Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536814013713/mw2124sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536814013713/mw2124Isup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536814013713/mw2124Isup3.cml |
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.036
- wR factor = 0.104
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 3 Why ? PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 2 Note H2 O PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) ..... 3 Why ?
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 0 ALERT level C = Check. Ensure it is not caused by an omission or oversight 4 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
4-Methoxybenzoylhydrazide (1.00 mmol), 6-methyl-3-formylchromone (1.00 mmol), and a few drops of acetic acid were dissolved in 25 mL of benzene and the mixture was refluxed with a Dean-Stark apparatus for 6 h. After cooling, the precipitates were collected, washed with n-hexane, and dried (yield 68.9%). 1H NMR (400 MHz, DMSO-d6): δ = 2.45 (s, 3H), 3.84 (s, 3H), 7.06 (d, 1H, J = 8.8 Hz), 7.63 (d, 1H, J = 8.3 Hz), 7.69 (dd, 1H, J = 2.5 and 8.3 Hz), 7.93 (d, 1H, J = 8.8 Hz), 7.94 (d, 1H, J = 2.5 Hz), 8.63 (s, 1H), 8.79 (s, 1H), 11.82 (s, 1H). DART-MS calcd for [C19H16N2O4 + H+]: 337.119, found 337.194. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an N,N-dimethylformamide solution of the title compound at room temperature.
The C(sp2)- and N(sp2)-bound hydrogen atoms were placed in geometrical positions [C–H 0.95 Å, Uiso(H) = 1.2Ueq(C), N–H 0.88 Å, Uiso(H) = 1.2Ueq(N)], and refined using a riding model. Hydrogen atoms of methyl groups were found in a difference Fourier map, and a rotating group model was applied with distance constraint [C–H = 0.98 Å, Uiso(H) = 1.2Ueq(C)]. Hydrogen atoms of the water molecule were found in a difference Fourier map, and were refined using a riding model.
Schiff base derivatives of 3-formyl chromones have attracted much attention due to their biological functions such as enzyme inhibition (Khan et al. 2009; Tu et al. 2013). We herein report the crystal structure of the title compound, which was obtained from the condensation reaction of 6-methyl-3-formylchromone with 4-methoxybenzoylhydrazide in benzene.
The 4H-chromen-4-one segment segment is slightly twisted with a dihedral angle between the two 6-membered rings of 3.30 (5)°. The dihedral angles between the pyranone ring and the hydrazide plane (C11/N1/N2/C12) and between the pyranone ring and the benzene ring of the p-methoxybenzene unit are 26.69 (4) and 2.23 (3)°, respectively. The molecule is connected to the solvent water molecule byan N–H···O hydrogen bond.
In the crystal, there are π-π stacking interactions between centrosymmetrically-related pyranone rings [centroid–centroidi distance = 3.5394 (9) Å, i: –x + 1, –y + 1, –z + 1] as well as bridges formed by the water molecules via O–H···O hydrogen bonds (Fig. 2).
For the biological activity of related compounds, see: Khan et al. (2009); Tu et al. (2013). For related structures, see: Ishikawa & Watanabe (2014a,b).
Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software(Rigaku, 1999); data reduction: WinAFC Diffractometer Control Software (Rigaku, 1999); program(s) used to solve structure: SIR2008 (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).
C19H16N2O4·H2O | Z = 2 |
