organic compounds
(E)-3,4,5-Trimethoxy-N′-[(4-oxo-4H-chromen-3-yl)methylidene]benzohydrazide
aSchool of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan
*Correspondence e-mail: ishi206@u-shizuoka-ken.ac.jp
In the title chromone-tethered benzohydrazide derivative, C20H18N2O6, the atoms of the E-3-(hydrazonomethyl)-4H-chromen-4-one segment are essentially coplanar, the largest deviation being 0.065 (6) Å. The dihedral angle between this segment and the benzene ring of the trimethoxybenzene unit is 40.18 (10) Å. In the crystal, the molecule is linked to its inverse-symmetry equivalent by pairs of N—H⋯O hydrogen bonds and C—H⋯π interactions. The –CH=N—NH– segment is stacked on the benzene ring of the chromone unit of a translation-related equivalent molecule [centroid–centroid distance = 3.413 (6) Å].
CCDC reference: 991676
Related literature
For the biological activity of related compounds, see: Khan et al. (2009); Tu et al. (2013). For related structures, see: Wang et al. (2007); Qin et al. (2009); Ishikawa et al. (2013a,b,c).
Experimental
Crystal data
|
|
Data collection: WinAFC (Rigaku, 1999); cell WinAFC; data reduction: WinAFC; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure.
Supporting information
CCDC reference: 991676
10.1107/S1600536814005753/zl2582sup1.cif
contains datablocks General, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814005753/zl2582Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814005753/zl2582Isup3.cml
3,4,5-Trimethoxybenzoylhydrazide (1.00 mmol) and 3-formylchromone (1.00 mmol) 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 75.6%). 1H NMR (400 MHz, DMSO-d6): δ = 3.74 (s, 3H), 3.88 (br s, 6H), 7.28 (s, 2H), 7.57 (t, 1H, J = 7.6 Hz), 7.75 (d, 1H, J = 8.3 Hz), 7.88 (t, 1H, J = 7.8 Hz), 8.16 (d, 1H, J = 7.8 Hz), 8.67 (s, 1H), 8.87 (s, 1H), 11.82 (s, 1H). DART-MS calcd for [C20H18N2O6 + H+]: 383.116, found 383.189. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an acetonitrile 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)].
Data collection: WinAFC (Rigaku, 1999); cell
WinAFC (Rigaku, 1999); data reduction: WinAFC (Rigaku, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).C20H18N2O6 | Z = 2 |
Mr = 382.37 | F(000) = 400.00 |
Triclinic, P1 | Dx = 1.461 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 6.628 (7) Å | Cell parameters from 25 reflections |
b = 11.029 (18) Å | θ = 15.1–17.5° |
c = 12.544 (18) Å | µ = 0.11 mm−1 |
α = 105.34 (12)° | T = 100 K |
β = 96.94 (10)° | Plate, yellow |
γ = 95.88 (10)° | 0.40 × 0.18 × 0.12 mm |
V = 869 (2) Å3 |
Rigaku AFC-7R diffractometer | θmax = 27.5° |
ω–2θ scans | h = −8→4 |
4902 measured reflections | k = −14→14 |
3982 independent reflections | l = −16→16 |
1962 reflections with F2 > 2σ(F2) | 3 standard reflections every 150 reflections |
Rint = 0.040 | intensity decay: 1.9% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.208 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.093P)2 + 0.2643P] where P = (Fo2 + 2Fc2)/3 |
3982 reflections | (Δ/σ)max < 0.001 |
256 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
Primary atom site location: structure-invariant direct methods |
C20H18N2O6 | γ = 95.88 (10)° |
Mr = 382.37 | V = 869 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.628 (7) Å | Mo Kα radiation |
b = 11.029 (18) Å | µ = 0.11 mm−1 |
c = 12.544 (18) Å | T = 100 K |
α = 105.34 (12)° | 0.40 × 0.18 × 0.12 mm |
β = 96.94 (10)° |
