#------------------------------------------------------------------------------
#$Date: 2020-10-31 07:27:38 +0200 (Sat, 31 Oct 2020) $
#$Revision: 258663 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/36/2243653.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_2243653
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 N O4 -'
_chemical_formula_moiety         'C11 H17 N2 O +, C7 H4 N O4 -'
_chemical_formula_sum            'C18 H21 N3 O5'
_chemical_formula_weight         359.38
_chemical_name_systematic
;
4-(2-Methoxyphenyl)piperazin-1-ium 4-nitrobenzoate
;
_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                 97.322(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5174(5)
_cell_length_b                   7.9761(5)
_cell_length_c                   29.860(2)
_cell_measurement_reflns_used    3934
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.884
_cell_measurement_theta_min      2.645
_cell_volume                     1775.8(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  0.0185
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            13660
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.884
_diffrn_reflns_theta_min         2.645
_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    0.099
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.154
_refine_ls_extinction_coef       0.0175(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0457P)²+0.4848P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1112
_reflns_number_gt                2879
_reflns_number_total             3934
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7950sup1.cif
_cod_data_source_block           X
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243653
_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   0.952
_shelx_estimated_absorpt_t_max   0.961
_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 0.44452(18) 0.51582(18) 0.42036(4) 0.0456(3) Uani d 1 . .
H H11 0.359(2) 0.579(2) 0.4356(6) 0.055 Uiso d 1 . .
H H12 0.486(2) 0.426(2) 0.4397(6) 0.055 Uiso d 1 . .
C C2 0.5986(2) 0.6202(2) 0.41168(5) 0.0509(4) Uani d 1 . .
H H2A 0.6633 0.6571 0.4402 0.061 Uiso calc 1 . .
H H2B 0.5558 0.7188 0.3946 0.061 Uiso calc 1 . .
C C3 0.72308(19) 0.5222(2) 0.38567(5) 0.0445(4) Uani d 1 . .
H H3A 0.8229 0.5926 0.3799 0.053 Uiso calc 1 . .
H H3B 0.7707 0.4266 0.4034 0.053 Uiso calc 1 . .
N N4 0.62657(15) 0.46482(15) 0.34309(4) 0.0388(3) Uani d 1 . .
C C5 0.47731(19) 0.3566(2) 0.35153(5) 0.0431(3) Uani d 1 . .
H H5A 0.5234 0.2588 0.3685 0.052 Uiso calc 1 . .
H H5B 0.4140 0.3187 0.3230 0.052 Uiso calc 1 . .
C C6 0.3495(2) 0.4492(2) 0.37760(5) 0.0468(4) Uani d 1 . .
H H6A 0.2950 0.5410 0.3595 0.056 Uiso calc 1 . .
H H6B 0.2548 0.3740 0.3841 0.056 Uiso calc 1 . .
C C21 0.73290(19) 0.39011(18) 0.31211(5) 0.0405(3) Uani d 1 . .
C C22 0.6595(2) 0.3763(2) 0.26645(5) 0.0474(4) Uani d 1 . .
C C23 0.7580(3) 0.3012(2) 0.23580(6) 0.0602(5) Uani d 1 . .
H H23 0.7093 0.2922 0.2057 0.072 Uiso calc 1 . .
C C24 0.9269(3) 0.2400(3) 0.24948(7) 0.0697(5) Uani d 1 . .
H H24 0.9919 0.1898 0.2286 0.084 Uiso calc 1 . .
C C25 1.0000(2) 0.2525(3) 0.29365(7) 0.0695(5) Uani d 1 . .
H H25 1.1143 0.2108 0.3029 0.083 Uiso calc 1 . .
C C26 0.9025(2) 0.3280(2) 0.32471(6) 0.0546(4) Uani d 1 . .
H H26 0.9533 0.3368 0.3547 0.066 Uiso calc 1 . .
O O22 0.49191(17) 0.43933(18) 0.25585(4) 0.0657(4) Uani d 1 . .
C C27 0.4027(3) 0.4122(3) 0.21158(6) 0.0739(6) Uani d 1 . .
H H27A 0.2862 0.4633 0.2088 0.111 Uiso calc 1 . .
H H27B 0.4715 0.4612 0.1900 0.111 Uiso calc 1 . .
H H27C 0.3902 0.2940 0.2061 0.111 Uiso calc 1 . .
C C31 0.16123(19) 0.82005(18) 0.52883(4) 0.0392(3) Uani d 1 . .
C C32 -0.0213(2) 0.79178(19) 0.52353(5) 0.0450(4) Uani d 1 . .
H H32 -0.0716 0.7179 0.5014 0.054 Uiso calc 1 . .
