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ISSN: 2056-9890

(E)-3,4,5-Trimeth­­oxy-N′-[(6-meth­­oxy-4-oxo-4H-chromen-3-yl)methyl­­idene]benzohydrazide monohydrate

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 3 June 2014; accepted 24 June 2014; online 2 July 2014)

In the title chromone-tethered benzohydrazide derivative, C21H20N2O7·H2O, the atoms of the 4H-chromen-4-one segment are essentially coplanar (r.m.s. deviation = 0.0073 Å) with the largest deviation from the mean plane [0.012 (3) Å] being found for the benzene C atom. The dihedral angles between the chromone segment and the hydrazide plane and between the chromone segment and the benzene ring of the tri­meth­oxy­benzene unit are 24.67 (9) and 41.28 (8) Å, respectively. The mol­ecule is connected to the solvent water mol­ecule by O—H⋯O hydrogen bonds and weak C—H⋯O inter­actions. Additional N—H⋯O inter­actions are observed and together they link the mol­ecules into chains forming a two-dimensional network along (011).

Keywords: crystal structure.

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: Ishikawa et al. (2014a[Ishikawa, Y. & Watanabe, K. (2014a). Acta Cryst. E70, o472.],b[Ishikawa, Y. & Watanabe, K. (2014b). Acta Cryst. E70, o565.]).

[Scheme 1]

Experimental

Crystal data
  • C21H20N2O7·H2O

  • Mr = 430.41

  • Triclinic, [P \overline 1]

  • a = 7.782 (3) Å

  • b = 9.015 (5) Å

  • c = 14.991 (6) Å

  • α = 103.17 (5)°

  • β = 96.51 (3)°

  • γ = 95.52 (4)°

  • V = 1009.4 (8) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 100 K

  • 0.30 × 0.20 × 0.18 mm

Data collection
  • Rigaku AFC-7R diffractometer

  • 5621 measured reflections

  • 4621 independent reflections

  • 3518 reflections with F2 > 2σ(F2)

  • Rint = 0.111

  • 3 standard reflections every 150 reflections intensity decay: 2.3%

Refinement
  • R[F2 > 2σ(F2)] = 0.076

  • wR(F2) = 0.230

  • S = 1.02

  • 4621 reflections

  • 292 parameters

  • H-atom parameters constrained

  • Δρmax = 0.65 e Å−3

  • Δρmin = −0.57 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O8—H21⋯O2i 0.91 1.93 2.829 (4) 168
O8—H22⋯O4 0.83 2.27 3.036 (3) 153
N2—H9⋯O6ii 0.88 2.28 3.062 (3) 149
C1—H1⋯O8 0.95 2.30 3.214 (4) 161
C4i—H2i⋯O8 0.95 2.60 3.489 (4) 155
Symmetry codes: (i) x, y+1, z; (ii) -x, -y, -z+1.

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999[Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.]); cell refinement: WinAFC Diffractometer Control Software; data reduction: WinAFC Diffractometer Control Software; program(s) used to solve structure: SIR2008 (Burla et al., 2007[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.]); 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 6-methoxy-3-formylchromone with 3,4,5-trimethoxybenzoylhydrazide in benzene.

The mean deviation of the least-square planes for the non-hydrogen atoms of the 4H-chromen-4-one segment is 0.0073 Å, and the largest deviation is 0.012 (3) Å for C6 (Fig.1) showing an essentially coplanar segment. The dihedral angles between this chromone segment and the hydrazide (N1/N2/C12/O4) plane and between the chromone segment and the benzene ring of the trimethoxybenzene unit are 24.67 (9) Å and 41.28 (8) Å, respectively. In the crystal, the molecule is connected to the solvent water molecule by O–H···O hydrogen bonds and weak O—H···O, C–H···O intermolecular interactions (Table 1). Additional weak N—H···O intermolecular interactions are observed and together they link the molecules into chains forming a 2-D network along (011) (Fig. 2).

Related literature top

For the biological activity of related compounds, see: Khan et al. (2009); Tu et al. (2013). For related structures, see: Ishikawa et al. (2014a,b).

Experimental top

3,4,5-Trimethoxybenzoylhydrazide (1.00 mmol), 6-methoxy-3-formylchromone (1.00mmol), and a few drops of acetic acid were dissolved in 25 ml of benzene, andthe mixture was refluxed with Dean-Stark apparatus for 6 h. After cooling, theprecipitates were collected, washed with n-hexane, and dried (yield 63.6%). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an acetonitrile solution of the title compound at room temperature. DART-MS calcd for [C21H20N2O7 + H+]: 413.135, found 413.158.

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)]. Hydrogen atoms of the water molecule were found in a difference Fourier map, and were refined using a riding model.

Computing details top

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).