Rigaku AFC-7R diffractometer | Rint = 0.040 |
4902 measured reflections | 3 standard reflections every 150 reflections |
3982 independent reflections | intensity decay: 1.9% |
1962 reflections with F2 > 2σ(F2) |
R[F2 > 2σ(F2)] = 0.068 | 0 restraints |
wR(F2) = 0.208 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.30 e Å−3 |
3982 reflections | Δρmin = −0.34 e Å−3 |
256 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 | 1.0097 (4) | 0.3621 (3) | 0.4260 (3) | 0.0470 (8) | |
O2 | 0.7771 (4) | 0.0019 (3) | 0.4167 (3) | 0.0416 (8) | |
O3 | 0.2618 (4) | 0.4738 (3) | 0.6820 (2) | 0.0369 (7) | |
O4 | −0.3434 (4) | 0.4096 (3) | 0.8991 (3) | 0.0413 (7) | |
O5 | −0.2570 (4) | 0.2233 (3) | 0.9857 (2) | 0.0357 (7) | |
O6 | 0.0813 (4) | 0.1163 (3) | 0.9562 (2) | 0.0359 (7) | |
N1 | 0.5082 (5) | 0.3018 (3) | 0.5846 (3) | 0.0267 (7) | |
N2 | 0.3513 (5) | 0.2739 (3) | 0.6410 (3) | 0.0266 (7) | |
C1 | 0.8476 (6) | 0.3386 (4) | 0.4747 (4) | 0.0375 (10) | |
C2 | 0.7663 (5) | 0.2226 (3) | 0.4787 (3) | 0.0257 (8) | |
C3 | 0.8540 (6) | 0.1112 (4) | 0.4232 (3) | 0.0298 (9) | |
C4 | 1.1452 (7) | 0.0413 (5) | 0.3228 (4) | 0.0539 (13) | |
C5 | 1.3098 (8) | 0.0687 (7) | 0.2729 (4) | 0.0764 (19) | |
C6 | 1.3754 (7) | 0.1940 (7) | 0.2766 (4) | 0.077 (2) | |
C7 | 1.2771 (7) | 0.2920 (6) | 0.3295 (4) | 0.0602 (15) | |
C8 | 1.0377 (6) | 0.1377 (4) | 0.3740 (3) | 0.0350 (10) | |
C9 | 1.1067 (6) | 0.2617 (5) | 0.3765 (3) | 0.0402 (10) | |
C10 | 0.5918 (6) | 0.2068 (3) | 0.5368 (3) | 0.0267 (8) | |
C11 | 0.2483 (6) | 0.3672 (4) | 0.6948 (3) | 0.0267 (8) | |
C12 | 0.1178 (6) | 0.3282 (3) | 0.7727 (3) | 0.0264 (8) | |
C13 | −0.0553 (6) | 0.3875 (4) | 0.7941 (3) | 0.0297 (8) | |
C14 | −0.1749 (5) | 0.3547 (4) | 0.8687 (3) | 0.0305 (9) | |
C15 | −0.1287 (6) | 0.2606 (4) | 0.9181 (3) | 0.0292 (8) | |
C16 | 0.0466 (6) | 0.2031 (4) | 0.8991 (3) | 0.0277 (8) | |
C17 | 0.1710 (5) | 0.2381 (3) | 0.8267 (3) | 0.0254 (8) | |
C18 | −0.3580 (6) | 0.5322 (4) | 0.8866 (4) | 0.0409 (10) | |
C19 | −0.1850 (7) | 0.2802 (5) | 1.1040 (4) | 0.0505 (12) | |
C20 | 0.2601 (6) | 0.0549 (4) | 0.9390 (4) | 0.0399 (10) | |
H1 | 0.7842 | 0.4090 | 0.5095 | 0.0450* | |
H2 | 1.1038 | −0.0438 | 0.3228 | 0.0647* | |
H3 | 1.3791 | 0.0024 | 0.2357 | 0.0916* | |
H4 | 1.4902 | 0.2123 | 0.2420 | 0.0920* | |
H5 | 1.3246 | 0.3776 | 0.3336 | 0.0723* | |
H6 | 0.5394 | 0.1242 | 0.5392 | 0.0321* | |
H7 | 0.3172 | 0.1951 | 0.6423 | 0.0319* | |
H8 | −0.0910 | 0.4496 | 0.7580 | 0.0357* | |
H9 | 0.2919 | 0.2004 | 0.8144 | 0.0304* | |
H10A | −0.3952 | 0.5262 | 0.8071 | 0.0491* | |
H11B | −0.2255 | 0.5863 | 0.9158 | 0.0491* | |
H12C | −0.4636 | 0.5692 | 0.9281 | 0.0491* | |
H13A | −0.2856 | 0.2532 | 1.1473 | 0.0606* | |
H14B | −0.1676 | 0.3729 | 1.1201 | 0.0606* | |
H15C | −0.0532 | 0.2530 | 1.1245 | 0.0606* | |
H16A | 0.2699 | −0.0048 | 0.9843 | 0.0479* | |
H17B | 0.3828 | 0.1189 | 0.9611 | 0.0479* | |
H18C | 0.2499 | 0.0088 | 0.8597 | 0.0479* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0324 (16) | 0.0546 (18) | 0.068 (2) | −0.0022 (14) | 0.0109 (15) | 0.0423 (16) |
O2 | 0.0325 (15) | 0.0253 (14) | 0.0578 (18) | −0.0070 (11) | 0.0195 (13) | −0.0058 (13) |
O3 | 0.0488 (17) | 0.0308 (15) | 0.0379 (16) | 0.0129 (12) | 0.0143 (13) | 0.0152 (12) |
O4 | 0.0326 (16) | 0.0417 (16) | 0.0572 (19) | 0.0097 (13) | 0.0201 (14) | 0.0194 (14) |
O5 | 0.0236 (14) | 0.0435 (16) | 0.0409 (16) | −0.0044 (12) | 0.0095 (12) | 0.0147 (13) |
