research communications
N′-(4-hydroxybenzylidene)-3-(thiophen-2-yl)prop-2-enohydrazide
of 2-benzoylamino-aDepartment of Chemistry, Mangalore University, Mangalagangothri 574 199, DK, Mangalore, India, bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India, cDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, dDepartment of Bioinformatics, Central University of South Bihar, BIT Campus, PO B. V. College, Patna 800 014, India, and eSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
*Correspondence e-mail: yathirajan@hotmail.com
In the title compound, C21H17N3O3S, the non-H atoms, apart from those in the benzoyl group, are almost coplanar (r.m.s. deviation = 0.049 Å) and the benzoyl group is almost orthogonal to the plane of the rest of the molecule [dihedral angle = 80.34 (6)°]. In the crystal, a combination of N—H⋯O and asymmetric bifurcated O—H⋯(N,O) hydrogen bonds link the molecules into a three-dimensional network. Weak C—H⋯O interactions are also observed.
CCDC reference: 1491115
1. Chemical context
Compounds containing hydrazide and Schiff base functionality are of interest as examples of this class have been shown to exhibit antifungal (Singh & Dash, 1988), anti-inflammatory (Todeschini et al., 1998), antimicrobial (Pandeya et al., 1999) and antitumour activity (Desai et al., 2001).
We report here the (Fig. 1), which we compare with the closely related compound methyl 2-benzoylamino-3-(thiophen-2-yl)prop-2-enoate, (II) (Subbulakshmi et al., 2015). The constitutions of compounds (I) and (II) differ simply in the notional replacement of the COOMe unit in (II) by the CONHN=CHC6H4OH group in (I). Compound (I) was prepared by condensation of 2-benzoylamino-3-(thiophen-2-yl)prop-2-enoylhydrazine with 4-hydroxybenzaldehyde, whereas compound (II) was prepared by the hydrolytic ring-opening of 2-phenyl-4-[(thiophen-2-yl)-methylidene]-1,3-oxazol-5(4H)-one to form 2-(benzoylamino)-3-(thiophen-2-yl)prop-2-enoic acid, followed by esterification.
of the title compound, (I)2. Structural commentary
The central core of the molecule of (I), encompassing atoms N21, C3, C2, C1, N11, N12, C17 and C11, is roughly planar: the maximum deviation of any of the component atoms from the mean plane is 0.0859 (14) Å with an r.m.s. deviation of 0.049 Å. The thienyl ring and the aryl ring (C11–C16) are both nearly coplanar with the central spacer unit, making dihedral angles of 1.60 (12) and 5.35 (11)°, respectively. By contrast, the aryl ring (C21–C26) is almost orthogonal to the central unit, making a dihedral angle of 80.34 (6)°. The molecules of (I) exhibit no internal symmetry and they are thus conformationally chiral: the centrosymmetric confirms that compound (I) crystallizes as a conformational racemate. The bond distances show clearly that the bonds C2—C3 and N12—C17 are localized double bonds, consistent with the location of the H atoms as deduced from difference maps, ruling out the occurrence in the crystal of any other tautomeric forms. The non-bonded intramolecular distance O1⋯O27, 3.820 (3) Å, rules out any possibility of an intramolecular O—H⋯O hydrogen bond.
3. Supramolecular interactions
In the crystal, the molecules of (I) are linked into a three-dimensional network by a combination of two N—H⋯O hydrogen bonds and a three-centre (bifurcated) O—H⋯(N,O) hydrogen bond (Table 1). The three-centre interaction is planar within experimental uncertainty with both acceptors in the same molecule, and it is markedly asymmetric. While the longer component might, perhaps, be regarded as an adventitious contact given the proximity of the two acceptor sites, the great propensity of hydroxyl groups to act as hydrogen-bond donors (Desiraju & Steiner, 1999) cautions against this interpretation. Very asymmetric three-centre hydrogen bonds are, in fact, not uncommon: for example, in the structure of 2-amino-4,6-dimethoxy-5-nitrosopyrimidine–water (4/3) (Glidewell et al., 2002) there are six different three-centre hydrogen bonds, two of which, both of O—H⋯(N,O) type, show asymmetries comparable with that found here in (I); markedly asymmetric N—H⋯(N,O) systems occur in the structures of 2-amino-4,6-bis(benzyloxy)-5-nitrosopyrimidine (Quesada et al., 2002), and in (E)-3-dimethylamino-2-(1H-indol-3-ylcarbonyl)acrylonitrile, where the two acceptors form parts of different molecules (Galvez et al., 2008); and a very asymmetric N—H⋯(O)2 hydrogen bond having the two acceptors in different molecules occurs in the structure of 3,3-difluoro-5-nitro-1H-indol-2(3H)-one (Glidewell et al., 2005).
