#------------------------------------------------------------------------------
#$Date: 2016-02-19 23:18:51 +0100 (vie 19 de feb de 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/88/2018808.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_2018808
loop_
_publ_author_name
'Freire, Eleonora'
'Polla, Griselda'
'Baggio, Ricardo'
_publ_section_title
;
 Aripiprazole salts. III. Bis(aripiprazolium) oxalate--oxalic acid (1/1)
;
_journal_coeditor_code           YF3023
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              186
_journal_page_last               190
_journal_paper_doi               10.1107/S0108270113001133
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          '2C23 H28 Cl2 N3 O2 +, C2 O4 2-, C2 H2 O4'
_chemical_formula_moiety         '2(C23 H28 Cl2 N3 O2 +), C2 O4 2-, C2 H2 O4'
_chemical_formula_sum            'C50 H58 Cl4 N6 O12'
_chemical_formula_weight         1076.82
_chemical_name_systematic
;
Bis(4-(2,3-dichlorophenyl)-1-{4-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-
yl)oxy]butyl}piperazin-1-ium); oxalate; oxalic acid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.794(6)
_cell_angle_beta                 95.410(7)
_cell_angle_gamma                109.767(8)
_cell_formula_units_Z            1
_cell_length_a                   7.9609(7)
_cell_length_b                   11.2732(9)
_cell_length_c                   15.8323(11)
_cell_measurement_reflns_used    3032
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      29.12
_cell_measurement_theta_min      3.75
_cell_volume                     1288.2(2)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_device_type  'Oxford Diffraction Gemini CCD S Ultra'
_diffrn_measurement_method       'ω scans, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            16111
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.21
_diffrn_reflns_theta_min         3.71
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.228
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         6079
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0574
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0742P)²+0.0853P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1599
_reflns_number_gt                3903
_reflns_number_total             6079
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            yf3023.cif
_cod_data_source_block           I
_cod_database_code               2018808
_cod_database_fobs_code          2018808
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cl Cl1 0.24705(8) 0.54881(6) 0.79059(5) 0.0672(2) Uani d . 1 1
