#------------------------------------------------------------------------------
#$Date: 2022-07-27 05:06:56 +0300 (Wed, 27 Jul 2022) $
#$Revision: 276956 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/41/2244132.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_2244132
loop_
_publ_author_name
'Shankara Prasad, Holehundi J.'
Devaraju
Vinaya
'Yathirajan, Hemmige S.'
'Parkin, Sean R.'
'Glidewell, Christopher'
_publ_section_title
;
 Syntheses and crystal structures of 4-(4-nitrophenyl)piperazin-1-ium
 benzoate monohydrate and 4-(4-nitrophenyl)piperazin-1-ium
 2-carboxy-4,6-dinitrophenolate
;
_journal_coeditor_code           HB8030
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022007472
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C10 H14 N3 O2 +, C7 H3 N2 O7 -'
_chemical_formula_moiety         'C10 H14 N3 O2 +, C7 H3 N2 O7 -'
_chemical_formula_sum            'C17 H17 N5 O9'
_chemical_formula_weight         435.35
_chemical_name_systematic
;
4-(4-Nitrophenyl)piperazin-1-ium 2-carboxy-4,6-dinitrophenolate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90.426(2)
_cell_angle_beta                 105.2730(10)
_cell_angle_gamma                98.538(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9599(4)
_cell_length_b                   8.5391(4)
_cell_length_c                   14.2227(5)
_cell_measurement_reflns_used    4212
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.510
_cell_measurement_theta_min      2.415
_cell_volume                     921.15(7)
_computing_cell_refinement
;
APEX3 (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
APEX3 (Bruker, 2016)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            38287
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         2.415
_diffrn_source                   microsource
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.180
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0293
_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)+(0.0290P)²+0.3527P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0772
_reflns_number_gt                3662
_reflns_number_total             4212
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb8030sup1.cif
_cod_data_source_block           II
_cod_database_code               2244132
_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   0.972
_shelx_estimated_absorpt_t_max   0.985
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 N11 0.30883(12) 0.10386(11) 0.64405(7) 0.01693(19) Uani d 1 . .
H H11 0.2967(17) 0.1840(17) 0.6040(10) 0.020 Uiso d 1 . .
H H12 0.2796(17) 0.0129(17) 0.6057(10) 0.020 Uiso d 1 . .
C C12 0.17915(14) 0.10314(13) 0.70340(8) 0.0188(2) Uani d 1 . .
H H12A 0.0579 0.0733 0.6608 0.023 Uiso calc 1 . .
H H12B 0.1890 0.2107 0.7328 0.023 Uiso calc 1 . .
C C13 0.21403(14) -0.01389(13) 0.78350(8) 0.0187(2) Uani d 1 . .
H H13A 0.1321 -0.0092 0.8248 0.022 Uiso calc 1 . .
H H13B 0.1931 -0.1229 0.7541 0.022 Uiso calc 1 . .
N N14 0.39625(12) 0.02405(11) 0.84356(6) 0.01699(19) Uani d 1 . .
C C15 0.51561(14) 0.00483(13) 0.78325(8) 0.0170(2) Uani d 1 . .
H H15A 0.4884 -0.1043 0.7536 0.020 Uiso calc 1 . .
H H15B 0.6388 0.0215 0.8245 0.020 Uiso calc 1 . .
C C16 0.49616(14) 0.12299(13) 0.70345(8) 0.0172(2) Uani d 1 . .
H H16A 0.5334 0.2322 0.7330 0.021 Uiso calc 1 . .
H H16B 0.5729 0.1055 0.6610 0.021 Uiso calc 1 . .
C C141 0.44287(14) 0.13710(12) 0.91966(7) 0.0156(2) Uani d 1 . .
C C142 0.31639(14) 0.18318(13) 0.96323(8) 0.0185(2) Uani d 1 . .
H H142 0.1955 0.1406 0.9370 0.022 Uiso calc 1 . .
C C143 0.36498(14) 0.28859(13) 1.04300(8) 0.0182(2) Uani d 1 . .
H H143 0.2783 0.3179 1.0717 0.022 Uiso calc 1 . .
C C144 0.54137(14) 0.35176(12) 1.08126(7) 0.0161(2) Uani d 1 . .
C C145 0.66886(14) 0.31362(13) 1.03852(8) 0.0173(2) Uani d 1 . .
