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The title mol­ecule, C14H13N3O2, adopts a trans configuration with respect to the C=N double bond. There are two molecules in the asymmetric unit. The dihedral angles between the two rings are 39.1 (4) and 19.7 (4)°. In the crystal structure, inter­molecular N—H...O and N—H...N hydrogen bonds generate a network structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039504/sj6168sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039504/sj6168Isup2.hkl
Contains datablock I

CCDC reference: 296657

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.011 Å
  • R factor = 0.144
  • wR factor = 0.278
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.99 Deg. PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 11
Alert level C RFACG01_ALERT_3_C The value of the R factor is > 0.10 R factor given 0.144 RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.278 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT082_ALERT_2_C High R1 Value .................................. 0.14 PLAT084_ALERT_2_C High R2 Value .................................. 0.28 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.03 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Schiff base compounds have been of great interest for many years. These compounds play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions (Brunner et al., 1983), magnetism and molecular architectures (Miller et al., 2000). As an extension of work on the structural characterization of hydrazone Schiff base compounds (Shao et al., 2004), we report here the crystal structure of (I), a new isonicotinohydrazone with 2-methoxybenzaldehyde.

In the title compound, (I), which crystallizes with two unique molecules in the asymmetric unit (Fig. 1), the C—N bonds in the hydrazone units are characteristically short (Table 1) because of conjugation effects. All other bond lengths are within normal ranges (Allen et al., 1987). The dihedral angles between the benzene and pyridine rings are 39.1 (4)° (C1/C2/C3/N1/C4/C5 with C8/C9/C10/C11/C12/C13) and 19.7 (4)° (C15/C16/C17/N4/C18/C19 with C22/C23/C24/C25/C26/C27); these are slightly larger than normal (Fun et al., 1997) due to the steric effect of the C13 and C27 methoxyl substituents. The crystal structure is stabilized by intermolecular N—H···O and N—H···N hydrogen bonds (Table 2 and Fig. 2).

Experimental top

2-Methoxybenzaldehyde (0.2 mmol, 27.2 mg) and isonicotinohydrazide (0.2 mmol, 27.4 mg) were dissolved in methanol (10 ml). The mixture was stirred at room temperature for about 10 min. to give a clear yellow solution. The solution was set aside for 8 d. to allow slow evaporation of the solvent. Large colourless block-shaped crystals separated from the solution; these were collected and washed three times with water.

