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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 10| October 2013| Page o1596
doi:10.1107/S1600536813026482

4′-Acetyl-3′′-carbamoyl-[1,1′:3′,1′′-terphen­yl]-2-carb­­oxy­lic acid

Yoshinobu Ishikawa,a* Nanako Yoshidaa and Takafumi Suzukia

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 8 July 2013; accepted 24 September 2013; online 28 September 2013)

In the title m-terphenyl derivative, C22H17NO4, the dihedral angles between the aromatic rings of the benzoic acid–acetophenone, acetophenone–benzamide and benzoic acid–benzamide units are 45.39 (8), 48.02 (8) and 42.93 (8)°, respectively. The carbamoyl and carboxyl groups are disordered with a refined occupancy ratio of 0.558 (15):0.442 (15). In the crystal, mol­ecules are linked through O—H⋯O and N—H⋯O hydrogen bonds between terminal carboxyl and carbamoyl groups in a bidentate manner, and anti­parallel helices are formed which extend along the b-axis direction.

CCDC reference: 963026

Related literature

For background to this study, see: Ishikawa & Fujii (2011[Ishikawa, Y. & Fujii, S. (2011). Bioinformation, 6, 221-225.]). For related structures, see: Schnobrich et al. (2010[Schnobrich, J. K., Lebel, O., Cychosz, K. A., Dailly, A., Wong-Foy, A. G. & Matzger, A. J. (2010). J. Am. Chem. Soc. 132, 13941-13948.]); Fun et al. (2012[Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o163.]); Liu et al. (2013[Liu, Y., Li, J. R., Verdegaal, W. M., Liu, T. F. & Zhou, H. C. (2013). Chemistry, 19, 5637-5643.]). For the biological activity of a related compound, see: Tomassini et al. (1994[Tomassini, J., Selnick, H., Davies, M. E., Armstrong, M. E., Baldwin, J., Bourgeois, M., Hastings, J., Hazuda, D., Lewis, J., McClements, W., Ponticello, G., Radzilowski, E., Smith, G., Tebben, A. & Wolfe, A. (1994). Antimicrob. Agents Chemother. 38, 2827-2837.]).

[Scheme 1]

Experimental

Crystal data

  • C22H17NO4

  • Mr = 359.38

  • Monoclinic, P 21 /c

  • a = 13.076 (4) Å

  • b = 20.581 (5) Å

  • c = 6.725 (3) Å

  • β = 104.10 (3)°

  • V = 1755.2 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100 K

  • 0.38 × 0.25 × 0.20 mm
Data collection

  • Rigaku AFC-7R diffractometer

  • 4953 measured reflections

  • 4026 independent reflections

  • 2389 reflections with F2 > 2σ(F2)

  • Rint = 0.014

  • 3 standard reflections every 150 reflections intensity decay: 0.6%
Refinement

  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.132

  • S = 1.01

  • 4026 reflections

  • 284 parameters

  • 10 restraints

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.34 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O25A—H25A⋯O27Ai 0.84 1.72 2.544 (9) 168
O25B—H25B⋯O27Bi 0.84 1.72 2.546 (8) 167
N23A—H23A⋯O24Aii 0.88 1.80 2.661 (8) 166
N23B—H23C⋯O24Bii 0.88 1.83 2.667 (10) 161
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

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: 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

CCDC reference: 963026

Crystal structure: contains datablocks General, I. DOI: 10.1107/S1600536813026482/rn2118sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813026482/rn2118Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813026482/rn2118Isup3.cml