The formation of the hydrogen-bonded network in (I) is most readily analysed in terms of simpler substructures of lower dimensionality (Ferguson et al., 1998a,b; Gregson et al., 2000). In the simplest of the substructures, molecules related by a 21 screw axis are linked by the three-centre hydrogen bond to form a C(8)C(11)[R12(5)] chain of rings running parallel to the [010] direction (Fig. 2). The chains of this type are linked by the N—H⋯O hydrogen bond having atom O1 as the acceptor (Table 1) to form a two-dimensional in the form of a sheet lying parallel to (001) (Fig. 3). Finally, these sheets are linked by the N—H⋯O hydrogen bond having atom O27 as the acceptor to form a continuous framework structure (Fig. 4). This network is reinforced by a number of weak C—H⋯O interactions (Table 1), but these are not essential to its formation.
4. Database survey
In the et al., 2015), a combination of N—H⋯O and C—H⋯π(arene) hydrogen bonds links the molecules into sheets; in the structure of (E)-N′-[1-(2-hydroxyphenyl)ethylidene]-3-methoxybenzohydrazide the molecules are linked by a single N—H⋯O hydrogen bond to form simple C(4) chains (Li & Ban, 2009); and the molecules of (E)-N′-(4-hydroxybenzylidene)-3-nitrobenzohydrazide are linked into sheets by a combination of N—H⋯O, O—H⋯·(N,O) and C—H⋯O hydrogen bonds (Meng et al., 2012).
of compound (II) (Subbulakshmi5. Synthesis and crystallization
A mixture of 2-benzoylamino-3-(thiophen-2-yl)prop-2-enoylhydrazine (2.87 g, 0.01 mol), and 4-hydroxybenzaldehyde (1.22 g, 0.01 mol) in ethanol (20 ml) was stirred at ambient temperature for 4 h. The resulting solid product was collected by filtration, washed with cold water, dried in air and recrystallized from ethanol solution: m.p. 534–535 K. Crystals of (I) were grown by slow evaporation at room temperature of a solution in 1,4-dioxane-methanol (1:1, v/v).
6. Refinement
Crystal data, data collection and structure . 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 = 0.93 Å and with Uiso(H) = 1.2 Ueq(C). For the H atoms bonded to O or N atoms, the atomic coordinates were refined with Uiso(H) = 1.2 Ueq(N) or 1.5Ueq(O), giving the O—H and N—H distances shown in Table 1.
details are summarized in Table 2
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Supporting information
CCDC reference: 1491115
https://doi.org/10.1107/S2056989016010975/hb7597sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016010975/hb7597Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989016010975/hb7597Isup3.cml
Data collection: CrysAlis PRO (Agilent, 2014); cell
CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009).C21H17N3O3S | F(000) = 1632 |
Mr = 391.43 | Dx = 1.357 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 22.5212 (7) Å | Cell parameters from 6327 reflections |
