Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039504/sj6168sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039504/sj6168Isup2.hkl |
CCDC reference: 296657
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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.
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).
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.
C14H13N3O2 | F(000) = 1072 |
Mr = 255.27 | Dx = 1.256 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1047 reflections |
a = 9.766 (2) Å | θ = 4.9–35.8° |
b = 15.935 (4) Å | µ = 0.09 mm−1 |
c = 17.428 (4) Å | T = 298 K |
β = 95.404 (4)° | Plate, colourless |
V = 2700.1 (10) Å3 | 0.40 × 0.20 × 0.10 mm |
Z = 8 |
Bruker SMART APEX area-detector diffractometer | 4742 independent reflections |
Radiation source: fine-focus sealed tube | 2711 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.090 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −11→11 |
Tmin = 0.966, Tmax = 0.991 | k = −17→18 |
13018 measured reflections | l = −20→18 |
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)] = 0.144 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.278 | H-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 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C14H13N3O2 | V = 2700.1 (10) Å3 |
Mr = 255.27 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.766 (2) Å | µ = 0.09 mm−1 |
b = 15.935 (4) Å | T = 298 K |
c = 17.428 (4) Å | 0.40 × 0.20 × 0.10 mm |
β = 95.404 (4)° |
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 = 0.991 | Rint = 0.090 |
13018 measured reflections |
R[F2 > 2σ(F2)] = 0.144 | 0 restraints |
wR(F2) = 0.278 | H-atom parameters constrained |
S = 1.24 | Δρmax = 0.27 e Å−3 |
4742 reflections | Δρmin = −0.19 e Å−3 |
345 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 | 0.9712 (5) | 0.1291 (3) | 0.1523 (3) | 0.0633 (14) | |
O2 | 0.9032 (5) | −0.1310 (4) | 0.4449 (3) | 0.0850 (16) | |
O3 | 0.7864 (4) | 0.3931 (3) | 0.2393 (3) | 0.0649 (14) | |
O4 | 1.3172 (5) | 0.1379 (4) | 0.2976 (4) | 0.0947 (19) | |
N1 | 1.2620 (7) | −0.0437 (5) | −0.0064 (4) | 0.079 (2) | |
N2 | 1.0003 (5) | 0.0099 (3) | 0.2226 (3) | 0.0523 (14) | |
H2A | 1.0343 | −0.0399 | 0.2250 | 0.063* | |
N3 | 0.9289 (5) | 0.0387 (3) | 0.2809 (3) | 0.0564 (15) | |
N4 | 0.4246 (6) | 0.2252 (4) | 0.0912 (4) | 0.090 (2) | |
N5 | 0.8971 (5) | 0.2709 (3) | 0.2338 (3) | 0.0547 (15) | |
H5A | 0.8921 | 0.2184 | 0.2221 | 0.066* | |
N6 | 1.0168 (5) | 0.3038 (3) | 0.2676 (3) | 0.0544 (15) | |
C1 | 1.1036 (6) | 0.0194 (4) | 0.1044 (3) | 0.0388 (15) | |
