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COMMUNICATIONS
ISSN: 2056-9890

(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

(Received 7 March 2014; accepted 13 March 2014; online 26 March 2014)

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].

Related literature

For the biological activity of related compounds, see: Khan et al. (2009[Khan, K. M., Ambreen, N., Hussain, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 2983-2988.]); Tu et al. (2013[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.]). For related structures, see: Wang et al. (2007[Wang, B. D., Yang, Z. Y., Crewdson, P. & Wang, D. Q. (2007). J. Inorg. Biochem. 101, 1492-1504.]); Qin et al. (2009[Qin, D. D., Qi, G. F., Yang, Z. Y., Wu, J. C. & Liu, Y. C. (2009). J. Fluoresc. 19, 409-418.]); Ishikawa et al. (2013a[Ishikawa, Y. & Motohashi, Y. (2013a). Acta Cryst. E69, o1225.],b[Ishikawa, Y. & Motohashi, Y. (2013b). Acta Cryst. E69, o1226.],c[Ishikawa, Y. & Motohashi, Y. (2013c). Acta Cryst. E69, o1448.]).

[Scheme 1]

Experimental

Crystal data
  • C20H18N2O6

  • Mr = 382.37

  • Triclinic, [P \overline 1]

  • a = 6.628 (7) Å

  • b = 11.029 (18) Å

  • c = 12.544 (18) Å

  • α = 105.34 (12)°

  • β = 96.94 (10)°

  • γ = 95.88 (10)°

  • V = 869 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 100 K

  • 0.40 × 0.18 × 0.12 mm

Data collection
  • Rigaku AFC-7R diffractometer

  • 4902 measured reflections

  • 3982 independent reflections

  • 1962 reflections with F2 > 2σ(F2)

  • Rint = 0.040

  • 3 standard reflections every 150 reflections intensity decay: 1.9%

Refinement
  • R[F2 > 2σ(F2)] = 0.068

  • wR(F2) = 0.208

  • S = 1.01

  • 3982 reflections

  • 256 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.34 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C12–C17 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H7⋯O2i 0.88 2.10 2.942 (6) 159
C4—H2⋯Cgi 0.95 2.97 3.716 (8) 136
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: WinAFC (Rigaku, 1999[Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.]); cell refinement: WinAFC; data reduction: WinAFC; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); software used to prepare material for publication: CrystalStructure.

Supporting information


Comment top

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.

Related literature top

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 top

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.

Refinement top

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)].

Computing details top

Data collection: WinAFC (Rigaku, 1999); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are shown as small spheres of arbitrary radius.
[Figure 2] Fig. 2. A crystal packing view of the title compound. Intermolecular N–H···O hydrogen bonds are represented by dashed lines.
(E)-3,4,5-Trimethoxy-N'-[(4-oxo-4H-chromen-3-yl)methylidene]benzohydrazide top
Crystal data top
C20H18N2O6Z = 2
Mr = 382.37F(000) = 400.00
Triclinic, P1Dx = 1.461 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 6.628 (7) ÅCell parameters from 25 reflections
b = 11.029 (18) Åθ = 15.1–17.5°
c = 12.544 (18) ŵ = 0.11 mm1
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
Data collection top
Rigaku AFC-7R
diffractometer
θmax = 27.5°
ω–2θ scansh = 84
4902 measured reflectionsk = 1414
3982 independent reflectionsl = 1616
1962 reflections with F2 > 2σ(F2)3 standard reflections every 150 reflections
Rint = 0.040 intensity decay: 1.9%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.208H-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 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.34 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C20H18N2O6γ = 95.88 (10)°
Mr = 382.37V = 869 (2) Å3
Triclinic, P1Z = 2
a = 6.628 (7) ÅMo Kα radiation
b = 11.029 (18) ŵ = 0.11 mm1
c = 12.544 (18) ÅT = 100 K
α = 105.34 (12)°0.40 × 0.18 × 0.12 mm
β = 96.94 (10)°
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.040
4902 measured reflections3 standard reflections every 150 reflections
3982 independent reflections intensity decay: 1.9%
1962 reflections with F2 > 2σ(F2)
Refinement top
R[F2 > 2σ(F2)] = 0.0680 restraints
wR(F2) = 0.208H-atom parameters constrained
S = 1.01Δρmax = 0.30 e Å3
3982 reflectionsΔρmin = 0.34 e Å3
256 parameters
Special details top

