Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039516/sj6169sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039516/sj6169Isup2.hkl |
CCDC reference: 296658
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.100
- wR factor = 0.183
- Data-to-parameter ratio = 9.6
checkCIF/PLATON results
No syntax errors found
Alert level C RFACG01_ALERT_3_C The value of the R factor is > 0.10 R factor given 0.100 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.62 PLAT147_ALERT_1_C su on Symmetry Constrained Cell Angle(s) ....... ? PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.48 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1B ... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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
1-(4-aminophenyl)ethanone (0.2 mmol, 27 mg) and isonicotinohydrazide (0.2 mmol, 27.4 mg) were dissolved in methanol (10 ml). The mixture was stirred at room temperature for 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; these were collected and washed three times with water.
All H atoms were initially located in a difference Fourier map and were refined freely with isotropic displacement parameters, giving N—H distances in the range 0.84 (5) to 0.87 (5) and C—H distances in the range 0.89 (5) to 1.01 (4) Å.
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.
C14H14N4O | F(000) = 536 |
Mr = 254.29 | Dx = 1.352 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1324 reflections |
a = 7.9137 (15) Å | θ = 5.2–53.9° |
b = 5.3466 (10) Å | µ = 0.09 mm−1 |
c = 29.650 (6) Å | T = 298 K |
β = 95.415 (3)° | Block, colourless |
V = 1248.9 (4) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 4 |
Bruker SMART APEX area-detector diffractometer | 2193 independent reflections |
Radiation source: fine-focus sealed tube | 1936 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −9→9 |
Tmin = 0.974, Tmax = 0.982 | k = −6→6 |
5756 measured reflections | l = −29→35 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.100 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.183 | All H-atom parameters refined |
S = 1.33 | w = 1/[σ2(Fo2) + (0.034P)2 + 1.5639P] where P = (Fo2 + 2Fc2)/3 |
2193 reflections | (Δ/σ)max < 0.001 |
228 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C14H14N4O | V = 1248.9 (4) Å3 |
Mr = 254.29 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.9137 (15) Å | µ = 0.09 mm−1 |
b = 5.3466 (10) Å | T = 298 K |
c = 29.650 (6) Å | 0.30 × 0.20 × 0.20 mm |
β = 95.415 (3)° |
Bruker SMART APEX area-detector diffractometer | 2193 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 1936 reflections with I > 2σ(I) |
Tmin = 0.974, Tmax = 0.982 | Rint = 0.043 |
5756 measured reflections |
R[F2 > 2σ(F2)] = 0.100 | 0 restraints |