Mr = 354.36 | F(000) = 372.00 |
Triclinic, P1 | Dx = 1.437 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 7.6228 (13) Å | Cell parameters from 25 reflections |
b = 10.809 (3) Å | θ = 15.0–17.3° |
c = 11.260 (2) Å | µ = 0.11 mm−1 |
α = 116.339 (14)° | T = 100 K |
β = 94.258 (14)° | Block, colorless |
γ = 96.190 (16)° | 0.48 × 0.35 × 0.13 mm |
V = 818.8 (3) Å3 |
Rigaku AFC-7R diffractometer | θmax = 27.5° |
ω–2θ scans | h = −9→5 |
4581 measured reflections | k = −13→14 |
3748 independent reflections | l = −14→14 |
3219 reflections with F2 > 2σ(F2) | 3 standard reflections every 150 reflections |
Rint = 0.008 | intensity decay: −0.9% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0564P)2 + 0.2692P] where P = (Fo2 + 2Fc2)/3 |
3748 reflections | (Δ/σ)max < 0.001 |
245 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Primary atom site location: structure-invariant direct methods |
C19H16N2O4·H2O | γ = 96.190 (16)° |
Mr = 354.36 | V = 818.8 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.6228 (13) Å | Mo Kα radiation |
b = 10.809 (3) Å | µ = 0.11 mm−1 |
c = 11.260 (2) Å | T = 100 K |
α = 116.339 (14)° | 0.48 × 0.35 × 0.13 mm |
β = 94.258 (14)° |
Rigaku AFC-7R diffractometer | Rint = 0.008 |
4581 measured reflections | 3 standard reflections every 150 reflections |
3748 independent reflections | intensity decay: −0.9% |
3219 reflections with F2 > 2σ(F2) |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.28 e Å−3 |
3748 reflections | Δρmin = −0.27 e Å−3 |
245 parameters |
Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.20207 (10) | 0.53571 (9) | 0.53711 (8) | 0.01721 (18) | |
O2 | 0.55749 (11) | 0.68656 (9) | 0.35944 (8) | 0.01894 (19) | |
O3 | −0.21138 (10) | 0.30160 (9) | −0.02159 (8) | 0.02063 (19) | |
O4 | −0.10198 (11) | 0.11287 (9) | −0.63143 (8) | 0.02078 (19) | |
O5 | 0.43347 (11) | 0.31344 (10) | −0.10886 (9) | 0.0217 (2) | |
N1 | 0.11013 (12) | 0.40533 (10) | 0.13232 (9) | 0.0151 (2) | |
N2 | 0.09049 (12) | 0.34737 (10) | −0.00533 (9) | 0.0148 (2) | |
C1 | 0.18957 (14) | 0.48425 (12) | 0.40352 (11) | 0.0155 (3) | |
C2 | 0.30132 (14) | 0.52846 (11) | 0.33784 (10) | 0.0138 (3) | |
C3 | 0.45241 (14) | 0.63884 (11) | 0.41270 (10) | 0.0134 (2) | |
C4 | 0.61596 (14) | 0.78940 (11) | 0.64525 (11) | 0.0148 (3) | |
C5 | 0.63334 (15) | 0.83414 (11) | 0.78214 (11) | 0.0162 (3) | |
C6 | 0.49795 (16) | 0.78222 (12) | 0.83435 (11) | 0.0179 (3) | |
C7 | 0.35334 (15) | 0.68501 (12) | 0.75278 (11) | 0.0177 (3) | |
C8 | 0.47079 (14) | 0.68973 (11) | 0.55867 (10) | 0.0134 (3) | |
C9 | 0.34401 (14) | 0.63802 (11) | 0.61494 (11) | 0.0147 (3) | |
C10 | 0.79455 (17) | 0.93337 (13) | 0.87393 (11) | 0.0223 (3) | |
C11 | 0.26801 (14) | 0.46611 (11) | 0.19139 (11) | 0.0141 (2) | |
C12 | −0.07629 (14) | 0.30143 (11) | −0.07521 (11) | 0.0145 (3) | |
C13 | −0.08209 (14) | 0.25000 (11) | −0.22219 (11) | 0.0139 (2) | |
C14 | −0.21783 (15) | 0.14353 (12) | −0.30858 (11) | 0.0165 (3) | |
C15 | −0.22855 (15) | 0.09151 (12) | −0.44696 (11) | 0.0174 (3) | |
C16 | −0.10404 (15) | 0.15125 (11) | −0.49879 (11) | 0.0154 (3) | |
C17 | 0.03025 (15) | 0.26040 (12) | −0.41282 (11) | 0.0159 (3) | |
C18 | 0.04234 (14) | 0.30807 (11) | −0.27641 (11) | 0.0145 (3) | |
C19 | −0.23205 (17) | −0.00285 (13) | −0.72346 (11) | 0.0229 (3) | |
H1 | 0.0943 | 0.4108 | 0.3511 | 0.0186* | |
H2 | 0.7036 | 0.8267 | 0.6091 | 0.0177* | |
