organic compounds
Flupentixol tartrate
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
*Correspondence e-mail: jjasinski@keene.edu
In the title salt, C23H26F3N2OS+·C4H5O6− [systematic name: 1-(2-hydroxyethyl)-4-[3-(2-(trifluoromethyl)thioxanthen-9-ylidene)propyl]piperazin-1-ium 3-carboxy-2,3-dihydroxypropionate], the monoprotonated piperazine ring in the cation adopts a chair conformation, while the thiopyran ring of the thioxanthene group has a boat conformation. The dihedral angle between the mean planes of the two outer aromatic rings of the thioxanthene groups is 31.6 (2)°. In the crystal, the cations and anions are linked via O—H⋯O, N—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds, forming chains propagating along [100]. In addition, R22(7), R22(11), R22(10) and R22(12) graph-set ring motifs involving the anions, and R22(9) graph-set ring motifs involving both the cations and anions are observed. The three F atoms of the trifluoromethyl group are disordered over two sets of sites and the individual atoms were refined with occupancy ratios of 0.54 (6):0.46 (6), 0.72 (2):0.28 (2) and 0.67 (3):0.33 (3).
CCDC reference: 982734
Related literature
For general background and the pharmacological properties of flupentixol, see: Robertson & Trimble (1981); Valle-Jones & Swarbrick (1981). For related structures, see: Jones et al. (1977); Post et al. (1975a,b); Siddegowda et al. (2011a,b). For standard bond lengths, see: Allen et al. (1987). For puckering parameters, see: Cremer & Pople (1975).
Experimental
Crystal data
|
Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2.
Supporting information
CCDC reference: 982734
10.1107/S1600536814001536/su2691sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001536/su2691Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001536/su2691Isup3.cml
A gift sample of flupentixol was donated by R. L. Fine Chemicals. The title salt was prepared by mixing flupentixol (0.2 g, 4.602 mmol) and tartaric acid (0.07 g, 4.602 mmol) dissolved in 5 mL of dimethyl formamide. The mixture was stirred at 320 K for 30 minutes. X-ray quality colourless block-like crystals were obtained on slow evaporation of the reaction mixture (M.p: 468-474 K).
The NH H atom was located in a difference Fourier map and freely refined. All of the other H atoms were placed in calculated positions and treated as riding atoms: O-H = 0.82 Å, C-H = 0.93, 0.97 and 0.98 Å for CH, methylene and methine H atoms, respectively, with Uiso(H) = 1.5Ueq(O), and = 1.2Ueq(C) for other H atoms. Disorder of the three F atoms of the trifluoromethyl group was modeled over two sets of sites: atoms F1A/F1AB, F2A/F2AB and F3A/F3AB with occupancy ratios of 0.54 (6):0.46 (6), 0.72 (2):0.28 (2) and 0.67 (3):0.33 (3), respectively. 6 reflections with were omitted in the final cycles of refinement.
Flupentixol [systematic name: 2-[4-[3-[(EZ)-2-(trifluoromethyl)-9H- thioxanthen-9-ylidene] propyl]piperazin-1-yl]ethanol is a well documented antipsychotic drug of the thioxanthene class. In addition to pure drug preparations, it is also available as deanxit, a combination product containing both melitracen and flupentixol. Low-dose neuroleptics have been applied increasingly in recent years to treat anxiety and depression (Robertson & Trimble, 1981; Valle-Jones & Swarbrick, 1981). The crystal structures of α-flupentixol (Post et al., 1975b), β-flupentixol (Post et al., 1975a), piflutixol (Jones et al., 1977) have been reported. The crystal structures of he dihydrochloride and difumarate salt of flupentixol has been reported by our group (Siddegowda et al., 2011a,b). In view of the importance of flupentixol, we prepared the tartrate salt of flupentixol and report herein on its crystal structure.
The title salt, Fig. 1, crystallizes with one independent monocation (A) and monoanion (B) in the θ, and φ = 0.578 (3) Å, 174.4 (3)° and 192 (3)°, respectively; (S1A/C16A/C11A/C10A/C22A/C17A) Q, θ, and φ = 0.486 (4) Å, 90.7 (5)° and 2.0 (5)°, respectively. The dihedral angle between the mean planes of the two outer aromatic rings of the thioxanthene groups is 31.6 (2)°.
Bond lengths are in normal ranges (Allen et al., 1987). The monoprotonated piperazine ring in A adopts a slightly disordered chair conformation while the thiopyran ring of the thioxanthene group has a boat conformation. The puckering parameters (Cremer & Pople, 1975) for the various rings are: (N1A//N2A/C1A-C4A) Q,In the crystal, the cations and anions are linked via O-H···O, N-H···O, O-H···N and C-H···O hydrogen bonds (Fig. 1), forming one-dimensional chains propagating along [1 0 0] (see Table 1 and Fig. 2). In addition, R22(7), R22(11), R22(10) and R22(12) graph set ring motifs involving the anions (Fig. 3) and R22(9) graph set ring motifs involving both the cations and anions (Fig. 2) are observed.
For general background and the pharmacological properties of flupentixol, see: Robertson & Trimble (1981); Valle-Jones & Swarbrick (1981). For related structures, see: Jones et al. (1977); Post et al. (1975a,b); Siddegowda et al. (2011a,b). For standard bond lengths, see: Allen et al. (1987). For puckering parameters, see: Cremer & Pople (1975).
