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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 7| July 2014| Pages o793-o794
https://doi.org/10.1107/S1600536814013798

(E)-N′-(3,4-Di­meth­­oxy­benzyl­­idene)nicotinohydrazide monohydrate

J. Josephine Novina,a G. Vasuki,b* M. Sureshc and M. Syed Ali Padushac

aDepartment of Physics, Idhaya College for Women, Kumbakonam-1, India, bDepartment of Physics, Kunthavai Naachiar Govt. Arts College (W) (Autonomous), Thanjavur-7, India, and cPG & Research Department of Chemistry, Jamal Mohamed College (Autonomous), Tiruchirappalli-20, India
*Correspondence e-mail: vasuki.arasi@yahoo.com

(Received 9 June 2014; accepted 12 June 2014; online 18 June 2014)

In the title hydrated compound, C15H15N3O3·H2O, the nicotinohydrazide mol­ecule adopts a trans conformation with respect to the C=N double bond. The dihedral angle between the benzene and pyridine rings is 5.10 (14)°. In the crystal, the solvent water mol­ecule acts as an acceptor, forming an N—H⋯O hydrogen bond supported by two C—H⋯O contacts. It also acts as a donor, forming bifurcated O—H⋯(O,O) and O—H⋯N hydrogen bonds that combine with the former contacts to form zigzag chains of mol­ecules along the c-axis direction. An additional O—H⋯O donor contact completes a set of six hydrogen bonds to and from the water mol­ecule and connects it to a third nicotinohydrazide mol­ecule. This latter contact combines with weaker C—H⋯O hydrogen bonds supported by a C—H⋯π contact to stack mol­ecules along b in a three-dimensional network.

CCDC reference: 1008073

Related literature

For the biological activity of hydrazone compounds, see: Singh & Raghav (2011[Singh, M. & Raghav, N. (2011). Int. J. Pharm. Pharm. Sci. 3, 26-32.]); Patil et al. (2011[Patil, B. R., Machakanur, S. S., Hunoor, R. S., Badiger, D. S., Gudasi, K. B. & Bligh, S. W. A. (2011). Pharma Chem. 3, 377-388.]). For background to the use of nicotinohydrazides as catalysts and of their transition metal complexes in the treatment of tuberculosis, see: Torje et al. (2012[Torje, I. A., Vălean, A.-M. & Cristea, C. (2012). Rev. Roum. Chim. 57, 337-344.]). For closely related structures, see: Novina et al. (2013[Novina, J. J., Vasuki, G., Suresh, M. & Padusha, M. S. A. (2013). Acta Cryst. E69, o1177-o1178.]); Wang et al. (2010[Wang, P., Li, C. & Su, Y.-Q. (2010). Acta Cryst. E66, o542.]).

[Scheme 1]

Experimental

Crystal data

  • C15H15N3O3·H2O

  • Mr = 303.32

  • Monoclinic, P 21 /n

  • a = 4.9128 (6) Å

  • b = 25.137 (4) Å

  • c = 12.2950 (16) Å

  • β = 96.513 (4)°

  • V = 1508.6 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 296 K

  • 0.50 × 0.35 × 0.30 mm
Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.952, Tmax = 0.971

  • 11633 measured reflections

  • 3704 independent reflections

  • 2250 reflections with I > 2σ(I)

  • Rint = 0.036
Refinement

  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.141

  • S = 1.02

  • 3704 reflections

  • 209 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2–C7 benzene ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2N2⋯O1Wi 0.86 2.06 2.8942 (19) 165
O1W—H2O1⋯O3 0.85 (2) 2.15 (2) 2.955 (2) 157 (3)
O1W—H2O1⋯N1 0.85 (2) 2.49 (2) 3.1087 (19) 130 (2)
C11—H11⋯O1Wi 0.93 2.30 3.199 (3) 162
C8—H8⋯O1Wi 0.93 2.67 3.425 (2) 139
O1W—H1O1⋯O3ii 0.86 (2) 2.09 (2) 2.901 (2) 159 (3)
C1—H1C⋯Cg2ii 0.96 2.88 3.729 (3) 148
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

