research communications
A very short O—H⋯O hydrogen bond in the structure of clozapinium hydrogen bis(3,5-dinitrobenzoate)
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India, bDepartment of Chemistry, Maharani's Science College for Women, Mysuru 570 001, India, cInstitute of Materials Science, Darmstadt University of Technology, Alarich-Weiss-Strasse 2, D-64287 Darmstadt, Germany, and dSchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UK
*Correspondence e-mail: yathirajan@hotmail.com
In the title salt {systematic name: 4-[6-chloro-2,9-diazatricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,9,11,13-heptaen-10-yl]-1-methylpiperazin-1-ium 3,5-dinitrobenzoate–3,5-dinitrobenzic acid (1/1)}, C18H20ClN4+·C7H3N2O6−·C7H4N2O6, there is a very short, asymmetric, O—H⋯O hydrogen bond [O⋯O = 2.453 (3) Å] within the anion. The oxygen atoms of one of the nitro groups of the anion are disordered over two sets of sites having occupancies of 0.56 (3) and 0.44 (3). The fused tricyclic portion of the cation adopts a butterfly conformation, with a dihedral angle of 45.59 (6)° between the planes of the two aryl rings. In the crystal, a combination of O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds links the component species into a three-dimensional framework. Comparisons are made with the structures of some related compounds.
Keywords: clozapine; crystal structure; molecular conformation; hydrogen bonding; very short hydrogen bonds; supramolecular assembly.
CCDC reference: 2027224
1. Chemical context
Clozapine, 8-chloro-11-(4-methylpiperazin-1-yl)-5H-dibenzo[b,e][1,4]diazepine, C18H19ClN4, is a well established medication for the treatment of schizophrenia, often preferred over other treatments because of the generally lower incidence of adverse side effects (Breier et al., 1994). The structure of the free base has been reported (Petcher & Weber, 1976; Fillers & Hawkinson, 1982), along with those of a few salts (Fillers & Hawkinson, 1982; Kaur et al., 2015). Among the latter is the 1:1 salt formed by the reaction of clozapine with an equimolar quantity of 3,5-dinitrobenzoic acid in methanol followed by slow crystallization from dimethylsulfoxide solution, when a DMSO monosolvate of the 1:1 salt was obtained (Kaur et al., 2015).
We have now found that repetition of this process but with the substitution of dimethylsulfoxide by a 1:1 mixture of chloroform and methanol gives the solvent-free 1:2 acid salt chlozapinium hydrogen bis(3,5-dinitrobenzoate), (I), whose structure we report here along with comparisons between the structure of (I) and those of both the solvated 1:1 salt, (II), (Kaur et al., 2015) and the 1:2 acid salt, (III), formed between 3,5-dinitrobenzoic acid and the antipsychotic agent chlorprothixene, 3-(2-chloro-9H-thioxanthen-9-yl)-N,N-dimethylpropan-1-amine (Shaibah et al., 2019).
2. Structural commentary
Compound (I) is an acid salt, i.e., the contains one C18H20ClN4+ clozapinium cation and one C14H7N4O12− hydrogen bis(3,5-dinotrobenzoate) anion (Fig. 1). An alternative description is one cation, one 3,5-dinitrobenzote anion and one neutral molecule of 3,5-dinitrobenzoic acid, i.e., C18H20ClN4+·(C7H3N2O6)−·(C7H4N2O6). The –CO2H and –CO2− groups in the anion are linked by a very short O22—H22A⋯O32 hydrogen bond (Table 1) (Speakman, 1972; Emsley, 1980; Gerlt et al., 1997) but, although it is nearly linear [169 (3)°], it is not symmetric as the two independent O—H distances are significantly different [O22—H22A = 1.11 (4); H22A⋯O32 = 1.35 (4) Å]. There is a similarly short O—H⋯O hydrogen bond in the corresponding species of the chlorprothixene salt (III) (Shaibah et al., 2019), where the O⋯O distance, 2.4197 (15) Å, is slightly shorter than that found here for (I), while the difference between the two independent O—H distances is about 50% higher in (III) as compared to (I). For (I) it is possible to select a compact in which the components are linked by O—H⋯O and N—H⋯O hydrogen bonds (Table 1, Fig. 1). Within this there are also two fairly short C—H⋯O contacts. That involving atom C4 has a small C—H⋯O angle, and so it probably not structurally significant (Wood et al., 2009), while for that involving atom C13, the H⋯O distance is not significantly shorter that the sum of the van der Waals radii (Rowland & Taylor, 1996). These are both probably better regarded as adventitious contacts rather than as structurally significant hydrogen bonds.
One of the nitro groups of the anion, that attached to C35, is disordered over two sets of atomic sites, with occupancies of 0.56 (3) and 0.44 (3) for the oxygen atoms. The major and minor disorder components make dihedral angles with the adjacent aryl ring of 17.2 (8) and 19.4 (8)°, with a dihedral angle between their own planes of 36.5 (14)°, so that these components are rotated out of the plane of the aryl ring in opposite senses.
In the C18H20ClN4+ cation of (I), the fused tricyclic component adopts a butterfly conformation with a dihedral angle of 45.59 (6)° between the planes of the two outer aryl rings. The piperazine ring adopts a chair conformation, as indicated by the value of the ring-puckering angle θ = 176.0 (3)°, as calculated for the atom sequence N11/C12/C13/N14/C15/C16: for an idealized chair form this angle takes a value of either zero or 180° (Boeyens, 1978). The site of protonation is the methylated atom N14 where the methyl substituent occupies the equatorial site (Fig. 1). The geometry at the other N atom in this ring, atom N11, is nearly planar: the sum of the C—N—C angles at N11 is 351.9°, as compared with 344.1° at N14, while the displacements of these N atoms from the planes of the adjacent three C atoms are 0.449 (3) Å for N14 and 0.236 (2) Å for N11.
