#------------------------------------------------------------------------------
#$Date: 2020-10-31 07:27:38 +0200 (Sat, 31 Oct 2020) $
#$Revision: 258663 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/36/2243644.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_2243644
loop_
_publ_author_name
'Harish Chinthal, Chayanna'
'Kavitha, Channappa N.'
'Yathirajan, Hemmige S.'
'Foro, Sabine'
'Rathore, Ravindranath S.'
'Glidewell, Christopher'
_publ_section_title
;
 Fifteen 4-(2-methoxyphenyl)piperazin-1-ium salts containing organic
 anions: supramolecular assembly in zero, one, two and three dimensions
;
_journal_coeditor_code           HB7950
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1779
_journal_page_last               1793
_journal_paper_doi               10.1107/S2056989020014097
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C11 H17 N2 O +, C7 H4 Cl O2 -'
_chemical_formula_moiety         'C11 H17 N2 O +, C7 H4 Cl O2 -'
_chemical_formula_sum            'C18 H21 Cl N2 O3'
_chemical_formula_weight         348.82
_chemical_name_systematic
;
4-(2-Methoxyphenyl)piperazin-1-ium 4-chlorobenzoate
;
_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                100.28(2)
_cell_angle_beta                 94.400(10)
_cell_angle_gamma                94.140(10)
_cell_formula_units_Z            2
_cell_length_a                   7.4010(10)
_cell_length_b                   7.8880(10)
_cell_length_c                   15.410(3)
_cell_measurement_reflns_used    3770
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.769
_cell_measurement_theta_min      2.634
_cell_volume                     879.2(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      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.928
_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  0.0191
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6241
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.517
_diffrn_reflns_theta_min         2.634
_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    0.235
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.270
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0529
_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)+(0.0498P)²+0.3034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1305
_reflns_number_gt                2318
_reflns_number_total             3763
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7950sup1.cif
_cod_data_source_block           I
_cod_database_code               2243644
_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   0.904
_shelx_estimated_absorpt_t_max   0.963
_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 0.3863(3) 0.5719(3) 0.61980(13) 0.0537(6) Uani d 1 . .
H H11 0.349(3) 0.654(3) 0.5787(16) 0.064 Uiso d 1 . .
H H12 0.494(4) 0.526(3) 0.6072(17) 0.064 Uiso d 1 . .
C C2 0.2453(4) 0.4243(3) 0.61032(16) 0.0595(7) Uani d 1 . .
H H2A 0.2389 0.3567 0.5509 0.071 Uiso calc 1 . .
H H2B 0.1276 0.4677 0.6194 0.071 Uiso calc 1 . .
C C3 0.2901(4) 0.3104(3) 0.67711(14) 0.0492(6) Uani d 1 . .
H H3A 0.1964 0.2154 0.6709 0.059 Uiso calc 1 . .
H H3B 0.4051 0.2623 0.6665 0.059 Uiso calc 1 . .
N N4 0.3016(3) 0.4131(2) 0.76645(11) 0.0417(5) Uani d 1 . .
C C5 0.4446(3) 0.5568(3) 0.77727(15) 0.0456(6) Uani d 1 . .
H H5A 0.5614 0.5111 0.7685 0.055 Uiso calc 1 . .
H H5B 0.4511 0.6234 0.8369 0.055 Uiso calc 1 . .
C C6 0.4046(4) 0.6728(3) 0.71121(15) 0.0489(6) Uani d 1 . .
H H6A 0.2928 0.7261 0.7232 0.059 Uiso calc 1 . .
H H6B 0.5023 0.7641 0.7173 0.059 Uiso calc 1 . .
C C21 0.3080(3) 0.3202(3) 0.83759(14) 0.0402(5) Uani d 1 . .
C C22 0.2709(3) 0.4034(3) 0.92205(14) 0.0401(5) Uani d 1 . .
C C23 0.2740(3) 0.3164(3) 0.99224(16) 0.0500(6) Uani d 1 . .
H H23 0.2531 0.3740 1.0482 0.060 Uiso calc 1 . .
C C24 0.3080(4) 0.1439(3) 0.97981(17) 0.0565(7) Uani d 1 . .
H H24 0.3088 0.0854 1.0272 0.068 Uiso calc 1 . .
C C25 0.3405(4) 0.0595(3) 0.89756(18) 0.0588(7) Uani d 1 . .
H H25 0.3615 -0.0569 0.8889 0.071 Uiso calc 1 . .
C C26 0.3420(3) 0.1471(3) 0.82735(16) 0.0498(6) Uani d 1 . .
H H26 0.3663 0.0889 0.7721 0.060 Uiso calc 1 . .
O O22 0.2258(2) 0.5712(2) 0.92836(10) 0.0522(4) Uani d 1 . .
C C27 0.2117(4) 0.6682(3) 1.01422(15) 0.0539(6) Uani d 1 . .