checkCIF report


Comment top

Aryl diketo acids are known to inhibit influenza virus endonuclease (Tomassini et al. 1994). According to our inhibitor design targeting this metalloenzyme (Ishikawa & Fujii 2011), we synthesized the title compound by hydrolysis of methyl 4'-acetyl-3''-carbamoyl-[1,1':3',1''-terphenyl]-2-carboxylate, where the m-terphenyl derivatives are the synthetic intermediates of a final m-terphenyl diketo acid. The dihedral angles between A (C1/C2/C3/C4/C5/C6) and B (C7/C8/C9/C10/C11/C12), B and C (C13/C14/C15/C16/C17/C18), and A and C rings are 45.39 (8), 48.02 (8) and 42.93 (8)°, respectively (Fig. 1). The carbamoyl and carboxyl groups are disordered with a refined occupancy ratio of 0.558 (15) (A): 0.442 (15) (B). In the crystal, anti-parallel helices are formed through intermolecular O–H···O and N–H···O hydrogen bonds between terminal carboxylic acid and carbamoyl groups in a bidentate manner (Table 1), and align parallel to the b axis (Fig. 2 and 3).

Related literature top

For background to this study, see: Ishikawa & Fujii (2011). For related structures, see: Schnobrich et al. (2010); Fun et al. (2012); Liu et al. (2013). For the biological activity of a related compound, see: Tomassini et al. (1994).

Experimental top

Methyl 4'-acetyl-3''-carbamoyl-[1,1':3',1''-terphenyl]-2-carboxylate (2.70 mmol) was dissolved in a mixture of 10 M NaOH (40 ml), 2-propanol (20 ml) and THF (20 ml), which was then refluxed overnight. The reaction mixture was cooled to room temperature, and acidified (pH = 4) with 2 M HCl. After the mixture was extracted with ethyl acetate, the organic layer was washed with water and brine, and dried over anhydrous Na2SO4. Concentration of the organic solution gave the title compound (yield 94%). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an acetone/n-hexane solution of the compound at room temperature.

Refinement top

The hydrogen atoms of phenyl groups were placed in geometrical positions [C–H 0.95 Å, Uiso(H) = 1.2Ueq(C)], and refined using a riding model. Hydrogen atoms of methyl group 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)]. The carbamoyl and carboxyl groups were disordered, and the occupancies of carbamoyl and carboxyl groups were determined to 0.558 (15) for A and 0.442 (15) for B. Hydroxyl hydrogen atoms for both parts, A and B, were found in a difference Fourier map, and a rotating group model was applied with distance constraint [O–H 0.84 Å, Uiso(H) = 1.2Ueq(O)]. The hydrogen atoms of A and B parts of carbamoyl group were placed in geometrical positions [N–H 0.88 Å, Uiso(H) = 1.2Ueq(N)], and refined using a riding model.