H H145 0.7887 0.3601 1.0640 0.021 Uiso calc 1 . .
C C146 0.62025(14) 0.20794(13) 0.95897(8) 0.0174(2) Uani d 1 . .
H H146 0.7078 0.1821 0.9299 0.021 Uiso calc 1 . .
N N144 0.59245(12) 0.46290(11) 1.16455(6) 0.01728(19) Uani d 1 . .
O O141 0.47859(11) 0.49209(10) 1.20379(6) 0.02406(19) Uani d 1 . .
O O142 0.74805(11) 0.52457(10) 1.19410(6) 0.02329(18) Uani d 1 . .
C C21 0.24532(14) 0.43648(13) 0.46951(8) 0.0171(2) Uani d 1 . .
C C22 0.20094(14) 0.59329(12) 0.45355(8) 0.0168(2) Uani d 1 . .
C C23 0.15472(14) 0.65011(13) 0.36161(8) 0.0163(2) Uani d 1 . .
H H23 0.1308 0.7557 0.3537 0.020 Uiso calc 1 . .
C C24 0.14290(14) 0.55395(13) 0.28038(8) 0.0164(2) Uani d 1 . .
C C25 0.17807(14) 0.40041(13) 0.28998(8) 0.0165(2) Uani d 1 . .
H H25 0.1656 0.3340 0.2339 0.020 Uiso calc 1 . .
C C26 0.23134(14) 0.34521(12) 0.38199(8) 0.0162(2) Uani d 1 . .
O O21 0.28898(12) 0.38660(9) 0.55580(6) 0.02378(19) Uani d 1 . .
C C27 0.20933(15) 0.70160(13) 0.53734(8) 0.0199(2) Uani d 1 . .
O O271 0.16416(12) 0.83252(9) 0.52573(6) 0.02424(19) Uani d 1 . .
O O272 0.26860(13) 0.65093(10) 0.62536(6) 0.0294(2) Uani d 1 . .
H H272 0.288(2) 0.540(2) 0.6144(12) 0.044 Uiso d 1 . .
N N24 0.09824(12) 0.61730(11) 0.18421(7) 0.01767(19) Uani d 1 . .
O O241 0.08439(11) 0.75980(9) 0.17920(6) 0.02152(18) Uani d 1 . .
O O242 0.07873(11) 0.52884(10) 0.11242(6) 0.02219(18) Uani d 1 . .
N N26 0.27842(12) 0.18676(11) 0.38689(7) 0.01824(19) Uani d 1 . .
O O261 0.20718(11) 0.09218(9) 0.31673(6) 0.02451(19) Uani d 1 . .
O O262 0.38998(12) 0.15381(10) 0.45879(6) 0.02596(19) Uani 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
C16 N11 C12 . . 113.90(8) ?
C16 N11 H11 . . 108.4(9) ?
C12 N11 H11 . . 108.3(9) ?
C16 N11 H12 . . 111.0(8) ?
C12 N11 H12 . . 108.3(9) ?
H11 N11 H12 . . 106.8(12) ?
N11 C12 C13 . . 110.16(9) ?
N11 C12 H12A . . 109.6 ?
C13 C12 H12A . . 109.6 ?
N11 C12 H12B . . 109.6 ?
C13 C12 H12B . . 109.6 ?
H12A C12 H12B . . 108.1 ?
N14 C13 C12 . . 109.99(9) ?
N14 C13 H13A . . 109.7 ?
C12 C13 H13A . . 109.7 ?
N14 C13 H13B . . 109.7 ?
C12 C13 H13B . . 109.7 ?
H13A C13 H13B . . 108.2 ?
C141 N14 C15 . . 121.02(9) ?
C141 N14 C13 . . 121.10(9) ?
C15 N14 C13 . . 109.06(8) ?
N14 C15 C16 . . 110.28(9) ?
N14 C15 H15A . . 109.6 ?
C16 C15 H15A . . 109.6 ?
N14 C15 H15B . . 109.6 ?
C16 C15 H15B . . 109.6 ?
H15A C15 H15B . . 108.1 ?
N11 C16 C15 . . 109.87(9) ?
N11 C16 H16A . . 109.7 ?
C15 C16 H16A . . 109.7 ?
N11 C16 H16B . . 109.7 ?
C15 C16 H16B . . 109.7 ?
