#------------------------------------------------------------------------------
#$Date: 2020-03-06 08:26:34 +0200 (Fri, 06 Mar 2020) $
#$Revision: 249116 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/33/2243309.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_2243309
loop_
_publ_author_name
'Kiran Kumar, Haruvegowda'
'Yathirajan, Hemmige S.'
'Harish Chinthal, Chayanna'
'Foro, Sabine'
'Glidewell, Christopher'
_publ_section_title
;
 Crystal structures of the recreational drug
 N-(4-methoxyphenyl)piperazine (MeOPP) and three of its salts
;
_journal_coeditor_code           ZL2772
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              488
_journal_page_last               495
_journal_paper_doi               10.1107/S2056989020002844
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C11 H17 N2 O +, C7 H3 N2 O6 -'
_chemical_formula_moiety         'C11 H17 N2 O +, C7 H3 N2 O6 -'
_chemical_formula_sum            'C18 H20 N4 O7'
_chemical_formula_weight         404.38
_chemical_name_systematic
;
4-(4-Methoxyphenyl)piperazin-1-ium 3,5-dinitrobenzoate
;
_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     dual
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                92.238(4)
_cell_angle_beta                 97.057(4)
_cell_angle_gamma                108.618(5)
_cell_formula_units_Z            2
_cell_length_a                   7.4365(4)
_cell_length_b                   10.6276(6)
_cell_length_c                   13.2700(6)
_cell_measurement_reflns_used    4210
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.755
_cell_measurement_theta_min      2.655
_cell_volume                     982.92(9)
_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      293(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  0.0105
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7013
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_min         2.655
_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    0.107
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.480
_exptl_crystal_size_min          0.480
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0406
_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)+(0.0482P)²+0.2082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1097
_reflns_number_gt                3057
_reflns_number_total             4202
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zl2772sup1.cif
_cod_data_source_block           II
_cod_database_code               2243309
_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   0.948
_shelx_estimated_absorpt_t_max   0.950
_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 0.4909(2) 0.44996(14) 0.34081(10) 0.0521(3) Uani d 1 . .
H H11 0.578(3) 0.5249(19) 0.3837(14) 0.063 Uiso d 1 . .
H H12 0.464(3) 0.3711(18) 0.3776(14) 0.063 Uiso d 1 . .
C C2 0.3094(3) 0.47725(16) 0.31197(13) 0.0579(4) Uani d 1 . .
H H2A 0.2620 0.4993 0.3729 0.070 Uiso calc 1 . .
H H2B 0.2140 0.3982 0.2761 0.070 Uiso calc 1 . .
C C3 0.3399(3) 0.59140(16) 0.24455(12) 0.0518(4) Uani d 1 . .
H H3A 0.2191 0.6068 0.2249 0.062 Uiso calc 1 . .
H H3B 0.4290 0.6719 0.2819 0.062 Uiso calc 1 . .
N N4 0.41580(19) 0.56126(12) 0.15311(9) 0.0475(3) Uani d 1 . .
C C5 0.5974(3) 0.54000(17) 0.18174(12) 0.0532(4) Uani d 1 . .
H H5A 0.6890 0.6204 0.2180 0.064 Uiso calc 1 . .
H H5B 0.6473 0.5205 0.1209 0.064 Uiso calc 1 . .
C C6 0.5732(3) 0.42574(17) 0.24871(13) 0.0601(5) Uani d 1 . .
H H6A 0.4893 0.3441 0.2105 0.072 Uiso calc 1 . .
H H6B 0.6967 0.4147 0.2689 0.072 Uiso calc 1 . .
C C21 0.4128(2) 0.65236(14) 0.07691(11) 0.0443(3) Uani d 1 . .
C C22 0.2377(2) 0.65974(17) 0.03241(12) 0.0555(4) Uani d 1 . .
H H22 0.1256 0.6063 0.0536 0.067 Uiso calc 1 . .
