#------------------------------------------------------------------------------
#$Date: 2020-07-04 08:16:55 +0300 (Sat, 04 Jul 2020) $
#$Revision: 253759 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243469.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_2243469
loop_
_publ_author_name
'Harish Chinthal, Chayanna'
'Yathirajan, Hemmige S.'
'Kavitha, Channappa N.'
'Foro, Sabine'
'Glidewell, Christopher'
_publ_section_title
;
 The crystal structures of salts of N-(4-fluorophenyl)piperazine
 with four aromatic carboxylic acids and with picric acid
;
_journal_coeditor_code           HB7928
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1179
_journal_page_last               1186
_journal_paper_doi               10.1107/S2056989020008749
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C10 H14 F N2 +, C7 H4 Br O2 -, 0.353H2 O'
_chemical_formula_moiety         'C10 H14 F N2 +, C7 H4 Br O2 -, 0.353(H2 O)'
_chemical_formula_sum            'C17 H18.71 Br F N2 O2.35'
_chemical_formula_weight         387.59
_chemical_name_systematic
;
4-(4-Fluorophenyl)piperazin-1-ium 2-bromobenzoate 0.353-hydrate
;
_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     difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                101.140(10)
_cell_angle_beta                 95.980(10)
_cell_angle_gamma                109.440(10)
_cell_formula_units_Z            2
_cell_length_a                   7.2584(8)
_cell_length_b                   9.3470(10)
_cell_length_c                   13.767(2)
_cell_measurement_reflns_used    3585
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.617
_cell_measurement_theta_min      3.027
_cell_volume                     849.7(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
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL-2014 (Sheldrick, 2015b) and PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL-2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur with Sapphire CCD
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5475
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_min         3.027
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.442
_exptl_absorpt_correction_T_max  0.341
_exptl_absorpt_correction_T_min  0.257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_description       block
_exptl_crystal_F_000             395.1
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.480
_exptl_crystal_size_min          0.440
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.769
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0427
_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)+(0.0776P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1242
_reflns_number_gt                2775
_reflns_number_total             3582
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7928sup1.cif
_cod_data_source_block           II
_cod_original_cell_volume        849.72(19)
_cod_database_code               2243469
_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   0.375
_shelx_estimated_absorpt_t_max   0.413
_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 N1 0.4921(4) 0.5765(3) 0.36697(18) 0.0441(5) Uani d 1 . .
H H11 0.577(5) 0.549(4) 0.386(2) 0.053 Uiso d 1 . .
H H12 0.448(5) 0.616(4) 0.422(2) 0.053 Uiso d 1 . .
C C2 0.3355(5) 0.4415(3) 0.2958(2) 0.0553(7) Uani d 1 . .
H H2A 0.2812 0.3601 0.3304 0.066 Uiso calc 1 . .
H H2B 0.3928 0.3996 0.2417 0.066 Uiso calc 1 . .
C C3 0.1719(4) 0.4880(3) 0.2525(2) 0.0516(7) Uani d 1 . .
H H3A 0.0718 0.3979 0.2054 0.062 Uiso calc 1 . .
H H3B 0.1095 0.5246 0.3061 0.062 Uiso calc 1 . .
N N4 0.2506(3) 0.6110(2) 0.20113(16) 0.0398(5) Uani d 1 . .
C C5 0.4007(4) 0.7471(3) 0.2736(2) 0.0512(7) Uani d 1 . .
H H5A 0.3388 0.7855 0.3267 0.061 Uiso calc 1 . .
H H5B 0.4530 0.8300 0.2398 0.061 Uiso calc 1 . .
C C6 0.5673(4) 0.7068(4) 0.3186(2) 0.0520(7) Uani d 1 . .
H H6A 0.6373 0.6777 0.2665 0.062 Uiso calc 1 . .
H H6B 0.6605 0.7976 0.3682 0.062 Uiso calc 1 . .
C C21 0.1090(4) 0.6461(3) 0.1414(2) 0.0402(6) Uani d 1 . .
C C22 -0.0941(4) 0.5824(3) 0.1394(2) 0.0516(7) Uani d 1 . .
H H22 -0.1410 0.5151 0.1804 0.062 Uiso calc 1 . .
C C23 -0.2270(5) 0.6168(4) 0.0782(3) 0.0658(9) Uani d 1 . .
H H23 -0.3628 0.5720 0.0767 0.079 Uiso calc 1 . .
C C24 -0.1579(6) 0.7161(5) 0.0204(2) 0.0689(10) Uani d 1 . .
F F24 -0.2891(5) 0.7538(4) -0.0391(2) 0.1093(9) Uani d 1 . .
C C25 0.0363(7) 0.7830(5) 0.0199(3) 0.0724(10) Uani d 1 . .
H H25 0.0796 0.8530 -0.0200 0.087 Uiso calc 1 . .
C C26 0.1726(5) 0.7464(4) 0.0798(2) 0.0556(7) Uani d 1 . .
H H26 0.3074 0.7898 0.0784 0.067 Uiso calc 1 . .
