Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703053X/rz2140sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680703053X/rz2140Isup2.hkl |
CCDC reference: 298860
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- Disorder in main residue
- R factor = 0.058
- wR factor = 0.124
- Data-to-parameter ratio = 12.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 34 Perc.
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N10' PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N5 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C29 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.06 PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7 PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C22 - C23 ... 1.37 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C23 - C24 ... 1.36 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C15 - C19 ... 1.42 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C17 - C20 ... 1.43 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C6 ... 1.42 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C4 - C7 ... 1.42 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O6' .. C1 .. 2.99 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C1 .. O6 .. 2.95 Ang.
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 160
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 11 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For general background, see: Boeckman et al. (1987); Comins et al. (1994); Cox & O'Hagan (1991); Deshang et al. (1988); Kozikowski et al. (1996); Li et al. (2000); Nagarajan et al. (2003).
The title Compound was prepared by the reaction of 2-cyanoacetamide (2 mmol), malononitrile (2 mmol) and 3-nitrobenzaldehyde (2 mmol) in water (2 ml). Single crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a 95% aqueous ethanol solution (yield 48%; m.p. >573 K). IR (cm-1): 3546, 3338, 3189, 2214, 1670, 1646, 1529; 1H NMR (DMSO-d6): 7.87 (2H, brs, NH2), 7.88–8.01 (4H, m, ArH), 11.85 (1H, s, NH).
All H atoms were positioned geometrically and treated as riding, with N—H = 0.86 Å, O—H = 0.82 Å and C—H = 0.93–0.97 Å, and with Uiso(H) = 1.2 Ueq(C, N) or 1.5 Ueq(C, O) for methyl and hydroxy groups.
The synthesis of 2-pyridone derivatives is an area of growing interest because compounds with these scaffolds exhibited significant pharmacological properties such as antibacterial (Li et al., 2000), antifungal (Cox & O'Hagan, 1991) and antitumor activity (Nagarajan et al., 2003). These compounds have been used also as cardiotonic (Deshang et al., 1988) and psychotherapeutic agents (Kozikowski et al., 1996) and potential HIC-1 specific transcriptase inhibitors (Boeckman et al., 1987). Moreover it is well know that the 2-pyridone ring system is a valuable building block in the symthesis of natural products (Comins et al., 1994). For these reasons, the synthesis of new compounds containing 2-pyridone derivatives is strongly desired. In this paper we report the crystal structure of the title compound.
In the asymmetric units there are two title molecules of similar geometry and two ethanol molecules (Fig. 1). One nitro group is disordered over two positions, with refined site occupation factors of 0.688 (17) and 0.312 (17) for the major and minor components, respectively. The dihedral angle between the C1/C2/C3/C4/C5/N1 plane and the C8—C13 benzene ring is 52.06 (11) °, while the corresponding angle between the C14/C15/C16/C17/C18/N6 plane and the C21—C26 benzene ring is 65.12 (13)°. The crystal packing is stabilized by an extended network of N—H···O, N—H···N, O—H···O and C—H···O intra- and intermolecular hydrogen bonds (Table 1, Fig. 2).
For general background, see: Boeckman et al. (1987); Comins et al. (1994); Cox & O'Hagan (1991); Deshang et al. (1988); Kozikowski et al. (1996); Li et al. (2000); Nagarajan et al. (2003).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); 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, 1999); software used to prepare material for publication: SHELXTL.
