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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 67| Part 10| October 2011| Page o2713
https://doi.org/10.1107/S1600536811038153

N′-[(1E)-(2-Hy­dr­oxy­naphthalen-1-yl)methyl­­idene]-2-meth­­oxy­benzohydrazide

Xiao-Yan Lia*

aZibo Vocational Institute, Zibo 255314, People's Republic of China
*Correspondence e-mail: lixiaoyan_zb@126.com

(Received 16 September 2011; accepted 19 September 2011; online 30 September 2011)

There are three independent mol­ecules in the asymmetric unit of the title compound, C19H16N2O3, in which the dihedral angles between the naphthalene ring system and the benzene ring are 7.52 (16), 18.15 (18), and 13.9 (2)°. All the mol­ecules exist in the trans configuration with respect to the methyl­idene units. In each mol­ecule there is one O—H⋯N and one N—H⋯O intra­molecular hydrogen bond. In the crystal, two of the mol­ecules are linked via a bifurcated N—H⋯(O,O) hydrogen bond. All three mol­ecules are further linked via C—H⋯O inter­actions.

Related literature

For the syntheses and crystal structures of hydrazone compounds, see: Hashemian et al. (2011[Hashemian, S., Ghaeinee, V. & Notash, B. (2011). Acta Cryst. E67, o171.]); Lei (2011[Lei, Y. (2011). Acta Cryst. E67, o162.]); Shalash et al. (2010[Shalash, M., Salhin, A., Adnan, R., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o3126-o3127.]); Li (2011a[Li, H.-B. (2011a). Acta Cryst. E67, o1532.]). For the crystal structures of similar compounds reported recently by the author, see: Li (2011b[Li, X.-Y. (2011b). Acta Cryst. E67, o1798.],c[Li, X.-Y. (2011c). Acta Cryst. E67, o2511.]).

[Scheme 1]

Experimental

Crystal data

  • C19H16N2O3

  • Mr = 320.34

  • Triclinic, [P \overline 1]

  • a = 12.2266 (19) Å

  • b = 14.212 (3) Å

  • c = 15.805 (2) Å

  • α = 107.507 (3)°

  • β = 108.475 (3)°

  • γ = 95.885 (3)°

  • V = 2423.9 (7) Å3

  • Z = 6

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 298 K

  • 0.23 × 0.23 × 0.21 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.980, Tmax = 0.981

  • 20059 measured reflections

  • 10353 independent reflections

  • 3438 reflections with I > 2σ(I)

  • Rint = 0.054
Refinement

  • R[F2 > 2σ(F2)] = 0.061

  • wR(F2) = 0.184

  • S = 0.94

  • 10353 reflections

  • 666 parameters

  • 4 restraints

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

  • Δρmax = 0.13 e Å−3

  • Δρmin = −0.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯N1 0.82 1.84 2.556 (3) 145
N2—H2⋯O3 0.91 (1) 1.94 (2) 2.622 (3) 131 (3)
N2—H2⋯O8i 0.91 (1) 2.41 (2) 3.094 (4) 132 (2)
O4—H4⋯N3 0.86 (1) 1.82 (2) 2.538 (4) 141 (3)
N4—H4B⋯O6 0.91 (1) 1.95 (2) 2.647 (4) 132 (3)
O7—H7⋯N5 0.82 1.80 2.517 (4) 146
N6—H6A⋯O9 0.89 (1) 1.89 (2) 2.621 (4) 138 (3)
C11—H11⋯O8i 0.93 2.46 3.122 (4) 129
C38—H38B⋯O2ii 0.96 2.35 3.090 (5) 133
C57—H57B⋯O4iii 0.96 2.56 3.435 (5) 151
Symmetry codes: (i) x, y, z-1; (ii) -x+2, -y+1, -z+1; (iii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811038153/su2316sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811038153/su2316Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811038153/su2316Isup3.cml

checkCIF report


Comment top

In the last few years, hydrazones have attracted much attention for their syntheses and crystal structures (Hashemian et al., 2011; Lei, 2011; Shalash et al., 2010). As a continuation of our work on such compounds (Li, 2011a,b), the author reports herein on the crystal structure of the new title hydrazone compound.

In the asymmetric unit of the title compound there are three (A, B and C) independent molecules (Fig. 1). The bond distances and angles are comparable to those observed in similar compounds (Li, 2011b,c). The dihedral angles between the naphthalene and the benzene rings in the three molecules are 7.52 (16), 18.15 (18), and 13.9 (2)°, for molecules A, B and C, respectively. All the molecules exist in the trans configuration with respect to the methylidene units. In each molecule there is an O-H···N and a N-H···O intramolecular hydrogen bond (Table 1).

In the crystal the A and C molecules are linked by a bifurcated hydrogen bond involving the NH group of molecule A [N2-H2···O8] (Table 1). All three molecules are further linked to one another via C-H···O interactions (Table 1).