O6 | 0.0299 (14) | 0.0417 (15) | 0.0433 (16) | 0.0056 (12) | 0.0098 (12) | 0.0221 (13) |
N1 | 0.0302 (17) | 0.0241 (15) | 0.0243 (16) | −0.0015 (13) | 0.0062 (13) | 0.0053 (13) |
N2 | 0.0323 (17) | 0.0190 (14) | 0.0276 (16) | −0.0003 (12) | 0.0092 (13) | 0.0042 (12) |
C1 | 0.032 (3) | 0.036 (2) | 0.048 (3) | −0.0045 (17) | 0.0081 (18) | 0.0208 (19) |
C2 | 0.0240 (18) | 0.0249 (18) | 0.0260 (19) | −0.0043 (14) | 0.0037 (15) | 0.0065 (15) |
C3 | 0.0259 (19) | 0.032 (2) | 0.0251 (19) | −0.0047 (16) | 0.0067 (15) | −0.0006 (15) |
C4 | 0.031 (3) | 0.072 (3) | 0.041 (3) | −0.004 (2) | 0.0101 (19) | −0.015 (3) |
C5 | 0.033 (3) | 0.135 (6) | 0.036 (3) | −0.010 (3) | 0.011 (2) | −0.013 (3) |
C6 | 0.024 (3) | 0.171 (7) | 0.034 (3) | −0.012 (4) | 0.009 (2) | 0.034 (4) |
C7 | 0.023 (3) | 0.123 (5) | 0.045 (3) | −0.007 (3) | 0.001 (2) | 0.051 (3) |
C8 | 0.0203 (18) | 0.055 (3) | 0.0217 (19) | −0.0055 (17) | 0.0030 (15) | 0.0023 (18) |
C9 | 0.0204 (19) | 0.075 (3) | 0.031 (2) | −0.0067 (19) | 0.0033 (16) | 0.031 (2) |
C10 | 0.0296 (19) | 0.0195 (17) | 0.0302 (19) | −0.0051 (14) | 0.0062 (15) | 0.0078 (15) |
C11 | 0.032 (2) | 0.0265 (18) | 0.0203 (17) | 0.0056 (15) | 0.0046 (15) | 0.0026 (14) |
C12 | 0.0280 (19) | 0.0243 (18) | 0.0238 (18) | −0.0009 (15) | 0.0049 (15) | 0.0031 (15) |
C13 | 0.0258 (19) | 0.0290 (19) | 0.035 (2) | 0.0061 (15) | 0.0045 (16) | 0.0095 (16) |
C14 | 0.0208 (19) | 0.0310 (19) | 0.035 (2) | 0.0027 (15) | 0.0042 (16) | 0.0013 (16) |
C15 | 0.0244 (19) | 0.0296 (19) | 0.029 (2) | −0.0046 (15) | 0.0051 (15) | 0.0033 (16) |
C16 | 0.0220 (18) | 0.0296 (19) | 0.0296 (19) | −0.0007 (15) | 0.0029 (15) | 0.0073 (15) |
C17 | 0.0193 (17) | 0.0288 (18) | 0.0266 (18) | 0.0010 (14) | 0.0038 (14) | 0.0061 (15) |
C18 | 0.036 (3) | 0.040 (3) | 0.050 (3) | 0.0058 (18) | 0.0121 (19) | 0.0155 (19) |
C19 | 0.045 (3) | 0.061 (3) | 0.046 (3) | −0.004 (2) | 0.022 (2) | 0.013 (3) |
C20 | 0.025 (2) | 0.048 (3) | 0.056 (3) | 0.0045 (18) | 0.0079 (18) | 0.031 (2) |
O1—C1 | 1.335 (6) | C12—C13 | 1.397 (6) |
O1—C9 | 1.380 (6) | C12—C17 | 1.394 (6) |
O2—C3 | 1.237 (5) | C13—C14 | 1.390 (6) |
O3—C11 | 1.224 (5) | C14—C15 | 1.384 (6) |
O4—C14 | 1.371 (5) | C15—C16 | 1.396 (6) |
O4—C18 | 1.414 (6) | C16—C17 | 1.398 (6) |
O5—C15 | 1.378 (5) | N2—H7 | 0.880 |
O5—C19 | 1.448 (6) | C1—H1 | 0.950 |
O6—C16 | 1.360 (6) | C4—H2 | 0.950 |
O6—C20 | 1.434 (5) | C5—H3 | 0.950 |
N1—N2 | 1.380 (5) | C6—H4 | 0.950 |
N1—C10 | 1.278 (5) | C7—H5 | 0.950 |
N2—C11 | 1.367 (5) | C10—H6 | 0.950 |
C1—C2 | 1.352 (6) | C13—H8 | 0.950 |
C2—C3 | 1.457 (6) | C17—H9 | 0.950 |
C2—C10 | 1.459 (6) | C18—H10A | 0.980 |
C3—C8 | 1.468 (6) | C18—H11B | 0.980 |
C4—C5 | 1.368 (8) | C18—H12C | 0.980 |
C4—C8 | 1.399 (7) | C19—H13A | 0.980 |
C5—C6 | 1.392 (11) | C19—H14B | 0.980 |
C6—C7 | 1.380 (9) | C19—H15C | 0.980 |
C7—C9 | 1.387 (7) | C20—H16A | 0.980 |
C8—C9 | 1.387 (7) | C20—H17B | 0.980 |
C11—C12 | 1.496 (6) | C20—H18C | 0.980 |
O1···C3 | 2.843 (7) | C10···H8ii | 3.5772 |
O2···C1 | 3.559 (8) | C11···H10Aii | 2.7721 |
O2···C4 | 2.877 (6) | C11···H12Cii | 3.3916 |
O2···C10 | 2.845 (6) | C11···H14Bvii | 3.3148 |
O3···N1 | 2.765 (6) | C12···H2v | 3.1739 |
O3···C13 | 2.883 (6) | C12···H14Bvii | 3.1794 |
O3···C17 | 3.586 (7) | C13···H14Bvii | 2.7634 |
O4···O5 | 2.646 (6) | C14···H11Bvii | 3.4286 |
O4···C19 | 3.367 (8) | C14···H14Bvii | 3.5351 |
O5···O6 | 2.659 (5) | C15···H2v | 3.3544 |
O6···C19 | 3.081 (7) | C15···H3v | 3.1886 |
N1···C1 | 2.825 (6) | C15···H11Bvii | 2.9753 |
