#------------------------------------------------------------------------------
#$Date: 2020-10-31 07:27:38 +0200 (Sat, 31 Oct 2020) $
#$Revision: 258663 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/36/2243652.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_2243652
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 H6 N O2 -'
_chemical_formula_moiety         'C11 H17 N2 O +, C7 H6 N O2 -'
_chemical_formula_sum            'C18 H23 N3 O3'
_chemical_formula_weight         329.39
_chemical_name_systematic
;
4-(2-Methoxyphenyl)piperazin-1-ium 4-aminobenzoate
;
_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     difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 106.911(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9220(10)
_cell_length_b                   7.6951(5)
_cell_length_c                   15.5600(10)
_cell_measurement_reflns_used    3671
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.767
_cell_measurement_theta_min      2.693
_cell_volume                     1709.4(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 0.930
_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  0.0143
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6720
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.550
_diffrn_reflns_theta_min         2.693
_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    0.088
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.245
_refine_ls_extinction_coef       0.019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3668
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0389
_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)+(0.0619P)²+0.0395P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1120
_reflns_number_gt                2606
_reflns_number_total             3668
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7950sup1.cif
_cod_data_source_block           IX
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243652
_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   0.959
_shelx_estimated_absorpt_t_max   0.986
_shelxl_version_number           2.014
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 0.60709(8) 0.26835(15) 0.52995(8) 0.0431(3) Uani d 1 . .
H H11 0.5586(10) 0.2606(17) 0.4643(10) 0.052 Uiso d 1 . .
H H12 0.5953(10) 0.3661(19) 0.5615(10) 0.052 Uiso d 1 . .
C C2 0.70246(9) 0.28650(18) 0.51932(9) 0.0442(3) Uani d 1 . .
H H2A 0.7056 0.3915 0.4858 0.053 Uiso calc 1 . .
H H2B 0.7155 0.1883 0.4857 0.053 Uiso calc 1 . .
C C3 0.77450(9) 0.29453(16) 0.60945(8) 0.0385(3) Uani d 1 . .
H H3A 0.8364 0.3050 0.6015 0.046 Uiso calc 1 . .
H H3B 0.7635 0.3963 0.6417 0.046 Uiso calc 1 . .
N N4 0.77041(7) 0.13685(13) 0.66227(7) 0.0376(3) Uani d 1 . .
C C5 0.67672(9) 0.11904(18) 0.67358(9) 0.0433(3) Uani d 1 . .
H H5A 0.6642 0.2174 0.7074 0.052 Uiso calc 1 . .
H H5B 0.6741 0.0143 0.7074 0.052 Uiso calc 1 . .
C C6 0.60307(9) 0.11039(17) 0.58382(9) 0.0458(3) Uani d 1 . .
H H6A 0.6131 0.0079 0.5515 0.055 Uiso calc 1 . .
H H6B 0.5416 0.1013 0.5928 0.055 Uiso calc 1 . .
C C21 0.84580(9) 0.13068(16) 0.74309(9) 0.0409(3) Uani d 1 . .
C C22 0.93798(9) 0.11685(17) 0.73737(10) 0.0460(3) Uani d 1 . .
C C23 1.01328(10) 0.1198(2) 0.81461(11) 0.0600(4) Uani d 1 . .
H H23 1.0740 0.1142 0.8102 0.072 Uiso calc 1 . .
C C24 0.99867(13) 0.1311(2) 0.89743(11) 0.0714(5) Uani d 1 . .
H H24 1.0495 0.1345 0.9489 0.086 Uiso calc 1 . .
C C25 0.90983(13) 0.1373(3) 0.90449(11) 0.0732(5) Uani d 1 . .
H H25 0.9001 0.1412 0.9608 0.088 Uiso calc 1 . .
C C26 0.83373(11) 0.1379(2) 0.82761(9) 0.0559(4) Uani d 1 . .
H H26 0.7734 0.1432 0.8332 0.067 Uiso calc 1 . .
O O22 0.94654(7) 0.10004(14) 0.65293(7) 0.0603(3) Uani d 1 . .
C C27 1.03816(12) 0.1063(3) 0.64265(13) 0.0762(5) Uani d 1 . .
H H27A 1.0342 0.0973 0.5801 0.114 Uiso calc 1 . .
H H27B 1.0747 0.0114 0.6749 0.114 Uiso calc 1 . .
H H27C 1.0675 0.2142 0.6660 0.114 Uiso calc 1 . .
C C31 0.38418(8) 0.30821(15) 0.23323(8) 0.0341(3) Uani d 1 . .