Figures top
[Figure 1] Fig. 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. Crystal packing of the title compound viewed along the a axis. O–H···O hydrogen bonds and weak O—H···O, N—H···O, C–H···O intermolecular interactions are represented by dashed lines.
(E)-3,4,5-Trimethoxy-N'-[(6-methoxy-4-oxo-4H-chromen-3-yl)methylidene]benzohydrazide monohydrate top
Crystal data top
C21H20N2O7·H2OZ = 2
Mr = 430.41F(000) = 452.00
Triclinic, P1Dx = 1.416 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 7.782 (3) ÅCell parameters from 25 reflections
b = 9.015 (5) Åθ = 15.9–17.4°
c = 14.991 (6) ŵ = 0.11 mm1
α = 103.17 (5)°T = 100 K
β = 96.51 (3)°Block, colorless
γ = 95.52 (4)°0.30 × 0.20 × 0.18 mm
V = 1009.4 (8) Å3
Data collection top
Rigaku AFC-7R
diffractometer
θmax = 27.5°
ω–2θ scansh = 1010
5621 measured reflectionsk = 116
4621 independent reflectionsl = 1819
3518 reflections with F2 > 2σ(F2)3 standard reflections every 150 reflections
Rint = 0.111 intensity decay: 2.3%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.076Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.230H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.1645P)2 + 0.3451P]
where P = (Fo2 + 2Fc2)/3
4621 reflections(Δ/σ)max < 0.001
292 parametersΔρmax = 0.65 e Å3
0 restraintsΔρmin = 0.57 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C21H20N2O7·H2Oγ = 95.52 (4)°
Mr = 430.41V = 1009.4 (8) Å3
Triclinic, P1Z = 2
a = 7.782 (3) ÅMo Kα radiation
b = 9.015 (5) ŵ = 0.11 mm1
c = 14.991 (6) ÅT = 100 K
α = 103.17 (5)°0.30 × 0.20 × 0.18 mm
β = 96.51 (3)°
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.111
5621 measured reflections3 standard reflections every 150 reflections
4621 independent reflections intensity decay: 2.3%
3518 reflections with F2 > 2σ(F2)
Refinement top
R[F2 > 2σ(F2)] = 0.0760 restraints
wR(F2) = 0.230H-atom parameters constrained
S = 1.02Δρmax = 0.65 e Å3
4621 reflectionsΔρmin = 0.57 e Å3
292 parameters
Special details top

Experimental. 1H NMR (400 MHz, DMSO-d6): δ = 3.73 (s, 3H), 3.88 (s, 6H), 3.89 (s, 3H), 7.27 (s, 2H), 7.46 (dd, 1H, J = 2.9 and 9.3 Hz), 7.51 (d, 1H, J = 2.9 Hz), 7.72 (d, 1H, J = 9.3 Hz), 8.68 (s, 1H), 8.85 (s, 1H), 11.80 (s, 1H).