Computing details top

Data collection: WinAFC (Rigaku, 1999); cell refinement: WinAFC (Rigaku, 1999); data reduction: WinAFC (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. 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. Disordered atoms are discriminated with A/B notation, and the minor disordered form B is drawn as dashed bonds.
[Figure 2] Fig. 2. A crystal packing view of the title compound. Intermolecular O–H···O and N–H···O hydrogen bonds are represented by dashed lines only for the disordered form A for clarity.
[Figure 3] Fig. 3. A crystal packing view of the title compound represented by a sphere model. Anti-parallel helices align parallel to the b axis. The disordered form B is not shown for clarity.
4'-Acetyl-3''-carbamoyl-[1,1':3',1''-terphenyl]-2-carboxylic acid top
Crystal data top
C22H17NO4F(000) = 752.00
Mr = 359.38Dx = 1.360 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 13.076 (4) Åθ = 16.0–17.4°
b = 20.581 (5) ŵ = 0.09 mm−1
c = 6.725 (3) ÅT = 100 K
β = 104.10 (3)°Plate, colorless
V = 1755.2 (9) Å30.38 × 0.25 × 0.20 mm
Z = 4
Data collection top
Rigaku AFC-7R
diffractometer		θmax = 27.5°
ω scansh = −16→16
4953 measured reflectionsk = 0→26
4026 independent reflectionsl = −8→4
2389 reflections with F2 > 2σ(F2)3 standard reflections every 150 reflections
Rint = 0.014 intensity decay: 0.6%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0495P)2 + 0.6018P]
where P = (Fo2 + 2Fc2)/3
4026 reflections(Δ/σ)max < 0.001
284 parametersΔρmax = 0.23 e Å−3
10 restraintsΔρmin = −0.34 e Å−3
Primary atom site location: structure-invariant direct methods
Crystal data top
C22H17NO4V = 1755.2 (9) Å3
Mr = 359.38Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.076 (4) ŵ = 0.09 mm−1
b = 20.581 (5) ÅT = 100 K
c = 6.725 (3) Å0.38 × 0.25 × 0.20 mm
β = 104.10 (3)°
Data collection top
Rigaku AFC-7R
diffractometer		Rint = 0.014
4953 measured reflections3 standard reflections every 150 reflections
4026 independent reflections intensity decay: 0.6%
2389 reflections with F2 > 2σ(F2)
Refinement top
R[F2 > 2σ(F2)] = 0.05010 restraints
wR(F2) = 0.132H-atom parameters constrained
S = 1.01Δρmax = 0.23 e Å−3
4026 reflectionsΔρmin = −0.34 e Å−3
284 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*/UeqOcc. (<1)
O24A0.7288 (6)0.7406 (4)0.6288 (14)0.053 (4)0.558 (15)
O24B0.6566 (6)0.6441 (4)0.572 (3)0.040 (4)0.442 (15)
O25A0.6540 (7)0.6429 (4)0.558 (3)0.056 (4)0.558 (15)
O25B0.7277 (6)0.7431 (4)0.6298 (14)0.029 (3)0.442 (15)
