#------------------------------------------------------------------------------
#$Date: 2020-10-31 07:27:38 +0200 (Sat, 31 Oct 2020) $
#$Revision: 258663 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/36/2243658.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_2243658
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_absolute_configuration syn
_chemical_formula_iupac          'C11 H17 N2 O +, C4 H5 O6 -, 1.698H2 O'
_chemical_formula_moiety         'C11 H17 N2 O +, C4 H5 O6 -, 1.698(H2 O)'
_chemical_formula_sum            'C15 H25.4 N2 O8.7'
_chemical_formula_weight         372.97
_chemical_name_systematic
;
4-(2-Methoxyphenyl)piperazin-1-ium hydrogen (2R,3R)-tartrate
1.698-hydrate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 101.58(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.4790(10)
_cell_length_b                   7.0650(10)
_cell_length_c                   17.788(3)
_cell_measurement_reflns_used    2896
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.877
_cell_measurement_theta_min      3.111
_cell_volume                     920.8(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 0.994
_diffrn_measured_fraction_theta_max 0.915
_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  0.0223
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            3655
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.877
_diffrn_reflns_theta_min         3.111
_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    0.111
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       plate
_exptl_crystal_F_000             398
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.169
_refine_ls_abs_structure_details
;
Flack x determined using 493 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         2895
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0393
_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)+(0.0402P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0810
_reflns_number_gt                2062
_reflns_number_total             2895
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7950sup1.cif
_cod_data_source_block           XV
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C15 H25.40 N2 O8.70'
_cod_database_code               2243658
_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   0.961
_shelx_estimated_absorpt_t_max   0.987
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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 0.4545(5) 0.3626(4) 0.31605(16) 0.0472(7) Uani d 1 . .
H H11 0.517(5) 0.295(5) 0.3458(19) 0.057 Uiso d 1 . .
H H12 0.341(5) 0.371(6) 0.3245(18) 0.057 Uiso d 1 . .
C C2 0.4519(5) 0.2806(5) 0.23968(19) 0.0514(9) Uani d 1 . .
H H2A 0.3910 0.1588 0.2356 0.062 Uiso calc 1 . .
H H2B 0.5760 0.2611 0.2328 0.062 Uiso calc 1 . .
C C3 0.3538(5) 0.4111(4) 0.17851(18) 0.0454(8) Uani d 1 . .
H H3A 0.3539 0.3575 0.1283 0.055 Uiso calc 1 . .
H H3B 0.2280 0.4258 0.1839 0.055 Uiso calc 1 . .
N N4 0.4437(3) 0.5952(4) 0.18516(13) 0.0393(6) Uani d 1 . .
C C5 0.4369(5) 0.6791(5) 0.25945(16) 0.0441(8) Uani d 1 . .
H H5A 0.3106 0.6953 0.2639 0.053 Uiso calc 1 . .
H H5B 0.4941 0.8029 0.2633 0.053 Uiso calc 1 . .
C C6 0.5333(5) 0.5553(4) 0.32330(19) 0.0521(10) Uani d 1 . .
H H6A 0.6621 0.5488 0.3217 0.063 Uiso calc 1 . .
H H6B 0.5219 0.6093 0.3723 0.063 Uiso calc 1 . .
C C21 0.3879(5) 0.7242(5) 0.12346(16) 0.0416(8) Uani d 1 . .
C C22 0.5099(5) 0.8649(5) 0.11148(18) 0.0515(9) Uani d 1 . .
C C23 0.4638(6) 0.9900(6) 0.0511(2) 0.0665(11) Uani d 1 . .
H H23 0.5453 1.0842 0.0435 0.080 Uiso calc 1 . .
C C24 0.2984(7) 0.9750(7) 0.0025(2) 0.0749(13) Uani d 1 . .
H H24 0.2678 1.0590 -0.0383 0.090 Uiso calc 1 . .
C C25 0.1785(6) 0.8393(7) 0.0131(2) 0.0695(12) Uani d 1 . .
H H25 0.0662 0.8300 -0.0205 0.083 Uiso calc 1 . .
C C26 0.2227(5) 0.7140(6) 0.07395(18) 0.0546(9) Uani d 1 . .
H H26 0.1390 0.6219 0.0812 0.066 Uiso calc 1 . .
O O22 0.6727(4) 0.8666(4) 0.16178(15) 0.0723(8) Uani d 1 . .
C C27 0.8158(6) 0.9858(8) 0.1471(3) 0.0936(15) Uani d 1 . .
H H27A 0.9212 0.9712 0.1875 0.140 Uiso calc 1 . .
H H27B 0.8463 0.9511 0.0990 0.140 Uiso calc 1 . .
H H27C 0.7762 1.1153 0.1449 0.140 Uiso calc 1 . .
C C31 0.8601(4) 0.0130(4) 0.38558(16) 0.0321(7) Uani d 1 . .
O O31 0.8264(3) 0.1842(3) 0.36938(12) 0.0422(5) Uani d 1 . .
O O32 0.7484(3) -0.1056(3) 0.39964(13) 0.0484(6) Uani d 1 . .