N2···C17 | 2.842 (6) | C15···H16Aix | 3.4488 |
C1···C7 | 3.570 (8) | C16···H2v | 2.8659 |
C1···C8 | 2.751 (7) | C16···H3v | 3.3864 |
C2···C9 | 2.777 (6) | C16···H11Bvii | 2.8478 |
C4···C7 | 2.790 (10) | C16···H12Cvii | 3.5908 |
C5···C9 | 2.753 (9) | C16···H16Aix | 3.5794 |
C6···C8 | 2.769 (7) | C17···H2v | 2.7705 |
C10···C11 | 3.507 (7) | C17···H11Bvii | 3.2523 |
C12···C15 | 2.782 (7) | C17···H12Cvii | 3.4633 |
C13···C16 | 2.795 (7) | C18···H5iii | 3.1966 |
C13···C18 | 2.856 (7) | C18···H12Cviii | 3.1347 |
C14···C17 | 2.780 (6) | C18···H13Aviii | 3.5765 |
C14···C19 | 3.272 (8) | C18···H14Bviii | 3.4123 |
C15···C18 | 3.586 (8) | C18···H14Bvii | 3.5508 |
C16···C19 | 3.122 (7) | C18···H15Cvii | 3.4644 |
C17···C20 | 2.821 (7) | C19···H4xii | 3.0738 |
O1···O1i | 3.141 (7) | C19···H8vii | 3.2579 |
O1···O3ii | 3.289 (7) | C19···H11Bvii | 3.0282 |
O1···O3iii | 3.119 (6) | C19···H12Cviii | 3.0436 |
O1···C1i | 3.201 (8) | C19···H16Aix | 2.9135 |
O1···C11ii | 3.531 (7) | C19···H17Bvi | 3.2570 |
O2···O2iv | 3.417 (6) | C19···H18Cix | 3.3301 |
O2···N2v | 2.942 (6) | C20···H3iv | 3.4296 |
O2···C3iv | 3.511 (6) | C20···H13Aix | 3.3118 |
O2···C4iv | 3.411 (8) | C20···H15Cix | 3.3767 |
O2···C8iv | 3.539 (7) | C20···H16Axiii | 3.2931 |
O2···C10v | 3.394 (6) | C20···H17Bxiii | 3.5118 |
O2···C17v | 3.552 (7) | H1···O1i | 2.6152 |
O3···O1vi | 3.289 (7) | H1···O3ii | 3.5039 |
O3···O1iii | 3.119 (6) | H1···O3iii | 3.0140 |
O3···C1vi | 3.451 (7) | H1···C1i | 3.4562 |
O3···C1iii | 3.285 (7) | H1···C7i | 3.4734 |
O3···C18ii | 3.252 (7) | H1···C9i | 3.4959 |
O3···C19vii | 3.404 (8) | H1···H1i | 3.3925 |
O4···N2vi | 3.472 (7) | H1···H5vi | 3.4678 |
O4···C11vi | 3.397 (6) | H1···H5i | 2.8587 |
O4···C17vi | 3.449 (6) | H1···H8ii | 3.0273 |
O4···C18viii | 3.491 (7) | H2···O2iv | 3.1647 |
O5···C20vi | 3.433 (6) | H2···O6v | 3.4165 |
O5···C20ix | 3.440 (8) | H2···C3iv | 3.4444 |
O6···O6ix | 3.188 (6) | H2···C10iv | 3.4588 |
O6···C4v | 3.536 (8) | H2···C12v | 3.1739 |
O6···C20ix | 3.402 (7) | H2···C15v | 3.3544 |
N1···C7vi | 3.346 (8) | H2···C16v | 2.8659 |
N1···C9vi | 3.400 (7) | H2···C17v | 2.7705 |
N1···C13ii | 3.530 (7) | H2···H6iv | 3.1034 |
N2···O2v | 2.942 (6) | H2···H7v | 3.2391 |
N2···O4ii | 3.472 (7) | H2···H9v | 3.0382 |
N2···C8vi | 3.579 (7) | H2···H18Cv | 3.2006 |
N2···C9vi | 3.475 (7) | H3···O2ii | 3.2680 |
C1···O1i | 3.201 (8) | H3···O5v | 3.1552 |
C1···O3ii | 3.451 (7) | H3···O6v | 3.5440 |
C1···O3iii | 3.285 (7) | H3···C3ii | 3.5809 |
C1···C11ii | 3.517 (7) | H3···C15v | 3.1886 |
C2···C6vi | 3.326 (7) | H3···C16v | 3.3864 |
C3···O2iv | 3.511 (6) | H3···C20iv | 3.4296 |
C4···O2iv | 3.411 (8) | H3···H6iv | 3.4770 |
C4···O6v | 3.536 (8) | H3···H9iv | 3.2772 |
C4···C16v | 3.332 (8) | H3···H16Ax | 3.1271 |
C4···C17v | 3.475 (8) | H3···H17Biv | 3.1628 |
C5···C10ii | 3.468 (8) | H3···H18Civ | 2.8620 |
C6···C2ii | 3.326 (7) | H4···O3i | 3.5084 |
C6···C10ii | 3.364 (8) | H4···C1ii | 3.4026 |
C7···N1ii | 3.346 (8) | H4···C2ii | 3.2626 |
C7···C10ii | 3.519 (8) | H4···C3ii | 3.5766 |
C8···O2iv | 3.539 (7) | H4···C19xi | 3.0738 |
C8···N2ii | 3.579 (7) | H4···H10Aiii | 3.2117 |
C9···N1ii | 3.400 (7) | H4···H13Axi | 2.0967 |
C9···N2ii | 3.475 (7) | H4···H14Bxi | 3.4738 |
C10···O2v | 3.394 (6) | H4···H15Cxi | 3.5609 |
C10···C5vi | 3.468 (8) | H4···H16Ax | 3.5157 |
C10···C6vi | 3.364 (8) | H4···H17Bx | 3.3622 |
C10···C7vi | 3.519 (8) | H4···H18Civ | 3.2072 |
