#------------------------------------------------------------------------------
#$Date: 2020-10-31 07:27:38 +0200 (Sat, 31 Oct 2020) $
#$Revision: 258663 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/36/2243654.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_2243654
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 H3 N2 O6 -, 2H2 O'
_chemical_formula_moiety         'C11 H17 N2 O +, C7 H3 N2 O6 -, 2(H2 O)'
_chemical_formula_sum            'C18 H24 N4 O9'
_chemical_formula_weight         440.41
_chemical_name_systematic
;
4-(2-Methoxyphenyl)piperazin-1-ium
3,5-dinitrobenzoate dihydrate
;
_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                94.406(7)
_cell_angle_beta                 105.075(8)
_cell_angle_gamma                93.717(7)
_cell_formula_units_Z            2
_cell_length_a                   7.8448(6)
_cell_length_b                   11.4635(9)
_cell_length_c                   12.0747(9)
_cell_measurement_reflns_used    4419
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.694
_cell_measurement_theta_min      2.625
_cell_volume                     1041.33(14)
_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 0.906
_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  0.0157
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7353
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.694
_diffrn_reflns_theta_min         2.625
_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    0.114
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.8919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.480
_exptl_crystal_size_min          0.440
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.171
_refine_ls_extinction_coef       0.052(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0388
_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)+(0.0554P)²+0.1343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1081
_reflns_number_gt                3409
_reflns_number_total             4419
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7950sup1.cif
_cod_data_source_block           XI
_cod_database_code               2243654
_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   0.947
_shelx_estimated_absorpt_t_max   0.952
_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 0.65966(17) 0.38158(10) 0.34243(10) 0.0387(3) Uani d 1 . .
H H11 0.718(2) 0.3310(14) 0.3931(14) 0.046 Uiso d 1 . .
H H12 0.541(2) 0.3638(13) 0.3304(13) 0.046 Uiso d 1 . .
C C2 0.7170(2) 0.37246(12) 0.23459(12) 0.0437(3) Uani d 1 . .
H H2A 0.6800 0.2946 0.1947 0.052 Uiso calc 1 . .
H H2B 0.8452 0.3838 0.2531 0.052 Uiso calc 1 . .
C C3 0.63768(19) 0.46357(11) 0.15669(11) 0.0383(3) Uani d 1 . .
H H3A 0.6811 0.4588 0.0884 0.046 Uiso calc 1 . .
H H3B 0.5097 0.4481 0.1325 0.046 Uiso calc 1 . .
N N4 0.68560(14) 0.58186(8) 0.21770(8) 0.0317(2) Uani d 1 . .
C C5 0.61652(19) 0.58963(11) 0.31932(11) 0.0374(3) Uani d 1 . .
H H5A 0.4888 0.5723 0.2961 0.045 Uiso calc 1 . .
H H5B 0.6431 0.6686 0.3579 0.045 Uiso calc 1 . .
C C6 0.7004(2) 0.50306(12) 0.40043(11) 0.0422(3) Uani d 1 . .
H H6A 0.8278 0.5219 0.4251 0.051 Uiso calc 1 . .
H H6B 0.6557 0.5085 0.4682 0.051 Uiso calc 1 . .
C C21 0.64076(16) 0.67242(10) 0.14284(10) 0.0311(3) Uani d 1 . .
C C22 0.74860(16) 0.69609(11) 0.06906(11) 0.0342(3) Uani d 1 . .
C C23 0.71254(19) 0.78402(12) -0.00441(12) 0.0421(3) Uani d 1 . .
H H23 0.7837 0.7991 -0.0533 0.051 Uiso calc 1 . .
C C24 0.5696(2) 0.84922(12) -0.00446(13) 0.0466(4) Uani d 1 . .
H H24 0.5458 0.9083 -0.0535 0.056 Uiso calc 1 . .
C C25 0.4631(2) 0.82783(12) 0.06667(13) 0.0476(4) Uani d 1 . .
H H25 0.3677 0.8721 0.0660 0.057 Uiso calc 1 . .
C C26 0.49877(18) 0.73919(12) 0.14005(12) 0.0399(3) Uani d 1 . .