C C31 0.8354(4) 0.2190(3) 0.3694(2) 0.0373(5) Uani d 1 . .
C C32 0.7930(4) 0.1403(3) 0.2693(2) 0.0402(6) Uani d 1 . .
Br Br32 0.59370(5) 0.15933(4) 0.17735(2) 0.06077(16) Uani d 1 . .
C C33 0.8889(5) 0.0410(3) 0.2323(3) 0.0552(8) Uani d 1 . .
H H33 0.8575 -0.0114 0.1646 0.066 Uiso calc 1 . .
C C34 1.0298(5) 0.0214(4) 0.2964(3) 0.0628(9) Uani d 1 . .
H H34 1.0970 -0.0431 0.2721 0.075 Uiso calc 1 . .
C C35 1.0731(5) 0.0959(4) 0.3964(3) 0.0622(9) Uani d 1 . .
H H35 1.1678 0.0808 0.4400 0.075 Uiso calc 1 . .
C C36 0.9752(4) 0.1941(4) 0.4325(2) 0.0529(7) Uani d 1 . .
H H36 1.0047 0.2439 0.5006 0.064 Uiso calc 1 . .
C C37 0.7364(4) 0.3310(3) 0.41091(19) 0.0417(6) Uani d 1 . .
O O31 0.6248(4) 0.2899(3) 0.4701(2) 0.0826(8) Uani d 1 . .
O O32 0.7754(3) 0.4539(2) 0.38357(18) 0.0584(6) Uani d 1 . .
O O41 0.4360(13) 0.0019(13) 0.4890(8) 0.101(4) Uiso d 0.353(8) . .
H H41 0.4989 0.0990 0.4825 0.152 Uiso d 0.353(8) . .
H H42 0.4159 -0.0920 0.5015 0.152 Uiso d 0.353(8) . .
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'
F F 0.0171 0.0103 '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
C6 N1 C2 . . 110.7(2) ?
C6 N1 H11 . . 111(2) ?
C2 N1 H11 . . 108(2) ?
C6 N1 H12 . . 106(2) ?
C2 N1 H12 . . 113(2) ?
H11 N1 H12 . . 108(3) ?
N1 C2 C3 . . 111.1(2) ?
N1 C2 H2A . . 109.4 ?
C3 C2 H2A . . 109.4 ?
N1 C2 H2B . . 109.4 ?
C3 C2 H2B . . 109.4 ?
H2A C2 H2B . . 108.0 ?
N4 C3 C2 . . 110.3(2) ?
N4 C3 H3A . . 109.6 ?
C2 C3 H3A . . 109.6 ?
N4 C3 H3B . . 109.6 ?
C2 C3 H3B . . 109.6 ?
H3A C3 H3B . . 108.1 ?
C21 N4 C3 . . 116.1(2) ?
C21 N4 C5 . . 114.7(2) ?
C3 N4 C5 . . 109.0(2) ?
N4 C5 C6 . . 111.5(2) ?
N4 C5 H5A . . 109.3 ?
C6 C5 H5A . . 109.3 ?
N4 C5 H5B . . 109.3 ?
C6 C5 H5B . . 109.3 ?
H5A C5 H5B . . 108.0 ?
N1 C6 C5 . . 110.8(2) ?
N1 C6 H6A . . 109.5 ?
C5 C6 H6A . . 109.5 ?
N1 C6 H6B . . 109.5 ?
C5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 108.1 ?
C26 C21 C22 . . 117.5(3) ?
C26 C21 N4 . . 119.2(3) ?
C22 C21 N4 . . 123.3(2) ?
C23 C22 C21 . . 121.3(3) ?
C23 C22 H22 . . 119.3 ?
C21 C22 H22 . . 119.3 ?
C24 C23 C22 . . 119.0(3) ?
C24 C23 H23 . . 120.5 ?
C22 C23 H23 . . 120.5 ?
C25 C24 C23 . . 122.5(3) ?
C25 C24 F24 . . 118.1(4) ?
C23 C24 F24 . . 119.4(4) ?
C24 C25 C26 . . 119.2(3) ?
C24 C25 H25 . . 120.4 ?
C26 C25 H25 . . 120.4 ?
C21 C26 C25 . . 120.5(3) ?
C21 C26 H26 . . 119.8 ?
C25 C26 H26 . . 119.8 ?
C36 C31 C32 . . 117.6(2) ?
C36 C31 C37 . . 119.7(2) ?
C32 C31 C37 . . 122.8(2) ?
C31 C32 C33 . . 121.8(3) ?
C31 C32 Br32 . . 120.83(19) ?
C33 C32 Br32 . . 117.3(2) ?
C34 C33 C32 . . 119.1(3) ?
C34 C33 H33 . . 120.4 ?
C32 C33 H33 . . 120.4 ?
C33 C34 C35 . . 120.4(3) ?
C33 C34 H34 . . 119.8 ?
C35 C34 H34 . . 119.8 ?
