H71 H 0.588345 0.672913 0.564238 0.028 Uiso 1 1 calc R U . . .
H72 H 0.608475 0.525625 0.507963 0.028 Uiso 1 1 calc R U . . .
C8 C 0.7314(6) 0.6744(9) 0.5420(5) 0.0224(17) Uani 1 1 d . . . . .
C9 C 0.6945(7) 0.7744(9) 0.4560(6) 0.032(2) Uani 1 1 d . . . . .
H91 H 0.752142 0.830498 0.444170 0.048 Uiso 1 1 calc R U . . .
H92 H 0.643635 0.848940 0.464657 0.048 Uiso 1 1 calc R U . . .
H93 H 0.664412 0.706839 0.404807 0.048 Uiso 1 1 calc R U . . .
C10 C 0.8920(5) 0.5399(9) 0.6840(5) 0.0239(18) Uani 1 1 d . . . . .
H101 H 0.954292 0.594136 0.679185 0.029 Uiso 1 1 calc R U . . .
H102 H 0.911502 0.463681 0.733619 0.029 Uiso 1 1 calc R U . . .
C11 C 0.8089(6) 0.5580(8) 0.5233(5) 0.0200(17) Uani 1 1 d . . . . .
H111 H 0.776192 0.494432 0.470073 0.024 Uiso 1 1 calc R U . . .
H112 H 0.865649 0.615604 0.509218 0.024 Uiso 1 1 calc R U . . .
C12 C 0.8385(5) 0.3030(8) 0.6008(5) 0.0169(16) Uani 1 1 d . . . . .
C13 C 0.7939(5) 0.2184(9) 0.5126(5) 0.0212(17) Uani 1 1 d . . . . .
H131 H 0.734444 0.276252 0.476785 0.025 Uiso 1 1 calc R U . . .
H132 H 0.770984 0.113565 0.525049 0.025 Uiso 1 1 calc R U . . .
O3 O 0.7190(4) 0.8816(6) 0.6479(4) 0.0299(14) Uani 1 1 d D . . . .
H3 H 0.670950 0.899454 0.602462 0.045 Uiso 0.743(12) 1 d R U P A 1
O4 O 0.7768(17) 0.973(3) 0.7272(11) 0.053(9) Uani 0.257(12) 1 d D . P A 2
H4 H 0.788528 1.061762 0.710295 0.079 Uiso 0.257(12) 1 d R U P A 2
O5 O 0.8599(5) 0.8445(7) 0.5960(5) 0.0487(19) Uani 1 1 d D . . . .
H5 H 0.897012 0.895454 0.638518 0.073 Uiso 0.257(12) 1 d R U P A 2
O6 O 0.9262(5) 0.9295(9) 0.6652(4) 0.028(2) Uani 0.743(12) 1 d D . P A 1
H6 H 0.904531 1.020643 0.665546 0.042 Uiso 0.743(12) 1 d R U P A 1
O7 O 0.5343(4) 0.0001(7) 0.5457(3) 0.0311(14) Uani 1 1 d . . . . .
H7 H 0.546953 0.096862 0.547264 0.047 Uiso 1 1 d 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
I1 C1 2.147(7) . ?
I2 C13 2.144(7) . ?
N1 C2 1.342(9) . ?
N1 C3 1.464(9) . ?
N1 C7 1.465(9) . ?
N2 C12 1.328(9) . ?
N2 C11 1.453(9) . ?
N2 C10 1.469(9) . ?
O1 C2 1.242(9) . ?
O2 C12 1.232(8) . ?
C1 C2 1.501(10) . ?
C1 H11 0.9900 . ?
C1 H12 0.9900 . ?
C3 C4 1.552(10) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
C4 C10 1.518(10) . ?
C4 C5 1.531(11) . ?
C4 C6 1.553(11) . ?
C5 H51 0.9800 . ?
C5 H52 0.9800 . ?
C5 H53 0.9800 . ?
C6 O3 1.389(9) . ?
C6 O5 1.404(9) . ?
C6 C8 1.554(11) . ?
C7 C8 1.523(10) . ?
C7 H71 0.9900 . ?
C7 H72 0.9900 . ?
C8 C11 1.538(10) . ?
C8 C9 1.550(10) . ?
C9 H91 0.9800 . ?
C9 H92 0.9800 . ?
C9 H93 0.9800 . ?