3. Supramolecular features
Aggregates of the type defining the selected ) are linked by a combination of one N—H⋯O, one O—H⋯O and two C—H⋯O hydrogen bonds (Table 1) to form a three-dimensional network: since both disorder components participate in similar hydrogen bonds, it is necessary to consider only the interactions involving the major component. The formation of the hydrogen-bonded network is readily analysed in terms of three simple sub-structures (Ferguson et al., 1998a,b; Gregson et al., 2000), in which the aggregates are linked in different ways, each utilizing just one of the three inter-aggregate hydrogen bonds. The N14–H14⋯O31i (see Table 1 for symmetry codes) hydrogen bond links the aggregates into a C33(17) (Etter, 1990; Etter et al., 1990; Bernstein et al., 1995) chain running parallel to the [010] direction (Fig. 2). In the second sub-structure, the C1—H1⋯O35ii hydrogen bond links the aggregates into another C33(17) chain, this time running parallel to the [101] direction (Fig. 3). In the final sub-structure, the C7—H7⋯O36iii hydrogen bond links inversion-related pairs of aggregates into a cyclic centrosymmetric system characterized by an R66(34) motif (Fig. 4). The combination of the chains along [010] and [101] generates a complex sheet lying parallel to (10), and adjacent sheets are linked by the R66(34) motif, thereby generating a three-dimensional array.
(Fig. 14. Database survey
Here we briefly compare the salient features of the structure of compound (I), with those of some related structures. As noted above (Section 2), the O⋯O distances in the anion of the chlorothixene salt (III) (Shaibah et al., 2019), is slightly shorter than that found here for compound (I). Although the O⋯O distances in (I) and (III) are very short, some even shorter distances have been reported, some below 2.40 Å. One of the simplest organic compounds to display such a short distance is the enol form, Me3C(OH)=C(CN)COCMe3, of the 1,3 diketone 4-cyano 2,2,6,6-tetramethyl3,5-heptanedione, where the intramolecular O—H⋯O hydrogen bond has an O⋯O distance of 2.3936 (15) Å (Belot et al., 2004), while the corresponding distances in some cyclic phosphate derivatives are reported to be as low as 2.368 (4) Å (Kumara Swamy et al., 2001).
The dihedral angles between the planes of the pendent aryl rings in the fused tricyclic portion of various clozapine derivatives show some curious variations. In the free base (Fillers & Hawkinson, 1982) this angle is 67.3° [unfortunately, the atomic coordinates retrieved from the CSD (Groom et al., 2016) have no s.u. values] and in the monohydrate (CSD refcode DEHBUP; the publication cited in the CSD could not be traced) and the methanol solvate (Verma et al., 2018), the corresponding angles are 63.4 and 56.1°, respectively. In the 1:1 salt formed with 3,5-dinitrobenzoic acid (II), this angle is 62.21 (11)° (Kaur et al., 2015), fairly similar to the values of 60.97 (9) and 59.07 (16)° in the 1:1 salts formed with maleic and 2-hydroxybenzoic acids, respectively (Kaur et al., 2015). In the di(hydrobomide) salt, the angle is 52.3° (Fillers & Hawkinson, 1982), while in the ethanol solvate of clozapine N-oxide, the corresponding angle is 56.2° (van der Peet et al., 2018). There are, at present, too few data for any pattern to be discernible in the variation of this dihedral angle.
The hydrogen-bonded supramolecular assembly of compound (I) is three dimensional (Section 3, above), but in the solvated 1:1 salt (II), the hydrogen-bonded ion pairs are linked into chains by a π–π stacking interaction (Kaur et al., 2015). There are no hydrogen bonds in the structure of clozapine itself (Fillers & Hawkinson, 1982), but in the monohydrate (DEHBUP), a combination of one N—H⋯O hydrogen bond and two O—H⋯N hydrogen bonds links the components into a chain of rings. In the methanol solvate of clozapine (Verma et al., 2018), the components are linked by an O—H⋯N hydrogen bond, but with no further aggregation. In the hydrogenmaleate and 2-hydroxybenzoate salts, multiple hydrogen bonds generate sheets and a three-dimensional supramolecular network, respectively (Kaur et al., 2015), while in the di(hydrobromide) salt, the ions are linked into chains by N—H⋯Br hydrogen bonds (Fillers & Hawkinson, 1982).
5. Synthesis and crystallization
Clozapine (100 mg, 0.31 mmol) and 3,5-dinitrobenzoic acid (66 mg, 0.31mmol) were dissolved in methanol (10 ml), and this mixture was then stirred at 333 K for a few minutes. The solution was permitted to cool to room temperature and the resulting crystals were then collected by filtration and dried over P2O5. Crystals of (I) suitable for single-crystal X-ray diffraction were obtained by slow evaporation, at room temperature and in the presence of air, of a solution in the mixed solvents of chloroform and methanol (initial composition 1:1, v/v); m.p. 494–497 K.
6. Refinement
Crystal data, data collection and . All H atoms were located in difference maps. The H atoms bonded to C atoms were then treated as riding atoms in geometrically idealized positions with C—H distances of 0.93 Å (aromatic), 0.96 Å (CH3) or 0.97 Å (CH2), and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C); the CH3 group was permitted to rotate but not to tilt. For the H atoms bonded to N or O atoms, the atomic coordinates were refined with Uiso(H) = 1.2Ueq(N) or 1.5Ueq(O). For the minor disorder component, the N—O distances and the 1,3-non-bonded O⋯O distances were restrained to be the same of the corresponding distances in the major component, subject to s.u. values of 0.01 and 0.02 Å, respectively. In addition, a similarity restraint was applied to the disordered O-atom sites and for each of the disorder components, the C—NO2 fragment was restrained to be planar. Subject to these conditions, the refined disorder occupancies are 0.56 (3) and 0.44 (3).
