#------------------------------------------------------------------------------
#$Date: 2022-11-08 21:40:59 +0200 (Tue, 08 Nov 2022) $
#$Revision: 279115 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/41/2244170.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_2244170
loop_
_publ_author_name
'Archana, Sreeramapura D.'
'Kiran Kumar, Haruvegowda'
'Yathirajan, Hemmige S.'
'Foro, Sabine'
'Butcher, Ray J.'
_publ_section_title
;
 The structures of eleven (4-phenyl)piperazinium salts containing organic
 anions
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1016
_journal_page_last               1027
_journal_paper_doi               10.1107/S2056989022009057
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C10 H15 N2 +, C7 H5 O2 -, H2 O'
_chemical_formula_moiety         'C10 H15 N2 +, C7 H5 O2 -, H2 O'
_chemical_formula_sum            'C17 H22 N2 O3'
_chemical_formula_weight         302.36
_chemical_name_systematic
;
4-Phenylpiperazin-1-ium benzoate monohydrate
;
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 93.83(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.202(2)
_cell_length_b                   34.573(9)
_cell_length_c                   7.596(2)
_cell_measurement_reflns_used    885
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.75
_cell_measurement_theta_min      2.74
_cell_volume                     1625.1(8)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2007)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2007)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2007)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur with Sapphire CCD
;
_diffrn_measurement_method
;
ω and φ scans
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6075
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.789
_diffrn_reflns_theta_min         2.935
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysalisRED; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_description       rod
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3492
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.947
_refine_ls_R_factor_all          0.1824
_refine_ls_R_factor_gt           0.0649
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0549P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1437
_reflns_number_gt                1387
_reflns_number_total             3492
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb8034sup1.cif
_cod_data_source_block           9
_cod_depositor_comments
'Adding full bibliography for 2244163--2244173.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2244170
_cod_database_fobs_code          2244170
_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   0.973
_shelx_estimated_absorpt_t_max   0.987
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 0.2813(3) 0.60989(6) 0.7704(3) 0.0434(6) Uani d 1 . .
N N2 0.2143(4) 0.52769(7) 0.7340(3) 0.0540(7) Uani d 1 . .
H H21 0.175(4) 0.5046(6) 0.776(3) 0.065 Uiso d 1 . .
H H22 0.244(4) 0.5249(8) 0.621(2) 0.065 Uiso d 1 . .
C C1 0.3322(4) 0.64902(8) 0.7364(3) 0.0458(7) Uani d 1 . .
C C2 0.1985(5) 0.67263(9) 0.6301(4) 0.0732(9) Uani d 1 . .
H H2 0.073519 0.662304 0.574143 0.088 Uiso calc 1 . .
C C3 0.2469(6) 0.71136(9) 0.6050(5) 0.0890(11) Uani d 1 . .
H H3 0.153321 0.726509 0.533416 0.107 Uiso calc 1 . .
C C4 0.4287(7) 0.72754(10) 0.6834(5) 0.0871(11) Uani d 1 . .
H H4 0.460834 0.753486 0.666273 0.105 Uiso calc 1 . .
C C5 0.5623(6) 0.70463(10) 0.7878(5) 0.0849(11) Uani d 1 . .
H H5 0.687062 0.715266 0.842693 0.102 Uiso calc 1 . .
C C6 0.5172(5) 0.66585(9) 0.8144(4) 0.0684(9) Uani d 1 . .
H H6 0.612551 0.650963 0.885571 0.082 Uiso calc 1 . .
C C7 0.4623(4) 0.58257(7) 0.7779(4) 0.0500(7) Uani d 1 . .
H H7A 0.579852 0.592960 0.854289 0.060 Uiso calc 1 . .
H H7B 0.513636 0.579710 0.660752 0.060 Uiso calc 1 . .
C C8 0.4003(4) 0.54349(7) 0.8453(4) 0.0554(8) Uani d 1 . .
H H8A 0.522296 0.525995 0.842923 0.067 Uiso calc 1 . .
H H8B 0.361408 0.545749 0.966498 0.067 Uiso calc 1 . .
C C9 0.0303(4) 0.55502(8) 0.7319(4) 0.0586(8) Uani d 1 . .
H H9A -0.018777 0.557418 0.849982 0.070 Uiso calc 1 . .
H H9B -0.088519 0.545041 0.655591 0.070 Uiso calc 1 . .
C C10 0.0951(4) 0.59416(8) 0.6670(4) 0.0544(7) Uani d 1 . .