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).Fig. 1. A view of the molecular structure of the title salt, with atom labelling. The displacement ellipsoids are drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines (see Table 1 for details). | |
Fig. 2. A view along the b axis of the crystal packing of the title compound showing the R22(9) graph set ring motifs involving cations and anions. The hydrogen bonds are shown as dashed lines (see Table 1 for details; H atoms not involved in hydrogen bonding have been omitted for clarity). | |
Fig. 3. A view along the a axis of the crystal packing of the title compound showing the R22(7), R22(11), R22(10) and R22(12) graph set ring motifs involving the anions. The hydrogen bonds are shown as dashed lines (see Table 1 for details; H atoms not involved in hydrogen bonding have been omitted for clarity). |
C23H26F3N2OS+·C4H5O6− | F(000) = 1224 |
Mr = 584.60 | Dx = 1.427 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 9.9239 (3) Å | Cell parameters from 5128 reflections |
b = 9.1968 (3) Å | θ = 3.0–72.5° |
c = 30.0099 (8) Å | µ = 1.67 mm−1 |
β = 96.617 (3)° | T = 173 K |
V = 2720.68 (13) Å3 | Block, colourless |
Z = 4 | 0.26 × 0.14 × 0.08 mm |
Agilent Gemini EOS diffractometer | 5325 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 4331 reflections with I > 2σ(I) |
Detector resolution: 16.0416 pixels mm-1 | Rint = 0.036 |
ω scans | θmax = 72.6°, θmin = 3.0° |
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012). | h = −11→12 |
Tmin = 0.871, Tmax = 1.000 | k = −11→11 |
16827 measured reflections | l = −37→25 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.078 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.206 | w = 1/[σ2(Fo2) + (0.0775P)2 + 5.4936P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
5325 reflections | Δρmax = 0.66 e Å−3 |
399 parameters | Δρmin = −0.71 e Å−3 |
0 restraints |
C23H26F3N2OS+·C4H5O6− | V = 2720.68 (13) Å3 |
Mr = 584.60 | Z = 4 |
Monoclinic, P21/n | Cu Kα radiation |
a = 9.9239 (3) Å | µ = 1.67 mm−1 |
b = 9.1968 (3) Å | T = 173 K |
c = 30.0099 (8) Å | 0.26 × 0.14 × 0.08 mm |
β = 96.617 (3)° |
Agilent Gemini EOS diffractometer | 5325 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012). | 4331 reflections with I > 2σ(I) |
Tmin = 0.871, Tmax = 1.000 | Rint = 0.036 |
16827 measured reflections |
R[F2 > 2σ(F2)] = 0.078 | 0 restraints |
wR(F2) = 0.206 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.66 e Å−3 |
5325 reflections | Δρmin = −0.71 e Å−3 |
399 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1A | 0.22263 (14) | 0.19267 (13) | 0.15278 (4) | 0.0582 (3) | |
F1A | 0.7407 (15) | 0.0331 (16) | 0.3035 (8) | 0.097 (7) | 0.54 (6) |
F1AB | 0.758 (2) | −0.042 (12) | 0.2900 (16) | 0.21 (2) | 0.46 (6) |
F2A | 0.5941 (6) | −0.0768 (15) | 0.3334 (2) | 0.095 (4) | 0.72 (2) |
F2AB | 0.676 (7) | 0.033 (5) | 0.3316 (9) | 0.23 (3) | 0.28 (2) |
F3A | 0.6844 (14) | −0.1770 (13) | 0.2809 (4) | 0.128 (6) | 0.67 (3) |
F3AB | 0.624 (4) | −0.182 (4) | 0.3087 (18) | 0.23 (3) | 0.33 (3) |
O1A | 0.0148 (2) | 0.2962 (3) | 0.58260 (9) | 0.0404 (6) | |
H1A | −0.0533 | 0.2684 | 0.5668 | 0.061* | |
N1A | 0.1313 (3) | 0.2330 (3) | 0.39016 (9) | 0.0307 (6) | |
N2A | 0.1121 (3) | 0.2869 (3) | 0.48473 (9) | 0.0265 (6) | |