C13H7N5O3·C2H6O | F(000) = 1360 |
Mr = 327.30 | Dx = 1.349 Mg m−3 |
Monoclinic, P21/n | Melting point > 573 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 13.079 (3) Å | Cell parameters from 1628 reflections |
b = 14.764 (4) Å | θ = 2.4–19,693° |
c = 16.693 (4) Å | µ = 0.10 mm−1 |
β = 90.923 (4)° | T = 298 K |
V = 3223.0 (14) Å3 | Block, yellow |
Z = 8 | 0.45 × 0.36 × 0.31 mm |
Bruker SMART CCD area-detector diffractometer | 5690 independent reflections |
Radiation source: fine-focus sealed tube | 1952 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.089 |
φ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→15 |
Tmin = 0.950, Tmax = 0.962 | k = −15→17 |
16780 measured reflections | l = −19→16 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0257P)2] where P = (Fo2 + 2Fc2)/3 |
5690 reflections | (Δ/σ)max < 0.001 |
465 parameters | Δρmax = 0.38 e Å−3 |
160 restraints | Δρmin = −0.33 e Å−3 |
C13H7N5O3·C2H6O | V = 3223.0 (14) Å3 |
Mr = 327.30 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.079 (3) Å | µ = 0.10 mm−1 |
b = 14.764 (4) Å | T = 298 K |
c = 16.693 (4) Å | 0.45 × 0.36 × 0.31 mm |
β = 90.923 (4)° |
Bruker SMART CCD area-detector diffractometer | 5690 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1952 reflections with I > 2σ(I) |
Tmin = 0.950, Tmax = 0.962 | Rint = 0.089 |
16780 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 160 restraints |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.38 e Å−3 |
5690 reflections | Δρmin = −0.33 e Å−3 |
465 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 | Occ. (<1) | |
N1 | 0.5413 (2) | −0.0007 (2) | 0.88884 (17) | 0.0437 (9) | |
H1 | 0.5749 | −0.0469 | 0.9064 | 0.052* | |
N2 | 0.6368 (3) | 0.2644 (3) | 0.7473 (2) | 0.0869 (14) | |
N3 | 0.1889 (3) | 0.0708 (2) | 0.8869 (2) | 0.0649 (11) | |
N4 | 0.3967 (2) | −0.0744 (2) | 0.92758 (17) | 0.0535 (10) | |
H4A | 0.4351 | −0.1178 | 0.9448 | 0.064* | |
H4B | 0.3315 | −0.0780 | 0.9321 | 0.064* | |
N5 | 0.3662 (4) | 0.4712 (3) | 0.8369 (3) | 0.0937 (16) | |
N6 | 0.6783 (2) | 0.4244 (2) | 0.59015 (17) | 0.0485 (9) | |
H6 | 0.7123 | 0.4700 | 0.6084 | 0.058* | |
N7 | 0.7718 (3) | 0.1339 (3) | 0.4923 (2) | 0.0779 (13) | |
N8 | 0.3234 (3) | 0.3745 (2) | 0.5484 (2) | 0.0711 (12) | |
N9 | 0.5327 (2) | 0.5071 (2) | 0.61243 (18) | 0.0612 (10) | |
H9A | 0.5706 | 0.5513 | 0.6288 | 0.073* | |
H9B | 0.4673 | 0.5127 | 0.6117 | 0.073* | |
N10 | 0.447 (3) | 0.099 (3) | 0.305 (2) | 0.107 (9) | 0.312 (17) |
N10' | 0.4599 (12) | 0.0567 (11) | 0.3306 (8) | 0.098 (4) | 0.688 (17) |