C C32 0.30092(9) 0.39385(17) 0.19135(9) 0.0410(3) Uani d 1 . .
H H32 0.2734 0.4636 0.2255 0.049 Uiso calc 1 . .
C C33 0.25815(9) 0.37762(17) 0.10033(9) 0.0429(3) Uani d 1 . .
H H33 0.2021 0.4355 0.0741 0.051 Uiso calc 1 . .
C C34 0.29810(9) 0.27553(16) 0.04752(8) 0.0373(3) Uani d 1 . .
C C35 0.38187(9) 0.19061(17) 0.08919(8) 0.0395(3) Uani d 1 . .
H H35 0.4102 0.1226 0.0551 0.047 Uiso calc 1 . .
C C36 0.42342(9) 0.20608(16) 0.18038(9) 0.0382(3) Uani d 1 . .
H H36 0.4789 0.1468 0.2069 0.046 Uiso calc 1 . .
C C37 0.43113(9) 0.32513(16) 0.33203(8) 0.0379(3) Uani d 1 . .
O O31 0.50355(7) 0.23691(14) 0.36411(6) 0.0627(3) Uani d 1 . .
O O32 0.39544(7) 0.42404(13) 0.37713(6) 0.0526(3) Uani d 1 . .
N N34 0.25457(10) 0.25415(18) -0.04368(8) 0.0501(3) Uani d 1 . .
H H341 0.2158(11) 0.340(2) -0.0658(11) 0.060 Uiso d 1 . .
H H342 0.2928(11) 0.211(2) -0.0750(10) 0.060 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
C2 N1 C6 . . 109.66(10) ?
C2 N1 H11 . . 107.7(8) ?
C6 N1 H11 . . 111.5(7) ?
C2 N1 H12 . . 108.2(9) ?
C6 N1 H12 . . 108.3(9) ?
H11 N1 H12 . . 111.5(11) ?
N1 C2 C3 . . 110.42(11) ?
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 . . 110.62(10) ?
N4 C3 H3A . . 109.5 ?
C2 C3 H3A . . 109.5 ?
N4 C3 H3B . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 108.1 ?
C21 N4 C5 . . 115.29(10) ?
C21 N4 C3 . . 111.66(9) ?
C5 N4 C3 . . 109.81(9) ?
N4 C5 C6 . . 110.91(11) ?
N4 C5 H5A . . 109.5 ?
C6 C5 H5A . . 109.5 ?
N4 C5 H5B . . 109.5 ?
C6 C5 H5B . . 109.5 ?
H5A C5 H5B . . 108.0 ?
N1 C6 C5 . . 110.38(10) ?
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 . . 117.66(13) ?
C26 C21 N4 . . 123.51(12) ?
C22 C21 N4 . . 118.83(12) ?
O22 C22 C23 . . 123.91(13) ?
O22 C22 C21 . . 115.81(12) ?
C23 C22 C21 . . 120.28(14) ?
C24 C23 C22 . . 120.38(15) ?
C24 C23 H23 . . 119.8 ?
C22 C23 H23 . . 119.8 ?
C25 C24 C23 . . 120.16(15) ?
C25 C24 H24 . . 119.9 ?
C23 C24 H24 . . 119.9 ?
C24 C25 C26 . . 120.10(16) ?
C24 C25 H25 . . 119.9 ?
C26 C25 H25 . . 120.0 ?
C21 C26 C25 . . 121.33(15) ?
C21 C26 H26 . . 119.3 ?
C25 C26 H26 . . 119.3 ?
C22 O22 C27 . . 117.90(12) ?
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 . . 117.75(11) ?
C36 C31 C37 . . 120.43(11) ?
C32 C31 C37 . . 121.82(11) ?
C33 C32 C31 . . 121.46(12) ?
C33 C32 H32 . . 119.3 ?
C31 C32 H32 . . 119.3 ?
C32 C33 C34 . . 120.54(12) ?
C32 C33 H33 . . 119.7 ?
C34 C33 H33 . . 119.7 ?
N34 C34 C33 . . 121.17(12) ?
N34 C34 C35 . . 120.69(12) ?
C33 C34 C35 . . 118.11(11) ?
C36 C35 C34 . . 120.86(11) ?
C36 C35 H35 . . 119.6 ?
C34 C35 H35 . . 119.6 ?
C35 C36 C31 . . 121.27(12) ?
C35 C36 H36 . . 119.4 ?
C31 C36 H36 . . 119.4 ?
O31 C37 O32 . . 124.36(12) ?
O31 C37 C31 . . 117.02(11) ?
O32 C37 C31 . . 118.62(11) ?