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).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O11.0097 (4)0.3621 (3)0.4260 (3)0.0470 (8)
O20.7771 (4)0.0019 (3)0.4167 (3)0.0416 (8)
O30.2618 (4)0.4738 (3)0.6820 (2)0.0369 (7)
O40.3434 (4)0.4096 (3)0.8991 (3)0.0413 (7)
O50.2570 (4)0.2233 (3)0.9857 (2)0.0357 (7)
O60.0813 (4)0.1163 (3)0.9562 (2)0.0359 (7)
N10.5082 (5)0.3018 (3)0.5846 (3)0.0267 (7)
N20.3513 (5)0.2739 (3)0.6410 (3)0.0266 (7)
C10.8476 (6)0.3386 (4)0.4747 (4)0.0375 (10)
C20.7663 (5)0.2226 (3)0.4787 (3)0.0257 (8)
C30.8540 (6)0.1112 (4)0.4232 (3)0.0298 (9)
C41.1452 (7)0.0413 (5)0.3228 (4)0.0539 (13)
C51.3098 (8)0.0687 (7)0.2729 (4)0.0764 (19)
C61.3754 (7)0.1940 (7)0.2766 (4)0.077 (2)
C71.2771 (7)0.2920 (6)0.3295 (4)0.0602 (15)
C81.0377 (6)0.1377 (4)0.3740 (3)0.0350 (10)
C91.1067 (6)0.2617 (5)0.3765 (3)0.0402 (10)
C100.5918 (6)0.2068 (3)0.5368 (3)0.0267 (8)
C110.2483 (6)0.3672 (4)0.6948 (3)0.0267 (8)
C120.1178 (6)0.3282 (3)0.7727 (3)0.0264 (8)
C130.0553 (6)0.3875 (4)0.7941 (3)0.0297 (8)
C140.1749 (5)0.3547 (4)0.8687 (3)0.0305 (9)
C150.1287 (6)0.2606 (4)0.9181 (3)0.0292 (8)
C160.0466 (6)0.2031 (4)0.8991 (3)0.0277 (8)
C170.1710 (5)0.2381 (3)0.8267 (3)0.0254 (8)
C180.3580 (6)0.5322 (4)0.8866 (4)0.0409 (10)
C190.1850 (7)0.2802 (5)1.1040 (4)0.0505 (12)
C200.2601 (6)0.0549 (4)0.9390 (4)0.0399 (10)
H10.78420.40900.50950.0450*
H21.10380.04380.32280.0647*
H31.37910.00240.23570.0916*
H41.49020.21230.24200.0920*
H51.32460.37760.33360.0723*
H60.53940.12420.53920.0321*
H70.31720.19510.64230.0319*
H80.09100.44960.75800.0357*
H90.29190.20040.81440.0304*
H10A0.39520.52620.80710.0491*
H11B0.22550.58630.91580.0491*
H12C0.46360.56920.92810.0491*
H13A0.28560.25321.14730.0606*
H14B0.16760.37291.12010.0606*
H15C0.05320.25301.12450.0606*
H16A0.26990.00480.98430.0479*
H17B0.38280.11890.96110.0479*
H18C0.24990.00880.85970.0479*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0324 (16)0.0546 (18)0.068 (2)0.0022 (14)0.0109 (15)0.0423 (16)
O20.0325 (15)0.0253 (14)0.0578 (18)0.0070 (11)0.0195 (13)0.0058 (13)
O30.0488 (17)0.0308 (15)0.0379 (16)0.0129 (12)0.0143 (13)0.0152 (12)
O40.0326 (16)0.0417 (16)0.0572 (19)0.0097 (13)0.0201 (14)0.0194 (14)
O50.0236 (14)0.0435 (16)0.0409 (16)0.0044 (12)0.0095 (12)0.0147 (13)
O60.0299 (14)0.0417 (15)0.0433 (16)0.0056 (12)0.0098 (12)0.0221 (13)