O1 | 0.69115 (19) | 0.06659 (18) | 0.85852 (15) | 0.0582 (8) | |
O2 | 0.4461 (4) | 0.4791 (3) | 0.8736 (3) | 0.1390 (18) | |
O3 | 0.3055 (3) | 0.5318 (3) | 0.8276 (2) | 0.1389 (18) | |
O4 | 0.82853 (19) | 0.35442 (18) | 0.56654 (15) | 0.0615 (9) | |
O5 | 0.4957 (16) | 0.1407 (14) | 0.2640 (11) | 0.097 (6) | 0.312 (17) |
O6 | 0.3707 (16) | 0.0454 (18) | 0.2843 (11) | 0.128 (7) | 0.312 (17) |
O5' | 0.5210 (8) | 0.0869 (12) | 0.2864 (7) | 0.136 (4) | 0.688 (17) |
O6' | 0.4135 (8) | −0.0099 (8) | 0.3139 (6) | 0.137 (4) | 0.688 (17) |
O7 | 0.0021 (2) | 0.2717 (2) | 0.5108 (2) | 0.0806 (10) | |
H7 | −0.0559 | 0.2762 | 0.5283 | 0.121* | |
O8 | 0.6269 (2) | 0.6604 (3) | 0.6769 (2) | 0.1075 (13) | |
H8 | 0.6889 | 0.6636 | 0.6709 | 0.161* | |
C1 | 0.5962 (3) | 0.0702 (3) | 0.8570 (2) | 0.0447 (11) | |
C2 | 0.5381 (3) | 0.1436 (3) | 0.8234 (2) | 0.0431 (11) | |
C3 | 0.4334 (3) | 0.1448 (3) | 0.8294 (2) | 0.0408 (10) | |
C4 | 0.3825 (3) | 0.0726 (3) | 0.8654 (2) | 0.0400 (10) | |
C5 | 0.4381 (3) | −0.0024 (3) | 0.8943 (2) | 0.0406 (11) | |
C6 | 0.5925 (3) | 0.2113 (3) | 0.7813 (3) | 0.0572 (13) | |
C7 | 0.2748 (3) | 0.0719 (3) | 0.8769 (2) | 0.0459 (11) | |
C8 | 0.3733 (3) | 0.2238 (3) | 0.8012 (2) | 0.0466 (11) | |
C9 | 0.3988 (3) | 0.3087 (3) | 0.8279 (2) | 0.0544 (12) | |
H9 | 0.4558 | 0.3170 | 0.8612 | 0.065* | |
C10 | 0.3397 (4) | 0.3813 (3) | 0.8054 (3) | 0.0634 (14) | |
C11 | 0.2560 (4) | 0.3732 (4) | 0.7573 (3) | 0.0808 (17) | |
H11 | 0.2168 | 0.4236 | 0.7438 | 0.097* | |
C12 | 0.2302 (4) | 0.2888 (4) | 0.7289 (3) | 0.0791 (16) | |
H12 | 0.1734 | 0.2818 | 0.6953 | 0.095* | |
C13 | 0.2886 (3) | 0.2144 (3) | 0.7503 (2) | 0.0628 (13) | |
H13 | 0.2711 | 0.1575 | 0.7305 | 0.075* | |
C14 | 0.7335 (3) | 0.3502 (3) | 0.5651 (2) | 0.0453 (11) | |
C15 | 0.6741 (3) | 0.2752 (3) | 0.5383 (2) | 0.0445 (11) | |
C16 | 0.5687 (3) | 0.2784 (3) | 0.5358 (2) | 0.0424 (11) | |
C17 | 0.5190 (3) | 0.3557 (3) | 0.5605 (2) | 0.0430 (11) | |
C18 | 0.5750 (3) | 0.4312 (3) | 0.5884 (2) | 0.0449 (11) | |
C19 | 0.7282 (3) | 0.1969 (3) | 0.5126 (3) | 0.0547 (13) | |
C20 | 0.4105 (3) | 0.3644 (3) | 0.5539 (2) | 0.0507 (12) | |
C21 | 0.5069 (3) | 0.1995 (3) | 0.5085 (3) | 0.0462 (11) | |
C22 | 0.5108 (3) | 0.1706 (3) | 0.4295 (3) | 0.0638 (14) | |
H22 | 0.5532 | 0.1988 | 0.3929 | 0.077* | |
C23 | 0.4500 (4) | 0.0988 (4) | 0.4074 (3) | 0.0753 (16) | |
C24 | 0.3867 (4) | 0.0549 (3) | 0.4580 (4) | 0.0872 (19) | |
H24 | 0.3459 | 0.0073 | 0.4398 | 0.105* | |
C25 | 0.3839 (3) | 0.0819 (3) | 0.5366 (4) | 0.0821 (16) | |
H25 | 0.3425 | 0.0523 | 0.5730 | 0.098* | |
C26 | 0.4444 (3) | 0.1545 (3) | 0.5604 (3) | 0.0621 (13) | |