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
O10.7962 (3)0.25163 (18)1.03469 (11)0.0170 (4)
O20.5804 (3)0.17435 (19)0.88102 (12)0.0192 (4)
O30.9883 (3)0.23616 (19)1.16901 (11)0.0182 (4)
O40.4338 (3)0.4081 (2)0.68493 (12)0.0217 (4)
O50.2787 (2)0.0891 (2)0.52041 (11)0.0183 (4)
O60.2145 (2)0.16565 (18)0.36535 (11)0.0168 (4)
O70.0852 (3)0.3332 (2)0.35685 (11)0.0206 (4)
O80.6699 (3)0.5255 (3)0.86847 (14)0.0302 (5)
N10.4696 (3)0.1985 (3)0.78507 (12)0.0140 (4)
N20.3390 (3)0.1774 (2)0.71139 (13)0.0135 (4)
C10.6843 (3)0.2331 (3)0.95678 (15)0.0154 (5)
C20.6093 (3)0.0946 (3)0.90324 (14)0.0127 (5)
C30.6469 (3)0.0464 (3)0.92841 (14)0.0129 (5)
C40.8169 (3)0.1504 (3)1.04813 (15)0.0140 (5)
C50.9310 (3)0.1250 (3)1.12933 (15)0.0143 (5)
C60.9961 (3)0.0268 (3)1.17845 (15)0.0161 (5)
C70.9504 (3)0.1495 (3)1.14648 (15)0.0168 (5)
C80.7690 (3)0.0245 (3)1.01460 (14)0.0121 (5)
C90.8361 (3)0.1234 (3)1.06352 (15)0.0135 (5)
C100.9139 (4)0.3915 (3)1.12624 (18)0.0228 (6)
C110.4829 (3)0.0839 (3)0.82108 (14)0.0130 (5)
C120.3287 (3)0.2913 (3)0.66582 (15)0.0133 (5)
C130.1788 (3)0.2631 (3)0.58907 (15)0.0130 (5)
C140.0185 (3)0.1864 (3)0.59606 (15)0.0140 (5)
C150.1154 (3)0.1596 (3)0.52197 (15)0.0136 (5)
C160.0862 (3)0.2063 (3)0.44125 (15)0.0142 (5)
C170.0733 (3)0.2886 (3)0.43727 (15)0.0157 (5)
C180.2067 (3)0.3176 (3)0.51160 (15)0.0155 (5)
C190.3186 (3)0.0514 (3)0.60432 (16)0.0193 (5)
C200.3090 (4)0.2905 (4)0.35235 (19)0.0297 (7)
C210.2353 (4)0.4363 (4)0.35433 (17)0.0250 (6)
H10.65590.32250.93800.0184*
H20.77130.25221.01520.0168*
H31.07310.04371.23470.0193*
H40.99520.25121.17990.0202*
H5A0.93100.41631.06100.0273*
H6B0.78880.40301.13070.0273*
H7C0.97090.46141.15780.0273*
H80.40970.00990.79410.0156*
H90.26470.09280.69440.0162*
H100.00070.15300.65040.0168*
H110.31520.37390.50940.0186*
H12A0.24490.02450.61900.0231*
H13B0.44150.00860.59630.0231*
H14C0.29660.14430.65500.0231*
H15A0.38840.25830.29390.0357*
H16B0.22660.37880.35060.0357*
H17C0.37630.31930.40370.0357*
H18A0.34010.38520.36030.0300*
H19B0.24480.52770.40550.0300*
H20C0.22380.46680.29540.0300*
H210.62560.61580.86960.0244*
H220.60690.46530.82370.0513*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0212 (9)0.0130 (8)0.0137 (8)0.0027 (6)0.0035 (7)0.0019 (6)
O20.0221 (9)0.0137 (8)0.0171 (8)0.0023 (7)0.0051 (7)0.0001 (6)
O30.0233 (9)0.0160 (9)0.0139 (8)0.0005 (7)0.0003 (7)0.0031 (6)
O40.0215 (9)0.0183 (9)0.0213 (9)0.0093 (7)0.0059 (7)0.0060 (7)
O50.0122 (8)0.0263 (9)0.0138 (8)0.0063 (7)0.0002 (6)0.0041 (7)
O60.0193 (9)0.0155 (8)0.0109 (8)0.0032 (7)0.0034 (6)0.0015 (6)
O70.0243 (9)0.0239 (9)0.0103 (8)0.0108 (7)0.0019 (7)0.0049 (7)
O80.0449 (12)0.0144 (9)0.0239 (10)0.0013 (9)0.0122 (9)0.0000 (8)
N10.0133 (9)0.0170 (9)0.0098 (9)0.0019 (7)0.0009 (7)0.0012 (7)
N20.0135 (9)0.0127 (9)0.0113 (9)0.0045 (7)0.0014 (7)0.0013 (7)
C10.0170 (11)0.0151 (11)0.0130 (10)0.0007 (9)0.0010 (8)0.0040 (8)
C20.0126 (10)0.0150 (11)0.0095 (10)0.0020 (8)0.0013 (8)0.0023 (8)
C30.0127 (10)0.0141 (11)0.0103 (10)0.0010 (8)0.0014 (8)0.0007 (8)
C40.0152 (11)0.0140 (11)0.0114 (10)0.0006 (8)0.0034 (8)0.0003 (8)
C50.0146 (11)0.0177 (11)0.0120 (10)0.0026 (8)0.0060 (8)0.0040 (8)