b = 10.1879 (4) Å | θ = 3.4–32.0° |
c = 17.3592 (5) Å | µ = 0.20 mm−1 |
β = 105.801 (3)° | T = 298 K |
V = 3832.5 (2) Å3 | Plate, colourless |
Z = 8 | 0.42 × 0.32 × 0.18 mm |
Agilent Xcalibur Eos Gemini diffractometer | 3426 reflections with I > 2σ(I) |
Detector resolution: 16.0416 pixels mm-1 | Rint = 0.024 |
φ and ω scans | θmax = 27.6°, θmin = 3.4° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −25→29 |
Tmin = 0.757, Tmax = 0.965 | k = −13→7 |
9963 measured reflections | l = −20→22 |
4419 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0475P)2 + 2.5641P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
4419 reflections | Δρmax = 0.24 e Å−3 |
262 parameters | Δρmin = −0.26 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 | ||
C1 | 0.53659 (7) | 0.43211 (16) | 0.64694 (9) | 0.0306 (3) | |
O1 | 0.56722 (5) | 0.47222 (13) | 0.71288 (7) | 0.0423 (3) | |
C2 | 0.47457 (7) | 0.48794 (16) | 0.60847 (9) | 0.0299 (3) | |
C3 | 0.43369 (7) | 0.43455 (17) | 0.54526 (9) | 0.0347 (4) | |
H3 | 0.4469 | 0.3586 | 0.5252 | 0.042* | |
N11 | 0.55560 (6) | 0.33591 (15) | 0.60668 (8) | 0.0348 (3) | |
H11 | 0.5363 (9) | 0.3157 (19) | 0.5583 (12) | 0.042* | |
N12 | 0.61135 (6) | 0.27363 (15) | 0.63980 (8) | 0.0350 (3) | |
C17 | 0.62189 (8) | 0.17766 (18) | 0.59827 (10) | 0.0372 (4) | |
H17 | 0.5924 | 0.1570 | 0.5509 | 0.045* | |
C11 | 0.67784 (7) | 0.09896 (17) | 0.62156 (10) | 0.0349 (4) | |
C12 | 0.72750 (8) | 0.13084 (18) | 0.68643 (10) | 0.0382 (4) | |
H12 | 0.7261 | 0.2068 | 0.7156 | 0.046* | |
C13 | 0.77876 (8) | 0.05097 (19) | 0.70785 (10) | 0.0393 (4) | |
H13 | 0.8115 | 0.0730 | 0.7515 | 0.047* | |
C14 | 0.78174 (8) | −0.06236 (18) | 0.66441 (10) | 0.0373 (4) | |
O14 | 0.83122 (6) | −0.14325 (14) | 0.68163 (9) | 0.0524 (4) | |
H14 | 0.8583 (12) | −0.115 (3) | 0.7211 (15) | 0.079* | |
C15 | 0.73300 (8) | −0.09439 (18) | 0.59955 (11) | 0.0436 (4) | |
H15 | 0.7346 | −0.1700 | 0.5701 | 0.052* | |
C16 | 0.68189 (8) | −0.01392 (19) | 0.57854 (10) | 0.0421 (4) | |
H16 | 0.6494 | −0.0358 | 0.5345 | 0.050* | |
N21 | 0.45947 (6) | 0.60302 (14) | 0.64533 (8) | 0.0326 (3) | |
H21 | 0.4510 (9) | 0.5932 (19) | 0.6884 (11) | 0.039* | |
C27 | 0.46800 (7) | 0.72320 (17) | 0.61800 (9) | 0.0314 (3) | |
O27 | 0.49198 (6) | 0.73798 (13) | 0.56269 (7) | 0.0435 (3) | |
C21 | 0.44374 (8) | 0.83722 (17) | 0.65374 (9) | 0.0360 (4) | |
C22 | 0.40355 (9) | 0.8231 (2) | 0.70116 (12) | 0.0497 (5) | |
H22 | 0.3933 | 0.7395 | 0.7149 | 0.060* | |
C23 | 0.37867 (11) | 0.9317 (3) | 0.72807 (14) | 0.0642 (6) | |
H23 | 0.3519 | 0.9210 | 0.7600 | 0.077* | |
C24 | 0.39294 (12) | 1.0539 (2) | 0.70834 (14) | 0.0676 (7) | |
H24 | 0.3756 | 1.1267 | 0.7263 | 0.081* | |