H26 | 0.4426 | 0.1733 | 0.6136 | 0.074* | |
C27 | 0.0420 (4) | 0.1856 (4) | 0.5300 (3) | 0.0975 (18) | |
H27A | −0.0073 | 0.1394 | 0.5149 | 0.117* | |
H27B | 0.0540 | 0.1816 | 0.5874 | 0.117* | |
C28 | 0.1378 (4) | 0.1693 (4) | 0.4885 (3) | 0.140 (2) | |
H28A | 0.1244 | 0.1647 | 0.4320 | 0.210* | |
H28B | 0.1679 | 0.1139 | 0.5076 | 0.210* | |
H28C | 0.1841 | 0.2186 | 0.4988 | 0.210* | |
C29 | 0.6040 (6) | 0.6753 (5) | 0.7591 (5) | 0.180 (4) | |
H29A | 0.5308 | 0.6793 | 0.7670 | 0.216* | |
H29B | 0.6364 | 0.7300 | 0.7792 | 0.216* | |
C30 | 0.6487 (6) | 0.5913 (5) | 0.7994 (5) | 0.210 (4) | |
H30A | 0.6229 | 0.5381 | 0.7729 | 0.315* | |
H30B | 0.6295 | 0.5902 | 0.8546 | 0.315* | |
H30C | 0.7219 | 0.5927 | 0.7960 | 0.315* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.035 (2) | 0.043 (2) | 0.053 (2) | 0.0012 (18) | −0.0031 (17) | 0.0028 (17) |
N2 | 0.075 (3) | 0.077 (4) | 0.109 (4) | −0.005 (3) | 0.027 (3) | 0.023 (3) |
N3 | 0.038 (2) | 0.068 (3) | 0.088 (3) | 0.005 (2) | 0.008 (2) | 0.008 (2) |
N4 | 0.0299 (19) | 0.057 (3) | 0.074 (3) | 0.0025 (19) | −0.0017 (18) | 0.007 (2) |
N5 | 0.120 (5) | 0.046 (4) | 0.116 (4) | 0.016 (4) | 0.017 (4) | 0.005 (3) |
N6 | 0.032 (2) | 0.050 (3) | 0.063 (2) | −0.0055 (19) | −0.0007 (18) | −0.0132 (19) |
N7 | 0.061 (3) | 0.071 (3) | 0.101 (3) | 0.006 (2) | 0.012 (2) | −0.017 (3) |
N8 | 0.036 (2) | 0.072 (3) | 0.105 (3) | 0.001 (2) | 0.008 (2) | −0.022 (2) |
N9 | 0.035 (2) | 0.058 (3) | 0.092 (3) | 0.0023 (19) | 0.0032 (19) | −0.019 (2) |
N10 | 0.105 (12) | 0.112 (12) | 0.105 (12) | −0.017 (9) | 0.001 (9) | −0.032 (9) |
N10' | 0.083 (7) | 0.116 (11) | 0.095 (9) | −0.039 (7) | 0.000 (7) | −0.048 (7) |
O1 | 0.0329 (17) | 0.062 (2) | 0.080 (2) | −0.0014 (15) | 0.0019 (15) | 0.0115 (15) |
O2 | 0.133 (4) | 0.062 (3) | 0.221 (5) | −0.007 (3) | −0.013 (4) | −0.019 (3) |
O3 | 0.213 (5) | 0.066 (3) | 0.137 (4) | 0.069 (3) | 0.002 (3) | 0.007 (2) |
O4 | 0.0309 (17) | 0.060 (2) | 0.094 (2) | −0.0044 (15) | −0.0003 (16) | −0.0134 (16) |
O5 | 0.100 (9) | 0.111 (9) | 0.081 (8) | −0.026 (7) | 0.011 (7) | −0.023 (7) |
O6 | 0.124 (9) | 0.142 (10) | 0.119 (9) | −0.041 (8) | −0.006 (7) | −0.048 (7) |
O5' | 0.121 (6) | 0.177 (8) | 0.111 (6) | −0.032 (6) | 0.028 (5) | −0.068 (6) |
O6' | 0.152 (6) | 0.122 (7) | 0.137 (6) | −0.020 (5) | −0.022 (5) | −0.061 (5) |
O7 | 0.056 (2) | 0.070 (2) | 0.116 (3) | −0.0024 (19) | 0.009 (2) | −0.014 (2) |
O8 | 0.067 (2) | 0.105 (3) | 0.151 (4) | −0.005 (2) | 0.003 (2) | −0.043 (3) |
C1 | 0.033 (3) | 0.053 (3) | 0.048 (3) | −0.006 (3) | 0.005 (2) | −0.006 (2) |
