#------------------------------------------------------------------------------
#$Date: 2022-04-27 04:54:03 +0300 (Wed, 27 Apr 2022) $
#$Revision: 274714 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/40/2244077.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_2244077
loop_
_publ_author_name
'Mahesha, Ninganayaka'
'Kiran Kumar, Haruvegowda'
'Yathirajan, Hemmige S.'
'Foro, Sabine'
'Abdelbaky, Mohammed S. M.'
'Garcia-Granda, Santiago'
_publ_section_title
;
 Crystal structures of six 4-(4-nitrophenyl)piperazin-1-ium salts
;
_journal_coeditor_code           EX2056
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022004157
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C10 H14 N3 O2 +, C7 H5 O3 -, H2 O'
_chemical_formula_moiety         'C10 H14 N3 O2 +, C7 H5 O3 -, H2 O'
_chemical_formula_sum            'C17 H21 N3 O6'
_chemical_formula_weight         363.37
_chemical_name_systematic
;
4-(4-Nitrophenyl)piperazin-1-ium 4-hydroxybenzoate monohydrate
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                103.900(10)
_cell_angle_beta                 108.320(10)
_cell_angle_gamma                112.960(10)
_cell_formula_units_Z            2
_cell_length_a                   9.6360(10)
_cell_length_b                   10.3010(10)
_cell_length_c                   10.8670(10)
_cell_measurement_reflns_used    5342
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.342
_cell_measurement_theta_min      2.580
_cell_volume                     857.8(2)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL-2014 (Sheldrick, 2015b), PLATON (Spek, 2020) and publCIF
(Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Sapphire CCD'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0127
_diffrn_reflns_av_unetI/netI     0.023
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5342
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.342
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.194
_refine_ls_extinction_coef       0.032(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018/3 (Sheldrick 2015b)
;
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3135
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0386P)²+0.3231P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1058
_reflns_number_gt                2342
_reflns_number_total             3140
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ex2056sup1.cif
_cod_data_source_block           III
_cod_original_cell_volume        857.80(17)
_cod_database_code               2244077
loop_
_symmetry_equiv_pos_as_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
C C1 0.3138(2) 0.37000(19) 0.65529(18) 0.0346(4) Uani d 1 . .
C C2 0.1431(2) 0.2527(2) 0.57638(19) 0.0418(4) Uani d 1 . .
H H2 0.068235 0.250847 0.613904 0.05 Uiso calc 1 . .
C C3 0.0843(2) 0.1407(2) 0.4450(2) 0.0434(5) Uani d 1 . .
H H3 -0.029409 0.063818 0.39416 0.052 Uiso calc 1 . .
C C4 0.1942(2) 0.1428(2) 0.38907(19) 0.0411(4) Uani d 1 . .
C C5 0.3624(2) 0.2553(2) 0.4636(2) 0.0483(5) Uani d 1 . .
H H5 0.436252 0.255393 0.42532 0.058 Uiso calc 1 . .
C C6 0.4208(2) 0.3670(2) 0.5942(2) 0.0472(5) Uani d 1 . .
H H6 0.53484 0.443048 0.64379 0.057 Uiso calc 1 . .
C C7 0.5230(2) 0.6338(2) 0.8284(2) 0.0453(5) Uani d 1 . .
H H7A 0.489341 0.67826 0.763471 0.054 Uiso calc 1 . .
H H7B 0.611237 0.616548 0.817407 0.054 Uiso calc 1 . .
C C8 0.5933(2) 0.7472(2) 0.9784(2) 0.0493(5) Uani d 1 . .
H H8A 0.643572 0.71093 1.044494 0.059 Uiso calc 1 . .
H H8B 0.681545 0.846719 0.99504 0.059 Uiso calc 1 . .
C C9 0.3302(3) 0.6143(2) 0.9836(2) 0.0457(5) Uani d 1 . .
H H9A 0.242868 0.625614 1.002896 0.055 Uiso calc 1 . .