Refinement top

All the H atoms were placed in geometrically idealized positions (C—H 0.93 Å for aromatic H atoms, C—H 0.96 Å for methyl H atoms and N—H 0.86 Å), and constrained to ride on their parent atoms. They were treated as riding atoms, with Uiso(H) = 1.2Ueq(aromatic C,N) or 1.5Ueq (methyl C).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. The crystal packing of (I), viewed along the a axis. Dashed lines indicate intermolecular hydrogen bonds.
2-Methoxybenzaldehyde isonicotinoylhydrazone top
Crystal data top
C14H13N3O2F(000) = 1072
Mr = 255.27Dx = 1.256 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1047 reflections
a = 9.766 (2) Åθ = 4.9–35.8°
b = 15.935 (4) ŵ = 0.09 mm1
c = 17.428 (4) ÅT = 298 K
β = 95.404 (4)°Plate, colourless
V = 2700.1 (10) Å30.40 × 0.20 × 0.10 mm
Z = 8
Data collection top
Bruker SMART APEX area-detector
diffractometer
4742 independent reflections
Radiation source: fine-focus sealed tube2711 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.090
ϕ and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1111
Tmin = 0.966, Tmax = 0.991k = 1718
13018 measured reflectionsl = 2018
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)] = 0.144Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.278H-atom parameters constrained
S = 1.24 w = 1/[σ2(Fo2) + (0.0652P)2 + 1.9118P]
where P = (Fo2 + 2Fc2)/3
4742 reflections(Δ/σ)max = 0.007
345 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C14H13N3O2V = 2700.1 (10) Å3
Mr = 255.27Z = 8
Monoclinic, P21/cMo Kα radiation
a = 9.766 (2) ŵ = 0.09 mm1
b = 15.935 (4) ÅT = 298 K
c = 17.428 (4) Å0.40 × 0.20 × 0.10 mm
β = 95.404 (4)°
Data collection top
Bruker SMART APEX area-detector
diffractometer
4742 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
2711 reflections with I > 2σ(I)
Tmin = 0.966, Tmax = 0.991Rint = 0.090
13018 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.1440 restraints
wR(F2) = 0.278H-atom parameters constrained
S = 1.24Δρmax = 0.27 e Å3
4742 reflectionsΔρmin = 0.19 e Å3
345 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
O10.9712 (5)0.1291 (3)0.1523 (3)0.0633 (14)
O20.9032 (5)0.1310 (4)0.4449 (3)0.0850 (16)
O30.7864 (4)0.3931 (3)0.2393 (3)0.0649 (14)
O41.3172 (5)0.1379 (4)0.2976 (4)0.0947 (19)
N11.2620 (7)0.0437 (5)0.0064 (4)0.079 (2)
N21.0003 (5)0.0099 (3)0.2226 (3)0.0523 (14)
H2A1.03430.03990.22500.063*
N30.9289 (5)0.0387 (3)0.2809 (3)0.0564 (15)
N40.4246 (6)0.2252 (4)0.0912 (4)0.090 (2)
N50.8971 (5)0.2709 (3)0.2338 (3)0.0547 (15)
H5A0.89210.21840.22210.066*
N61.0168 (5)0.3038 (3)0.2676 (3)0.0544 (15)
C11.1036 (6)0.0194 (4)0.1044 (3)0.0388 (15)
C21.1959 (8)0.0692 (4)0.0722 (4)0.066 (2)
H2B1.20730.12510.08680.079*
C31.2716 (8)0.0349 (6)0.0176 (5)0.079 (2)
H31.33420.06960.00410.095*
C41.1710 (7)0.0889 (5)0.0246 (4)0.063 (2)
H41.15940.14390.00760.075*
C51.0899 (6)0.0619 (4)0.0808 (4)0.0489 (17)
H5B1.02840.09800.10170.059*
C61.0181 (6)0.0584 (4)0.1614 (4)0.0500 (18)
C70.9240 (6)0.0131 (4)0.3361 (4)0.0566 (18)
H70.96750.06480.33310.068*
C80.8528 (7)0.0057 (5)0.4036 (4)0.0598 (19)
