#------------------------------------------------------------------------------
#$Date: 2023-06-06 08:34:37 +0300 (Tue, 06 Jun 2023) $
#$Revision: 284385 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/27/2022735.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_2022735
loop_
_publ_author_name
'Prasad, Holehundi J Shankara'
'Devaraju, ?'
'Yathirajan, Hemmige S.'
'Akkurt, Mehmet'
'Foro, Sabine'
'Balerao, Rishik'
'Butcher, Ray J.'
_publ_section_title
;
 Syntheses and crystal structures of three salts of
 1-(4-nitro-phenyl)-piperazine.
;
_journal_issue                   'Pt 5'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              423
_journal_page_last               427
_journal_paper_doi               10.1107/S205698902300302X
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C10 H14 N3 O2 +, C7 H4 Br O2 - , 0.5H2 O'
_chemical_formula_moiety         'C10 H14 N3 O2 +, C7 H4 Br O2 -, 0.5(H2 O)'
_chemical_formula_sum            'C17 H19 Br N3 O4.5'
_chemical_formula_weight         417.26
_chemical_name_systematic
;
4-(4-Nitrophenyl)piperazin-1-ium 2-bromobenzoate hemihydrate
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                102.101(6)
_cell_angle_beta                 99.534(6)
_cell_angle_gamma                110.981(6)
_cell_formula_units_Z            2
_cell_length_a                   7.2570(5)
_cell_length_b                   9.7772(6)
_cell_length_c                   14.2020(10)
_cell_measurement_reflns_used    2832
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.92
_cell_measurement_theta_min      3.03
_cell_volume                     887.41(12)
_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
;
Olex2 1.5 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 1.5 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015a)
;
_computing_structure_solution
;
SHELXL2018 (Sheldrick, 2015b)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6177
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.980
_diffrn_reflns_theta_min         3.039
_exptl_absorpt_coefficient_mu    2.347
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysalisRed; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_description       prism
_exptl_crystal_F_000             426
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.326
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3856
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.234
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0360
_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)+(0.0444P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0843
_reflns_number_gt                2478
_reflns_number_total             3856
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb8051sup1.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 2022734--2022736.cif.'
_cod_original_cell_volume        887.41(11)
_cod_original_formula_sum        'C17 H19 Br N3 O4.50'
_cod_database_code               2022735
_cod_database_fobs_code          2022735
_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   0.485
_shelx_estimated_absorpt_t_max   0.651
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
O O1 0.4472(3) 0.9088(2) 0.57716(16) 0.0866(7) Uani d 1 . .
O O2 0.1466(4) 0.7360(3) 0.53813(19) 0.0965(8) Uani d 1 . .
N N1 0.5490(3) 0.3809(2) 0.27923(14) 0.0452(5) Uani d 1 . .
N N2 0.6259(3) 0.1873(2) 0.12301(15) 0.0462(5) Uani d 1 . .
H H2A 0.686(3) 0.132(3) 0.1015(18) 0.055 Uiso d 1 . .
H H2B 0.556(3) 0.198(3) 0.0700(14) 0.055 Uiso d 1 . .
N N3 0.3218(4) 0.7818(3) 0.53126(16) 0.0593(6) Uani d 1 . .
C C1 0.3797(4) 0.6788(3) 0.46525(17) 0.0447(6) Uani d 1 . .
C C2 0.2487(4) 0.5276(3) 0.4245(2) 0.0540(7) Uani d 1 . .
H H2 0.123215 0.491207 0.439437 0.065 Uiso calc 1 . .
C C3 0.3015(4) 0.4304(3) 0.36200(19) 0.0518(6) Uani d 1 . .
H H3 0.209824 0.328530 0.333702 0.062 Uiso calc 1 . .
C C4 0.4910(3) 0.4806(2) 0.33958(16) 0.0399(5) Uani d 1 . .
C C5 0.6204(4) 0.6357(3) 0.38273(19) 0.0493(6) Uani d 1 . .
H H5 0.746350 0.673689 0.368381 0.059 Uiso calc 1 . .
C C6 0.5675(4) 0.7326(3) 0.44508(18) 0.0505(6) Uani d 1 . .
H H6 0.657730 0.834750 0.473932 0.061 Uiso calc 1 . .
C C7 0.3935(4) 0.2306(3) 0.2201(2) 0.0611(8) Uani d 1 . .
H H7A 0.307731 0.241586 0.164666 0.073 Uiso calc 1 . .
H H7B 0.307496 0.187484 0.261102 0.073 Uiso calc 1 . .
C C8 0.4847(5) 0.1232(3) 0.1806(2) 0.0676(8) Uani d 1 . .
H H8A 0.557431 0.102503 0.235884 0.081 Uiso calc 1 . .
H H8B 0.376210 0.026977 0.138441 0.081 Uiso calc 1 . .
C C9 0.7856(4) 0.3349(3) 0.1852(2) 0.0781(10) Uani d 1 . .
H H9A 0.874756 0.378980 0.145729 0.094 Uiso calc 1 . .