H16A C16 H16B . . 108.2 ?
N14 C141 C142 . . 121.47(10) ?
N14 C141 C146 . . 121.20(10) ?
C142 C141 C146 . . 117.30(10) ?
C143 C142 C141 . . 121.27(10) ?
C143 C142 H142 . . 119.4 ?
C141 C142 H142 . . 119.4 ?
C142 C143 C144 . . 119.59(10) ?
C142 C143 H143 . . 120.2 ?
C144 C143 H143 . . 120.2 ?
C145 C144 C143 . . 120.87(10) ?
C145 C144 N144 . . 119.43(10) ?
C143 C144 N144 . . 119.67(10) ?
C146 C145 C144 . . 119.48(10) ?
C146 C145 H145 . . 120.3 ?
C144 C145 H145 . . 120.3 ?
C145 C146 C141 . . 121.42(10) ?
C145 C146 H146 . . 119.3 ?
C141 C146 H146 . . 119.3 ?
O142 N144 O141 . . 122.45(9) ?
O142 N144 C144 . . 118.77(9) ?
O141 N144 C144 . . 118.78(9) ?
O21 C21 C26 . . 124.86(10) ?
O21 C21 C22 . . 120.75(9) ?
C26 C21 C22 . . 114.38(9) ?
C23 C22 C21 . . 121.89(10) ?
C23 C22 C27 . . 117.59(10) ?
C21 C22 C27 . . 120.49(10) ?
C22 C23 C24 . . 120.26(10) ?
C22 C23 H23 . . 119.9 ?
C24 C23 H23 . . 119.9 ?
C25 C24 C23 . . 120.99(10) ?
C25 C24 N24 . . 119.55(9) ?
C23 C24 N24 . . 119.43(10) ?
C26 C25 C24 . . 118.95(10) ?
C26 C25 H25 . . 120.5 ?
C24 C25 H25 . . 120.5 ?
C25 C26 C21 . . 123.45(10) ?
C25 C26 N26 . . 115.98(9) ?
C21 C26 N26 . . 120.55(9) ?
O271 C27 O272 . . 121.14(10) ?
O271 C27 C22 . . 121.85(10) ?
O272 C27 C22 . . 117.01(10) ?
C27 O272 H272 . . 105.0(10) ?
O242 N24 O241 . . 123.40(9) ?
O242 N24 C24 . . 118.92(9) ?
O241 N24 C24 . . 117.67(9) ?
O262 N26 O261 . . 122.85(9) ?
O262 N26 C26 . . 119.17(9) ?
O261 N26 C26 . . 117.95(9) ?
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
N11 C16 . 1.4919(14) ?
N11 C12 . 1.4951(14) ?
N11 H11 . 0.894(14) ?
N11 H12 . 0.910(14) ?
C12 C13 . 1.5187(15) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 N14 . 1.4635(14) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
N14 C141 . 1.3812(13) ?
N14 C15 . 1.4625(14) ?
C15 C16 . 1.5169(15) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C141 C142 . 1.4125(15) ?
C141 C146 . 1.4133(15) ?
C142 C143 . 1.3774(15) ?
C142 H142 . 0.9500 ?
C143 C144 . 1.3881(15) ?
C143 H143 . 0.9500 ?
C144 C145 . 1.3875(15) ?
C144 N144 . 1.4437(13) ?
C145 C146 . 1.3765(15) ?
C145 H145 . 0.9500 ?
C146 H146 . 0.9500 ?
N144 O142 . 1.2315(12) ?
N144 O141 . 1.2355(12) ?
C21 O21 . 1.2788(13) ?
C21 C26 . 1.4340(15) ?
C21 C22 . 1.4394(15) ?
C22 C23 . 1.3747(15) ?
C22 C27 . 1.4844(15) ?
C23 C24 . 1.3869(15) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.3811(15) ?
C24 N24 . 1.4498(13) ?
C25 C26 . 1.3750(15) ?
C25 H25 . 0.9500 ?
C26 N26 . 1.4540(14) ?
C27 O271 . 1.2236(14) ?
C27 O272 . 1.3171(14) ?
O272 H272 . 1.003(18) ?
N24 O242 . 1.2277(12) ?
N24 O241 . 1.2389(12) ?
N26 O262 . 1.2303(12) ?
N26 O261 . 1.2343(12) ?
