#------------------------------------------------------------------------------
#$Date: 2020-10-31 07:27:38 +0200 (Sat, 31 Oct 2020) $
#$Revision: 258663 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/36/2243648.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_2243648
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 2-chlorobenzoate
;
_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                 106.400(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9974(8)
_cell_length_b                   27.611(2)
_cell_length_c                   8.5972(9)
_cell_measurement_reflns_used    4043
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.998
_cell_measurement_theta_min      2.577
_cell_volume                     1821.2(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.999
_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  0.0304
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13275
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.549
_diffrn_reflns_theta_min         2.577
_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    0.229
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_refine_diff_density_max         1.147
_refine_diff_density_min         -0.295
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3410
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0670
_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)+(0.1138P)²+0.7483P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1885
_refine_ls_wR_factor_ref         0.2161
_reflns_number_gt                2060
_reflns_number_total             3410
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7950sup1.cif
_cod_data_source_block           V
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243648
_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   0.898
_shelx_estimated_absorpt_t_max   0.973
_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 0.4620(4) 0.44249(11) 0.3578(4) 0.0640(8) Uani d 1 . .
H H11 0.368(5) 0.4525(14) 0.402(4) 0.077 Uiso d 1 . .
H H12 0.511(5) 0.4709(16) 0.336(4) 0.077 Uiso d 1 . .
C C2 0.3954(4) 0.41253(14) 0.2112(5) 0.0684(10) Uani d 1 . .
H H2A 0.3246 0.4323 0.1241 0.082 Uiso calc 1 . .
H H2B 0.3225 0.3869 0.2333 0.082 Uiso calc 1 . .
C C3 0.5449(4) 0.39067(13) 0.1593(4) 0.0614(9) Uani d 1 . .
H H3A 0.4993 0.3699 0.0659 0.074 Uiso calc 1 . .
H H3B 0.6122 0.4163 0.1284 0.074 Uiso calc 1 . .
N N4 0.6572(3) 0.36247(10) 0.2916(3) 0.0545(7) Uani d 1 . .
C C5 0.7325(5) 0.39472(14) 0.4289(4) 0.0666(10) Uani d 1 . .
H H5A 0.7975 0.4204 0.3957 0.080 Uiso calc 1 . .
H H5B 0.8118 0.3767 0.5159 0.080 Uiso calc 1 . .
C C6 0.5886(5) 0.41589(16) 0.4871(5) 0.0747(11) Uani d 1 . .
H H6A 0.5290 0.3901 0.5265 0.090 Uiso calc 1 . .
H H6B 0.6379 0.4377 0.5769 0.090 Uiso calc 1 . .
C C21 0.7769(4) 0.33160(12) 0.2452(4) 0.0538(8) Uani d 1 . .
C C22 0.7097(5) 0.29139(12) 0.1470(4) 0.0607(9) Uani d 1 . .
C C23 0.8208(7) 0.26032(14) 0.0999(5) 0.0798(12) Uani d 1 . .
H H23 0.7765 0.2342 0.0326 0.096 Uiso calc 1 . .
C C24 1.0003(7) 0.26825(19) 0.1536(6) 0.0962(16) Uani d 1 . .
H H24 1.0751 0.2470 0.1223 0.115 Uiso calc 1 . .
C C25 1.0676(6) 0.30630(18) 0.2506(6) 0.0869(13) Uani d 1 . .
H H25 1.1875 0.3109 0.2868 0.104 Uiso calc 1 . .
C C26 0.9558(5) 0.33835(14) 0.2954(4) 0.0672(10) Uani d 1 . .
H H26 1.0018 0.3648 0.3602 0.081 Uiso calc 1 . .
O O22 0.5338(3) 0.28580(9) 0.1060(3) 0.0770(8) Uani d 1 . .
C C27 0.4570(7) 0.24698(17) 0.0025(6) 0.1036(16) Uani d 1 . .
H H27A 0.3330 0.2476 -0.0157 0.155 Uiso calc 1 . .
H H27B 0.4835 0.2502 -0.0992 0.155 Uiso calc 1 . .
H H27C 0.5027 0.2168 0.0522 0.155 Uiso calc 1 . .
C C31 0.1308(4) 0.43466(12) 0.7353(4) 0.0541(8) Uani d 1 . .
C C32 0.1418(4) 0.38566(13) 0.7729(4) 0.0606(9) Uani d 1 . .
Cl Cl32 0.29281(16) 0.35006(4) 0.71550(13) 0.0871(4) Uani d 1 . .