C90.7950 (8)0.0829 (5)0.4155 (5)0.082 (2)
H90.79860.12460.37840.098*
C100.7323 (10)0.0995 (7)0.4812 (6)0.113 (3)
H100.69490.15200.48940.136*
C110.7263 (11)0.0363 (8)0.5343 (6)0.118 (4)
H110.68210.04650.57830.142*
C120.7821 (9)0.0402 (6)0.5251 (5)0.093 (3)
H120.77870.08110.56290.111*
C130.8443 (7)0.0568 (6)0.4589 (5)0.068 (2)
C140.8976 (9)0.1965 (5)0.5011 (5)0.106 (3)
H14A0.93390.24730.48150.159*
H14B0.80380.20530.51140.159*
H14C0.95120.18050.54780.159*
C150.6646 (6)0.2828 (4)0.1742 (4)0.0470 (16)
C160.5442 (6)0.3285 (4)0.1703 (4)0.0569 (19)
H160.54120.38000.19510.068*
C170.4288 (7)0.2966 (5)0.1291 (5)0.071 (2)
H170.34810.32770.12810.085*
C180.5417 (8)0.1854 (5)0.0941 (5)0.093 (3)
H180.54360.13620.06540.112*
C190.6618 (7)0.2086 (4)0.1350 (4)0.070 (2)
H190.73960.17470.13620.084*
C200.7883 (6)0.3202 (4)0.2190 (4)0.0484 (16)
C211.1161 (7)0.2524 (4)0.2778 (4)0.0562 (19)
H211.10050.19640.26460.067*
C221.2521 (7)0.2771 (4)0.3088 (4)0.0562 (19)
C231.2868 (7)0.3586 (5)0.3279 (4)0.074 (2)
H231.21840.39930.32240.089*
C241.4171 (8)0.3824 (6)0.3546 (5)0.088 (3)
H241.43850.43830.36560.106*
C251.5149 (8)0.3207 (7)0.3646 (5)0.091 (3)
H251.60330.33510.38500.109*
C261.4867 (8)0.2379 (6)0.3455 (5)0.086 (3)
H261.55560.19740.35110.104*
C271.3559 (7)0.2166 (5)0.3181 (4)0.069 (2)
C281.4202 (8)0.0773 (5)0.2895 (6)0.113 (3)
H28A1.37930.02790.26560.169*
H28B1.46410.06310.33950.169*
H28C1.48720.09960.25810.169*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.087 (3)0.036 (3)0.063 (3)0.015 (2)0.011 (3)0.004 (2)
O20.094 (4)0.080 (4)0.082 (4)0.011 (3)0.013 (3)0.009 (3)
O30.065 (3)0.041 (3)0.087 (4)0.001 (2)0.000 (3)0.019 (3)
O40.064 (3)0.077 (4)0.141 (6)0.009 (3)0.004 (3)0.014 (4)
N10.070 (4)0.102 (6)0.065 (5)0.001 (4)0.006 (4)0.021 (4)
N20.077 (4)0.029 (3)0.051 (4)0.023 (3)0.004 (3)0.001 (3)
N30.069 (4)0.053 (4)0.047 (4)0.015 (3)0.001 (3)0.011 (3)
N40.055 (4)0.083 (5)0.125 (7)0.018 (4)0.021 (4)0.019 (5)
N50.047 (3)0.042 (3)0.072 (4)0.004 (3)0.010 (3)0.019 (3)
N60.043 (3)0.055 (4)0.063 (4)0.009 (3)0.006 (3)0.013 (3)
C10.044 (3)0.031 (3)0.038 (4)0.003 (3)0.015 (3)0.005 (3)
C20.097 (6)0.050 (4)0.049 (5)0.009 (4)0.003 (4)0.004 (4)
C30.077 (6)0.096 (7)0.064 (6)0.021 (5)0.001 (5)0.007 (5)
C40.056 (5)0.063 (5)0.064 (5)0.010 (4)0.018 (4)0.018 (4)
C50.060 (4)0.041 (4)0.044 (4)0.000 (3)0.003 (3)0.006 (3)
C60.046 (4)0.035 (4)0.063 (5)0.007 (3)0.028 (4)0.003 (4)
C70.053 (4)0.056 (4)0.060 (5)0.012 (3)0.001 (4)0.010 (4)
C80.059 (4)0.070 (5)0.050 (5)0.004 (4)0.003 (4)0.010 (4)
C90.094 (6)0.092 (6)0.057 (6)0.031 (5)0.000 (5)0.003 (5)
C100.123 (8)0.129 (9)0.088 (8)0.025 (7)0.018 (7)0.042 (7)
C110.142 (9)0.161 (12)0.056 (7)0.016 (9)0.032 (6)0.001 (7)
C120.105 (7)0.114 (8)0.059 (6)0.002 (6)0.003 (5)0.001 (6)
C130.064 (5)0.093 (6)0.048 (5)0.007 (5)0.005 (4)0.012 (5)
C140.112 (7)0.106 (7)0.096 (7)0.017 (6)0.011 (6)0.040 (6)
C150.046 (4)0.049 (4)0.046 (4)0.001 (3)0.005 (3)0.006 (3)
C160.055 (4)0.050 (4)0.063 (5)0.003 (3)0.007 (4)0.005 (4)
C170.047 (4)0.066 (5)0.098 (7)0.001 (4)0.003 (4)0.015 (5)
C180.057 (5)0.099 (7)0.119 (8)0.016 (5)0.019 (5)0.043 (6)