Related literature top

For the syntheses and crystal structures of hydrazone compounds, see: Hashemian et al. (2011); Lei (2011); Shalash et al. (2010); Li (2011a). For the crystal structures of similar compounds reported recently by the author, see: Li (2011b,c).

Experimental top

A mixture of 2-methoxybenzhydrazide (0.166 g, 1 mmol) and 2-hydroxy-1-naphthaldehyde (0.172 g, 1 mmol) in 30 ml of ethanol containing few drops of acetic acid was refluxed for about 1 h. On cooling to room temperature, a solid precipitate was formed. The solid was filtered and then recrystallized from methanol. Colourless crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of a solution of the title compound in methanol.

Refinement top

The NH H-atoms were located from a difference Fourier map and were freely refined. The OH and C-bound H-atoms were positioned geometrically and refined using a riding model: O—H = 0.82 Å, C—H = 0.93 and 0.96 Å, for CH and CH3 H-atoms, respectively, with Uiso(H) = k × Ueq(O,C), where k = 1.5 for OH and CH3 H-atoms, and k = 1.2 for all other H-atoms.

Structure description top

In the last few years, hydrazones have attracted much attention for their syntheses and crystal structures (Hashemian et al., 2011; Lei, 2011; Shalash et al., 2010). As a continuation of our work on such compounds (Li, 2011a,b), the author reports herein on the crystal structure of the new title hydrazone compound.

In the asymmetric unit of the title compound there are three (A, B and C) independent molecules (Fig. 1). The bond distances and angles are comparable to those observed in similar compounds (Li, 2011b,c). The dihedral angles between the naphthalene and the benzene rings in the three molecules are 7.52 (16), 18.15 (18), and 13.9 (2)°, for molecules A, B and C, respectively. All the molecules exist in the trans configuration with respect to the methylidene units. In each molecule there is an O-H···N and a N-H···O intramolecular hydrogen bond (Table 1).

In the crystal the A and C molecules are linked by a bifurcated hydrogen bond involving the NH group of molecule A [N2-H2···O8] (Table 1). All three molecules are further linked to one another via C-H···O interactions (Table 1).

For the syntheses and crystal structures of hydrazone compounds, see: Hashemian et al. (2011); Lei (2011); Shalash et al. (2010); Li (2011a). For the crystal structures of similar compounds reported recently by the author, see: Li (2011b,c).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the three independent molecules (A, B and C) of the title compound, showing the atom labelling. The displacement ellipsoids are drawn at the 30% probability level. Intramolecular O-H···N and N-H···O hydrogen bonds are indicated by dashed lines. The C-bound H-atoms have been omitted for clarity.
N'-[(1E)-(2-hydroxynaphthalen-1-yl)methylidene]-2-methoxybenzohydrazide top
Crystal data top
C19H16N2O3Z = 6
Mr = 320.34F(000) = 1008
Triclinic, P1Dx = 1.317 Mg m−3
a = 12.2266 (19) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.212 (3) ÅCell parameters from 1972 reflections
c = 15.805 (2) Åθ = 2.7–25.0°
α = 107.507 (3)°µ = 0.09 mm−1
β = 108.475 (3)°T = 298 K
γ = 95.885 (3)°Block, colourless
V = 2423.9 (7) Å30.23 × 0.23 × 0.21 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		10353 independent reflections
Radiation source: fine-focus sealed tube3438 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
ω scansθmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −15→15
Tmin = 0.980, Tmax = 0.981k = −18→17
20059 measured reflectionsl = −20→20
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184H atoms treated by a mixture of independent and constrained refinement
S = 0.94 w = 1/[σ2(Fo2) + (0.0526P)2]
where P = (Fo2 + 2Fc2)/3
10353 reflections(Δ/σ)max < 0.001
666 parametersΔρmax = 0.13 e Å−3
4 restraintsΔρmin = −0.15 e Å−3
Crystal data top
C19H16N2O3γ = 95.885 (3)°
Mr = 320.34V = 2423.9 (7) Å3
Triclinic, P1Z = 6
a = 12.2266 (19) ÅMo Kα radiation
b = 14.212 (3) ŵ = 0.09 mm−1
c = 15.805 (2) ÅT = 298 K
α = 107.507 (3)°0.23 × 0.23 × 0.21 mm
β = 108.475 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		10353 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3438 reflections with I > 2σ(I)
Tmin = 0.980, Tmax = 0.981Rint = 0.054
20059 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0614 restraints
wR(F2) = 0.184H atoms treated by a mixture of independent and constrained refinement
S = 0.94Δρmax = 0.13 e Å−3
10353 reflectionsΔρmin = −0.15 e Å−3
666 parameters
Special details top

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.