N10.0302 (17)0.0241 (15)0.0243 (16)0.0015 (13)0.0062 (13)0.0053 (13)
N20.0323 (17)0.0190 (14)0.0276 (16)0.0003 (12)0.0092 (13)0.0042 (12)
C10.032 (3)0.036 (2)0.048 (3)0.0045 (17)0.0081 (18)0.0208 (19)
C20.0240 (18)0.0249 (18)0.0260 (19)0.0043 (14)0.0037 (15)0.0065 (15)
C30.0259 (19)0.032 (2)0.0251 (19)0.0047 (16)0.0067 (15)0.0006 (15)
C40.031 (3)0.072 (3)0.041 (3)0.004 (2)0.0101 (19)0.015 (3)
C50.033 (3)0.135 (6)0.036 (3)0.010 (3)0.011 (2)0.013 (3)
C60.024 (3)0.171 (7)0.034 (3)0.012 (4)0.009 (2)0.034 (4)
C70.023 (3)0.123 (5)0.045 (3)0.007 (3)0.001 (2)0.051 (3)
C80.0203 (18)0.055 (3)0.0217 (19)0.0055 (17)0.0030 (15)0.0023 (18)
C90.0204 (19)0.075 (3)0.031 (2)0.0067 (19)0.0033 (16)0.031 (2)
C100.0296 (19)0.0195 (17)0.0302 (19)0.0051 (14)0.0062 (15)0.0078 (15)
C110.032 (2)0.0265 (18)0.0203 (17)0.0056 (15)0.0046 (15)0.0026 (14)
C120.0280 (19)0.0243 (18)0.0238 (18)0.0009 (15)0.0049 (15)0.0031 (15)
C130.0258 (19)0.0290 (19)0.035 (2)0.0061 (15)0.0045 (16)0.0095 (16)
C140.0208 (19)0.0310 (19)0.035 (2)0.0027 (15)0.0042 (16)0.0013 (16)
C150.0244 (19)0.0296 (19)0.029 (2)0.0046 (15)0.0051 (15)0.0033 (16)
C160.0220 (18)0.0296 (19)0.0296 (19)0.0007 (15)0.0029 (15)0.0073 (15)
C170.0193 (17)0.0288 (18)0.0266 (18)0.0010 (14)0.0038 (14)0.0061 (15)
C180.036 (3)0.040 (3)0.050 (3)0.0058 (18)0.0121 (19)0.0155 (19)
C190.045 (3)0.061 (3)0.046 (3)0.004 (2)0.022 (2)0.013 (3)
C200.025 (2)0.048 (3)0.056 (3)0.0045 (18)0.0079 (18)0.031 (2)
Geometric parameters (Å, º) top
O1—C11.335 (6)C12—C131.397 (6)
O1—C91.380 (6)C12—C171.394 (6)
O2—C31.237 (5)C13—C141.390 (6)
O3—C111.224 (5)C14—C151.384 (6)
O4—C141.371 (5)C15—C161.396 (6)
O4—C181.414 (6)C16—C171.398 (6)
O5—C151.378 (5)N2—H70.880
O5—C191.448 (6)C1—H10.950
O6—C161.360 (6)C4—H20.950
O6—C201.434 (5)C5—H30.950
N1—N21.380 (5)C6—H40.950
N1—C101.278 (5)C7—H50.950
N2—C111.367 (5)C10—H60.950
C1—C21.352 (6)C13—H80.950
C2—C31.457 (6)C17—H90.950
C2—C101.459 (6)C18—H10A0.980
C3—C81.468 (6)C18—H11B0.980
C4—C51.368 (8)C18—H12C0.980
C4—C81.399 (7)C19—H13A0.980
C5—C61.392 (11)C19—H14B0.980
C6—C71.380 (9)C19—H15C0.980
C7—C91.387 (7)C20—H16A0.980
C8—C91.387 (7)C20—H17B0.980
C11—C121.496 (6)C20—H18C0.980
O1···C32.843 (7)C10···H8ii3.5772
O2···C13.559 (8)C11···H10Aii2.7721
O2···C42.877 (6)C11···H12Cii3.3916
O2···C102.845 (6)C11···H14Bvii3.3148
O3···N12.765 (6)C12···H2v3.1739
O3···C132.883 (6)C12···H14Bvii3.1794
O3···C173.586 (7)C13···H14Bvii2.7634