C C33 -0.1305(2) 0.8720(2) 0.55077(5) 0.0458(4) Uani d 1 . .
H H33 -0.2535 0.8531 0.5473 0.055 Uiso calc 1 . .
C C34 -0.05131(19) 0.98058(18) 0.58316(5) 0.0414(3) Uani d 1 . .
C C35 0.1295(2) 1.01111(19) 0.58934(5) 0.0441(4) Uani d 1 . .
H H35 0.1794 1.0853 0.6115 0.053 Uiso calc 1 . .
C C36 0.2358(2) 0.92921(19) 0.56193(5) 0.0435(3) Uani d 1 . .
H H36 0.3590 0.9477 0.5658 0.052 Uiso calc 1 . .
C C37 0.2801(2) 0.73155(19) 0.49920(5) 0.0458(4) Uani d 1 . .
O O31 0.20537(17) 0.67769(17) 0.46209(4) 0.0656(4) Uani d 1 . .
O O32 0.44235(15) 0.71810(15) 0.51349(4) 0.0570(3) Uani d 1 . .
N N34 -0.1638(2) 1.06966(19) 0.61219(5) 0.0541(4) Uani d 1 . .
O O41 -0.32042(19) 1.0270(2) 0.61086(5) 0.0826(4) Uani d 1 . .
O O42 -0.09646(19) 1.18199(18) 0.63615(4) 0.0731(4) 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'
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 . . 110.74(11) ?
C2 N1 H11 . . 111.7(10) ?
C6 N1 H11 . . 108.4(10) ?
C2 N1 H12 . . 109.0(10) ?
C6 N1 H12 . . 109.8(10) ?
H11 N1 H12 . . 107.1(14) ?
N1 C2 C3 . . 110.53(13) ?
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 . . 109.89(12) ?
N4 C3 H3A . . 109.7 ?
C2 C3 H3A . . 109.7 ?
N4 C3 H3B . . 109.7 ?
C2 C3 H3B . . 109.7 ?
H3A C3 H3B . . 108.2 ?
C21 N4 C3 . . 116.07(11) ?
C21 N4 C5 . . 111.75(11) ?
C3 N4 C5 . . 110.07(11) ?
N4 C5 C6 . . 110.72(12) ?
N4 C5 H5A . . 109.5 ?
C6 C5 H5A . . 109.5 ?
N4 C5 H5B . . 109.5 ?
C6 C5 H5B . . 109.5 ?
H5A C5 H5B . . 108.1 ?
N1 C6 C5 . . 110.67(12) ?
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 . . 118.14(14) ?
C26 C21 N4 . . 123.33(13) ?
C22 C21 N4 . . 118.52(13) ?
O22 C22 C23 . . 124.42(14) ?
O22 C22 C21 . . 115.75(13) ?
C23 C22 C21 . . 119.83(15) ?
C24 C23 C22 . . 120.63(16) ?
C24 C23 H23 . . 119.7 ?
C22 C23 H23 . . 119.7 ?
C25 C24 C23 . . 120.23(17) ?
C25 C24 H24 . . 119.9 ?
C23 C24 H24 . . 119.9 ?
C24 C25 C26 . . 119.65(17) ?
C24 C25 H25 . . 120.2 ?
C26 C25 H25 . . 120.2 ?
C21 C26 C25 . . 121.52(16) ?
C21 C26 H26 . . 119.2 ?
C25 C26 H26 . . 119.2 ?
C22 O22 C27 . . 118.37(13) ?
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 ?
C32 C31 C36 . . 119.48(13) ?
C32 C31 C37 . . 120.70(13) ?
C36 C31 C37 . . 119.81(13) ?
C31 C32 C33 . . 120.84(14) ?
C31 C32 H32 . . 119.6 ?
C33 C32 H32 . . 119.6 ?
C34 C33 C32 . . 117.93(14) ?
C34 C33 H33 . . 121.0 ?
C32 C33 H33 . . 121.0 ?
C35 C34 C33 . . 122.65(14) ?
C35 C34 N34 . . 118.04(14) ?
C33 C34 N34 . . 119.30(14) ?
C34 C35 C36 . . 118.40(14) ?
C34 C35 H35 . . 120.8 ?
C36 C35 H35 . . 120.8 ?
C35 C36 C31 . . 120.68(14) ?
C35 C36 H36 . . 119.7 ?
C31 C36 H36 . . 119.7 ?
O32 C37 O31 . . 125.68(14) ?
O32 C37 C31 . . 117.82(13) ?
O31 C37 C31 . . 116.50(14) ?
O42 N34 O41 . . 123.48(15) ?
O42 N34 C34 . . 118.43(14) ?