details are summarized in Table 2
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Supporting information
CCDC reference: 2027224
https://doi.org/10.1107/S2056989020012268/hb7944sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989020012268/hb7944Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989020012268/hb7944Isup3.cml
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell
CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2020).C18H20ClN4+·C7H3N2O6−·C7H4N2O6 | F(000) = 1552 |
Mr = 751.07 | Dx = 1.498 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.4102 (6) Å | Cell parameters from 7183 reflections |
b = 24.629 (2) Å | θ = 2.8–27.9° |
c = 18.446 (1) Å | µ = 0.19 mm−1 |
β = 98.478 (6)° | T = 296 K |
V = 3329.7 (4) Å3 | Needle, red |
Z = 4 | 0.36 × 0.24 × 0.20 mm |
Oxford Diffraction Xcalibur Sapphire CCD detector diffractometer | 6870 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3811 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
ω scans | θmax = 26.6°, θmin = 2.8° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −9→8 |
Tmin = 0.914, Tmax = 0.962 | k = −18→30 |
13700 measured reflections | l = −20→23 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.062 | Hydrogen site location: mixed |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0452P)2 + 1.0626P] where P = (Fo2 + 2Fc2)/3 |
6870 reflections | (Δ/σ)max < 0.001 |
507 parameters | Δρmax = 0.16 e Å−3 |
17 restraints | Δρmin = −0.19 e Å−3 |
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) | |
C1 | 0.3444 (4) | 0.23128 (13) | 0.08513 (15) | 0.0519 (8) | |
H1 | 0.3445 | 0.1944 | 0.0957 | 0.062* | |
C2 | 0.2571 (4) | 0.24929 (16) | 0.01823 (17) | 0.0659 (9) | |
H2 | 0.1993 | 0.2247 | −0.0157 | 0.079* | |
C3 | 0.2559 (4) | 0.30335 (16) | 0.00210 (16) | 0.0650 (9) | |
H3 | 0.2007 | 0.3155 | −0.0436 | 0.078* | |
C4 | 0.3359 (4) | 0.33980 (13) | 0.05311 (15) | 0.0525 (8) | |
H4 | 0.3326 | 0.3767 | 0.0421 | 0.063* | |
C4A | 0.4220 (3) | 0.32228 (11) | 0.12132 (13) | 0.0383 (6) | |
N5 | 0.5009 (3) | 0.36063 (10) | 0.17327 (12) | 0.0437 (6) | |
H5 | 0.492 (4) | 0.3941 (12) | 0.1564 (15) | 0.052* | |
C5A | 0.4443 (3) | 0.35994 (11) | 0.24375 (13) | 0.0374 (6) | |
C6 | 0.3781 (4) | 0.40729 (12) | 0.27020 (15) | 0.0458 (7) | |
H6 | 0.3563 | 0.4371 | 0.2391 | 0.055* | |
C7 | 0.3434 (4) | 0.41167 (13) | 0.34144 (16) | 0.0519 (8) | |
H7 | 0.3007 | 0.4440 | 0.3586 | 0.062* | |
C8 | 0.3733 (4) | 0.36715 (13) | 0.38635 (15) | 0.0487 (7) | |
Cl8 | 0.34891 (13) | 0.37265 (4) | 0.47895 (4) | 0.0768 (3) | |
C9 | 0.4298 (3) | 0.31860 (12) | 0.36041 (14) | 0.0463 (7) | |
H9 | 0.4435 | 0.2884 | 0.3910 | 0.056* | |
C9A | 0.4666 (3) | 0.31418 (11) | 0.28869 (14) | 0.0379 (6) | |
N10 | 0.5458 (3) | 0.26494 (9) | 0.27155 (11) | 0.0410 (5) | |
C11 | 0.5353 (3) | 0.24542 (11) | 0.20636 (14) | 0.0396 (6) | |
C11A | 0.4322 (3) | 0.26698 (11) | 0.13697 (13) | 0.0391 (6) | |
N11 | 0.6093 (3) | 0.19388 (9) | 0.20017 (11) | 0.0451 (6) | |
C12 | 0.6660 (4) | 0.16212 (12) | 0.26609 (15) | 0.0524 (8) | |
H12A | 0.6413 | 0.1241 | 0.2553 | 0.063* | |
H12B | 0.5939 | 0.1729 | 0.3035 | 0.063* | |
C13 | 0.8645 (4) | 0.16879 (12) | 0.29558 (15) | 0.0524 (8) | |
H13A | 0.8889 | 0.2062 | 0.3105 | 0.063* | |
H13B | 0.8964 | 0.1457 | 0.3382 | 0.063* | |
N14 | 0.9768 (3) | 0.15369 (10) | 0.23769 (13) | 0.0472 (6) | |
H14 | 0.947 (4) | 0.1154 (12) | 0.2223 (14) | 0.057* | |