C2 | 1.1959 (8) | 0.0692 (4) | 0.0722 (4) | 0.066 (2) | |
H2B | 1.2073 | 0.1251 | 0.0868 | 0.079* | |
C3 | 1.2716 (8) | 0.0349 (6) | 0.0176 (5) | 0.079 (2) | |
H3 | 1.3342 | 0.0696 | −0.0041 | 0.095* | |
C4 | 1.1710 (7) | −0.0889 (5) | 0.0246 (4) | 0.063 (2) | |
H4 | 1.1594 | −0.1439 | 0.0076 | 0.075* | |
C5 | 1.0899 (6) | −0.0619 (4) | 0.0808 (4) | 0.0489 (17) | |
H5B | 1.0284 | −0.0980 | 0.1017 | 0.059* | |
C6 | 1.0181 (6) | 0.0584 (4) | 0.1614 (4) | 0.0500 (18) | |
C7 | 0.9240 (6) | −0.0131 (4) | 0.3361 (4) | 0.0566 (18) | |
H7 | 0.9675 | −0.0648 | 0.3331 | 0.068* | |
C8 | 0.8528 (7) | 0.0057 (5) | 0.4036 (4) | 0.0598 (19) | |
C9 | 0.7950 (8) | 0.0829 (5) | 0.4155 (5) | 0.082 (2) | |
H9 | 0.7986 | 0.1246 | 0.3784 | 0.098* | |
C10 | 0.7323 (10) | 0.0995 (7) | 0.4812 (6) | 0.113 (3) | |
H10 | 0.6949 | 0.1520 | 0.4894 | 0.136* | |
C11 | 0.7263 (11) | 0.0363 (8) | 0.5343 (6) | 0.118 (4) | |
H11 | 0.6821 | 0.0465 | 0.5783 | 0.142* | |
C12 | 0.7821 (9) | −0.0402 (6) | 0.5251 (5) | 0.093 (3) | |
H12 | 0.7787 | −0.0811 | 0.5629 | 0.111* | |
C13 | 0.8443 (7) | −0.0568 (6) | 0.4589 (5) | 0.068 (2) | |
C14 | 0.8976 (9) | −0.1965 (5) | 0.5011 (5) | 0.106 (3) | |
H14A | 0.9339 | −0.2473 | 0.4815 | 0.159* | |
H14B | 0.8038 | −0.2053 | 0.5114 | 0.159* | |
H14C | 0.9512 | −0.1805 | 0.5478 | 0.159* | |
C15 | 0.6646 (6) | 0.2828 (4) | 0.1742 (4) | 0.0470 (16) | |
C16 | 0.5442 (6) | 0.3285 (4) | 0.1703 (4) | 0.0569 (19) | |
H16 | 0.5412 | 0.3800 | 0.1951 | 0.068* | |
C17 | 0.4288 (7) | 0.2966 (5) | 0.1291 (5) | 0.071 (2) | |
H17 | 0.3481 | 0.3277 | 0.1281 | 0.085* | |
C18 | 0.5417 (8) | 0.1854 (5) | 0.0941 (5) | 0.093 (3) | |
H18 | 0.5436 | 0.1362 | 0.0654 | 0.112* | |
C19 | 0.6618 (7) | 0.2086 (4) | 0.1350 (4) | 0.070 (2) | |
H19 | 0.7396 | 0.1747 | 0.1362 | 0.084* | |
C20 | 0.7883 (6) | 0.3202 (4) | 0.2190 (4) | 0.0484 (16) | |
C21 | 1.1161 (7) | 0.2524 (4) | 0.2778 (4) | 0.0562 (19) | |
H21 | 1.1005 | 0.1964 | 0.2646 | 0.067* | |
C22 | 1.2521 (7) | 0.2771 (4) | 0.3088 (4) | 0.0562 (19) | |
C23 | 1.2868 (7) | 0.3586 (5) | 0.3279 (4) | 0.074 (2) | |
H23 | 1.2184 | 0.3993 | 0.3224 | 0.089* | |
C24 | 1.4171 (8) | 0.3824 (6) | 0.3546 (5) | 0.088 (3) | |
H24 | 1.4385 | 0.4383 | 0.3656 | 0.106* | |
C25 | 1.5149 (8) | 0.3207 (7) | 0.3646 (5) | 0.091 (3) | |
H25 | 1.6033 | 0.3351 | 0.3850 | 0.109* | |
C26 | 1.4867 (8) | 0.2379 (6) | 0.3455 (5) | 0.086 (3) | |
H26 | 1.5556 | 0.1974 | 0.3511 | 0.104* | |
C27 | 1.3559 (7) | 0.2166 (5) | 0.3181 (4) | 0.069 (2) | |
C28 | 1.4202 (8) | 0.0773 (5) | 0.2895 (6) | 0.113 (3) | |