H3 | 0.5064 | 0.8150 | 0.9284 | 0.0214* | |
H4 | 0.2628 | 0.6511 | 0.7894 | 0.0212* | |
H5 | 0.3614 | 0.4707 | 0.1414 | 0.0169* | |
H6 | 0.1845 | 0.3402 | −0.0474 | 0.0177* | |
H7 | −0.3048 | 0.1056 | −0.2725 | 0.0198* | |
H8 | −0.3192 | 0.0166 | −0.5050 | 0.0208* | |
H9 | 0.1135 | 0.3019 | −0.4486 | 0.0191* | |
H10 | 0.1356 | 0.3807 | −0.2188 | 0.0174* | |
H11A | 0.8763 | 0.9571 | 0.8213 | 0.0268* | |
H12B | 0.8551 | 0.8888 | 0.9208 | 0.0268* | |
H13C | 0.7571 | 1.0187 | 0.9394 | 0.0268* | |
H14A | −0.2229 | −0.0838 | −0.7069 | 0.0274* | |
H15B | −0.2108 | −0.0262 | −0.8153 | 0.0274* | |
H16C | −0.3515 | 0.0223 | −0.7112 | 0.0274* | |
H17 | 0.5408 | 0.3116 | −0.0806 | 0.0412* | |
H18 | 0.4419 | 0.3158 | −0.1845 | 0.0441* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0149 (4) | 0.0220 (4) | 0.0133 (4) | −0.0023 (3) | 0.0011 (3) | 0.0079 (4) |
O2 | 0.0155 (4) | 0.0265 (5) | 0.0147 (4) | −0.0021 (4) | 0.0015 (3) | 0.0105 (4) |
O3 | 0.0131 (4) | 0.0313 (5) | 0.0159 (4) | 0.0008 (4) | 0.0022 (3) | 0.0099 (4) |
O4 | 0.0224 (5) | 0.0252 (5) | 0.0114 (4) | 0.0014 (4) | 0.0011 (3) | 0.0060 (4) |
O5 | 0.0146 (4) | 0.0348 (5) | 0.0165 (4) | 0.0022 (4) | 0.0025 (4) | 0.0129 (4) |
N1 | 0.0165 (5) | 0.0164 (5) | 0.0110 (5) | 0.0030 (4) | 0.0009 (4) | 0.0050 (4) |
N2 | 0.0125 (5) | 0.0191 (5) | 0.0101 (5) | 0.0012 (4) | 0.0011 (4) | 0.0047 (4) |
C1 | 0.0135 (5) | 0.0181 (5) | 0.0128 (5) | 0.0012 (4) | 0.0000 (4) | 0.0058 (4) |
C2 | 0.0123 (5) | 0.0153 (5) | 0.0126 (5) | 0.0031 (4) | 0.0002 (4) | 0.0055 (4) |
C3 | 0.0109 (5) | 0.0164 (5) | 0.0131 (5) | 0.0036 (4) | 0.0013 (4) | 0.0067 (4) |
C4 | 0.0149 (5) | 0.0153 (5) | 0.0139 (5) | 0.0018 (4) | 0.0021 (4) | 0.0065 (4) |
C5 | 0.0177 (6) | 0.0149 (5) | 0.0139 (5) | 0.0028 (4) | −0.0002 (4) | 0.0050 (4) |
C6 | 0.0228 (6) | 0.0192 (6) | 0.0109 (5) | 0.0047 (5) | 0.0023 (4) | 0.0060 (5) |
C7 | 0.0185 (6) | 0.0218 (6) | 0.0149 (6) | 0.0039 (5) | 0.0049 (4) | 0.0098 (5) |
C8 | 0.0135 (5) | 0.0148 (5) | 0.0122 (5) | 0.0037 (4) | 0.0015 (4) | 0.0062 (4) |
C9 | 0.0128 (5) | 0.0168 (5) | 0.0140 (5) | 0.0025 (4) | 0.0010 (4) | 0.0067 (5) |
C10 | 0.0246 (6) | 0.0227 (6) | 0.0143 (6) | −0.0033 (5) | −0.0031 (5) | 0.0061 (5) |
C11 | 0.0134 (5) | 0.0149 (5) | 0.0134 (5) | 0.0022 (4) | 0.0015 (4) | 0.0059 (4) |
C12 | 0.0138 (5) | 0.0140 (5) | 0.0149 (5) | 0.0011 (4) | 0.0009 (4) | 0.0063 (4) |
C13 | 0.0129 (5) | 0.0150 (5) | 0.0133 (5) | 0.0033 (4) | 0.0012 (4) | 0.0059 (4) |
C14 | 0.0146 (5) | 0.0181 (6) | 0.0164 (6) | 0.0001 (4) | 0.0015 (4) | 0.0082 (5) |
C15 | 0.0158 (5) | 0.0164 (6) | 0.0162 (6) | 0.0001 (4) | −0.0014 (4) | 0.0051 (5) |
C16 | 0.0171 (6) | 0.0168 (5) | 0.0118 (5) | 0.0061 (4) | 0.0012 (4) | 0.0055 (4) |
C17 | 0.0145 (5) | 0.0177 (5) | 0.0176 (6) | 0.0031 (4) | 0.0034 (4) | 0.0095 (5) |
C18 | 0.0127 (5) | 0.0144 (5) | 0.0151 (5) | 0.0011 (4) | 0.0000 (4) | 0.0062 (4) |
C19 | 0.0230 (6) | 0.0251 (6) | 0.0124 (5) | 0.0035 (5) | −0.0021 (5) | 0.0022 (5) |
O1—C1 | 1.3438 (15) | C14—C15 | 1.3944 (17) |
O1—C9 | 1.3794 (12) | C15—C16 | 1.3939 (19) |
O2—C3 | 1.2345 (17) | C16—C17 | 1.3985 (14) |
O3—C12 | 1.2315 (15) | C17—C18 | 1.3782 (17) |
O4—C16 | 1.3631 (16) | O5—H17 | 0.861 |
O4—C19 | 1.4322 (14) | O5—H18 | 0.871 |
N1—N2 | 1.3787 (14) | N2—H6 | 0.880 |
N1—C11 | 1.2827 (13) | C1—H1 | 0.950 |
N2—C12 | 1.3604 (14) | C4—H2 | 0.950 |
C1—C2 | 1.3492 (19) | C6—H3 | 0.950 |
C2—C3 | 1.4586 (14) | C7—H4 | 0.950 |