C C23 0.2264(2) 0.74413(18) -0.04220(13) 0.0572(4) Uani d 1 . .
H H23 0.1074 0.7474 -0.0706 0.069 Uiso calc 1 . .
C C24 0.3915(2) 0.82446(16) -0.07540(11) 0.0468(4) Uani d 1 . .
C C25 0.5662(2) 0.81844(16) -0.03278(11) 0.0477(4) Uani d 1 . .
H H25 0.6779 0.8715 -0.0546 0.057 Uiso calc 1 . .
C C26 0.5764(2) 0.73326(16) 0.04294(11) 0.0477(4) Uani d 1 . .
H H26 0.6957 0.7305 0.0714 0.057 Uiso calc 1 . .
O O24 0.36537(16) 0.90394(12) -0.15109(9) 0.0609(3) Uani d 1 . .
C C27 0.5312(2) 0.98606(18) -0.18771(14) 0.0595(4) Uani d 1 . .
H H27A 0.4941 1.0364 -0.2401 0.089 Uiso calc 1 . .
H H27B 0.6143 1.0459 -0.1327 0.089 Uiso calc 1 . .
H H27C 0.5973 0.9314 -0.2151 0.089 Uiso calc 1 . .
C C31 0.75477(19) 0.90885(13) 0.44906(10) 0.0370(3) Uani d 1 . .
C C32 0.74671(19) 1.02627(13) 0.49332(11) 0.0379(3) Uani d 1 . .
H H32 0.6919 1.0266 0.5526 0.045 Uiso calc 1 . .
C C33 0.8211(2) 1.14339(13) 0.44845(11) 0.0397(3) Uani d 1 . .
C C34 0.9027(2) 1.14837(15) 0.36080(11) 0.0425(3) Uani d 1 . .
H H34 0.9502 1.2278 0.3310 0.051 Uiso calc 1 . .
C C35 0.91080(19) 1.03023(15) 0.31926(10) 0.0416(3) Uani d 1 . .
C C36 0.8395(2) 0.91119(14) 0.36128(11) 0.0413(3) Uani d 1 . .
H H36 0.8480 0.8331 0.3312 0.050 Uiso calc 1 . .
C C37 0.6792(2) 0.77976(14) 0.49869(12) 0.0442(3) Uani d 1 . .
O O31 0.70674(18) 0.67975(10) 0.46073(10) 0.0624(3) Uani d 1 . .
O O32 0.59993(18) 0.78544(11) 0.57568(10) 0.0617(3) Uani d 1 . .
N N33 0.8205(2) 1.26892(13) 0.49865(12) 0.0556(4) Uani d 1 . .
O O33 0.7947(3) 1.26858(14) 0.58726(12) 0.0877(5) Uani d 1 . .
O O34 0.8460(2) 1.36548(11) 0.44914(12) 0.0745(4) Uani d 1 . .
N N35 1.00278(19) 1.03268(17) 0.22712(11) 0.0575(4) Uani d 1 . .
O O35 0.9969(2) 0.92646(16) 0.18661(11) 0.0886(5) Uani d 1 . .
O O36 1.08186(19) 1.14064(15) 0.19653(10) 0.0723(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 . . 110.43(13) ?
C2 N1 H11 . . 108.2(11) ?
C6 N1 H11 . . 111.1(11) ?
C2 N1 H12 . . 108.4(11) ?
C6 N1 H12 . . 108.7(10) ?
H11 N1 H12 . . 110.0(15) ?
N1 C2 C3 . . 110.47(14) ?
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 . . 110.40(13) ?
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 . . 115.97(12) ?
C21 N4 C3 . . 113.26(12) ?
C5 N4 C3 . . 109.90(12) ?
N4 C5 C6 . . 110.50(14) ?
N4 C5 H5A . . 109.6 ?
C6 C5 H5A . . 109.6 ?
N4 C5 H5B . . 109.6 ?
C6 C5 H5B . . 109.6 ?