H28A | 1.3793 | 0.0279 | 0.2656 | 0.169* | |
H28B | 1.4641 | 0.0631 | 0.3395 | 0.169* | |
H28C | 1.4872 | 0.0996 | 0.2581 | 0.169* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.087 (3) | 0.036 (3) | 0.063 (3) | 0.015 (2) | −0.011 (3) | −0.004 (2) |
O2 | 0.094 (4) | 0.080 (4) | 0.082 (4) | 0.011 (3) | 0.013 (3) | 0.009 (3) |
O3 | 0.065 (3) | 0.041 (3) | 0.087 (4) | −0.001 (2) | 0.000 (3) | −0.019 (3) |
O4 | 0.064 (3) | 0.077 (4) | 0.141 (6) | 0.009 (3) | −0.004 (3) | 0.014 (4) |
N1 | 0.070 (4) | 0.102 (6) | 0.065 (5) | −0.001 (4) | 0.006 (4) | −0.021 (4) |
N2 | 0.077 (4) | 0.029 (3) | 0.051 (4) | 0.023 (3) | 0.004 (3) | −0.001 (3) |
N3 | 0.069 (4) | 0.053 (4) | 0.047 (4) | 0.015 (3) | 0.001 (3) | −0.011 (3) |
N4 | 0.055 (4) | 0.083 (5) | 0.125 (7) | −0.018 (4) | −0.021 (4) | −0.019 (5) |
N5 | 0.047 (3) | 0.042 (3) | 0.072 (4) | −0.004 (3) | −0.010 (3) | −0.019 (3) |
N6 | 0.043 (3) | 0.055 (4) | 0.063 (4) | −0.009 (3) | −0.006 (3) | −0.013 (3) |
C1 | 0.044 (3) | 0.031 (3) | 0.038 (4) | 0.003 (3) | −0.015 (3) | 0.005 (3) |
C2 | 0.097 (6) | 0.050 (4) | 0.049 (5) | −0.009 (4) | −0.003 (4) | 0.004 (4) |
C3 | 0.077 (6) | 0.096 (7) | 0.064 (6) | −0.021 (5) | 0.001 (5) | 0.007 (5) |
C4 | 0.056 (5) | 0.063 (5) | 0.064 (5) | 0.010 (4) | −0.018 (4) | −0.018 (4) |
C5 | 0.060 (4) | 0.041 (4) | 0.044 (4) | 0.000 (3) | −0.003 (3) | −0.006 (3) |
C6 | 0.046 (4) | 0.035 (4) | 0.063 (5) | 0.007 (3) | −0.028 (4) | −0.003 (4) |
C7 | 0.053 (4) | 0.056 (4) | 0.060 (5) | 0.012 (3) | 0.001 (4) | −0.010 (4) |
C8 | 0.059 (4) | 0.070 (5) | 0.050 (5) | 0.004 (4) | 0.003 (4) | −0.010 (4) |
C9 | 0.094 (6) | 0.092 (6) | 0.057 (6) | 0.031 (5) | 0.000 (5) | −0.003 (5) |
C10 | 0.123 (8) | 0.129 (9) | 0.088 (8) | 0.025 (7) | 0.018 (7) | −0.042 (7) |
C11 | 0.142 (9) | 0.161 (12) | 0.056 (7) | 0.016 (9) | 0.032 (6) | −0.001 (7) |
C12 | 0.105 (7) | 0.114 (8) | 0.059 (6) | −0.002 (6) | 0.003 (5) | −0.001 (6) |
C13 | 0.064 (5) | 0.093 (6) | 0.048 (5) | −0.007 (5) | 0.005 (4) | −0.012 (5) |
C14 | 0.112 (7) | 0.106 (7) | 0.096 (7) | −0.017 (6) | −0.011 (6) | 0.040 (6) |
C15 | 0.046 (4) | 0.049 (4) | 0.046 (4) | −0.001 (3) | 0.005 (3) | 0.006 (3) |
C16 | 0.055 (4) | 0.050 (4) | 0.063 (5) | −0.003 (3) | −0.007 (4) | −0.005 (4) |
C17 | 0.047 (4) | 0.066 (5) | 0.098 (7) | 0.001 (4) | −0.003 (4) | 0.015 (5) |
C18 | 0.057 (5) | 0.099 (7) | 0.119 (8) | −0.016 (5) | −0.019 (5) | −0.043 (6) |
C19 | 0.057 (4) | 0.064 (5) | 0.085 (6) | −0.003 (4) | −0.005 (4) | −0.029 (4) |
C20 | 0.055 (4) | 0.042 (4) | 0.049 (4) | −0.006 (3) | 0.006 (3) | −0.006 (3) |