CCDC reference: 1008073

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536814013798/sj5412sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814013798/sj5412Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536814013798/sj5412Isup3.cml

checkCIF report


Comment top

Hydrazones constitute an important class of biologically active drug molecules that have attracted the attention of medicinal chemists due to their wide range of pharmacological properties (Singh & Raghav, 2011). Hydrazone derivatives containing an azomethine (–CONHN═CH–) group have been shown to exhibit antiproliferative activities and act as cytotoxic agents with the ability to prevent cell progression in cancerous cells through different mechanisms (Patil et al., 2011). Moreover, hydrazone derivatives may act as multidentate ligands and their transition metal complexes have been used in the treatment of tuberculosis, in colorimetric or fluorimetric analytic determinations, as well as in applications involving catalytic processes (Torje et al., 2012). As part of our studies of substituent effects on the structure and other aspects of hydrazone derivatives, such as (E)—N'-(4-Methoxybenzylidene)pyridine-3-carbohydrazide dihydrate (Novina et al., 2013), in the present work we report the synthesis and crystal structure of the title compound.

The molecule of the title hydrazide derivative (Fig. 1), C15H15N3O3·H2O, exists in a trans conformation with respect to the C8═N1 double bond [1.277 (2) Å] with the torsion angle N2—N1—-C8—C5 = -177.58 (14)°. It also adopts the amido form with the C9═O3 bond length of 1.2322 (19) Å which is very close to the reported C═O bond length of a similar structure (Wang et al., 2010). The benzene and pyridine rings (C2—C7 and N3/C10—C14, respectively) are each planar with a dihedral angle of 5.10 (14)° between their mean-planes. This is comparable to the corresponding angle found in a related structure (Novina et al., 2013). One of the methoxy group is almost coplanar with the C2—C7 benzene ring whereas the other one deviates somewhat from the benzene ring plane [torsion angles: C1—O1—C2—C7 = -3.9 (3), C15—O2—C3—C4 = 16.5 (3)°].

The water molecule forms six H–bonds with three different nicotinohydrazone molecules. N—H···O, O—H···O, O—H···N and C—H···O hydrogen bonds are present in the crystal system (Table 1). One of the H atoms of the water molecule forms bifurcated hydrogen bonds to the azomethine nitrogen and the carbonyl oxygen atoms of one neighboring molecule (Fig. 2). The water molecule acts as a hydrogen bond acceptor towards another nicotinohydrazone molecule through N–H···O and C—H···O hydrogen bonds. Through these interactions the molecules are interconnected through the water molecule to form infinite chains parallel to the b axis of the unit cell (Fig. 2). Furthermore, a C1—H1C···π interaction involving the phenyl (C2—C7) ring together with O–H···O and C–H···O contacts to generate a three dimensional network of molecules stacked along the a axis direction (Fig. 3).

Related literature top

For the biological activity of hydrazone compounds, see: Singh & Raghav (2011); Patil et al. (2011). For background to the use of nicotinohydrazides as catalysts and of their transition metal complexes in the treatment of tuberculosis, see: Torje et al. (2012). For closely related structures, see: Novina et al. (2013); Wang et al. (2010).

Experimental top

3,4-dimethoxybenzaldehyde (4.1 ml, 0.025 mol) was added to an ethanolic solution of nicotinicacid hydrazide (3.4 g, 0.025 mol). After the addition was complete the reaction mixture was stirred well in an ice cold condition for 3 hrs. The colourless solid that formed was filtered and washed several times with petroleum ether (40–60%). The crude solid obtained was dried and recrystallized from absolute alcohol. The recrystallized product was dried over vacuum.

Refinement top

The H atoms of the solvent water were located in a difference map and refined freely with isotropic displacement parameters with their bond distances restrained to 0.86 (2) Å. Other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H = 0.93 Å, CH3 = 0.96 Å, N—H = 0.86 Å and with Uiso(H) = 1.5Ueq(CH3) and 1.2Ueq(CH, NH).