C2—C11 | 1.4672 (16) | C10—H11A | 0.980 |
C3—C8 | 1.4732 (16) | C10—H12B | 0.980 |
C4—C5 | 1.3862 (17) | C10—H13C | 0.980 |
C4—C8 | 1.4094 (14) | C11—H5 | 0.950 |
C5—C6 | 1.4084 (19) | C14—H7 | 0.950 |
C5—C10 | 1.5074 (15) | C15—H8 | 0.950 |
C6—C7 | 1.3807 (15) | C17—H9 | 0.950 |
C7—C9 | 1.3958 (17) | C18—H10 | 0.950 |
C8—C9 | 1.3916 (18) | C19—H14A | 0.980 |
C12—C13 | 1.4891 (17) | C19—H15B | 0.980 |
C13—C14 | 1.3934 (14) | C19—H16C | 0.980 |
C13—C18 | 1.4014 (19) | ||
O1···C3 | 2.8584 (17) | C11···H18iv | 3.0847 |
O2···C1 | 3.5695 (17) | C12···H4i | 3.4658 |
O2···C4 | 2.8803 (16) | C12···H11Axi | 3.3379 |
O2···C11 | 2.8936 (14) | C12···H13Cxi | 3.2583 |
O3···N1 | 2.7054 (13) | C12···H17vi | 2.9300 |
O3···C14 | 2.9022 (15) | C13···H11Axi | 3.3981 |
O3···C18 | 3.5987 (17) | C13···H14Aviii | 3.0288 |
N1···C1 | 2.7788 (17) | C13···H15Bviii | 3.5976 |
N2···C18 | 2.8777 (18) | C13···H17vi | 3.3762 |
C1···C7 | 3.5842 (17) | C14···H2xi | 3.0995 |
C1···C8 | 2.7485 (15) | C14···H11Axi | 3.0798 |
C2···C9 | 2.7804 (17) | C14···H14Aviii | 3.4949 |
C4···C7 | 2.7985 (19) | C14···H17vi | 3.2493 |
C5···C9 | 2.7814 (15) | C14···H18vi | 3.3794 |
C6···C8 | 2.7899 (17) | C15···H2xi | 3.1928 |
C11···C12 | 3.4855 (17) | C15···H8xv | 3.4404 |
C13···C16 | 2.7930 (18) | C16···H2iv | 3.4036 |
C14···C17 | 2.771 (2) | C17···H1v | 3.5568 |
C15···C18 | 2.7948 (16) | C17···H2iv | 3.0193 |
C15···C19 | 2.8103 (18) | C17···H14Aviii | 3.1958 |
O1···O1i | 3.0524 (12) | C18···H14Aviii | 2.8568 |
O1···C1i | 3.1131 (15) | C18···H18 | 3.1229 |
O1···C3ii | 3.5514 (17) | C19···H6viii | 3.4870 |
O1···C8ii | 3.5633 (16) | C19···H7xv | 3.5754 |
O1···C17iii | 3.413 (2) | C19···H11Aiv | 3.0741 |
O2···O5iv | 2.8274 (16) | C19···H17viii | 3.5419 |
O2···C14v | 3.4847 (18) | C19···H18viii | 3.2485 |
O2···C15v | 3.5467 (17) | H1···O1i | 2.6612 |
O2···C17iv | 3.0969 (15) | H1···O4iii | 3.4948 |
O2···C18iv | 3.2582 (16) | H1···C1i | 3.4987 |
O3···O5vi | 2.8465 (13) | H1···C4ii | 3.2645 |
O3···C6i | 3.4626 (18) | H1···C5ii | 3.4193 |
O3···C7i | 3.2379 (18) | H1···C7i | 3.4139 |
O4···C9v | 3.3715 (18) | H1···C9i | 3.4026 |
O5···O2iv | 2.8274 (16) | H1···C17v | 3.5568 |
O5···O3vii | 2.8465 (13) | H1···H1i | 3.5510 |
O5···N2 | 2.9341 (14) | H1···H2ii | 3.3061 |
O5···C11 | 3.4460 (16) | H1···H4i | 2.8965 |
O5···C11iv | 3.5818 (19) | H1···H9iii | 2.9731 |
O5···C18 | 3.3885 (16) | H1···H9v | 3.4140 |
O5···C19viii | 3.1664 (17) | H1···H12Bii | 3.4139 |
N1···C12v | 3.534 (2) | H2···O4iv | 3.0040 |
N1···C13v | 3.4362 (19) | H2···C1ii | 3.4871 |
N1···C18v | 3.1900 (17) | H2···C14x | 3.0995 |
N2···O5 | 2.9341 (14) | H2···C15x | 3.1928 |
N2···C12v | 3.5061 (19) | H2···C16iv | 3.4036 |
C1···O1i | 3.1131 (15) | H2···C17iv | 3.0193 |
C1···C4ii | 3.297 (2) | H2···H1ii | 3.3061 |
C1···C8ii | 3.4666 (19) | H2···H7x | 2.7132 |
C1···C17v | 3.347 (2) | H2···H8x | 2.8772 |
C2···C7ii | 3.5937 (19) | H2···H9iv | 2.3881 |
C2···C8ii | 3.600 (2) | H2···H16Cv | 3.3063 |
C2···C9ii | 3.5376 (19) | H3···O3i | 2.9428 |
C2···C17v | 3.4872 (19) | H3···O5ii | 2.9615 |
C2···C18v | 3.5038 (19) | H3···C11ii | 3.4417 |
C3···O1ii | 3.5514 (17) | H3···H5ii | 3.1313 |
C3···C9ii | 3.422 (2) | H3···H6ii | 3.5413 |
C3···C15v | 3.425 (2) | H3···H13Cxii | 2.8860 |
C3···C16v | 3.5874 (18) | H3···H15Bxiv | 3.1317 |
C4···C1ii | 3.297 (2) | H3···H17ii | 2.6475 |
C5···C11ii | 3.541 (2) | H4···O3i | 2.5018 |