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
N11 H11 O21 . 0.894(14) 1.869(14) 2.7356(12) 162.8(13) y
N11 H11 O262 . 0.894(14) 2.396(14) 2.8937(13) 115.4(11) y
N11 H12 O271 1_545 0.910(14) 1.874(14) 2.7668(12) 166.2(12) y
O272 H272 O21 . 1.000(17) 1.549(17) 2.5020(12) 157.4(15) y
C12 H12B O142 2_667 0.99 2.41 3.3921(14) 173 y
C16 H16A O141 2_667 0.99 2.54 3.4906(14) 161 y
C145 H145 O242 1_656 0.95 2.46 3.3927(15) 168 y
C146 H146 O241 2_666 0.95 2.55 3.4227(15) 153 y
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
C16 N11 C12 C13 . . . . -50.40(12) ?
N11 C12 C13 N14 . . . . 56.08(11) ?
C12 C13 N14 C141 . . . . 84.07(12) ?
C12 C13 N14 C15 . . . . -63.61(11) ?
C141 N14 C15 C16 . . . . -83.73(12) ?
C13 N14 C15 C16 . . . . 63.98(11) ?
C12 N11 C16 C15 . . . . 50.41(11) ?
N14 C15 C16 N11 . . . . -56.47(11) ?
C15 N14 C141 C142 . . . . 164.67(10) ?
C13 N14 C141 C142 . . . . 20.80(15) ?
C15 N14 C141 C146 . . . . -17.23(15) ?
C13 N14 C141 C146 . . . . -161.10(10) ?
N14 C141 C142 C143 . . . . 175.90(10) ?
C146 C141 C142 C143 . . . . -2.27(16) ?
C141 C142 C143 C144 . . . . 0.36(16) ?
C142 C143 C144 C145 . . . . 1.84(16) ?
C142 C143 C144 N144 . . . . 179.67(10) ?
C143 C144 C145 C146 . . . . -2.02(16) ?
N144 C144 C145 C146 . . . . -179.86(10) ?
C144 C145 C146 C141 . . . . 0.00(16) ?
N14 C141 C146 C145 . . . . -176.08(10) ?
C142 C141 C146 C145 . . . . 2.09(16) ?
C145 C144 N144 O142 . . . . 1.91(15) ?
C143 C144 N144 O142 . . . . -175.95(10) ?
C145 C144 N144 O141 . . . . -177.77(10) ?
C143 C144 N144 O141 . . . . 4.37(15) ?
O21 C21 C22 C23 . . . . 179.56(10) ?
C26 C21 C22 C23 . . . . -1.93(15) ?
O21 C21 C22 C27 . . . . 1.51(16) ?
C26 C21 C22 C27 . . . . -179.98(10) ?
C21 C22 C23 C24 . . . . 2.55(16) ?
C27 C22 C23 C24 . . . . -179.35(10) ?
C22 C23 C24 C25 . . . . -0.39(16) ?
C22 C23 C24 N24 . . . . -178.48(9) ?
C23 C24 C25 C26 . . . . -2.25(16) ?
N24 C24 C25 C26 . . . . 175.84(9) ?
C24 C25 C26 C21 . . . . 2.85(16) ?
C24 C25 C26 N26 . . . . -175.67(9) ?
O21 C21 C26 C25 . . . . 177.64(10) ?
C22 C21 C26 C25 . . . . -0.79(16) ?
O21 C21 C26 N26 . . . . -3.90(17) ?
C22 C21 C26 N26 . . . . 177.67(9) ?
C23 C22 C27 O271 . . . . 5.49(17) ?
C21 C22 C27 O271 . . . . -176.38(10) ?
C23 C22 C27 O272 . . . . -174.21(10) ?
C21 C22 C27 O272 . . . . 3.93(16) ?
C25 C24 N24 O242 . . . . 5.79(14) ?
C23 C24 N24 O242 . . . . -176.09(9) ?
C25 C24 N24 O241 . . . . -173.14(9) ?
C23 C24 N24 O241 . . . . 4.98(14) ?
C25 C26 N26 O262 . . . . 150.18(10) ?
C21 C26 N26 O262 . . . . -28.38(15) ?
C25 C26 N26 O261 . . . . -27.86(14) ?
C21 C26 N26 O261 . . . . 153.57(10) ?

_cod_database_fobs_code 2244132