O260.72444 (13)0.41418 (8)−0.1531 (3)0.0419 (4)
O27A0.5183 (2)0.20108 (10)0.0987 (13)0.0431 (17)0.558 (15)
O27B0.4504 (3)0.29447 (17)0.0312 (17)0.039 (3)0.442 (15)
N23A0.44490 (18)0.30101 (11)0.0760 (13)0.0293 (18)0.558 (15)
N23B0.5187 (3)0.19802 (9)0.1589 (13)0.036 (2)0.442 (15)
C10.87031 (17)0.59106 (10)0.6538 (4)0.0341 (5)
C20.83737 (17)0.64963 (10)0.7265 (4)0.0365 (6)
C30.89855 (19)0.67828 (11)0.9030 (4)0.0433 (6)
C40.9899 (2)0.64923 (12)1.0133 (4)0.0468 (7)
C51.02260 (19)0.59176 (12)0.9444 (4)0.0465 (6)
C60.96413 (18)0.56329 (11)0.7670 (4)0.0411 (6)
C70.81424 (17)0.55911 (10)0.4596 (4)0.0328 (5)
C80.79962 (16)0.49204 (10)0.4560 (4)0.0317 (5)
C90.75198 (16)0.45849 (10)0.2784 (4)0.0310 (5)
C100.71633 (16)0.49374 (10)0.0949 (4)0.0328 (5)
C110.72897 (18)0.56122 (10)0.0999 (4)0.0390 (6)
C120.77824 (17)0.59325 (10)0.2770 (4)0.0372 (6)
C130.73748 (18)0.38695 (10)0.2912 (4)0.0327 (5)
C140.64108 (18)0.35803 (10)0.2106 (4)0.0347 (5)
C150.62910 (19)0.29090 (10)0.2228 (4)0.0371 (6)
C160.7138 (2)0.25265 (10)0.3196 (4)0.0398 (6)
C170.8098 (2)0.28157 (11)0.4053 (4)0.0412 (6)
C180.82187 (19)0.34818 (10)0.3917 (4)0.0362 (6)
C19A0.73405 (18)0.68032 (8)0.6318 (4)0.0383 (6)0.558 (15)
C19B0.73405 (18)0.68032 (8)0.6318 (4)0.0383 (6)0.442 (15)
C200.67702 (18)0.46037 (11)−0.1066 (4)0.0375 (6)
C210.5798 (3)0.48606 (14)−0.2520 (5)0.0591 (8)
C22A0.52595 (15)0.26103 (7)0.1284 (4)0.0404 (6)0.558 (15)
C22B0.52595 (15)0.26103 (7)0.1284 (4)0.0404 (6)0.442 (15)
H30.87710.71860.94840.0520*
H41.02990.66871.13580.0562*
H51.08560.57161.01910.0558*
H60.98820.52390.72070.0493*
H80.82320.46830.57990.0380*
H110.70290.5856−0.02200.0467*
H120.78780.63900.27480.0446*
H140.58230.38410.14630.0417*
H160.70600.20690.32700.0477*
H170.86780.25560.47380.0495*
H180.88820.36760.45130.0434*
H21A0.52050.4843−0.18690.0710*
H21B0.56370.4595−0.37680.0710*
H21C0.59170.5312−0.28740.0710*
H25A0.59930.66560.52140.0676*0.558 (15)
H25B0.66610.75450.57110.0344*0.442 (15)
H23A0.38190.28570.01730.0352*0.558 (15)
H23B0.45380.34290.09990.0352*0.558 (15)
H23C0.45860.17770.10990.0430*0.442 (15)
H23D0.57390.17630.22830.0430*0.442 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O24A0.075 (7)0.026 (5)0.059 (6)0.005 (4)0.016 (5)0.019 (4)
O24B0.021 (5)0.011 (5)0.092 (10)0.005 (4)0.020 (5)0.011 (5)
O25A0.056 (7)0.044 (6)0.072 (7)−0.010 (5)0.022 (5)−0.019 (5)
O25B0.023 (5)0.027 (5)0.036 (6)−0.007 (4)0.007 (4)−0.024 (4)
O260.0500 (10)0.0378 (9)0.0382 (9)−0.0020 (8)0.0114 (8)0.0018 (8)
O27A0.063 (3)0.031 (3)0.051 (4)−0.0162 (18)0.0434 (19)−0.0064 (16)