C60.0165 (11)0.0207 (12)0.0086 (10)0.0011 (9)0.0022 (8)0.0016 (8)
C70.0204 (12)0.0153 (11)0.0105 (10)0.0034 (9)0.0007 (9)0.0020 (8)
C80.0116 (10)0.0149 (11)0.0086 (10)0.0008 (8)0.0019 (8)0.0014 (8)
C90.0164 (11)0.0123 (10)0.0117 (10)0.0001 (8)0.0032 (8)0.0031 (8)
C100.0306 (14)0.0144 (12)0.0222 (12)0.0013 (10)0.0013 (10)0.0051 (9)
C110.0129 (10)0.0150 (11)0.0094 (10)0.0009 (8)0.0024 (8)0.0001 (8)
C120.0128 (10)0.0138 (10)0.0112 (10)0.0014 (8)0.0006 (8)0.0008 (8)
C130.0159 (11)0.0095 (10)0.0107 (10)0.0008 (8)0.0007 (8)0.0013 (8)
C140.0162 (11)0.0135 (10)0.0112 (10)0.0008 (8)0.0031 (8)0.0007 (8)
C150.0131 (10)0.0113 (10)0.0136 (10)0.0019 (8)0.0023 (8)0.0018 (8)
C160.0149 (11)0.0121 (10)0.0115 (10)0.0005 (8)0.0023 (8)0.0024 (8)
C170.0213 (12)0.0145 (10)0.0091 (10)0.0009 (9)0.0014 (9)0.0002 (8)
C180.0161 (11)0.0150 (11)0.0127 (10)0.0035 (8)0.0000 (9)0.0008 (8)
C190.0142 (11)0.0276 (13)0.0155 (11)0.0035 (9)0.0049 (9)0.0051 (9)
C200.0321 (15)0.0259 (14)0.0234 (13)0.0072 (11)0.0108 (11)0.0044 (11)
C210.0240 (13)0.0315 (14)0.0171 (12)0.0119 (11)0.0010 (10)0.0096 (10)
Geometric parameters (Å, º) top
O1—C11.343 (3)C13—C181.391 (4)
O1—C91.373 (3)C14—C151.394 (3)
O2—C31.238 (3)C15—C161.403 (4)
O3—C51.362 (4)C16—C171.398 (4)
O3—C101.435 (3)C17—C181.393 (3)
O4—C121.226 (3)O8—H210.911
O5—C151.360 (3)O8—H220.832
O5—C191.434 (4)N2—H90.880
O6—C161.381 (3)C1—H10.950
O6—C201.440 (4)C4—H20.950
O7—C171.364 (4)C6—H30.950
O7—C211.431 (4)C7—H40.950
N1—N21.379 (3)C10—H5A0.980
N1—C111.277 (4)C10—H6B0.980
N2—C121.361 (4)C10—H7C0.980
C1—C21.357 (3)C11—H80.950
C2—C31.451 (4)C14—H100.950
C2—C111.465 (3)C18—H110.950
C3—C81.477 (3)C19—H12A0.980
C4—C51.382 (3)C19—H13B0.980
C4—C81.407 (4)C19—H14C0.980
C5—C61.412 (4)C20—H15A0.980
C6—C71.363 (4)C20—H16B0.980
C7—C91.403 (3)C20—H17C0.980
C8—C91.387 (3)C21—H18A0.980
C12—C131.502 (3)C21—H19B0.980
C13—C141.394 (4)C21—H20C0.980
O1···C32.852 (3)C10···H4iv3.5884
O2···C13.571 (4)C10···H5Axiv3.3602
O2···C42.889 (3)C10···H10i3.4958
O2···C112.818 (4)C11···H2i3.4958
O4···N12.683 (4)C11···H13Bx3.4119
O4···C143.576 (4)C11···H14Cx3.2939
O4···C182.874 (3)C11···H15Aviii3.1437
O5···O62.656 (3)C11···H223.4710
O5···C203.425 (4)C12···H6Bi3.2503
O6···O72.686 (3)C12···H13Bx3.2962
O7···C203.046 (4)C12···H14Cx3.3222
N1···C12.842 (3)C12···H16Bv3.2064
N2···C142.889 (3)C12···H223.0406
N2···C183.593 (4)C13···H12Aviii3.4843
C1···C73.589 (4)C13···H16Bv3.1208
C1···C82.768 (4)C14···H19Bv3.4454
C2···C92.761 (4)C15···H9viii3.5099
C4···C72.804 (4)C15···H19Bv3.0881
C4···C102.818 (4)C16···H3ix3.5247
C5···C92.773 (4)C16···H9viii3.0781
C6···C82.777 (4)C16···H10viii3.3785
C11···C123.484 (4)C16···H12Aviii3.2876
C13···C162.769 (4)C16···H19Bv3.3541
C14···C172.802 (4)C17···H3ix3.3226
C14···C192.812 (4)C17···H12Aviii2.8491
C15···C182.800 (4)C18···H12Aviii2.9718
C15···C203.312 (5)C18···H16Bv3.0081
C17···C203.104 (4)C18···H17Cv3.3107
C18···C212.824 (4)C19···H3i3.2283
O1···O2i3.394 (3)C19···H13Bvii3.2584
O1···C4ii3.507 (4)C20···H8viii2.9211
O1···C5ii3.497 (4)C20···H9viii3.4245
O1···C10iii3.195 (4)C20···H11v3.2627
O2···O1i3.394 (3)C20···H13Bvii3.4512
O2···O8iv2.829 (4)C20···H18Axii2.9457
O2···C1i3.457 (4)C20···H19Bv3.5820