H H9B 0.381743 0.579404 1.050389 0.055 Uiso calc 1 . .
C C10 0.2514(2) 0.4953(2) 0.83370(19) 0.0403(4) Uani d 1 . .
H H10A 0.176601 0.394834 0.82667 0.048 Uiso calc 1 . .
H H10B 0.183115 0.521491 0.76885 0.048 Uiso calc 1 . .
C C11 0.1749(2) 0.5843(2) 0.29147(19) 0.0418(5) Uani d 1 . .
C C12 0.2469(3) 0.7413(2) 0.3258(2) 0.0495(5) Uani d 1 . .
H H12 0.262285 0.778209 0.258209 0.059 Uiso calc 1 . .
C C13 0.2959(2) 0.8431(2) 0.4597(2) 0.0438(5) Uani d 1 . .
H H13 0.344454 0.94863 0.481898 0.053 Uiso calc 1 . .
C C14 0.2738(2) 0.7906(2) 0.56226(18) 0.0364(4) Uani d 1 . .
C C15 0.2004(2) 0.6329(2) 0.52544(19) 0.0395(4) Uani d 1 . .
H H15 0.18337 0.595519 0.592378 0.047 Uiso calc 1 . .
C C16 0.1520(2) 0.5299(2) 0.39188(19) 0.0410(4) Uani d 1 . .
H H16 0.104259 0.424435 0.369591 0.049 Uiso calc 1 . .
C C17 0.3293(2) 0.9024(2) 0.7080(2) 0.0440(5) Uani d 1 . .
N N1 0.37669(18) 0.48418(16) 0.78933(15) 0.0372(4) Uani d 1 . .
N N2 0.4599(2) 0.76559(19) 1.00415(18) 0.0479(4) Uani d 1 . .
N N3 0.1322(2) 0.02537(19) 0.25010(18) 0.0518(4) Uani d 1 . .
O O1 0.2282(2) 0.04014(19) 0.19537(17) 0.0759(5) Uani d 1 . .
O O2 -0.0112(2) -0.08579(18) 0.19233(16) 0.0715(5) Uani d 1 . .
O O3 0.1311(2) 0.48813(18) 0.15852(15) 0.0637(4) Uani d 1 . .
O O4 0.3985(2) 1.04290(17) 0.73256(16) 0.0744(5) Uani d 1 . .
O O5 0.30323(18) 0.85085(16) 0.79750(14) 0.0547(4) Uani d 1 . .
O O6 -0.0679(3) 0.1917(2) 0.09903(19) 0.0809(6) Uani d 1 . .
H H21 0.412(3) 0.796(3) 0.941(2) 0.097 Uiso d 1 . .
H H22 0.513(3) 0.838(3) 1.099(2) 0.097 Uiso d 1 . .
H H17 0.070(3) 0.394(2) 0.143(3) 0.097 Uiso d 1 . .
H H1W -0.140(3) 0.168(3) 0.129(3) 0.097 Uiso d 1 . .
H H2W -0.112(3) 0.128(3) 0.015(2) 0.097 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 0 '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 0.006 '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
N1 C1 C6 . . 120.65(15) ?
N1 C1 C2 . . 122.40(15) ?
C6 C1 C2 . . 116.95(16) ?
C3 C2 C1 . . 121.37(17) ?
C3 C2 H2 . . 119.3 ?
C1 C2 H2 . . 119.3 ?
C2 C3 C4 . . 119.60(17) ?
C2 C3 H3 . . 120.2 ?
C4 C3 H3 . . 120.2 ?
C3 C4 C5 . . 120.68(17) ?
C3 C4 N3 . . 119.73(17) ?
C5 C4 N3 . . 119.59(17) ?
C6 C5 C4 . . 119.67(17) ?
C6 C5 H5 . . 120.2 ?
C4 C5 H5 . . 120.2 ?