H2A | 0.015 (4) | 0.289 (4) | 0.4845 (12) | 0.036 (10)* | |
C1A | 0.0891 (3) | 0.3761 (4) | 0.40584 (11) | 0.0306 (7) | |
H1AA | −0.0090 | 0.3796 | 0.4045 | 0.037* | |
H1AB | 0.1177 | 0.4519 | 0.3865 | 0.037* | |
C2A | 0.1518 (3) | 0.4018 (4) | 0.45352 (11) | 0.0309 (7) | |
H2AA | 0.2498 | 0.4033 | 0.4544 | 0.037* | |
H2AB | 0.1232 | 0.4960 | 0.4635 | 0.037* | |
C3A | 0.1422 (3) | 0.1394 (4) | 0.46724 (11) | 0.0298 (7) | |
H3AA | 0.1058 | 0.0658 | 0.4857 | 0.036* | |
H3AB | 0.2396 | 0.1260 | 0.4693 | 0.036* | |
C4A | 0.0820 (3) | 0.1199 (4) | 0.41933 (12) | 0.0321 (7) | |
H4AA | 0.1063 | 0.0247 | 0.4088 | 0.039* | |
H4AB | −0.0161 | 0.1248 | 0.4175 | 0.039* | |
C5A | 0.1858 (3) | 0.3134 (4) | 0.53071 (11) | 0.0319 (7) | |
H5AA | 0.1816 | 0.4164 | 0.5373 | 0.038* | |
H5AB | 0.2805 | 0.2882 | 0.5303 | 0.038* | |
C6A | 0.1307 (3) | 0.2288 (4) | 0.56834 (12) | 0.0339 (8) | |
H6AA | 0.1073 | 0.1311 | 0.5580 | 0.041* | |
H6AB | 0.2008 | 0.2213 | 0.5936 | 0.041* | |
C7A | 0.0795 (4) | 0.2111 (4) | 0.34276 (12) | 0.0389 (8) | |
H7AA | 0.0832 | 0.3022 | 0.3267 | 0.047* | |
H7AB | −0.0145 | 0.1801 | 0.3405 | 0.047* | |
C8A | 0.1644 (4) | 0.0949 (5) | 0.32109 (14) | 0.0486 (10) | |
H8AA | 0.2542 | 0.1330 | 0.3183 | 0.058* | |
H8AB | 0.1744 | 0.0092 | 0.3400 | 0.058* | |
C9A | 0.0966 (4) | 0.0553 (5) | 0.27644 (14) | 0.0471 (10) | |
H9A | 0.0035 | 0.0405 | 0.2749 | 0.057* | |
C10A | 0.1497 (4) | 0.0376 (4) | 0.23774 (14) | 0.0458 (9) | |
C11A | 0.2971 (4) | 0.0496 (4) | 0.23310 (13) | 0.0431 (9) | |
C12A | 0.3973 (4) | −0.0074 (4) | 0.26503 (14) | 0.0434 (9) | |
H12A | 0.3719 | −0.0572 | 0.2897 | 0.052* | |
C13A | 0.5340 (5) | 0.0093 (5) | 0.26043 (15) | 0.0508 (10) | |
C14A | 0.5736 (5) | 0.0809 (5) | 0.22360 (16) | 0.0565 (12) | |
H14A | 0.6652 | 0.0898 | 0.2201 | 0.068* | |
C15A | 0.4755 (5) | 0.1393 (5) | 0.19180 (14) | 0.0547 (11) | |
H15A | 0.5020 | 0.1916 | 0.1677 | 0.066* | |
C16A | 0.3389 (5) | 0.1206 (4) | 0.19556 (14) | 0.0482 (10) | |
C17A | 0.0773 (5) | 0.0805 (5) | 0.15652 (15) | 0.0533 (11) | |
C18A | −0.0161 (6) | 0.0691 (6) | 0.11939 (16) | 0.0668 (14) | |
H18A | −0.0022 | 0.1189 | 0.0934 | 0.080* | |
C19A | −0.1312 (5) | −0.0157 (6) | 0.12010 (18) | 0.0630 (13) | |
H19A | −0.1958 | −0.0211 | 0.0951 | 0.076* | |
C20A | −0.1479 (5) | −0.0926 (6) | 0.15899 (17) | 0.0633 (13) | |
H20A | −0.2229 | −0.1529 | 0.1596 | 0.076* | |
C21A | −0.0565 (5) | −0.0809 (5) | 0.19603 (16) | 0.0550 (11) | |
H21A | −0.0698 | −0.1337 | 0.2216 | 0.066* | |
C22A | 0.0591 (4) | 0.0105 (5) | 0.19664 (14) | 0.0472 (10) | |
C23A | 0.6367 (5) | −0.0546 (6) | 0.2954 (2) | 0.0642 (13) | |
O1B | 0.7933 (3) | 0.2013 (3) | 0.53327 (9) | 0.0420 (6) | |
O2B | 0.8419 (2) | 0.3109 (3) | 0.47059 (8) | 0.0353 (6) | |
O3B | 0.5331 (2) | 0.1935 (3) | 0.50950 (8) | 0.0350 (6) | |
H3B | 0.5829 | 0.1594 | 0.5306 | 0.052* | |
O4B | 0.6567 (2) | −0.0008 (3) | 0.44961 (9) | 0.0382 (6) | |
H4B | 0.5999 | −0.0500 | 0.4605 | 0.057* | |
O5B | 0.3929 (2) | 0.0037 (3) | 0.41614 (9) | 0.0374 (6) | |
O6B | 0.3977 (2) | 0.2427 (3) | 0.40286 (9) | 0.0384 (6) | |
H6B | 0.3165 | 0.2310 | 0.3950 | 0.058* | |
C1B | 0.7628 (3) | 0.2518 (4) | 0.49518 (12) | 0.0301 (7) | |
C2B | 0.6127 (3) | 0.2418 (4) | 0.47601 (11) | 0.0301 (7) | |
H2B | 0.5809 | 0.3379 | 0.4653 | 0.036* | |