wR(F2) = 0.183 | All H-atom parameters refined |
S = 1.33 | Δρmax = 0.31 e Å−3 |
2193 reflections | Δρmin = −0.23 e Å−3 |
228 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.7070 (5) | 0.6729 (6) | −0.00750 (10) | 0.0637 (10) | |
N1 | 0.9652 (7) | 0.6134 (9) | 0.26696 (13) | 0.0618 (13) | |
H1A | 1.021 (6) | 0.529 (9) | 0.2871 (16) | 0.058 (15)* | |
H1B | 0.896 (6) | 0.729 (9) | 0.2747 (15) | 0.055 (15)* | |
N2 | 0.7709 (4) | 0.3526 (6) | 0.06240 (10) | 0.0423 (9) | |
N3 | 0.7454 (5) | 0.2766 (7) | 0.01766 (11) | 0.0419 (9) | |
H3A | 0.749 (4) | 0.124 (7) | 0.0101 (12) | 0.025 (10)* | |
N4 | 0.6067 (5) | 0.1699 (7) | −0.14986 (11) | 0.0475 (9) | |
C1 | 0.8754 (5) | 0.2929 (7) | 0.13793 (12) | 0.0360 (9) | |
C2 | 0.7838 (6) | 0.4994 (8) | 0.15080 (14) | 0.0448 (11) | |
H2 | 0.705 (4) | 0.572 (6) | 0.1293 (12) | 0.029 (10)* | |
C3 | 0.8106 (6) | 0.6030 (8) | 0.19332 (14) | 0.0473 (11) | |
H3 | 0.742 (5) | 0.748 (8) | 0.1996 (13) | 0.044 (11)* | |
C4 | 0.9308 (6) | 0.5017 (8) | 0.22575 (13) | 0.0431 (11) | |
C5 | 1.0166 (6) | 0.2902 (9) | 0.21401 (14) | 0.0492 (12) | |
H5 | 1.089 (5) | 0.217 (7) | 0.2360 (14) | 0.043 (11)* | |
C6 | 0.9887 (6) | 0.1890 (8) | 0.17131 (14) | 0.0432 (11) | |
H6 | 1.059 (5) | 0.058 (8) | 0.1648 (13) | 0.045 (12)* | |
C7 | 0.8539 (5) | 0.2061 (7) | 0.09040 (12) | 0.0331 (9) | |
C8 | 0.9342 (8) | −0.0317 (11) | 0.07727 (19) | 0.0563 (14) | |
H8A | 0.856 (6) | −0.137 (9) | 0.0653 (17) | 0.070 (17)* | |
H8B | 1.010 (6) | 0.002 (9) | 0.0545 (17) | 0.072 (16)* | |
H8C | 1.004 (7) | −0.101 (10) | 0.1000 (18) | 0.087 (19)* | |
C9 | 0.7076 (5) | 0.4484 (8) | −0.01463 (13) | 0.0388 (10) | |
C10 | 0.6681 (5) | 0.3456 (7) | −0.06160 (12) | 0.0354 (9) | |
C11 | 0.7245 (6) | 0.4743 (8) | −0.09750 (14) | 0.0446 (11) | |
H11 | 0.791 (5) | 0.622 (8) | −0.0937 (13) | 0.045 (12)* | |
C12 | 0.6912 (6) | 0.3807 (9) | −0.14050 (14) | 0.0513 (12) | |
H12 | 0.735 (5) | 0.468 (7) | −0.1673 (13) | 0.043 (11)* | |
C13 | 0.5499 (6) | 0.0522 (9) | −0.11515 (15) | 0.0451 (11) | |
H13 | 0.484 (5) | −0.089 (7) | −0.1217 (12) | 0.031 (10)* | |
C14 | 0.5767 (6) | 0.1298 (8) | −0.07084 (14) | 0.0410 (10) | |
H14 | 0.537 (5) | 0.047 (7) | −0.0481 (13) | 0.042 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.109 (3) | 0.0379 (18) | 0.0410 (18) | 0.0120 (18) | −0.0096 (17) | −0.0044 (14) |
N1 | 0.094 (4) | 0.057 (3) | 0.033 (2) | 0.013 (3) | −0.003 (2) | −0.004 (2) |
N2 | 0.062 (2) | 0.0406 (19) | 0.0235 (17) | 0.0065 (18) | 0.0006 (15) | 0.0001 (15) |
N3 | 0.059 (2) | 0.035 (2) | 0.0315 (19) | 0.0073 (18) | 0.0002 (16) | −0.0042 (16) |
N4 | 0.055 (2) | 0.057 (2) | 0.0306 (19) | 0.008 (2) | 0.0054 (16) | −0.0012 (18) |
C1 | 0.040 (2) | 0.033 (2) | 0.036 (2) | −0.0015 (19) | 0.0057 (17) | 0.0018 (17) |