H5A C5 H5B . . 108.1 ?
N1 C6 C5 . . 111.08(13) ?
N1 C6 H6A . . 109.4 ?
C5 C6 H6A . . 109.4 ?
N1 C6 H6B . . 109.4 ?
C5 C6 H6B . . 109.4 ?
H6A C6 H6B . . 108.0 ?
C26 C21 C22 . . 117.42(14) ?
C26 C21 N4 . . 123.45(14) ?
C22 C21 N4 . . 119.12(14) ?
C23 C22 C21 . . 121.53(15) ?
C23 C22 H22 . . 119.2 ?
C21 C22 H22 . . 119.2 ?
C22 C23 C24 . . 120.35(15) ?
C22 C23 H23 . . 119.8 ?
C24 C23 H23 . . 119.8 ?
O24 C24 C25 . . 124.83(14) ?
O24 C24 C23 . . 116.04(14) ?
C25 C24 C23 . . 119.13(14) ?
C24 C25 C26 . . 120.16(14) ?
C24 C25 H25 . . 119.9 ?
C26 C25 H25 . . 119.9 ?
C21 C26 C25 . . 121.40(15) ?
C21 C26 H26 . . 119.3 ?
C25 C26 H26 . . 119.3 ?
C24 O24 C27 . . 117.47(13) ?
O24 C27 H27A . . 109.5 ?
O24 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
O24 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C32 C31 C36 . . 119.36(12) ?
C32 C31 C37 . . 120.07(13) ?
C36 C31 C37 . . 120.52(13) ?
C31 C32 C33 . . 119.18(13) ?
C31 C32 H32 . . 120.4 ?
C33 C32 H32 . . 120.4 ?
C34 C33 C32 . . 122.74(13) ?
C34 C33 N33 . . 118.33(13) ?
C32 C33 N33 . . 118.88(13) ?
C33 C34 C35 . . 116.73(13) ?
C33 C34 H34 . . 121.6 ?
C35 C34 H34 . . 121.6 ?
C34 C35 C36 . . 122.71(13) ?
C34 C35 N35 . . 118.15(13) ?
C36 C35 N35 . . 119.13(14) ?
C35 C36 C31 . . 119.26(13) ?
C35 C36 H36 . . 120.4 ?
C31 C36 H36 . . 120.4 ?
O31 C37 O32 . . 126.39(14) ?
O31 C37 C31 . . 117.10(14) ?
O32 C37 C31 . . 116.49(13) ?
O33 N33 O34 . . 124.64(15) ?
O33 N33 C33 . . 117.22(13) ?
O34 N33 C33 . . 118.14(15) ?
O35 N35 O36 . . 124.03(15) ?
O35 N35 C35 . . 117.67(15) ?
O36 N35 C35 . . 118.29(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 . 1.478(2) ?
N1 C6 . 1.481(2) ?
N1 H11 . 0.96(2) ?
N1 H12 . 0.965(18) ?
C2 C3 . 1.511(2) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 N4 . 1.4654(19) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
N4 C21 . 1.4301(18) ?
N4 C5 . 1.448(2) ?
C5 C6 . 1.510(2) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C21 C26 . 1.386(2) ?
C21 C22 . 1.389(2) ?
C22 C23 . 1.374(2) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.387(2) ?
C23 H23 . 0.9300 ?
C24 O24 . 1.3724(18) ?
C24 C25 . 1.373(2) ?
C25 C26 . 1.390(2) ?
C25 H25 . 0.9300 ?
C26 H26 . 0.9300 ?
O24 C27 . 1.4181(19) ?
C27 H27A . 0.9600 ?
C27 H27B . 0.9600 ?
C27 H27C . 0.9600 ?
C31 C32 . 1.3803(19) ?
C31 C36 . 1.388(2) ?
C31 C37 . 1.5169(19) ?
C32 C33 . 1.3817(19) ?
C32 H32 . 0.9300 ?