C11···O1vi | 3.531 (7) | H5···O3i | 3.1009 |
C11···O4ii | 3.397 (6) | H5···N1ii | 3.5731 |
C11···C1vi | 3.517 (7) | H5···N1i | 3.4325 |
C11···C18ii | 3.332 (7) | H5···C18iii | 3.1966 |
C13···N1vi | 3.530 (7) | H5···H1ii | 3.4678 |
C16···C4v | 3.332 (8) | H5···H1i | 2.8587 |
C17···O2v | 3.552 (7) | H5···H8iii | 2.9465 |
C17···O4ii | 3.449 (6) | H5···H10Aiii | 2.3551 |
C17···C4v | 3.475 (8) | H5···H11Biii | 3.2546 |
C18···O3vi | 3.252 (7) | H5···H15Cx | 3.2923 |
C18···O4viii | 3.491 (7) | H6···O2v | 2.5946 |
C18···C11vi | 3.332 (7) | H6···C4vi | 3.3930 |
C19···O3vii | 3.404 (8) | H6···C4iv | 3.5039 |
C19···C20ix | 3.565 (9) | H6···C5vi | 3.3690 |
C20···O5ii | 3.433 (6) | H6···C10v | 3.5073 |
C20···O5ix | 3.440 (8) | H6···H2iv | 3.1034 |
C20···O6ix | 3.402 (7) | H6···H3iv | 3.4770 |
C20···C19ix | 3.565 (9) | H6···H6v | 2.6279 |
O1···H5 | 2.5194 | H7···O2v | 2.1022 |
O2···H2 | 2.6183 | H7···C3v | 3.3006 |
O2···H6 | 2.5661 | H7···C8vi | 3.5060 |
O3···H7 | 3.0489 | H7···H2v | 3.2391 |
O3···H8 | 2.6446 | H8···O1iii | 3.5409 |
O4···H8 | 2.6652 | H8···N1vi | 3.2075 |
O4···H14B | 3.0194 | H8···C1vi | 3.3969 |
O6···H9 | 2.6793 | H8···C7iii | 3.5908 |
O6···H15C | 2.5638 | H8···C10vi | 3.5772 |
N1···H1 | 2.4883 | H8···C19vii | 3.2579 |
N2···H6 | 2.3661 | H8···H1vi | 3.0273 |
N2···H9 | 2.5728 | H8···H5iii | 2.9465 |
C1···H6 | 3.2916 | H8···H14Bvii | 2.4905 |
C3···H1 | 3.2753 | H8···H15Cvii | 3.2100 |
C3···H2 | 2.6819 | H9···O2v | 3.1049 |
C3···H6 | 2.6773 | H9···O4ii | 3.0390 |
C4···H4 | 3.2406 | H9···O5ii | 3.4102 |
C5···H5 | 3.2771 | H9···H2v | 3.0382 |
C6···H2 | 3.2470 | H9···H3iv | 3.2772 |
C7···H3 | 3.2695 | H9···H12Cvii | 3.5166 |
C8···H3 | 3.2596 | H10A···O3vi | 2.5210 |
C8···H5 | 3.2841 | H10A···N1vi | 3.1491 |
C9···H1 | 3.1828 | H10A···N2vi | 3.1687 |
C9···H2 | 3.2541 | H10A···C6iii | 3.5086 |
C9···H4 | 3.2311 | H10A···C7iii | 3.0639 |
C10···H1 | 2.5777 | H10A···C11vi | 2.7721 |
C10···H7 | 2.3883 | H10A···H4iii | 3.2117 |
C11···H8 | 2.6427 | H10A···H5iii | 2.3551 |
C11···H9 | 2.6799 | H10A···H13Aviii | 3.3663 |
C12···H7 | 2.4955 | H10A···H14Bviii | 3.3514 |
C13···H9 | 3.2749 | H10A···H15Cvii | 3.5062 |
C13···H10A | 2.8471 | H11B···O5vii | 3.5301 |
C13···H11B | 2.7500 | H11B···O6vii | 3.2335 |
C14···H10A | 2.7151 | H11B···C14vii | 3.4286 |
C14···H11B | 2.5313 | H11B···C15vii | 2.9753 |
C14···H12C | 3.1860 | H11B···C16vii | 2.8478 |
C14···H14B | 3.1008 | H11B···C17vii | 3.2523 |
C15···H8 | 3.2665 | H11B···C19vii | 3.0282 |
C15···H9 | 3.2713 | H11B···H5iii | 3.2546 |
C15···H13A | 3.1908 | H11B···H14Bvii | 2.7101 |
C15···H14B | 2.5665 | H11B···H15Cvii | 2.6154 |
C15···H15C | 2.6025 | H11B···H17Bvii | 3.5313 |
C16···H14B | 3.4580 | H12C···O3vi | 3.2371 |
C16···H15C | 2.9045 | H12C···O4viii | 2.6180 |
C16···H16A | 3.1935 | H12C···O5viii | 3.1429 |
C16···H17B | 2.6111 | H12C···C11vi | 3.3916 |
C16···H18C | 2.6155 | H12C···C16vii | 3.5908 |
C17···H7 | 2.5638 | H12C···C17vii | 3.4633 |
C17···H8 | 3.2767 | H12C···C18viii | 3.1347 |
C17···H17B | 2.7416 | H12C···C19viii | 3.0436 |
C17···H18C | 2.7583 | H12C···H9vii | 3.5166 |
C18···H8 | 2.6086 | H12C···H12Cviii | 2.7091 |
C20···H9 | 2.5292 | H12C···H13Aviii | 2.9594 |
H1···H6 | 3.5152 | H12C···H14Bviii | 2.6299 |
H2···H3 | 2.3168 | H12C···H17Bvii | 3.3110 |
H3···H4 | 2.3338 | H13A···O3vii | 3.1758 |
H4···H5 | 2.3358 | H13A···C6xii | 3.0406 |
H6···H7 | 2.1478 | H13A···C18viii | 3.5765 |
H7···H9 | 2.1713 | H13A···C20ix | 3.3118 |
H8···H10A | 2.3516 | H13A···H4xii | 2.0967 |