C25 | 0.43304 (14) | 1.0707 (2) | 0.66171 (15) | 0.0737 (7) | |
H25 | 0.4430 | 1.1548 | 0.6485 | 0.088* | |
C26 | 0.45857 (11) | 0.9615 (2) | 0.63441 (12) | 0.0551 (5) | |
H26 | 0.4857 | 0.9727 | 0.6030 | 0.066* | |
S31 | 0.33408 (2) | 0.61148 (5) | 0.52709 (3) | 0.04314 (14) | |
C32 | 0.37235 (8) | 0.47716 (18) | 0.50374 (10) | 0.0367 (4) | |
C33 | 0.33582 (9) | 0.4137 (2) | 0.43779 (12) | 0.0518 (5) | |
H33 | 0.3482 | 0.3392 | 0.4153 | 0.062* | |
C34 | 0.27760 (9) | 0.4737 (3) | 0.40789 (12) | 0.0597 (6) | |
H34 | 0.2473 | 0.4425 | 0.3640 | 0.072* | |
C35 | 0.27068 (9) | 0.5808 (2) | 0.44974 (12) | 0.0533 (5) | |
H35 | 0.2353 | 0.6323 | 0.4378 | 0.064* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0294 (8) | 0.0327 (8) | 0.0303 (7) | 0.0004 (6) | 0.0090 (6) | 0.0012 (6) |
O1 | 0.0340 (6) | 0.0506 (8) | 0.0378 (6) | 0.0050 (5) | 0.0019 (5) | −0.0115 (6) |
C2 | 0.0310 (8) | 0.0298 (8) | 0.0301 (7) | 0.0047 (6) | 0.0107 (6) | 0.0002 (6) |
C3 | 0.0330 (8) | 0.0346 (9) | 0.0370 (8) | 0.0039 (7) | 0.0103 (7) | −0.0042 (7) |
N11 | 0.0316 (7) | 0.0407 (8) | 0.0293 (6) | 0.0108 (6) | 0.0037 (6) | −0.0008 (6) |
N12 | 0.0307 (7) | 0.0406 (8) | 0.0335 (7) | 0.0096 (6) | 0.0086 (6) | 0.0043 (6) |
C17 | 0.0346 (8) | 0.0429 (10) | 0.0323 (8) | 0.0077 (7) | 0.0062 (7) | 0.0036 (7) |
C11 | 0.0338 (8) | 0.0383 (9) | 0.0330 (8) | 0.0069 (7) | 0.0097 (7) | 0.0043 (7) |
C12 | 0.0378 (9) | 0.0399 (10) | 0.0368 (8) | 0.0055 (7) | 0.0103 (7) | −0.0036 (7) |
C13 | 0.0332 (8) | 0.0485 (11) | 0.0335 (8) | 0.0033 (8) | 0.0047 (7) | 0.0003 (8) |
C14 | 0.0337 (8) | 0.0367 (9) | 0.0401 (9) | 0.0080 (7) | 0.0078 (7) | 0.0092 (7) |
O14 | 0.0425 (7) | 0.0490 (8) | 0.0558 (8) | 0.0182 (6) | −0.0034 (6) | −0.0021 (7) |
C15 | 0.0417 (10) | 0.0354 (10) | 0.0488 (10) | 0.0076 (8) | 0.0043 (8) | −0.0061 (8) |
C16 | 0.0360 (9) | 0.0439 (11) | 0.0402 (9) | 0.0058 (8) | 0.0000 (7) | −0.0040 (8) |
N21 | 0.0376 (7) | 0.0343 (8) | 0.0279 (6) | 0.0073 (6) | 0.0123 (6) | −0.0011 (6) |
C27 | 0.0296 (8) | 0.0349 (9) | 0.0266 (7) | 0.0033 (6) | 0.0023 (6) | −0.0035 (6) |
O27 | 0.0537 (8) | 0.0439 (8) | 0.0375 (6) | −0.0012 (6) | 0.0203 (6) | −0.0028 (5) |
C21 | 0.0363 (9) | 0.0357 (9) | 0.0305 (8) | 0.0061 (7) | −0.0002 (7) | −0.0061 (7) |
C22 | 0.0499 (11) | 0.0483 (12) | 0.0534 (11) | 0.0079 (9) | 0.0185 (9) | −0.0102 (9) |
C23 | 0.0613 (14) | 0.0656 (16) | 0.0688 (14) | 0.0177 (12) | 0.0231 (11) | −0.0200 (12) |
C24 | 0.0798 (17) | 0.0531 (14) | 0.0641 (14) | 0.0248 (12) | 0.0095 (12) | −0.0189 (11) |
C25 | 0.108 (2) | 0.0359 (12) | 0.0719 (15) | 0.0058 (13) | 0.0156 (15) | −0.0041 (11) |
C26 | 0.0741 (15) | 0.0385 (11) | 0.0527 (11) | 0.0012 (10) | 0.0175 (11) | −0.0040 (9) |
S31 | 0.0342 (2) | 0.0489 (3) | 0.0449 (3) | 0.00813 (19) | 0.00828 (18) | −0.0011 (2) |