Cl Cl2 0.30443(12) 0.80669(8) 0.92693(5) 0.0900(3) Uani d . 1 1
O O1 0.7228(2) -0.50763(17) -0.01832(12) 0.0692(5) Uani d . 1 1
O O2 0.4837(2) -0.01643(16) 0.21786(11) 0.0608(5) Uani d . 1 1
N N1 0.6067(2) 0.33562(15) 0.59188(10) 0.0342(4) Uani d D 1 1
H H1N 0.687(2) 0.3920(18) 0.5745(14) 0.052(7) Uiso d D 1 1
N N2 0.5850(2) 0.51519(16) 0.74493(11) 0.0403(4) Uani d . 1 1
N N3 0.6600(3) -0.35294(19) 0.07242(13) 0.0512(5) Uani d D 1 1
H H3N 0.5451(16) -0.390(3) 0.0532(18) 0.082(9) Uiso d D 1 1
C C1 0.4556(3) 0.3858(2) 0.59495(13) 0.0406(5) Uani d . 1 1
H H1B 0.3560 0.3270 0.6146 0.049 Uiso calc R 1 1
H H1C 0.4118 0.3896 0.5366 0.049 Uiso calc R 1 1
C C2 0.5193(3) 0.51949(19) 0.65630(13) 0.0408(5) Uani d . 1 1
H H2A 0.6161 0.5791 0.6356 0.049 Uiso calc R 1 1
H H2B 0.4201 0.5511 0.6575 0.049 Uiso calc R 1 1
C C3 0.7385(3) 0.4717(2) 0.74336(14) 0.0485(5) Uani d . 1 1
H H3A 0.7836 0.4700 0.8020 0.058 Uiso calc R 1 1
H H3B 0.8359 0.5320 0.7234 0.058 Uiso calc R 1 1
C C4 0.6791(3) 0.3365(2) 0.68233(14) 0.0470(5) Uani d . 1 1
H H4A 0.7815 0.3084 0.6811 0.056 Uiso calc R 1 1
H H4B 0.5862 0.2756 0.7042 0.056 Uiso calc R 1 1
C C5 0.6137(3) 0.6317(2) 0.80828(14) 0.0435(5) Uani d . 1 1
C C6 0.4646(3) 0.6587(2) 0.83523(14) 0.0478(5) Uani d . 1 1
C C7 0.4896(4) 0.7729(2) 0.89606(15) 0.0570(6) Uani d . 1 1
C C8 0.6596(4) 0.8628(3) 0.93203(17) 0.0690(8) Uani d . 1 1
H H8 0.6752 0.9393 0.9731 0.083 Uiso calc R 1 1
C C9 0.8076(4) 0.8375(3) 0.90613(18) 0.0720(8) Uani d . 1 1
H H9 0.9239 0.8978 0.9299 0.086 Uiso calc R 1 1
C C10 0.7856(3) 0.7247(2) 0.84598(16) 0.0586(6) Uani d . 1 1
H H10 0.8875 0.7098 0.8299 0.070 Uiso calc R 1 1
C C11 0.5517(3) 0.20455(18) 0.52984(13) 0.0394(5) Uani d . 1 1
H H11A 0.4421 0.1461 0.5430 0.047 Uiso calc R 1 1
H H11B 0.6464 0.1698 0.5382 0.047 Uiso calc R 1 1
C C12 0.5183(3) 0.20936(19) 0.43575(13) 0.0441(5) Uani d . 1 1
H H12A 0.6125 0.2846 0.4268 0.053 Uiso calc R 1 1
H H12B 0.4029 0.2192 0.4229 0.053 Uiso calc R 1 1
C C13 0.5163(3) 0.0868(2) 0.37300(14) 0.0506(6) Uani d . 1 1
H H13A 0.6230 0.0689 0.3914 0.061 Uiso calc R 1 1
H H13B 0.4101 0.0133 0.3748 0.061 Uiso calc R 1 1
C C14 0.5133(4) 0.1022(2) 0.28102(15) 0.0548(6) Uani d . 1 1
H H14A 0.4181 0.1340 0.2664 0.066 Uiso calc R 1 1
H H14B 0.6279 0.1669 0.2779 0.066 Uiso calc R 1 1
C C15 0.6264(3) -0.0600(2) 0.20975(15) 0.0501(5) Uani d . 1 1
C C16 0.5807(3) -0.1784(2) 0.14990(14) 0.0472(5) Uani d . 1 1
H H16 0.4620 -0.2221 0.1200 0.057 Uiso calc R 1 1
C C17 0.7105(3) -0.2324(2) 0.13404(14) 0.0456(5) Uani d . 1 1
C C18 0.8883(3) -0.1695(2) 0.17826(16) 0.0543(6) Uani d . 1 1
C C19 0.9316(3) -0.0503(3) 0.23817(18) 0.0665(7) Uani d . 1 1