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 > 2sigma(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
N10.7028 (2)0.66822 (19)0.12093 (18)0.0611 (7)
N20.5820 (2)0.6409 (2)0.09232 (18)0.0600 (7)
N30.9007 (2)0.1667 (2)0.4186 (2)0.0708 (8)
N40.9645 (3)0.2611 (2)0.43764 (19)0.0687 (8)
N50.4514 (2)0.7856 (2)0.8040 (2)0.0738 (8)
N60.4112 (3)0.8381 (2)0.8720 (2)0.0740 (8)
O10.9121 (2)0.6929 (2)0.23860 (18)0.0873 (8)
H10.83990.68370.22090.131*
O20.6032 (2)0.60244 (19)0.22336 (17)0.0933 (8)
O30.36430 (18)0.60654 (17)−0.02694 (15)0.0761 (7)
O40.7731 (2)−0.0019 (2)0.2966 (2)0.1034 (9)
O50.8678 (2)0.2523 (2)0.28836 (18)0.0987 (9)
O61.1456 (2)0.41689 (17)0.54154 (16)0.0831 (7)
O70.5615 (3)0.6551 (2)0.7471 (3)0.1237 (11)
H70.53340.68860.78370.186*
O80.5332 (2)0.78589 (19)0.97944 (17)0.0900 (8)
O90.2894 (2)0.96365 (18)0.93681 (17)0.0842 (7)
C10.8710 (3)0.7184 (2)0.0879 (3)0.0618 (9)
C20.9480 (3)0.7153 (2)0.1729 (3)0.0691 (10)
C31.0712 (3)0.7350 (3)0.1956 (3)0.0917 (13)
H31.12150.73280.25280.110*
C41.1155 (4)0.7569 (3)0.1350 (4)0.1004 (15)
H4A1.19700.76970.15120.120*
C51.0438 (4)0.7614 (3)0.0477 (4)0.0866 (12)
C61.0888 (5)0.7824 (3)−0.0165 (5)0.124 (2)
H61.17040.79670.00040.149*
C71.0206 (6)0.7832 (4)−0.1024 (5)0.133 (2)
H7A1.05420.7956−0.14430.160*
C80.8966 (5)0.7646 (3)−0.1265 (3)0.1155 (16)
H80.84780.7661−0.18450.139*
C90.8477 (4)0.7444 (3)−0.0652 (3)0.0891 (12)
H90.76600.7319−0.08260.107*
C100.9190 (4)0.7421 (2)0.0238 (3)0.0732 (10)
C110.7438 (3)0.6925 (2)0.0634 (2)0.0609 (9)
H110.69250.69350.00610.073*
C120.5386 (3)0.6067 (2)0.1492 (2)0.0607 (9)
C130.4076 (3)0.5741 (2)0.1165 (2)0.0538 (8)
C140.3236 (3)0.5751 (2)0.0337 (2)0.0594 (9)
C150.2043 (3)0.5470 (3)0.0149 (3)0.0763 (10)
H150.14870.5505−0.03940.092*
C160.1684 (3)0.5137 (3)0.0771 (4)0.0897 (12)
H160.08820.49380.06420.108*
C170.2497 (4)0.5097 (3)0.1577 (3)0.0898 (12)
H170.22490.48690.19930.108*
C180.3668 (3)0.5392 (2)0.1769 (2)0.0703 (10)
H180.42130.53600.23180.084*
C190.2841 (3)0.5996 (3)−0.1172 (2)0.0881 (12)
H19A0.23580.5324−0.14980.132*
H19B0.32750.6145−0.15440.132*
H19C0.23470.6472−0.10840.132*
C200.8568 (3)0.0289 (3)0.4651 (3)0.0623 (9)
C210.7909 (3)−0.0327 (4)0.3714 (3)0.0811 (11)
C220.7382 (4)−0.1347 (4)0.3495 (3)0.1021 (14)
H220.6970−0.17630.28630.123*
C230.7474 (4)−0.1719 (3)0.4197 (4)0.1044 (15)
H230.7119−0.23910.40400.125*
C240.8093 (3)−0.1120 (3)0.5166 (4)0.0821 (11)
C250.8153 (4)−0.1510 (4)0.5892 (5)0.1082 (16)
H250.7780−0.21770.57350.130*
C260.8746 (5)−0.0932 (4)0.6814 (5)0.1133 (16)
H260.8771−0.11950.72910.136*
C270.9322 (4)0.0064 (4)0.7052 (3)0.0955 (13)
H270.97440.04610.76880.115*
C280.9269 (3)0.0457 (3)0.6359 (3)0.0769 (10)
H280.96520.11240.65330.092*
C290.8659 (3)−0.0110 (3)0.5396 (3)0.0660 (9)
C300.9174 (3)0.1300 (3)0.4855 (3)0.0672 (10)
H300.96860.16880.54710.081*
C310.9472 (3)0.2980 (3)0.3656 (3)0.0710 (10)
C321.0257 (3)0.3946 (3)0.3839 (2)0.0610 (9)
C331.1207 (3)0.4525 (3)0.4678 (2)0.0647 (9)
C341.1860 (3)0.5412 (3)0.4743 (3)0.0800 (11)
H341.24930.57870.53030.096*
C351.1584 (4)0.5745 (3)0.3986 (3)0.0912 (12)
H351.20220.63470.40360.109*
C361.0657 (4)0.5184 (3)0.3157 (3)0.0909 (12)
H361.04670.54060.26420.109*