C32 | 0.0326 (8) | 0.0431 (10) | 0.0338 (8) | 0.0015 (7) | 0.0080 (7) | −0.0027 (7) |
C33 | 0.0381 (10) | 0.0649 (14) | 0.0475 (10) | 0.0022 (9) | 0.0034 (8) | −0.0158 (9) |
C34 | 0.0363 (10) | 0.0921 (18) | 0.0430 (10) | 0.0006 (11) | −0.0025 (8) | −0.0101 (11) |
C35 | 0.0328 (9) | 0.0762 (15) | 0.0471 (11) | 0.0103 (9) | 0.0047 (8) | 0.0074 (10) |
C1—O1 | 1.2342 (19) | N21—C27 | 1.346 (2) |
C1—N11 | 1.340 (2) | N21—H21 | 0.826 (19) |
C1—C2 | 1.487 (2) | C27—O27 | 1.2322 (19) |
C2—C3 | 1.341 (2) | C27—C21 | 1.489 (2) |
C2—N21 | 1.421 (2) | C21—C26 | 1.374 (3) |
C3—C32 | 1.440 (2) | C21—C22 | 1.387 (3) |
C3—H3 | 0.9300 | C22—C23 | 1.378 (3) |
N11—N12 | 1.3844 (18) | C22—H22 | 0.9300 |
N11—H11 | 0.859 (19) | C23—C24 | 1.353 (4) |
N12—C17 | 1.275 (2) | C23—H23 | 0.9300 |
C17—C11 | 1.455 (2) | C24—C25 | 1.378 (4) |
C17—H17 | 0.9300 | C24—H24 | 0.9300 |
C11—C16 | 1.388 (2) | C25—C26 | 1.394 (3) |
C11—C12 | 1.392 (2) | C25—H25 | 0.9300 |
C12—C13 | 1.378 (2) | C26—H26 | 0.9300 |
C12—H12 | 0.9300 | S31—C35 | 1.702 (2) |
C13—C14 | 1.391 (3) | S31—C32 | 1.7235 (18) |
C13—H13 | 0.9300 | C32—C33 | 1.376 (2) |
C14—O14 | 1.352 (2) | C33—C34 | 1.411 (3) |
C14—C15 | 1.381 (2) | C33—H33 | 0.9300 |
O14—H14 | 0.84 (3) | C34—C35 | 1.343 (3) |
C15—C16 | 1.379 (2) | C34—H34 | 0.9300 |
C15—H15 | 0.9300 | C35—H35 | 0.9300 |
C16—H16 | 0.9300 | ||
O1—C1—N11 | 123.27 (15) | C27—N21—H21 | 121.3 (14) |
O1—C1—C2 | 120.61 (15) | C2—N21—H21 | 116.8 (14) |
N11—C1—C2 | 116.11 (13) | O27—C27—N21 | 121.39 (15) |
C3—C2—N21 | 120.54 (14) | O27—C27—C21 | 121.18 (16) |
C3—C2—C1 | 124.32 (15) | N21—C27—C21 | 117.32 (14) |
N21—C2—C1 | 115.10 (13) | C26—C21—C22 | 118.82 (18) |
C2—C3—C32 | 129.69 (16) | C26—C21—C27 | 118.41 (17) |
C2—C3—H3 | 115.2 | C22—C21—C27 | 122.62 (17) |
C32—C3—H3 | 115.2 | C23—C22—C21 | 120.6 (2) |
C1—N11—N12 | 120.08 (13) | C23—C22—H22 | 119.7 |
C1—N11—H11 | 122.5 (13) | C21—C22—H22 | 119.7 |
N12—N11—H11 | 117.2 (13) | C24—C23—C22 | 120.5 (2) |
C17—N12—N11 | 113.83 (14) | C24—C23—H23 | 119.8 |
N12—C17—C11 | 123.09 (15) | C22—C23—H23 | 119.8 |
N12—C17—H17 | 118.5 | C23—C24—C25 | 120.1 (2) |
C11—C17—H17 | 118.5 | C23—C24—H24 | 119.9 |
C16—C11—C12 | 118.20 (15) | C25—C24—H24 | 119.9 |
C16—C11—C17 | 119.08 (15) | C24—C25—C26 | 119.9 (2) |
C12—C11—C17 | 122.71 (16) | C24—C25—H25 | 120.1 |
C13—C12—C11 | 120.66 (17) | C26—C25—H25 | 120.1 |
C13—C12—H12 | 119.7 | C21—C26—C25 | 120.2 (2) |
C11—C12—H12 | 119.7 | C21—C26—H26 | 119.9 |
C12—C13—C14 | 120.29 (16) | C25—C26—H26 | 119.9 |
C12—C13—H13 | 119.9 | C35—S31—C32 | 91.97 (10) |
C14—C13—H13 | 119.9 | C33—C32—C3 | 123.35 (17) |
O14—C14—C15 | 117.42 (17) | C33—C32—S31 | 110.17 (14) |
O14—C14—C13 | 123.00 (16) | C3—C32—S31 | 126.48 (13) |