C15 | 0.9216 (4) | 0.18776 (12) | 0.17106 (15) | 0.0508 (7) | |
H15A | 0.9913 | 0.1769 | 0.1329 | 0.061* | |
H15B | 0.9492 | 0.2255 | 0.1828 | 0.061* | |
C16 | 0.7201 (4) | 0.18191 (12) | 0.14324 (15) | 0.0471 (7) | |
H16A | 0.6868 | 0.2064 | 0.1023 | 0.057* | |
H16B | 0.6954 | 0.1451 | 0.1257 | 0.057* | |
C17 | 1.1766 (4) | 0.15711 (16) | 0.2639 (2) | 0.0800 (11) | |
H17A | 1.2074 | 0.1934 | 0.2803 | 0.120* | |
H17B | 1.2425 | 0.1480 | 0.2245 | 0.120* | |
H17C | 1.2086 | 0.1322 | 0.3037 | 0.120* | |
C21 | 0.2811 (4) | 0.54057 (11) | 0.01705 (14) | 0.0419 (7) | |
C22 | 0.2657 (4) | 0.59602 (12) | 0.00575 (16) | 0.0492 (7) | |
H22 | 0.3254 | 0.6201 | 0.0400 | 0.059* | |
C23 | 0.1607 (4) | 0.61492 (13) | −0.05705 (17) | 0.0535 (8) | |
C24 | 0.0736 (4) | 0.58098 (14) | −0.11005 (17) | 0.0572 (8) | |
H24 | 0.0046 | 0.5945 | −0.1524 | 0.069* | |
C25 | 0.0928 (4) | 0.52651 (13) | −0.09794 (15) | 0.0484 (7) | |
C26 | 0.1939 (4) | 0.50581 (12) | −0.03532 (15) | 0.0456 (7) | |
H26 | 0.2033 | 0.4684 | −0.0284 | 0.055* | |
C27 | 0.3916 (4) | 0.51740 (13) | 0.08452 (16) | 0.0473 (7) | |
O21 | 0.3873 (3) | 0.46873 (9) | 0.09583 (11) | 0.0678 (6) | |
O22 | 0.4857 (3) | 0.55163 (8) | 0.12759 (12) | 0.0570 (6) | |
H22A | 0.572 (5) | 0.5330 (14) | 0.1755 (19) | 0.085* | |
N23 | 0.1434 (5) | 0.67388 (13) | −0.0680 (2) | 0.0740 (9) | |
O23 | 0.2158 (4) | 0.70360 (11) | −0.0192 (2) | 0.1043 (10) | |
O24 | 0.0524 (5) | 0.68988 (11) | −0.12377 (16) | 0.1095 (10) | |
N25 | −0.0005 (4) | 0.48816 (15) | −0.15269 (16) | 0.0669 (8) | |
O25 | 0.0063 (4) | 0.44003 (12) | −0.13688 (13) | 0.0836 (8) | |
O26 | −0.0774 (3) | 0.50674 (12) | −0.21036 (14) | 0.0935 (9) | |
C31 | 0.7597 (4) | 0.47059 (12) | 0.34692 (15) | 0.0446 (7) | |
C32 | 0.8228 (4) | 0.42264 (12) | 0.32110 (15) | 0.0463 (7) | |
H32 | 0.8254 | 0.4179 | 0.2713 | 0.056* | |
C33 | 0.8817 (4) | 0.38203 (11) | 0.37005 (15) | 0.0447 (7) | |
C34 | 0.8818 (4) | 0.38730 (12) | 0.44445 (16) | 0.0496 (7) | |
H34 | 0.9216 | 0.3594 | 0.4769 | 0.060* | |
C35 | 0.8204 (4) | 0.43570 (12) | 0.46830 (15) | 0.0503 (7) | |
C36 | 0.7589 (4) | 0.47737 (12) | 0.42137 (15) | 0.0505 (7) | |
H36 | 0.7173 | 0.5096 | 0.4394 | 0.061* | |
C37 | 0.6800 (4) | 0.51417 (14) | 0.29415 (17) | 0.0507 (8) | |
O31 | 0.6202 (3) | 0.55554 (9) | 0.31888 (12) | 0.0689 (6) | |
O32 | 0.6772 (3) | 0.50299 (9) | 0.22654 (12) | 0.0653 (6) | |
N33 | 0.9440 (3) | 0.33021 (11) | 0.34261 (16) | 0.0565 (7) | |
O33 | 0.9549 (3) | 0.32681 (10) | 0.27753 (13) | 0.0774 (7) | |
O34 | 0.9802 (4) | 0.29336 (9) | 0.38628 (13) | 0.0768 (7) | |
N35 | 0.8168 (5) | 0.44262 (13) | 0.54739 (15) | 0.0740 (9) | 0.44 (3) |
O35 | 0.830 (4) | 0.4023 (5) | 0.5865 (10) | 0.086 (5) | 0.44 (3) |
O36 | 0.816 (3) | 0.4907 (3) | 0.5686 (6) | 0.078 (3) | 0.44 (3) |
N45 | 0.8168 (5) | 0.44262 (13) | 0.54739 (15) | 0.0740 (9) | 0.56 (3) |
O45 | 0.900 (2) | 0.4100 (6) | 0.5902 (8) | 0.084 (4) | 0.56 (3) |
O46 | 0.712 (3) | 0.4787 (6) | 0.5660 (5) | 0.098 (4) | 0.56 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0503 (18) | 0.0489 (19) | 0.0549 (18) | 0.0007 (16) | 0.0026 (14) | −0.0084 (15) |
C2 | 0.059 (2) | 0.076 (3) | 0.057 (2) | 0.007 (2) | −0.0099 (16) | −0.0188 (19) |
C3 | 0.064 (2) | 0.084 (3) | 0.0425 (17) | 0.017 (2) | −0.0079 (15) | −0.0011 (18) |
C4 | 0.0569 (19) | 0.054 (2) | 0.0453 (17) | 0.0110 (17) | 0.0035 (14) | 0.0052 (15) |