C21 | 0.070 (5) | 0.052 (4) | 0.043 (4) | −0.004 (4) | −0.015 (4) | −0.007 (3) |
C22 | 0.058 (4) | 0.067 (5) | 0.042 (4) | −0.012 (4) | −0.004 (4) | −0.015 (4) |
C23 | 0.051 (4) | 0.095 (6) | 0.075 (6) | −0.008 (4) | 0.004 (4) | −0.028 (5) |
C24 | 0.062 (5) | 0.125 (8) | 0.077 (6) | −0.022 (5) | 0.003 (5) | −0.032 (6) |
C25 | 0.055 (5) | 0.148 (9) | 0.066 (6) | −0.018 (6) | −0.011 (4) | −0.024 (6) |
C26 | 0.062 (5) | 0.117 (8) | 0.078 (6) | 0.005 (5) | −0.010 (5) | 0.010 (6) |
C27 | 0.047 (4) | 0.082 (6) | 0.075 (6) | −0.004 (4) | −0.013 (4) | 0.008 (5) |
C28 | 0.090 (6) | 0.068 (6) | 0.180 (11) | 0.026 (5) | 0.013 (7) | 0.023 (6) |
O1—C6 | 1.221 (6) | C10—C11 | 1.372 (12) |
O2—C13 | 1.346 (8) | C10—H10 | 0.9300 |
O2—C14 | 1.434 (8) | C11—C12 | 1.351 (11) |
O3—C20 | 1.216 (6) | C11—H11 | 0.9300 |
O4—C27 | 1.349 (8) | C12—C13 | 1.379 (10) |
O4—C28 | 1.411 (8) | C12—H12 | 0.9300 |
N1—C4 | 1.300 (9) | C14—H14A | 0.9600 |
N1—C3 | 1.322 (9) | C14—H14B | 0.9600 |
N2—C6 | 1.340 (8) | C14—H14C | 0.9600 |
N2—N3 | 1.366 (7) | C15—C19 | 1.365 (8) |
N2—H2A | 0.8600 | C15—C16 | 1.378 (8) |
N3—C7 | 1.271 (8) | C15—C20 | 1.498 (8) |
N4—C18 | 1.305 (9) | C16—C17 | 1.375 (8) |
N4—C17 | 1.316 (9) | C16—H16 | 0.9300 |
N5—C20 | 1.327 (7) | C17—H17 | 0.9300 |
N5—N6 | 1.364 (6) | C18—C19 | 1.365 (8) |
N5—H5A | 0.8600 | C18—H18 | 0.9300 |
N6—C21 | 1.269 (7) | C19—H19 | 0.9300 |
C1—C2 | 1.361 (9) | C21—C22 | 1.441 (8) |
C1—C5 | 1.363 (7) | C21—H21 | 0.9300 |
C1—C6 | 1.492 (8) | C22—C23 | 1.374 (9) |
C2—C3 | 1.372 (10) | C22—C27 | 1.397 (9) |
C2—H2B | 0.9300 | C23—C24 | 1.367 (9) |
C3—H3 | 0.9300 | C23—H23 | 0.9300 |
C4—C5 | 1.385 (9) | C24—C25 | 1.371 (11) |
C4—H4 | 0.9300 | C24—H24 | 0.9300 |
C5—H5B | 0.9300 | C25—C26 | 1.384 (11) |
C7—C8 | 1.453 (9) | C25—H25 | 0.9300 |
C7—H7 | 0.9300 | C26—C27 | 1.364 (9) |
C8—C9 | 1.377 (9) | C26—H26 | 0.9300 |
C8—C13 | 1.395 (10) | C28—H28A | 0.9600 |
C9—C10 | 1.374 (11) | C28—H28B | 0.9600 |
C9—H9 | 0.9300 | C28—H28C | 0.9600 |
C13—O2—C14 | 118.1 (7) | O2—C14—H14A | 109.5 |
C27—O4—C28 | 118.6 (6) | O2—C14—H14B | 109.5 |
C4—N1—C3 | 115.1 (7) | H14A—C14—H14B | 109.5 |
C6—N2—N3 | 120.8 (5) | O2—C14—H14C | 109.5 |
C6—N2—H2A | 119.6 | H14A—C14—H14C | 109.5 |
N3—N2—H2A | 119.6 | H14B—C14—H14C | 109.5 |
C7—N3—N2 | 113.8 (5) | C19—C15—C16 | 117.1 (6) |
C18—N4—C17 | 114.5 (6) | C19—C15—C20 | 125.6 (6) |
C20—N5—N6 | 119.6 (5) | C16—C15—C20 | 117.3 (6) |
C20—N5—H5A | 120.2 | C17—C16—C15 | 118.9 (6) |
N6—N5—H5A | 120.2 | C17—C16—H16 | 120.5 |
C21—N6—N5 | 115.1 (5) | C15—C16—H16 | 120.5 |