O4···O52.646 (6)C14···H11Bvii3.4286
O4···C193.367 (8)C14···H14Bvii3.5351
O5···O62.659 (5)C15···H2v3.3544
O6···C193.081 (7)C15···H3v3.1886
N1···C12.825 (6)C15···H11Bvii2.9753
N2···C172.842 (6)C15···H16Aix3.4488
C1···C73.570 (8)C16···H2v2.8659
C1···C82.751 (7)C16···H3v3.3864
C2···C92.777 (6)C16···H11Bvii2.8478
C4···C72.790 (10)C16···H12Cvii3.5908
C5···C92.753 (9)C16···H16Aix3.5794
C6···C82.769 (7)C17···H2v2.7705
C10···C113.507 (7)C17···H11Bvii3.2523
C12···C152.782 (7)C17···H12Cvii3.4633
C13···C162.795 (7)C18···H5iii3.1966
C13···C182.856 (7)C18···H12Cviii3.1347
C14···C172.780 (6)C18···H13Aviii3.5765
C14···C193.272 (8)C18···H14Bviii3.4123
C15···C183.586 (8)C18···H14Bvii3.5508
C16···C193.122 (7)C18···H15Cvii3.4644
C17···C202.821 (7)C19···H4xii3.0738
O1···O1i3.141 (7)C19···H8vii3.2579
O1···O3ii3.289 (7)C19···H11Bvii3.0282
O1···O3iii3.119 (6)C19···H12Cviii3.0436
O1···C1i3.201 (8)C19···H16Aix2.9135
O1···C11ii3.531 (7)C19···H17Bvi3.2570
O2···O2iv3.417 (6)C19···H18Cix3.3301
O2···N2v2.942 (6)C20···H3iv3.4296
O2···C3iv3.511 (6)C20···H13Aix3.3118
O2···C4iv3.411 (8)C20···H15Cix3.3767
O2···C8iv3.539 (7)C20···H16Axiii3.2931
O2···C10v3.394 (6)C20···H17Bxiii3.5118
O2···C17v3.552 (7)H1···O1i2.6152
O3···O1vi3.289 (7)H1···O3ii3.5039
O3···O1iii3.119 (6)H1···O3iii3.0140
O3···C1vi3.451 (7)H1···C1i3.4562
O3···C1iii3.285 (7)H1···C7i3.4734
O3···C18ii3.252 (7)H1···C9i3.4959
O3···C19vii3.404 (8)H1···H1i3.3925
O4···N2vi3.472 (7)H1···H5vi3.4678
O4···C11vi3.397 (6)H1···H5i2.8587
O4···C17vi3.449 (6)H1···H8ii3.0273
O4···C18viii3.491 (7)H2···O2iv3.1647
O5···C20vi3.433 (6)H2···O6v3.4165
O5···C20ix3.440 (8)H2···C3iv3.4444
O6···O6ix3.188 (6)H2···C10iv3.4588
O6···C4v3.536 (8)H2···C12v3.1739
O6···C20ix3.402 (7)H2···C15v3.3544
N1···C7vi3.346 (8)H2···C16v2.8659
N1···C9vi3.400 (7)H2···C17v2.7705
N1···C13ii3.530 (7)H2···H6iv3.1034
N2···O2v2.942 (6)H2···H7v3.2391
N2···O4ii3.472 (7)H2···H9v3.0382
N2···C8vi3.579 (7)H2···H18Cv3.2006
N2···C9vi3.475 (7)H3···O2ii3.2680
C1···O1i3.201 (8)H3···O5v3.1552
C1···O3ii3.451 (7)H3···O6v3.5440
C1···O3iii3.285 (7)H3···C3ii3.5809
C1···C11ii3.517 (7)H3···C15v3.1886
C2···C6vi3.326 (7)H3···C16v3.3864
C3···O2iv3.511 (6)H3···C20iv3.4296
C4···O2iv3.411 (8)H3···H6iv3.4770
C4···O6v3.536 (8)H3···H9iv3.2772
C4···C16v3.332 (8)H3···H16Ax3.1271
C4···C17v3.475 (8)H3···H17Biv3.1628
C5···C10ii3.468 (8)H3···H18Civ2.8620
