research communications
The RS)-7-chloro-2-(2,5-dimethoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one: two hydrogen bonds generate an elegant three-dimensional framework structure
of (aDepartment of Studies in Organic Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, India, bDepartment of Physics, National Institute of Engineering, Mysore-570 008, India, cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, India, and dSchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UK
*Correspondence e-mail: yathirajan@hotmail.com
In the title compound, C61H15ClN2O3, the heterocyclic ring adopts an folded across the N⋯N line, with the 2,5-dimethoxyphenyl unit occupying a quasi-axial site. There are two N—H⋯O hydrogen bonds in the structure: one hydrogen bond links molecules related by a 41 screw axis to form a C(6) chain, and the other links inversion-related pairs of molecules to form an R22(8) ring. The ring motif links all of the chains into a continuous three-dimensional framework structure. Comparisons are made with the structures of some related compounds.
Keywords: heterocyclic compounds; reduced quinazolinones; crystal structure; molecular conformation; hydrogen bonding; supramolecular assembly.
CCDC reference: 1875494
1. Chemical context
Quinazoline-4-one and its derivatives constitute an important class of fused heterocycles, which are found in more than two hundred naturally occurring H)-one is a privileged scaffold in drug design (Badolato et al., 2018). Despite this, rather few structures have been published for compounds containing this heterocyclic nucleus (see Section 4 below), and with these considerations in mind, we now report the molecular and supramolecular structure of (RS)-7-chloro-2-(2,5-dimethoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (I) (Fig. 1). The compound was prepared using a recently published (Narasimhamurthy et al., 2014) one-step process, which employs a base-promoted reaction between a (dibromomethyl)arene, here 2-(dibromomethyl)-1,4-dimethoxybenzene, and a 2-aminobenzamide, here 2-amino-4-chlorobenzamide, which after a straightforward purification step gives the product (I) in 79% yield.
In addition, 2,3-dihydroquinazolin-4(12. Structural commentary
The molecule of compound (I) contains a stereogenic centre at atom C2, and the reference molecule was selected as one having the R configuration at this atom: the centrosymmetric confirms that compound (I) has crystallized as a The heterocyclic ring in compound (I) adopts a conformation close to the envelope form, in which this ring is folded across the line N1⋯N3 (Fig. 1). The ring-puckering parameters, calculated for the atom sequence (N1,C2,N3,C4,C4A,C8A) in the R-enantiomer are Q = 0.258 (2) Å, θ = 121.8 (4)° and φ = 219.3 (6)°. For the ideal envelope form, the puckering angles take the values θ = 54.7° (equivalent to 125.3°) and φ = (60k)°, where k represents an integer (Boeyens, 1978). The r.m.s. deviation of the atoms N1, N3, C4, C4A, C8A from their mean plane is only 0.035 Å, with a maximum deviation of 0.0403 (11) Å for atom N3. However, atom C2 is displaced from this plane by 0.355 (3) Å. The 2,5-dimethoxyphenyl substituent occupies the quasi-axial site at atom C2. Within this unit, the two methoxy C atoms are almost coplanar with the aryl ring: the deviations from the mean plane of this ring are 0.020 (5) Å for atom C221 and 0.101 (5) Å for atom C251. Associated with this planarity, the two exocyclic C—C—O angles at atoms C22 and C25 are significantly different, by 11.9° at C22 and by 8.2° at atoms C25, as previously observed in planar or near-planar alkoxyarenes (Seip & Seip, 1973; Ferguson et al., 1996).
3. Supramolecular features
The structure of compound (I) contains just two N—H⋯O hydrogen bonds (Table 1) but these are sufficient to link all of the molecules into a three-dimensional framework structure, whose formation is readily analysed in terms of the actions of the two individual hydrogen bonds. The hydrogen bond having atom N1 as the donor links molecules related by the 41 screw axis along (0.25, 0.5, z) into a C(6) chain (Etter, 1990; Etter et al., 1990; Bernstein et al., 1995) running parallel to the [001] direction (Fig. 2). Four chains of this type pass through each The hydrogen bond having atom N3 as the donor links inversion-related pairs of molecules to form a cyclic dimer characterized by an R22(8) motif (Fig. 3). This interaction directly links the C(6) chain around the 41 screw axis (, , z) with four similar chains around the screw axes along (, , z), (−, , z), (, 0, z) and (, 1, z) (Fig. 4). Propagation of these hydrogen bonds by the space-group symmetry operations links all of the C(6) chains, so linking all of the molecules into a very elegant three-dimensional structure generated by only two hydrogen bonds.