Structure description top

Hydrazones constitute an important class of biologically active drug molecules that have attracted the attention of medicinal chemists due to their wide range of pharmacological properties (Singh & Raghav, 2011). Hydrazone derivatives containing an azomethine (–CONHN═CH–) group have been shown to exhibit antiproliferative activities and act as cytotoxic agents with the ability to prevent cell progression in cancerous cells through different mechanisms (Patil et al., 2011). Moreover, hydrazone derivatives may act as multidentate ligands and their transition metal complexes have been used in the treatment of tuberculosis, in colorimetric or fluorimetric analytic determinations, as well as in applications involving catalytic processes (Torje et al., 2012). As part of our studies of substituent effects on the structure and other aspects of hydrazone derivatives, such as (E)—N'-(4-Methoxybenzylidene)pyridine-3-carbohydrazide dihydrate (Novina et al., 2013), in the present work we report the synthesis and crystal structure of the title compound.

The molecule of the title hydrazide derivative (Fig. 1), C15H15N3O3·H2O, exists in a trans conformation with respect to the C8═N1 double bond [1.277 (2) Å] with the torsion angle N2—N1—-C8—C5 = -177.58 (14)°. It also adopts the amido form with the C9═O3 bond length of 1.2322 (19) Å which is very close to the reported C═O bond length of a similar structure (Wang et al., 2010). The benzene and pyridine rings (C2—C7 and N3/C10—C14, respectively) are each planar with a dihedral angle of 5.10 (14)° between their mean-planes. This is comparable to the corresponding angle found in a related structure (Novina et al., 2013). One of the methoxy group is almost coplanar with the C2—C7 benzene ring whereas the other one deviates somewhat from the benzene ring plane [torsion angles: C1—O1—C2—C7 = -3.9 (3), C15—O2—C3—C4 = 16.5 (3)°].

The water molecule forms six H–bonds with three different nicotinohydrazone molecules. N—H···O, O—H···O, O—H···N and C—H···O hydrogen bonds are present in the crystal system (Table 1). One of the H atoms of the water molecule forms bifurcated hydrogen bonds to the azomethine nitrogen and the carbonyl oxygen atoms of one neighboring molecule (Fig. 2). The water molecule acts as a hydrogen bond acceptor towards another nicotinohydrazone molecule through N–H···O and C—H···O hydrogen bonds. Through these interactions the molecules are interconnected through the water molecule to form infinite chains parallel to the b axis of the unit cell (Fig. 2). Furthermore, a C1—H1C···π interaction involving the phenyl (C2—C7) ring together with O–H···O and C–H···O contacts to generate a three dimensional network of molecules stacked along the a axis direction (Fig. 3).