C33 C34 . 1.372(2) ?
C33 N33 . 1.4693(19) ?
C34 C35 . 1.374(2) ?
C34 H34 . 0.9300 ?
C35 C36 . 1.376(2) ?
C35 N35 . 1.4696(19) ?
C36 H36 . 0.9300 ?
C37 O31 . 1.2440(18) ?
C37 O32 . 1.2495(19) ?
N33 O33 . 1.2143(19) ?
N33 O34 . 1.2165(17) ?
N35 O35 . 1.2169(19) ?
N35 O36 . 1.2211(18) ?
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 . 0.96(2) 1.814(19) 2.7638(18) 169(2) no
N1 H12 O32 2_666 0.964(18) 1.740(18) 2.6953(18) 170.5(17) 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 . . . . -55.07(17) ?
N1 C2 C3 N4 . . . . 57.89(18) ?
C2 C3 N4 C21 . . . . 168.46(14) ?
C2 C3 N4 C5 . . . . -60.05(18) ?
C21 N4 C5 C6 . . . . -170.46(12) ?
C3 N4 C5 C6 . . . . 59.49(16) ?
C2 N1 C6 C5 . . . . 54.81(19) ?
N4 C5 C6 N1 . . . . -57.29(19) ?
C5 N4 C21 C26 . . . . -10.3(2) ?
C3 N4 C21 C26 . . . . 118.13(17) ?
C5 N4 C21 C22 . . . . 168.48(14) ?
C3 N4 C21 C22 . . . . -63.10(18) ?
C26 C21 C22 C23 . . . . -0.2(2) ?
N4 C21 C22 C23 . . . . -179.05(15) ?
C21 C22 C23 C24 . . . . 0.2(3) ?
C22 C23 C24 O24 . . . . 179.14(16) ?
C22 C23 C24 C25 . . . . 0.0(3) ?
O24 C24 C25 C26 . . . . -179.33(14) ?
C23 C24 C25 C26 . . . . -0.3(2) ?
C22 C21 C26 C25 . . . . -0.1(2) ?
N4 C21 C26 C25 . . . . 178.71(14) ?
C24 C25 C26 C21 . . . . 0.3(2) ?
C25 C24 O24 C27 . . . . -0.2(2) ?
C23 C24 O24 C27 . . . . -179.20(15) ?
C36 C31 C32 C33 . . . . 0.8(2) ?
C37 C31 C32 C33 . . . . 178.20(12) ?
C31 C32 C33 C34 . . . . 0.3(2) ?
C31 C32 C33 N33 . . . . -177.08(13) ?
C32 C33 C34 C35 . . . . -1.1(2) ?
N33 C33 C34 C35 . . . . 176.30(13) ?
C33 C34 C35 C36 . . . . 0.8(2) ?
C33 C34 C35 N35 . . . . -178.10(13) ?
C34 C35 C36 C31 . . . . 0.3(2) ?
N35 C35 C36 C31 . . . . 179.18(12) ?
C32 C31 C36 C35 . . . . -1.1(2) ?
C37 C31 C36 C35 . . . . -178.48(12) ?
C32 C31 C37 O31 . . . . -173.38(14) ?
C36 C31 C37 O31 . . . . 4.0(2) ?
C32 C31 C37 O32 . . . . 4.7(2) ?
C36 C31 C37 O32 . . . . -177.93(13) ?
C34 C33 N33 O33 . . . . -161.49(16) ?
C32 C33 N33 O33 . . . . 16.0(2) ?
C34 C33 N33 O34 . . . . 18.4(2) ?
C32 C33 N33 O34 . . . . -164.13(14) ?
C34 C35 N35 O35 . . . . -174.75(15) ?
C36 C35 N35 O35 . . . . 6.3(2) ?
C34 C35 N35 O36 . . . . 6.0(2) ?
C36 C35 N35 O36 . . . . -172.92(14) ?

_cod_database_fobs_code 2243309