C C33 0.0387(6) 0.36423(19) 0.8551(5) 0.0886(13) Uani d 1 . .
H H33 0.0482 0.3312 0.8774 0.106 Uiso calc 1 . .
C C34 -0.0776(7) 0.3916(3) 0.9036(6) 0.1056(17) Uani d 1 . .
H H34 -0.1480 0.3772 0.9600 0.127 Uiso calc 1 . .
C C35 -0.0935(6) 0.4406(2) 0.8710(5) 0.0955(15) Uani d 1 . .
H H35 -0.1735 0.4591 0.9055 0.115 Uiso calc 1 . .
C C36 0.0107(5) 0.46182(16) 0.7865(5) 0.0760(11) Uani d 1 . .
H H36 0.0000 0.4948 0.7637 0.091 Uiso calc 1 . .
C C37 0.2417(5) 0.45733(12) 0.6402(5) 0.0643(9) Uani d 1 . .
O O31 0.1985(3) 0.45110(11) 0.4917(3) 0.0810(8) Uani d 1 . .
O O32 0.3701(5) 0.48041(13) 0.7200(4) 0.1152(12) 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 . . 111.8(3) ?
C6 N1 H11 . . 107(2) ?
C2 N1 H11 . . 111(2) ?
C6 N1 H12 . . 110(2) ?
C2 N1 H12 . . 112(2) ?
H11 N1 H12 . . 105(3) ?
N1 C2 C3 . . 110.5(3) ?
N1 C2 H2A . . 109.5 ?
C3 C2 H2A . . 109.5 ?
N1 C2 H2B . . 109.5 ?
C3 C2 H2B . . 109.5 ?
H2A C2 H2B . . 108.1 ?
N4 C3 C2 . . 110.3(3) ?
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 . . 114.6(2) ?
C21 N4 C5 . . 115.8(3) ?
C3 N4 C5 . . 109.0(3) ?
N4 C5 C6 . . 109.1(3) ?
N4 C5 H5A . . 109.9 ?
C6 C5 H5A . . 109.9 ?
N4 C5 H5B . . 109.9 ?
C6 C5 H5B . . 109.9 ?
H5A C5 H5B . . 108.3 ?
N1 C6 C5 . . 111.8(3) ?
N1 C6 H6A . . 109.2 ?
C5 C6 H6A . . 109.2 ?
N1 C6 H6B . . 109.2 ?
C5 C6 H6B . . 109.2 ?
H6A C6 H6B . . 107.9 ?
C26 C21 C22 . . 118.6(3) ?
C26 C21 N4 . . 123.4(3) ?
C22 C21 N4 . . 118.0(3) ?
O22 C22 C23 . . 124.1(4) ?
O22 C22 C21 . . 115.9(3) ?
C23 C22 C21 . . 120.0(4) ?
C22 C23 C24 . . 119.6(4) ?
C22 C23 H23 . . 120.2 ?
C24 C23 H23 . . 120.2 ?
C25 C24 C23 . . 121.2(4) ?
C25 C24 H24 . . 119.4 ?
C23 C24 H24 . . 119.4 ?
C24 C25 C26 . . 119.4(4) ?
C24 C25 H25 . . 120.3 ?
C26 C25 H25 . . 120.3 ?
C21 C26 C25 . . 121.2(4) ?
C21 C26 H26 . . 119.4 ?
C25 C26 H26 . . 119.4 ?
C22 O22 C27 . . 118.8(3) ?
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 . . 117.3(3) ?
C36 C31 C37 . . 121.1(3) ?
C32 C31 C37 . . 121.6(3) ?
C33 C32 C31 . . 122.4(4) ?
C33 C32 Cl32 . . 118.2(3) ?
C31 C32 Cl32 . . 119.4(3) ?
C34 C33 C32 . . 119.1(5) ?
C34 C33 H33 . . 120.5 ?
C32 C33 H33 . . 120.5 ?
C33 C34 C35 . . 121.1(4) ?
C33 C34 H34 . . 119.4 ?
C35 C34 H34 . . 119.4 ?
C34 C35 C36 . . 119.3(4) ?
C34 C35 H35 . . 120.4 ?
C36 C35 H35 . . 120.4 ?
C35 C36 C31 . . 120.8(4) ?
C35 C36 H36 . . 119.6 ?
C31 C36 H36 . . 119.6 ?
O31 C37 O32 . . 126.2(4) ?
O31 C37 C31 . . 117.9(3) ?