For the biological activity of hydrazone compounds, see: Singh & Raghav (2011); Patil et al. (2011). For background to the use of nicotinohydrazides as catalysts and of their transition metal complexes in the treatment of tuberculosis, see: Torje et al. (2012). For closely related structures, see: Novina et al. (2013); Wang et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Crystal packing of the title compound viewed along the b axis. Hydrogen bonds are shown as dashed lines.
[Figure 3] Fig. 3. The crystal packing of the title compound viewed along the a axis. Hydrogen bonds are drawn as dashed lines and a representative C–H···π contact is shown as a dotted line.
(E)-N'-(3,4-Dimethoxybenzylidene)nicotinohydrazide monohydrate top
Crystal data top
C15H15N3O3·H2OF(000) = 640
Mr = 303.32Dx = 1.335 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2357 reflections
a = 4.9128 (6) Åθ = 4.7–51.8°
b = 25.137 (4) ŵ = 0.10 mm−1
c = 12.2950 (16) ÅT = 296 K
β = 96.513 (4)°Block, colorless
V = 1508.6 (4) Å30.50 × 0.35 × 0.30 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer		3704 independent reflections
Radiation source: fine-focus sealed tube2250 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ω and φ scanθmax = 28.3°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		h = −6→6
Tmin = 0.952, Tmax = 0.971k = −33→33
11633 measured reflectionsl = −16→16
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0655P)2 + 0.1374P]
where P = (Fo2 + 2Fc2)/3
3704 reflections(Δ/σ)max < 0.001
209 parametersΔρmax = 0.21 e Å−3
3 restraintsΔρmin = −0.23 e Å−3
Crystal data top
C15H15N3O3·H2OV = 1508.6 (4) Å3
Mr = 303.32Z = 4
Monoclinic, P21/nMo Kα radiation
a = 4.9128 (6) ŵ = 0.10 mm−1
b = 25.137 (4) ÅT = 296 K
c = 12.2950 (16) Å0.50 × 0.35 × 0.30 mm
β = 96.513 (4)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer		3704 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		2250 reflections with I > 2σ(I)
Tmin = 0.952, Tmax = 0.971Rint = 0.036
11633 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0483 restraints
wR(F2) = 0.141H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.21 e Å−3
3704 reflectionsΔρmin = −0.23 e Å−3
209 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C11.8728 (4)0.00081 (9)0.12935 (17)0.0591 (6)
H1A1.7449−0.00750.06670.089*
H1B1.9736−0.03060.15310.089*
H1C1.99750.02770.11010.089*
C21.5690 (3)0.06393 (7)0.19504 (13)0.0345 (4)
C31.4107 (3)0.07841 (7)0.27937 (13)0.0349 (4)
C41.2439 (3)0.12194 (7)0.26645 (13)0.0360 (4)
H41.14020.13150.32210.043*
C51.2269 (3)0.15227 (7)0.17060 (13)0.0343 (4)
C81.0486 (3)0.19839 (7)0.15615 (13)0.0376 (4)
H81.02670.21580.08890.045*
C90.6145 (3)0.27874 (7)0.28846 (13)0.0356 (4)
C100.4296 (3)0.32458 (7)0.25774 (13)0.0358 (4)
C140.2785 (4)0.34525 (9)0.33488 (15)0.0512 (5)
H140.29560.32930.40350.061*
C130.0882 (4)0.40894 (9)0.22029 (18)0.0574 (6)
H13−0.03060.43760.20650.069*
C120.2313 (5)0.39213 (11)0.13952 (19)0.0764 (8)