O27B0.053 (4)0.046 (4)0.018 (5)−0.011 (3)0.008 (3)−0.002 (3)
N23A0.041 (3)0.028 (3)0.019 (4)−0.010 (2)0.008 (2)−0.0085 (18)
N23B0.058 (4)0.029 (3)0.034 (4)−0.017 (3)0.037 (3)−0.004 (2)
C10.0366 (12)0.0280 (11)0.0404 (13)−0.0046 (10)0.0148 (10)0.0007 (10)
C20.0403 (13)0.0293 (12)0.0439 (14)−0.0054 (10)0.0181 (11)0.0012 (10)
C30.0524 (16)0.0336 (13)0.0480 (15)−0.0097 (11)0.0199 (13)−0.0023 (11)
C40.0489 (15)0.0483 (15)0.0432 (14)−0.0182 (13)0.0110 (12)−0.0042 (12)
C50.0377 (14)0.0498 (15)0.0501 (15)−0.0048 (12)0.0074 (12)0.0027 (13)
C60.0383 (13)0.0379 (13)0.0490 (15)0.0003 (11)0.0144 (11)0.0010 (11)
C70.0329 (12)0.0282 (11)0.0403 (13)0.0014 (9)0.0146 (10)0.0002 (10)
C80.0353 (12)0.0265 (11)0.0342 (12)0.0051 (9)0.0104 (10)0.0069 (9)
C90.0330 (12)0.0257 (11)0.0351 (12)0.0027 (9)0.0100 (10)0.0030 (9)
C100.0324 (12)0.0301 (11)0.0356 (12)0.0027 (10)0.0075 (10)0.0072 (10)
C110.0424 (14)0.0328 (12)0.0415 (14)0.0054 (10)0.0098 (11)0.0139 (11)
C120.0414 (13)0.0238 (11)0.0482 (14)0.0016 (10)0.0145 (11)0.0062 (10)
C130.0449 (14)0.0267 (11)0.0272 (11)0.0030 (10)0.0103 (10)0.0038 (9)
C140.0467 (14)0.0303 (11)0.0287 (12)0.0013 (10)0.0121 (10)0.0041 (9)
C150.0552 (15)0.0303 (12)0.0303 (12)−0.0053 (11)0.0193 (11)−0.0022 (10)
C160.0633 (16)0.0244 (11)0.0379 (13)0.0015 (11)0.0243 (12)0.0041 (10)
C170.0580 (16)0.0304 (12)0.0379 (13)0.0096 (11)0.0167 (12)0.0056 (10)
C180.0452 (14)0.0331 (12)0.0300 (12)0.0032 (10)0.0086 (10)0.0027 (10)
C19A0.0482 (15)0.0301 (12)0.0418 (14)0.0008 (11)0.0212 (12)0.0014 (11)
C19B0.0482 (15)0.0301 (12)0.0418 (14)0.0008 (11)0.0212 (12)0.0014 (11)
C200.0422 (13)0.0323 (12)0.0367 (13)−0.0045 (10)0.0073 (11)0.0100 (10)
C210.0612 (18)0.0556 (17)0.0493 (16)0.0034 (14)−0.0085 (14)0.0086 (14)
C22A0.0607 (16)0.0354 (13)0.0330 (13)−0.0072 (12)0.0267 (12)−0.0012 (11)
C22B0.0607 (16)0.0354 (13)0.0330 (13)−0.0072 (12)0.0267 (12)−0.0012 (11)
Geometric parameters (Å, º) top
O24A—C19A1.242 (8)C14—C151.395 (3)
O24B—C19B1.243 (8)C15—C161.385 (4)
O25A—C19A1.296 (9)C15—C22A1.478 (3)
O25B—C19B1.295 (8)C15—C22B1.478 (3)
O26—C201.217 (3)C16—C171.382 (4)
O27A—C22A1.250 (3)C17—C181.386 (3)
O27B—C22B1.250 (6)C20—C211.498 (4)
N23A—C22A1.320 (3)O25A—H25A0.840
N23B—C22B1.320 (3)O25B—H25B0.840
C1—C21.407 (4)N23A—H23A0.880
C1—C61.399 (3)N23A—H23B0.880
C1—C71.486 (3)N23B—H23C0.880
C2—C31.390 (3)N23B—H23D0.880
C2—C19A1.487 (3)C3—H30.950
C2—C19B1.487 (3)C4—H40.950
C3—C41.379 (4)C5—H50.950
C4—C51.376 (4)C6—H60.950
C5—C61.381 (4)C8—H80.950
C7—C81.393 (3)C11—H110.950