C C32 1.0532(4) -0.0580(4) 0.38922(16) 0.0300(7) Uani d 1 . .
H H32A 1.0927 -0.0187 0.3423 0.036 Uiso calc 1 . .
O O33 1.0645(3) -0.2564(3) 0.39473(13) 0.0431(6) Uani d 1 . .
H H33 0.985(5) -0.285(6) 0.414(2) 0.065 Uiso d 1 . .
C C33 1.1809(3) 0.0309(4) 0.45784(14) 0.0292(7) Uani d 1 . .
H H33A 1.1800 0.1684 0.4506 0.035 Uiso calc 1 . .
O O34 1.1191(3) -0.0087(3) 0.52580(11) 0.0405(5) Uani d 1 . .
H H34 1.162(5) -0.109(6) 0.544(2) 0.061 Uiso d 1 . .
C C34 1.3725(4) -0.0400(4) 0.46138(16) 0.0307(7) Uani d 1 . .
O O35 1.4553(3) -0.1271(3) 0.51524(11) 0.0479(6) Uani d 1 . .
O O36 1.4319(3) -0.0004(3) 0.39858(11) 0.0351(5) Uani d 1 . .
H H36 1.537(5) -0.036(6) 0.4062(17) 0.053 Uiso d 1 . .
O O41 0.0854(4) 0.4055(4) 0.31999(16) 0.0612(8) Uani d 1 . .
H H41 0.068(6) 0.512(7) 0.336(2) 0.092 Uiso d 1 . .
H H42 -0.004(6) 0.335(7) 0.329(2) 0.092 Uiso d 1 . .
O O51 -0.1304(7) 0.4856(9) 0.1775(2) 0.104(2) Uani d 0.698(9) . .
H H51 -0.051(9) 0.470(13) 0.228(2) 0.157 Uiso d 0.698(9) . .
H H52 -0.225(8) 0.573(10) 0.185(4) 0.157 Uiso d 0.698(9) . .
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 . . 111.9(3) ?
C2 N1 H11 . . 106(2) ?
C6 N1 H11 . . 109(3) ?
C2 N1 H12 . . 110(2) ?
C6 N1 H12 . . 107(3) ?
H11 N1 H12 . . 112(4) ?
N1 C2 C3 . . 109.9(3) ?
N1 C2 H2A . . 109.7 ?
C3 C2 H2A . . 109.7 ?
N1 C2 H2B . . 109.7 ?
C3 C2 H2B . . 109.7 ?
H2A C2 H2B . . 108.2 ?
N4 C3 C2 . . 109.8(3) ?
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 . . 116.7(2) ?
C21 N4 C5 . . 112.4(2) ?
C3 N4 C5 . . 109.7(2) ?
N4 C5 C6 . . 110.5(3) ?
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 . . 110.4(3) ?
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 . . 118.2(3) ?
C26 C21 N4 . . 123.4(3) ?
C22 C21 N4 . . 118.3(3) ?
O22 C22 C23 . . 123.9(4) ?
O22 C22 C21 . . 115.7(3) ?
C23 C22 C21 . . 120.5(3) ?
C24 C23 C22 . . 119.7(4) ?
C24 C23 H23 . . 120.1 ?
C22 C23 H23 . . 120.1 ?
C25 C24 C23 . . 120.7(4) ?
C25 C24 H24 . . 119.7 ?
C23 C24 H24 . . 119.7 ?
C24 C25 C26 . . 120.0(4) ?
C24 C25 H25 . . 120.0 ?
C26 C25 H25 . . 120.0 ?
C21 C26 C25 . . 120.9(4) ?
C21 C26 H26 . . 119.6 ?
C25 C26 H26 . . 119.6 ?
C22 O22 C27 . . 119.4(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 ?
O32 C31 O31 . . 125.6(3) ?
O32 C31 C32 . . 116.1(2) ?
O31 C31 C32 . . 118.2(3) ?
O33 C32 C31 . . 112.1(2) ?
O33 C32 C33 . . 109.6(2) ?
C31 C32 C33 . . 109.6(2) ?
O33 C32 H32A . . 108.5 ?
C31 C32 H32A . . 108.5 ?
C33 C32 H32A . . 108.5 ?
C32 O33 H33 . . 105(3) ?
O34 C33 C34 . . 111.8(2) ?
O34 C33 C32 . . 110.2(2) ?
C34 C33 C32 . . 109.5(2) ?
O34 C33 H33A . . 108.4 ?
C34 C33 H33A . . 108.4 ?
C32 C33 H33A . . 108.4 ?
C33 O34 H34 . . 110(3) ?
O35 C34 O36 . . 125.5(3) ?
O35 C34 C33 . . 122.5(3) ?
O36 C34 C33 . . 112.0(2) ?
C34 O36 H36 . . 106(2) ?
H41 O41 H42 . . 106(4) ?
H51 O51 H52 . . 106(3) ?
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 . 1.473(4) ?
N1 C6 . 1.479(4) ?
N1 H11 . 0.79(4) ?
N1 H12 . 0.90(4) ?