H H26 0.4260 0.7245 0.1881 0.048 Uiso calc 1 . .
O O22 0.88764(13) 0.62807(9) 0.07539(9) 0.0471(3) Uani d 1 . .
C C27 1.0094(2) 0.65658(16) 0.01004(16) 0.0601(4) Uani d 1 . .
H H27A 1.1050 0.6069 0.0266 0.090 Uiso calc 1 . .
H H27B 1.0556 0.7372 0.0301 0.090 Uiso calc 1 . .
H H27C 0.9495 0.6448 -0.0706 0.090 Uiso calc 1 . .
C C31 1.07262(16) 0.14162(10) 0.58115(10) 0.0328(3) Uani d 1 . .
C C32 1.23171(17) 0.09894(11) 0.57551(11) 0.0361(3) Uani d 1 . .
H H32 1.2888 0.1233 0.5216 0.043 Uiso calc 1 . .
C C33 1.30429(17) 0.01961(11) 0.65116(12) 0.0384(3) Uani d 1 . .
C C34 1.22367(18) -0.02069(11) 0.73110(12) 0.0406(3) Uani d 1 . .
H H34 1.2719 -0.0765 0.7792 0.049 Uiso calc 1 . .
C C35 1.06862(18) 0.02555(11) 0.73629(11) 0.0376(3) Uani d 1 . .
C C36 0.99163(17) 0.10646(11) 0.66424(11) 0.0356(3) Uani d 1 . .
H H36 0.8874 0.1369 0.6712 0.043 Uiso calc 1 . .
C C37 0.98662(19) 0.22652(11) 0.49671(11) 0.0402(3) Uani d 1 . .
O O31 0.84578(15) 0.26458(10) 0.51102(9) 0.0585(3) Uani d 1 . .
O O32 1.05696(16) 0.24991(11) 0.42026(10) 0.0655(3) Uani d 1 . .
N N33 1.47682(18) -0.02225(14) 0.64945(12) 0.0578(4) Uani d 1 . .
O O33 1.57628(16) 0.04182(15) 0.61300(12) 0.0825(4) Uani d 1 . .
O O34 1.51295(19) -0.11651(13) 0.68590(15) 0.0890(5) Uani d 1 . .
N N35 0.98229(19) -0.01443(13) 0.82304(11) 0.0558(4) Uani d 1 . .
O O35 1.0381(2) -0.09880(14) 0.87252(13) 0.0929(5) Uani d 1 . .
O O36 0.86187(19) 0.03867(14) 0.84155(11) 0.0794(4) Uani d 1 . .
O O41 0.28832(16) 0.36547(12) 0.31241(12) 0.0639(3) Uani d 1 . .
H H41 0.225(3) 0.322(2) 0.341(2) 0.096 Uiso d 1 . .
H H42 0.230(3) 0.431(2) 0.306(2) 0.096 Uiso d 1 . .
O O51 0.13836(19) 0.58148(13) 0.29313(13) 0.0722(4) Uani d 1 . .
H H51 0.152(3) 0.630(2) 0.356(2) 0.087 Uiso d 1 . .
H H52 0.051(3) 0.593(2) 0.250(2) 0.087 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 . . 110.76(10) ?
C2 N1 H11 . . 110.5(10) ?
C6 N1 H11 . . 108.2(9) ?
C2 N1 H12 . . 113.0(10) ?
C6 N1 H12 . . 106.6(10) ?
H11 N1 H12 . . 107.6(13) ?
N1 C2 C3 . . 110.82(11) ?
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 . . 110.21(10) ?
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 C5 . . 115.30(10) ?
C21 N4 C3 . . 112.57(9) ?
C5 N4 C3 . . 109.48(10) ?
N4 C5 C6 . . 109.39(11) ?
N4 C5 H5A . . 109.8 ?
C6 C5 H5A . . 109.8 ?
N4 C5 H5B . . 109.8 ?
C6 C5 H5B . . 109.8 ?
H5A C5 H5B . . 108.2 ?
N1 C6 C5 . . 110.28(11) ?