H8···H11B | 2.4712 | H13A···H10Aviii | 3.3663 |
H8···H12C | 3.5828 | H13A···H12Cviii | 2.9594 |
H9···H16A | 3.4997 | H13A···H16Aix | 2.8195 |
H9···H17B | 2.2971 | H13A···H17Bvi | 2.9562 |
H9···H18C | 2.3277 | H13A···H18Cix | 2.9032 |
O1···H1i | 2.6152 | H14B···O3vii | 2.7891 |
O1···H8iii | 3.5409 | H14B···C11vii | 3.3148 |
O2···H2iv | 3.1647 | H14B···C12vii | 3.1794 |
O2···H3vi | 3.2680 | H14B···C13vii | 2.7634 |
O2···H6v | 2.5946 | H14B···C14vii | 3.5351 |
O2···H7v | 2.1022 | H14B···C18viii | 3.4123 |
O2···H9v | 3.1049 | H14B···C18vii | 3.5508 |
O2···H18Cv | 3.4209 | H14B···H4xii | 3.4738 |
O3···H1vi | 3.5039 | H14B···H8vii | 2.4905 |
O3···H1iii | 3.0140 | H14B···H10Aviii | 3.3514 |
O3···H4i | 3.5084 | H14B···H11Bvii | 2.7101 |
O3···H5i | 3.1009 | H14B···H12Cviii | 2.6299 |
O3···H10Aii | 2.5210 | H15C···C6xiv | 3.4441 |
O3···H12Cii | 3.2371 | H15C···C7xiv | 3.0743 |
O3···H13Avii | 3.1758 | H15C···C9xiv | 3.1835 |
O3···H14Bvii | 2.7891 | H15C···C18vii | 3.4644 |
O4···H9vi | 3.0390 | H15C···C20ix | 3.3767 |
O4···H12Cviii | 2.6180 | H15C···H4xii | 3.5609 |
O5···H3v | 3.1552 | H15C···H5xiv | 3.2923 |
O5···H9vi | 3.4102 | H15C···H8vii | 3.2100 |
O5···H11Bvii | 3.5301 | H15C···H10Avii | 3.5062 |
O5···H12Cviii | 3.1429 | H15C···H11Bvii | 2.6154 |
O5···H16Aix | 2.5300 | H15C···H16Aix | 2.8571 |
O5···H17Bvi | 2.4880 | H15C···H18Cix | 3.1098 |
O5···H18Cix | 3.5978 | H16A···O5ix | 2.5300 |
O6···H2v | 3.4165 | H16A···O6ix | 2.7939 |
O6···H3v | 3.5440 | H16A···C5xiv | 3.4640 |
O6···H11Bvii | 3.2335 | H16A···C15ix | 3.4488 |
O6···H16Aix | 2.7939 | H16A···C16ix | 3.5794 |
N1···H5vi | 3.5731 | H16A···C19ix | 2.9135 |
N1···H5i | 3.4325 | H16A···C20xiii | 3.2931 |
N1···H8ii | 3.2075 | H16A···H3xiv | 3.1271 |
N1···H10Aii | 3.1491 | H16A···H4xiv | 3.5157 |
N2···H10Aii | 3.1687 | H16A···H13Aix | 2.8195 |
C1···H1i | 3.4562 | H16A···H15Cix | 2.8571 |
C1···H4vi | 3.4026 | H16A···H16Axiii | 3.0153 |
C1···H8ii | 3.3969 | H16A···H17Bxiii | 2.8319 |
C2···H4vi | 3.2626 | H16A···H18Cxiii | 3.5396 |
C3···H2iv | 3.4444 | H17B···O5ii | 2.4880 |
C3···H3vi | 3.5809 | H17B···C19ii | 3.2570 |
C3···H4vi | 3.5766 | H17B···C20xiii | 3.5118 |
C3···H7v | 3.3006 | H17B···H3iv | 3.1628 |
C3···H18Cv | 3.4000 | H17B···H4xiv | 3.3622 |
C4···H6ii | 3.3930 | H17B···H11Bvii | 3.5313 |
C4···H6iv | 3.5039 | H17B···H12Cvii | 3.3110 |
C4···H18Cv | 3.1614 | H17B···H13Aii | 2.9562 |
C5···H6ii | 3.3690 | H17B···H16Axiii | 2.8319 |
C5···H16Ax | 3.4640 | H17B···H17Bxiii | 3.4741 |
C5···H18Civ | 3.5979 | H18C···O2v | 3.4209 |
C6···H10Aiii | 3.5086 | H18C···O5ix | 3.5978 |
C6···H13Axi | 3.0406 | H18C···C3v | 3.4000 |
C6···H15Cx | 3.4441 | H18C···C4v | 3.1614 |
C7···H1i | 3.4734 | H18C···C5iv | 3.5979 |
C7···H8iii | 3.5908 | H18C···C8v | 3.2174 |
C7···H10Aiii | 3.0639 | H18C···C19ix | 3.3301 |
C7···H15Cx | 3.0743 | H18C···H2v | 3.2006 |
C8···H7ii | 3.5060 | H18C···H3iv | 2.8620 |
C8···H18Cv | 3.2174 | H18C···H4iv | 3.2072 |
C9···H1i | 3.4959 | H18C···H13Aix | 2.9032 |
C9···H15Cx | 3.1835 | H18C···H15Cix | 3.1098 |
C10···H2iv | 3.4588 | H18C···H16Axiii | 3.5396 |
C10···H6v | 3.5073 | ||
C1—O1—C9 | 118.5 (4) | C15—C16—C17 | 119.5 (4) |
C14—O4—C18 | 117.6 (4) | C12—C17—C16 | 120.0 (4) |
C15—O5—C19 | 113.4 (3) | N1—N2—H7 | 119.645 |
C16—O6—C20 | 116.6 (4) | C11—N2—H7 | 119.637 |
N2—N1—C10 | 115.0 (3) | O1—C1—H1 | 117.355 |
N1—N2—C11 | 120.7 (3) | C2—C1—H1 | 117.346 |
O1—C1—C2 | 125.3 (4) | C5—C4—H2 | 119.811 |