C3B | 0.6004 (3) | 0.1351 (4) | 0.43639 (12) | 0.0321 (7) | |
H3BA | 0.6511 | 0.1749 | 0.4130 | 0.038* | |
C4B | 0.4522 (3) | 0.1186 (4) | 0.41685 (11) | 0.0298 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0820 (8) | 0.0475 (6) | 0.0469 (6) | 0.0068 (6) | 0.0150 (6) | 0.0075 (5) |
F1A | 0.042 (6) | 0.115 (11) | 0.126 (12) | −0.029 (5) | −0.030 (7) | 0.029 (7) |
F1AB | 0.073 (8) | 0.39 (6) | 0.153 (19) | 0.00 (2) | 0.024 (11) | 0.11 (3) |
F2A | 0.044 (3) | 0.173 (10) | 0.069 (4) | 0.013 (4) | 0.004 (2) | 0.046 (5) |
F2AB | 0.40 (7) | 0.18 (3) | 0.077 (15) | 0.12 (4) | −0.04 (3) | −0.069 (18) |
F3A | 0.129 (10) | 0.099 (8) | 0.146 (8) | 0.077 (7) | −0.023 (6) | −0.013 (5) |
F3AB | 0.15 (2) | 0.19 (3) | 0.32 (5) | −0.12 (2) | −0.10 (3) | 0.19 (3) |
O1A | 0.0287 (12) | 0.0545 (16) | 0.0379 (14) | 0.0055 (12) | 0.0034 (10) | −0.0116 (12) |
N1A | 0.0282 (14) | 0.0325 (15) | 0.0319 (15) | 0.0036 (11) | 0.0057 (11) | −0.0002 (12) |
N2A | 0.0212 (13) | 0.0293 (14) | 0.0296 (14) | 0.0016 (11) | 0.0049 (11) | −0.0001 (11) |
C1A | 0.0266 (16) | 0.0294 (17) | 0.0361 (18) | 0.0044 (13) | 0.0049 (14) | 0.0042 (14) |
C2A | 0.0289 (16) | 0.0277 (16) | 0.0360 (18) | −0.0007 (13) | 0.0031 (14) | 0.0017 (13) |
C3A | 0.0275 (16) | 0.0265 (16) | 0.0360 (18) | 0.0035 (13) | 0.0068 (14) | 0.0004 (13) |
C4A | 0.0299 (17) | 0.0294 (17) | 0.0379 (19) | 0.0004 (14) | 0.0076 (14) | −0.0028 (14) |
C5A | 0.0258 (16) | 0.0356 (18) | 0.0328 (18) | 0.0039 (14) | −0.0026 (13) | −0.0028 (14) |
C6A | 0.0267 (16) | 0.0407 (19) | 0.0336 (18) | 0.0070 (14) | 0.0002 (14) | 0.0012 (15) |
C7A | 0.0389 (19) | 0.046 (2) | 0.0319 (19) | −0.0005 (16) | 0.0038 (15) | −0.0006 (16) |
C8A | 0.036 (2) | 0.062 (3) | 0.046 (2) | 0.0048 (19) | 0.0005 (17) | −0.001 (2) |
C9A | 0.037 (2) | 0.060 (3) | 0.045 (2) | 0.0037 (19) | 0.0045 (17) | −0.0053 (19) |
C10A | 0.049 (2) | 0.042 (2) | 0.047 (2) | 0.0075 (18) | 0.0093 (19) | 0.0000 (17) |
C11A | 0.055 (2) | 0.038 (2) | 0.038 (2) | −0.0011 (18) | 0.0142 (18) | −0.0053 (16) |
C12A | 0.048 (2) | 0.044 (2) | 0.041 (2) | 0.0052 (18) | 0.0178 (18) | −0.0004 (17) |
C13A | 0.050 (2) | 0.050 (2) | 0.054 (3) | −0.0012 (19) | 0.013 (2) | −0.010 (2) |
C14A | 0.058 (3) | 0.052 (3) | 0.065 (3) | −0.016 (2) | 0.028 (2) | −0.013 (2) |
C15A | 0.066 (3) | 0.062 (3) | 0.038 (2) | −0.020 (2) | 0.016 (2) | 0.008 (2) |
C16A | 0.070 (3) | 0.036 (2) | 0.041 (2) | −0.0008 (19) | 0.017 (2) | −0.0062 (17) |
C17A | 0.068 (3) | 0.043 (2) | 0.050 (2) | 0.022 (2) | 0.010 (2) | −0.0046 (19) |
C18A | 0.092 (4) | 0.058 (3) | 0.048 (3) | 0.030 (3) | 0.000 (3) | −0.003 (2) |
C19A | 0.055 (3) | 0.057 (3) | 0.072 (3) | 0.016 (2) | −0.012 (2) | −0.010 (2) |
C20A | 0.050 (3) | 0.073 (3) | 0.063 (3) | 0.010 (2) | −0.013 (2) | −0.018 (3) |
C21A | 0.052 (3) | 0.052 (3) | 0.060 (3) | 0.005 (2) | 0.007 (2) | −0.004 (2) |
C22A | 0.050 (2) | 0.046 (2) | 0.046 (2) | 0.0109 (19) | 0.0073 (19) | −0.0062 (18) |
C23A | 0.041 (2) | 0.073 (3) | 0.081 (4) | 0.002 (2) | 0.013 (2) | −0.002 (3) |
O1B | 0.0320 (13) | 0.0488 (15) | 0.0436 (15) | −0.0057 (11) | −0.0028 (11) | 0.0103 (12) |
O2B | 0.0216 (11) | 0.0418 (14) | 0.0427 (14) | −0.0011 (10) | 0.0039 (10) | 0.0017 (11) |
O3B | 0.0229 (11) | 0.0455 (14) | 0.0373 (14) | 0.0031 (10) | 0.0068 (10) | 0.0041 (11) |
