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#$Date: 2022-07-08 10:07:36 +0300 (Fri, 08 Jul 2022) $
#$Revision: 276735 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/56/8105664.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_8105664
loop_
_publ_author_name
'Yunlu, Li'
'Mei, Xue'
'Jianlong, Wang'
'Luyao, Zhang'
'Jie, Ning'
_publ_section_title
;
 The crystal structure of 1,4-dinitro-2,3,5,6-tetraacetoxy-piperazine,
 C12H16N4O12
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              417
_journal_page_last               418
_journal_paper_doi               10.1515/ncrs-2018-0423
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C12 H16 N4 O12'
_chemical_formula_sum            'C12 H16 N4 O12'
_chemical_formula_weight         408.29
_chemical_name_systematic
;
1,4-dinitro-2,3,5,6-tetraacetoxy-piperazine
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           55
_space_group_name_Hall           '-P 2 2ab'
_space_group_name_H-M_alt        'P b a m'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0836(17)
_cell_length_b                   8.0165(7)
_cell_length_c                   14.7754(15)
_cell_measurement_reflns_used    1234
_cell_measurement_temperature    173
_cell_measurement_theta_max      24.63
_cell_measurement_theta_min      2.76
_cell_volume                     1905.1(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009) [10]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009) [10]'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015) [9]'
_computing_structure_solution    'ShelXT (Sheldrick, 2015) [8]'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6208
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.316
_diffrn_reflns_theta_min         2.757
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker;SADABS;2014
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0499
_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)+(0.0724P)²+1.1203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1606
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1064
_reflns_number_total             1808
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0423_suppl.cif
_cod_data_source_block           1
_cod_database_code               8105664
_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   0.968
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'
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
C1A C 0.45236(18) 0.5000(4) 0.08493(18) 0.0344(7) Uani 1 1 d . . . . .
H1A H 0.4310 0.4308 0.1362 0.041 Uiso 1 1 calc R . . . .
C2A C 0.3870(2) 0.7102(4) 0.1742(2) 0.0410(8) Uani 1 1 d . . . . .
C3A C 0.3712(2) 0.8914(4) 0.1779(2) 0.0564(10) Uani 1 1 d . . . . .
H3AA H 0.4087 0.9429 0.2222 0.085 Uiso 1 1 calc GR . . . .
H3AB H 0.3134 0.9114 0.1959 0.085 Uiso 1 1 calc GR . . . .
H3AC H 0.3812 0.9404 0.1181 0.085 Uiso 1 1 calc GR . . . .
C1B C 0.49881(19) 0.5944(3) 0.41559(17) 0.0334(7) Uani 1 1 d . . . . .
H1B H 0.4643 0.6354 0.3639 0.040 Uiso 1 1 calc R . . . .
C2B C 0.6037(2) 0.7272(4) 0.3263(2) 0.0379(8) Uani 1 1 d . . . . .
C3B C 0.6931(2) 0.7720(4) 0.3263(3) 0.0562(10) Uani 1 1 d . . . . .
H3BA H 0.7024 0.8645 0.3685 0.084 Uiso 1 1 calc GR . . . .
H3BB H 0.7098 0.8059 0.2653 0.084 Uiso 1 1 calc GR . . . .
H3BC H 0.7260 0.6753 0.3453 0.084 Uiso 1 1 calc GR . . . .
N1A N 0.4226(2) 0.4344(4) 0.0000 0.0349(8) Uani 1 2 d S T P . .
N2A N 0.3420(3) 0.3688(5) 0.0000 0.0518(11) Uani 1 2 d S T P . .
O3A O 0.42633(13) 0.6693(2) 0.09543(12) 0.0394(6) Uani 1 1 d . . . . .
N1B N 0.4649(2) 0.6537(4) 0.5000 0.0325(8) Uani 1 2 d S T P . .
N2B N 0.4336(3) 0.8168(5) 0.5000 0.0465(10) Uani 1 2 d S T P . .