O2···C9i3.483 (4)C21···H4ix3.0689
O3···N2i3.293 (3)C21···H15Ax3.5799
O3···C1ii3.339 (4)C21···H17Cx3.3552
O3···C14i3.454 (4)C21···H21vi3.5871
O4···O83.036 (3)C21···H22vi3.3215
O4···C20v3.117 (4)H1···O3ii3.4201
O4···C21vi2.995 (4)H1···O82.3023
O5···O5vii3.583 (3)H1···H2i3.5037
O5···C13viii3.431 (4)H1···H5Aiii3.1121
O5···C19vii3.429 (3)H1···H5Aii3.2421
O6···N2viii3.062 (3)H1···H6Biii3.3336
O6···C6ix3.455 (4)H1···H213.0649
O6···C11viii3.485 (3)H1···H222.3846
O7···C6ix3.332 (4)H2···O1ii3.5296
O7···C7ix3.213 (3)H2···O8iv2.6024
O8···O2iii2.829 (4)H2···C9ii3.5823
O8···O43.036 (3)H2···C11i3.4958
O8···N13.111 (4)H2···H1i3.5037
O8···C13.214 (4)H2···H21iv2.3369
O8···C4iii3.489 (4)H2···H22iv3.4017
O8···C10ii3.563 (4)H3···O6xi3.2462
O8···C21vi3.585 (4)H3···O7xi2.8119
N1···O83.111 (4)H3···C2ii3.5376
N1···C5i3.564 (4)H3···C3ii3.4572
N1···C19x3.408 (4)H3···C16xi3.5247
N2···O3i3.293 (3)H3···C17xi3.3226
N2···O6viii3.062 (3)H3···C19i3.2283
N2···C5i3.435 (4)H3···H9i3.1881
N2···C19x3.418 (4)H3···H10i2.8039
C1···O2i3.457 (4)H3···H12Ai2.4864
C1···O3ii3.339 (4)H3···H14Ci3.1349
C1···O83.214 (4)H3···H18Axi3.5468
C1···C5ii3.527 (4)H4···O6xi3.5710
C2···C3i3.465 (4)H4···O7xi2.5808
C2···C4i3.534 (4)H4···O8xiii3.3844
C2···C8i3.377 (4)H4···C10iii3.5884
C3···C2i3.465 (4)H4···C21xi3.0689
C3···C3i3.346 (4)H4···H7Ciii2.7068
C3···C6ii3.370 (4)H4···H16Bxi3.3011
C3···C7ii3.582 (4)H4···H18Axi3.4956
C3···C8i3.520 (4)H4···H20Cxi2.6541
C4···O1ii3.507 (4)H4···H21xiii3.3041
C4···O8iv3.489 (4)H5A···O1iv2.9971
C4···C2i3.534 (4)H5A···O1ii3.1342
C4···C9ii3.352 (4)H5A···O8iv3.2416
C4···C11i3.228 (4)H5A···O8ii3.4717
C5···O1ii3.497 (4)H5A···C1iv3.4670
C5···N1i3.564 (4)H5A···C1ii3.3456
C5···N2i3.435 (4)H5A···C10xiv3.3602
C5···C1ii3.527 (4)H5A···H1iv3.1121
C5···C9ii3.584 (4)H5A···H1ii3.2421
C5···C11i3.423 (4)H5A···H5Axiv2.5047
C6···O6xi3.455 (4)H5A···H7Cxiv3.4116
C6···O7xi3.332 (4)H5A···H21iv3.5951
C6···C3ii3.370 (4)H6B···O1iv3.1272
C6···C8ii3.591 (4)H6B···O4i3.4309
C7···O7xi3.213 (3)H6B···N1i3.0437
C7···C3ii3.582 (4)H6B···N2i3.0758
C7···C8ii3.507 (4)H6B···C12i3.2503
C8···C2i3.377 (4)H6B···H1iv3.3336
C8···C3i3.520 (4)H6B···H9i3.4644
C8···C6ii3.591 (4)H6B···H21i3.5895
C8···C7ii3.507 (4)H6B···H22i3.2534
C8···C9ii3.532 (4)H7C···O1iv2.9201
C8···C11i3.419 (4)H7C···O8ii2.9597
C9···O2i3.483 (4)H7C···C7iv3.4597
C9···C4ii3.352 (4)H7C···H4iv2.7068
C9···C5ii3.584 (4)H7C···H5Axiv3.4116
C9···C8ii3.532 (4)H7C···H10i3.4846
C10···O1iv3.195 (4)H7C···H20Cxv2.9120
C10···O8ii3.563 (4)H7C···H21ii3.5831
C11···O6viii3.485 (3)H7C···H22ii3.2704
C11···C4i3.228 (4)H8···O6viii2.6893
C11···C5i3.423 (4)H8···C4i3.2662
C11···C8i3.419 (4)H8···C5i3.2398
C13···O5viii3.431 (4)H8···C6i3.2243
C14···O3i3.454 (4)H8···C7i3.2599
C14···C15viii3.417 (4)H8···C8i3.2910
C14···C16viii3.557 (4)H8···C9i3.2870
C15···C14viii3.417 (4)H8···C20viii2.9211
C15···C15viii3.513 (4)H8···H13Bx3.3359
C16···C14viii3.557 (4)H8···H15Aviii2.3060
C19···O5vii3.429 (3)H8···H16Bviii3.5914
C19···N1xii3.408 (4)H8···H17Cviii3.5439
C19···N2xii3.418 (4)H9···O3i3.1526
C20···O4v3.117 (4)H9···O5viii3.2824
C21···O4vi2.995 (4)H9···O6viii2.2751
C21···O8vi3.585 (4)H9···C5i3.1682
O1···H42.5254H9···C6i3.2112