H H19 1.0497 -0.0068 0.2688 0.080 Uiso calc R 1 1
C C20 0.8014(4) 0.0060(3) 0.25359(17) 0.0635(7) Uani d . 1 1
H H20 0.8332 0.0868 0.2929 0.076 Uiso calc R 1 1
C C21 0.7780(3) -0.4032(2) 0.03771(16) 0.0545(6) Uani d . 1 1
C C22 0.9744(3) -0.3217(3) 0.06867(19) 0.0696(7) Uani d . 1 1
H H22A 1.0136 -0.2658 0.0296 0.083 Uiso calc R 1 1
H H22B 1.0429 -0.3787 0.0648 0.083 Uiso calc R 1 1
C C23 1.0195(3) -0.2375(3) 0.1617(2) 0.0714(8) Uani d . 1 1
H H23A 1.0163 -0.2914 0.2025 0.086 Uiso calc R 1 1
H H23B 1.1414 -0.1731 0.1719 0.086 Uiso calc R 1 1
C C1A 1.0303(3) 0.94180(19) 0.48760(16) 0.0439(5) Uani d . 1 1
O O1A 0.9369(2) 0.84251(14) 0.51231(14) 0.0642(5) Uani d D 1 1
H H1A 0.976(4) 0.779(2) 0.503(2) 0.099(11) Uiso d D 1 1
O O2A 1.1549(3) 0.94871(19) 0.45082(18) 0.0999(8) Uani d . 1 1
C C1B 0.9590(3) 0.55404(18) 0.50263(14) 0.0388(5) Uani d . 1 1
O O1B 1.0421(2) 0.64998(13) 0.47545(12) 0.0586(5) Uani d . 1 1
O O2B 0.8173(2) 0.53727(14) 0.53253(11) 0.0550(4) Uani d . 1 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_3
_geom_angle
C15 O2 C14 . 118.99(18)
C4 N1 C11 . 112.11(14)
C4 N1 C1 . 109.18(15)
C11 N1 C1 . 112.60(15)
C4 N1 H1N . 108.5(15)
C11 N1 H1N . 110.5(16)
C1 N1 H1N . 103.5(16)
C5 N2 C3 . 115.85(16)
C5 N2 C2 . 112.34(15)
C3 N2 C2 . 109.44(15)
C21 N3 C17 . 124.7(2)
C21 N3 H3N . 121(2)
C17 N3 H3N . 114(2)
N1 C1 C2 . 110.49(16)
N1 C1 H1B . 109.6
C2 C1 H1B . 109.6
N1 C1 H1C . 109.6
C2 C1 H1C . 109.6
H1B C1 H1C . 108.1
N2 C2 C1 . 110.14(15)
N2 C2 H2A . 109.6
C1 C2 H2A . 109.6
N2 C2 H2B . 109.6
C1 C2 H2B . 109.6
H2A C2 H2B . 108.1
N2 C3 C4 . 109.74(17)
N2 C3 H3A . 109.7
C4 C3 H3A . 109.7
N2 C3 H3B . 109.7
C4 C3 H3B . 109.7
H3A C3 H3B . 108.2
N1 C4 C3 . 110.95(16)
N1 C4 H4A . 109.4
C3 C4 H4A . 109.4
N1 C4 H4B . 109.4
C3 C4 H4B . 109.4
H4A C4 H4B . 108.0
C10 C5 C6 . 116.9(2)
C10 C5 N2 . 123.28(19)
C6 C5 N2 . 119.78(19)
C7 C6 C5 . 120.7(2)
C7 C6 Cl1 . 119.64(19)
C5 C6 Cl1 . 119.63(17)
C8 C7 C6 . 121.2(2)
C8 C7 Cl2 . 118.48(19)
C6 C7 Cl2 . 120.3(2)
C7 C8 C9 . 118.6(2)
C7 C8 H8 . 120.7
C9 C8 H8 . 120.7
C10 C9 C8 . 121.0(3)
C10 C9 H9 . 119.5
C8 C9 H9 . 119.5
C9 C10 C5 . 121.5(2)
C9 C10 H10 . 119.3
C5 C10 H10 . 119.3
N1 C11 C12 . 112.24(14)
N1 C11 H11A . 109.2
C12 C11 H11A . 109.2
N1 C11 H11B . 109.2
C12 C11 H11B . 109.2
H11A C11 H11B . 107.9
C11 C12 C13 . 111.76(16)
C11 C12 H12A . 109.3
C13 C12 H12A . 109.3
C11 C12 H12B . 109.3
C13 C12 H12B . 109.3
H12A C12 H12B . 107.9
C14 C13 C12 . 110.97(17)
C14 C13 H13A . 109.4
C12 C13 H13A . 109.4
C14 C13 H13B . 109.4
C12 C13 H13B . 109.4
H13A C13 H13B . 108.0
O2 C14 C13 . 112.98(18)
O2 C14 H14A . 109.0
C13 C14 H14A . 109.0
O2 C14 H14B . 109.0