C6···O3i | 3.4626 (18) | H4···N1i | 3.1154 |
C6···C11ii | 3.300 (2) | H4···C12i | 3.4658 |
C7···O3i | 3.2379 (18) | H4···H1i | 2.8965 |
C7···C2ii | 3.5937 (19) | H4···H5ii | 3.4550 |
C8···O1ii | 3.5633 (16) | H4···H9iii | 3.5172 |
C8···C1ii | 3.4666 (19) | H4···H10iii | 2.9367 |
C8···C2ii | 3.600 (2) | H4···H13Cxii | 3.5497 |
C9···O4v | 3.3715 (18) | H4···H17ii | 3.3353 |
C9···C2ii | 3.5376 (19) | H5···O3v | 3.5370 |
C9···C3ii | 3.422 (2) | H5···O5 | 2.7040 |
C11···O5 | 3.4460 (16) | H5···O5iv | 2.8429 |
C11···O5iv | 3.5818 (19) | H5···C6ii | 3.1539 |
C11···C5ii | 3.541 (2) | H5···C7ii | 3.3413 |
C11···C6ii | 3.300 (2) | H5···H3ii | 3.1313 |
C11···C13v | 3.408 (2) | H5···H4ii | 3.4550 |
C11···C18v | 3.4611 (18) | H5···H17 | 2.8769 |
C12···N1v | 3.534 (2) | H5···H17iv | 2.7727 |
C12···N2v | 3.5061 (19) | H5···H18 | 3.4278 |
C13···N1v | 3.4362 (19) | H5···H18iv | 2.4418 |
C13···C11v | 3.408 (2) | H6···O3v | 3.5738 |
C14···O2v | 3.4847 (18) | H6···O5 | 2.0733 |
C15···O2v | 3.5467 (17) | H6···C19viii | 3.4870 |
C15···C3v | 3.425 (2) | H6···H3ii | 3.5413 |
C16···C3v | 3.5874 (18) | H6···H12Bii | 3.3595 |
C17···O1ix | 3.413 (2) | H6···H14Aviii | 2.9852 |
C17···O2iv | 3.0969 (15) | H6···H15Bviii | 3.0796 |
C17···C1v | 3.347 (2) | H6···H17 | 2.7998 |
C17···C2v | 3.4872 (19) | H6···H18 | 2.5496 |
C18···O2iv | 3.2582 (16) | H7···O2v | 3.5098 |
C18···O5 | 3.3885 (16) | H7···O5vi | 3.2029 |
C18···N1v | 3.1900 (17) | H7···C4xi | 3.0931 |
C18···C2v | 3.5038 (19) | H7···C5xi | 3.2491 |
C18···C11v | 3.4611 (18) | H7···C10xi | 3.0983 |
C19···O5viii | 3.1664 (17) | H7···C19xv | 3.5754 |
O1···H4 | 2.5251 | H7···H2xi | 2.7132 |
O2···H2 | 2.6134 | H7···H8xv | 3.3791 |
O2···H5 | 2.7069 | H7···H11Axi | 2.7136 |
O3···H6 | 3.0551 | H7···H13Cxi | 2.9516 |
O3···H7 | 2.6534 | H7···H14Axv | 3.5658 |
O4···H8 | 2.6732 | H7···H16Cxv | 2.7801 |
O4···H9 | 2.4801 | H7···H17vi | 2.7717 |
N1···H1 | 2.4498 | H7···H18vi | 3.0174 |
N2···H5 | 2.3906 | H8···O2xi | 3.1894 |
N2···H10 | 2.6248 | H8···C4xi | 3.5614 |
C1···H5 | 3.2679 | H8···C15xv | 3.4404 |
C3···H1 | 3.2802 | H8···H2xi | 2.8772 |
C3···H2 | 2.6884 | H8···H7xv | 3.3791 |
C3···H5 | 2.7576 | H8···H8xv | 2.7580 |
C4···H3 | 3.2557 | H9···O1ix | 2.6230 |
C4···H11A | 2.5696 | H9···O1v | 3.4596 |
C4···H12B | 3.1436 | H9···O2iv | 2.6002 |
C4···H13C | 3.1436 | H9···C1ix | 3.1313 |
C5···H4 | 3.2972 | H9···C1v | 3.3502 |
C6···H2 | 3.2605 | H9···C3iv | 3.2617 |
C6···H11A | 3.3234 | H9···C4iv | 3.0509 |
C6···H12B | 2.7605 | H9···C8iv | 3.4940 |
C6···H13C | 2.7782 | H9···C9ix | 3.5961 |
C8···H4 | 3.2968 | H9···H1ix | 2.9731 |
C9···H1 | 3.1875 | H9···H1v | 3.4140 |
C9···H2 | 3.2584 | H9···H2iv | 2.3881 |
C9···H3 | 3.2399 | H9···H4ix | 3.5172 |
C10···H2 | 2.6780 | H10···O2iv | 2.8992 |
C10···H3 | 2.6698 | H10···O3v | 3.2467 |
C11···H1 | 2.5457 | H10···O5 | 2.8202 |
C11···H6 | 2.4080 | H10···N1v | 3.0018 |
C12···H7 | 2.6281 | H10···H4ix | 2.9367 |
C12···H10 | 2.6974 | H10···H14Aviii | 3.0995 |
C13···H6 | 2.4962 | H10···H18 | 2.5593 |
C13···H8 | 3.2867 | H11A···O3x | 3.5087 |
C13···H9 | 3.2692 | H11A···O4iv | 2.7373 |
C14···H10 | 3.2651 | H11A···C12x | 3.3379 |
C15···H9 | 3.2762 | H11A···C13x | 3.3981 |
C15···H14A | 2.6970 | H11A···C14x | 3.0798 |
C15···H16C | 2.7835 | H11A···C19iv | 3.0741 |
C16···H7 | 3.2575 | H11A···H7x | 2.7136 |
C16···H10 | 3.2648 | H11A···H12Bxiii | 3.0810 |
C16···H14A | 2.5828 | H11A···H14Aiv | 3.4356 |