H H27A 0.1780 0.7816 1.0093 0.081 Uiso calc 1 . .
H H27B 0.3267 0.6779 1.0488 0.081 Uiso calc 1 . .
H H27C 0.1207 0.6107 1.0426 0.081 Uiso calc 1 . .
C C31 0.2111(3) 0.8543(3) 0.37936(15) 0.0450(6) Uani d 1 . .
C C32 0.1780(4) 0.8004(3) 0.28892(17) 0.0597(7) Uani d 1 . .
H H32 0.1867 0.6850 0.2643 0.072 Uiso calc 1 . .
C C33 0.1321(4) 0.9151(4) 0.23404(17) 0.0622(7) Uani d 1 . .
H H33 0.1104 0.8772 0.1732 0.075 Uiso calc 1 . .
C C34 0.1190(3) 1.0848(3) 0.27049(16) 0.0498(6) Uani d 1 . .
Cl Cl34 0.06196(11) 1.23102(10) 0.20197(5) 0.0724(3) Uani d 1 . .
C C35 0.1471(5) 1.1410(3) 0.35980(18) 0.0712(9) Uani d 1 . .
H H35 0.1353 1.2559 0.3843 0.085 Uiso calc 1 . .
C C36 0.1932(5) 1.0247(3) 0.41347(17) 0.0697(9) Uani d 1 . .
H H36 0.2127 1.0631 0.4744 0.084 Uiso calc 1 . .
C C37 0.2650(4) 0.7306(3) 0.43954(18) 0.0529(6) Uani d 1 . .
O O31 0.2833(4) 0.7908(3) 0.52081(13) 0.0955(8) Uani d 1 . .
O O32 0.2879(3) 0.5797(2) 0.40612(13) 0.0704(6) Uani 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'
Cl Cl 0.1484 0.1585 '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 . . 110.65(19) ?
C6 N1 H11 . . 107.0(14) ?
C2 N1 H11 . . 109.8(15) ?
C6 N1 H12 . . 109.8(17) ?
C2 N1 H12 . . 106.9(16) ?
H11 N1 H12 . . 113(2) ?
N1 C2 C3 . . 110.5(2) ?
N1 C2 H2A . . 109.6 ?
C3 C2 H2A . . 109.6 ?
N1 C2 H2B . . 109.6 ?
C3 C2 H2B . . 109.6 ?
H2A C2 H2B . . 108.1 ?
N4 C3 C2 . . 109.35(19) ?
N4 C3 H3A . . 109.8 ?
C2 C3 H3A . . 109.8 ?
N4 C3 H3B . . 109.8 ?
C2 C3 H3B . . 109.8 ?
H3A C3 H3B . . 108.3 ?
C21 N4 C3 . . 116.59(17) ?
C21 N4 C5 . . 113.53(18) ?
C3 N4 C5 . . 110.53(18) ?
N4 C5 C6 . . 110.35(19) ?
N4 C5 H5A . . 109.6 ?
C6 C5 H5A . . 109.6 ?
N4 C5 H5B . . 109.6 ?
C6 C5 H5B . . 109.6 ?
H5A C5 H5B . . 108.1 ?
N1 C6 C5 . . 110.38(19) ?
N1 C6 H6A . . 109.6 ?
C5 C6 H6A . . 109.6 ?
N1 C6 H6B . . 109.6 ?
C5 C6 H6B . . 109.6 ?
H6A C6 H6B . . 108.1 ?
C26 C21 C22 . . 117.5(2) ?
C26 C21 N4 . . 123.2(2) ?
C22 C21 N4 . . 119.20(19) ?
O22 C22 C23 . . 123.4(2) ?
O22 C22 C21 . . 115.91(18) ?
C23 C22 C21 . . 120.7(2) ?
C22 C23 C24 . . 120.4(2) ?
C22 C23 H23 . . 119.8 ?
C24 C23 H23 . . 119.8 ?
C25 C24 C23 . . 119.8(2) ?
C25 C24 H24 . . 120.1 ?
C23 C24 H24 . . 120.1 ?
C24 C25 C26 . . 120.1(2) ?
C24 C25 H25 . . 120.0 ?
C26 C25 H25 . . 120.0 ?
C25 C26 C21 . . 121.5(2) ?
C25 C26 H26 . . 119.3 ?
C21 C26 H26 . . 119.3 ?
C22 O22 C27 . . 117.86(17) ?
O22 C27 H27A . . 109.5 ?
O22 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
O22 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C36 C31 C32 . . 117.8(2) ?
C36 C31 C37 . . 120.7(2) ?
C32 C31 C37 . . 121.5(2) ?
C31 C32 C33 . . 121.2(2) ?
C31 C32 H32 . . 119.4 ?
C33 C32 H32 . . 119.4 ?
C34 C33 C32 . . 119.2(2) ?
C34 C33 H33 . . 120.4 ?
C32 C33 H33 . . 120.4 ?