C7—C121.393 (3)C12—H120.950
C8—C91.389 (3)C14—H140.950
C9—C101.409 (3)C16—H160.950
C9—C131.490 (3)C17—H170.950
C10—C111.398 (3)C18—H180.950
C10—C201.494 (3)C21—H21A0.980
C11—C121.376 (3)C21—H21B0.980
C13—C141.380 (3)C21—H21C0.980
C13—C181.396 (3)
O24A···C13.574 (8)N23B···H14ix3.5997
O24A···C32.824 (8)N23B···H21Bix3.3147
O24B···C12.924 (8)N23B···H25Bviii2.7850
O24B···C33.468 (10)N23B···H25Biv3.4966
O24B···C72.939 (11)C1···H11x3.4469
O24B···C123.016 (15)C1···H18vi3.5052
O25A···C12.943 (9)C2···H3i3.4055
O25A···C33.537 (10)C2···H11x3.0228
O25A···C72.913 (11)C3···H11x3.3268
O25A···C122.960 (14)C3···H12x3.2816
O25B···C32.854 (8)C3···H17xiii3.3647
O26···C92.979 (3)C4···H12x3.5193
O26···C113.465 (3)C4···H17xiii2.8615
O26···C133.003 (3)C4···H18xiv3.5814
O26···C143.131 (3)C5···H6xiv3.3034
O27A···C162.831 (5)C5···H8xiv3.5616
O27B···C142.814 (5)C5···H18vi3.2642
N23A···C142.765 (4)C6···H5xiv3.2642
N23B···C162.756 (4)C6···H18vi3.0479
C1···C42.807 (4)C7···H6vi3.5474
C2···C52.775 (4)C8···H6vi3.2895
C2···C123.153 (4)C8···H21Bx3.5940
C3···C62.749 (4)C9···H5vi3.3115
C6···C82.993 (3)C9···H6vi3.4150
C7···C102.817 (3)C10···H5vi3.1732
C7···C19A3.042 (3)C10···H21Axii3.3333
C7···C19B3.042 (3)C11···H21Axii3.5766
C8···C112.746 (4)C11···H23Axii3.4767
C8···C183.017 (3)C11···H23Bxii3.1379
C9···C122.795 (3)C12···H25Bi3.5920
C10···C143.122 (3)C12···H23Axii3.5335
C11···C213.090 (4)C13···H5vi3.5754
C12···C19A3.148 (4)C14···H16v3.1983
C12···C19B3.148 (4)C14···H23Dv3.2254
C13···C162.793 (3)C15···H16v3.0667
C13···C203.006 (4)C15···H23Dv3.2963
C14···C172.766 (4)C16···H16v3.3930
C14···C203.114 (4)C16···H16ix3.5377
C15···C182.764 (4)C16···H17v3.4310
O24A···O24Ai3.385 (14)C17···H4xv3.1856
O24A···O24Aii3.385 (14)C17···H4xiv3.4373
O24A···O27Aiii3.322 (8)C17···H16ix3.4376
O24A···N23Aiii2.661 (8)C17···H17v3.2638
O24A···N23Aiv3.468 (12)C18···H4xiv3.3127
O24A···C3i3.415 (10)C19A···H3i3.2358
O24A···C12ii3.576 (8)C19A···H11x3.1387
O24A···C22Aiii3.385 (8)C19A···H23Aiii2.6965
O24B···O27Biii3.398 (8)C19A···H23Aiv3.1779
O24B···O27Biv3.535 (19)C19A···H23Biv3.4180
O24B···N23Biii2.677 (10)C19B···H3i3.2358
O24B···C22Biii3.427 (8)C19B···H11x3.1387
O25A···O27Aiii2.544 (9)C19B···H25Bii3.5495
O25A···N23Aiii3.537 (8)C19B···H23Ciii2.6448
O25A···N23Aiv3.255 (17)C20···H5vi3.0855
O25A···C22Aiii3.404 (8)C20···H8vii3.1757
O25B···O25Bi3.374 (14)C20···H16v3.5037
O25B···O25Bii3.374 (14)C20···H23Dv3.1993
O25B···O27Biii2.546 (8)C21···H14xii3.5891
O25B···N23Biii3.459 (8)C21···H21Axii3.5627
O25B···C3i3.404 (9)C21···H21Bxi2.9537