O4B | 0.0249 (11) | 0.0362 (13) | 0.0528 (16) | 0.0069 (10) | 0.0020 (11) | −0.0016 (11) |
O5B | 0.0263 (12) | 0.0380 (14) | 0.0467 (15) | 0.0008 (10) | −0.0003 (10) | 0.0023 (11) |
O6B | 0.0220 (11) | 0.0409 (14) | 0.0513 (16) | 0.0007 (10) | 0.0004 (11) | 0.0106 (12) |
C1B | 0.0237 (15) | 0.0280 (16) | 0.0383 (19) | 0.0008 (13) | 0.0019 (14) | −0.0033 (14) |
C2B | 0.0209 (15) | 0.0321 (17) | 0.0378 (19) | 0.0022 (13) | 0.0051 (13) | 0.0035 (14) |
C3B | 0.0200 (15) | 0.0375 (18) | 0.0388 (19) | 0.0031 (13) | 0.0039 (13) | 0.0013 (15) |
C4B | 0.0224 (15) | 0.0373 (18) | 0.0304 (17) | 0.0037 (14) | 0.0058 (13) | 0.0037 (14) |
S1A—C16A | 1.754 (5) | C9A—H9A | 0.9300 |
S1A—C17A | 1.788 (5) | C9A—C10A | 1.340 (6) |
F1A—C23A | 1.311 (12) | C10A—C11A | 1.489 (6) |
F1AB—F2AB | 1.71 (8) | C10A—C22A | 1.461 (6) |
F1AB—C23A | 1.24 (2) | C11A—C12A | 1.401 (6) |
F2A—C23A | 1.278 (8) | C11A—C16A | 1.406 (6) |
F2AB—C23A | 1.37 (3) | C12A—H12A | 0.9300 |
F3A—C23A | 1.314 (8) | C12A—C13A | 1.387 (6) |
F3AB—C23A | 1.25 (2) | C13A—C14A | 1.382 (6) |
O1A—H1A | 0.8200 | C13A—C23A | 1.497 (7) |
O1A—C6A | 1.415 (4) | C14A—H14A | 0.9300 |
N1A—C1A | 1.474 (4) | C14A—C15A | 1.391 (7) |
N1A—C4A | 1.479 (4) | C15A—H15A | 0.9300 |
N1A—C7A | 1.470 (4) | C15A—C16A | 1.384 (6) |
N2A—H2A | 0.96 (4) | C17A—C18A | 1.369 (7) |
N2A—C2A | 1.495 (4) | C17A—C22A | 1.395 (6) |
N2A—C3A | 1.497 (4) | C18A—H18A | 0.9300 |
N2A—C5A | 1.505 (4) | C18A—C19A | 1.385 (8) |
C1A—H1AA | 0.9700 | C19A—H19A | 0.9300 |
C1A—H1AB | 0.9700 | C19A—C20A | 1.391 (8) |
C1A—C2A | 1.512 (5) | C20A—H20A | 0.9300 |
C2A—H2AA | 0.9700 | C20A—C21A | 1.356 (6) |
C2A—H2AB | 0.9700 | C21A—H21A | 0.9300 |
C3A—H3AA | 0.9700 | C21A—C22A | 1.421 (6) |
C3A—H3AB | 0.9700 | O1B—C1B | 1.239 (4) |
C3A—C4A | 1.503 (5) | O2B—C1B | 1.261 (4) |
C4A—H4AA | 0.9700 | O3B—H3B | 0.8200 |
C4A—H4AB | 0.9700 | O3B—C2B | 1.419 (4) |
C5A—H5AA | 0.9700 | O4B—H4B | 0.8200 |
C5A—H5AB | 0.9700 | O4B—C3B | 1.407 (4) |
C5A—C6A | 1.524 (5) | O5B—C4B | 1.208 (4) |
C6A—H6AA | 0.9700 | O6B—H6B | 0.8200 |
C6A—H6AB | 0.9700 | O6B—C4B | 1.312 (4) |
C7A—H7AA | 0.9700 | C1B—C2B | 1.537 (4) |
C7A—H7AB | 0.9700 | C2B—H2B | 0.9800 |
C7A—C8A | 1.549 (6) | C2B—C3B | 1.535 (5) |
C8A—H8AA | 0.9700 | C3B—H3BA | 0.9800 |
C8A—H8AB | 0.9700 | C3B—C4B | 1.526 (4) |
C8A—C9A | 1.474 (6) | ||
C16A—S1A—C17A | 101.7 (2) | C12A—C11A—C16A | 118.0 (4) |
C23A—F1AB—F2AB | 52 (3) | C16A—C11A—C10A | 119.6 (4) |
C23A—F2AB—F1AB | 46 (2) | C11A—C12A—H12A | 119.5 |
C6A—O1A—H1A | 109.5 | C13A—C12A—C11A | 121.1 (4) |
C1A—N1A—C4A | 108.3 (2) | C13A—C12A—H12A | 119.5 |
C7A—N1A—C1A | 110.6 (3) | C12A—C13A—C23A | 118.8 (4) |
C7A—N1A—C4A | 111.9 (3) | C14A—C13A—C12A | 120.3 (4) |
C2A—N2A—H2A | 108 (2) | C14A—C13A—C23A | 120.9 (4) |
C2A—N2A—C3A | 110.1 (2) | C13A—C14A—H14A | 120.3 |
C2A—N2A—C5A | 108.9 (3) | C13A—C14A—C15A | 119.4 (4) |
C3A—N2A—H2A | 105 (2) | C15A—C14A—H14A | 120.3 |
C3A—N2A—C5A | 111.9 (3) | C14A—C15A—H15A | 119.6 |
C5A—N2A—H2A | 112 (2) | C16A—C15A—C14A | 120.7 (4) |
N1A—C1A—H1AA | 109.7 | C16A—C15A—H15A | 119.6 |
N1A—C1A—H1AB | 109.7 | C11A—C16A—S1A | 122.1 (4) |
N1A—C1A—C2A | 109.9 (3) | C15A—C16A—S1A | 117.5 (3) |
H1AA—C1A—H1AB | 108.2 | C15A—C16A—C11A | 120.4 (4) |
C2A—C1A—H1AA | 109.7 | C18A—C17A—S1A | 118.0 (4) |
C2A—C1A—H1AB | 109.7 | C18A—C17A—C22A | 121.6 (5) |
