#------------------------------------------------------------------------------
#$Date: 2023-06-06 08:34:37 +0300 (Tue, 06 Jun 2023) $
#$Revision: 284385 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/27/2022736.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_2022736
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 I O2 - , 0.5H2 O'
_chemical_formula_moiety         '2(C10 H14 N3 O2 +), 2(C7 H4 I O2 -), H2 O'
_chemical_formula_sum            'C34 H38 I2 N6 O9'
_chemical_formula_weight         928.50
_chemical_name_systematic
;
4-(4-Nitrophenyl)piperazin-1-ium 2-iodobenzoate 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                104.967(8)
_cell_angle_beta                 94.707(7)
_cell_angle_gamma                107.430(8)
_cell_formula_units_Z            1
_cell_length_a                   7.3949(6)
_cell_length_b                   9.3440(8)
_cell_length_c                   14.4980(10)
_cell_measurement_reflns_used    2991
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.95
_cell_volume                     909.44(14)
_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 0.995
_diffrn_measured_fraction_theta_max 0.887
_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  0.0236
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6275
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.015
_diffrn_reflns_theta_min         2.953
_exptl_absorpt_coefficient_mu    1.791
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysalisRed; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_description       prism
_exptl_crystal_F_000             462
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.440
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3904
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0464
_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)+(0.0514P)²+0.5457P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1169
_reflns_number_gt                2443
_reflns_number_total             3904
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb8051sup1.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 2022734--2022736.cif.'
_cod_original_cell_volume        909.44(13)
_cod_database_code               2022736
_cod_database_fobs_code          2022736
_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   0.468
_shelx_estimated_absorpt_t_max   0.673
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
C C1 0.1376(6) 0.6393(4) 0.1581(3) 0.0555(10) Uani d 1 . .
C C2 -0.0631(7) 0.5730(5) 0.1440(3) 0.0687(12) Uani d 1 . .
H H2 -0.116914 0.503974 0.178262 0.082 Uiso calc 1 . .
C C3 -0.1822(7) 0.6059(6) 0.0822(4) 0.0724(13) Uani d 1 . .
H H3 -0.314731 0.558330 0.073932 0.087 Uiso calc 1 . .
C C4 -0.1064(7) 0.7096(5) 0.0318(3) 0.0636(11) Uani d 1 . .
C C5 0.0897(7) 0.7763(6) 0.0429(3) 0.0723(13) Uani d 1 . .
H H5 0.141500 0.845343 0.008346 0.087 Uiso calc 1 . .
C C6 0.2093(7) 0.7419(5) 0.1044(3) 0.0667(12) Uani d 1 . .
H H6 0.341659 0.787923 0.110643 0.080 Uiso calc 1 . .
C C7 0.4418(7) 0.7234(7) 0.2667(5) 0.0957(18) Uani d 1 . .
H H7A 0.418923 0.802683 0.317971 0.115 Uiso calc 1 . .
H H7B 0.499045 0.773784 0.220487 0.115 Uiso calc 1 . .
C C8 0.5801(7) 0.6593(7) 0.3092(4) 0.0927(17) Uani d 1 . .
H H8A 0.619508 0.592894 0.257190 0.111 Uiso calc 1 . .
H H8B 0.693988 0.745578 0.346016 0.111 Uiso calc 1 . .
C C9 0.3145(8) 0.4451(6) 0.3207(4) 0.0897(16) Uani d 1 . .
H H9A 0.256781 0.389355 0.364560 0.108 Uiso calc 1 . .
H H9B 0.340842 0.370385 0.267916 0.108 Uiso calc 1 . .
C C10 0.1766(7) 0.5111(6) 0.2811(4) 0.0835(15) Uani d 1 . .
H H10A 0.061412 0.425824 0.244767 0.100 Uiso calc 1 . .
H H10B 0.139797 0.577245 0.334373 0.100 Uiso calc 1 . .
C C11 0.8424(6) 0.2081(5) 0.3805(3) 0.0609(11) Uani d 1 . .
C C12 0.8206(6) 0.1340(5) 0.2821(3) 0.0635(12) Uani d 1 . .
C C13 0.9344(9) 0.0414(6) 0.2499(4) 0.0850(16) Uani d 1 . .
H H13 0.920205 -0.009287 0.184112 0.102 Uiso calc 1 . .
C C14 1.0663(9) 0.0254(7) 0.3150(5) 0.0919(17) Uani d 1 . .
H H14 1.143373 -0.034148 0.292932 0.110 Uiso calc 1 . .
C C15 1.0857(8) 0.0952(7) 0.4112(5) 0.0857(15) Uani d 1 . .
H H15 1.174200 0.082483 0.455149 0.103 Uiso calc 1 . .
C C16 0.9743(7) 0.1845(6) 0.4432(4) 0.0769(13) Uani d 1 . .
H H16 0.987579 0.231020 0.509488 0.092 Uiso calc 1 . .
C C17 0.7295(7) 0.3142(7) 0.4194(3) 0.0746(13) Uani d 1 . .