C10 H101 0.9900 . ?
C10 H102 0.9900 . ?
C11 H111 0.9900 . ?
C11 H112 0.9900 . ?
C12 C13 1.522(10) . ?
C13 H131 0.9900 . ?
C13 H132 0.9900 . ?
O3 O4 1.493(10) . ?
O3 H3 0.8405 . ?
O4 H4 0.8401 . ?
O5 O6 1.411(7) . ?
O5 H5 0.8399 . ?
O6 H6 0.8397 . ?
O7 O7 1.475(10) 3_656 ?
O7 H7 0.8500 . ?

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 C3 125.2(6) . . ?
C2 N1 C7 119.5(6) . . ?
C3 N1 C7 115.3(6) . . ?
C12 N2 C11 126.3(6) . . ?
C12 N2 C10 119.6(6) . . ?
C11 N2 C10 113.6(6) . . ?
C2 C1 I1 111.2(5) . . ?
C2 C1 H11 109.4 . . ?
I1 C1 H11 109.4 . . ?
C2 C1 H12 109.4 . . ?
I1 C1 H12 109.4 . . ?
H11 C1 H12 108.0 . . ?
O1 C2 N1 120.8(7) . . ?
O1 C2 C1 119.5(7) . . ?
N1 C2 C1 119.7(7) . . ?
N1 C3 C4 112.9(6) . . ?
N1 C3 H31 109.0 . . ?
C4 C3 H31 109.0 . . ?
N1 C3 H32 109.0 . . ?
C4 C3 H32 109.0 . . ?
H31 C3 H32 107.8 . . ?
C10 C4 C5 109.2(7) . . ?
C10 C4 C3 111.5(6) . . ?
C5 C4 C3 105.8(6) . . ?
C10 C4 C6 109.2(6) . . ?
C5 C4 C6 114.3(7) . . ?
C3 C4 C6 106.8(6) . . ?
C4 C5 H51 109.5 . . ?
C4 C5 H52 109.5 . . ?
H51 C5 H52 109.5 . . ?
C4 C5 H53 109.5 . . ?
H51 C5 H53 109.5 . . ?
H52 C5 H53 109.5 . . ?
O3 C6 O5 110.0(6) . . ?
O3 C6 C4 109.6(6) . . ?
O5 C6 C4 115.8(7) . . ?
O3 C6 C8 112.7(7) . . ?
O5 C6 C8 100.3(6) . . ?
C4 C6 C8 108.3(6) . . ?
N1 C7 C8 113.4(6) . . ?
N1 C7 H71 108.9 . . ?
C8 C7 H71 108.9 . . ?
N1 C7 H72 108.9 . . ?
C8 C7 H72 108.9 . . ?
H71 C7 H72 107.7 . . ?
C7 C8 C11 112.1(6) . . ?
C7 C8 C9 107.8(6) . . ?
C11 C8 C9 106.8(6) . . ?
C7 C8 C6 108.3(6) . . ?
C11 C8 C6 108.6(6) . . ?
C9 C8 C6 113.3(7) . . ?
C8 C9 H91 109.5 . . ?
C8 C9 H92 109.5 . . ?
H91 C9 H92 109.5 . . ?
C8 C9 H93 109.5 . . ?
H91 C9 H93 109.5 . . ?
H92 C9 H93 109.5 . . ?
N2 C10 C4 113.2(6) . . ?
N2 C10 H101 108.9 . . ?
C4 C10 H101 108.9 . . ?
N2 C10 H102 108.9 . . ?
C4 C10 H102 108.9 . . ?
H101 C10 H102 107.8 . . ?
N2 C11 C8 111.8(6) . . ?
N2 C11 H111 109.3 . . ?
C8 C11 H111 109.3 . . ?
N2 C11 H112 109.3 . . ?
C8 C11 H112 109.3 . . ?
H111 C11 H112 107.9 . . ?
O2 C12 N2 122.7(7) . . ?
O2 C12 C13 118.5(6) . . ?
N2 C12 C13 118.8(6) . . ?
C12 C13 I2 109.9(5) . . ?
C12 C13 H131 109.7 . . ?
I2 C13 H131 109.7 . . ?
C12 C13 H132 109.7 . . ?
I2 C13 H132 109.7 . . ?
H131 C13 H132 108.2 . . ?
C6 O3 O4 108.7(12) . . ?