C5 C6 C1 . . 121.72(17) ?
C5 C6 H6 . . 119.1 ?
C1 C6 H6 . . 119.1 ?
N1 C7 C8 . . 113.07(16) ?
N1 C7 H7A . . 109 ?
C8 C7 H7A . . 109 ?
N1 C7 H7B . . 109 ?
C8 C7 H7B . . 109 ?
H7A C7 H7B . . 107.8 ?
N2 C8 C7 . . 110.93(16) ?
N2 C8 H8A . . 109.5 ?
C7 C8 H8A . . 109.5 ?
N2 C8 H8B . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 108 ?
N2 C9 C10 . . 110.96(15) ?
N2 C9 H9A . . 109.4 ?
C10 C9 H9A . . 109.4 ?
N2 C9 H9B . . 109.4 ?
C10 C9 H9B . . 109.4 ?
H9A C9 H9B . . 108 ?
N1 C10 C9 . . 113.15(15) ?
N1 C10 H10A . . 108.9 ?
C9 C10 H10A . . 108.9 ?
N1 C10 H10B . . 108.9 ?
C9 C10 H10B . . 108.9 ?
H10A C10 H10B . . 107.8 ?
O3 C11 C16 . . 122.11(17) ?
O3 C11 C12 . . 118.10(17) ?
C16 C11 C12 . . 119.78(17) ?
C13 C12 C11 . . 120.14(18) ?
C13 C12 H12 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
C12 C13 C14 . . 120.94(17) ?
C12 C13 H13 . . 119.5 ?
C14 C13 H13 . . 119.5 ?
C15 C14 C13 . . 118.02(16) ?
C15 C14 C17 . . 121.42(16) ?
C13 C14 C17 . . 120.55(16) ?
C16 C15 C14 . . 121.51(17) ?
C16 C15 H15 . . 119.2 ?
C14 C15 H15 . . 119.2 ?
C15 C16 C11 . . 119.60(17) ?
C15 C16 H16 . . 120.2 ?
C11 C16 H16 . . 120.2 ?
O4 C17 O5 . . 124.14(18) ?
O4 C17 C14 . . 116.82(17) ?
O5 C17 C14 . . 119.04(17) ?
C1 N1 C10 . . 116.66(14) ?
C1 N1 C7 . . 115.79(14) ?
C10 N1 C7 . . 114.73(14) ?
C8 N2 C9 . . 108.67(15) ?
C8 N2 H21 . . 109.1(18) ?
C9 N2 H21 . . 108.9(18) ?
C8 N2 H22 . . 106.2(17) ?
C9 N2 H22 . . 110.8(17) ?
H21 N2 H22 . . 113(2) ?
O2 N3 O1 . . 122.24(17) ?
O2 N3 C4 . . 119.43(17) ?
O1 N3 C4 . . 118.32(17) ?
C11 O3 H17 . . 110.2(19) ?
H1W O6 H2W . . 108(3) ?
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
C1 N1 . 1.392(2) ?
C1 C6 . 1.397(2) ?
C1 C2 . 1.402(2) ?
C2 C3 . 1.371(3) ?
C2 H2 . 0.93 ?
C3 C4 . 1.373(3) ?
C3 H3 . 0.93 ?
C4 C5 . 1.373(3) ?
C4 N3 . 1.446(2) ?
C5 C6 . 1.365(3) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 N1 . 1.468(2) ?
C7 C8 . 1.501(3) ?
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
C8 N2 . 1.470(3) ?
C8 H8A . 0.97 ?
C8 H8B . 0.97 ?
C9 N2 . 1.476(2) ?
C9 C10 . 1.507(3) ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
C10 N1 . 1.467(2) ?
C10 H10A . 0.97 ?
C10 H10B . 0.97 ?
C11 O3 . 1.360(2) ?
C11 C16 . 1.379(3) ?
C11 C12 . 1.382(3) ?
C12 C13 . 1.374(3) ?