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 . . 118.27(11) ?
C26 C21 N4 . . 123.70(11) ?
C22 C21 N4 . . 118.02(11) ?
O22 C22 C23 . . 123.48(12) ?
O22 C22 C21 . . 116.04(10) ?
C23 C22 C21 . . 120.48(12) ?
C24 C23 C22 . . 119.57(13) ?
C24 C23 H23 . . 120.2 ?
C22 C23 H23 . . 120.2 ?
C25 C24 C23 . . 120.95(12) ?
C25 C24 H24 . . 119.5 ?
C23 C24 H24 . . 119.5 ?
C24 C25 C26 . . 119.49(13) ?
C24 C25 H25 . . 120.3 ?
C26 C25 H25 . . 120.3 ?
C21 C26 C25 . . 121.23(13) ?
C21 C26 H26 . . 119.4 ?
C25 C26 H26 . . 119.4 ?
C22 O22 C27 . . 117.66(11) ?
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 . . 119.65(11) ?
C32 C31 C37 . . 120.23(11) ?
C36 C31 C37 . . 120.12(12) ?
C33 C32 C31 . . 118.99(12) ?
C33 C32 H32 . . 120.5 ?
C31 C32 H32 . . 120.5 ?
C34 C33 C32 . . 122.75(12) ?
C34 C33 N33 . . 117.76(12) ?
C32 C33 N33 . . 119.48(13) ?
C35 C34 C33 . . 116.72(12) ?
C35 C34 H34 . . 121.6 ?
C33 C34 H34 . . 121.6 ?
C34 C35 C36 . . 122.99(12) ?
C34 C35 N35 . . 117.58(12) ?
C36 C35 N35 . . 119.42(12) ?
C35 C36 C31 . . 118.82(12) ?
C35 C36 H36 . . 120.6 ?
C31 C36 H36 . . 120.6 ?
O32 C37 O31 . . 125.98(13) ?
O32 C37 C31 . . 118.05(13) ?
O31 C37 C31 . . 115.95(12) ?
O34 N33 O33 . . 124.40(15) ?
O34 N33 C33 . . 118.57(15) ?
O33 N33 C33 . . 117.02(14) ?
O36 N35 O35 . . 124.28(14) ?
O36 N35 C35 . . 118.33(13) ?
O35 N35 C35 . . 117.39(15) ?
H41 O41 H42 . . 102(2) ?
H51 O51 H52 . . 108(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 C2 . 1.4826(18) ?
N1 C6 . 1.4860(18) ?
N1 H11 . 0.929(16) ?
N1 H12 . 0.908(16) ?
C2 C3 . 1.5143(17) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 N4 . 1.4694(16) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
N4 C21 . 1.4300(15) ?
N4 C5 . 1.4638(16) ?
C5 C6 . 1.5086(18) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C21 C26 . 1.3866(18) ?
C21 C22 . 1.4080(17) ?
C22 O22 . 1.3709(16) ?
C22 C23 . 1.3881(17) ?
C23 C24 . 1.387(2) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.369(2) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.3936(19) ?
C25 H25 . 0.9300 ?
C26 H26 . 0.9300 ?
O22 C27 . 1.4257(17) ?
C27 H27A . 0.9600 ?
C27 H27B . 0.9600 ?
C27 H27C . 0.9600 ?
C31 C32 . 1.3856(19) ?
C31 C36 . 1.3903(17) ?
C31 C37 . 1.5237(17) ?
C32 C33 . 1.3820(18) ?
C32 H32 . 0.9300 ?
C33 C34 . 1.3759(19) ?
C33 N33 . 1.4696(19) ?
C34 C35 . 1.372(2) ?
C34 H34 . 0.9300 ?
C35 C36 . 1.3803(17) ?
C35 N35 . 1.4727(17) ?
C36 H36 . 0.9300 ?
C37 O32 . 1.2297(17) ?
C37 O31 . 1.2615(18) ?
N33 O34 . 1.2204(19) ?
N33 O33 . 1.2231(19) ?
N35 O36 . 1.2150(19) ?
N35 O35 . 1.2214(18) ?
