#------------------------------------------------------------------------------
#$Date: 2020-07-22 08:17:28 +0300 (Wed, 22 Jul 2020) $
#$Revision: 254470 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243499.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243499
loop_
_publ_author_name
'Navasardyan, Mger A.'
'Grishanov, Dmitry A.'
'Prikhodchenko, Petr V.'
'Churakov, Andrei V.'
_publ_section_title
;
 <small>DL</small>-Piperidinium-2-carboxylate bis(hydrogen peroxide):
 unusual hydrogen-bonded peroxide chains
;
_journal_coeditor_code           FY2147
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1331
_journal_page_last               1335
_journal_paper_doi               10.1107/S205698902000972X
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C6 H11 N O2, 2H2 O2'
_chemical_formula_moiety         'C6 H11 N O2, 2(H2 O2)'
_chemical_formula_sum            'C6 H15 N O6'
_chemical_formula_weight         197.19
_chemical_name_common            'pipecolic acid diperoxosolvate'
_chemical_name_systematic
;
DL-Piperidinium-2-carboxylate bis(hydrogen peroxide)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 93.7700(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5739(4)
_cell_length_b                   22.9278(15)
_cell_length_c                   6.0647(4)
_cell_measurement_reflns_used    5232
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.6225
_cell_measurement_theta_min      3.1055
_cell_volume                     912.12(10)
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXTL (Sheldrick, 2008)
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9809
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_min         3.105
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       nugget
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.188
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0306
_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)+(0.0419P)²+0.2180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0837
_reflns_number_gt                2170
_reflns_number_total             2418
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            fy2147sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243499
_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   0.939
_shelx_estimated_absorpt_t_max   0.939
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'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 -0.02450(12) 0.57964(3) 0.57611(13) 0.01528(16) Uani d 1 . .
H H1 -0.093(2) 0.5604(6) 0.463(2) 0.029(3) Uiso d 1 . .
H H2 0.039(2) 0.5538(6) 0.661(2) 0.025(3) Uiso d 1 . .
O O1 0.40875(11) 0.60608(3) 0.25095(12) 0.02266(17) Uani d 1 . .
O O2 0.21298(11) 0.52860(3) 0.30218(11) 0.02005(16) Uani d 1 . .
C C1 -0.17311(14) 0.61336(4) 0.70359(15) 0.01777(18) Uani d 1 . .
H H11 -0.2642(19) 0.5851(6) 0.759(2) 0.021(3) Uiso d 1 . .
H H12 -0.2449(19) 0.6384(6) 0.597(2) 0.024(3) Uiso d 1 . .
C C2 -0.05768(15) 0.64708(4) 0.88702(15) 0.01993(19) Uani d 1 . .
H H21 -0.157(2) 0.6679(6) 0.968(2) 0.029(3) Uiso d 1 . .
H H22 0.010(2) 0.6192(6) 0.988(2) 0.029(3) Uiso d 1 . .
C C3 0.10082(16) 0.68727(4) 0.79508(17) 0.0218(2) Uani d 1 . .
H H32 0.033(2) 0.7172(6) 0.703(2) 0.027(3) Uiso d 1 . .
H H31 0.179(2) 0.7082(6) 0.916(2) 0.030(3) Uiso d 1 . .
C C4 0.24769(14) 0.65223(4) 0.66075(16) 0.01923(19) Uani d 1 . .
H H41 0.343(2) 0.6784(6) 0.590(2) 0.027(3) Uiso d 1 . .
H H42 0.326(2) 0.6256(6) 0.759(2) 0.027(3) Uiso d 1 . .
C C5 0.13006(13) 0.61800(4) 0.47837(14) 0.01483(17) Uani d 1 . .
H H52 0.0520(18) 0.6451(5) 0.377(2) 0.019(3) Uiso d 1 . .
C C6 0.26188(13) 0.58042(4) 0.33422(14) 0.01570(18) Uani d 1 . .
O O3 0.74598(11) 0.54761(3) 0.18291(11) 0.01986(16) Uani d 1 . .
O O4 0.72361(11) 0.48529(3) 0.13828(12) 0.02162(16) Uani d 1 . .
H H4 0.737(2) 0.4839(7) -0.003(3) 0.040(4) Uiso d 1 . .
H H3 0.620(3) 0.5583(7) 0.194(3) 0.040(4) Uiso d 1 . .
O O5 0.67290(12) 0.72538(4) 0.33260(14) 0.02787(18) Uani d 1 . .
O O6 0.49801(12) 0.71623(3) 0.17405(13) 0.02507(17) Uani d 1 . .
H H5 0.613(2) 0.7454(7) 0.434(3) 0.041(4) Uiso d 1 . .
H H6 0.472(2) 0.6792(7) 0.199(2) 0.034(4) Uiso d 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 N1 C1 . . 112.57(7) ?
C5 N1 H1 . . 107.6(9) ?