C6···C2ii3.326 (7)H4···O3i3.5084
C6···C10ii3.364 (8)H4···C1ii3.4026
C7···N1ii3.346 (8)H4···C2ii3.2626
C7···C10ii3.519 (8)H4···C3ii3.5766
C8···O2iv3.539 (7)H4···C19xi3.0738
C8···N2ii3.579 (7)H4···H10Aiii3.2117
C9···N1ii3.400 (7)H4···H13Axi2.0967
C9···N2ii3.475 (7)H4···H14Bxi3.4738
C10···O2v3.394 (6)H4···H15Cxi3.5609
C10···C5vi3.468 (8)H4···H16Ax3.5157
C10···C6vi3.364 (8)H4···H17Bx3.3622
C10···C7vi3.519 (8)H4···H18Civ3.2072
C11···O1vi3.531 (7)H5···O3i3.1009
C11···O4ii3.397 (6)H5···N1ii3.5731
C11···C1vi3.517 (7)H5···N1i3.4325
C11···C18ii3.332 (7)H5···C18iii3.1966
C13···N1vi3.530 (7)H5···H1ii3.4678
C16···C4v3.332 (8)H5···H1i2.8587
C17···O2v3.552 (7)H5···H8iii2.9465
C17···O4ii3.449 (6)H5···H10Aiii2.3551
C17···C4v3.475 (8)H5···H11Biii3.2546
C18···O3vi3.252 (7)H5···H15Cx3.2923
C18···O4viii3.491 (7)H6···O2v2.5946
C18···C11vi3.332 (7)H6···C4vi3.3930
C19···O3vii3.404 (8)H6···C4iv3.5039
C19···C20ix3.565 (9)H6···C5vi3.3690
C20···O5ii3.433 (6)H6···C10v3.5073
C20···O5ix3.440 (8)H6···H2iv3.1034
C20···O6ix3.402 (7)H6···H3iv3.4770
C20···C19ix3.565 (9)H6···H6v2.6279
O1···H52.5194H7···O2v2.1022
O2···H22.6183H7···C3v3.3006
O2···H62.5661H7···C8vi3.5060
O3···H73.0489H7···H2v3.2391
O3···H82.6446H8···O1iii3.5409
O4···H82.6652H8···N1vi3.2075
O4···H14B3.0194H8···C1vi3.3969
O6···H92.6793H8···C7iii3.5908
O6···H15C2.5638H8···C10vi3.5772
N1···H12.4883H8···C19vii3.2579
N2···H62.3661H8···H1vi3.0273
N2···H92.5728H8···H5iii2.9465
C1···H63.2916H8···H14Bvii2.4905
C3···H13.2753H8···H15Cvii3.2100
C3···H22.6819H9···O2v3.1049
C3···H62.6773H9···O4ii3.0390
C4···H43.2406H9···O5ii3.4102
C5···H53.2771H9···H2v3.0382
C6···H23.2470H9···H3iv3.2772
C7···H33.2695H9···H12Cvii3.5166
C8···H33.2596H10A···O3vi2.5210
C8···H53.2841H10A···N1vi3.1491
C9···H13.1828H10A···N2vi3.1687
C9···H23.2541H10A···C6iii3.5086
C9···H43.2311H10A···C7iii3.0639
C10···H12.5777H10A···C11vi2.7721
C10···H72.3883H10A···H4iii3.2117
C11···H82.6427H10A···H5iii2.3551
C11···H92.6799H10A···H13Aviii3.3663
C12···H72.4955H10A···H14Bviii3.3514
C13···H93.2749H10A···H15Cvii3.5062
C13···H10A2.8471H11B···O5vii3.5301
C13···H11B2.7500H11B···O6vii3.2335
C14···H10A2.7151H11B···C14vii3.4286
C14···H11B2.5313H11B···C15vii2.9753
C14···H12C3.1860H11B···C16vii2.8478
C14···H14B3.1008H11B···C17vii3.2523
C15···H83.2665H11B···C19vii3.0282
C15···H93.2713H11B···H5iii3.2546
C15···H13A3.1908H11B···H14Bvii2.7101