C2 | 0.039 (3) | 0.040 (3) | 0.050 (3) | 0.004 (2) | 0.003 (2) | 0.003 (2) |
C3 | 0.041 (3) | 0.038 (3) | 0.043 (3) | 0.001 (2) | 0.002 (2) | −0.006 (2) |
C4 | 0.030 (2) | 0.040 (3) | 0.050 (3) | 0.001 (2) | −0.001 (2) | −0.004 (2) |
C5 | 0.032 (3) | 0.044 (3) | 0.047 (3) | −0.007 (2) | 0.004 (2) | −0.005 (2) |
C6 | 0.041 (3) | 0.051 (4) | 0.080 (4) | 0.004 (2) | 0.011 (3) | 0.006 (3) |
C7 | 0.042 (3) | 0.041 (3) | 0.055 (3) | 0.004 (2) | 0.002 (2) | 0.000 (2) |
C8 | 0.043 (3) | 0.043 (3) | 0.054 (3) | 0.002 (2) | 0.004 (2) | 0.001 (2) |
C9 | 0.045 (3) | 0.049 (3) | 0.069 (3) | 0.007 (3) | 0.006 (2) | 0.003 (3) |
C10 | 0.064 (4) | 0.051 (4) | 0.076 (4) | 0.011 (3) | 0.012 (3) | 0.007 (3) |
C11 | 0.074 (4) | 0.075 (5) | 0.094 (4) | 0.028 (4) | 0.018 (3) | 0.034 (3) |
C12 | 0.061 (3) | 0.088 (5) | 0.088 (4) | 0.009 (4) | −0.017 (3) | 0.026 (4) |
C13 | 0.056 (3) | 0.067 (4) | 0.064 (3) | 0.001 (3) | −0.004 (3) | 0.002 (3) |
C14 | 0.034 (3) | 0.053 (3) | 0.049 (3) | 0.001 (2) | 0.004 (2) | −0.008 (2) |
C15 | 0.034 (3) | 0.047 (3) | 0.053 (3) | 0.000 (2) | 0.003 (2) | −0.010 (2) |
C16 | 0.034 (3) | 0.047 (3) | 0.046 (3) | −0.005 (2) | 0.001 (2) | −0.006 (2) |
C17 | 0.027 (2) | 0.052 (3) | 0.050 (3) | −0.004 (2) | 0.002 (2) | −0.008 (2) |
C18 | 0.029 (3) | 0.049 (3) | 0.056 (3) | 0.002 (2) | 0.003 (2) | −0.006 (2) |
C19 | 0.038 (3) | 0.063 (4) | 0.063 (3) | −0.010 (3) | 0.006 (2) | −0.006 (3) |
C20 | 0.047 (3) | 0.043 (3) | 0.062 (3) | −0.003 (3) | 0.005 (3) | −0.012 (2) |
C21 | 0.036 (3) | 0.049 (3) | 0.053 (3) | −0.002 (2) | 0.004 (2) | −0.010 (3) |
C22 | 0.041 (3) | 0.080 (4) | 0.071 (4) | −0.018 (3) | 0.006 (2) | −0.023 (3) |
C23 | 0.051 (3) | 0.089 (4) | 0.087 (4) | −0.010 (3) | 0.008 (3) | −0.050 (4) |
C24 | 0.053 (4) | 0.068 (4) | 0.142 (6) | −0.016 (3) | 0.014 (4) | −0.037 (4) |
C25 | 0.057 (3) | 0.067 (4) | 0.122 (5) | −0.015 (3) | 0.016 (3) | −0.004 (4) |
C26 | 0.049 (3) | 0.070 (4) | 0.067 (3) | −0.009 (3) | 0.016 (3) | −0.007 (3) |
C27 | 0.100 (5) | 0.090 (5) | 0.102 (5) | 0.010 (4) | −0.007 (4) | 0.009 (3) |
C28 | 0.079 (4) | 0.175 (7) | 0.166 (6) | 0.048 (4) | 0.017 (4) | 0.008 (5) |
C29 | 0.155 (7) | 0.210 (10) | 0.177 (8) | 0.007 (7) | 0.016 (6) | −0.073 (7) |
C30 | 0.175 (7) | 0.281 (8) | 0.175 (7) | −0.054 (6) | 0.038 (5) | −0.045 (6) |
N1—C5 | 1.355 (4) | C8—C13 | 1.392 (5) |
N1—C1 | 1.380 (4) | C9—C10 | 1.370 (5) |
N1—H1 | 0.8600 | C9—H9 | 0.9300 |
N2—C6 | 1.132 (5) | C10—C11 | 1.352 (6) |
N3—C7 | 1.139 (4) | C11—C12 | 1.373 (6) |
N4—C5 | 1.320 (4) | C11—H11 | 0.9300 |
N4—H4A | 0.8600 | C12—C13 | 1.382 (6) |