C4A | 0.0344 (15) | 0.0427 (17) | 0.0383 (14) | 0.0025 (13) | 0.0067 (12) | −0.0013 (13) |
N5 | 0.0507 (14) | 0.0357 (14) | 0.0448 (13) | −0.0013 (12) | 0.0074 (11) | 0.0039 (11) |
C5A | 0.0299 (14) | 0.0396 (16) | 0.0412 (15) | −0.0018 (13) | 0.0000 (11) | −0.0033 (13) |
C6 | 0.0411 (16) | 0.0384 (17) | 0.0571 (18) | 0.0022 (14) | 0.0049 (13) | −0.0026 (14) |
C7 | 0.0440 (17) | 0.0478 (19) | 0.064 (2) | 0.0034 (16) | 0.0089 (15) | −0.0175 (16) |
C8 | 0.0429 (17) | 0.060 (2) | 0.0429 (16) | 0.0014 (16) | 0.0059 (13) | −0.0100 (15) |
Cl8 | 0.0832 (6) | 0.0991 (7) | 0.0497 (5) | 0.0122 (6) | 0.0154 (4) | −0.0144 (5) |
C9 | 0.0409 (17) | 0.0518 (19) | 0.0443 (16) | 0.0026 (15) | 0.0006 (13) | −0.0010 (14) |
C9A | 0.0333 (14) | 0.0371 (16) | 0.0411 (15) | 0.0009 (13) | −0.0021 (11) | −0.0010 (12) |
N10 | 0.0389 (13) | 0.0390 (14) | 0.0441 (13) | 0.0087 (11) | 0.0027 (10) | −0.0006 (11) |
C11 | 0.0351 (15) | 0.0352 (16) | 0.0489 (16) | 0.0000 (13) | 0.0069 (12) | 0.0018 (13) |
C11A | 0.0324 (14) | 0.0413 (17) | 0.0430 (15) | 0.0024 (13) | 0.0031 (12) | −0.0024 (13) |
N11 | 0.0502 (14) | 0.0387 (14) | 0.0478 (13) | 0.0101 (12) | 0.0113 (11) | 0.0044 (11) |
C12 | 0.063 (2) | 0.0390 (17) | 0.0585 (18) | 0.0109 (16) | 0.0202 (15) | 0.0089 (14) |
C13 | 0.070 (2) | 0.0381 (17) | 0.0485 (17) | 0.0090 (16) | 0.0081 (15) | −0.0001 (14) |
N14 | 0.0435 (14) | 0.0375 (14) | 0.0601 (15) | −0.0027 (12) | 0.0058 (12) | 0.0006 (12) |
C15 | 0.0501 (18) | 0.0459 (18) | 0.0577 (18) | 0.0016 (15) | 0.0125 (14) | 0.0069 (15) |
C16 | 0.0513 (18) | 0.0410 (17) | 0.0497 (16) | 0.0081 (15) | 0.0095 (14) | −0.0012 (13) |
C17 | 0.047 (2) | 0.085 (3) | 0.102 (3) | −0.011 (2) | −0.0084 (18) | 0.011 (2) |
C21 | 0.0397 (16) | 0.0394 (17) | 0.0491 (16) | 0.0045 (14) | 0.0143 (13) | 0.0086 (14) |
C22 | 0.0489 (18) | 0.0438 (18) | 0.0572 (18) | 0.0033 (15) | 0.0155 (14) | 0.0068 (15) |
C23 | 0.0553 (19) | 0.0463 (19) | 0.063 (2) | 0.0138 (16) | 0.0242 (16) | 0.0188 (16) |
C24 | 0.0485 (18) | 0.072 (2) | 0.0536 (19) | 0.0149 (18) | 0.0167 (15) | 0.0165 (18) |
C25 | 0.0393 (16) | 0.061 (2) | 0.0470 (17) | 0.0030 (16) | 0.0125 (13) | 0.0008 (15) |
C26 | 0.0447 (16) | 0.0402 (17) | 0.0545 (17) | 0.0030 (15) | 0.0163 (14) | 0.0049 (14) |
C27 | 0.0453 (17) | 0.0438 (19) | 0.0538 (18) | 0.0053 (16) | 0.0106 (14) | 0.0073 (15) |
O21 | 0.0881 (17) | 0.0404 (14) | 0.0693 (14) | −0.0031 (12) | −0.0071 (12) | 0.0128 (11) |
O22 | 0.0648 (14) | 0.0430 (13) | 0.0590 (12) | 0.0008 (11) | −0.0045 (11) | 0.0028 (11) |
N23 | 0.081 (2) | 0.055 (2) | 0.093 (2) | 0.0222 (19) | 0.0367 (19) | 0.0277 (19) |
O23 | 0.105 (2) | 0.0486 (17) | 0.154 (3) | 0.0056 (16) | 0.002 (2) | 0.0118 (18) |
O24 | 0.162 (3) | 0.081 (2) | 0.0900 (19) | 0.050 (2) | 0.0330 (19) | 0.0453 (16) |
N25 | 0.0485 (16) | 0.091 (3) | 0.0623 (19) | 0.0074 (18) | 0.0129 (14) | −0.0078 (19) |
O25 | 0.094 (2) | 0.080 (2) | 0.0763 (17) | −0.0145 (17) | 0.0107 (14) | −0.0151 (15) |
O26 | 0.0714 (16) | 0.134 (3) | 0.0680 (16) | 0.0246 (17) | −0.0131 (13) | −0.0087 (16) |
C31 | 0.0415 (16) | 0.0395 (18) | 0.0516 (17) | −0.0065 (14) | 0.0034 (13) | 0.0010 (14) |
C32 | 0.0388 (15) | 0.053 (2) | 0.0468 (16) | −0.0075 (15) | 0.0045 (13) | −0.0017 (15) |
C33 | 0.0401 (16) | 0.0412 (17) | 0.0525 (17) | −0.0044 (14) | 0.0055 (13) | −0.0082 (14) |