H120.21320.40930.07210.092*
C110.4038 (5)0.34939 (10)0.15793 (17)0.0704 (7)
H110.50300.33730.10280.084*
C61.3787 (3)0.13702 (7)0.08749 (13)0.0396 (4)
H61.36580.15640.02270.047*
C71.5492 (3)0.09318 (7)0.10011 (13)0.0388 (4)
H71.65110.08340.04400.047*
C151.2265 (4)0.05011 (9)0.43970 (15)0.0578 (6)
H15A1.23280.08470.47300.087*
H15C1.25450.02340.49560.087*
H15B1.05100.04490.39820.087*
N10.9212 (3)0.21555 (6)0.23409 (11)0.0364 (3)
N20.7497 (3)0.25839 (6)0.20898 (10)0.0370 (3)
H2N20.73000.27170.14410.044*
N30.1091 (4)0.38654 (8)0.31852 (15)0.0637 (5)
O11.7281 (2)0.01981 (5)0.21562 (10)0.0467 (3)
O1W1.1763 (3)0.21759 (7)0.47728 (11)0.0606 (4)
O21.4351 (3)0.04615 (5)0.36928 (10)0.0496 (4)
O30.6430 (3)0.26124 (6)0.38267 (9)0.0505 (4)
H1O11.310 (4)0.2231 (12)0.440 (2)0.101 (10)*
H2O11.028 (4)0.2235 (11)0.4360 (19)0.102 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0537 (11)0.0579 (14)0.0675 (14)0.0190 (10)0.0148 (10)−0.0139 (11)
C20.0304 (8)0.0321 (9)0.0414 (9)−0.0008 (7)0.0062 (6)−0.0027 (7)
C30.0366 (8)0.0365 (10)0.0318 (8)−0.0006 (7)0.0052 (6)0.0023 (7)
C40.0401 (9)0.0401 (10)0.0291 (8)0.0058 (8)0.0094 (6)−0.0026 (7)
C50.0368 (8)0.0356 (10)0.0307 (8)0.0022 (7)0.0038 (6)−0.0009 (7)
C80.0437 (9)0.0406 (10)0.0287 (8)0.0060 (8)0.0049 (7)0.0027 (7)
C90.0381 (9)0.0392 (10)0.0297 (8)0.0015 (7)0.0052 (6)0.0002 (7)
C100.0360 (8)0.0383 (10)0.0335 (8)0.0035 (7)0.0060 (6)−0.0004 (7)
C140.0625 (12)0.0551 (13)0.0375 (10)0.0177 (10)0.0117 (8)0.0020 (9)
C130.0603 (12)0.0493 (13)0.0627 (13)0.0206 (10)0.0075 (10)0.0025 (10)
C120.0972 (17)0.0813 (18)0.0549 (13)0.0482 (15)0.0267 (12)0.0252 (12)
C110.0879 (16)0.0809 (18)0.0476 (12)0.0467 (14)0.0305 (11)0.0188 (11)
C60.0448 (9)0.0441 (11)0.0310 (8)0.0003 (8)0.0094 (7)0.0046 (8)
C70.0391 (9)0.0432 (11)0.0368 (9)0.0017 (8)0.0152 (7)−0.0038 (8)
C150.0555 (12)0.0773 (16)0.0427 (10)0.0078 (11)0.0142 (9)0.0198 (10)
N10.0409 (8)0.0367 (9)0.0313 (7)0.0080 (6)0.0023 (6)0.0011 (6)
N20.0447 (8)0.0388 (9)0.0274 (7)0.0107 (7)0.0038 (6)0.0049 (6)
N30.0736 (12)0.0635 (13)0.0565 (11)0.0278 (10)0.0180 (9)−0.0034 (9)
O10.0467 (7)0.0415 (8)0.0543 (8)0.0114 (6)0.0159 (6)0.0009 (6)
O1W0.0661 (10)0.0840 (12)0.0303 (7)−0.0146 (9)−0.0007 (7)0.0055 (7)
O20.0559 (8)0.0533 (9)0.0418 (7)0.0151 (7)0.0153 (6)0.0152 (6)
O30.0611 (8)0.0611 (9)0.0305 (6)0.0175 (7)0.0106 (5)0.0088 (6)
Geometric parameters (Å, º) top
C1—O11.424 (2)C14—N31.331 (2)
C1—H1A0.9600C14—H140.9300
C1—H1B0.9600C13—N31.326 (3)
C1—H1C0.9600C13—C121.348 (3)
C2—O11.364 (2)C13—H130.9300
C2—C71.373 (2)C12—C111.371 (3)
C2—C31.412 (2)C12—H120.9300
C3—O21.3652 (19)C11—H110.9300
C3—C41.366 (2)C6—C71.382 (2)
C4—C51.398 (2)C6—H60.9300
C4—H40.9300C7—H70.9300
C5—C61.386 (2)C15—O21.418 (2)
C5—C81.452 (2)C15—H15A0.9600
C8—N11.277 (2)C15—H15C0.9600
C8—H80.9300C15—H15B0.9600
C9—O31.2322 (19)N1—N21.3806 (19)
C9—N21.344 (2)N2—H2N20.8600
C9—C101.489 (2)O1W—H1O10.856 (17)
C10—C111.370 (3)O1W—H2O10.854 (17)
C10—C141.371 (2)