C190.057 (4)0.064 (5)0.085 (6)0.003 (4)0.005 (4)0.029 (4)
C200.055 (4)0.042 (4)0.049 (4)0.006 (3)0.006 (3)0.006 (3)
C210.070 (5)0.052 (4)0.043 (4)0.004 (4)0.015 (4)0.007 (3)
C220.058 (4)0.067 (5)0.042 (4)0.012 (4)0.004 (4)0.015 (4)
C230.051 (4)0.095 (6)0.075 (6)0.008 (4)0.004 (4)0.028 (5)
C240.062 (5)0.125 (8)0.077 (6)0.022 (5)0.003 (5)0.032 (6)
C250.055 (5)0.148 (9)0.066 (6)0.018 (6)0.011 (4)0.024 (6)
C260.062 (5)0.117 (8)0.078 (6)0.005 (5)0.010 (5)0.010 (6)
C270.047 (4)0.082 (6)0.075 (6)0.004 (4)0.013 (4)0.008 (5)
C280.090 (6)0.068 (6)0.180 (11)0.026 (5)0.013 (7)0.023 (6)
Geometric parameters (Å, º) top
O1—C61.221 (6)C10—C111.372 (12)
O2—C131.346 (8)C10—H100.9300
O2—C141.434 (8)C11—C121.351 (11)
O3—C201.216 (6)C11—H110.9300
O4—C271.349 (8)C12—C131.379 (10)
O4—C281.411 (8)C12—H120.9300
N1—C41.300 (9)C14—H14A0.9600
N1—C31.322 (9)C14—H14B0.9600
N2—C61.340 (8)C14—H14C0.9600
N2—N31.366 (7)C15—C191.365 (8)
N2—H2A0.8600C15—C161.378 (8)
N3—C71.271 (8)C15—C201.498 (8)
N4—C181.305 (9)C16—C171.375 (8)
N4—C171.316 (9)C16—H160.9300
N5—C201.327 (7)C17—H170.9300
N5—N61.364 (6)C18—C191.365 (8)
N5—H5A0.8600C18—H180.9300
N6—C211.269 (7)C19—H190.9300
C1—C21.361 (9)C21—C221.441 (8)
C1—C51.363 (7)C21—H210.9300
C1—C61.492 (8)C22—C231.374 (9)
C2—C31.372 (10)C22—C271.397 (9)
C2—H2B0.9300C23—C241.367 (9)
C3—H30.9300C23—H230.9300
C4—C51.385 (9)C24—C251.371 (11)
C4—H40.9300C24—H240.9300
C5—H5B0.9300C25—C261.384 (11)
C7—C81.453 (9)C25—H250.9300
C7—H70.9300C26—C271.364 (9)
C8—C91.377 (9)C26—H260.9300
C8—C131.395 (10)C28—H28A0.9600
C9—C101.374 (11)C28—H28B0.9600
C9—H90.9300C28—H28C0.9600
C13—O2—C14118.1 (7)O2—C14—H14A109.5
C27—O4—C28118.6 (6)O2—C14—H14B109.5
C4—N1—C3115.1 (7)H14A—C14—H14B109.5
C6—N2—N3120.8 (5)O2—C14—H14C109.5
C6—N2—H2A119.6H14A—C14—H14C109.5
N3—N2—H2A119.6H14B—C14—H14C109.5
C7—N3—N2113.8 (5)C19—C15—C16117.1 (6)
C18—N4—C17114.5 (6)C19—C15—C20125.6 (6)
C20—N5—N6119.6 (5)C16—C15—C20117.3 (6)
C20—N5—H5A120.2C17—C16—C15118.9 (6)
N6—N5—H5A120.2C17—C16—H16120.5
C21—N6—N5115.1 (5)C15—C16—H16120.5
C2—C1—C5118.7 (6)N4—C17—C16124.6 (7)
C2—C1—C6117.8 (6)N4—C17—H17117.7
C5—C1—C6123.4 (6)C16—C17—H17117.7
C1—C2—C3118.3 (7)N4—C18—C19126.6 (8)
C1—C2—H2B120.8N4—C18—H18116.7
C3—C2—H2B120.8C19—C18—H18116.7
N1—C3—C2124.8 (8)C18—C19—C15118.1 (7)
N1—C3—H3117.6C18—C19—H19120.9
C2—C3—H3117.6C15—C19—H19120.9
N1—C4—C5125.6 (7)O3—C20—N5122.9 (6)
N1—C4—H4117.2O3—C20—C15119.8 (6)
C5—C4—H4117.2N5—C20—C15117.2 (6)
C1—C5—C4117.5 (6)N6—C21—C22122.7 (6)
C1—C5—H5B121.3N6—C21—H21118.6
C4—C5—H5B121.3C22—C21—H21118.6
O1—C6—N2124.1 (7)C23—C22—C27117.7 (6)
O1—C6—C1121.5 (6)C23—C22—C21123.1 (7)
N2—C6—C1114.4 (5)C27—C22—C21119.2 (6)
N3—C7—C8122.2 (6)C24—C23—C22123.0 (8)
N3—C7—H7118.9C24—C23—H23118.5
C8—C7—H7118.9C22—C23—H23118.5
C9—C8—C13118.8 (7)C23—C24—C25117.3 (8)
C9—C8—C7122.7 (7)C23—C24—H24121.3
C13—C8—C7118.5 (7)C25—C24—H24121.3
C10—C9—C8121.3 (9)C24—C25—C26122.2 (8)
C10—C9—H9119.4C24—C25—H25118.9
C8—C9—H9119.4C26—C25—H25118.9
C11—C10—C9118.1 (10)C27—C26—C25118.7 (8)
C11—C10—H10120.9C27—C26—H26120.7
C9—C10—H10120.9C25—C26—H26120.7
C12—C11—C10122.6 (10)O4—C27—C26123.6 (8)