C34 | 0.0549 (19) | 0.0364 (17) | 0.0552 (18) | −0.0009 (15) | 0.0003 (14) | −0.0012 (14) |
C35 | 0.062 (2) | 0.0405 (18) | 0.0459 (17) | 0.0014 (16) | 0.0009 (14) | −0.0030 (14) |
C36 | 0.0569 (19) | 0.0342 (17) | 0.0590 (19) | 0.0008 (15) | 0.0043 (15) | −0.0028 (14) |
C37 | 0.0404 (17) | 0.050 (2) | 0.061 (2) | −0.0055 (16) | 0.0050 (14) | 0.0099 (16) |
O31 | 0.0908 (18) | 0.0440 (14) | 0.0705 (14) | 0.0092 (13) | 0.0068 (12) | 0.0120 (12) |
O32 | 0.0626 (14) | 0.0772 (17) | 0.0547 (13) | 0.0112 (13) | 0.0042 (11) | 0.0133 (12) |
N33 | 0.0556 (17) | 0.0492 (17) | 0.0646 (18) | −0.0003 (14) | 0.0084 (14) | −0.0133 (15) |
O33 | 0.0948 (18) | 0.0762 (17) | 0.0617 (15) | 0.0086 (14) | 0.0136 (13) | −0.0210 (13) |
O34 | 0.106 (2) | 0.0430 (14) | 0.0829 (16) | 0.0133 (14) | 0.0195 (14) | 0.0012 (13) |
N35 | 0.116 (3) | 0.0491 (19) | 0.0548 (17) | 0.018 (2) | 0.0041 (17) | −0.0039 (15) |
O35 | 0.146 (15) | 0.058 (5) | 0.052 (5) | 0.019 (7) | 0.012 (7) | 0.004 (4) |
O36 | 0.116 (9) | 0.047 (4) | 0.069 (4) | 0.013 (4) | 0.009 (6) | −0.017 (3) |
N45 | 0.116 (3) | 0.0491 (19) | 0.0548 (17) | 0.018 (2) | 0.0041 (17) | −0.0039 (15) |
O45 | 0.122 (10) | 0.067 (5) | 0.056 (4) | 0.025 (5) | −0.009 (5) | 0.006 (4) |
O46 | 0.171 (10) | 0.064 (5) | 0.062 (3) | 0.038 (7) | 0.026 (6) | −0.007 (3) |
C1—C2 | 1.380 (4) | C16—H16B | 0.9700 |
C1—C11A | 1.388 (4) | C17—H17A | 0.9600 |
C1—H1 | 0.9300 | C17—H17B | 0.9600 |
C2—C3 | 1.364 (5) | C17—H17C | 0.9600 |
C2—H2 | 0.9300 | C21—C26 | 1.378 (4) |
C3—C4 | 1.371 (4) | C21—C22 | 1.384 (4) |
C3—H3 | 0.9300 | C21—C27 | 1.498 (4) |
C4—C4A | 1.393 (4) | C22—C23 | 1.378 (4) |
C4—H4 | 0.9300 | C22—H22 | 0.9300 |
C4A—C11A | 1.392 (4) | C23—C24 | 1.373 (4) |
C4A—N5 | 1.410 (3) | C23—N23 | 1.469 (4) |
N5—C5A | 1.424 (3) | C24—C25 | 1.364 (4) |
N5—H5 | 0.88 (3) | C24—H24 | 0.9300 |
C5A—C6 | 1.382 (4) | C25—C26 | 1.379 (4) |
C5A—C9A | 1.394 (4) | C25—N25 | 1.478 (4) |
C6—C7 | 1.380 (4) | C26—H26 | 0.9300 |
C6—H6 | 0.9300 | C27—O21 | 1.218 (3) |
C7—C8 | 1.372 (4) | C27—O22 | 1.290 (3) |
C7—H7 | 0.9300 | O22—H22A | 1.11 (4) |
C8—C9 | 1.376 (4) | N23—O24 | 1.210 (4) |
C8—Cl8 | 1.749 (3) | N23—O23 | 1.221 (4) |
C9—C9A | 1.394 (4) | N25—O26 | 1.220 (3) |
C9—H9 | 0.9300 | N25—O25 | 1.220 (4) |
C9A—N10 | 1.404 (3) | C31—C32 | 1.380 (4) |
N10—C11 | 1.287 (3) | C31—C36 | 1.384 (4) |
C11—N11 | 1.394 (3) | C31—C37 | 1.510 (4) |
C11—C11A | 1.489 (4) | C32—C33 | 1.375 (4) |
N11—C12 | 1.455 (3) | C32—H32 | 0.9300 |
N11—C16 | 1.455 (3) | C33—C34 | 1.378 (4) |
C12—C13 | 1.500 (4) | C33—N33 | 1.472 (4) |
C12—H12A | 0.9700 | C34—C35 | 1.372 (4) |
C12—H12B | 0.9700 | C34—H34 | 0.9300 |
C13—N14 | 1.494 (3) | C35—C36 | 1.376 (4) |
C13—H13A | 0.9700 | C35—N35 | 1.473 (4) |
C13—H13B | 0.9700 | C36—H36 | 0.9300 |
N14—C17 | 1.490 (4) | C37—O31 | 1.226 (4) |
N14—C15 | 1.495 (3) | C37—O32 | 1.274 (3) |
N14—H14 | 1.00 (3) | O32—H22A | 1.35 (4) |
C15—C16 | 1.512 (4) | N33—O34 | 1.217 (3) |
C15—H15A | 0.9700 | N33—O33 | 1.218 (3) |
C15—H15B | 0.9700 | N35—O35 | 1.224 (8) |
C16—H16A | 0.9700 | N35—O36 | 1.249 (6) |
C2—C1—C11A | 121.5 (3) | H15A—C15—H15B | 108.0 |
C2—C1—H1 | 119.2 | N11—C16—C15 | 111.7 (2) |
C11A—C1—H1 | 119.2 | N11—C16—H16A | 109.3 |
C3—C2—C1 | 119.8 (3) | C15—C16—H16A | 109.3 |
C3—C2—H2 | 120.1 | N11—C16—H16B | 109.3 |
C1—C2—H2 | 120.1 | C15—C16—H16B | 109.3 |
C2—C3—C4 | 120.1 (3) | H16A—C16—H16B | 107.9 |
C2—C3—H3 | 120.0 | N14—C17—H17A | 109.5 |