C15—C14—C13 | 119.57 (15) | C32—C33—C34 | 112.82 (19) |
C14—O14—H14 | 110.1 (19) | C32—C33—H33 | 123.6 |
C16—C15—C14 | 119.75 (17) | C34—C33—H33 | 123.6 |
C16—C15—H15 | 120.1 | C35—C34—C33 | 112.70 (18) |
C14—C15—H15 | 120.1 | C35—C34—H34 | 123.7 |
C15—C16—C11 | 121.52 (16) | C33—C34—H34 | 123.7 |
C15—C16—H16 | 119.2 | C34—C35—S31 | 112.35 (15) |
C11—C16—H16 | 119.2 | C34—C35—H35 | 123.8 |
C27—N21—C2 | 121.16 (13) | S31—C35—H35 | 123.8 |
O1—C1—C2—C3 | −166.88 (16) | C2—N21—C27—O27 | −3.6 (2) |
N11—C1—C2—C3 | 11.8 (2) | C2—N21—C27—C21 | 172.62 (13) |
O1—C1—C2—N21 | 11.0 (2) | O27—C27—C21—C26 | −11.9 (2) |
N11—C1—C2—N21 | −170.33 (14) | N21—C27—C21—C26 | 171.89 (16) |
N21—C2—C3—C32 | 1.0 (3) | O27—C27—C21—C22 | 163.63 (16) |
C1—C2—C3—C32 | 178.77 (16) | N21—C27—C21—C22 | −12.6 (2) |
O1—C1—N11—N12 | 1.9 (3) | C26—C21—C22—C23 | 0.3 (3) |
C2—C1—N11—N12 | −176.74 (14) | C27—C21—C22—C23 | −175.14 (17) |
C1—N11—N12—C17 | 175.03 (16) | C21—C22—C23—C24 | 0.3 (3) |
N11—N12—C17—C11 | 179.60 (16) | C22—C23—C24—C25 | −0.6 (4) |
N12—C17—C11—C16 | 171.54 (17) | C23—C24—C25—C26 | 0.4 (4) |
N12—C17—C11—C12 | −7.3 (3) | C22—C21—C26—C25 | −0.5 (3) |
C16—C11—C12—C13 | −1.0 (3) | C27—C21—C26—C25 | 175.14 (18) |
C17—C11—C12—C13 | 177.86 (16) | C24—C25—C26—C21 | 0.1 (4) |
C11—C12—C13—C14 | 0.5 (3) | C2—C3—C32—C33 | 178.32 (19) |
C12—C13—C14—O14 | 178.76 (17) | C2—C3—C32—S31 | −1.3 (3) |
C12—C13—C14—C15 | 0.1 (3) | C35—S31—C32—C33 | 0.22 (16) |
O14—C14—C15—C16 | −178.83 (17) | C35—S31—C32—C3 | 179.89 (17) |
C13—C14—C15—C16 | −0.1 (3) | C3—C32—C33—C34 | 179.77 (18) |
C14—C15—C16—C11 | −0.5 (3) | S31—C32—C33—C34 | −0.6 (2) |
C12—C11—C16—C15 | 1.0 (3) | C32—C33—C34—C35 | 0.7 (3) |
C17—C11—C16—C15 | −177.89 (18) | C33—C34—C35—S31 | −0.5 (3) |
C3—C2—N21—C27 | −86.1 (2) | C32—S31—C35—C34 | 0.18 (18) |
C1—C2—N21—C27 | 95.92 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O27i | 0.86 (2) | 2.10 (2) | 2.9400 (18) | 168 (2) |
N21—H21···O1ii | 0.827 (19) | 2.238 (19) | 3.0002 (18) | 153.5 (18) |
O14—H14···O1iii | 0.84 (3) | 1.97 (3) | 2.7727 (19) | 162 (3) |
O14—H14···N12iii | 0.84 (3) | 2.59 (3) | 3.133 (2) | 124 (2) |
C3—H3···O27i | 0.93 | 2.52 | 3.333 (2) | 147 |
C17—H17···O27i | 0.93 | 2.57 | 3.350 (2) | 142 |
C24—H24···O14iv | 0.93 | 2.58 | 3.364 (3) | 142 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y, −z+3/2; (iii) −x+3/2, y−1/2, −z+3/2; (iv) x−1/2, y+3/2, z. |
Acknowledgements
KNS gratefully acknowledges the Department of Chemistry, Shri Madhwa Vadiraja Institute of Technology, Bantakal (VTU Belgam) for providing research facilities. JPJ acknowledges the NSF–MRI program (grant No. 1039027) for funds to purchase the X-ray diffractometer.
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