4. Database survey
It is of interest briefly to compare the molecular and supramolecular structure of (I) reported here with those of some related structures. In (RS)-2-(2-chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one (Li & Feng, 2009), the heterocyclic ring has a screw–boat conformation, as opposed to the envelope form in (I). As in (I), the structure contains two N—H⋯O hydrogen bonds, and these were described in the original report as generating a polymer along b, but without further specification. However, examination of the published atomic coordinates shows clearly that the molecules are linked into a chain of centrosymmetric, edge-fused rings running parallel to the [100] direction, in which R22(8) rings centred at (n, 1, 0) alternate with R42(12) rings centred at (n + , 1, 0), where n represents an integer in each case (Fig. 5).
In 5-chloro-3-hydroxy-2,2-dimethyl-2,3-dihydroquinazolin-4(1H)-one (Vembu et al., 2006), the heterocyclic ring again adopts the screw–boat conformation, and a combination of N—H⋯O and O—H⋯O hydrogen bonds links the molecules into complex sheets, within which rings of S(5), R22(4) and R22(10) types can be identified. There is no carbonyl group in (RS)-2-methyl-4-phenyl-3,4-dihydroquinazoline, and here molecules which are related by a 31 screw axis are linked by an N-–H⋯N hydrogen bond to form a C(5) chain (Valkonen et al., 2011).
Finally, we note the structures of a number of 2,3-dihydroquinazolin-4(1H)-ones in which there is a substituent at atom N3 (Butcher et al., 2007; Toze et al., 2018; Zaytsev et al., 2018). In each of these examples, the molecules are linked by a single N—H⋯O hydrogen bond to form a C(6) chain. However, when the substituent at atom N3 is an arylmethylamino group, the heterocyclic ring adopts a screw–boat conformation (Butcher et al., 2007), but in five examples where this substituent is either a benzyl group or a furanylmethyl unit, the heterocyclic ring adopts an folded across the N⋯N line (Toze et al., 2018; Zaytsev et al. 2018).
5. Synthesis and crystallization
A sample of compound (I) was prepared using a recently published general procedure (Narasimhamurthy et al., 2014). Potassium tert-butoxide (3.3 mmol) was added to a suspension of 2-(dibromomethyl)-1,4-dimethoxybenzene (3.3 mmol) and 2-amino-4-chlorobenzamide (3.5 mmol) in a pyridine-dimethylformamide mixture (3:1, v/v). The resulting mixture was heated at 313 K for 4 h, with TLC monitoring. When the reaction was judged to be complete, an excess of water was added, followed by extraction with ethyl acetate (2 × 20 ml). The combined organic extract was washed with brine and then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the crude product was purified by using silica gel mesh 60–120, with 30% ethyl acetate in hexane as to give the product (I) in 79% yield. Crystals suitable for single crystal X-ray diffraction were grown by slow evaporation, at ambient temperature and in the presence of air, of a solution in dimethylsulfoxide: m.p. 481–483 K.
6. Refinement
Crystal data, data collection and structure . In the setting of I41/a, No. 88, employed here the origin is located at a centre of inversion. All H atoms were located in difference maps. The H atoms bonded to C atoms were then treated as riding atoms in geometrically idealized position with C—H 0.93 Å (aromatic), 0.96 Å (CH3) or 0.98 Å (aliphatic C—H), and with Uiso(H) = kUeq(C), where k = 1.5 for the methyl groups, which were permitted to rotate but not to tilt, and 1.2 for all other H atoms bonded to C atoms. For the H atoms bonded to N atoms, the atomic coordinates were refined with Uiso(H) = 1.2Ueq(N), giving the N—H distances shown in Table 1.