C4—C3—H3 | 120.0 | N14—C17—H17B | 109.5 |
C3—C4—C4A | 120.8 (3) | H17A—C17—H17B | 109.5 |
C3—C4—H4 | 119.6 | N14—C17—H17C | 109.5 |
C4A—C4—H4 | 119.6 | H17A—C17—H17C | 109.5 |
C11A—C4A—C4 | 119.6 (3) | H17B—C17—H17C | 109.5 |
C11A—C4A—N5 | 120.7 (2) | C26—C21—C22 | 119.2 (3) |
C4—C4A—N5 | 119.7 (3) | C26—C21—C27 | 119.2 (3) |
C4A—N5—C5A | 117.7 (2) | C22—C21—C27 | 121.6 (3) |
C4A—N5—H5 | 112.6 (18) | C23—C22—C21 | 118.9 (3) |
C5A—N5—H5 | 108.5 (18) | C23—C22—H22 | 120.5 |
C6—C5A—C9A | 119.3 (2) | C21—C22—H22 | 120.5 |
C6—C5A—N5 | 118.7 (2) | C24—C23—C22 | 122.7 (3) |
C9A—C5A—N5 | 121.8 (2) | C24—C23—N23 | 118.8 (3) |
C7—C6—C5A | 121.9 (3) | C22—C23—N23 | 118.5 (3) |
C7—C6—H6 | 119.1 | C25—C24—C23 | 117.1 (3) |
C5A—C6—H6 | 119.1 | C25—C24—H24 | 121.4 |
C8—C7—C6 | 118.4 (3) | C23—C24—H24 | 121.4 |
C8—C7—H7 | 120.8 | C24—C25—C26 | 122.1 (3) |
C6—C7—H7 | 120.8 | C24—C25—N25 | 119.3 (3) |
C7—C8—C9 | 121.0 (3) | C26—C25—N25 | 118.5 (3) |
C7—C8—Cl8 | 119.8 (2) | C21—C26—C25 | 119.9 (3) |
C9—C8—Cl8 | 119.2 (2) | C21—C26—H26 | 120.1 |
C8—C9—C9A | 120.7 (3) | C25—C26—H26 | 120.1 |
C8—C9—H9 | 119.7 | O21—C27—O22 | 124.3 (3) |
C9A—C9—H9 | 119.7 | O21—C27—C21 | 119.5 (3) |
C9—C9A—C5A | 118.6 (3) | O22—C27—C21 | 116.2 (3) |
C9—C9A—N10 | 115.3 (2) | C27—O22—H22A | 114.6 (17) |
C5A—C9A—N10 | 125.5 (2) | O24—N23—O23 | 124.1 (3) |
C11—N10—C9A | 124.3 (2) | O24—N23—C23 | 117.7 (4) |
N10—C11—N11 | 116.5 (2) | O23—N23—C23 | 118.1 (3) |
N10—C11—C11A | 128.5 (2) | O26—N25—O25 | 124.8 (3) |
N11—C11—C11A | 114.4 (2) | O26—N25—C25 | 117.9 (3) |
C1—C11A—C4A | 118.1 (2) | O25—N25—C25 | 117.3 (3) |
C1—C11A—C11 | 119.7 (3) | C32—C31—C36 | 119.8 (3) |
C4A—C11A—C11 | 122.2 (2) | C32—C31—C37 | 120.4 (3) |
C11—N11—C12 | 119.3 (2) | C36—C31—C37 | 119.7 (3) |
C11—N11—C16 | 120.9 (2) | C33—C32—C31 | 119.1 (3) |
C12—N11—C16 | 111.7 (2) | C33—C32—H32 | 120.4 |
N11—C12—C13 | 113.0 (2) | C31—C32—H32 | 120.4 |
N11—C12—H12A | 109.0 | C32—C33—C34 | 122.6 (3) |
C13—C12—H12A | 109.0 | C32—C33—N33 | 119.4 (3) |
N11—C12—H12B | 109.0 | C34—C33—N33 | 118.0 (3) |
C13—C12—H12B | 109.0 | C35—C34—C33 | 116.7 (3) |
H12A—C12—H12B | 107.8 | C35—C34—H34 | 121.6 |
N14—C13—C12 | 109.5 (2) | C33—C34—H34 | 121.6 |
N14—C13—H13A | 109.8 | C34—C35—C36 | 122.8 (3) |
C12—C13—H13A | 109.8 | C34—C35—N35 | 118.3 (3) |
N14—C13—H13B | 109.8 | C36—C35—N35 | 119.0 (3) |
C12—C13—H13B | 109.8 | C35—C36—C31 | 119.0 (3) |
H13A—C13—H13B | 108.2 | C35—C36—H36 | 120.5 |
C17—N14—C13 | 112.7 (2) | C31—C36—H36 | 120.5 |
C17—N14—C15 | 111.9 (2) | O31—C37—O32 | 126.1 (3) |
C13—N14—C15 | 109.5 (2) | O31—C37—C31 | 118.7 (3) |
C17—N14—H14 | 108.2 (16) | O32—C37—C31 | 115.2 (3) |
C13—N14—H14 | 108.3 (16) | C37—O32—H22A | 119.2 (14) |
C15—N14—H14 | 105.9 (15) | O34—N33—O33 | 124.1 (3) |
N14—C15—C16 | 111.3 (2) | O34—N33—C33 | 118.0 (3) |
N14—C15—H15A | 109.4 | O33—N33—C33 | 117.9 (3) |
C16—C15—H15A | 109.4 | O35—N35—O36 | 126.1 (11) |
N14—C15—H15B | 109.4 | O35—N35—C35 | 118.6 (11) |
C16—C15—H15B | 109.4 | O36—N35—C35 | 115.0 (7) |
C11A—C1—C2—C3 | −0.1 (5) | N14—C15—C16—N11 | 54.9 (3) |
C1—C2—C3—C4 | −2.2 (5) | C26—C21—C22—C23 | 1.2 (4) |
C2—C3—C4—C4A | 1.1 (5) | C27—C21—C22—C23 | −179.4 (2) |
C3—C4—C4A—C11A | 2.1 (4) | C21—C22—C23—C24 | −1.6 (4) |
C3—C4—C4A—N5 | −179.0 (3) | C21—C22—C23—N23 | 179.2 (2) |
C11A—C4A—N5—C5A | −56.2 (3) | C22—C23—C24—C25 | 0.8 (4) |