N4—H4B | 0.8600 | C12—H12 | 0.9300 |
N5—O3 | 1.205 (5) | C13—H13 | 0.9300 |
N5—O2 | 1.210 (5) | C14—C15 | 1.421 (5) |
N5—C10 | 1.466 (6) | C15—C16 | 1.380 (5) |
N6—C18 | 1.354 (4) | C15—C19 | 1.426 (5) |
N6—C14 | 1.380 (4) | C16—C17 | 1.379 (5) |
N6—H6 | 0.8600 | C16—C21 | 1.485 (5) |
N7—C19 | 1.145 (5) | C17—C18 | 1.409 (5) |
N8—C20 | 1.151 (4) | C17—C20 | 1.427 (5) |
N9—C18 | 1.316 (4) | C21—C26 | 1.374 (5) |
N9—H9A | 0.8600 | C21—C22 | 1.386 (5) |
N9—H9B | 0.8600 | C22—C23 | 1.373 (5) |
N10—O5 | 1.13 (4) | C22—H22 | 0.9300 |
N10—O6 | 1.32 (4) | C23—C24 | 1.357 (6) |
N10—C23 | 1.70 (4) | C24—C25 | 1.373 (6) |
N10'—O5' | 1.183 (13) | C24—H24 | 0.9300 |
N10'—O6' | 1.186 (11) | C25—C26 | 1.386 (5) |
N10'—C23 | 1.433 (13) | C25—H25 | 0.9300 |
O1—C1 | 1.242 (4) | C26—H26 | 0.9300 |
O4—C14 | 1.245 (4) | C27—C28 | 1.460 (6) |
O7—C27 | 1.410 (5) | C27—H27A | 0.9700 |
O7—H7 | 0.8200 | C27—H27B | 0.9700 |
O8—C29 | 1.427 (7) | C28—H28A | 0.9600 |
O8—H8 | 0.8200 | C28—H28B | 0.9600 |
C1—C2 | 1.433 (5) | C28—H28C | 0.9600 |
C2—C3 | 1.374 (5) | C29—C30 | 1.523 (8) |
C2—C6 | 1.420 (5) | C29—H29A | 0.9700 |
C3—C4 | 1.396 (5) | C29—H29B | 0.9700 |
C3—C8 | 1.480 (5) | C30—H30A | 0.9600 |
C4—C5 | 1.406 (5) | C30—H30B | 0.9600 |
C4—C7 | 1.425 (5) | C30—H30C | 0.9600 |
C8—C9 | 1.370 (5) | ||
C5—N1—C1 | 124.4 (4) | N6—C14—C15 | 115.3 (4) |
C5—N1—H1 | 117.8 | C16—C15—C14 | 121.6 (4) |
C1—N1—H1 | 117.8 | C16—C15—C19 | 121.3 (4) |
C5—N4—H4A | 120.0 | C14—C15—C19 | 117.1 (4) |
C5—N4—H4B | 120.0 | C17—C16—C15 | 119.7 (4) |
H4A—N4—H4B | 120.0 | C17—C16—C21 | 118.9 (4) |
O3—N5—O2 | 123.7 (6) | C15—C16—C21 | 121.4 (4) |
O3—N5—C10 | 118.4 (6) | C16—C17—C18 | 120.5 (4) |
O2—N5—C10 | 117.8 (6) | C16—C17—C20 | 121.6 (4) |
C18—N6—C14 | 125.3 (4) | C18—C17—C20 | 117.7 (4) |
C18—N6—H6 | 117.3 | N9—C18—N6 | 118.7 (4) |
C14—N6—H6 | 117.3 | N9—C18—C17 | 123.7 (4) |
C18—N9—H9A | 120.0 | N6—C18—C17 | 117.5 (4) |
C18—N9—H9B | 120.0 | N7—C19—C15 | 179.7 (6) |
H9A—N9—H9B | 120.0 | N8—C20—C17 | 177.8 (5) |
O5—N10—O6 | 127 (3) | C26—C21—C22 | 118.8 (4) |
O5—N10—C23 | 128 (3) | C26—C21—C16 | 120.8 (4) |
O6—N10—C23 | 106 (3) | C22—C21—C16 | 120.3 (4) |
O5'—N10'—O6' | 121.0 (13) | C23—C22—C21 | 117.6 (4) |
O5'—N10'—C23 | 117.8 (11) | C23—C22—H22 | 121.2 |
O6'—N10'—C23 | 121.1 (12) | C21—C22—H22 | 121.2 |
C27—O7—H7 | 109.5 | C24—C23—C22 | 123.9 (5) |
C29—O8—H8 | 109.5 | C24—C23—N10' | 114.5 (8) |
O1—C1—N1 | 119.1 (4) | C22—C23—N10' | 121.0 (7) |
O1—C1—C2 | 124.3 (4) | C24—C23—N10 | 128.3 (15) |
N1—C1—C2 | 116.6 (4) | C22—C23—N10 | 105.7 (14) |