C2 C3 . 1.500(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 N4 . 1.458(4) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
N4 C21 . 1.423(4) ?
N4 C5 . 1.458(4) ?
C5 C6 . 1.499(4) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C21 C26 . 1.368(4) ?
C21 C22 . 1.394(5) ?
C22 O22 . 1.359(4) ?
C22 C23 . 1.381(5) ?
C23 C24 . 1.363(6) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.352(6) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.386(5) ?
C25 H25 . 0.9300 ?
C26 H26 . 0.9300 ?
O22 C27 . 1.427(5) ?
C27 H27A . 0.9600 ?
C27 H27B . 0.9600 ?
C27 H27C . 0.9600 ?
C31 O32 . 1.244(4) ?
C31 O31 . 1.257(4) ?
C31 C32 . 1.518(4) ?
C32 O33 . 1.406(3) ?
C32 C33 . 1.526(4) ?
C32 H32A . 0.9800 ?
O33 H33 . 0.78(4) ?
C33 O34 . 1.406(3) ?
C33 C34 . 1.508(4) ?
C33 H33A . 0.9800 ?
O34 H34 . 0.82(4) ?
C34 O35 . 1.201(3) ?
C34 O36 . 1.312(3) ?
O36 H36 . 0.81(3) ?
O41 H41 . 0.83(5) ?
O41 H42 . 0.88(5) ?
O51 H51 . 0.98(2) ?
O51 H52 . 0.97(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 . 0.79(4) 2.40(4) 3.028(4) 137(3) no
N1 H11 O36 1_455 0.79(4) 2.43(4) 2.977(4) 128(3) no
N1 H11 O35 2_756 0.79(4) 2.50(3) 2.942(3) 117(3) no
N1 H12 O41 . 0.89(4) 1.91(4) 2.792(5) 168(3) no
O33 H33 O34 2_746 0.77(4) 2.14(4) 2.800(3) 144(4) no
O34 H34 O31 2_746 0.82(4) 2.11(4) 2.836(3) 148(3) no
O36 H36 O32 1_655 0.81(4) 1.68(4) 2.478(3) 167(3) no
O41 H41 O33 1_465 0.82(5) 1.94(5) 2.753(4) 167(3) no
O41 H42 O31 1_455 0.87(5) 1.90(5) 2.766(4) 169(3) no
O51 H51 O41 . 0.98(4) 1.80(5) 2.776(5) 172(9) no
O51 H52 O22 1_455 0.97(7) 2.22(7) 3.054(7) 144(6) no
O51 H52 N4 1_455 0.97(7) 2.48(6) 3.307(6) 143(5) no
C23 H23 Cg2 2_655 0.93 2.91 3.722(4) 147 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 . . . . -54.9(4) ?
N1 C2 C3 N4 . . . . 58.6(4) ?
C2 C3 N4 C21 . . . . 169.1(3) ?
C2 C3 N4 C5 . . . . -61.7(3) ?
C21 N4 C5 C6 . . . . -167.9(3) ?
C3 N4 C5 C6 . . . . 60.6(3) ?
C2 N1 C6 C5 . . . . 53.7(4) ?
N4 C5 C6 N1 . . . . -56.1(4) ?
C3 N4 C21 C26 . . . . 22.6(4) ?
C5 N4 C21 C26 . . . . -105.3(3) ?
C3 N4 C21 C22 . . . . -155.5(3) ?
C5 N4 C21 C22 . . . . 76.6(3) ?
C26 C21 C22 O22 . . . . -179.1(3) ?
N4 C21 C22 O22 . . . . -0.9(4) ?
C26 C21 C22 C23 . . . . 0.0(5) ?
N4 C21 C22 C23 . . . . 178.2(3) ?
O22 C22 C23 C24 . . . . 178.6(4) ?
C21 C22 C23 C24 . . . . -0.4(5) ?
C22 C23 C24 C25 . . . . 0.3(6) ?
C23 C24 C25 C26 . . . . 0.3(6) ?
C22 C21 C26 C25 . . . . 0.6(5) ?
N4 C21 C26 C25 . . . . -177.5(3) ?
C24 C25 C26 C21 . . . . -0.7(6) ?
C23 C22 O22 C27 . . . . -8.7(6) ?
C21 C22 O22 C27 . . . . 170.4(4) ?
O32 C31 C32 O33 . . . . 10.6(4) ?
O31 C31 C32 O33 . . . . -169.8(2) ?
O32 C31 C32 C33 . . . . -111.3(3) ?
O31 C31 C32 C33 . . . . 68.3(3) ?
O33 C32 C33 O34 . . . . -66.8(3) ?
C31 C32 C33 O34 . . . . 56.6(3) ?
O33 C32 C33 C34 . . . . 56.6(3) ?
C31 C32 C33 C34 . . . . 179.9(2) ?
O34 C33 C34 O35 . . . . 3.2(4) ?
C32 C33 C34 O35 . . . . -119.2(3) ?
O34 C33 C34 O36 . . . . -178.9(3) ?
C32 C33 C34 O36 . . . . 58.7(3) ?

_cod_database_fobs_code 2243658