C4—C4A—N5—C5A | 125.0 (3) | N23—C23—C24—C25 | −179.9 (3) |
C4A—N5—C5A—C6 | −125.3 (3) | C23—C24—C25—C26 | 0.3 (4) |
C4A—N5—C5A—C9A | 59.5 (3) | C23—C24—C25—N25 | 179.0 (2) |
C9A—C5A—C6—C7 | 3.9 (4) | C22—C21—C26—C25 | −0.1 (4) |
N5—C5A—C6—C7 | −171.3 (2) | C27—C21—C26—C25 | −179.6 (2) |
C5A—C6—C7—C8 | −1.0 (4) | C24—C25—C26—C21 | −0.7 (4) |
C6—C7—C8—C9 | −2.5 (4) | N25—C25—C26—C21 | −179.4 (2) |
C6—C7—C8—Cl8 | 174.8 (2) | C26—C21—C27—O21 | −7.7 (4) |
C7—C8—C9—C9A | 3.2 (4) | C22—C21—C27—O21 | 172.9 (3) |
Cl8—C8—C9—C9A | −174.1 (2) | C26—C21—C27—O22 | 172.8 (2) |
C8—C9—C9A—C5A | −0.3 (4) | C22—C21—C27—O22 | −6.7 (4) |
C8—C9—C9A—N10 | 172.0 (2) | C24—C23—N23—O24 | −0.1 (4) |
C6—C5A—C9A—C9 | −3.2 (4) | C22—C23—N23—O24 | 179.2 (3) |
N5—C5A—C9A—C9 | 171.9 (2) | C24—C23—N23—O23 | 177.3 (3) |
C6—C5A—C9A—N10 | −174.5 (2) | C22—C23—N23—O23 | −3.4 (4) |
N5—C5A—C9A—N10 | 0.6 (4) | C24—C25—N25—O26 | 6.9 (4) |
C9—C9A—N10—C11 | 155.9 (2) | C26—C25—N25—O26 | −174.3 (3) |
C5A—C9A—N10—C11 | −32.5 (4) | C24—C25—N25—O25 | −173.5 (3) |
C9A—N10—C11—N11 | −174.9 (2) | C26—C25—N25—O25 | 5.3 (4) |
C9A—N10—C11—C11A | −4.2 (4) | C36—C31—C32—C33 | 0.8 (4) |
C2—C1—C11A—C4A | 3.3 (4) | C37—C31—C32—C33 | −175.0 (2) |
C2—C1—C11A—C11 | −175.9 (3) | C31—C32—C33—C34 | −0.5 (4) |
C4—C4A—C11A—C1 | −4.2 (4) | C31—C32—C33—N33 | 178.2 (2) |
N5—C4A—C11A—C1 | 176.9 (2) | C32—C33—C34—C35 | −0.3 (4) |
C4—C4A—C11A—C11 | 174.9 (2) | N33—C33—C34—C35 | −179.0 (3) |
N5—C4A—C11A—C11 | −3.9 (4) | C33—C34—C35—C36 | 0.8 (5) |
N10—C11—C11A—C1 | −141.2 (3) | C33—C34—C35—N35 | 179.4 (3) |
N11—C11—C11A—C1 | 29.6 (3) | C34—C35—C36—C31 | −0.4 (5) |
N10—C11—C11A—C4A | 39.7 (4) | N35—C35—C36—C31 | −179.1 (3) |
N11—C11—C11A—C4A | −149.5 (2) | C32—C31—C36—C35 | −0.4 (4) |
N10—C11—N11—C12 | 9.7 (4) | C37—C31—C36—C35 | 175.5 (3) |
C11A—C11—N11—C12 | −162.3 (2) | C32—C31—C37—O31 | 177.8 (3) |
N10—C11—N11—C16 | −136.6 (3) | C36—C31—C37—O31 | 1.9 (4) |
C11A—C11—N11—C16 | 51.4 (3) | C32—C31—C37—O32 | −0.2 (4) |
C11—N11—C12—C13 | −94.0 (3) | C36—C31—C37—O32 | −176.1 (3) |
C16—N11—C12—C13 | 55.2 (3) | C32—C33—N33—O34 | −173.7 (3) |
N11—C12—C13—N14 | −57.1 (3) | C34—C33—N33—O34 | 5.0 (4) |
C12—C13—N14—C17 | −177.7 (3) | C32—C33—N33—O33 | 5.9 (4) |
C12—C13—N14—C15 | 57.1 (3) | C34—C33—N33—O33 | −175.4 (3) |
C17—N14—C15—C16 | 177.5 (3) | C34—C35—N35—O35 | −15.5 (15) |
C13—N14—C15—C16 | −56.8 (3) | C36—C35—N35—O35 | 163.2 (15) |
C11—N11—C16—C15 | 95.5 (3) | C34—C35—N35—O36 | 158.5 (11) |
C12—N11—C16—C15 | −53.1 (3) | C36—C35—N35—O36 | −22.8 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5···O21 | 0.88 (3) | 2.23 (3) | 3.079 (3) | 162 (3) |
O22—H22A···O32 | 1.11 (4) | 1.35 (4) | 2.453 (3) | 169 (3) |
C4—H4···O21 | 0.93 | 2.48 | 3.280 (4) | 144 |
C13—H13A···O34 | 0.97 | 2.60 | 3.539 (4) | 164 |
N14—H14···O31i | 1.00 (3) | 1.70 (3) | 2.689 (3) | 169 (3) |
C1—H1···O35ii | 0.93 | 2.39 | 3.292 (13) | 164 |
C7—H7···O36iii | 0.93 | 2.34 | 3.242 (13) | 163 |
C7—H7···O46iii | 0.93 | 2.37 | 3.253 (14) | 159 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+1, −y+1, −z+1. |
Acknowledgements
Clozapine was a gift from R L Fine Chem, Bengaluru, Karnataka, India. MAES thanks the University of Mysore for research facilities.
Funding information
HSY is grateful to the UGC, New Delhi, for the award of a BSR Faculty Fellowship for three years.
References
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