C2 | 0.048 (3) | 0.054 (3) | 0.032 (2) | 0.010 (2) | −0.0001 (19) | 0.008 (2) |
C3 | 0.063 (3) | 0.043 (3) | 0.036 (2) | 0.013 (2) | 0.008 (2) | 0.003 (2) |
C4 | 0.057 (3) | 0.047 (3) | 0.026 (2) | −0.002 (2) | 0.0060 (19) | 0.0016 (18) |
C5 | 0.059 (3) | 0.055 (3) | 0.032 (2) | 0.007 (2) | −0.004 (2) | 0.007 (2) |
C6 | 0.048 (3) | 0.042 (2) | 0.039 (2) | 0.008 (2) | 0.001 (2) | 0.004 (2) |
C7 | 0.038 (2) | 0.032 (2) | 0.030 (2) | −0.0043 (18) | 0.0090 (16) | −0.0046 (17) |
C8 | 0.067 (4) | 0.056 (3) | 0.043 (3) | 0.015 (3) | −0.006 (3) | −0.005 (3) |
C9 | 0.050 (3) | 0.034 (2) | 0.032 (2) | 0.0101 (19) | 0.0008 (18) | −0.0031 (18) |
C10 | 0.040 (2) | 0.034 (2) | 0.031 (2) | 0.0021 (19) | 0.0029 (16) | 0.0033 (17) |
C11 | 0.050 (3) | 0.042 (2) | 0.042 (3) | −0.005 (2) | 0.003 (2) | 0.001 (2) |
C12 | 0.067 (3) | 0.054 (3) | 0.034 (2) | −0.002 (3) | 0.007 (2) | 0.009 (2) |
C13 | 0.047 (3) | 0.043 (3) | 0.045 (3) | 0.001 (2) | −0.002 (2) | −0.002 (2) |
C14 | 0.051 (3) | 0.038 (2) | 0.034 (2) | 0.003 (2) | 0.0053 (19) | 0.0025 (19) |
O1—C9 | 1.219 (5) | C4—C5 | 1.381 (6) |
N1—C4 | 1.364 (5) | C5—C6 | 1.375 (6) |
N1—H1A | 0.84 (5) | C5—H5 | 0.91 (4) |
N1—H1B | 0.87 (5) | C6—H6 | 0.92 (4) |
N2—C7 | 1.277 (5) | C7—C8 | 1.489 (6) |
N2—N3 | 1.384 (4) | C8—H8A | 0.89 (5) |
N3—C9 | 1.340 (5) | C8—H8B | 0.96 (5) |
N3—H3A | 0.85 (4) | C8—H8C | 0.91 (6) |
N4—C13 | 1.321 (5) | C9—C10 | 1.503 (5) |
N4—C12 | 1.326 (6) | C10—C14 | 1.375 (5) |
C1—C6 | 1.387 (5) | C10—C11 | 1.377 (5) |
C1—C2 | 1.393 (6) | C11—C12 | 1.372 (6) |
C1—C7 | 1.478 (5) | C11—H11 | 0.95 (4) |
C2—C3 | 1.375 (6) | C12—H12 | 1.01 (4) |
C2—H2 | 0.93 (4) | C13—C14 | 1.375 (6) |
C3—C4 | 1.397 (6) | C13—H13 | 0.93 (4) |
C3—H3 | 0.97 (4) | C14—H14 | 0.89 (4) |
C4—N1—H1A | 117 (3) | N2—C7—C8 | 124.0 (4) |
C4—N1—H1B | 118 (3) | C1—C7—C8 | 120.2 (4) |
H1A—N1—H1B | 120 (4) | C7—C8—H8A | 110 (3) |
C7—N2—N3 | 117.5 (3) | C7—C8—H8B | 110 (3) |
C9—N3—N2 | 119.1 (3) | H8A—C8—H8B | 107 (4) |
C9—N3—H3A | 119 (2) | C7—C8—H8C | 113 (3) |
N2—N3—H3A | 122 (2) | H8A—C8—H8C | 113 (5) |
C13—N4—C12 | 116.3 (4) | H8B—C8—H8C | 103 (4) |
C6—C1—C2 | 116.1 (4) | O1—C9—N3 | 123.8 (4) |
C6—C1—C7 | 124.2 (4) | O1—C9—C10 | 121.1 (4) |
C2—C1—C7 | 119.6 (4) | N3—C9—C10 | 115.1 (3) |
C3—C2—C1 | 122.1 (4) | C14—C10—C11 | 117.9 (4) |
C3—C2—H2 | 120 (2) | C14—C10—C9 | 123.4 (4) |
C1—C2—H2 | 118 (2) | C11—C10—C9 | 118.6 (4) |
C2—C3—C4 | 120.7 (4) | C12—C11—C10 | 119.2 (4) |
C2—C3—H3 | 117 (2) | C12—C11—H11 | 118 (2) |
C4—C3—H3 | 122 (2) | C10—C11—H11 | 123 (2) |
N1—C4—C5 | 121.5 (4) | N4—C12—C11 | 123.6 (4) |
N1—C4—C3 | 120.8 (4) | N4—C12—H12 | 115 (2) |
C5—C4—C3 | 117.6 (4) | C11—C12—H12 | 121 (2) |
C6—C5—C4 | 120.9 (4) | N4—C13—C14 | 124.6 (4) |