O25B···C12ii3.527 (8)C21···H21Cxi3.3709
O25B···C22Biii3.369 (7)C21···H23Dv3.3449
O26···N23Bv3.537 (4)C22A···H16v3.5231
O26···C5vi3.265 (3)C22A···H25Aviii2.5981
O26···C8vii3.421 (3)C22A···H25Aiv3.5196
O26···C16v3.439 (3)C22B···H16v3.5231
O27A···O24Aviii3.322 (8)C22B···H25Bviii2.5455
O27A···O25Aviii2.544 (9)C22B···H23Dv3.1807
O27A···N23Av3.410 (12)H3···O24Aii2.6611
O27A···N23Aix3.568 (12)H3···O25Bii2.6611
O27A···C14v3.592 (8)H3···C2ii3.4055
O27A···C15v3.209 (9)H3···C19Aii3.2358
O27A···C19Aviii3.314 (4)H3···C19Bii3.2358
O27A···C22Av3.282 (9)H3···H11x3.5974
O27B···O24Bviii3.398 (8)H3···H12x3.1803
O27B···O24Biv3.535 (19)H3···H12ii3.2642
O27B···O25Bviii2.546 (8)H3···H17xiii3.3367
O27B···N23Bv2.860 (14)H3···H25Bii3.1162
O27B···C19Bviii3.354 (5)H3···H23Aiv3.4509
O27B···C22Bv3.305 (11)H4···C17xiii3.1856
N23A···O24Aviii2.661 (8)H4···C17xiv3.4373
N23A···O24Aiv3.468 (12)H4···C18xiv3.3127
N23A···O25Aviii3.537 (8)H4···H12x3.5653
N23A···O25Aiv3.255 (17)H4···H16xiii3.4913
N23A···O27Av3.568 (12)H4···H17xiii2.4525
N23A···O27Aix3.410 (12)H4···H17xiv3.0649
N23A···C19Aviii3.465 (4)H4···H18xiv2.8227
N23A···C19Aiv3.424 (8)H5···O26vi2.4442
N23B···O24Bviii2.677 (10)H5···C6xiv3.2642
N23B···O25Bviii3.459 (8)H5···C9vi3.3115
N23B···O26ix3.537 (4)H5···C10vi3.1732
N23B···O27Bix2.860 (14)H5···C13vi3.5754
N23B···C15v3.577 (9)H5···C20vi3.0855
N23B···C19Bviii3.424 (5)H5···H6xiv2.9459
N23B···C22Bix3.247 (9)H5···H8xiv2.7928
C3···O24Aii3.415 (10)H5···H18vi3.4956
C3···O25Bii3.404 (9)H6···C5xiv3.3034
C5···O26vi3.265 (3)H6···C7vi3.5474
C8···O26x3.421 (3)H6···C8vi3.2895
C12···O24Ai3.576 (8)H6···C9vi3.4150
C12···O25Bi3.527 (8)H6···H5xiv2.9459
C14···O27Aix3.592 (8)H6···H6vi3.2114
C15···O27Aix3.209 (9)H6···H8vi3.5529
C15···N23Bix3.577 (9)H6···H18vi3.1384
C15···C16v3.294 (4)H8···O26x2.6948
C15···C22Aix3.492 (4)H8···C5xiv3.5616
C15···C22Bix3.492 (4)H8···C20x3.1757
C16···O26ix3.439 (3)H8···H5xiv2.7928
C16···C15ix3.294 (4)H8···H6vi3.5529
C16···C16v3.364 (4)H8···H21Bx3.4797
C16···C16ix3.364 (4)H8···H21Cx3.5978
C16···C17v3.397 (4)H11···O24Bvii2.9092
C16···C22Aix3.594 (4)H11···O25Avii2.9801
C16···C22Bix3.594 (4)H11···O27Bxii3.1717
C17···C16ix3.397 (4)H11···N23Axii2.9961
C19A···O27Aiii3.314 (4)H11···C1vii3.4469
C19A···N23Aiii3.465 (4)H11···C2vii3.0228
C19A···N23Aiv3.424 (8)H11···C3vii3.3268
C19B···O27Biii3.354 (5)H11···C19Avii3.1387
C19B···N23Biii3.424 (5)H11···C19Bvii3.1387
C21···C21xi3.524 (4)H11···H3vii3.5974
C22A···O24Aviii3.385 (8)H11···H25Avii3.4568
C22A···O25Aviii3.404 (8)H11···H25Bi3.4075