H H9B 0.867453 0.319121 0.239824 0.094 Uiso calc 1 . .
C C10 0.6991(5) 0.4438(3) 0.2265(3) 0.0808(10) Uani d 1 . .
H H10A 0.809491 0.536313 0.271886 0.097 Uiso calc 1 . .
H H10B 0.635383 0.471694 0.172320 0.097 Uiso calc 1 . .
Br Br1 0.92610(5) -0.00832(3) 0.31967(2) 0.06679(14) Uani d 1 . .
O O3 0.8488(3) 0.0263(3) 0.09269(16) 0.0782(6) Uani d 1 . .
O O4 0.6156(3) -0.2125(3) 0.03302(17) 0.0860(7) Uani d 1 . .
C C11 0.9379(3) -0.1685(3) 0.12893(18) 0.0438(6) Uani d 1 . .
C C12 1.0135(4) -0.1304(3) 0.23087(19) 0.0469(6) Uani d 1 . .
C C13 1.1536(4) -0.1827(3) 0.2715(2) 0.0609(7) Uani d 1 . .
H H13 1.201561 -0.157757 0.340436 0.073 Uiso calc 1 . .
C C14 1.2204(4) -0.2701(3) 0.2107(3) 0.0671(8) Uani d 1 . .
H H14 1.316352 -0.303199 0.238116 0.080 Uiso calc 1 . .
C C15 1.1471(4) -0.3102(3) 0.1086(2) 0.0630(8) Uani d 1 . .
H H15 1.193664 -0.369875 0.067067 0.076 Uiso calc 1 . .
C C16 1.0048(4) -0.2615(3) 0.0683(2) 0.0545(7) Uani d 1 . .
H H16 0.952495 -0.291267 -0.000611 0.065 Uiso calc 1 . .
C C17 0.7895(5) -0.1121(4) 0.0817(2) 0.0564(7) Uani d 1 . .
O O1W 0.5508(9) -0.5202(7) -0.0662(6) 0.138(2) Uani d 0.5 A -1
H H1W1 0.435882 -0.430124 -0.060307 0.207 Uiso d 0.5 A -1
H H1W2 0.458306 -0.629327 -0.042348 0.207 Uiso d 0.5 A -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'
Br Br -0.2901 2.4595 '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
C4 N1 C10 . . 118.22(18) ?
C4 N1 C7 . . 118.65(17) ?
C10 N1 C7 . . 112.0(2) ?
C9 N2 C8 . . 109.6(2) ?
C9 N2 H2A . . 106.7(16) ?
C8 N2 H2A . . 114.7(17) ?
C9 N2 H2B . . 110.9(17) ?
C8 N2 H2B . . 108.5(16) ?
H2A N2 H2B . . 106(2) ?
O1 N3 O2 . . 122.2(2) ?
O1 N3 C1 . . 119.5(2) ?
O2 N3 C1 . . 118.3(2) ?
C2 C1 C6 . . 120.1(2) ?
C2 C1 N3 . . 119.9(2) ?
C6 C1 N3 . . 120.0(2) ?
C3 C2 C1 . . 120.2(2) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
C2 C3 C4 . . 121.4(2) ?
C2 C3 H3 . . 119.3 ?
C4 C3 H3 . . 119.3 ?
N1 C4 C5 . . 121.73(19) ?
N1 C4 C3 . . 121.6(2) ?
C5 C4 C3 . . 116.6(2) ?
C6 C5 C4 . . 121.9(2) ?
C6 C5 H5 . . 119.0 ?
C4 C5 H5 . . 119.0 ?
C5 C6 C1 . . 119.7(2) ?
C5 C6 H6 . . 120.2 ?
C1 C6 H6 . . 120.2 ?
N1 C7 C8 . . 112.2(2) ?
N1 C7 H7A . . 109.2 ?
C8 C7 H7A . . 109.2 ?
N1 C7 H7B . . 109.2 ?
C8 C7 H7B . . 109.2 ?
H7A C7 H7B . . 107.9 ?
N2 C8 C7 . . 111.3(2) ?
N2 C8 H8A . . 109.4 ?
C7 C8 H8A . . 109.4 ?
N2 C8 H8B . . 109.4 ?
C7 C8 H8B . . 109.4 ?
H8A C8 H8B . . 108.0 ?
N2 C9 C10 . . 112.0(2) ?
N2 C9 H9A . . 109.2 ?
C10 C9 H9A . . 109.2 ?
N2 C9 H9B . . 109.2 ?
C10 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
N1 C10 C9 . . 112.8(2) ?
N1 C10 H10A . . 109.0 ?
C9 C10 H10A . . 109.0 ?
N1 C10 H10B . . 109.0 ?
C9 C10 H10B . . 109.0 ?
H10A C10 H10B . . 107.8 ?
C12 C11 C16 . . 118.0(2) ?
C12 C11 C17 . . 122.6(2) ?
C16 C11 C17 . . 119.3(2) ?
C11 C12 C13 . . 120.8(2) ?
C11 C12 Br1 . . 121.09(19) ?
C13 C12 Br1 . . 118.1(2) ?