details are given in Table 2Supporting information
CCDC reference: 1875494
https://doi.org/10.1107/S2056989019007023/zl2756sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019007023/zl2756Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989019007023/zl2756Isup3.cml
Data collection: APEX2 (Bruker, 2015); cell
SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).C16H15ClN2O3 | Dx = 1.403 Mg m−3 |
Mr = 318.75 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, I41/a | Cell parameters from 3465 reflections |
a = 15.314 (7) Å | θ = 1.6–27.6° |
c = 25.736 (12) Å | µ = 0.27 mm−1 |
V = 6036 (6) Å3 | T = 296 K |
Z = 16 | Block, colourless |
F(000) = 2656 | 0.26 × 0.22 × 0.18 mm |
Bruker APEXII CCD diffractometer | 3149 independent reflections |
Radiation source: fine focus sealed tube | 1848 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.072 |
Detector resolution: 0.3333 pixels mm-1 | θmax = 26.6°, θmin = 1.6° |
φ and ω scans | h = −19→19 |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | k = −19→19 |
Tmin = 0.913, Tmax = 0.953 | l = −32→26 |
42994 measured reflections |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.128 | w = 1/[σ2(Fo2) + (0.0505P)2 + 3.5139P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3149 reflections | Δρmax = 0.17 e Å−3 |
207 parameters | Δρmin = −0.27 e Å−3 |
0 restraints |
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 | ||
N1 | 0.30909 (14) | 0.40264 (14) | 0.37953 (7) | 0.0531 (6) | |
H1 | 0.3275 (17) | 0.4092 (16) | 0.4083 (10) | 0.064* | |
C2 | 0.30616 (16) | 0.31258 (15) | 0.36210 (8) | 0.0482 (6) | |
H2 | 0.3646 | 0.2879 | 0.3670 | 0.058* | |
N3 | 0.28752 (14) | 0.31121 (14) | 0.30684 (7) | 0.0506 (5) | |
H3 | 0.2932 (16) | 0.2628 (17) | 0.2929 (9) | 0.061* | |
C4 | 0.24435 (15) | 0.37295 (16) | 0.28060 (8) | 0.0467 (6) | |
O4 | 0.22338 (12) | 0.36121 (11) | 0.23471 (6) | 0.0603 (5) | |
C4A | 0.22505 (14) | 0.45429 (15) | 0.30792 (8) | 0.0434 (5) | |
C5 | 0.17657 (16) | 0.51985 (16) | 0.28452 (9) | 0.0521 (6) | |
H5 | 0.1566 | 0.5118 | 0.2507 | 0.062* | |
C6 | 0.15743 (16) | 0.59599 (17) | 0.30984 (9) | 0.0569 (7) | |
H6 | 0.1250 | 0.6397 | 0.2939 | 0.068* | |
C7 | 0.18794 (16) | 0.60558 (16) | 0.35987 (9) | 0.0556 (6) | |
Cl7 | 0.16054 (6) | 0.70075 (5) | 0.39245 (3) | 0.0873 (3) | |
C8 | 0.23775 (16) | 0.54326 (16) | 0.38428 (9) | 0.0522 (6) | |
H8 | 0.2583 | 0.5527 | 0.4178 | 0.063* | |
C8A | 0.25726 (14) | 0.46570 (15) | 0.35832 (8) | 0.0424 (5) | |