C371.0008 (3)0.4294 (3)0.3083 (2)0.0777 (11)
H370.93880.39180.25140.093*
C381.2370 (3)0.4773 (3)0.6314 (2)0.0971 (13)
H38A1.31150.48550.62320.146*
H38B1.24120.44420.67680.146*
H38C1.21940.54240.65430.146*
C390.4664 (3)0.7488 (3)0.6523 (3)0.0709 (10)
C400.5324 (4)0.6785 (3)0.6673 (4)0.0955 (13)
C410.5746 (5)0.6247 (4)0.5978 (5)0.128 (2)
H410.61860.57700.60890.154*
C420.5511 (5)0.6422 (4)0.5161 (5)0.131 (2)
H420.57850.60560.47050.157*
C430.4857 (4)0.7148 (4)0.4970 (4)0.0979 (14)
C440.4633 (5)0.7349 (5)0.4128 (4)0.134 (2)
H440.48980.69780.36680.161*
C450.4043 (5)0.8068 (6)0.3963 (4)0.144 (2)
H450.38920.81840.33920.173*
C460.3663 (4)0.8635 (4)0.4661 (4)0.1291 (19)
H460.32800.91470.45630.155*
C470.3847 (3)0.8446 (4)0.5489 (3)0.0974 (13)
H470.35700.88200.59380.117*
C480.4444 (3)0.7701 (3)0.5669 (3)0.0792 (11)
C490.4215 (3)0.8000 (3)0.7241 (3)0.0731 (10)
H490.37100.84310.71230.088*
C500.4587 (3)0.8365 (3)0.9618 (3)0.0715 (10)
C510.4183 (3)0.8957 (3)1.0363 (3)0.0700 (10)
C520.3376 (3)0.9574 (3)1.0247 (3)0.0717 (10)
C530.3071 (3)1.0091 (3)1.1009 (3)0.0893 (12)
H530.25341.05051.09310.107*
C540.3569 (4)0.9986 (3)1.1876 (3)0.1009 (14)
H540.33541.03221.23820.121*
C550.4380 (4)0.9392 (4)1.2006 (3)0.1055 (15)
H550.47200.93301.25980.127*
C560.4681 (3)0.8889 (3)1.1252 (3)0.0915 (12)
H560.52360.84921.13430.110*
C570.2108 (4)1.0304 (3)0.9225 (3)0.1040 (14)
H57A0.14201.00960.93500.156*
H57B0.18741.02820.85780.156*
H57C0.25021.09820.96520.156*
H20.534 (2)0.648 (2)0.0388 (13)0.080*
H4B1.022 (2)0.296 (2)0.4955 (12)0.080*
H6A0.360 (2)0.878 (2)0.864 (2)0.080*
H40.805 (3)0.0608 (10)0.314 (2)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0485 (18)0.0647 (19)0.0694 (19)0.0107 (14)0.0166 (15)0.0283 (16)
N20.0452 (19)0.074 (2)0.0614 (18)0.0125 (15)0.0121 (15)0.0332 (17)
N30.0604 (19)0.079 (2)0.077 (2)0.0174 (17)0.0270 (16)0.0291 (19)
N40.069 (2)0.079 (2)0.0596 (19)0.0171 (18)0.0200 (15)0.0288 (19)
N50.069 (2)0.068 (2)0.086 (2)0.0205 (16)0.0315 (18)0.0263 (19)
N60.074 (2)0.079 (2)0.079 (2)0.0285 (17)0.0248 (19)0.040 (2)
O10.0634 (17)0.100 (2)0.0949 (19)0.0151 (17)0.0149 (15)0.0453 (17)
O20.0706 (17)0.129 (2)0.0769 (17)0.0049 (16)0.0023 (14)0.0630 (17)
O30.0570 (15)0.0951 (19)0.0648 (15)0.0035 (13)0.0030 (12)0.0374 (14)
O40.082 (2)0.121 (3)0.0783 (19)0.0030 (19)0.0182 (16)0.014 (2)
O50.0836 (19)0.124 (2)0.0684 (17)−0.0067 (17)0.0066 (15)0.0385 (17)
O60.0902 (18)0.0897 (19)0.0557 (15)0.0138 (15)0.0062 (13)0.0305 (14)
O70.120 (3)0.103 (3)0.181 (3)0.058 (2)0.066 (2)0.074 (3)
O80.0828 (19)0.095 (2)0.106 (2)0.0354 (16)0.0286 (15)0.0549 (17)
O90.0846 (18)0.092 (2)0.0844 (19)0.0358 (15)0.0275 (14)0.0402 (16)
C10.057 (2)0.047 (2)0.079 (3)0.0125 (18)0.028 (2)0.0156 (19)
C20.050 (2)0.053 (2)0.091 (3)0.0054 (18)0.017 (2)0.017 (2)
C30.055 (3)0.079 (3)0.120 (4)0.011 (2)0.020 (3)0.020 (3)
C40.063 (3)0.069 (3)0.147 (5)0.005 (2)0.042 (3)0.008 (3)
C50.084 (3)0.050 (2)0.134 (4)0.004 (2)0.070 (3)0.015 (3)
C60.128 (5)0.064 (3)0.191 (6)−0.004 (3)0.110 (5)0.011 (4)
C70.188 (7)0.077 (4)0.173 (6)0.009 (4)0.137 (6)0.029 (4)
C80.165 (5)0.089 (3)0.122 (4)0.021 (3)0.086 (4)0.044 (3)
C90.105 (3)0.070 (3)0.107 (3)0.006 (2)0.061 (3)0.032 (3)
