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#$Date: 2024-03-04 22:45:44 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290282 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/80/7248020.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7248020
loop_
_publ_author_name
'Medvedev, Alexander G.'
'Medved'ko, Aleksei V.'
'Vener, Mikhail V.'
'Churakov, Andrei V.'
'Prikhodchenko, Petr V.'
'Vatsadze, Sergey Z.'
_publ_section_title
;
 Dioxygen-halogen bonding exemplified by crystalline peroxosolvates of
 N,N'-bis(haloacetyl) bispidines.
;
_journal_issue                   6
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              5195
_journal_page_last               5206
_journal_paper_doi               10.1039/d3cp05834d
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C13 H20 Cl2 N2 O5, H2 O2'
_chemical_formula_sum            'C13 H22 Cl2 N2 O7'
_chemical_formula_weight         389.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2023-08-17 deposited with the CCDC.	2024-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.2510(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1348(3)
_cell_length_b                   20.9560(8)
_cell_length_c                   11.0766(4)
_cell_measurement_reflns_used    5750
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.336
_cell_measurement_theta_min      2.680
_cell_volume                     1651.58(11)
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13470
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.992
_diffrn_reflns_theta_min         1.944
_exptl_absorpt_coefficient_mu    0.433
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2199
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0366P)²+2.0473P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0917
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1940
_reflns_number_total             2199
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cp05834d3.cif
_cod_data_source_block           a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7248018--7248021.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7248020
_shelx_shelxl_version_number     2019/2
_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.
;
_shelx_estimated_absorpt_t_min   0.918
_shelx_estimated_absorpt_t_max   0.979
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'
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 . . . .
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'
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_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_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
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 . . . ?