C2—C1—C5 | 118.7 (6) | N4—C17—C16 | 124.6 (7) |
C2—C1—C6 | 117.8 (6) | N4—C17—H17 | 117.7 |
C5—C1—C6 | 123.4 (6) | C16—C17—H17 | 117.7 |
C1—C2—C3 | 118.3 (7) | N4—C18—C19 | 126.6 (8) |
C1—C2—H2B | 120.8 | N4—C18—H18 | 116.7 |
C3—C2—H2B | 120.8 | C19—C18—H18 | 116.7 |
N1—C3—C2 | 124.8 (8) | C18—C19—C15 | 118.1 (7) |
N1—C3—H3 | 117.6 | C18—C19—H19 | 120.9 |
C2—C3—H3 | 117.6 | C15—C19—H19 | 120.9 |
N1—C4—C5 | 125.6 (7) | O3—C20—N5 | 122.9 (6) |
N1—C4—H4 | 117.2 | O3—C20—C15 | 119.8 (6) |
C5—C4—H4 | 117.2 | N5—C20—C15 | 117.2 (6) |
C1—C5—C4 | 117.5 (6) | N6—C21—C22 | 122.7 (6) |
C1—C5—H5B | 121.3 | N6—C21—H21 | 118.6 |
C4—C5—H5B | 121.3 | C22—C21—H21 | 118.6 |
O1—C6—N2 | 124.1 (7) | C23—C22—C27 | 117.7 (6) |
O1—C6—C1 | 121.5 (6) | C23—C22—C21 | 123.1 (7) |
N2—C6—C1 | 114.4 (5) | C27—C22—C21 | 119.2 (6) |
N3—C7—C8 | 122.2 (6) | C24—C23—C22 | 123.0 (8) |
N3—C7—H7 | 118.9 | C24—C23—H23 | 118.5 |
C8—C7—H7 | 118.9 | C22—C23—H23 | 118.5 |
C9—C8—C13 | 118.8 (7) | C23—C24—C25 | 117.3 (8) |
C9—C8—C7 | 122.7 (7) | C23—C24—H24 | 121.3 |
C13—C8—C7 | 118.5 (7) | C25—C24—H24 | 121.3 |
C10—C9—C8 | 121.3 (9) | C24—C25—C26 | 122.2 (8) |
C10—C9—H9 | 119.4 | C24—C25—H25 | 118.9 |
C8—C9—H9 | 119.4 | C26—C25—H25 | 118.9 |
C11—C10—C9 | 118.1 (10) | C27—C26—C25 | 118.7 (8) |
C11—C10—H10 | 120.9 | C27—C26—H26 | 120.7 |
C9—C10—H10 | 120.9 | C25—C26—H26 | 120.7 |
C12—C11—C10 | 122.6 (10) | O4—C27—C26 | 123.6 (8) |
C12—C11—H11 | 118.7 | O4—C27—C22 | 115.4 (6) |
C10—C11—H11 | 118.7 | C26—C27—C22 | 121.0 (8) |
C11—C12—C13 | 119.1 (9) | O4—C28—H28A | 109.5 |
C11—C12—H12 | 120.4 | O4—C28—H28B | 109.5 |
C13—C12—H12 | 120.4 | H28A—C28—H28B | 109.5 |
O2—C13—C12 | 123.3 (8) | O4—C28—H28C | 109.5 |
O2—C13—C8 | 116.6 (7) | H28A—C28—H28C | 109.5 |
C12—C13—C8 | 120.1 (8) | H28B—C28—H28C | 109.5 |
C6—N2—N3—C7 | −178.0 (6) | C7—C8—C13—C12 | 177.5 (6) |
C20—N5—N6—C21 | −178.3 (6) | C19—C15—C16—C17 | 1.3 (10) |
C5—C1—C2—C3 | −0.4 (9) | C20—C15—C16—C17 | 179.4 (6) |
C6—C1—C2—C3 | −177.7 (6) | C18—N4—C17—C16 | −1.0 (13) |
C4—N1—C3—C2 | 1.4 (11) | C15—C16—C17—N4 | −1.3 (12) |
C1—C2—C3—N1 | −0.1 (11) | C17—N4—C18—C19 | 3.6 (14) |
C3—N1—C4—C5 | −2.3 (11) | N4—C18—C19—C15 | −3.7 (14) |
C2—C1—C5—C4 | −0.4 (8) | C16—C15—C19—C18 | 1.0 (11) |
C6—C1—C5—C4 | 176.8 (5) | C20—C15—C19—C18 | −177.0 (7) |
N1—C4—C5—C1 | 1.9 (10) | N6—N5—C20—O3 | −5.6 (10) |
N3—N2—C6—O1 | −1.6 (9) | N6—N5—C20—C15 | 173.6 (5) |
N3—N2—C6—C1 | 177.4 (5) | C19—C15—C20—O3 | 166.1 (7) |
C2—C1—C6—O1 | 39.6 (8) | C16—C15—C20—O3 | −11.8 (9) |
C5—C1—C6—O1 | −137.6 (6) | C19—C15—C20—N5 | −13.1 (10) |