O3B O 0.58290(12) 0.6524(2) 0.40608(12) 0.0370(6) Uani 1 1 d . . . . .
O1A O 0.31051(17) 0.3396(4) 0.07333(17) 0.0748(9) Uani 1 1 d . . . . .
O2A O 0.36960(14) 0.6085(3) 0.23149(15) 0.0514(7) Uani 1 1 d . . . . .
O1B O 0.42011(18) 0.8797(3) 0.42660(16) 0.0659(8) Uani 1 1 d . . . . .
O2B O 0.55467(15) 0.7516(3) 0.26650(14) 0.0472(6) Uani 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'
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
C1A C1A H1A 110.1 2_665 .
N1A C1A C1A 109.38(19) . 2_665
N1A C1A H1A 110.1 . .
O3A C1A C1A 107.0(3) . 2_665
O3A C1A H1A 110.1 . .
O3A C1A N1A 110.1(2) . .
O3A C2A C3A 110.3(3) . .
O2A C2A C3A 126.8(3) . .
O2A C2A O3A 122.8(3) . .
C2A C3A H3AA 109.5 . .
C2A C3A H3AB 109.5 . .
C2A C3A H3AC 109.5 . .
H3AA C3A H3AB 109.5 . .
H3AA C3A H3AC 109.5 . .
H3AB C3A H3AC 109.5 . .
C1B C1B H1B 110.0 2_665 .
N1B C1B C1B 109.81(19) . 2_665
N1B C1B H1B 110.0 . .
O3B C1B C1B 107.4(3) . 2_665
O3B C1B H1B 110.0 . .
O3B C1B N1B 109.5(2) . .
O3B C2B C3B 110.1(3) . .
O2B C2B C3B 126.7(3) . .
O2B C2B O3B 123.2(3) . .
C2B C3B H3BA 109.5 . .
C2B C3B H3BB 109.5 . .
C2B C3B H3BC 109.5 . .
H3BA C3B H3BB 109.5 . .
H3BA C3B H3BC 109.5 . .
H3BB C3B H3BC 109.5 . .
C1A N1A C1A 121.0(3) . 6
N2A N1A C1A 116.39(18) . 6
N2A N1A C1A 116.38(18) . .
O1A N2A N1A 117.2(2) . .
O1A N2A N1A 117.2(2) 6 .
O1A N2A O1A 125.5(4) . 6
C2A O3A C1A 117.2(2) . .
C1B N1B C1B 119.8(3) . 6_556
N2B N1B C1B 116.32(17) . .
N2B N1B C1B 116.32(17) . 6_556
O1B N2B N1B 116.8(2) . .
O1B N2B N1B 116.8(2) 6_556 .
O1B N2B O1B 126.3(4) . 6_556
C2B O3B C1B 117.2(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1A C1A 1.532(6) 2_665
C1A H1A 1.0000 .
C1A N1A 1.442(3) .
C1A O3A 1.429(3) .
C2A C3A 1.476(5) .
C2A O3A 1.366(3) .
C2A O2A 1.208(4) .
C3A H3AA 0.9800 .
C3A H3AB 0.9800 .
C3A H3AC 0.9800 .
C1B C1B 1.515(5) 2_665
C1B H1B 1.0000 .
C1B N1B 1.442(3) .
C1B O3B 1.437(3) .
C2B C3B 1.482(5) .
C2B O3B 1.364(3) .
C2B O2B 1.200(4) .
C3B H3BA 0.9800 .
C3B H3BB 0.9800 .
C3B H3BC 0.9800 .
N1A C1A 1.442(3) 6
N1A N2A 1.399(5) .
N2A O1A 1.219(3) 6
N2A O1A 1.219(3) .
N1B C1B 1.442(3) 6_556
N1B N2B 1.401(5) .
N2B O1B 1.216(3) .
N2B O1B 1.216(3) 6_556