H H10A 0.129289 0.592100 0.544591 0.065 Uiso calc 1 . .
H H10B -0.025699 0.611834 0.672570 0.065 Uiso calc 1 . .
O O1 0.0826(4) 0.45352(6) 0.8352(3) 0.0739(6) Uani d 1 . .
O O2 0.3636(4) 0.44271(8) 0.6833(4) 0.1271(11) Uani d 1 . .
C C11 0.1746(4) 0.38836(9) 0.7732(3) 0.0488(7) Uani d 1 . .
C C12 0.3158(5) 0.36281(11) 0.6979(4) 0.0710(9) Uani d 1 . .
H H12 0.434100 0.372529 0.643180 0.085 Uiso calc 1 . .
C C13 0.2834(6) 0.32351(12) 0.7030(4) 0.0850(11) Uani d 1 . .
H H13 0.378578 0.306980 0.650576 0.102 Uiso calc 1 . .
C C14 0.1131(7) 0.30867(10) 0.7841(5) 0.0841(10) Uani d 1 . .
H H14 0.092772 0.282041 0.788617 0.101 Uiso calc 1 . .
C C15 -0.0285(5) 0.33305(10) 0.8592(4) 0.0758(10) Uani d 1 . .
H H15 -0.145442 0.322946 0.914408 0.091 Uiso calc 1 . .
C C16 0.0017(4) 0.37282(8) 0.8532(4) 0.0566(8) Uani d 1 . .
H H16 -0.096028 0.389140 0.903761 0.068 Uiso calc 1 . .
C C17 0.2108(5) 0.43133(10) 0.7647(4) 0.0605(8) Uani d 1 . .
O O3 0.7231(3) 0.47794(7) 0.6283(3) 0.0737(7) Uani d 1 . .
H H31 0.816(5) 0.4679(11) 0.697(4) 0.111 Uiso d 1 . .
H H32 0.609(4) 0.4665(9) 0.645(5) 0.111 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
C1 N1 C10 . . 115.8(2) ?
C1 N1 C7 . . 116.32(19) ?
C10 N1 C7 . . 110.9(2) ?
C9 N2 C8 . . 109.8(2) ?
C9 N2 H21 . . 110.3(17) ?
C8 N2 H21 . . 110.0(17) ?
C9 N2 H22 . . 105.5(17) ?
C8 N2 H22 . . 112.5(17) ?
H21 N2 H22 . . 109(3) ?
C6 C1 C2 . . 116.7(3) ?
C6 C1 N1 . . 120.8(2) ?
C2 C1 N1 . . 122.5(3) ?
C1 C2 C3 . . 121.5(3) ?
C1 C2 H2 . . 119.3 ?
C3 C2 H2 . . 119.3 ?
C4 C3 C2 . . 121.2(3) ?
C4 C3 H3 . . 119.4 ?
C2 C3 H3 . . 119.4 ?
C3 C4 C5 . . 118.0(3) ?
C3 C4 H4 . . 121.0 ?
C5 C4 H4 . . 121.0 ?
C4 C5 C6 . . 121.7(3) ?
C4 C5 H5 . . 119.1 ?
C6 C5 H5 . . 119.1 ?
C1 C6 C5 . . 120.9(3) ?
C1 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
N1 C7 C8 . . 112.3(2) ?
N1 C7 H7A . . 109.1 ?
C8 C7 H7A . . 109.1 ?
N1 C7 H7B . . 109.1 ?
C8 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.9 ?
N2 C8 C7 . . 110.0(2) ?
N2 C8 H8A . . 109.7 ?
C7 C8 H8A . . 109.7 ?
N2 C8 H8B . . 109.7 ?
C7 C8 H8B . . 109.7 ?
H8A C8 H8B . . 108.2 ?
N2 C9 C10 . . 110.8(2) ?
N2 C9 H9A . . 109.5 ?
C10 C9 H9A . . 109.5 ?
N2 C9 H9B . . 109.5 ?
C10 C9 H9B . . 109.5 ?
H9A C9 H9B . . 108.1 ?
N1 C10 C9 . . 112.3(2) ?
N1 C10 H10A . . 109.2 ?
C9 C10 H10A . . 109.2 ?
N1 C10 H10B . . 109.2 ?
C9 C10 H10B . . 109.2 ?
H10A C10 H10B . . 107.9 ?
C16 C11 C12 . . 117.6(3) ?
C16 C11 C17 . . 121.8(3) ?
C12 C11 C17 . . 120.6(3) ?