C16···H15B | 3.1948 | H11A···H15Biv | 2.5934 |
C16···H16C | 2.6505 | H12B···N1ii | 3.0093 |
C17···H8 | 3.2812 | H12B···N2ii | 3.1500 |
C18···H6 | 2.5794 | H12B···C10xiii | 3.1944 |
C18···H7 | 3.2633 | H12B···C11ii | 3.4557 |
C19···H8 | 2.5204 | H12B···H1ii | 3.4139 |
H1···H5 | 3.4530 | H12B···H6ii | 3.3595 |
H2···H11A | 2.3603 | H12B···H11Axiii | 3.0810 |
H2···H12B | 3.3527 | H12B···H12Bxiii | 2.8819 |
H2···H13C | 3.3240 | H12B···H13Cxiii | 3.0808 |
H3···H4 | 2.3310 | H12B···H15Bxiv | 2.7976 |
H3···H12B | 2.7103 | H12B···H15Biv | 3.4853 |
H3···H13C | 2.7079 | H13C···O3x | 2.8693 |
H5···H6 | 2.1974 | H13C···C6xii | 3.4168 |
H6···H10 | 2.1755 | H13C···C12x | 3.2583 |
H7···H8 | 2.3430 | H13C···H3xii | 2.8860 |
H8···H14A | 2.2623 | H13C···H4xii | 3.5497 |
H8···H15B | 3.4901 | H13C···H7x | 2.9516 |
H8···H16C | 2.3453 | H13C···H12Bxiii | 3.0808 |
H9···H10 | 2.3234 | H13C···H15Bxiv | 3.0074 |
O1···H1i | 2.6612 | H14A···O2xi | 3.2341 |
O1···H9iii | 2.6230 | H14A···O5viii | 2.6683 |
O1···H9v | 3.4596 | H14A···N2viii | 3.5424 |
O2···H7v | 3.5098 | H14A···C13viii | 3.0288 |
O2···H8x | 3.1894 | H14A···C14viii | 3.4949 |
O2···H9iv | 2.6002 | H14A···C17viii | 3.1958 |
O2···H10iv | 2.8992 | H14A···C18viii | 2.8568 |
O2···H14Ax | 3.2341 | H14A···H6viii | 2.9852 |
O2···H17iv | 3.1820 | H14A···H7xv | 3.5658 |
O2···H18iv | 1.9585 | H14A···H10viii | 3.0995 |
O3···H3i | 2.9428 | H14A···H11Aiv | 3.4356 |
O3···H4i | 2.5018 | H14A···H17viii | 3.2070 |
O3···H5v | 3.5370 | H14A···H18viii | 2.5780 |
O3···H6v | 3.5738 | H15B···O5viii | 3.0892 |
O3···H10v | 3.2467 | H15B···N2viii | 3.4220 |
O3···H11Axi | 3.5087 | H15B···C10xvi | 3.3329 |
O3···H13Cxi | 2.8693 | H15B···C10iv | 3.4241 |
O3···H17vi | 1.9860 | H15B···C13viii | 3.5976 |
O3···H18vi | 3.1614 | H15B···H3xvi | 3.1317 |
O4···H1ix | 3.4948 | H15B···H6viii | 3.0796 |
O4···H2iv | 3.0040 | H15B···H11Aiv | 2.5934 |
O4···H11Aiv | 2.7373 | H15B···H12Bxvi | 2.7976 |
O5···H3ii | 2.9615 | H15B···H12Biv | 3.4853 |
O5···H5 | 2.7040 | H15B···H13Cxvi | 3.0074 |
O5···H5iv | 2.8429 | H15B···H17viii | 3.4492 |
O5···H6 | 2.0733 | H15B···H18viii | 3.4212 |
O5···H7vii | 3.2029 | H16C···O5viii | 3.2344 |
O5···H10 | 2.8202 | H16C···C4v | 2.9199 |
O5···H14Aviii | 2.6683 | H16C···C5v | 3.0378 |
O5···H15Bviii | 3.0892 | H16C···C6v | 3.2428 |
O5···H16Cviii | 3.2344 | H16C···C7v | 3.3992 |
N1···H4i | 3.1154 | H16C···C8v | 3.0929 |
N1···H10v | 3.0018 | H16C···C9v | 3.3280 |
N1···H12Bii | 3.0093 | H16C···H2v | 3.3063 |
N2···H12Bii | 3.1500 | H16C···H7xv | 2.7801 |
N2···H14Aviii | 3.5424 | H16C···H17viii | 3.3865 |
N2···H15Bviii | 3.4220 | H16C···H18viii | 3.2768 |
N2···H18 | 3.4279 | H17···O2iv | 3.1820 |
C1···H1i | 3.4987 | H17···O3vii | 1.9860 |
C1···H2ii | 3.4871 | H17···C6ii | 3.3703 |
C1···H9iii | 3.1313 | H17···C11iv | 3.4096 |
C1···H9v | 3.3502 | H17···C12vii | 2.9300 |
C2···H18iv | 3.4662 | H17···C13vii | 3.3762 |
C3···H9iv | 3.2617 | H17···C14vii | 3.2493 |
C3···H18iv | 2.9714 | H17···C19viii | 3.5419 |
C4···H1ii | 3.2645 | H17···H3ii | 2.6475 |
C4···H7x | 3.0931 | H17···H4ii | 3.3353 |
C4···H8x | 3.5614 | H17···H5 | 2.8769 |
C4···H9iv | 3.0509 | H17···H5iv | 2.7727 |
C4···H16Cv | 2.9199 | H17···H6 | 2.7998 |
C5···H1ii | 3.4193 | H17···H7vii | 2.7717 |
C5···H7x | 3.2491 | H17···H14Aviii | 3.2070 |
C5···H16Cv | 3.0378 | H17···H15Bviii | 3.4492 |
C6···H5ii | 3.1539 | H17···H16Cviii | 3.3865 |