O41 N34 C34 . . 118.09(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 . 1.476(2) ?
N1 C6 . 1.4798(18) ?
N1 H11 . 0.974(18) ?
N1 H12 . 0.947(18) ?
C2 C3 . 1.508(2) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 N4 . 1.4551(17) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
N4 C21 . 1.4275(18) ?
N4 C5 . 1.4626(18) ?
C5 C6 . 1.505(2) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C21 C26 . 1.375(2) ?
C21 C22 . 1.409(2) ?
C22 O22 . 1.3562(19) ?
C22 C23 . 1.384(2) ?
C23 C24 . 1.373(3) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.366(3) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.390(2) ?
C25 H25 . 0.9300 ?
C26 H26 . 0.9300 ?
O22 C27 . 1.4204(19) ?
C27 H27A . 0.9600 ?
C27 H27B . 0.9600 ?
C27 H27C . 0.9600 ?
C31 C32 . 1.380(2) ?
C31 C36 . 1.381(2) ?
C31 C37 . 1.510(2) ?
C32 C33 . 1.384(2) ?
C32 H32 . 0.9300 ?
C33 C34 . 1.376(2) ?
C33 H33 . 0.9300 ?
C34 C35 . 1.370(2) ?
C34 N34 . 1.4690(19) ?
C35 C36 . 1.379(2) ?
C35 H35 . 0.9300 ?
C36 H36 . 0.9300 ?
C37 O32 . 1.2443(18) ?
C37 O31 . 1.2528(19) ?
N34 O42 . 1.2157(19) ?
N34 O41 . 1.2217(19) ?
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 . 0.974(16) 1.677(16) 2.6500(19) 176.8(15) no
N1 H11 O32 . 0.974(16) 2.581(17) 3.2169(17) 123.0(12) no
N1 H12 O32 3_666 0.948(17) 1.837(17) 2.7709(18) 168.2(16) 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 . . . . -55.83(17) ?
N1 C2 C3 N4 . . . . 58.62(16) ?
C2 C3 N4 C21 . . . . 171.70(12) ?
C2 C3 N4 C5 . . . . -60.13(16) ?
C21 N4 C5 C6 . . . . -170.14(12) ?
C3 N4 C5 C6 . . . . 59.35(15) ?
C2 N1 C6 C5 . . . . 54.67(17) ?
N4 C5 C6 N1 . . . . -56.40(16) ?
C3 N4 C21 C26 . . . . 19.2(2) ?
C5 N4 C21 C26 . . . . -108.17(16) ?
C3 N4 C21 C22 . . . . -162.02(14) ?
C5 N4 C21 C22 . . . . 70.65(17) ?
C26 C21 C22 O22 . . . . 179.94(15) ?
N4 C21 C22 O22 . . . . 1.1(2) ?
C26 C21 C22 C23 . . . . 0.2(2) ?
N4 C21 C22 C23 . . . . -178.64(15) ?
O22 C22 C23 C24 . . . . -179.71(18) ?
C21 C22 C23 C24 . . . . 0.0(3) ?
C22 C23 C24 C25 . . . . 0.0(3) ?
C23 C24 C25 C26 . . . . -0.1(3) ?
C22 C21 C26 C25 . . . . -0.4(3) ?
N4 C21 C26 C25 . . . . 178.42(16) ?
C24 C25 C26 C21 . . . . 0.4(3) ?
C23 C22 O22 C27 . . . . 6.8(3) ?
C21 C22 O22 C27 . . . . -172.93(16) ?
C36 C31 C32 C33 . . . . 0.3(2) ?
C37 C31 C32 C33 . . . . 179.66(13) ?
C31 C32 C33 C34 . . . . 0.1(2) ?
C32 C33 C34 C35 . . . . -0.2(2) ?
C32 C33 C34 N34 . . . . 179.10(13) ?
C33 C34 C35 C36 . . . . -0.1(2) ?
N34 C34 C35 C36 . . . . -179.38(13) ?
C34 C35 C36 C31 . . . . 0.5(2) ?
C32 C31 C36 C35 . . . . -0.6(2) ?
C37 C31 C36 C35 . . . . -179.95(13) ?
C32 C31 C37 O32 . . . . -157.78(15) ?
C36 C31 C37 O32 . . . . 21.5(2) ?
C32 C31 C37 O31 . . . . 22.1(2) ?
C36 C31 C37 O31 . . . . -158.53(15) ?
C35 C34 N34 O42 . . . . 9.5(2) ?
C33 C34 N34 O42 . . . . -169.80(14) ?
C35 C34 N34 O41 . . . . -170.64(15) ?
C33 C34 N34 O41 . . . . 10.0(2) ?

_cod_database_fobs_code 2243653