O41 H41 . 0.84(2) ?
O41 H42 . 0.91(3) ?
O51 H51 . 0.88(2) ?
O51 H52 . 0.77(2) ?
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 . 0.929(16) 1.771(16) 2.6837(16) 166.8(15) no
N1 H12 O41 . 0.911(16) 1.939(16) 2.8324(19) 165.5(14) no
O41 H41 O32 1_455 0.84(2) 1.99(2) 2.8156(19) 168(2) no
O41 H42 O51 . 0.90(2) 1.91(2) 2.810(2) 172(2) no
O51 H51 O31 2_666 0.90(2) 1.91(2) 2.810(2) 172(2) no
O51 H52 O22 1_455 0.77(2) 2.25(2) 2.9544(19) 153(2) no
C25 H25 O36 2_666 0.93 2.58 3.433(2) 153 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 . . . . -54.19(15) ?
N1 C2 C3 N4 . . . . 56.54(15) ?
C2 C3 N4 C21 . . . . 169.85(11) ?
C2 C3 N4 C5 . . . . -60.51(14) ?
C21 N4 C5 C6 . . . . -169.80(10) ?
C3 N4 C5 C6 . . . . 62.06(13) ?
C2 N1 C6 C5 . . . . 55.87(15) ?
N4 C5 C6 N1 . . . . -59.79(14) ?
C5 N4 C21 C26 . . . . -21.15(17) ?
C3 N4 C21 C26 . . . . 105.44(14) ?
C5 N4 C21 C22 . . . . 157.91(11) ?
C3 N4 C21 C22 . . . . -75.51(14) ?
C26 C21 C22 O22 . . . . 179.73(11) ?
N4 C21 C22 O22 . . . . 0.62(16) ?
C26 C21 C22 C23 . . . . -0.10(18) ?
N4 C21 C22 C23 . . . . -179.21(11) ?
O22 C22 C23 C24 . . . . -179.50(13) ?
C21 C22 C23 C24 . . . . 0.3(2) ?
C22 C23 C24 C25 . . . . -0.2(2) ?
C23 C24 C25 C26 . . . . -0.1(2) ?
C22 C21 C26 C25 . . . . -0.20(19) ?
N4 C21 C26 C25 . . . . 178.85(12) ?
C24 C25 C26 C21 . . . . 0.3(2) ?
C23 C22 O22 C27 . . . . 5.6(2) ?
C21 C22 O22 C27 . . . . -174.26(12) ?
C36 C31 C32 C33 . . . . 1.65(18) ?
C37 C31 C32 C33 . . . . -178.27(11) ?
C31 C32 C33 C34 . . . . 1.13(19) ?
C31 C32 C33 N33 . . . . -177.30(12) ?
C32 C33 C34 C35 . . . . -2.7(2) ?
N33 C33 C34 C35 . . . . 175.77(12) ?
C33 C34 C35 C36 . . . . 1.5(2) ?
C33 C34 C35 N35 . . . . -178.66(12) ?
C34 C35 C36 C31 . . . . 1.1(2) ?
N35 C35 C36 C31 . . . . -178.69(12) ?
C32 C31 C36 C35 . . . . -2.72(18) ?
C37 C31 C36 C35 . . . . 177.21(11) ?
C32 C31 C37 O32 . . . . 4.20(18) ?
C36 C31 C37 O32 . . . . -175.73(13) ?
C32 C31 C37 O31 . . . . -177.24(13) ?
C36 C31 C37 O31 . . . . 2.83(18) ?
C34 C33 N33 O34 . . . . 25.3(2) ?
C32 C33 N33 O34 . . . . -156.20(15) ?
C34 C33 N33 O33 . . . . -153.41(14) ?
C32 C33 N33 O33 . . . . 25.1(2) ?
C34 C35 N35 O36 . . . . 168.36(14) ?
C36 C35 N35 O36 . . . . -11.8(2) ?
C34 C35 N35 O35 . . . . -11.0(2) ?
C36 C35 N35 O35 . . . . 168.77(14) ?

_cod_database_fobs_code 2243654