C6···H13Cxii | 3.4168 | H18···O2iv | 1.9585 |
C6···H16Cv | 3.2428 | H18···O3vii | 3.1614 |
C6···H17ii | 3.3703 | H18···N2 | 3.4279 |
C7···H1i | 3.4139 | H18···C2iv | 3.4662 |
C7···H5ii | 3.3413 | H18···C3iv | 2.9714 |
C7···H16Cv | 3.3992 | H18···C11iv | 3.0847 |
C8···H9iv | 3.4940 | H18···C14vii | 3.3794 |
C8···H16Cv | 3.0929 | H18···C18 | 3.1229 |
C9···H1i | 3.4026 | H18···C19viii | 3.2485 |
C9···H9iii | 3.5961 | H18···H5 | 3.4278 |
C9···H16Cv | 3.3280 | H18···H5iv | 2.4418 |
C10···H7x | 3.0983 | H18···H6 | 2.5496 |
C10···H12Bxiii | 3.1944 | H18···H7vii | 3.0174 |
C10···H15Bxiv | 3.3329 | H18···H10 | 2.5593 |
C10···H15Biv | 3.4241 | H18···H14Aviii | 2.5780 |
C11···H3ii | 3.4417 | H18···H15Bviii | 3.4212 |
C11···H12Bii | 3.4557 | H18···H16Cviii | 3.2768 |
C11···H17iv | 3.4096 | ||
C1—O1—C9 | 118.30 (11) | C16—C17—C18 | 120.28 (13) |
C16—O4—C19 | 116.81 (11) | C13—C18—C17 | 120.42 (9) |
N2—N1—C11 | 115.03 (10) | H17—O5—H18 | 104.049 |
N1—N2—C12 | 119.09 (10) | N1—N2—H6 | 120.456 |
O1—C1—C2 | 125.30 (9) | C12—N2—H6 | 120.455 |
C1—C2—C3 | 119.92 (10) | O1—C1—H1 | 117.348 |
C1—C2—C11 | 119.51 (9) | C2—C1—H1 | 117.351 |
C3—C2—C11 | 120.57 (11) | C5—C4—H2 | 119.347 |
O2—C3—C2 | 123.39 (10) | C8—C4—H2 | 119.353 |
O2—C3—C8 | 122.09 (9) | C5—C6—H3 | 119.062 |
C2—C3—C8 | 114.51 (11) | C7—C6—H3 | 119.061 |
C5—C4—C8 | 121.30 (12) | C6—C7—H4 | 120.966 |
C4—C5—C6 | 118.44 (10) | C9—C7—H4 | 120.967 |
C4—C5—C10 | 121.41 (12) | C5—C10—H11A | 109.468 |
C6—C5—C10 | 120.13 (11) | C5—C10—H12B | 109.473 |
C5—C6—C7 | 121.88 (11) | C5—C10—H13C | 109.474 |
C6—C7—C9 | 118.07 (12) | H11A—C10—H12B | 109.466 |
C3—C8—C4 | 121.97 (11) | H11A—C10—H13C | 109.475 |
C3—C8—C9 | 120.11 (9) | H12B—C10—H13C | 109.472 |
C4—C8—C9 | 117.92 (11) | N1—C11—H5 | 120.708 |
O1—C9—C7 | 115.96 (11) | C2—C11—H5 | 120.713 |
O1—C9—C8 | 121.73 (10) | C13—C14—H7 | 119.332 |
C7—C9—C8 | 122.31 (9) | C15—C14—H7 | 119.329 |
N1—C11—C2 | 118.58 (11) | C14—C15—H8 | 120.561 |
O3—C12—N2 | 122.85 (11) | C16—C15—H8 | 120.551 |
O3—C12—C13 | 122.70 (10) | C16—C17—H9 | 119.859 |
N2—C12—C13 | 114.45 (10) | C18—C17—H9 | 119.864 |
C12—C13—C14 | 119.21 (12) | C13—C18—H10 | 119.788 |
C12—C13—C18 | 121.95 (9) | C17—C18—H10 | 119.793 |
C14—C13—C18 | 118.82 (11) | O4—C19—H14A | 109.469 |
C13—C14—C15 | 121.34 (13) | O4—C19—H15B | 109.476 |
C14—C15—C16 | 118.89 (10) | O4—C19—H16C | 109.470 |
O4—C16—C15 | 124.87 (9) | H14A—C19—H15B | 109.472 |
O4—C16—C17 | 114.91 (12) | H14A—C19—H16C | 109.471 |
C15—C16—C17 | 120.21 (11) | H15B—C19—H16C | 109.469 |
C1—O1—C9—C7 | −178.27 (10) | C6—C5—C10—H11A | 178.6 |
C1—O1—C9—C8 | 1.07 (17) | C6—C5—C10—H12B | 58.6 |
C9—O1—C1—C2 | −2.91 (18) | C6—C5—C10—H13C | −61.4 |
C9—O1—C1—H1 | 177.1 | C10—C5—C6—C7 | −176.19 (11) |
C16—O4—C19—H14A | −54.8 | C10—C5—C6—H3 | 3.8 |
C16—O4—C19—H15B | −174.8 | C5—C6—C7—C9 | 0.2 (2) |
C16—O4—C19—H16C | 65.2 | C5—C6—C7—H4 | −179.8 |
C19—O4—C16—C15 | −3.73 (17) | H3—C6—C7—C9 | −179.8 |
C19—O4—C16—C17 | 177.18 (10) | H3—C6—C7—H4 | 0.2 |
N2—N1—C11—C2 | −178.93 (10) | C6—C7—C9—O1 | 176.77 (11) |
N2—N1—C11—H5 | 1.1 | C6—C7—C9—C8 | −2.58 (19) |
C11—N1—N2—C12 | −169.22 (11) | H4—C7—C9—O1 | −3.2 |
C11—N1—N2—H6 | 10.8 | H4—C7—C9—C8 | 177.4 |
N1—N2—C12—O3 | −4.41 (19) | C3—C8—C9—O1 | 2.10 (18) |
N1—N2—C12—C13 | 175.96 (10) | C3—C8—C9—C7 | −178.59 (10) |
H6—N2—C12—O3 | 175.6 | C4—C8—C9—O1 | −177.05 (10) |
H6—N2—C12—C13 | −4.0 | C4—C8—C9—C7 | 2.26 (18) |