C21 | 0.24297 (15) | 0.25723 (14) | 0.39324 (8) | 0.0432 (5) | |
C22 | 0.26659 (17) | 0.23605 (16) | 0.44405 (8) | 0.0522 (6) | |
C23 | 0.2110 (2) | 0.18716 (17) | 0.47413 (9) | 0.0678 (8) | |
H23 | 0.2271 | 0.1735 | 0.5080 | 0.081* | |
C24 | 0.1321 (2) | 0.15794 (18) | 0.45543 (10) | 0.0682 (8) | |
H24 | 0.0951 | 0.1257 | 0.4767 | 0.082* | |
C25 | 0.10822 (18) | 0.17630 (16) | 0.40582 (9) | 0.0559 (7) | |
C26 | 0.16454 (16) | 0.22579 (15) | 0.37492 (8) | 0.0488 (6) | |
H26 | 0.1485 | 0.2379 | 0.3408 | 0.059* | |
O221 | 0.34622 (12) | 0.26875 (12) | 0.45915 (6) | 0.0718 (6) | |
C221 | 0.3739 (2) | 0.2493 (2) | 0.51083 (11) | 0.0918 (11) | |
H22A | 0.3823 | 0.1874 | 0.5143 | 0.138* | |
H22B | 0.3302 | 0.2684 | 0.5350 | 0.138* | |
H22C | 0.4279 | 0.2789 | 0.5179 | 0.138* | |
O251 | 0.03307 (13) | 0.14750 (13) | 0.38268 (8) | 0.0767 (6) | |
C251 | −0.0300 (2) | 0.1052 (2) | 0.41418 (14) | 0.0939 (11) | |
H25A | −0.0488 | 0.1442 | 0.4412 | 0.141* | |
H25B | −0.0048 | 0.0539 | 0.4294 | 0.141* | |
H25C | −0.0793 | 0.0889 | 0.3932 | 0.141* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0655 (14) | 0.0565 (13) | 0.0373 (10) | −0.0097 (11) | −0.0105 (10) | −0.0042 (10) |
C2 | 0.0520 (14) | 0.0582 (15) | 0.0343 (12) | 0.0045 (12) | −0.0054 (10) | −0.0063 (10) |
N3 | 0.0645 (14) | 0.0545 (13) | 0.0328 (10) | 0.0040 (11) | 0.0019 (9) | −0.0061 (9) |
C4 | 0.0508 (14) | 0.0574 (15) | 0.0321 (11) | −0.0045 (12) | 0.0049 (10) | −0.0021 (11) |
O4 | 0.0872 (13) | 0.0620 (11) | 0.0316 (8) | 0.0061 (9) | −0.0056 (8) | −0.0085 (7) |
C4A | 0.0427 (13) | 0.0524 (14) | 0.0351 (11) | −0.0070 (11) | 0.0026 (10) | −0.0054 (10) |
C5 | 0.0539 (15) | 0.0618 (16) | 0.0404 (12) | −0.0005 (13) | −0.0050 (11) | −0.0082 (11) |
C6 | 0.0585 (16) | 0.0595 (17) | 0.0528 (14) | 0.0039 (13) | −0.0050 (12) | −0.0054 (12) |
C7 | 0.0568 (16) | 0.0551 (16) | 0.0548 (14) | −0.0041 (13) | 0.0012 (12) | −0.0154 (12) |
Cl7 | 0.1085 (7) | 0.0736 (5) | 0.0800 (5) | 0.0165 (4) | −0.0147 (4) | −0.0338 (4) |
C8 | 0.0580 (16) | 0.0593 (16) | 0.0395 (12) | −0.0130 (13) | −0.0033 (11) | −0.0104 (11) |
C8A | 0.0404 (13) | 0.0508 (14) | 0.0359 (11) | −0.0119 (11) | 0.0002 (10) | −0.0033 (10) |
C21 | 0.0560 (15) | 0.0410 (13) | 0.0326 (11) | 0.0068 (11) | −0.0025 (10) | −0.0045 (9) |
C22 | 0.0692 (17) | 0.0490 (15) | 0.0384 (12) | 0.0063 (13) | −0.0121 (12) | −0.0073 (11) |
C23 | 0.109 (2) | 0.0588 (17) | 0.0354 (13) | 0.0081 (17) | −0.0032 (14) | 0.0095 (12) |