C14 C13 C12 . . 120.0(3) ?
C14 C13 H13 . . 120.0 ?
C12 C13 H13 . . 120.0 ?
C13 C14 C15 . . 120.4(3) ?
C13 C14 H14 . . 119.8 ?
C15 C14 H14 . . 119.8 ?
C16 C15 C14 . . 119.7(3) ?
C16 C15 H15 . . 120.2 ?
C14 C15 H15 . . 120.2 ?
C15 C16 C11 . . 121.0(3) ?
C15 C16 H16 . . 119.5 ?
C11 C16 H16 . . 119.5 ?
O3 C17 O4 . . 126.0(3) ?
O3 C17 C11 . . 117.9(3) ?
O4 C17 C11 . . 116.2(3) ?
H1W1 O1W H1W2 . . 105.4 ?
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
O1 N3 . 1.204(3) ?
O2 N3 . 1.216(3) ?
N1 C4 . 1.387(3) ?
N1 C10 . 1.452(3) ?
N1 C7 . 1.456(3) ?
N2 C9 . 1.461(3) ?
N2 C8 . 1.465(3) ?
N2 H2A . 0.846(16) ?
N2 H2B . 0.881(16) ?
N3 C1 . 1.452(3) ?
C1 C2 . 1.370(3) ?
C1 C6 . 1.376(3) ?
C2 C3 . 1.363(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.400(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.399(3) ?
C5 C6 . 1.361(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.492(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.487(4) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
Br1 C12 . 1.896(2) ?
O3 C17 . 1.230(3) ?
O4 C17 . 1.254(3) ?
C11 C12 . 1.378(3) ?
C11 C16 . 1.389(3) ?
C11 C17 . 1.502(4) ?
C12 C13 . 1.389(4) ?
C13 C14 . 1.355(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.377(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.375(4) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
O1W H1W1 . 1.4134 ?
O1W H1W2 . 1.1905 ?
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 H2A O3 . 0.846(16) 1.832(18) 2.655(3) 164(2) yes
N2 H2B O4 2_655 0.881(16) 1.824(17) 2.701(3) 173(2) yes
C2 H2 O2 2_566 0.93 2.50 3.307(4) 145.1 yes
C7 H7B Br1 1_455 0.97 3.11 4.032(2) 160.1 yes
C10 H10B O1W 2_655 0.97 2.10 3.057(8) 169.1 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
O1 N3 C1 C2 . . . . 170.2(3) ?
O2 N3 C1 C2 . . . . -9.8(4) ?
O1 N3 C1 C6 . . . . -8.7(4) ?
O2 N3 C1 C6 . . . . 171.2(3) ?
C6 C1 C2 C3 . . . . -1.4(4) ?
N3 C1 C2 C3 . . . . 179.7(2) ?
C1 C2 C3 C4 . . . . 1.4(4) ?
C10 N1 C4 C5 . . . . -26.0(3) ?
C7 N1 C4 C5 . . . . -167.1(2) ?
C10 N1 C4 C3 . . . . 155.3(3) ?
C7 N1 C4 C3 . . . . 14.2(3) ?
C2 C3 C4 N1 . . . . 177.4(2) ?
C2 C3 C4 C5 . . . . -1.3(4) ?
N1 C4 C5 C6 . . . . -177.4(2) ?
C3 C4 C5 C6 . . . . 1.4(4) ?
C4 C5 C6 C1 . . . . -1.4(4) ?
C2 C1 C6 C5 . . . . 1.4(4) ?
N3 C1 C6 C5 . . . . -179.6(2) ?
C4 N1 C7 C8 . . . . -165.1(2) ?
C10 N1 C7 C8 . . . . 51.5(3) ?
C9 N2 C8 C7 . . . . 57.1(3) ?
N1 C7 C8 N2 . . . . -55.5(3) ?
C8 N2 C9 C10 . . . . -56.2(3) ?
C4 N1 C10 C9 . . . . 165.9(2) ?
C7 N1 C10 C9 . . . . -50.6(4) ?
N2 C9 C10 N1 . . . . 53.6(4) ?
C16 C11 C12 C13 . . . . 0.5(4) ?
C17 C11 C12 C13 . . . . -178.8(2) ?
C16 C11 C12 Br1 . . . . -178.41(17) ?
C17 C11 C12 Br1 . . . . 2.4(3) ?
C11 C12 C13 C14 . . . . 1.2(4) ?
Br1 C12 C13 C14 . . . . -179.9(2) ?
C12 C13 C14 C15 . . . . -1.3(4) ?
C13 C14 C15 C16 . . . . -0.2(4) ?
C14 C15 C16 C11 . . . . 1.9(4) ?
C12 C11 C16 C15 . . . . -2.0(4) ?
C17 C11 C16 C15 . . . . 177.2(3) ?
C12 C11 C17 O3 . . . . 65.2(3) ?
C16 C11 C17 O3 . . . . -114.1(3) ?
C12 C11 C17 O4 . . . . -115.8(3) ?
C16 C11 C17 O4 . . . . 64.9(3) ?