C6—C5—H5 | 122 (3) | N4—C13—H13 | 117 (2) |
C4—C5—H5 | 117 (3) | C14—C13—H13 | 118 (2) |
C5—C6—C1 | 122.4 (4) | C13—C14—C10 | 118.3 (4) |
C5—C6—H6 | 116 (3) | C13—C14—H14 | 123 (3) |
C1—C6—H6 | 121 (2) | C10—C14—H14 | 119 (3) |
N2—C7—C1 | 115.6 (3) | ||
C7—N2—N3—C9 | −159.7 (4) | C2—C1—C7—C8 | −172.5 (4) |
C6—C1—C2—C3 | 3.5 (6) | N2—N3—C9—O1 | 6.0 (7) |
C7—C1—C2—C3 | −173.6 (4) | N2—N3—C9—C10 | −175.2 (3) |
C1—C2—C3—C4 | −0.8 (7) | O1—C9—C10—C14 | −142.3 (4) |
C2—C3—C4—N1 | 175.8 (4) | N3—C9—C10—C14 | 38.8 (6) |
C2—C3—C4—C5 | −2.2 (7) | O1—C9—C10—C11 | 37.0 (6) |
N1—C4—C5—C6 | −175.7 (4) | N3—C9—C10—C11 | −141.8 (4) |
C3—C4—C5—C6 | 2.3 (7) | C14—C10—C11—C12 | −1.5 (6) |
C4—C5—C6—C1 | 0.5 (7) | C9—C10—C11—C12 | 179.1 (4) |
C2—C1—C6—C5 | −3.4 (6) | C13—N4—C12—C11 | 1.7 (7) |
C7—C1—C6—C5 | 173.6 (4) | C10—C11—C12—N4 | −0.1 (7) |
N3—N2—C7—C1 | −179.0 (3) | C12—N4—C13—C14 | −1.9 (6) |
N3—N2—C7—C8 | 4.3 (6) | N4—C13—C14—C10 | 0.4 (7) |
C6—C1—C7—N2 | −166.3 (4) | C11—C10—C14—C13 | 1.3 (6) |
C2—C1—C7—N2 | 10.6 (5) | C9—C10—C14—C13 | −179.3 (4) |
C6—C1—C7—C8 | 10.6 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N4i | 0.84 (5) | 2.20 (5) | 3.018 (6) | 164 (4) |
N3—H3A···O1ii | 0.85 (4) | 2.48 (4) | 3.320 (5) | 169 (3) |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C14H14N4O |
Mr | 254.29 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 7.9137 (15), 5.3466 (10), 29.650 (6) |
β (°) | 95.415 (3) |
V (Å3) | 1248.9 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART APEX area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.974, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5756, 2193, 1936 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.100, 0.183, 1.33 |
No. of reflections | 2193 |
No. of parameters | 228 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.31, −0.23 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N4i | 0.84 (5) | 2.20 (5) | 3.018 (6) | 164 (4) |
N3—H3A···O1ii | 0.85 (4) | 2.48 (4) | 3.320 (5) | 169 (3) |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x, y−1, z. |
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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 1-(4-aminophenyl)ethanone.
In the title compound, (I) (Fig. 1), the C7═N2 bond, 1.277 (5) Å, and the C9—N3 bond, 1.340 (5) Å, are both shorter than normal because of conjugation effects. All other bond lengths are within normal ranges (Allen et al., 1987). The dihedral angle between the benzene and pyridine rings [73.1 (4)°] is significantly larger than normal (Shao et al., 2004) due to the steric effect of the C8 methyl substituent. The structure of (I) is stabilized by intermolecular N—H···N and N—H···O hydrogen bonds, forming chains along the c axis (Table 1 and Fig. 2).