C6 O3 H3 109.5 . . ?
O3 O4 H4 109.2 . . ?
C6 O5 O6 111.7(6) . . ?
C6 O5 H5 109.0 . . ?
O5 O6 H6 109.3 . . ?
O7 O7 H7 95.9 3_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 C2 O1 -179.0(6) . . . . ?
C7 N1 C2 O1 2.5(10) . . . . ?
C3 N1 C2 C1 1.7(10) . . . . ?
C7 N1 C2 C1 -176.7(6) . . . . ?
I1 C1 C2 O1 -105.3(7) . . . . ?
I1 C1 C2 N1 73.9(7) . . . . ?
C2 N1 C3 C4 131.3(7) . . . . ?
C7 N1 C3 C4 -50.2(8) . . . . ?
N1 C3 C4 C10 -63.1(8) . . . . ?
N1 C3 C4 C5 178.3(6) . . . . ?
N1 C3 C4 C6 56.2(8) . . . . ?
C10 C4 C6 O3 -178.5(6) . . . . ?
C5 C4 C6 O3 -55.9(8) . . . . ?
C3 C4 C6 O3 60.7(8) . . . . ?
C10 C4 C6 O5 -53.4(8) . . . . ?
C5 C4 C6 O5 69.2(8) . . . . ?
C3 C4 C6 O5 -174.2(6) . . . . ?
C10 C4 C6 C8 58.2(8) . . . . ?
C5 C4 C6 C8 -179.2(6) . . . . ?
C3 C4 C6 C8 -62.6(7) . . . . ?
C2 N1 C7 C8 -132.1(7) . . . . ?
C3 N1 C7 C8 49.3(8) . . . . ?
N1 C7 C8 C11 65.2(8) . . . . ?
N1 C7 C8 C9 -177.5(6) . . . . ?
N1 C7 C8 C6 -54.6(8) . . . . ?
O3 C6 C8 C7 -59.0(8) . . . . ?
O5 C6 C8 C7 -175.9(6) . . . . ?
C4 C6 C8 C7 62.4(7) . . . . ?
O3 C6 C8 C11 179.0(6) . . . . ?
O5 C6 C8 C11 62.2(7) . . . . ?
C4 C6 C8 C11 -59.6(7) . . . . ?
O3 C6 C8 C9 60.5(8) . . . . ?
O5 C6 C8 C9 -56.4(8) . . . . ?
C4 C6 C8 C9 -178.1(6) . . . . ?
C12 N2 C10 C4 -119.3(7) . . . . ?
C11 N2 C10 C4 53.5(8) . . . . ?
C5 C4 C10 N2 179.4(6) . . . . ?
C3 C4 C10 N2 62.9(8) . . . . ?
C6 C4 C10 N2 -54.9(8) . . . . ?
C12 N2 C11 C8 117.7(8) . . . . ?
C10 N2 C11 C8 -54.6(8) . . . . ?
C7 C8 C11 N2 -61.7(8) . . . . ?
C9 C8 C11 N2 -179.6(7) . . . . ?
C6 C8 C11 N2 57.9(8) . . . . ?
C11 N2 C12 O2 -172.1(7) . . . . ?
C10 N2 C12 O2 -0.2(10) . . . . ?
C11 N2 C12 C13 8.6(10) . . . . ?
C10 N2 C12 C13 -179.6(6) . . . . ?
O2 C12 C13 I2 -102.2(6) . . . . ?
N2 C12 C13 I2 77.2(7) . . . . ?
O5 C6 O3 O4 -66.6(12) . . . . ?
C4 C6 O3 O4 61.8(12) . . . . ?
C8 C6 O3 O4 -177.6(11) . . . . ?
O3 C6 O5 O6 67.2(9) . . . . ?
C4 C6 O5 O6 -57.7(8) . . . . ?
C8 C6 O5 O6 -173.9(6) . . . . ?

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
O7 H7 O1 0.85 1.78 2.620(8) 171.7 .
O4 H4 O2 0.84 1.95 2.74(2) 157.3 1_565
O6 H6 O2 0.84 1.86 2.695(9) 176.4 1_565
O3 H3 O7 0.84 2.04 2.798(8) 150.1 1_565

_refine_diff_density_max         1.267
_refine_diff_density_min         -1.277
_refine_diff_density_rms         0.165