C100.078 (3)0.051 (2)0.095 (3)0.011 (2)0.046 (2)0.016 (2)
C110.055 (2)0.055 (2)0.073 (2)0.0163 (18)0.0207 (19)0.0246 (19)
C120.060 (2)0.062 (2)0.056 (2)0.0113 (19)0.0129 (19)0.0262 (19)
C130.048 (2)0.055 (2)0.054 (2)0.0076 (16)0.0141 (17)0.0187 (17)
C140.055 (2)0.053 (2)0.067 (2)0.0122 (18)0.0198 (19)0.0198 (19)
C150.057 (3)0.068 (3)0.095 (3)0.014 (2)0.020 (2)0.026 (2)
C160.056 (3)0.070 (3)0.134 (4)0.010 (2)0.039 (3)0.022 (3)
C170.090 (3)0.084 (3)0.111 (4)0.013 (3)0.061 (3)0.033 (3)
C180.075 (3)0.069 (3)0.073 (2)0.014 (2)0.033 (2)0.028 (2)
C190.085 (3)0.088 (3)0.058 (2)0.009 (2)−0.010 (2)0.021 (2)
C200.049 (2)0.065 (3)0.066 (2)0.0104 (19)0.0232 (19)0.013 (2)
C210.062 (3)0.092 (4)0.084 (3)0.014 (2)0.029 (2)0.022 (3)
C220.074 (3)0.088 (4)0.110 (4)−0.004 (3)0.032 (3)−0.004 (3)
C230.072 (3)0.067 (3)0.160 (5)0.003 (2)0.047 (3)0.020 (4)
C240.056 (2)0.065 (3)0.123 (4)0.012 (2)0.037 (3)0.027 (3)
C250.091 (4)0.085 (4)0.180 (5)0.024 (3)0.066 (4)0.070 (4)
C260.117 (4)0.108 (5)0.165 (5)0.044 (3)0.077 (4)0.084 (4)
C270.106 (3)0.098 (4)0.106 (3)0.038 (3)0.043 (3)0.058 (3)
C280.085 (3)0.075 (3)0.081 (3)0.025 (2)0.033 (2)0.035 (3)
C290.056 (2)0.061 (3)0.092 (3)0.019 (2)0.038 (2)0.030 (2)
C300.060 (2)0.077 (3)0.067 (2)0.020 (2)0.0255 (19)0.027 (2)
C310.064 (3)0.095 (3)0.060 (2)0.025 (2)0.021 (2)0.035 (2)
C320.060 (2)0.077 (3)0.052 (2)0.021 (2)0.0194 (19)0.028 (2)
C330.069 (2)0.078 (3)0.057 (2)0.030 (2)0.024 (2)0.031 (2)
C340.074 (3)0.091 (3)0.072 (3)0.013 (2)0.020 (2)0.033 (2)
C350.085 (3)0.097 (3)0.094 (3)0.007 (3)0.031 (3)0.042 (3)
C360.091 (3)0.108 (4)0.089 (3)0.023 (3)0.034 (3)0.055 (3)
C370.072 (3)0.103 (3)0.064 (2)0.021 (2)0.021 (2)0.042 (2)
C380.094 (3)0.118 (3)0.052 (2)0.027 (3)0.000 (2)0.021 (2)
C390.055 (2)0.058 (3)0.093 (3)0.0151 (19)0.030 (2)0.014 (2)
C400.079 (3)0.071 (3)0.135 (4)0.018 (3)0.045 (3)0.027 (3)
C410.118 (4)0.073 (3)0.208 (7)0.031 (3)0.100 (5)0.022 (4)
C420.118 (5)0.083 (4)0.175 (6)0.000 (3)0.094 (5)−0.012 (4)
C430.071 (3)0.102 (4)0.095 (4)−0.003 (3)0.045 (3)−0.009 (3)
C440.085 (4)0.184 (6)0.095 (4)−0.016 (4)0.047 (4)−0.004 (4)
C450.089 (4)0.254 (8)0.090 (4)0.016 (4)0.044 (3)0.061 (5)
C460.093 (3)0.226 (6)0.115 (4)0.066 (4)0.057 (3)0.094 (4)
C470.078 (3)0.148 (4)0.089 (3)0.044 (3)0.039 (2)0.058 (3)
C480.049 (2)0.099 (3)0.074 (3)0.003 (2)0.020 (2)0.016 (3)
C490.065 (2)0.071 (3)0.085 (3)0.013 (2)0.023 (2)0.033 (2)
C500.061 (3)0.064 (3)0.089 (3)0.005 (2)0.019 (2)0.039 (2)
C510.069 (3)0.067 (3)0.074 (3)0.010 (2)0.019 (2)0.035 (2)
C520.070 (3)0.065 (3)0.075 (3)0.003 (2)0.022 (2)0.026 (2)
C530.086 (3)0.083 (3)0.086 (3)0.003 (2)0.023 (3)0.026 (3)
C540.106 (4)0.095 (4)0.088 (4)−0.001 (3)0.037 (3)0.018 (3)
C550.114 (4)0.112 (4)0.081 (3)0.001 (3)0.023 (3)0.043 (3)
C560.088 (3)0.098 (3)0.087 (3)0.011 (2)0.021 (3)0.045 (3)
C570.104 (3)0.115 (4)0.115 (3)0.063 (3)0.044 (3)0.054 (3)
Geometric parameters (Å, º) top
N1—C111.280 (3)C21—C221.416 (5)
N1—N21.375 (3)C22—C231.346 (5)
N2—C121.355 (4)C22—H220.9300
N2—H20.906 (10)C23—C241.411 (5)
N3—C301.283 (4)C23—H230.9300
N3—N41.376 (4)C24—C251.403 (5)
N4—C311.359 (4)C24—C291.412 (5)
N4—H4B0.906 (10)C25—C261.346 (6)
N5—C491.283 (4)C25—H250.9300