C2—C1—C6—N2 | −139.4 (6) | C16—C15—C20—N5 | 169.0 (6) |
C5—C1—C6—N2 | 43.4 (8) | N5—N6—C21—C22 | 176.6 (6) |
N2—N3—C7—C8 | −180.0 (5) | N6—C21—C22—C23 | −2.0 (11) |
N3—C7—C8—C9 | −5.2 (10) | N6—C21—C22—C27 | −179.9 (7) |
N3—C7—C8—C13 | 175.6 (6) | C27—C22—C23—C24 | 0.5 (11) |
C13—C8—C9—C10 | 1.3 (12) | C21—C22—C23—C24 | −177.4 (7) |
C7—C8—C9—C10 | −177.9 (7) | C22—C23—C24—C25 | −2.1 (12) |
C8—C9—C10—C11 | −1.2 (14) | C23—C24—C25—C26 | 3.0 (13) |
C9—C10—C11—C12 | 1.5 (16) | C24—C25—C26—C27 | −2.3 (13) |
C10—C11—C12—C13 | −1.9 (16) | C28—O4—C27—C26 | −12.7 (12) |
C14—O2—C13—C12 | 1.6 (11) | C28—O4—C27—C22 | 166.7 (7) |
C14—O2—C13—C8 | 179.4 (6) | C25—C26—C27—O4 | 179.8 (8) |
C11—C12—C13—O2 | 179.7 (8) | C25—C26—C27—C22 | 0.6 (12) |
C11—C12—C13—C8 | 2.0 (13) | C23—C22—C27—O4 | −179.1 (7) |
C9—C8—C13—O2 | −179.5 (6) | C21—C22—C27—O4 | −1.0 (10) |
C7—C8—C13—O2 | −0.3 (10) | C23—C22—C27—C26 | 0.3 (11) |
C9—C8—C13—C12 | −1.7 (11) | C21—C22—C27—C26 | 178.3 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O3i | 0.86 | 2.09 | 2.825 (6) | 143 |
N2—H2A···N6i | 0.86 | 2.55 | 3.294 (7) | 146 |
N5—H5A···O1 | 0.86 | 2.07 | 2.800 (6) | 142 |
Symmetry code: (i) −x+2, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H13N3O2 |
Mr | 255.27 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 9.766 (2), 15.935 (4), 17.428 (4) |
β (°) | 95.404 (4) |
V (Å3) | 2700.1 (10) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.40 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEX area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.966, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13018, 4742, 2711 |
Rint | 0.090 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.144, 0.278, 1.24 |
No. of reflections | 4742 |
No. of parameters | 345 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.19 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXL97.
O1—C6 | 1.221 (6) | N5—C20 | 1.327 (7) |
O3—C20 | 1.216 (6) | N5—N6 | 1.364 (6) |
N2—C6 | 1.340 (8) | N6—C21 | 1.269 (7) |
N2—N3 | 1.366 (7) | ||
C6—N2—N3 | 120.8 (5) | C21—N6—N5 | 115.1 (5) |
C7—N3—N2 | 113.8 (5) | O1—C6—N2 | 124.1 (7) |
C20—N5—N6 | 119.6 (5) | O3—C20—N5 | 122.9 (6) |
C6—N2—N3—C7 | −178.0 (6) | C7—C8—C13—O2 | −0.3 (10) |
C20—N5—N6—C21 | −178.3 (6) | C21—C22—C27—O4 | −1.0 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O3i | 0.86 | 2.09 | 2.825 (6) | 143 |
N2—H2A···N6i | 0.86 | 2.55 | 3.294 (7) | 146 |
N5—H5A···O1 | 0.86 | 2.07 | 2.800 (6) | 142 |
Symmetry code: (i) −x+2, y−1/2, −z+1/2. |
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).