N2A—C2A—C1A | 111.9 (3) | C22A—C17A—S1A | 120.4 (4) |
N2A—C2A—H2AA | 109.2 | C17A—C18A—H18A | 119.6 |
N2A—C2A—H2AB | 109.2 | C17A—C18A—C19A | 120.8 (5) |
C1A—C2A—H2AA | 109.2 | C19A—C18A—H18A | 119.6 |
C1A—C2A—H2AB | 109.2 | C18A—C19A—H19A | 120.7 |
H2AA—C2A—H2AB | 107.9 | C18A—C19A—C20A | 118.5 (5) |
N2A—C3A—H3AA | 109.3 | C20A—C19A—H19A | 120.7 |
N2A—C3A—H3AB | 109.3 | C19A—C20A—H20A | 119.5 |
N2A—C3A—C4A | 111.8 (3) | C21A—C20A—C19A | 120.9 (5) |
H3AA—C3A—H3AB | 107.9 | C21A—C20A—H20A | 119.5 |
C4A—C3A—H3AA | 109.3 | C20A—C21A—H21A | 119.3 |
C4A—C3A—H3AB | 109.3 | C20A—C21A—C22A | 121.4 (5) |
N1A—C4A—C3A | 111.1 (3) | C22A—C21A—H21A | 119.3 |
N1A—C4A—H4AA | 109.4 | C17A—C22A—C10A | 121.5 (4) |
N1A—C4A—H4AB | 109.4 | C17A—C22A—C21A | 116.5 (4) |
C3A—C4A—H4AA | 109.4 | C21A—C22A—C10A | 121.9 (4) |
C3A—C4A—H4AB | 109.4 | F1A—C23A—F3A | 106.4 (11) |
H4AA—C4A—H4AB | 108.0 | F1A—C23A—C13A | 110.3 (8) |
N2A—C5A—H5AA | 108.6 | F1AB—C23A—F2AB | 82 (5) |
N2A—C5A—H5AB | 108.6 | F1AB—C23A—F3AB | 105 (4) |
N2A—C5A—C6A | 114.7 (3) | F1AB—C23A—C13A | 117.8 (14) |
H5AA—C5A—H5AB | 107.6 | F2A—C23A—F1A | 105.5 (12) |
C6A—C5A—H5AA | 108.6 | F2A—C23A—F3A | 109.1 (9) |
C6A—C5A—H5AB | 108.6 | F2A—C23A—C13A | 114.9 (4) |
O1A—C6A—C5A | 112.0 (3) | F2AB—C23A—C13A | 115.7 (12) |
O1A—C6A—H6AA | 109.2 | F3A—C23A—C13A | 110.3 (6) |
O1A—C6A—H6AB | 109.2 | F3AB—C23A—F2AB | 109 (3) |
C5A—C6A—H6AA | 109.2 | F3AB—C23A—C13A | 120.3 (11) |
C5A—C6A—H6AB | 109.2 | C2B—O3B—H3B | 109.5 |
H6AA—C6A—H6AB | 107.9 | C3B—O4B—H4B | 109.5 |
N1A—C7A—H7AA | 109.5 | C4B—O6B—H6B | 109.5 |
N1A—C7A—H7AB | 109.5 | O1B—C1B—O2B | 126.8 (3) |
N1A—C7A—C8A | 110.8 (3) | O1B—C1B—C2B | 116.5 (3) |
H7AA—C7A—H7AB | 108.1 | O2B—C1B—C2B | 116.7 (3) |
C8A—C7A—H7AA | 109.5 | O3B—C2B—C1B | 110.4 (3) |
C8A—C7A—H7AB | 109.5 | O3B—C2B—H2B | 109.3 |
C7A—C8A—H8AA | 109.7 | O3B—C2B—C3B | 110.3 (3) |
C7A—C8A—H8AB | 109.7 | C1B—C2B—H2B | 109.3 |
H8AA—C8A—H8AB | 108.2 | C3B—C2B—C1B | 108.4 (3) |
C9A—C8A—C7A | 109.8 (3) | C3B—C2B—H2B | 109.3 |
C9A—C8A—H8AA | 109.7 | O4B—C3B—C2B | 110.8 (3) |
C9A—C8A—H8AB | 109.7 | O4B—C3B—H3BA | 108.3 |
C8A—C9A—H9A | 115.3 | O4B—C3B—C4B | 110.7 (3) |
C10A—C9A—C8A | 129.4 (4) | C2B—C3B—H3BA | 108.3 |
C10A—C9A—H9A | 115.3 | C4B—C3B—C2B | 110.4 (3) |
C9A—C10A—C11A | 124.1 (4) | C4B—C3B—H3BA | 108.3 |
C9A—C10A—C22A | 119.2 (4) | O5B—C4B—O6B | 125.0 (3) |
C22A—C10A—C11A | 116.7 (4) | O5B—C4B—C3B | 122.7 (3) |
C12A—C11A—C10A | 122.4 (4) | O6B—C4B—C3B | 112.3 (3) |
S1A—C17A—C18A—C19A | −179.8 (4) | C12A—C13A—C14A—C15A | 1.7 (7) |
S1A—C17A—C22A—C10A | 6.3 (5) | C12A—C13A—C23A—F1A | −141.2 (14) |
S1A—C17A—C22A—C21A | −177.6 (3) | C12A—C13A—C23A—F1AB | 178 (6) |
F1AB—F2AB—C23A—F1A | −22 (3) | C12A—C13A—C23A—F2A | −22.2 (10) |
F1AB—F2AB—C23A—F2A | 138 (3) | C12A—C13A—C23A—F2AB | −88 (4) |
F1AB—F2AB—C23A—F3A | 51 (4) | C12A—C13A—C23A—F3A | 101.6 (10) |
F1AB—F2AB—C23A—F3AB | 104 (4) | C12A—C13A—C23A—F3AB | 47 (4) |
F1AB—F2AB—C23A—C13A | −117 (3) | C13A—C14A—C15A—C16A | −3.1 (7) |
F2AB—F1AB—C23A—F1A | 27 (3) | C14A—C13A—C23A—F1A | 40.3 (14) |
F2AB—F1AB—C23A—F2A | −43 (4) | C14A—C13A—C23A—F1AB | −1 (6) |
F2AB—F1AB—C23A—F3A | −142.6 (18) | C14A—C13A—C23A—F2A | 159.3 (8) |
F2AB—F1AB—C23A—F3AB | −108 (3) | C14A—C13A—C23A—F2AB | 94 (4) |