C24 | 0.088 (2) | 0.0621 (18) | 0.0540 (16) | −0.0059 (16) | 0.0068 (15) | 0.0091 (13) |
C25 | 0.0707 (18) | 0.0458 (14) | 0.0514 (14) | 0.0010 (13) | 0.0006 (13) | −0.0025 (11) |
C26 | 0.0612 (16) | 0.0484 (14) | 0.0369 (11) | 0.0042 (12) | −0.0039 (11) | 0.0006 (10) |
O221 | 0.0866 (14) | 0.0768 (13) | 0.0521 (11) | 0.0029 (11) | −0.0292 (10) | −0.0026 (9) |
C221 | 0.124 (3) | 0.091 (2) | 0.0607 (17) | 0.024 (2) | −0.0496 (18) | −0.0082 (16) |
O251 | 0.0707 (13) | 0.0784 (14) | 0.0810 (13) | −0.0176 (11) | −0.0024 (11) | 0.0074 (11) |
C251 | 0.072 (2) | 0.082 (2) | 0.128 (3) | −0.0106 (17) | 0.012 (2) | 0.026 (2) |
N1—C8A | 1.364 (3) | C21—C26 | 1.377 (3) |
N1—C2 | 1.451 (3) | C21—C22 | 1.395 (3) |
N1—H1 | 0.80 (3) | C22—C23 | 1.373 (4) |
C2—N3 | 1.451 (3) | C22—O221 | 1.374 (3) |
C2—C21 | 1.516 (3) | C23—C24 | 1.376 (4) |
C2—H2 | 0.9800 | C23—H23 | 0.9300 |
N3—C4 | 1.337 (3) | C24—C25 | 1.357 (3) |
N3—H3 | 0.83 (2) | C24—H24 | 0.9300 |
C4—O4 | 1.237 (3) | C25—O251 | 1.369 (3) |
C4—C4A | 1.461 (3) | C25—C26 | 1.397 (3) |
C4A—C5 | 1.386 (3) | C26—H26 | 0.9300 |
C4A—C8A | 1.399 (3) | O221—C221 | 1.427 (3) |
C5—C6 | 1.368 (3) | C221—H22A | 0.9600 |
C5—H5 | 0.9300 | C221—H22B | 0.9600 |
C6—C7 | 1.377 (3) | C221—H22C | 0.9600 |
C6—H6 | 0.9300 | O251—C251 | 1.418 (3) |
C7—C8 | 1.374 (3) | C251—H25A | 0.9600 |
C7—Cl7 | 1.733 (3) | C251—H25B | 0.9600 |
C8—C8A | 1.395 (3) | C251—H25C | 0.9600 |
C8—H8 | 0.9300 | ||
C8A—N1—C2 | 122.09 (19) | C26—C21—C22 | 117.8 (2) |
C8A—N1—H1 | 119.2 (19) | C26—C21—C2 | 124.84 (19) |
C2—N1—H1 | 114.6 (19) | C22—C21—C2 | 117.4 (2) |
N3—C2—N1 | 108.84 (19) | C23—C22—O221 | 126.1 (2) |
N3—C2—C21 | 112.62 (19) | C23—C22—C21 | 119.6 (2) |
N1—C2—C21 | 112.82 (18) | O221—C22—C21 | 114.2 (2) |
N3—C2—H2 | 107.4 | C22—C23—C24 | 121.7 (2) |
N1—C2—H2 | 107.4 | C22—C23—H23 | 119.2 |
C21—C2—H2 | 107.4 | C24—C23—H23 | 119.2 |
C4—N3—C2 | 125.6 (2) | C25—C24—C23 | 119.9 (3) |
C4—N3—H3 | 117.8 (17) | C25—C24—H24 | 120.1 |
C2—N3—H3 | 114.6 (17) | C23—C24—H24 | 120.1 |
O4—C4—N3 | 120.5 (2) | C24—C25—O251 | 124.7 (2) |
O4—C4—C4A | 122.1 (2) | C24—C25—C26 | 118.8 (3) |
N3—C4—C4A | 117.39 (19) | O251—C25—C26 | 116.5 (2) |
C5—C4A—C8A | 120.1 (2) | C21—C26—C25 | 122.2 (2) |
C5—C4A—C4 | 121.12 (19) | C21—C26—H26 | 118.9 |
C8A—C4A—C4 | 118.8 (2) | C25—C26—H26 | 118.9 |
C6—C5—C4A | 121.7 (2) | C22—O221—C221 | 116.8 (2) |
C6—C5—H5 | 119.2 | O221—C221—H22A | 109.5 |