N5—N61.371 (4)C26—C271.396 (6)
N6—C501.361 (4)C26—H260.9300
N6—H6A0.887 (10)C27—C281.358 (4)
O1—C21.354 (4)C27—H270.9300
O1—H10.8200C28—C291.394 (4)
O2—C121.212 (3)C28—H280.9300
O3—C141.371 (3)C30—H300.9300
O3—C191.420 (3)C31—C321.485 (5)
O4—C211.343 (4)C32—C371.385 (4)
O4—H40.857 (10)C32—C331.399 (4)
O5—C311.223 (4)C33—C341.378 (4)
O6—C331.367 (3)C34—C351.374 (4)
O6—C381.438 (4)C34—H340.9300
O7—C401.350 (5)C35—C361.372 (5)
O7—H70.8200C35—H350.9300
O8—C501.233 (4)C36—C371.375 (5)
O9—C521.361 (4)C36—H360.9300
O9—C571.433 (4)C37—H370.9300
C1—C21.391 (4)C38—H38A0.9600
C1—C101.422 (4)C38—H38B0.9600
C1—C111.455 (4)C38—H38C0.9600
C2—C31.409 (5)C39—C401.375 (5)
C3—C41.335 (5)C39—C481.420 (5)
C3—H30.9300C39—C491.449 (5)
C4—C51.405 (5)C40—C411.410 (6)
C4—H4A0.9300C41—C421.336 (6)
C5—C61.387 (6)C41—H410.9300
C5—C101.426 (5)C42—C431.414 (6)
C6—C71.354 (6)C42—H420.9300
C6—H60.9300C43—C441.393 (6)
C7—C81.416 (7)C43—C481.416 (5)
C7—H7A0.9300C44—C451.352 (7)
C8—C91.370 (5)C44—H440.9300
C8—H80.9300C45—C461.396 (6)
C9—C101.413 (5)C45—H450.9300
C9—H90.9300C46—C471.368 (5)
C11—H110.9300C46—H460.9300
C12—C131.492 (4)C47—C481.394 (5)
C13—C141.390 (4)C47—H470.9300
C13—C181.393 (4)C49—H490.9300
C14—C151.382 (4)C50—C511.482 (5)
C15—C161.376 (5)C51—C561.381 (4)
C15—H150.9300C51—C521.391 (5)
C16—C171.366 (5)C52—C531.391 (5)
C16—H160.9300C53—C541.372 (5)
C17—C181.357 (5)C53—H530.9300
C17—H170.9300C54—C551.373 (5)
C18—H180.9300C54—H540.9300
C19—H19A0.9600C55—C561.374 (5)
C19—H19B0.9600C55—H550.9300
C19—H19C0.9600C56—H560.9300
C20—C211.389 (5)C57—H57A0.9600
C20—C291.432 (4)C57—H57B0.9600
C20—C301.438 (4)C57—H57C0.9600
C11—N1—N2117.2 (3)C28—C27—C26120.3 (4)
C12—N2—N1117.3 (3)C28—C27—H27119.8
C12—N2—H2122 (2)C26—C27—H27119.8
N1—N2—H2121 (2)C27—C28—C29122.0 (4)
C30—N3—N4119.5 (3)C27—C28—H28119.0
C31—N4—N3118.7 (3)C29—C28—H28119.0
C31—N4—H4B120 (2)C28—C29—C24117.0 (4)
N3—N4—H4B121 (2)C28—C29—C20123.2 (3)
C49—N5—N6118.6 (3)C24—C29—C20119.8 (4)
C50—N6—N5118.5 (3)N3—C30—C20120.1 (3)
C50—N6—H6A116 (2)N3—C30—H30120.0
N5—N6—H6A125 (2)C20—C30—H30120.0
C2—O1—H1109.5O5—C31—N4119.9 (4)
C14—O3—C19120.0 (3)O5—C31—C32121.7 (3)
C21—O4—H4112 (3)N4—C31—C32118.3 (3)
C33—O6—C38119.2 (3)C37—C32—C33117.6 (3)
C40—O7—H7109.5C37—C32—C31115.2 (3)
C52—O9—C57119.7 (3)C33—C32—C31127.1 (3)
C2—C1—C10118.7 (3)O6—C33—C34122.2 (3)
C2—C1—C11120.2 (3)O6—C33—C32117.2 (3)
C10—C1—C11121.1 (3)C34—C33—C32120.6 (3)
O1—C2—C1123.6 (3)C35—C34—C33120.6 (4)
O1—C2—C3115.3 (4)C35—C34—H34119.7
C1—C2—C3121.1 (4)C33—C34—H34119.7
C4—C3—C2119.9 (4)C36—C35—C34119.6 (4)
C4—C3—H3120.0C36—C35—H35120.2
C2—C3—H3120.0C34—C35—H35120.2
C3—C4—C5122.5 (4)C35—C36—C37120.2 (4)
C3—C4—H4A118.7C35—C36—H36119.9
C5—C4—H4A118.7C37—C36—H36119.9
C6—C5—C4123.0 (5)C36—C37—C32121.4 (4)
C6—C5—C10118.8 (5)C36—C37—H37119.3
C4—C5—C10118.2 (4)C32—C37—H37119.3
C7—C6—C5123.7 (6)O6—C38—H38A109.5
C7—C6—H6118.2O6—C38—H38B109.5
C5—C6—H6118.2H38A—C38—H38B109.5
C6—C7—C8117.9 (5)O6—C38—H38C109.5
C6—C7—H7A121.0H38A—C38—H38C109.5
C8—C7—H7A121.0H38B—C38—H38C109.5
C9—C8—C7120.7 (5)C40—C39—C48119.2 (4)
C9—C8—H8119.7C40—C39—C49119.4 (4)
C7—C8—H8119.7C48—C39—C49121.4 (4)
C8—C9—C10121.3 (4)O7—C40—C39123.9 (4)
C8—C9—H9119.4O7—C40—C41115.0 (5)