C13 C14 H14B . 109.0
H14A C14 H14B . 107.8
C20 C15 C16 . 120.3(2)
C20 C15 O2 . 125.5(2)
C16 C15 O2 . 114.16(19)
C15 C16 C17 . 120.3(2)
C15 C16 H16 . 119.8
C17 C16 H16 . 119.8
C16 C17 C18 . 121.0(2)
C16 C17 N3 . 119.0(2)
C18 C17 N3 . 120.0(2)
C19 C18 C17 . 117.8(2)
C19 C18 C23 . 124.0(2)
C17 C18 C23 . 118.1(2)
C18 C19 C20 . 121.5(2)
C18 C19 H19 . 119.2
C20 C19 H19 . 119.2
C15 C20 C19 . 119.0(2)
C15 C20 H20 . 120.5
C19 C20 H20 . 120.5
O1 C21 N3 . 120.7(2)
O1 C21 C22 . 123.3(2)
N3 C21 C22 . 115.9(2)
C21 C22 C23 . 114.5(2)
C21 C22 H22A . 108.6
C23 C22 H22A . 108.6
C21 C22 H22B . 108.6
C23 C22 H22B . 108.6
H22A C22 H22B . 107.6
C18 C23 C22 . 111.5(2)
C18 C23 H23A . 109.3
C22 C23 H23A . 109.3
C18 C23 H23B . 109.3
C22 C23 H23B . 109.3
H23A C23 H23B . 108.0
O2A C1A O1A . 125.28(19)
O2A C1A C1A 2_776 121.3(2)
O1A C1A C1A 2_776 113.4(2)
C1A O1A H1A . 114(2)
O2B C1B O1B . 125.62(17)
O2B C1B C1B 2_766 117.6(2)
O1B C1B C1B 2_766 116.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cl1 C6 . 1.730(2)
Cl2 C7 . 1.731(3)
O1 C21 . 1.231(3)
O2 C15 . 1.388(3)
O2 C14 . 1.428(3)
N1 C4 . 1.489(3)
N1 C11 . 1.493(2)
N1 C1 . 1.493(2)
N1 H1N . 0.848(9)
N2 C5 . 1.414(3)
N2 C3 . 1.464(2)
N2 C2 . 1.467(2)
N3 C21 . 1.354(3)
N3 C17 . 1.405(3)
N3 H3N . 0.862(10)
C1 C2 . 1.504(3)
C1 H1B . 0.9700
C1 H1C . 0.9700
C2 H2A . 0.9700
C2 H2B . 0.9700
C3 C4 . 1.518(3)
C3 H3A . 0.9700
C3 H3B . 0.9700
C4 H4A . 0.9700
C4 H4B . 0.9700
C5 C10 . 1.395(3)
C5 C6 . 1.404(3)
C6 C7 . 1.381(3)
C7 C8 . 1.369(4)
C8 C9 . 1.381(4)
C8 H8 . 0.9300
C9 C10 . 1.370(3)
C9 H9 . 0.9300
C10 H10 . 0.9300
C11 C12 . 1.504(3)
C11 H11A . 0.9700
C11 H11B . 0.9700
C12 C13 . 1.522(3)
C12 H12A . 0.9700
C12 H12B . 0.9700
C13 C14 . 1.500(3)
C13 H13A . 0.9700
C13 H13B . 0.9700
C14 H14A . 0.9700
C14 H14B . 0.9700
C15 C20 . 1.372(3)
C15 C16 . 1.379(3)
C16 C17 . 1.383(3)
C16 H16 . 0.9300
C17 C18 . 1.388(3)
C18 C19 . 1.388(3)
C18 C23 . 1.503(3)
C19 C20 . 1.402(4)
C19 H19 . 0.9300
C20 H20 . 0.9300
C21 C22 . 1.493(3)
C22 C23 . 1.516(4)
C22 H22A . 0.9700
C22 H22B . 0.9700
C23 H23A . 0.9700
C23 H23B . 0.9700
C1A O2A . 1.186(3)
C1A O1A . 1.277(2)
C1A C1A 2_776 1.536(4)
O1A H1A . 0.858(10)
C1B O2B . 1.235(2)
C1B O1B . 1.246(2)
C1B C1B 2_766 1.557(4)
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
C2 H2B Cl1 . 0.97 2.62 3.224(2) 120.3
O1A H1A O1B . 0.858(10) 1.705(11) 2.561(2) 174(3)
N3 H3N O1 2_645 0.862(10) 2.009(11) 2.866(3) 173(3)
N1 H1N O2B . 0.848(9) 1.903(11) 2.730(2) 164(2)
C1 H1C O2B 2_666 0.97 2.49 3.272(2) 137.2
C2 H2A O2B . 0.97 2.48 3.197(3) 130.8
C11 H11B O2A 2_766 0.97 2.41 3.368(3) 171.2
C13 H13B O2A 1_445 0.97 2.43 3.262(3) 143.0
