#------------------------------------------------------------------------------
#$Date: 2022-02-04 20:17:10 +0100 (vie 04 de feb de 2022) $
#$Revision: 272598 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/39/7243990.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_7243990
loop_
_publ_author_name
'Navasardyan, Mger A.'
'Bezzubov, Stanislav I.'
'Medvedev, Alexander G.'
'Prikhodchenko, Petr V.'
'Churakov, Andrei V.'
_publ_section_title
;
 Novel peroxosolvates of tetraalkylammonium halides: the first case of
 layers containing hydrogen-bonded peroxide molecules
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              38
_journal_page_last               42
_journal_paper_doi               10.1039/D1CE01476E
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C8 H20 N, 2(H2 O2), Cl'
_chemical_formula_sum            'C8 H24 Cl N O4'
_chemical_formula_weight         233.73
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2021-10-20 deposited with the CCDC.	2021-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8741(5)
_cell_length_b                   8.4164(3)
_cell_length_c                   12.6736(6)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.515
_cell_measurement_theta_min      2.351
_cell_volume                     1266.56(9)
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART Photon II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14169
_diffrn_reflns_theta_full        28.98
_diffrn_reflns_theta_max         28.98
_diffrn_reflns_theta_min         2.91
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  0.9711
_exptl_absorpt_correction_T_min  0.9167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2018)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3342
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0757P)²+0.1688P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1013
_reflns_number_gt                3271
_reflns_number_total             3342
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            d1ce01476e2.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 7243990--7243993.cif.'
_cod_database_code               7243990
loop_
_symmetry_equiv_pos_as_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'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.69355(3) 0.85963(4) 0.61686(3) 0.02469(11) Uani 1 1 d . . .
N1 N 0.48951(9) 0.49623(15) 0.38746(9) 0.0150(2) Uani 1 1 d . . .
C1 C 0.48752(12) 0.38606(18) 0.48228(12) 0.0209(3) Uani 1 1 d . . .
C2 C 0.49285(14) 0.21054(19) 0.45496(17) 0.0304(4) Uani 1 1 d . . .
C3 C 0.59848(12) 0.47933(17) 0.32578(12) 0.0193(3) Uani 1 1 d . . .
C4 C 0.70435(12) 0.5167(2) 0.38728(16) 0.0275(3) Uani 1 1 d . . .
C5 C 0.47601(12) 0.66287(18) 0.43183(12) 0.0210(3) Uani 1 1 d . . .
C6 C 0.48496(16) 0.7952(2) 0.35156(18) 0.0319(4) Uani 1 1 d . . .
C7 C 0.39475(12) 0.45739(18) 0.31104(11) 0.0211(3) Uani 1 1 d . . .
C8 C 0.27876(14) 0.4504(2) 0.35965(14) 0.0277(3) Uani 1 1 d . . .
O1 O 0.79965(14) 0.27626(19) 0.67455(14) 0.0443(4) Uani 1 1 d . . .
O2 O 0.70176(12) 0.23388(17) 0.61310(18) 0.0420(3) Uani 1 1 d . . .
O3 O 0.94368(11) 0.60803(17) 0.68935(10) 0.0304(3) Uani 1 1 d . . .
O4 O 0.86392(9) 0.58209(13) 0.60310(9) 0.0253(2) Uani 1 1 d . . .
H1 H 0.815(2) 0.368(4) 0.648(3) 0.049(9) Uiso 1 1 d . . .
H2 H 0.705(2) 0.128(4) 0.618(4) 0.050(8) Uiso 1 1 d . . .
H3 H 1.007(2) 0.621(3) 0.663(2) 0.029(6) Uiso 1 1 d . . .
H4 H 0.8193(19) 0.666(3) 0.612(3) 0.031(5) Uiso 1 1 d . . .
H32 H 0.6006(17) 0.368(2) 0.2980(16) 0.010(4) Uiso 1 1 d . . .
H12 H 0.419(2) 0.417(3) 0.524(2) 0.026(5) Uiso 1 1 d . . .
H72 H 0.396(2) 0.535(3) 0.256(2) 0.029(6) Uiso 1 1 d . . .
H63 H 0.559(2) 0.799(3) 0.323(2) 0.031(6) Uiso 1 1 d . . .
H52 H 0.406(2) 0.668(3) 0.4668(18) 0.021(5) Uiso 1 1 d . . .
H23 H 0.565(2) 0.184(3) 0.421(2) 0.032(6) Uiso 1 1 d . . .
H31 H 0.5905(19) 0.546(3) 0.2641(19) 0.021(5) Uiso 1 1 d . . .
H51 H 0.5332(18) 0.677(3) 0.4850(18) 0.021(5) Uiso 1 1 d . . .
H11 H 0.5495(19) 0.424(3) 0.525(2) 0.025(5) Uiso 1 1 d . . .
H83 H 0.270(3) 0.364(3) 0.410(3) 0.040(7) Uiso 1 1 d . . .
H71 H 0.413(2) 0.354(3) 0.282(2) 0.030(6) Uiso 1 1 d . . .
H62 H 0.432(3) 0.790(5) 0.293(3) 0.063(10) Uiso 1 1 d . . .
H22 H 0.418(3) 0.176(4) 0.415(3) 0.052(8) Uiso 1 1 d . . .
H43 H 0.760(2) 0.503(3) 0.334(2) 0.041(7) Uiso 1 1 d . . .