C15···H14B2.5665H11B···H15Cvii2.6154
C15···H15C2.6025H11B···H17Bvii3.5313
C16···H14B3.4580H12C···O3vi3.2371
C16···H15C2.9045H12C···O4viii2.6180
C16···H16A3.1935H12C···O5viii3.1429
C16···H17B2.6111H12C···C11vi3.3916
C16···H18C2.6155H12C···C16vii3.5908
C17···H72.5638H12C···C17vii3.4633
C17···H83.2767H12C···C18viii3.1347
C17···H17B2.7416H12C···C19viii3.0436
C17···H18C2.7583H12C···H9vii3.5166
C18···H82.6086H12C···H12Cviii2.7091
C20···H92.5292H12C···H13Aviii2.9594
H1···H63.5152H12C···H14Bviii2.6299
H2···H32.3168H12C···H17Bvii3.3110
H3···H42.3338H13A···O3vii3.1758
H4···H52.3358H13A···C6xii3.0406
H6···H72.1478H13A···C18viii3.5765
H7···H92.1713H13A···C20ix3.3118
H8···H10A2.3516H13A···H4xii2.0967
H8···H11B2.4712H13A···H10Aviii3.3663
H8···H12C3.5828H13A···H12Cviii2.9594
H9···H16A3.4997H13A···H16Aix2.8195
H9···H17B2.2971H13A···H17Bvi2.9562
H9···H18C2.3277H13A···H18Cix2.9032
O1···H1i2.6152H14B···O3vii2.7891
O1···H8iii3.5409H14B···C11vii3.3148
O2···H2iv3.1647H14B···C12vii3.1794
O2···H3vi3.2680H14B···C13vii2.7634
O2···H6v2.5946H14B···C14vii3.5351
O2···H7v2.1022H14B···C18viii3.4123
O2···H9v3.1049H14B···C18vii3.5508
O2···H18Cv3.4209H14B···H4xii3.4738
O3···H1vi3.5039H14B···H8vii2.4905
O3···H1iii3.0140H14B···H10Aviii3.3514
O3···H4i3.5084H14B···H11Bvii2.7101
O3···H5i3.1009H14B···H12Cviii2.6299
O3···H10Aii2.5210H15C···C6xiv3.4441
O3···H12Cii3.2371H15C···C7xiv3.0743
O3···H13Avii3.1758H15C···C9xiv3.1835
O3···H14Bvii2.7891H15C···C18vii3.4644
O4···H9vi3.0390H15C···C20ix3.3767
O4···H12Cviii2.6180H15C···H4xii3.5609
O5···H3v3.1552H15C···H5xiv3.2923
O5···H9vi3.4102H15C···H8vii3.2100
O5···H11Bvii3.5301H15C···H10Avii3.5062
O5···H12Cviii3.1429H15C···H11Bvii2.6154
O5···H16Aix2.5300H15C···H16Aix2.8571
O5···H17Bvi2.4880H15C···H18Cix3.1098
O5···H18Cix3.5978H16A···O5ix2.5300
O6···H2v3.4165H16A···O6ix2.7939
O6···H3v3.5440H16A···C5xiv3.4640
O6···H11Bvii3.2335H16A···C15ix3.4488
O6···H16Aix2.7939H16A···C16ix3.5794
N1···H5vi3.5731H16A···C19ix2.9135
N1···H5i3.4325H16A···C20xiii3.2931
N1···H8ii3.2075H16A···H3xiv3.1271
N1···H10Aii3.1491H16A···H4xiv3.5157
N2···H10Aii3.1687H16A···H13Aix2.8195
C1···H1i3.4562H16A···H15Cix2.8571
C1···H4vi3.4026H16A···H16Axiii3.0153
C1···H8ii3.3969H16A···H17Bxiii2.8319
C2···H4vi3.2626H16A···H18Cxiii3.5396
C3···H2iv3.4444H17B···O5ii2.4880
C3···H3vi3.5809H17B···C19ii3.2570
C3···H4vi3.5766H17B···C20xiii3.5118
C3···H7v3.3006H17B···H3iv3.1628