C1—C2—C3 | 119.3 (4) | C8—C4—H2 | 119.804 |
C1—C2—C10 | 121.3 (4) | C4—C5—H3 | 120.079 |
C3—C2—C10 | 119.4 (4) | C6—C5—H3 | 120.082 |
O2—C3—C2 | 122.3 (4) | C5—C6—H4 | 119.339 |
O2—C3—C8 | 122.5 (4) | C7—C6—H4 | 119.343 |
C2—C3—C8 | 115.3 (4) | C6—C7—H5 | 121.057 |
C5—C4—C8 | 120.4 (5) | C9—C7—H5 | 121.046 |
C4—C5—C6 | 119.8 (6) | N1—C10—H6 | 119.366 |
C5—C6—C7 | 121.3 (5) | C2—C10—H6 | 119.364 |
C6—C7—C9 | 117.9 (6) | C12—C13—H8 | 120.275 |
C3—C8—C4 | 122.0 (4) | C14—C13—H8 | 120.278 |
C3—C8—C9 | 119.5 (4) | C12—C17—H9 | 119.980 |
C4—C8—C9 | 118.5 (4) | C16—C17—H9 | 119.986 |
O1—C9—C7 | 116.1 (5) | O4—C18—H10A | 109.468 |
O1—C9—C8 | 121.9 (4) | O4—C18—H11B | 109.472 |
C7—C9—C8 | 122.0 (5) | O4—C18—H12C | 109.474 |
N1—C10—C2 | 121.3 (4) | H10A—C18—H11B | 109.465 |
O3—C11—N2 | 123.6 (4) | H10A—C18—H12C | 109.472 |
O3—C11—C12 | 122.4 (4) | H11B—C18—H12C | 109.476 |
N2—C11—C12 | 114.0 (4) | O5—C19—H13A | 109.472 |
C11—C12—C13 | 118.8 (4) | O5—C19—H14B | 109.472 |
C11—C12—C17 | 121.0 (4) | O5—C19—H15C | 109.473 |
C13—C12—C17 | 120.1 (4) | H13A—C19—H14B | 109.470 |
C12—C13—C14 | 119.4 (4) | H13A—C19—H15C | 109.473 |
O4—C14—C13 | 124.6 (4) | H14B—C19—H15C | 109.467 |
O4—C14—C15 | 114.8 (4) | O6—C20—H16A | 109.471 |
C13—C14—C15 | 120.6 (4) | O6—C20—H17B | 109.473 |
O5—C15—C14 | 119.8 (4) | O6—C20—H18C | 109.471 |
O5—C15—C16 | 120.0 (4) | H16A—C20—H17B | 109.473 |
C14—C15—C16 | 120.2 (4) | H16A—C20—H18C | 109.472 |
O6—C16—C15 | 114.9 (4) | H17B—C20—H18C | 109.467 |
O6—C16—C17 | 125.6 (4) | ||
C1—O1—C9—C7 | −178.5 (3) | H2—C4—C5—H3 | 2.5 |
C1—O1—C9—C8 | 1.5 (5) | H2—C4—C8—C3 | −3.3 |
C9—O1—C1—C2 | −1.1 (6) | H2—C4—C8—C9 | 177.5 |
C9—O1—C1—H1 | 178.9 | C4—C5—C6—C7 | −0.3 (7) |
C14—O4—C18—H10A | 74.4 | C4—C5—C6—H4 | 179.7 |
C14—O4—C18—H11B | −45.6 | H3—C5—C6—C7 | 179.7 |
C14—O4—C18—H12C | −165.6 | H3—C5—C6—H4 | −0.3 |
C18—O4—C14—C13 | −22.6 (5) | C5—C6—C7—C9 | −1.7 (7) |
C18—O4—C14—C15 | 157.7 (3) | C5—C6—C7—H5 | 178.3 |
C15—O5—C19—H13A | 177.4 | H4—C6—C7—C9 | 178.3 |
C15—O5—C19—H14B | 57.4 | H4—C6—C7—H5 | −1.7 |
C15—O5—C19—H15C | −62.6 | C6—C7—C9—O1 | −178.3 (4) |
C19—O5—C15—C14 | −99.4 (4) | C6—C7—C9—C8 | 1.6 (6) |
C19—O5—C15—C16 | 80.8 (4) | H5—C7—C9—O1 | 1.7 |
C16—O6—C20—H16A | 179.7 | H5—C7—C9—C8 | −178.4 |
C16—O6—C20—H17B | 59.7 | C3—C8—C9—O1 | 1.2 (5) |
C16—O6—C20—H18C | −60.3 | C3—C8—C9—C7 | −178.8 (3) |
C20—O6—C16—C15 | 180.0 (3) | C4—C8—C9—O1 | −179.6 (3) |
C20—O6—C16—C17 | −0.7 (4) | C4—C8—C9—C7 | 0.4 (6) |
N2—N1—C10—C2 | −176.9 (3) | O3—C11—C12—C13 | 28.2 (5) |
N2—N1—C10—H6 | 3.1 | O3—C11—C12—C17 | −149.3 (3) |
C10—N1—N2—C11 | −179.5 (3) | N2—C11—C12—C13 | −152.5 (3) |
C10—N1—N2—H7 | 0.5 | N2—C11—C12—C17 | 30.0 (4) |
N1—N2—C11—O3 | 12.6 (5) | C11—C12—C13—C14 | −178.2 (3) |
N1—N2—C11—C12 | −166.8 (3) | C11—C12—C13—H8 | 1.8 |
H7—N2—C11—O3 | −167.4 | C11—C12—C17—C16 | −180.0 (3) |
H7—N2—C11—C12 | 13.2 | C11—C12—C17—H9 | 0.0 |
O1—C1—C2—C3 | −2.1 (6) | C13—C12—C17—C16 | 2.6 (4) |
O1—C1—C2—C10 | 178.3 (3) | C13—C12—C17—H9 | −177.4 |
H1—C1—C2—C3 | 177.9 | C17—C12—C13—C14 | −0.7 (4) |
H1—C1—C2—C10 | −1.7 | C17—C12—C13—H8 | 179.3 |
C1—C2—C3—O2 | −174.5 (3) | C12—C13—C14—O4 | 177.6 (3) |
C1—C2—C3—C8 | 4.5 (5) | C12—C13—C14—C15 | −2.7 (5) |
C1—C2—C10—N1 | 1.0 (5) | H8—C13—C14—O4 | −2.4 |
C1—C2—C10—H6 | −179.0 | H8—C13—C14—C15 | 177.3 |
C3—C2—C10—N1 | −178.6 (3) | O4—C14—C15—O5 | 4.2 (4) |
C3—C2—C10—H6 | 1.4 | O4—C14—C15—C16 | −176.0 (3) |
C10—C2—C3—O2 | 5.1 (5) | C13—C14—C15—O5 | −175.5 (3) |