I I1 0.61864(5) 0.15483(4) 0.18127(2) 0.08807(17) Uani d 1 . .
N N1 0.2589(5) 0.6027(4) 0.2184(3) 0.0622(9) Uani d 1 . .
N N2 0.4954(6) 0.5683(5) 0.3724(3) 0.0686(10) Uani d 1 . .
H H2A 0.482(7) 0.635(6) 0.424(4) 0.082 Uiso d 1 . .
H H2B 0.596(7) 0.539(6) 0.396(4) 0.082 Uiso d 1 . .
N N3 -0.2340(7) 0.7474(5) -0.0316(3) 0.0825(12) Uani d 1 . .
O O1 -0.4061(7) 0.6959(6) -0.0342(4) 0.1259(16) Uani d 1 . .
O O2 -0.1641(7) 0.8273(6) -0.0819(3) 0.1165(14) Uani d 1 . .
O O3 0.6139(6) 0.2673(6) 0.4715(3) 0.1206(15) Uani d 1 . .
O O4 0.7641(6) 0.4395(5) 0.4000(3) 0.0969(11) Uani d 1 . .
O O1WA 0.426(5) 0.976(3) 0.449(2) 0.154(7) Uani d 0.224(3) A -1
H H1W1 0.396(13) 1.048(8) 0.483(6) 0.231 Uiso d 0.224(3) A -1
H H1W2 0.470(14) 1.011(10) 0.406(4) 0.231 Uiso d 0.224(3) A -1
O O1WB 0.507(4) 0.935(3) 0.4569(19) 0.149(6) Uani d 0.276(3) B -2
H H1W3 0.427(8) 0.892(15) 0.486(6) 0.224 Uiso d 0.276(3) B -2
H H1W4 0.604(7) 0.916(12) 0.475(10) 0.224 Uiso d 0.276(3) B -2
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'
I I -0.4742 1.8119 '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
N1 C1 C6 . . 121.4(4) ?
N1 C1 C2 . . 122.6(4) ?
C6 C1 C2 . . 115.9(4) ?
C3 C2 C1 . . 122.4(4) ?
C3 C2 H2 . . 118.8 ?
C1 C2 H2 . . 118.8 ?
C2 C3 C4 . . 120.0(4) ?
C2 C3 H3 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C5 C4 C3 . . 119.5(5) ?
C5 C4 N3 . . 120.9(4) ?
C3 C4 N3 . . 119.6(4) ?
C6 C5 C4 . . 120.5(4) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C5 C6 C1 . . 121.7(4) ?
C5 C6 H6 . . 119.2 ?
C1 C6 H6 . . 119.2 ?
N1 C7 C8 . . 112.7(4) ?
N1 C7 H7A . . 109.1 ?
C8 C7 H7A . . 109.1 ?
N1 C7 H7B . . 109.1 ?
C8 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.8 ?
N2 C8 C7 . . 111.8(4) ?
N2 C8 H8A . . 109.3 ?
C7 C8 H8A . . 109.3 ?
N2 C8 H8B . . 109.3 ?
C7 C8 H8B . . 109.3 ?
H8A C8 H8B . . 107.9 ?
N2 C9 C10 . . 111.7(4) ?
N2 C9 H9A . . 109.3 ?
C10 C9 H9A . . 109.3 ?
N2 C9 H9B . . 109.3 ?
C10 C9 H9B . . 109.3 ?
H9A C9 H9B . . 107.9 ?
N1 C10 C9 . . 111.8(4) ?
N1 C10 H10A . . 109.3 ?
C9 C10 H10A . . 109.3 ?
N1 C10 H10B . . 109.3 ?
C9 C10 H10B . . 109.3 ?
H10A C10 H10B . . 107.9 ?
C16 C11 C12 . . 118.0(4) ?
C16 C11 C17 . . 120.1(4) ?
C12 C11 C17 . . 121.9(4) ?
C11 C12 C13 . . 119.3(5) ?
C11 C12 I1 . . 121.3(3) ?
C13 C12 I1 . . 119.4(4) ?
C14 C13 C12 . . 120.1(5) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C15 C14 C13 . . 120.8(5) ?
C15 C14 H14 . . 119.6 ?
C13 C14 H14 . . 119.6 ?
C14 C15 C16 . . 119.4(6) ?
C14 C15 H15 . . 120.3 ?
C16 C15 H15 . . 120.3 ?
C15 C16 C11 . . 122.3(5) ?
C15 C16 H16 . . 118.9 ?
C11 C16 H16 . . 118.9 ?
O4 C17 O3 . . 126.3(5) ?
O4 C17 C11 . . 118.0(5) ?
O3 C17 C11 . . 115.6(5) ?
C1 N1 C10 . . 118.7(4) ?
C1 N1 C7 . . 117.8(3) ?
C10 N1 C7 . . 111.5(4) ?
C8 N2 C9 . . 110.3(4) ?
C8 N2 H2A . . 107(3) ?
C9 N2 H2A . . 114(3) ?