O1—C1—H1A109.5N3—C13—C12123.02 (19)
O1—C1—H1B109.5N3—C13—H13118.5
H1A—C1—H1B109.5C12—C13—H13118.5
O1—C1—H1C109.5C13—C12—C11119.2 (2)
H1A—C1—H1C109.5C13—C12—H12120.4
H1B—C1—H1C109.5C11—C12—H12120.4
O1—C2—C7125.21 (15)C10—C11—C12119.83 (18)
O1—C2—C3115.16 (15)C10—C11—H11120.1
C7—C2—C3119.62 (15)C12—C11—H11120.1
O2—C3—C4124.52 (14)C7—C6—C5120.51 (16)
O2—C3—C2115.86 (15)C7—C6—H6119.7
C4—C3—C2119.61 (15)C5—C6—H6119.7
C3—C4—C5120.85 (15)C2—C7—C6120.38 (15)
C3—C4—H4119.6C2—C7—H7119.8
C5—C4—H4119.6C6—C7—H7119.8
C6—C5—C4119.01 (16)O2—C15—H15A109.5
C6—C5—C8119.90 (15)O2—C15—H15C109.5
C4—C5—C8121.07 (14)H15A—C15—H15C109.5
N1—C8—C5121.19 (15)O2—C15—H15B109.5
N1—C8—H8119.4H15A—C15—H15B109.5
C5—C8—H8119.4H15C—C15—H15B109.5
O3—C9—N2122.34 (16)C8—N1—N2115.72 (14)
O3—C9—C10121.05 (15)C9—N2—N1118.29 (13)
N2—C9—C10116.61 (14)C9—N2—H2N2120.9
C11—C10—C14116.41 (17)N1—N2—H2N2120.9
C11—C10—C9124.86 (16)C13—N3—C14116.83 (17)
C14—C10—C9118.70 (15)C2—O1—C1117.29 (15)
N3—C14—C10124.68 (18)H1O1—O1W—H2O1108 (2)
N3—C14—H14117.7C3—O2—C15116.70 (13)
C10—C14—H14117.7
O1—C2—C3—O2−0.8 (2)C9—C10—C11—C12−178.5 (2)
C7—C2—C3—O2177.74 (15)C13—C12—C11—C10−0.3 (4)
O1—C2—C3—C4−179.80 (15)C4—C5—C6—C7−1.4 (3)
C7—C2—C3—C4−1.3 (2)C8—C5—C6—C7−179.96 (16)
O2—C3—C4—C5−178.69 (15)O1—C2—C7—C6179.32 (15)
C2—C3—C4—C50.2 (3)C3—C2—C7—C61.0 (3)
C3—C4—C5—C61.1 (3)C5—C6—C7—C20.4 (3)
C3—C4—C5—C8179.61 (15)C5—C8—N1—N2−177.58 (14)
C6—C5—C8—N1−175.03 (16)O3—C9—N2—N11.6 (3)
C4—C5—C8—N16.5 (3)C10—C9—N2—N1−179.42 (14)
O3—C9—C10—C11174.1 (2)C8—N1—N2—C9−178.76 (15)
N2—C9—C10—C11−4.9 (3)C12—C13—N3—C14−0.8 (4)
O3—C9—C10—C14−3.7 (3)C10—C14—N3—C13−0.3 (3)
N2—C9—C10—C14177.30 (17)C7—C2—O1—C1−3.9 (3)
C11—C10—C14—N31.0 (3)C3—C2—O1—C1174.54 (15)
C9—C10—C14—N3178.98 (18)C4—C3—O2—C1516.5 (3)
N3—C13—C12—C111.1 (4)C2—C3—O2—C15−162.44 (16)
C14—C10—C11—C12−0.7 (4)
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
N2—H2N2···O1Wi0.862.062.8942 (19)165
O1W—H2O1···O30.85 (2)2.15 (2)2.955 (2)157 (3)
O1W—H2O1···N10.85 (2)2.49 (2)3.1087 (19)130 (2)
C11—H11···O1Wi0.932.303.199 (3)162
C8—H8···O1Wi0.932.673.425 (2)139
O1W—H1O1···O3ii0.86 (2)2.09 (2)2.901 (2)159 (3)
C1—H1C···Cg2ii0.962.883.729 (3)148
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
N2—H2N2···O1Wi0.862.062.8942 (19)164.6
O1W—H2O1···O30.854 (17)2.149 (19)2.955 (2)157 (3)
O1W—H2O1···N10.854 (17)2.49 (2)3.1087 (19)130 (2)
C11—H11···O1Wi0.932.303.199 (3)161.5
C8—H8···O1Wi0.932.673.425 (2)139.0
O1W—H1O1···O3ii0.856 (17)2.085 (19)2.901 (2)159 (3)
C1—H1C···Cg2ii0.962.883.729 (3)148
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x+1, y, z.
 

Acknowledgements

The authors thank the Sophisticated Analytical Instrument Facility, STIC, Cochin University of Science & Technology, Cochin, for the data collection.

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ISSN: 2056-9890
Volume 70| Part 7| July 2014| Pages o793-o794
https://doi.org/10.1107/S1600536814013798
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