C1 N1 H1 . . 109.2(9) ?
C5 N1 H2 . . 108.7(9) ?
C1 N1 H2 . . 110.4(9) ?
H1 N1 H2 . . 108.2(12) ?
N1 C1 C2 . . 109.24(7) ?
N1 C1 H11 . . 106.0(8) ?
C2 C1 H11 . . 112.4(8) ?
N1 C1 H12 . . 105.4(8) ?
C2 C1 H12 . . 112.9(8) ?
H11 C1 H12 . . 110.4(11) ?
C1 C2 C3 . . 111.17(8) ?
C1 C2 H21 . . 107.6(8) ?
C3 C2 H21 . . 112.8(8) ?
C1 C2 H22 . . 108.3(8) ?
C3 C2 H22 . . 109.6(8) ?
H21 C2 H22 . . 107.3(11) ?
C2 C3 C4 . . 110.34(8) ?
C2 C3 H32 . . 109.7(8) ?
C4 C3 H32 . . 110.2(8) ?
C2 C3 H31 . . 111.0(8) ?
C4 C3 H31 . . 109.3(8) ?
H32 C3 H31 . . 106.3(11) ?
C5 C4 C3 . . 110.40(8) ?
C5 C4 H41 . . 107.7(8) ?
C3 C4 H41 . . 110.7(8) ?
C5 C4 H42 . . 110.0(8) ?
C3 C4 H42 . . 109.4(8) ?
H41 C4 H42 . . 108.6(11) ?
N1 C5 C4 . . 109.91(7) ?
N1 C5 C6 . . 108.62(7) ?
C4 C5 C6 . . 115.06(7) ?
N1 C5 H52 . . 106.0(7) ?
C4 C5 H52 . . 110.1(7) ?
C6 C5 H52 . . 106.7(7) ?
O2 C6 O1 . . 125.38(8) ?
O2 C6 C5 . . 118.40(8) ?
O1 C6 C5 . . 116.16(8) ?
O4 O3 H3 . . 101.8(11) ?
O3 O4 H4 . . 101.7(10) ?
O6 O5 H5 . . 99.6(11) ?
O5 O6 H6 . . 100.4(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C5 . 1.4955(11) ?
N1 C1 . 1.4996(11) ?
N1 H1 . 0.912(15) ?
N1 H2 . 0.875(15) ?
O1 C6 . 1.2639(11) ?
O2 C6 . 1.2429(11) ?
C1 C2 . 1.5166(13) ?
C1 H11 . 0.958(13) ?
C1 H12 . 0.966(13) ?
C2 C3 . 1.5239(14) ?
C2 H21 . 0.968(14) ?
C2 H22 . 0.972(14) ?
C3 C4 . 1.5313(13) ?
C3 H32 . 0.974(14) ?
C3 H31 . 0.991(14) ?
C4 C5 . 1.5247(12) ?
C4 H41 . 0.986(14) ?
C4 H42 . 0.975(14) ?
C5 C6 . 1.5353(12) ?
C5 H52 . 0.991(12) ?
O3 O4 . 1.4600(9) ?
O3 H3 . 0.872(17) ?
O4 H4 . 0.866(18) ?
O5 O6 . 1.4646(11) ?
O5 H5 . 0.883(17) ?
O6 H6 . 0.881(16) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H3 O1 . 0.872(17) 1.819(17) 2.6463(10) 157.8(15) yes
O4 H4 O2 3_665 0.866(18) 1.889(18) 2.7490(10) 172.2(15) yes
O6 H6 O1 . 0.881(16) 1.760(16) 2.6412(10) 177.4(14) yes
O5 H5 O6 4_576 0.883(17) 1.898(18) 2.7777(12) 174.4(15) yes
N1 H1 O3 1_455 0.912(15) 1.961(15) 2.8336(11) 159.6(13) yes
N1 H2 O4 3_666 0.875(15) 2.112(15) 2.9459(11) 159.1(12) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 C2 . . . . -58.48(10) ?
N1 C1 C2 C3 . . . . 56.95(10) ?
C1 C2 C3 C4 . . . . -56.65(11) ?
C2 C3 C4 C5 . . . . 55.85(11) ?
C1 N1 C5 C4 . . . . 58.51(10) ?
C1 N1 C5 C6 . . . . -174.80(7) ?
C3 C4 C5 N1 . . . . -56.25(10) ?
C3 C4 C5 C6 . . . . -179.22(8) ?
N1 C5 C6 O2 . . . . 6.85(11) ?
C4 C5 C6 O2 . . . . 130.51(9) ?
N1 C5 C6 O1 . . . . -175.64(8) ?
C4 C5 C6 O1 . . . . -51.98(11) ?
H3 O3 O4 H4 . . . . 102.5(15) ?
H5 O5 O6 H6 . . . . -105.1(15) ?

_cod_database_fobs_code 2243499