C4A—C5—H5 | 119.2 | O221—C221—H22B | 109.5 |
C5—C6—C7 | 117.6 (2) | H22A—C221—H22B | 109.5 |
C5—C6—H6 | 121.2 | O221—C221—H22C | 109.5 |
C7—C6—H6 | 121.2 | H22A—C221—H22C | 109.5 |
C8—C7—C6 | 122.8 (2) | H22B—C221—H22C | 109.5 |
C8—C7—Cl7 | 119.83 (19) | C25—O251—C251 | 118.1 (2) |
C6—C7—Cl7 | 117.4 (2) | O251—C251—H25A | 109.5 |
C7—C8—C8A | 119.4 (2) | O251—C251—H25B | 109.5 |
C7—C8—H8 | 120.3 | H25A—C251—H25B | 109.5 |
C8A—C8—H8 | 120.3 | O251—C251—H25C | 109.5 |
N1—C8A—C8 | 122.4 (2) | H25A—C251—H25C | 109.5 |
N1—C8A—C4A | 119.2 (2) | H25B—C251—H25C | 109.5 |
C8—C8A—C4A | 118.4 (2) | ||
C8A—N1—C2—N3 | 33.6 (3) | C5—C4A—C8A—C8 | 1.3 (3) |
C8A—N1—C2—C21 | −92.2 (2) | C4—C4A—C8A—C8 | −179.4 (2) |
N1—C2—N3—C4 | −26.5 (3) | N3—C2—C21—C26 | −14.9 (3) |
C21—C2—N3—C4 | 99.4 (3) | N1—C2—C21—C26 | 108.8 (2) |
C2—N3—C4—O4 | −171.9 (2) | N3—C2—C21—C22 | 164.5 (2) |
C2—N3—C4—C4A | 9.3 (3) | N1—C2—C21—C22 | −71.8 (3) |
O4—C4—C4A—C5 | 4.7 (3) | C26—C21—C22—C23 | −1.5 (3) |
N3—C4—C4A—C5 | −176.6 (2) | C2—C21—C22—C23 | 179.0 (2) |
O4—C4—C4A—C8A | −174.6 (2) | C26—C21—C22—O221 | 179.1 (2) |
N3—C4—C4A—C8A | 4.1 (3) | C2—C21—C22—O221 | −0.4 (3) |
C8A—C4A—C5—C6 | −1.3 (4) | O221—C22—C23—C24 | 179.5 (2) |
C4—C4A—C5—C6 | 179.4 (2) | C21—C22—C23—C24 | 0.2 (4) |
C4A—C5—C6—C7 | −0.1 (4) | C22—C23—C24—C25 | 1.0 (4) |
C5—C6—C7—C8 | 1.5 (4) | C23—C24—C25—O251 | 177.2 (2) |
C5—C6—C7—Cl7 | −178.02 (19) | C23—C24—C25—C26 | −0.8 (4) |
C6—C7—C8—C8A | −1.5 (4) | C22—C21—C26—C25 | 1.8 (3) |
Cl7—C7—C8—C8A | 178.07 (18) | C2—C21—C26—C25 | −178.8 (2) |
C2—N1—C8A—C8 | 158.6 (2) | C24—C25—C26—C21 | −0.6 (4) |
C2—N1—C8A—C4A | −24.0 (3) | O251—C25—C26—C21 | −178.8 (2) |
C7—C8—C8A—N1 | 177.4 (2) | C23—C22—O221—C221 | 0.6 (4) |
C7—C8—C8A—C4A | 0.0 (3) | C21—C22—O221—C221 | 179.9 (2) |
C5—C4A—C8A—N1 | −176.2 (2) | C24—C25—O251—C251 | 8.7 (4) |
C4—C4A—C8A—N1 | 3.1 (3) | C26—C25—O251—C251 | −173.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4i | 0.80 (3) | 2.39 (3) | 3.161 (3) | 162 (2) |
N3—H3···O4ii | 0.83 (3) | 2.04 (3) | 2.854 (3) | 166 (2) |
Symmetry codes: (i) −y+3/4, x+1/4, z+1/4; (ii) −x+1/2, −y+1/2, −z+1/2. |
Acknowledgements
KHN is grateful to UGC, RFSMS, Government of India for a Research Fellowship. BKS thanks the University of Mysore, for research facilities.
Funding information
KSR and HSY are grateful to UGC, New Delhi, for the award of a BSR Faculty Fellowship for a period of three years.
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