O2···H22.6293H9···C15viii3.5099
O2···H82.5548H9···C16viii3.0781
O3···H22.6658H9···C20viii3.4245
O3···H32.4842H9···H3i3.1881
O4···H93.0559H9···H6Bi3.4644
O4···H112.6258H9···H13Bx2.9239
O5···H102.6722H9···H14Cx3.5354
O5···H17C3.0991H9···H15Aviii3.4315
O7···H112.6708H10···O3i2.6288
O7···H16B2.4953H10···O6viii3.4311
N1···H12.5246H10···C5i3.3557
N2···H82.3806H10···C6i3.3319
N2···H102.6591H10···C10i3.4958
C1···H83.2858H10···C16viii3.3785
C3···H13.2893H10···H3i2.8039
C3···H22.6897H10···H7Ci3.4846
C3···H82.6729H11···C20v3.2627
C4···H33.2702H11···H11vi3.5697
C4···H5A2.6739H11···H12Aviii3.2547
C4···H6B2.8310H11···H16Bv2.8879
C5···H43.2774H11···H17Cx3.0416
C5···H5A2.5926H11···H17Cv2.7454
C5···H6B2.6464H11···H18Avi3.3895
C5···H7C3.1970H11···H19Bvi3.4714
C6···H23.2796H12A···O7viii3.2314
C8···H43.2835H12A···C6i3.4168
C9···H13.1871H12A···C13viii3.4843
C9···H23.2735H12A···C16viii3.2876
C9···H33.2441H12A···C17viii2.8491
C10···H22.5261H12A···C18viii2.9718
C11···H12.5886H12A···H3i2.4864
C11···H92.4215H12A···H11viii3.2547
C12···H102.6922H12A···H18Aviii3.3566
C12···H112.6109H13B···O5vii2.5780
C13···H92.5219H13B···O6vii3.1493
C14···H92.6067H13B···N1xii3.1430
C14···H113.2873H13B···N2xii2.8594
C14···H12A2.7645H13B···C11xii3.4119
C14···H14C2.7202H13B···C12xii3.2962
C15···H12A2.6452H13B···C19vii3.2584
C15···H13B3.1946H13B···C20vii3.4512
C15···H14C2.5898H13B···H8xii3.3359
C15···H17C3.2016H13B···H9xii2.9239
C16···H103.2841H13B···H13Bvii2.8924
C16···H113.2787H13B···H15Avii3.4548
C16···H15A3.1837H13B···H17Cvii3.1537
C16···H16B2.5320H14C···O3i3.2548
C16···H17C2.6211H14C···O4xii3.3077
C17···H16B2.8208H14C···N1xii2.8099
C17···H17C3.5252H14C···N2xii3.0718
C17···H18A2.6551H14C···C11xii3.2939
C17···H19B2.5901H14C···C12xii3.3222
C17···H20C3.1984H14C···H3i3.1349
C18···H103.2877H14C···H9xii3.5354
C18···H18A2.7626H14C···H19Bv3.2867
C18···H19B2.7518H14C···H20Cv3.3909
C19···H102.5246H14C···H22xii3.5848
C21···H112.5388H15A···O2viii2.7699
C21···H16B3.5746H15A···O4v3.0111
H1···H83.5095H15A···C11viii3.1437
H2···H5A2.1969H15A···C21xii3.5799
H2···H6B2.4330H15A···H8viii2.3060
H2···H7C3.4914H15A···H9viii3.4315
H3···H42.3125H15A···H13Bvii3.4548
H8···H92.1942H15A···H18Axii2.6808
H9···H102.2409H15A···H21v3.3693
H10···H12A2.3019H16B···O4v2.7282
H10···H13B3.4955H16B···C12v3.2064
H10···H14C2.3167H16B···C13v3.1208
H11···H18A2.2895H16B···C18v3.0081
H11···H19B2.3634H16B···H4ix3.3011
H11···H20C3.5100H16B···H8viii3.5914
O1···H2ii3.5296H16B···H11v2.8879
O1···H5Aiii2.9971H16B···H18Axii3.3970
O1···H5Aii3.1342H16B···H19Bv3.5817
O1···H6Biii3.1272H17C···O4v3.0931
O1···H7Ciii2.9201H17C···C18v3.3107
O2···H15Aviii2.7699H17C···C21xii3.3552
O2···H21iv1.9305H17C···H8viii3.5439
O2···H22iv3.1983H17C···H11xii3.0416
O3···H1ii3.4201H17C···H11v2.7454
O3···H9i3.1526H17C···H13Bvii3.1537
O3···H10i2.6288H17C···H18Axii2.3976
O3···H14Ci3.2548H17C···H19Bv2.8980
O4···H6Bi3.4309H18A···O4vi2.6920
O4···H14Cx3.3077H18A···C20x2.9457
O4···H15Av3.0111H18A···H3ix3.5468
O4···H16Bv2.7282H18A···H4ix3.4956
O4···H17Cv3.0931H18A···H11vi3.3895
O4···H18Avi2.6920H18A···H12Aviii3.3566
O4···H19Bvi3.0461H18A···H15Ax2.6808
O4···H20Cvi2.7482H18A···H16Bx3.3970
O4···H213.0925H18A···H17Cx2.3976