C13 C12 C11 . . 121.2(3) ?
C13 C12 H12 . . 119.4 ?
C11 C12 H12 . . 119.4 ?
C14 C13 C12 . . 120.4(3) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C13 C14 C15 . . 119.7(3) ?
C13 C14 H14 . . 120.1 ?
C15 C14 H14 . . 120.1 ?
C14 C15 C16 . . 120.3(3) ?
C14 C15 H15 . . 119.9 ?
C16 C15 H15 . . 119.9 ?
C11 C16 C15 . . 120.8(3) ?
C11 C16 H16 . . 119.6 ?
C15 C16 H16 . . 119.6 ?
O2 C17 O1 . . 123.5(3) ?
O2 C17 C11 . . 117.4(3) ?
O1 C17 C11 . . 119.1(3) ?
H31 O3 H32 . . 106(4) ?
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 C1 . 1.417(3) ?
N1 C10 . 1.458(3) ?
N1 C7 . 1.465(3) ?
N2 C9 . 1.481(3) ?
N2 C8 . 1.488(3) ?
N2 H21 . 0.898(17) ?
N2 H22 . 0.893(16) ?
C1 C6 . 1.384(3) ?
C1 C2 . 1.384(3) ?
C2 C3 . 1.388(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.360(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.362(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.387(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.504(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.504(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
O1 C17 . 1.251(3) ?
O2 C17 . 1.230(3) ?
C11 C16 . 1.376(3) ?
C11 C12 . 1.393(4) ?
C11 C17 . 1.504(4) ?
C12 C13 . 1.375(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.358(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.369(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.389(4) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
O3 H31 . 0.830(18) ?
O3 H32 . 0.826(18) ?
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 O1 . 0.898(17) 1.921(18) 2.813(3) 173(2) yes
N2 H21 O2 . 0.898(17) 2.56(2) 3.112(4) 121(2) yes
N2 H22 O3 3_666 0.893(16) 1.923(17) 2.812(3) 173(2) yes
C9 H9A O1 3_567 0.97 2.48 3.420(4) 163.6 yes
C9 H9B O3 1_455 0.97 2.60 3.340(4) 133.2 yes
O3 H31 O1 1_655 0.830(18) 1.96(2) 2.772(3) 166(4) yes
O3 H32 O2 . 0.826(18) 1.773(18) 2.599(3) 179(4) 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
C10 N1 C1 C6 . . . . -173.8(2) ?
C7 N1 C1 C6 . . . . -40.8(3) ?
C10 N1 C1 C2 . . . . 8.5(3) ?
C7 N1 C1 C2 . . . . 141.5(3) ?
C6 C1 C2 C3 . . . . -0.8(4) ?
N1 C1 C2 C3 . . . . 177.0(3) ?
C1 C2 C3 C4 . . . . 0.4(5) ?
C2 C3 C4 C5 . . . . -0.1(5) ?
C3 C4 C5 C6 . . . . 0.2(5) ?
C2 C1 C6 C5 . . . . 0.8(4) ?
N1 C1 C6 C5 . . . . -177.0(3) ?
C4 C5 C6 C1 . . . . -0.6(5) ?
C1 N1 C7 C8 . . . . 170.0(2) ?
C10 N1 C7 C8 . . . . -54.7(3) ?
C9 N2 C8 C7 . . . . -57.2(3) ?
N1 C7 C8 N2 . . . . 56.6(3) ?
C8 N2 C9 C10 . . . . 57.0(3) ?
C1 N1 C10 C9 . . . . -170.5(2) ?
C7 N1 C10 C9 . . . . 54.1(3) ?
N2 C9 C10 N1 . . . . -56.0(3) ?
C16 C11 C12 C13 . . . . 0.1(4) ?
C17 C11 C12 C13 . . . . -179.3(3) ?
C11 C12 C13 C14 . . . . -0.8(5) ?
C12 C13 C14 C15 . . . . 0.9(5) ?
C13 C14 C15 C16 . . . . -0.2(5) ?
C12 C11 C16 C15 . . . . 0.5(4) ?
C17 C11 C16 C15 . . . . 179.9(3) ?
C14 C15 C16 C11 . . . . -0.5(5) ?
C16 C11 C17 O2 . . . . -176.6(3) ?
C12 C11 C17 O2 . . . . 2.8(4) ?
C16 C11 C17 O1 . . . . 1.4(4) ?
C12 C11 C17 O1 . . . . -179.2(3) ?