C35 C34 C33 . . 120.9(2) ?
C35 C34 Cl34 . . 119.4(2) ?
C33 C34 Cl34 . . 119.7(2) ?
C34 C35 C36 . . 119.0(2) ?
C34 C35 H35 . . 120.5 ?
C36 C35 H35 . . 120.5 ?
C31 C36 C35 . . 121.9(2) ?
C31 C36 H36 . . 119.1 ?
C35 C36 H36 . . 119.1 ?
O32 C37 O31 . . 124.7(2) ?
O32 C37 C31 . . 119.0(2) ?
O31 C37 C31 . . 116.3(2) ?
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 . 1.481(3) ?
N1 C2 . 1.485(3) ?
N1 H11 . 1.02(3) ?
N1 H12 . 0.92(3) ?
C2 C3 . 1.516(3) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 N4 . 1.461(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
N4 C21 . 1.423(3) ?
N4 C5 . 1.471(3) ?
C5 C6 . 1.512(3) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C21 C26 . 1.389(3) ?
C21 C22 . 1.406(3) ?
C22 O22 . 1.377(2) ?
C22 C23 . 1.380(3) ?
C23 C24 . 1.384(3) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.370(4) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.385(3) ?
C25 H25 . 0.9300 ?
C26 H26 . 0.9300 ?
O22 C27 . 1.421(3) ?
C27 H27A . 0.9600 ?
C27 H27B . 0.9600 ?
C27 H27C . 0.9600 ?
C31 C36 . 1.373(3) ?
C31 C32 . 1.380(3) ?
C31 C37 . 1.515(3) ?
C32 C33 . 1.386(3) ?
C32 H32 . 0.9300 ?
C33 C34 . 1.369(4) ?
C33 H33 . 0.9300 ?
C34 C35 . 1.364(3) ?
C34 Cl34 . 1.750(2) ?
C35 C36 . 1.384(3) ?
C35 H35 . 0.9300 ?
C36 H36 . 0.9300 ?
C37 O32 . 1.239(3) ?
C37 O31 . 1.251(3) ?
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 O31 . 1.02(2) 1.60(2) 2.616(3) 176(2) no
N1 H12 O32 2_666 0.92(3) 1.88(3) 2.792(3) 173(2) no
C3 H3A Cg1 2_666 0.97 2.96 3.881(3) 160 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 . . . . -56.8(3) ?
N1 C2 C3 N4 . . . . 58.6(3) ?
C2 C3 N4 C21 . . . . 168.3(2) ?
C2 C3 N4 C5 . . . . -60.1(3) ?
C21 N4 C5 C6 . . . . -167.25(18) ?
C3 N4 C5 C6 . . . . 59.6(2) ?
C2 N1 C6 C5 . . . . 55.6(3) ?
N4 C5 C6 N1 . . . . -56.8(3) ?
C3 N4 C21 C26 . . . . 13.9(3) ?
C5 N4 C21 C26 . . . . -116.3(2) ?
C3 N4 C21 C22 . . . . -163.3(2) ?
C5 N4 C21 C22 . . . . 66.5(3) ?
C26 C21 C22 O22 . . . . -175.8(2) ?
N4 C21 C22 O22 . . . . 1.6(3) ?
C26 C21 C22 C23 . . . . 1.9(3) ?
N4 C21 C22 C23 . . . . 179.3(2) ?
O22 C22 C23 C24 . . . . 175.4(2) ?
C21 C22 C23 C24 . . . . -2.1(4) ?
C22 C23 C24 C25 . . . . 0.6(4) ?
C23 C24 C25 C26 . . . . 1.0(4) ?
C24 C25 C26 C21 . . . . -1.1(4) ?
C22 C21 C26 C25 . . . . -0.3(4) ?
N4 C21 C26 C25 . . . . -177.6(2) ?
C23 C22 O22 C27 . . . . 10.9(3) ?
C21 C22 O22 C27 . . . . -171.5(2) ?
C36 C31 C32 C33 . . . . 1.3(4) ?
C37 C31 C32 C33 . . . . -178.7(2) ?
C31 C32 C33 C34 . . . . -0.2(4) ?
C32 C33 C34 C35 . . . . -1.3(4) ?
C32 C33 C34 Cl34 . . . . 179.8(2) ?
C33 C34 C35 C36 . . . . 1.4(5) ?
Cl34 C34 C35 C36 . . . . -179.6(2) ?
C32 C31 C36 C35 . . . . -1.2(5) ?
C37 C31 C36 C35 . . . . 178.9(3) ?
C34 C35 C36 C31 . . . . -0.2(5) ?
C36 C31 C37 O32 . . . . -176.7(3) ?
C32 C31 C37 O32 . . . . 3.3(4) ?
C36 C31 C37 O31 . . . . 3.2(4) ?
C32 C31 C37 O31 . . . . -176.7(3) ?

_cod_database_fobs_code 2243644