C3···H18Cv3.4000H17B···H4xiv3.3622
C4···H6ii3.3930H17B···H11Bvii3.5313
C4···H6iv3.5039H17B···H12Cvii3.3110
C4···H18Cv3.1614H17B···H13Aii2.9562
C5···H6ii3.3690H17B···H16Axiii2.8319
C5···H16Ax3.4640H17B···H17Bxiii3.4741
C5···H18Civ3.5979H18C···O2v3.4209
C6···H10Aiii3.5086H18C···O5ix3.5978
C6···H13Axi3.0406H18C···C3v3.4000
C6···H15Cx3.4441H18C···C4v3.1614
C7···H1i3.4734H18C···C5iv3.5979
C7···H8iii3.5908H18C···C8v3.2174
C7···H10Aiii3.0639H18C···C19ix3.3301
C7···H15Cx3.0743H18C···H2v3.2006
C8···H7ii3.5060H18C···H3iv2.8620
C8···H18Cv3.2174H18C···H4iv3.2072
C9···H1i3.4959H18C···H13Aix2.9032
C9···H15Cx3.1835H18C···H15Cix3.1098
C10···H2iv3.4588H18C···H16Axiii3.5396
C10···H6v3.5073
C1—O1—C9118.5 (4)C15—C16—C17119.5 (4)
C14—O4—C18117.6 (4)C12—C17—C16120.0 (4)
C15—O5—C19113.4 (3)N1—N2—H7119.645
C16—O6—C20116.6 (4)C11—N2—H7119.637
N2—N1—C10115.0 (3)O1—C1—H1117.355
N1—N2—C11120.7 (3)C2—C1—H1117.346
O1—C1—C2125.3 (4)C5—C4—H2119.811
C1—C2—C3119.3 (4)C8—C4—H2119.804
C1—C2—C10121.3 (4)C4—C5—H3120.079
C3—C2—C10119.4 (4)C6—C5—H3120.082
O2—C3—C2122.3 (4)C5—C6—H4119.339
O2—C3—C8122.5 (4)C7—C6—H4119.343
C2—C3—C8115.3 (4)C6—C7—H5121.057
C5—C4—C8120.4 (5)C9—C7—H5121.046
C4—C5—C6119.8 (6)N1—C10—H6119.366
C5—C6—C7121.3 (5)C2—C10—H6119.364
C6—C7—C9117.9 (6)C12—C13—H8120.275
C3—C8—C4122.0 (4)C14—C13—H8120.278
C3—C8—C9119.5 (4)C12—C17—H9119.980
C4—C8—C9118.5 (4)C16—C17—H9119.986
O1—C9—C7116.1 (5)O4—C18—H10A109.468
O1—C9—C8121.9 (4)O4—C18—H11B109.472
C7—C9—C8122.0 (5)O4—C18—H12C109.474
N1—C10—C2121.3 (4)H10A—C18—H11B109.465
O3—C11—N2123.6 (4)H10A—C18—H12C109.472
O3—C11—C12122.4 (4)H11B—C18—H12C109.476
N2—C11—C12114.0 (4)O5—C19—H13A109.472
C11—C12—C13118.8 (4)O5—C19—H14B109.472
C11—C12—C17121.0 (4)O5—C19—H15C109.473
C13—C12—C17120.1 (4)H13A—C19—H14B109.470
C12—C13—C14119.4 (4)H13A—C19—H15C109.473
O4—C14—C13124.6 (4)H14B—C19—H15C109.467
O4—C14—C15114.8 (4)O6—C20—H16A109.471
C13—C14—C15120.6 (4)O6—C20—H17B109.473
O5—C15—C14119.8 (4)O6—C20—H18C109.471
O5—C15—C16120.0 (4)H16A—C20—H17B109.473
C14—C15—C16120.2 (4)H16A—C20—H18C109.472
O6—C16—C15114.9 (4)H17B—C20—H18C109.467
O6—C16—C17125.6 (4)
C1—O1—C9—C7178.5 (3)H2—C4—C5—H32.5
C1—O1—C9—C81.5 (5)H2—C4—C8—C33.3
C9—O1—C1—C21.1 (6)H2—C4—C8—C9177.5
C9—O1—C1—H1178.9C4—C5—C6—C70.3 (7)
C14—O4—C18—H10A74.4C4—C5—C6—H4179.7
C14—O4—C18—H11B45.6H3—C5—C6—C7179.7
C14—O4—C18—H12C165.6H3—C5—C6—H40.3