C10—C2—C3—C8 | −175.9 (3) | C13—C14—C15—C16 | 4.2 (5) |
O2—C3—C8—C4 | −4.2 (5) | O5—C15—C16—O6 | −3.2 (4) |
O2—C3—C8—C9 | 175.0 (3) | O5—C15—C16—C17 | 177.4 (3) |
C2—C3—C8—C4 | 176.7 (3) | C14—C15—C16—O6 | 177.0 (3) |
C2—C3—C8—C9 | −4.1 (5) | C14—C15—C16—C17 | −2.3 (5) |
C5—C4—C8—C3 | 176.7 (4) | O6—C16—C17—C12 | 179.7 (3) |
C5—C4—C8—C9 | −2.5 (6) | O6—C16—C17—H9 | −0.3 |
C8—C4—C5—C6 | 2.4 (7) | C15—C16—C17—C12 | −1.0 (4) |
C8—C4—C5—H3 | −177.6 | C15—C16—C17—H9 | 179.0 |
H2—C4—C5—C6 | −177.6 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+1, −y+1, −z+1; (iv) −x+2, −y, −z+1; (v) −x+1, −y, −z+1; (vi) x−1, y, z; (vii) −x, −y+1, −z+2; (viii) −x−1, −y+1, −z+2; (ix) −x, −y, −z+2; (x) x+1, y, z−1; (xi) x+2, y, z−1; (xii) x−2, y, z+1; (xiii) −x+1, −y, −z+2; (xiv) x−1, y, z+1. |
Cg is the centroid of the C12–C17 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H7···O2v | 0.88 | 2.10 | 2.942 (6) | 159 |
C4—H2···Cgv | 0.95 | 2.97 | 3.716 (8) | 136 |
Symmetry code: (v) −x+1, −y, −z+1. |
Cg is the centroid of the C12–C17 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H7···O2i | 0.880 | 2.102 | 2.942 (6) | 159.3 |
C4—H2···Cgi | 0.95 | 2.97 | 3.716 (8) | 136 |
Symmetry code: (i) −x+1, −y, −z+1. |
Acknowledgements
We acknowledge University of Shizuoka for instrumental support.
References
Ishikawa, Y. & Motohashi, Y. (2013a). Acta Cryst. E69, o1225. CSD CrossRef IUCr Journals Google Scholar
Ishikawa, Y. & Motohashi, Y. (2013b). Acta Cryst. E69, o1226. CSD CrossRef IUCr Journals Google Scholar
Ishikawa, Y. & Motohashi, Y. (2013c). Acta Cryst. E69, o1448. CSD CrossRef IUCr Journals Google Scholar
Khan, K. M., Ambreen, N., Hussain, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 2983–2988. Web of Science CrossRef PubMed CAS Google Scholar
Qin, D. D., Qi, G. F., Yang, Z. Y., Wu, J. C. & Liu, Y. C. (2009). J. Fluoresc. 19, 409–418. Web of Science CSD CrossRef PubMed CAS Google Scholar
Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tu, Q. D., Li, D., Sun, Y., Han, X. Y., Yi, F., Sha, Y., Ren, Y. L., Ding, M. W., Feng, L. L. & Wan, J. (2013). Bioorg. Med. Chem. 21, 2826–2831. Web of Science CrossRef CAS PubMed Google Scholar
Wang, B. D., Yang, Z. Y., Crewdson, P. & Wang, D. Q. (2007). J. Inorg. Biochem. 101, 1492–1504. Web of Science CSD CrossRef PubMed CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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 3-formylchromone with 3,4,5-trimethoxybenzoylhydrazide in benzene in good yield. The structure (Figure 1) shows that the atoms of the E-3-(hydrazonomethyl)-4H-chromen-4-one segment are essentially coplanar [the largest deviation = 0.065 (6) Å for C4]. The dihedral angle between this segment and the benzene ring of the trimethoxybenzene unit is 40.18 (10) Å. The carbonyl (C11–O3) group is slightly twisted with respect to this segment [N1–N2–C11–O3 = 12.6 (5)°]. In the crystal, the molecule is linked to its inverse-symmetry equivalent (i: –x + 1, –y, –z + 1) by N–H···O hydrogen bonds, and by C–H···π interaction between the benzene ring of the trimethoxybenzene unit and the C4–H2 atom of the chromone segment [centroid···C4 distance = 3.716 (8) Å]. In addition, the –CH=N–NH– segment is stacked on the benzene ring of the chromone unit of a translation-related equivalent molecule (ii: x + 1, y, z) [centroid–centroid distance = 3.413 (6) Å]. Figure 2 illustrates these intermolecular interactions.