C3—C2—C6 | 122.4 (4) | C23—C24—C25 | 118.8 (5) |
C3—C2—C1 | 120.3 (4) | C23—C24—H24 | 120.6 |
C6—C2—C1 | 117.3 (4) | C25—C24—H24 | 120.6 |
C2—C3—C4 | 120.3 (4) | C24—C25—C26 | 118.4 (5) |
C2—C3—C8 | 120.8 (4) | C24—C25—H25 | 120.8 |
C4—C3—C8 | 118.9 (4) | C26—C25—H25 | 120.8 |
C3—C4—C5 | 120.1 (4) | C21—C26—C25 | 122.4 (5) |
C3—C4—C7 | 122.9 (4) | C21—C26—H26 | 118.8 |
C5—C4—C7 | 117.0 (4) | C25—C26—H26 | 118.8 |
N4—C5—N1 | 117.3 (4) | O7—C27—C28 | 111.0 (5) |
N4—C5—C4 | 124.5 (4) | O7—C27—H27A | 109.4 |
N1—C5—C4 | 118.2 (4) | C28—C27—H27A | 109.4 |
N2—C6—C2 | 179.0 (6) | O7—C27—H27B | 109.4 |
N3—C7—C4 | 179.3 (5) | C28—C27—H27B | 109.4 |
C9—C8—C13 | 118.5 (4) | H27A—C27—H27B | 108.0 |
C9—C8—C3 | 119.5 (4) | C27—C28—H28A | 109.5 |
C13—C8—C3 | 122.0 (4) | C27—C28—H28B | 109.5 |
C10—C9—C8 | 119.5 (4) | H28A—C28—H28B | 109.5 |
C10—C9—H9 | 120.2 | C27—C28—H28C | 109.5 |
C8—C9—H9 | 120.2 | H28A—C28—H28C | 109.5 |
C11—C10—C9 | 122.8 (5) | H28B—C28—H28C | 109.5 |
C11—C10—N5 | 118.5 (5) | O8—C29—C30 | 102.3 (6) |
C9—C10—N5 | 118.7 (5) | O8—C29—H29A | 111.3 |
C10—C11—C12 | 118.5 (5) | C30—C29—H29A | 111.3 |
C10—C11—H11 | 120.7 | O8—C29—H29B | 111.3 |
C12—C11—H11 | 120.7 | C30—C29—H29B | 111.3 |
C11—C12—C13 | 120.0 (5) | H29A—C29—H29B | 109.2 |
C11—C12—H12 | 120.0 | C29—C30—H30A | 109.5 |
C13—C12—H12 | 120.0 | C29—C30—H30B | 109.5 |
C12—C13—C8 | 120.7 (5) | H30A—C30—H30B | 109.5 |
C12—C13—H13 | 119.7 | C29—C30—H30C | 109.5 |
C8—C13—H13 | 119.7 | H30A—C30—H30C | 109.5 |
O4—C14—N6 | 118.8 (4) | H30B—C30—H30C | 109.5 |
O4—C14—C15 | 125.9 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N9—H9A···O8 | 0.86 | 1.94 | 2.785 (5) | 167 |
C22—H22···O5 | 0.93 | 2.42 | 2.802 (19) | 104 |
N1—H1···O4i | 0.86 | 1.98 | 2.826 (4) | 170 |
N4—H4A···O7ii | 0.86 | 1.97 | 2.816 (4) | 169 |
N4—H4B···N8ii | 0.86 | 2.17 | 3.009 (5) | 164 |
C13—H13···O3ii | 0.93 | 2.32 | 3.228 (6) | 167 |
C25—H25···O3ii | 0.93 | 2.59 | 3.464 (7) | 158 |
N6—H6···O1iii | 0.86 | 1.98 | 2.830 (4) | 171 |
O8—H8···O1iii | 0.82 | 2.19 | 2.824 (4) | 135 |
N9—H9B···N3iv | 0.86 | 2.22 | 3.047 (5) | 163 |
O7—H7···O4v | 0.82 | 2.01 | 2.753 (4) | 150 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+1/2, y−1/2, −z+3/2; (iii) −x+3/2, y+1/2, −z+3/2; (iv) −x+1/2, y+1/2, −z+3/2; (v) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C13H7N5O3·C2H6O |
Mr | 327.30 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 13.079 (3), 14.764 (4), 16.693 (4) |
β (°) | 90.923 (4) |
V (Å3) | 3223.0 (14) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.45 × 0.36 × 0.31 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.950, 0.962 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16780, 5690, 1952 |