F2AB—F1AB—C23A—C13A | 115 (3) | C14A—C13A—C23A—F3A | −77.0 (10) |
N1A—C1A—C2A—N2A | −58.7 (3) | C14A—C13A—C23A—F3AB | −132 (4) |
N1A—C7A—C8A—C9A | 169.7 (3) | C14A—C15A—C16A—S1A | −177.8 (4) |
N2A—C3A—C4A—N1A | 57.1 (3) | C14A—C15A—C16A—C11A | 3.8 (7) |
N2A—C5A—C6A—O1A | −80.8 (4) | C16A—S1A—C17A—C18A | −157.3 (3) |
C1A—N1A—C4A—C3A | −61.0 (3) | C16A—S1A—C17A—C22A | 24.3 (4) |
C1A—N1A—C7A—C8A | 158.2 (3) | C16A—C11A—C12A—C13A | 1.8 (6) |
C2A—N2A—C3A—C4A | −51.9 (3) | C17A—S1A—C16A—C11A | −26.5 (4) |
C2A—N2A—C5A—C6A | 165.7 (3) | C17A—S1A—C16A—C15A | 155.1 (4) |
C3A—N2A—C2A—C1A | 53.0 (3) | C17A—C18A—C19A—C20A | −1.9 (7) |
C3A—N2A—C5A—C6A | −72.3 (3) | C18A—C17A—C22A—C10A | −172.0 (4) |
C4A—N1A—C1A—C2A | 61.3 (3) | C18A—C17A—C22A—C21A | 4.1 (6) |
C4A—N1A—C7A—C8A | −80.9 (4) | C18A—C19A—C20A—C21A | 2.5 (7) |
C5A—N2A—C2A—C1A | 176.0 (3) | C19A—C20A—C21A—C22A | 0.3 (7) |
C5A—N2A—C3A—C4A | −173.2 (3) | C20A—C21A—C22A—C10A | 172.6 (4) |
C7A—N1A—C1A—C2A | −175.7 (3) | C20A—C21A—C22A—C17A | −3.5 (6) |
C7A—N1A—C4A—C3A | 176.8 (3) | C22A—C10A—C11A—C12A | −141.7 (4) |
C7A—C8A—C9A—C10A | 135.7 (5) | C22A—C10A—C11A—C16A | 38.5 (5) |
C8A—C9A—C10A—C11A | 2.8 (8) | C22A—C17A—C18A—C19A | −1.5 (7) |
C8A—C9A—C10A—C22A | −174.6 (4) | C23A—C13A—C14A—C15A | −179.8 (4) |
C9A—C10A—C11A—C12A | 40.8 (6) | O1B—C1B—C2B—O3B | 8.5 (4) |
C9A—C10A—C11A—C16A | −139.0 (4) | O1B—C1B—C2B—C3B | −112.4 (3) |
C9A—C10A—C22A—C17A | 136.5 (4) | O2B—C1B—C2B—O3B | −171.3 (3) |
C9A—C10A—C22A—C21A | −39.4 (6) | O2B—C1B—C2B—C3B | 67.8 (4) |
C10A—C11A—C12A—C13A | −178.1 (4) | O3B—C2B—C3B—O4B | −65.3 (3) |
C10A—C11A—C16A—S1A | −1.6 (5) | O3B—C2B—C3B—C4B | 57.7 (4) |
C10A—C11A—C16A—C15A | 176.7 (4) | O4B—C3B—C4B—O5B | 4.4 (5) |
C11A—C10A—C22A—C17A | −41.1 (6) | O4B—C3B—C4B—O6B | −178.0 (3) |
C11A—C10A—C22A—C21A | 143.0 (4) | C1B—C2B—C3B—O4B | 55.6 (3) |
C11A—C12A—C13A—C14A | −1.1 (6) | C1B—C2B—C3B—C4B | 178.6 (3) |
C11A—C12A—C13A—C23A | −179.6 (4) | C2B—C3B—C4B—O5B | −118.7 (4) |
C12A—C11A—C16A—S1A | 178.5 (3) | C2B—C3B—C4B—O6B | 58.9 (4) |
C12A—C11A—C16A—C15A | −3.1 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O1Bi | 0.82 | 1.83 | 2.652 (4) | 178 |
N2A—H2A···O2Bi | 0.96 (4) | 1.73 (4) | 2.675 (3) | 165 (3) |
O3B—H3B···O5Bii | 0.82 | 2.18 | 2.903 (3) | 147 |
O4B—H4B···O3Bii | 0.82 | 2.14 | 2.954 (4) | 175 |
O6B—H6B···N1A | 0.82 | 1.83 | 2.629 (4) | 165 |
C3A—H3AB···O5B | 0.97 | 2.59 | 3.314 (4) | 132 |
C5A—H5AA···O2Biii | 0.97 | 2.53 | 3.466 (4) | 163 |
C15A—H15A···O1Aiv | 0.93 | 2.58 | 3.397 (5) | 148 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) x+1/2, −y+1/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O1Bi | 0.82 | 1.83 | 2.652 (4) | 178 |
N2A—H2A···O2Bi | 0.96 (4) | 1.73 (4) | 2.675 (3) | 165 (3) |
O3B—H3B···O5Bii | 0.82 | 2.18 | 2.903 (3) | 147 |
O4B—H4B···O3Bii | 0.82 | 2.14 | 2.954 (4) | 175 |
O6B—H6B···N1A | 0.82 | 1.83 | 2.629 (4) | 165 |
C3A—H3AB···O5B | 0.97 | 2.59 | 3.314 (4) | 132 |
C5A—H5AA···O2Biii | 0.97 | 2.53 | 3.466 (4) | 163 |
C15A—H15A···O1Aiv | 0.93 | 2.58 | 3.397 (5) | 148 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) x+1/2, −y+1/2, z−1/2. |
Acknowledgements
TSY thanks the University of Mysore for research facilities and is also grateful to the Principal, Maharani's Science College for Women, Mysore, for giving permission to undertake research. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.