C34 N34 H341 . . 111.8(11) ?
C34 N34 H342 . . 114.2(10) ?
H341 N34 H342 . . 120.4(15) ?
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 C2 . 1.4864(18) ?
N1 C6 . 1.4875(18) ?
N1 H11 . 1.067(14) ?
N1 H12 . 0.942(15) ?
C2 C3 . 1.4997(16) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 N4 . 1.4768(15) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
N4 C21 . 1.4235(16) ?
N4 C5 . 1.4654(16) ?
C5 C6 . 1.5067(18) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C21 C26 . 1.380(2) ?
C21 C22 . 1.4079(19) ?
C22 O22 . 1.3627(17) ?
C22 C23 . 1.3863(19) ?
C23 C24 . 1.371(2) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.363(2) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.389(2) ?
C25 H25 . 0.9300 ?
C26 H26 . 0.9300 ?
O22 C27 . 1.4228(18) ?
C27 H27A . 0.9600 ?
C27 H27B . 0.9600 ?
C27 H27C . 0.9600 ?
C31 C36 . 1.3844(17) ?
C31 C32 . 1.3897(17) ?
C31 C37 . 1.4982(16) ?
C32 C33 . 1.3796(18) ?
C32 H32 . 0.9300 ?
C33 C34 . 1.3902(18) ?
C33 H33 . 0.9300 ?
C34 N34 . 1.3881(16) ?
C34 C35 . 1.3923(18) ?
C35 C36 . 1.3784(17) ?
C35 H35 . 0.9300 ?
C36 H36 . 0.9300 ?
C37 O31 . 1.2506(16) ?
C37 O32 . 1.2542(15) ?
N34 H341 . 0.877(16) ?
N34 H342 . 0.913(16) ?
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 . 1.068(15) 1.547(15) 2.6048(15) 169.7(14) no
N1 H12 O32 3_666 0.942(15) 1.861(15) 2.7797(15) 164.4(14) no
N34 H342 O32 4_565 0.914(16) 2.155(16) 3.0535(18) 167.5(14) 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 . . . . -57.43(14) ?
N1 C2 C3 N4 . . . . 58.53(13) ?
C2 C3 N4 C21 . . . . 172.34(11) ?
C2 C3 N4 C5 . . . . -58.48(13) ?
C21 N4 C5 C6 . . . . -174.66(10) ?
C3 N4 C5 C6 . . . . 58.16(13) ?
C2 N1 C6 C5 . . . . 56.92(14) ?
N4 C5 C6 N1 . . . . -57.96(14) ?
C5 N4 C21 C26 . . . . -10.87(18) ?
C3 N4 C21 C26 . . . . 115.36(14) ?
C5 N4 C21 C22 . . . . 169.26(11) ?
C3 N4 C21 C22 . . . . -64.51(14) ?
C26 C21 C22 O22 . . . . 176.36(13) ?
N4 C21 C22 O22 . . . . -3.76(17) ?
C26 C21 C22 C23 . . . . -3.3(2) ?
N4 C21 C22 C23 . . . . 176.56(11) ?
O22 C22 C23 C24 . . . . -177.72(15) ?
C21 C22 C23 C24 . . . . 1.9(2) ?
C22 C23 C24 C25 . . . . 0.8(3) ?
C23 C24 C25 C26 . . . . -2.1(3) ?
C22 C21 C26 C25 . . . . 2.1(2) ?
N4 C21 C26 C25 . . . . -177.79(13) ?
C24 C25 C26 C21 . . . . 0.6(3) ?
C23 C22 O22 C27 . . . . -7.6(2) ?
C21 C22 O22 C27 . . . . 172.72(13) ?
C36 C31 C32 C33 . . . . 0.31(19) ?
C37 C31 C32 C33 . . . . 179.98(12) ?
C31 C32 C33 C34 . . . . -0.6(2) ?
C32 C33 C34 N34 . . . . 178.21(12) ?
C32 C33 C34 C35 . . . . 0.14(19) ?
N34 C34 C35 C36 . . . . -177.43(12) ?
C33 C34 C35 C36 . . . . 0.65(19) ?
C34 C35 C36 C31 . . . . -0.97(19) ?
C32 C31 C36 C35 . . . . 0.48(19) ?
C37 C31 C36 C35 . . . . -179.20(11) ?
C36 C31 C37 O31 . . . . -3.44(17) ?
C32 C31 C37 O31 . . . . 176.90(13) ?
C36 C31 C37 O32 . . . . 177.29(12) ?
C32 C31 C37 O32 . . . . -2.37(18) ?

_cod_database_fobs_code 2243652