Rint | 0.089 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.124, 1.01 |
No. of reflections | 5690 |
No. of parameters | 465 |
No. of restraints | 160 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.38, −0.33 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N9—H9A···O8 | 0.86 | 1.94 | 2.785 (5) | 166.7 |
C22—H22···O5 | 0.93 | 2.42 | 2.802 (19) | 104.2 |
N1—H1···O4i | 0.86 | 1.98 | 2.826 (4) | 169.6 |
N4—H4A···O7ii | 0.86 | 1.97 | 2.816 (4) | 169.0 |
N4—H4B···N8ii | 0.86 | 2.17 | 3.009 (5) | 164.2 |
C13—H13···O3ii | 0.93 | 2.32 | 3.228 (6) | 167.3 |
C25—H25···O3ii | 0.93 | 2.59 | 3.464 (7) | 157.5 |
N6—H6···O1iii | 0.86 | 1.98 | 2.830 (4) | 171.0 |
O8—H8···O1iii | 0.82 | 2.19 | 2.824 (4) | 134.8 |
N9—H9B···N3iv | 0.86 | 2.22 | 3.047 (5) | 162.7 |
O7—H7···O4v | 0.82 | 2.01 | 2.753 (4) | 149.6 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+1/2, y−1/2, −z+3/2; (iii) −x+3/2, y+1/2, −z+3/2; (iv) −x+1/2, y+1/2, −z+3/2; (v) x−1, y, z. |
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The synthesis of 2-pyridone derivatives is an area of growing interest because compounds with these scaffolds exhibited significant pharmacological properties such as antibacterial (Li et al., 2000), antifungal (Cox & O'Hagan, 1991) and antitumor activity (Nagarajan et al., 2003). These compounds have been used also as cardiotonic (Deshang et al., 1988) and psychotherapeutic agents (Kozikowski et al., 1996) and potential HIC-1 specific transcriptase inhibitors (Boeckman et al., 1987). Moreover it is well know that the 2-pyridone ring system is a valuable building block in the symthesis of natural products (Comins et al., 1994). For these reasons, the synthesis of new compounds containing 2-pyridone derivatives is strongly desired. In this paper we report the crystal structure of the title compound.
In the asymmetric units there are two title molecules of similar geometry and two ethanol molecules (Fig. 1). One nitro group is disordered over two positions, with refined site occupation factors of 0.688 (17) and 0.312 (17) for the major and minor components, respectively. The dihedral angle between the C1/C2/C3/C4/C5/N1 plane and the C8—C13 benzene ring is 52.06 (11) °, while the corresponding angle between the C14/C15/C16/C17/C18/N6 plane and the C21—C26 benzene ring is 65.12 (13)°. The crystal packing is stabilized by an extended network of N—H···O, N—H···N, O—H···O and C—H···O intra- and intermolecular hydrogen bonds (Table 1, Fig. 2).