C18—O4—C14—C1322.6 (5)C5—C6—C7—C91.7 (7)
C18—O4—C14—C15157.7 (3)C5—C6—C7—H5178.3
C15—O5—C19—H13A177.4H4—C6—C7—C9178.3
C15—O5—C19—H14B57.4H4—C6—C7—H51.7
C15—O5—C19—H15C62.6C6—C7—C9—O1178.3 (4)
C19—O5—C15—C1499.4 (4)C6—C7—C9—C81.6 (6)
C19—O5—C15—C1680.8 (4)H5—C7—C9—O11.7
C16—O6—C20—H16A179.7H5—C7—C9—C8178.4
C16—O6—C20—H17B59.7C3—C8—C9—O11.2 (5)
C16—O6—C20—H18C60.3C3—C8—C9—C7178.8 (3)
C20—O6—C16—C15180.0 (3)C4—C8—C9—O1179.6 (3)
C20—O6—C16—C170.7 (4)C4—C8—C9—C70.4 (6)
N2—N1—C10—C2176.9 (3)O3—C11—C12—C1328.2 (5)
N2—N1—C10—H63.1O3—C11—C12—C17149.3 (3)
C10—N1—N2—C11179.5 (3)N2—C11—C12—C13152.5 (3)
C10—N1—N2—H70.5N2—C11—C12—C1730.0 (4)
N1—N2—C11—O312.6 (5)C11—C12—C13—C14178.2 (3)
N1—N2—C11—C12166.8 (3)C11—C12—C13—H81.8
H7—N2—C11—O3167.4C11—C12—C17—C16180.0 (3)
H7—N2—C11—C1213.2C11—C12—C17—H90.0
O1—C1—C2—C32.1 (6)C13—C12—C17—C162.6 (4)
O1—C1—C2—C10178.3 (3)C13—C12—C17—H9177.4
H1—C1—C2—C3177.9C17—C12—C13—C140.7 (4)
H1—C1—C2—C101.7C17—C12—C13—H8179.3
C1—C2—C3—O2174.5 (3)C12—C13—C14—O4177.6 (3)
C1—C2—C3—C84.5 (5)C12—C13—C14—C152.7 (5)
C1—C2—C10—N11.0 (5)H8—C13—C14—O42.4
C1—C2—C10—H6179.0H8—C13—C14—C15177.3
C3—C2—C10—N1178.6 (3)O4—C14—C15—O54.2 (4)
C3—C2—C10—H61.4O4—C14—C15—C16176.0 (3)
C10—C2—C3—O25.1 (5)C13—C14—C15—O5175.5 (3)
C10—C2—C3—C8175.9 (3)C13—C14—C15—C164.2 (5)
O2—C3—C8—C44.2 (5)O5—C15—C16—O63.2 (4)
O2—C3—C8—C9175.0 (3)O5—C15—C16—C17177.4 (3)
C2—C3—C8—C4176.7 (3)C14—C15—C16—O6177.0 (3)
C2—C3—C8—C94.1 (5)C14—C15—C16—C172.3 (5)
C5—C4—C8—C3176.7 (4)O6—C16—C17—C12179.7 (3)
C5—C4—C8—C92.5 (6)O6—C16—C17—H90.3
C8—C4—C5—C62.4 (7)C15—C16—C17—C121.0 (4)
C8—C4—C5—H3177.6C15—C16—C17—H9179.0
H2—C4—C5—C6177.6
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) x1, y, z; (vii) x, y+1, z+2; (viii) x1, y+1, z+2; (ix) x, y, z+2; (x) x+1, y, z1; (xi) x+2, y, z1; (xii) x2, y, z+1; (xiii) x+1, y, z+2; (xiv) x1, y, z+1.
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C12–C17 ring.
D—H···AD—HH···AD···AD—H···A
N2—H7···O2v0.882.102.942 (6)159
C4—H2···Cgv0.952.973.716 (8)136
Symmetry code: (v) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C12–C17 ring.
D—H···AD—HH···AD···AD—H···A
N2—H7···O2i0.8802.1022.942 (6)159.3
C4—H2···Cgi0.952.973.716 (8)136
Symmetry code: (i) x+1, y, z+1.
 

Acknowledgements

We acknowledge University of Shizuoka for instrumental support.

References

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