O4···H222.2696H18A···H21vi3.4855
O5···H9viii3.2824H18A···H22vi3.3830
O5···H13Bvii2.5780H19B···O4vi3.0461
O5···H19Bv3.3534H19B···O5v3.3534
O6···H3ix3.2462H19B···C14v3.4454
O6···H4ix3.5710H19B···C15v3.0881
O6···H8viii2.6893H19B···C16v3.3541
O6···H9viii2.2751H19B···C20v3.5820
O6···H10viii3.4311H19B···H11vi3.4714
O6···H13Bvii3.1493H19B···H14Cv3.2867
O7···H3ix2.8119H19B···H16Bv3.5817
O7···H4ix2.5808H19B···H17Cv2.8980
O7···H12Aviii3.2314H20C···O4vi2.7482
O8···H12.3023H20C···O8vi2.6934
O8···H2iii2.6024H20C···C7ix3.5405
O8···H4xiii3.3844H20C···H4ix2.6541
O8···H5Aiii3.2416H20C···H7Cxvi2.9120
O8···H5Aii3.4717H20C···H14Cv3.3909
O8···H7Cii2.9597H20C···H21vi2.8349
O8···H20Cvi2.6934H20C···H22vi2.4858
N1···H6Bi3.0437H21···O2iii1.9305
N1···H13Bx3.1430H21···O43.0925
N1···H14Cx2.8099H21···C3iii2.9543
N1···H222.4483H21···C4iii3.1214
N2···H6Bi3.0758H21···C8iii3.4679
N2···H13Bx2.8594H21···C21vi3.5871
N2···H14Cx3.0718H21···H13.0649
N2···H223.1769H21···H2iii2.3369
C1···H5Aiii3.4670H21···H4xiii3.3041
C1···H5Aii3.3456H21···H5Aiii3.5951
C1···H223.2556H21···H6Bi3.5895
C2···H3ii3.5376H21···H7Cii3.5831
C3···H3ii3.4572H21···H15Av3.3693
C3···H21iv2.9543H21···H18Avi3.4855
C4···H8i3.2662H21···H20Cvi2.8349
C4···H21iv3.1214H22···O2iii3.1983
C5···H8i3.2398H22···O42.2696
C5···H9i3.1682H22···N12.4483
C5···H10i3.3557H22···N23.1769
C6···H8i3.2243H22···C13.2556
C6···H9i3.2112H22···C113.4710
C6···H10i3.3319H22···C123.0406
C6···H12Ai3.4168H22···C21vi3.3215
C7···H7Ciii3.4597H22···H12.3846
C7···H8i3.2599H22···H2iii3.4017
C7···H20Cxi3.5405H22···H6Bi3.2534
C8···H8i3.2910H22···H7Cii3.2704
C8···H21iv3.4679H22···H14Cx3.5848
C9···H2ii3.5823H22···H18Avi3.3830
C9···H8i3.2870H22···H20Cvi2.4858
C1—O1—C9118.55 (17)C13—C18—C17119.1 (3)
C5—O3—C10116.88 (18)H21—O8—H22102.354
C15—O5—C19116.87 (17)N1—N2—H9121.020
C16—O6—C20113.23 (18)C12—N2—H9121.023
C17—O7—C21117.20 (18)O1—C1—H1117.948
N2—N1—C11115.76 (18)C2—C1—H1117.948
N1—N2—C12117.96 (18)C5—C4—H2120.251
O1—C1—C2124.1 (3)C8—C4—H2120.249
C1—C2—C3120.6 (2)C5—C6—H3119.452
C1—C2—C11120.9 (3)C7—C6—H3119.456
C3—C2—C11118.44 (18)C6—C7—H4120.489
O2—C3—C2122.1 (2)C9—C7—H4120.492
O2—C3—C8123.1 (3)O3—C10—H5A109.473
C2—C3—C8114.81 (18)O3—C10—H6B109.469
C5—C4—C8119.5 (2)O3—C10—H7C109.473
O3—C5—C4125.4 (2)H5A—C10—H6B109.469
O3—C5—C6114.78 (19)H5A—C10—H7C109.473
C4—C5—C6119.8 (3)H6B—C10—H7C109.469
C5—C6—C7121.1 (2)N1—C11—H8119.431
C6—C7—C9119.0 (2)C2—C11—H8119.431
C3—C8—C4121.32 (19)C13—C14—H10120.569
C3—C8—C9119.0 (3)C15—C14—H10120.565
C4—C8—C9119.6 (2)C13—C18—H11120.463
O1—C9—C7116.20 (19)C17—C18—H11120.485
O1—C9—C8122.9 (2)O5—C19—H12A109.468
C7—C9—C8120.9 (3)O5—C19—H13B109.467
N1—C11—C2121.14 (19)O5—C19—H14C109.472
O4—C12—N2123.0 (2)H12A—C19—H13B109.473
O4—C12—C13122.0 (3)H12A—C19—H14C109.473
N2—C12—C13114.93 (19)H13B—C19—H14C109.474
C12—C13—C14121.0 (3)O6—C20—H15A109.471
C12—C13—C18117.2 (2)O6—C20—H16B109.474
C14—C13—C18121.8 (2)O6—C20—H17C109.469
C13—C14—C15118.9 (3)H15A—C20—H16B109.475
O5—C15—C14124.9 (3)H15A—C20—H17C109.468
O5—C15—C16115.10 (19)H16B—C20—H17C109.470
C14—C15—C16120.0 (2)O7—C21—H18A109.468
O6—C16—C15119.2 (2)O7—C21—H19B109.474
O6—C16—C17120.8 (3)O7—C21—H20C109.471
C15—C16—C17120.1 (2)H18A—C21—H19B109.464