References
Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England. Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Jones, P. G., Kennard, O. & Horn, A. S. (1977). Acta Cryst. B33, 3744–3747. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786–790. Web of Science CrossRef CAS IUCr Journals Google Scholar
Post, M. L., Kennard, O. & Horn, A. S. (1975a). Acta Cryst. B31, 2724–2726. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Post, M. L., Kennard, O., Sheldrick, G. M. & Horn, A. S. (1975b). Acta Cryst. B31, 2366–2368. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Robertson, M. M. & Trimble, M. R. (1981). Practitioner, 225, 761–763. CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siddegowda, M. S., Butcher, R. J., Akkurt, M., Yathirajan, H. S. & Narayana, B. (2011a). Acta Cryst. E67, o2079–o2080. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Siddegowda, M. S., Butcher, R. J., Akkurt, M., Yathirajan, H. S. & Ramesh, A. R. (2011b). Acta Cryst. E67, o2017–o2018. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Valle-Jones, J. C. & Swarbrick, D. J. (1981). Curr. Med. Res. Opin. 1, 543–549. Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Flupentixol [systematic name: 2-[4-[3-[(EZ)-2-(trifluoromethyl)-9H- thioxanthen-9-ylidene] propyl]piperazin-1-yl]ethanol is a well documented antipsychotic drug of the thioxanthene class. In addition to pure drug preparations, it is also available as deanxit, a combination product containing both melitracen and flupentixol. Low-dose neuroleptics have been applied increasingly in recent years to treat anxiety and depression (Robertson & Trimble, 1981; Valle-Jones & Swarbrick, 1981). The crystal structures of α-flupentixol (Post et al., 1975b), β-flupentixol (Post et al., 1975a), piflutixol (Jones et al., 1977) have been reported. The crystal structures of he dihydrochloride and difumarate salt of flupentixol has been reported by our group (Siddegowda et al., 2011a,b). In view of the importance of flupentixol, we prepared the tartrate salt of flupentixol and report herein on its crystal structure.
The title salt, Fig. 1, crystallizes with one independent monocation (A) and monoanion (B) in the asymmetric unit. Bond lengths are in normal ranges (Allen et al., 1987). The monoprotonated piperazine ring in A adopts a slightly disordered chair conformation while the thiopyran ring of the thioxanthene group has a boat conformation. The puckering parameters (Cremer & Pople, 1975) for the various rings are: (N1A//N2A/C1A-C4A) Q, θ, and φ = 0.578 (3) Å, 174.4 (3)° and 192 (3)°, respectively; (S1A/C16A/C11A/C10A/C22A/C17A) Q, θ, and φ = 0.486 (4) Å, 90.7 (5)° and 2.0 (5)°, respectively. The dihedral angle between the mean planes of the two outer aromatic rings of the thioxanthene groups is 31.6 (2)°.
In the crystal, the cations and anions are linked via O-H···O, N-H···O, O-H···N and C-H···O hydrogen bonds (Fig. 1), forming one-dimensional chains propagating along [1 0 0] (see Table 1 and Fig. 2). In addition, R22(7), R22(11), R22(10) and R22(12) graph set ring motifs involving the anions (Fig. 3) and R22(9) graph set ring motifs involving both the cations and anions (Fig. 2) are observed.