O32 C37 C31 . . 115.9(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
N1 C6 . 1.472(5) ?
N1 C2 . 1.475(4) ?
N1 H11 . 0.97(4) ?
N1 H12 . 0.92(4) ?
C2 C3 . 1.515(5) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 N4 . 1.460(4) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
N4 C21 . 1.421(4) ?
N4 C5 . 1.465(4) ?
C5 C6 . 1.497(5) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C21 C26 . 1.385(5) ?
C21 C22 . 1.407(5) ?
C22 O22 . 1.359(4) ?
C22 C23 . 1.375(5) ?
C23 C24 . 1.395(6) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.355(7) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.387(6) ?
C25 H25 . 0.9300 ?
C26 H26 . 0.9300 ?
O22 C27 . 1.418(4) ?
C27 H27A . 0.9600 ?
C27 H27B . 0.9600 ?
C27 H27C . 0.9600 ?
C31 C36 . 1.385(5) ?
C31 C32 . 1.388(5) ?
C31 C37 . 1.503(5) ?
C32 C33 . 1.363(5) ?
C32 Cl32 . 1.733(4) ?
C33 C34 . 1.354(7) ?
C33 H33 . 0.9300 ?
C34 C35 . 1.378(7) ?
C34 H34 . 0.9300 ?
C35 C36 . 1.381(6) ?
C35 H35 . 0.9300 ?
C36 H36 . 0.9300 ?
C37 O31 . 1.237(5) ?
C37 O32 . 1.238(5) ?
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 . 0.97(4) 1.74(3) 2.682(4) 162(3) no
N1 H12 O32 3_666 0.92(4) 1.79(4) 2.700(5) 170(4) no
C5 H5B Cg1 1_655 0.97 2.87 3.554(4) 128 no
C34 H34 Cg2 1_456 0.93 2.93 3.658(7) 136 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 . . . . -51.8(4) ?
N1 C2 C3 N4 . . . . 56.7(4) ?
C2 C3 N4 C21 . . . . 166.2(3) ?
C2 C3 N4 C5 . . . . -62.2(3) ?
C21 N4 C5 C6 . . . . -166.8(3) ?
C3 N4 C5 C6 . . . . 62.2(4) ?
C2 N1 C6 C5 . . . . 53.2(4) ?
N4 C5 C6 N1 . . . . -58.0(4) ?
C3 N4 C21 C26 . . . . 112.9(3) ?
C5 N4 C21 C26 . . . . -15.3(4) ?
C3 N4 C21 C22 . . . . -68.9(4) ?
C5 N4 C21 C22 . . . . 162.8(3) ?
C26 C21 C22 O22 . . . . 177.9(3) ?
N4 C21 C22 O22 . . . . -0.3(4) ?
C26 C21 C22 C23 . . . . -1.4(5) ?
N4 C21 C22 C23 . . . . -179.6(3) ?
O22 C22 C23 C24 . . . . -177.6(4) ?
C21 C22 C23 C24 . . . . 1.7(5) ?
C22 C23 C24 C25 . . . . -0.5(6) ?
C23 C24 C25 C26 . . . . -0.9(6) ?
C22 C21 C26 C25 . . . . -0.1(5) ?
N4 C21 C26 C25 . . . . 178.0(3) ?
C24 C25 C26 C21 . . . . 1.3(6) ?
C23 C22 O22 C27 . . . . -2.9(5) ?
C21 C22 O22 C27 . . . . 177.8(3) ?
C36 C31 C32 C33 . . . . 0.7(5) ?
C37 C31 C32 C33 . . . . -178.1(4) ?
C36 C31 C32 Cl32 . . . . -178.7(3) ?
C37 C31 C32 Cl32 . . . . 2.4(4) ?
C31 C32 C33 C34 . . . . -0.7(6) ?
Cl32 C32 C33 C34 . . . . 178.7(3) ?
C32 C33 C34 C35 . . . . 0.2(7) ?
C33 C34 C35 C36 . . . . 0.3(7) ?
C34 C35 C36 C31 . . . . -0.3(6) ?
C32 C31 C36 C35 . . . . -0.2(5) ?
C37 C31 C36 C35 . . . . 178.6(4) ?
C36 C31 C37 O31 . . . . -101.0(4) ?
C32 C31 C37 O31 . . . . 77.8(4) ?
C36 C31 C37 O32 . . . . 79.5(4) ?
C32 C31 C37 O32 . . . . -101.7(4) ?

_cod_database_fobs_code 2243648