C10—C9—H9119.4C39—C40—C41121.1 (5)
C9—C10—C1122.7 (4)C42—C41—C40119.9 (6)
C9—C10—C5117.7 (4)C42—C41—H41120.1
C1—C10—C5119.6 (4)C40—C41—H41120.1
N1—C11—C1119.9 (3)C41—C42—C43121.8 (6)
N1—C11—H11120.1C41—C42—H42119.1
C1—C11—H11120.1C43—C42—H42119.1
O2—C12—N2121.6 (3)C44—C43—C42121.9 (6)
O2—C12—C13121.1 (3)C44—C43—C48119.4 (6)
N2—C12—C13117.3 (3)C42—C43—C48118.6 (5)
C14—C13—C18117.4 (3)C45—C44—C43121.7 (6)
C14—C13—C12127.2 (3)C45—C44—H44119.1
C18—C13—C12115.4 (3)C43—C44—H44119.1
O3—C14—C15122.0 (3)C44—C45—C46119.1 (6)
O3—C14—C13117.2 (3)C44—C45—H45120.5
C15—C14—C13120.8 (3)C46—C45—H45120.5
C16—C15—C14119.6 (4)C47—C46—C45120.7 (5)
C16—C15—H15120.2C47—C46—H46119.6
C14—C15—H15120.2C45—C46—H46119.6
C17—C16—C15120.5 (4)C46—C47—C48121.1 (4)
C17—C16—H16119.8C46—C47—H47119.5
C15—C16—H16119.8C48—C47—H47119.5
C18—C17—C16119.8 (4)C47—C48—C43117.9 (5)
C18—C17—H17120.1C47—C48—C39122.9 (4)
C16—C17—H17120.1C43—C48—C39119.2 (5)
C17—C18—C13121.9 (3)N5—C49—C39119.8 (4)
C17—C18—H18119.0N5—C49—H49120.1
C13—C18—H18119.0C39—C49—H49120.1
O3—C19—H19A109.5O8—C50—N6119.8 (4)
O3—C19—H19B109.5O8—C50—C51121.6 (4)
H19A—C19—H19B109.5N6—C50—C51118.7 (4)
O3—C19—H19C109.5C56—C51—C52118.2 (4)
H19A—C19—H19C109.5C56—C51—C50115.6 (4)
H19B—C19—H19C109.5C52—C51—C50126.2 (4)
C21—C20—C29119.0 (4)O9—C52—C53122.1 (4)
C21—C20—C30119.7 (4)O9—C52—C51117.6 (4)
C29—C20—C30121.3 (3)C53—C52—C51120.3 (4)
O4—C21—C20123.9 (4)C54—C53—C52119.6 (4)
O4—C21—C22115.7 (4)C54—C53—H53120.2
C20—C21—C22120.4 (4)C52—C53—H53120.2
C23—C22—C21120.3 (4)C53—C54—C55120.9 (5)
C23—C22—H22119.9C53—C54—H54119.6
C21—C22—H22119.9C55—C54—H54119.6
C22—C23—C24121.9 (4)C54—C55—C56119.2 (4)
C22—C23—H23119.0C54—C55—H55120.4
C24—C23—H23119.0C56—C55—H55120.4
C25—C24—C23121.3 (5)C55—C56—C51121.8 (4)
C25—C24—C29120.1 (4)C55—C56—H56119.1
C23—C24—C29118.6 (4)C51—C56—H56119.1
C26—C25—C24120.8 (5)O9—C57—H57A109.5
C26—C25—H25119.6O9—C57—H57B109.5
C24—C25—H25119.6H57A—C57—H57B109.5
C25—C26—C27119.7 (5)O9—C57—H57C109.5
C25—C26—H26120.1H57A—C57—H57C109.5
C27—C26—H26120.1H57B—C57—H57C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.842.556 (3)145
N2—H2···O30.91 (1)1.94 (2)2.622 (3)131 (3)
N2—H2···O8i0.91 (1)2.41 (2)3.094 (4)132 (2)
O4—H4···N30.86 (1)1.82 (2)2.538 (4)141 (3)
N4—H4B···O60.91 (1)1.95 (2)2.647 (4)132 (3)
O7—H7···N50.821.802.517 (4)146
N6—H6A···O90.89 (1)1.89 (2)2.621 (4)138 (3)
C11—H11···O8i0.932.463.122 (4)129
C38—H38B···O2ii0.962.353.090 (5)133
C57—H57B···O4iii0.962.563.435 (5)151
Symmetry codes: (i) x, y, z−1; (ii) −x+2, −y+1, −z+1; (iii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC19H16N2O3
Mr320.34
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)12.2266 (19), 14.212 (3), 15.805 (2)
α, β, γ (°)107.507 (3), 108.475 (3), 95.885 (3)
V (Å3)2423.9 (7)
Z6
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.23 × 0.23 × 0.21
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.980, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections		20059, 10353, 3438
Rint0.054
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.184, 0.94
No. of reflections10353
No. of parameters666
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.13, −0.15