C12 H12 . 0.93 ?
C13 C14 . 1.389(2) ?
C13 H13 . 0.93 ?
C14 C15 . 1.383(2) ?
C14 C17 . 1.494(3) ?
C15 C16 . 1.378(2) ?
C15 H15 . 0.93 ?
C16 H16 . 0.93 ?
C17 O4 . 1.250(2) ?
C17 O5 . 1.260(2) ?
N2 H21 . 0.893(17) ?
N2 H22 . 0.935(17) ?
N3 O2 . 1.221(2) ?
N3 O1 . 1.230(2) ?
O3 H17 . 0.850(17) ?
O6 H1W . 0.832(17) ?
O6 H2W . 0.834(17) ?
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
N2 H21 O5 . 0.893(17) 1.926(17) 2.819(2) 177(3) yes
N2 H22 O4 2_677 0.935(17) 1.649(17) 2.583(2) 177(3) yes
O3 H17 O6 . 0.850(17) 1.820(17) 2.669(2) 177(3) yes
O6 H1W O5 2_566 0.832(17) 1.946(18) 2.768(2) 169(3) yes
O6 H2W O1 2 0.834(17) 2.111(18) 2.944(2) 178(3) 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
N1 C1 C2 C3 . . . . -179.46(17) ?
C6 C1 C2 C3 . . . . -0.3(3) ?
C1 C2 C3 C4 . . . . 0.0(3) ?
C2 C3 C4 C5 . . . . 0.4(3) ?
C2 C3 C4 N3 . . . . -179.58(17) ?
C3 C4 C5 C6 . . . . -0.5(3) ?
N3 C4 C5 C6 . . . . 179.41(18) ?
C4 C5 C6 C1 . . . . 0.3(3) ?
N1 C1 C6 C5 . . . . 179.30(18) ?
C2 C1 C6 C5 . . . . 0.1(3) ?
N1 C7 C8 N2 . . . . -53.2(2) ?
N2 C9 C10 N1 . . . . 52.1(2) ?
O3 C11 C12 C13 . . . . -178.90(18) ?
C16 C11 C12 C13 . . . . 0.1(3) ?
C11 C12 C13 C14 . . . . -0.2(3) ?
C12 C13 C14 C15 . . . . -0.3(3) ?
C12 C13 C14 C17 . . . . 179.26(18) ?
C13 C14 C15 C16 . . . . 0.8(3) ?
C17 C14 C15 C16 . . . . -178.76(17) ?
C14 C15 C16 C11 . . . . -0.8(3) ?
O3 C11 C16 C15 . . . . 179.34(17) ?
C12 C11 C16 C15 . . . . 0.4(3) ?
C15 C14 C17 O4 . . . . 178.09(18) ?
C13 C14 C17 O4 . . . . -1.4(3) ?
C15 C14 C17 O5 . . . . -2.4(3) ?
C13 C14 C17 O5 . . . . 178.03(18) ?
C6 C1 N1 C10 . . . . 169.31(17) ?
C2 C1 N1 C10 . . . . -11.5(2) ?
C6 C1 N1 C7 . . . . 29.6(2) ?
C2 C1 N1 C7 . . . . -151.19(18) ?
C9 C10 N1 C1 . . . . 176.12(15) ?
C9 C10 N1 C7 . . . . -43.8(2) ?
C8 C7 N1 C1 . . . . -175.25(16) ?
C8 C7 N1 C10 . . . . 44.3(2) ?
C7 C8 N2 C9 . . . . 61.2(2) ?
C10 C9 N2 C8 . . . . -60.7(2) ?
C3 C4 N3 O2 . . . . -9.7(3) ?
C5 C4 N3 O2 . . . . 170.3(2) ?
C3 C4 N3 O1 . . . . 171.61(19) ?
C5 C4 N3 O1 . . . . -8.3(3) ?

_cod_database_fobs_code 2244077