C8 N2 H2B . . 104(3) ?
C9 N2 H2B . . 119(3) ?
H2A N2 H2B . . 102(5) ?
O1 N3 O2 . . 122.4(5) ?
O1 N3 C4 . . 119.3(5) ?
O2 N3 C4 . . 118.3(5) ?
H1W1 O1WA H1W2 . . 103(3) ?
H1W3 O1WB H1W4 . . 103(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 . 1.377(5) ?
C1 C6 . 1.398(6) ?
C1 C2 . 1.401(6) ?
C2 C3 . 1.359(7) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.376(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.373(6) ?
C4 N3 . 1.443(7) ?
C5 C6 . 1.367(7) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N1 . 1.454(6) ?
C7 C8 . 1.496(7) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 N2 . 1.461(6) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 N2 . 1.465(7) ?
C9 C10 . 1.487(7) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 N1 . 1.453(5) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C16 . 1.384(7) ?
C11 C12 . 1.387(6) ?
C11 C17 . 1.511(7) ?
C12 C13 . 1.403(7) ?
C12 I1 . 2.090(5) ?
C13 C14 . 1.369(8) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.354(8) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.365(7) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C17 O4 . 1.232(6) ?
C17 O3 . 1.243(6) ?
N2 H2A . 0.88(5) ?
N2 H2B . 0.93(5) ?
N3 O1 . 1.212(6) ?
N3 O2 . 1.212(6) ?
O1WA H1W1 . 0.82(2) ?
O1WA H1W2 . 0.82(2) ?
O1WB H1W3 . 0.83(2) ?
O1WB H1W4 . 0.82(2) ?
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
C2 H2 I1 1_455 0.93 3.28 4.110(4) 150.2 yes
C3 H3 O1 2_465 0.93 2.53 3.347(7) 146.9 yes
C6 H6 I1 1_565 0.93 3.26 3.940(4) 131.6 yes
C7 H7A O1WA . 0.97 2.14 3.09(3) 167.0 yes
C7 H7A O1WB . 0.97 2.01 2.85(3) 144.5 yes
N2 H2A O3 2_666 0.88(5) 1.86(5) 2.717(5) 164(5) yes
N2 H2B O4 . 0.93(5) 1.77(5) 2.666(6) 160(5) yes
O1WB H1W3 O3 2_666 0.83(2) 1.71(10) 2.37(2) 135(12) 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 . . . . -178.0(4) ?
C6 C1 C2 C3 . . . . -0.1(6) ?
C1 C2 C3 C4 . . . . -1.0(7) ?
C2 C3 C4 C5 . . . . 1.5(7) ?
C2 C3 C4 N3 . . . . -178.2(4) ?
C3 C4 C5 C6 . . . . -0.8(7) ?
N3 C4 C5 C6 . . . . 178.8(4) ?
C4 C5 C6 C1 . . . . -0.3(7) ?
N1 C1 C6 C5 . . . . 178.7(4) ?
C2 C1 C6 C5 . . . . 0.8(6) ?
N1 C7 C8 N2 . . . . -53.1(7) ?
N2 C9 C10 N1 . . . . 56.1(6) ?
C16 C11 C12 C13 . . . . -1.3(6) ?
C17 C11 C12 C13 . . . . 177.7(4) ?
C16 C11 C12 I1 . . . . 177.8(3) ?
C17 C11 C12 I1 . . . . -3.3(6) ?
C11 C12 C13 C14 . . . . -0.4(7) ?
I1 C12 C13 C14 . . . . -179.5(4) ?
C12 C13 C14 C15 . . . . 1.6(8) ?
C13 C14 C15 C16 . . . . -1.0(8) ?
C14 C15 C16 C11 . . . . -0.7(8) ?
C12 C11 C16 C15 . . . . 1.9(7) ?
C17 C11 C16 C15 . . . . -177.1(5) ?
C16 C11 C17 O4 . . . . 111.4(5) ?
C12 C11 C17 O4 . . . . -67.5(6) ?
C16 C11 C17 O3 . . . . -66.2(6) ?
C12 C11 C17 O3 . . . . 114.9(5) ?
C6 C1 N1 C10 . . . . 172.5(4) ?
C2 C1 N1 C10 . . . . -9.7(6) ?
C6 C1 N1 C7 . . . . 32.9(6) ?
C2 C1 N1 C7 . . . . -149.3(5) ?
C9 C10 N1 C1 . . . . 164.4(4) ?
C9 C10 N1 C7 . . . . -53.6(6) ?
C8 C7 N1 C1 . . . . -165.4(4) ?
C8 C7 N1 C10 . . . . 52.3(7) ?
C7 C8 N2 C9 . . . . 54.3(7) ?
C10 C9 N2 C8 . . . . -56.0(6) ?
C5 C4 N3 O1 . . . . -174.4(5) ?
C3 C4 N3 O1 . . . . 5.2(7) ?
C5 C4 N3 O2 . . . . 7.1(7) ?
C3 C4 N3 O2 . . . . -173.3(5) ?