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.842.556 (3)145
N2—H2···O30.906 (10)1.94 (2)2.622 (3)131 (3)
N2—H2···O8i0.906 (10)2.41 (2)3.094 (4)132 (2)
O4—H4···N30.857 (10)1.82 (2)2.538 (4)141 (3)
N4—H4B···O60.906 (10)1.95 (2)2.647 (4)132 (3)
O7—H7···N50.821.802.517 (4)146
N6—H6A···O90.887 (10)1.89 (2)2.621 (4)138 (3)
C11—H11···O8i0.932.463.122 (4)129
C38—H38B···O2ii0.962.353.090 (5)133
C57—H57B···O4iii0.962.563.435 (5)151
Symmetry codes: (i) x, y, z−1; (ii) −x+2, −y+1, −z+1; (iii) −x+1, −y+1, −z+1.
 

Acknowledgements

The author is grateful to the Zibo Vocational Institute for supporting this work.

References

First citationBruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationHashemian, S., Ghaeinee, V. & Notash, B. (2011). Acta Cryst. E67, o171.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationLei, Y. (2011). Acta Cryst. E67, o162.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationLi, H.-B. (2011a). Acta Cryst. E67, o1532.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationLi, X.-Y. (2011b). Acta Cryst. E67, o1798.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationLi, X.-Y. (2011c). Acta Cryst. E67, o2511.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationShalash, M., Salhin, A., Adnan, R., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o3126–o3127.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2713
https://doi.org/10.1107/S1600536811038153
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