C12—C11—H11118.7O4—C27—C22115.4 (6)
C10—C11—H11118.7C26—C27—C22121.0 (8)
C11—C12—C13119.1 (9)O4—C28—H28A109.5
C11—C12—H12120.4O4—C28—H28B109.5
C13—C12—H12120.4H28A—C28—H28B109.5
O2—C13—C12123.3 (8)O4—C28—H28C109.5
O2—C13—C8116.6 (7)H28A—C28—H28C109.5
C12—C13—C8120.1 (8)H28B—C28—H28C109.5
C6—N2—N3—C7178.0 (6)C7—C8—C13—C12177.5 (6)
C20—N5—N6—C21178.3 (6)C19—C15—C16—C171.3 (10)
C5—C1—C2—C30.4 (9)C20—C15—C16—C17179.4 (6)
C6—C1—C2—C3177.7 (6)C18—N4—C17—C161.0 (13)
C4—N1—C3—C21.4 (11)C15—C16—C17—N41.3 (12)
C1—C2—C3—N10.1 (11)C17—N4—C18—C193.6 (14)
C3—N1—C4—C52.3 (11)N4—C18—C19—C153.7 (14)
C2—C1—C5—C40.4 (8)C16—C15—C19—C181.0 (11)
C6—C1—C5—C4176.8 (5)C20—C15—C19—C18177.0 (7)
N1—C4—C5—C11.9 (10)N6—N5—C20—O35.6 (10)
N3—N2—C6—O11.6 (9)N6—N5—C20—C15173.6 (5)
N3—N2—C6—C1177.4 (5)C19—C15—C20—O3166.1 (7)
C2—C1—C6—O139.6 (8)C16—C15—C20—O311.8 (9)
C5—C1—C6—O1137.6 (6)C19—C15—C20—N513.1 (10)
C2—C1—C6—N2139.4 (6)C16—C15—C20—N5169.0 (6)
C5—C1—C6—N243.4 (8)N5—N6—C21—C22176.6 (6)
N2—N3—C7—C8180.0 (5)N6—C21—C22—C232.0 (11)
N3—C7—C8—C95.2 (10)N6—C21—C22—C27179.9 (7)
N3—C7—C8—C13175.6 (6)C27—C22—C23—C240.5 (11)
C13—C8—C9—C101.3 (12)C21—C22—C23—C24177.4 (7)
C7—C8—C9—C10177.9 (7)C22—C23—C24—C252.1 (12)
C8—C9—C10—C111.2 (14)C23—C24—C25—C263.0 (13)
C9—C10—C11—C121.5 (16)C24—C25—C26—C272.3 (13)
C10—C11—C12—C131.9 (16)C28—O4—C27—C2612.7 (12)
C14—O2—C13—C121.6 (11)C28—O4—C27—C22166.7 (7)
C14—O2—C13—C8179.4 (6)C25—C26—C27—O4179.8 (8)
C11—C12—C13—O2179.7 (8)C25—C26—C27—C220.6 (12)
C11—C12—C13—C82.0 (13)C23—C22—C27—O4179.1 (7)
C9—C8—C13—O2179.5 (6)C21—C22—C27—O41.0 (10)
C7—C8—C13—O20.3 (10)C23—C22—C27—C260.3 (11)
C9—C8—C13—C121.7 (11)C21—C22—C27—C26178.3 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O3i0.862.092.825 (6)143
N2—H2A···N6i0.862.553.294 (7)146
N5—H5A···O10.862.072.800 (6)142
Symmetry code: (i) x+2, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC14H13N3O2
Mr255.27
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)9.766 (2), 15.935 (4), 17.428 (4)
β (°) 95.404 (4)
V3)2700.1 (10)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.40 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART APEX area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.966, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
13018, 4742, 2711
Rint0.090
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.144, 0.278, 1.24
No. of reflections4742
No. of parameters345
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.19

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXL97.

Selected geometric parameters (Å, º) top
O1—C61.221 (6)N5—C201.327 (7)
O3—C201.216 (6)N5—N61.364 (6)
N2—C61.340 (8)N6—C211.269 (7)
N2—N31.366 (7)
C6—N2—N3120.8 (5)C21—N6—N5115.1 (5)
C7—N3—N2113.8 (5)O1—C6—N2124.1 (7)
C20—N5—N6119.6 (5)O3—C20—N5122.9 (6)
C6—N2—N3—C7178.0 (6)C7—C8—C13—O20.3 (10)
C20—N5—N6—C21178.3 (6)C21—C22—C27—O41.0 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O3i0.862.092.825 (6)143
N2—H2A···N6i0.862.553.294 (7)146
N5—H5A···O10.862.072.800 (6)142
Symmetry code: (i) x+2, y1/2, z+1/2.
 

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