O1—C1—C2—C3 | 1.3 (2) | O3—C12—C13—C14 | −30.86 (18) |
O1—C1—C2—C11 | −177.80 (11) | O3—C12—C13—C18 | 147.39 (12) |
H1—C1—C2—C3 | −178.7 | N2—C12—C13—C14 | 148.77 (11) |
H1—C1—C2—C11 | 2.2 | N2—C12—C13—C18 | −32.97 (17) |
C1—C2—C3—O2 | −178.28 (12) | C12—C13—C14—C15 | −179.76 (11) |
C1—C2—C3—C8 | 1.82 (17) | C12—C13—C14—H7 | 0.2 |
C1—C2—C11—N1 | 21.42 (18) | C12—C13—C18—C17 | −178.28 (10) |
C1—C2—C11—H5 | −158.6 | C12—C13—C18—H10 | 1.7 |
C3—C2—C11—N1 | −157.72 (11) | C14—C13—C18—C17 | −0.02 (18) |
C3—C2—C11—H5 | 22.3 | C14—C13—C18—H10 | 180.0 |
C11—C2—C3—O2 | 0.86 (18) | C18—C13—C14—C15 | 1.93 (19) |
C11—C2—C3—C8 | −179.04 (10) | C18—C13—C14—H7 | −178.1 |
O2—C3—C8—C4 | −4.21 (19) | C13—C14—C15—C16 | −2.29 (19) |
O2—C3—C8—C9 | 176.67 (11) | C13—C14—C15—H8 | 177.7 |
C2—C3—C8—C4 | 175.68 (10) | H7—C14—C15—C16 | 177.7 |
C2—C3—C8—C9 | −3.43 (16) | H7—C14—C15—H8 | −2.3 |
C5—C4—C8—C3 | −178.65 (11) | C14—C15—C16—O4 | −178.30 (11) |
C5—C4—C8—C9 | 0.48 (18) | C14—C15—C16—C17 | 0.75 (19) |
C8—C4—C5—C6 | −2.74 (18) | H8—C15—C16—O4 | 1.7 |
C8—C4—C5—C10 | 175.85 (10) | H8—C15—C16—C17 | −179.3 |
H2—C4—C5—C6 | 177.3 | O4—C16—C17—C18 | −179.74 (10) |
H2—C4—C5—C10 | −4.1 | O4—C16—C17—H9 | 0.3 |
H2—C4—C8—C3 | 1.3 | C15—C16—C17—C18 | 1.12 (19) |
H2—C4—C8—C9 | −179.5 | C15—C16—C17—H9 | −178.9 |
C4—C5—C6—C7 | 2.42 (19) | C16—C17—C18—C13 | −1.49 (19) |
C4—C5—C6—H3 | −177.6 | C16—C17—C18—H10 | 178.5 |
C4—C5—C10—H11A | −0.0 | H9—C17—C18—C13 | 178.5 |
C4—C5—C10—H12B | −120.0 | H9—C17—C18—H10 | −1.5 |
C4—C5—C10—H13C | 120.0 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x, y, z+1; (iv) −x+1, −y+1, −z; (v) −x, −y+1, −z; (vi) x−1, y, z; (vii) x+1, y, z; (viii) −x, −y, −z−1; (ix) x, y, z−1; (x) x+1, y+1, z+1; (xi) x−1, y−1, z−1; (xii) −x+1, −y+2, −z+2; (xiii) −x+2, −y+2, −z+2; (xiv) x+1, y+1, z+2; (xv) −x−1, −y, −z−1; (xvi) x−1, y−1, z−2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H17···O3vii | 0.86 | 1.99 | 2.8465 (13) | 178 |
O5—H18···O2iv | 0.87 | 1.96 | 2.8274 (16) | 176 |
N2—H6···O5 | 0.88 | 2.07 | 2.9341 (14) | 166 |
Symmetry codes: (iv) −x+1, −y+1, −z; (vii) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H17···O3i | 0.861 | 1.986 | 2.8465 (13) | 178 |
O5—H18···O2ii | 0.871 | 1.958 | 2.8274 (16) | 176 |
N2—H6···O5 | 0.880 | 2.073 | 2.9341 (14) | 166 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z. |
Schiff base derivatives of 3-formyl chromones have attracted much attention due to their biological functions such as enzyme inhibition (Khan et al. 2009; Tu et al. 2013). We herein report the crystal structure of the title compound, which was obtained from the condensation reaction of 6-methyl-3-formylchromone with 4-methoxybenzoylhydrazide in benzene.
The 4H-chromen-4-one segment segment is slightly twisted with a dihedral angle between the two 6-membered rings of 3.30 (5)°. The dihedral angles between the pyranone ring and the hydrazide plane (C11/N1/N2/C12) and between the pyranone ring and the benzene ring of the p-methoxybenzene unit are 26.69 (4) and 2.23 (3)°, respectively. The molecule is connected to the solvent water molecule byan N–H···O hydrogen bond.
In the crystal, there are π-π stacking interactions between centrosymmetrically-related pyranone rings [centroid–centroidi distance = 3.5394 (9) Å, i: –x + 1, –y + 1, –z + 1] as well as bridges formed by the water molecules via O–H···O hydrogen bonds (Fig. 2).