O7—C17—C16115.1 (2)H18A—C21—H20C109.476
O7—C17—C18124.8 (3)H19B—C21—H20C109.475
C16—C17—C18120.1 (3)
C1—O1—C9—C7178.53 (18)C8—C4—C5—O3179.8 (2)
C1—O1—C9—C81.5 (4)C8—C4—C5—C60.9 (4)
C9—O1—C1—C21.1 (4)H2—C4—C5—O30.2
C9—O1—C1—H1178.9H2—C4—C5—C6179.1
C5—O3—C10—H5A55.8H2—C4—C8—C30.3
C5—O3—C10—H6B64.2H2—C4—C8—C9179.8
C5—O3—C10—H7C175.8O3—C5—C6—C7179.66 (19)
C10—O3—C5—C44.8 (4)O3—C5—C6—H30.3
C10—O3—C5—C6174.59 (19)C4—C5—C6—C70.9 (4)
C15—O5—C19—H12A64.3C4—C5—C6—H3179.0
C15—O5—C19—H13B175.7C5—C6—C7—C90.2 (4)
C15—O5—C19—H14C55.7C5—C6—C7—H4179.8
C19—O5—C15—C145.4 (3)H3—C6—C7—C9179.8
C19—O5—C15—C16174.81 (17)H3—C6—C7—H40.2
C16—O6—C20—H15A173.5C6—C7—C9—O1179.5 (2)
C16—O6—C20—H16B53.5C6—C7—C9—C80.5 (4)
C16—O6—C20—H17C66.5H4—C7—C9—O10.5
C20—O6—C16—C15104.0 (3)H4—C7—C9—C8179.5
C20—O6—C16—C1778.1 (3)C3—C8—C9—O11.0 (4)
C17—O7—C21—H18A65.0C3—C8—C9—C7179.00 (18)
C17—O7—C21—H19B55.0C4—C8—C9—O1179.5 (2)
C17—O7—C21—H20C175.0C4—C8—C9—C70.5 (4)
C21—O7—C17—C16171.11 (19)O4—C12—C13—C14145.3 (2)
C21—O7—C17—C189.9 (4)O4—C12—C13—C1834.3 (3)
N2—N1—C11—C2176.26 (17)N2—C12—C13—C1435.3 (3)
N2—N1—C11—H83.7N2—C12—C13—C18145.18 (19)
C11—N1—N2—C12174.65 (18)C12—C13—C14—C15178.41 (18)
C11—N1—N2—H95.4C12—C13—C14—H101.6
N1—N2—C12—O43.1 (4)C12—C13—C18—C17177.47 (17)
N1—N2—C12—C13177.47 (16)C12—C13—C18—H112.5
H9—N2—C12—O4176.9C14—C13—C18—C173.0 (4)
H9—N2—C12—C132.5C14—C13—C18—H11177.0
O1—C1—C2—C30.2 (4)C18—C13—C14—C152.1 (4)
O1—C1—C2—C11177.52 (19)C18—C13—C14—H10177.9
H1—C1—C2—C3179.8C13—C14—C15—O5178.63 (19)
H1—C1—C2—C112.5C13—C14—C15—C161.6 (3)
C1—C2—C3—O2179.9 (2)H10—C14—C15—O51.4
C1—C2—C3—C80.3 (3)H10—C14—C15—C16178.4
C1—C2—C11—N116.5 (4)O5—C15—C16—O66.1 (3)
C1—C2—C11—H8163.5O5—C15—C16—C17175.94 (17)
C3—C2—C11—N1166.10 (19)C14—C15—C16—O6173.72 (19)
C3—C2—C11—H813.9C14—C15—C16—C174.2 (4)
C11—C2—C3—O22.6 (4)O6—C16—C17—O74.5 (3)
C11—C2—C3—C8177.11 (18)O6—C16—C17—C18174.60 (18)
O2—C3—C8—C40.1 (4)C15—C16—C17—O7177.63 (19)
O2—C3—C8—C9179.6 (2)C15—C16—C17—C183.3 (4)
C2—C3—C8—C4179.60 (18)O7—C17—C18—C13178.71 (19)
C2—C3—C8—C90.1 (3)O7—C17—C18—H111.3
C5—C4—C8—C3179.71 (19)C16—C17—C18—C130.3 (4)
C5—C4—C8—C90.2 (4)C16—C17—C18—H11179.7
Symmetry codes: (i) x+1, y, z+2; (ii) x+2, y, z+2; (iii) x, y+1, z; (iv) x, y1, z; (v) x, y+1, z+1; (vi) x+1, y+1, z+1; (vii) x1, y, z+1; (viii) x, y, z+1; (ix) x1, y, z1; (x) x+1, y, z; (xi) x+1, y, z+1; (xii) x1, y, z; (xiii) x+2, y+1, z+2; (xiv) x+2, y1, z+2; (xv) x+1, y1, z+1; (xvi) x1, y+1, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O8—H21···O2iii0.911.932.829 (4)168
O8—H22···O40.832.273.036 (3)153
N2—H9···O6viii0.882.283.062 (3)149
C1—H1···O80.952.303.214 (4)161
C4iii—H2iii···O80.952.603.489 (4)155
Symmetry codes: (iii) x, y+1, z; (viii) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O8—H21···O2i0.9111.9302.829 (4)168.3
O8—H22···O40.8322.2703.036 (3)153.3
N2—H9···O6ii0.8802.2753.062 (3)148.8
C1—H1···O80.952.3023.214 (4)160.5
C4i—H2i···O80.952.6023.489 (4)155.4
Symmetry codes: (i) x, y+1, z; (ii) x, y, z+1.
 

Acknowledgements

We acknowledge the University of Shizuoka for instrumental support.

References

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