C34 C35 C36 . . 119.8(3) ?
C34 C35 H35 . . 120.1 ?
C36 C35 H35 . . 120.1 ?
C31 C36 C35 . . 121.2(3) ?
C31 C36 H36 . . 119.4 ?
C35 C36 H36 . . 119.4 ?
O32 C37 O31 . . 126.2(3) ?
O32 C37 C31 . . 117.6(2) ?
O31 C37 C31 . . 116.2(3) ?
O41 O41 H41 2_656 . 88.0 ?
O41 O41 H42 2_656 . 72.5 ?
H41 O41 H42 . . 160.5 ?
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 C6 . 1.473(4) ?
N1 C2 . 1.476(4) ?
N1 H11 . 0.78(3) ?
N1 H12 . 0.92(3) ?
C2 C3 . 1.500(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 N4 . 1.453(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
N4 C21 . 1.412(3) ?
N4 C5 . 1.470(4) ?
C5 C6 . 1.492(4) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C21 C26 . 1.382(4) ?
C21 C22 . 1.389(4) ?
C22 C23 . 1.373(4) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.344(5) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.340(6) ?
C24 F24 . 1.369(4) ?
C25 C26 . 1.393(5) ?
C25 H25 . 0.9300 ?
C26 H26 . 0.9300 ?
C31 C36 . 1.376(4) ?
C31 C32 . 1.379(4) ?
C31 C37 . 1.514(3) ?
C32 C33 . 1.388(4) ?
C32 Br32 . 1.898(3) ?
C33 C34 . 1.363(5) ?
C33 H33 . 0.9300 ?
C34 C35 . 1.368(5) ?
C34 H34 . 0.9300 ?
C35 C36 . 1.387(4) ?
C35 H35 . 0.9300 ?
C36 H36 . 0.9300 ?
C37 O32 . 1.231(3) ?
C37 O31 . 1.233(3) ?
O41 O41 2_656 0.962(16) ?
O41 H41 . 0.8970 ?
O41 H42 . 0.8940 ?
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
N1 H11 O32 . 0.78(4) 1.93(4) 2.677(4) 160(3) no
N1 H12 O31 2_666 0.91(3) 1.80(3) 2.707(4) 175(3) no
O41 H41 O31 . 0.90 1.76 2.661(12) 179 no
O41 H42 O31 2_656 0.89 1.90 2.792(12) 179 no
C35 H35 O41 1_655 0.93 2.38 3.257(11) 157 no
C2 H2A Cg1 1_455 0.97 2.78 3.598(3) 142 no
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
C6 N1 C2 C3 . . . . -54.9(3) ?
N1 C2 C3 N4 . . . . 58.5(3) ?
C2 C3 N4 C21 . . . . 168.8(2) ?
C2 C3 N4 C5 . . . . -59.8(3) ?
C21 N4 C5 C6 . . . . -168.4(2) ?
C3 N4 C5 C6 . . . . 59.5(3) ?
C2 N1 C6 C5 . . . . 53.7(3) ?
N4 C5 C6 N1 . . . . -56.6(3) ?
C3 N4 C21 C26 . . . . -171.3(3) ?
C5 N4 C21 C26 . . . . 60.0(3) ?
C3 N4 C21 C22 . . . . 7.4(4) ?
C5 N4 C21 C22 . . . . -121.2(3) ?
C26 C21 C22 C23 . . . . 0.4(4) ?
N4 C21 C22 C23 . . . . -178.3(3) ?
C21 C22 C23 C24 . . . . -1.1(5) ?
C22 C23 C24 C25 . . . . 0.2(5) ?
C22 C23 C24 F24 . . . . -178.5(3) ?
C23 C24 C25 C26 . . . . 1.3(6) ?
F24 C24 C25 C26 . . . . -180.0(3) ?
C22 C21 C26 C25 . . . . 1.1(4) ?
N4 C21 C26 C25 . . . . 179.9(3) ?
C24 C25 C26 C21 . . . . -2.0(5) ?
C36 C31 C32 C33 . . . . -1.0(4) ?
C37 C31 C32 C33 . . . . 178.4(2) ?
C36 C31 C32 Br32 . . . . 177.1(2) ?
C37 C31 C32 Br32 . . . . -3.5(3) ?
C31 C32 C33 C34 . . . . -0.4(4) ?
Br32 C32 C33 C34 . . . . -178.5(2) ?
C32 C33 C34 C35 . . . . 1.4(5) ?
C33 C34 C35 C36 . . . . -1.0(5) ?
C32 C31 C36 C35 . . . . 1.3(4) ?
C37 C31 C36 C35 . . . . -178.1(3) ?
C34 C35 C36 C31 . . . . -0.4(5) ?
C36 C31 C37 O32 . . . . 111.7(3) ?
C32 C31 C37 O32 . . . . -67.7(3) ?
C36 C31 C37 O31 . . . . -67.7(4) ?
C32 C31 C37 O31 . . . . 112.9(3) ?

_cod_database_fobs_code 2243469