H42 H 0.722(2) 0.446(3) 0.444(2) 0.039(7) Uiso 1 1 d . . .
H41 H 0.709(3) 0.628(4) 0.411(3) 0.049(9) Uiso 1 1 d . . .
H82 H 0.258(2) 0.554(3) 0.388(3) 0.042(7) Uiso 1 1 d . . .
H61 H 0.475(3) 0.894(4) 0.389(3) 0.053(9) Uiso 1 1 d . . .
H81 H 0.227(3) 0.438(3) 0.303(3) 0.053(8) Uiso 1 1 d . . .
H21 H 0.491(3) 0.162(4) 0.515(4) 0.068(11) Uiso 1 1 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'
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'
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 C3 111.33(11) . . ?
C1 N1 C5 105.62(11) . . ?
C3 N1 C5 111.52(11) . . ?
C1 N1 C7 111.19(11) . . ?
C3 N1 C7 106.41(11) . . ?
C5 N1 C7 110.86(11) . . ?
N1 C1 C2 114.40(14) . . ?
N1 C1 H12 105.7(14) . . ?
C2 C1 H12 113.8(14) . . ?
N1 C1 H11 102.9(15) . . ?
C2 C1 H11 114.8(14) . . ?
H12 C1 H11 104(2) . . ?
C1 C2 H23 110.7(15) . . ?
C1 C2 H22 109.9(17) . . ?
H23 C2 H22 118(2) . . ?
C1 C2 H21 105(3) . . ?
H23 C2 H21 108(3) . . ?
H22 C2 H21 105(3) . . ?
C4 C3 N1 115.06(12) . . ?
C4 C3 H32 110.8(12) . . ?
N1 C3 H32 106.9(12) . . ?
C4 C3 H31 112.2(13) . . ?
N1 C3 H31 106.1(14) . . ?
H32 C3 H31 105.2(17) . . ?
C3 C4 H43 100.4(17) . . ?
C3 C4 H42 115.9(17) . . ?
H43 C4 H42 108(2) . . ?
C3 C4 H41 114(2) . . ?
H43 C4 H41 107(3) . . ?
H42 C4 H41 110(3) . . ?
C6 C5 N1 115.05(13) . . ?
C6 C5 H52 110.0(14) . . ?
N1 C5 H52 108.1(14) . . ?
C6 C5 H51 109.4(14) . . ?
N1 C5 H51 107.2(14) . . ?
H52 C5 H51 106.8(18) . . ?
C5 C6 H63 110.3(16) . . ?
C5 C6 H62 116(2) . . ?
H63 C6 H62 108(3) . . ?
C5 C6 H61 107(2) . . ?
H63 C6 H61 106(2) . . ?
H62 C6 H61 109(3) . . ?
C8 C7 N1 115.06(12) . . ?
C8 C7 H72 110.0(15) . . ?
N1 C7 H72 107.7(15) . . ?
C8 C7 H71 109.1(16) . . ?
N1 C7 H71 105.5(16) . . ?
H72 C7 H71 109(2) . . ?
C7 C8 H83 113.2(18) . . ?
C7 C8 H82 110.5(17) . . ?
H83 C8 H82 113(3) . . ?
C7 C8 H81 107(2) . . ?
H83 C8 H81 110(3) . . ?
H82 C8 H81 102(2) . . ?
O2 O1 H1 101(2) . . ?
O1 O2 H2 100(2) . . ?
O4 O3 H3 107.9(19) . . ?
O3 O4 H4 100.3(19) . . ?
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 1.5180(18) . ?
N1 C3 1.5184(17) . ?
N1 C5 1.5196(18) . ?
N1 C7 1.5202(18) . ?
C1 C2 1.519(2) . ?
C1 H12 1.00(2) . ?
C1 H11 0.97(2) . ?
C2 H23 0.99(3) . ?
C2 H22 1.07(3) . ?
C2 H21 0.86(4) . ?
C3 C4 1.512(2) . ?
C3 H32 0.999(18) . ?
C3 H31 0.97(2) . ?
C4 H43 0.95(3) . ?
C4 H42 0.95(3) . ?
C4 H41 0.98(3) . ?
C5 C6 1.512(2) . ?
C5 H52 0.95(2) . ?
C5 H51 0.96(2) . ?
C6 H63 0.95(3) . ?
C6 H62 0.97(4) . ?
C6 H61 0.97(3) . ?
C7 C8 1.510(2) . ?
C7 H72 0.95(3) . ?
C7 H71 0.97(2) . ?
C8 H83 0.98(3) . ?
C8 H82 0.98(3) . ?
C8 H81 0.96(4) . ?
O1 O2 1.4439(19) . ?
O1 H1 0.86(3) . ?
O2 H2 0.89(3) . ?
O3 O4 1.4627(17) . ?
O3 H3 0.82(3) . ?
O4 H4 0.89(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
O1 H1 O4 0.86(3) 1.97(3) 2.833(2) 173(3) .
O2 H2 Cl1 0.89(3) 2.26(3) 3.1517(15) 172(3) 1_545
O3 H3 Cl1 0.82(3) 2.30(3) 3.1179(13) 170(3) 3_565
O4 H4 Cl1 0.89(2) 2.21(2) 3.0951(12) 173(3) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
H1 O1 O2 H2 155(3) . . . . ?
H3 O3 O4 H4 -117(3) . . . . ?