C22A···O27Aix3.282 (9)H11···H23Axii2.8749
C22A···C15v3.492 (4)H11···H23Bxii2.4740
C22A···C16v3.594 (4)H12···O24Ai2.7077
C22A···C22Av3.393 (4)H12···O25Bi2.6608
C22A···C22Aix3.393 (4)H12···O27Bxii3.5614
C22B···O24Bviii3.427 (8)H12···N23Axii3.5845
C22B···O25Bviii3.369 (7)H12···C3vii3.2816
C22B···O27Bix3.305 (11)H12···C4vii3.5193
C22B···N23Bv3.247 (9)H12···H3vii3.1803
C22B···C15v3.492 (4)H12···H3i3.2642
C22B···C16v3.594 (4)H12···H4vii3.5653
C22B···C22Bv3.393 (4)H12···H25Bi2.8558
C22B···C22Bix3.393 (4)H12···H23Axii3.0095
O24A···H32.5591H12···H23Bxii3.5480
O24A···H123.3956H12···H23Ciii3.5825
O24A···H25A2.2753H14···N23Bv3.5997
O24B···H122.9356H14···C21xii3.5891
O24B···H25B2.2756H14···H16v3.5243
O25A···H122.8862H14···H21Axii3.0664
O25B···H32.5728H14···H21Cxii3.1902
O25B···H123.4386H14···H23Dv3.0506
O26···H143.1162H16···O26ix2.5039
O26···H21A2.9916H16···C14ix3.1983
O26···H21B2.4516H16···C15ix3.0667
O26···H21C2.9767H16···C16v3.5377
O27A···H162.5604H16···C16ix3.3930
O27A···H23A2.4581H16···C17v3.4376
O27A···H23B3.0392H16···C20ix3.5037
O27B···H142.5151H16···C22Aix3.5231
O27B···H23C2.4575H16···C22Bix3.5231
O27B···H23D3.0390H16···H4xv3.4913
N23A···H142.4416H16···H14ix3.5243
N23B···H162.4411H17···C3xv3.3647
C1···H33.2766H17···C4xv2.8615
C1···H53.2792H17···C16ix3.4310
C1···H82.6189H17···C17ix3.2638
C1···H122.7007H17···H3xv3.3367
C2···H43.2692H17···H4xv2.4525
C2···H63.2603H17···H4xiv3.0649
C2···H122.9560H17···H17v3.3703
C2···H25A3.0999H17···H17ix3.3703
C2···H25B3.1025H18···C1vi3.5052
C3···H53.2381H18···C4xiv3.5814
C4···H63.2418H18···C5vi3.2642
C5···H33.2344H18···C6vi3.0479
C6···H43.2495H18···H4xiv2.8227
C6···H82.7695H18···H5vi3.4956
C7···H62.6147H18···H6vi3.1384
C7···H113.2568H21A···C10xii3.3333
C8···H62.7458H21A···C11xii3.5766
C8···H123.2501H21A···C21xii3.5627
C8···H182.8136H21A···H14xii3.0664
C9···H113.2713H21A···H21Axii2.7717
C9···H142.6638H21A···H21Bxi3.0955
C9···H182.6478H21A···H21Cxi3.4959
C10···H83.2622H21A···H23Dv3.4547
C10···H123.2741H21B···O24Bxii3.5677
C10···H142.9289H21B···O25Axii3.5143
C10···H21A2.7967H21B···O27Av3.3553
C10···H21B3.3846H21B···N23Bv3.3147
C10···H21C2.7960H21B···C8vii3.5940
C11···H21A3.3309H21B···C21xi2.9537
C11···H21C2.8476H21B···H8vii3.4797
C12···H83.2438H21B···H21Axi3.0955
C12···H25A3.5025H21B···H21Bxi2.6366
C13···H82.6019H21B···H21Cxi2.6513
C13···H173.2704H21B···H25Axii3.3333
C14···H163.2687H21B···H23Cv3.1327
C14···H183.2477H21B···H23Dv2.8792
C14···H23B2.3993H21C···O24Bvii2.7212
C15···H173.2482H21C···O25Avii2.7275
C15···H23A3.1925H21C···C21xi3.3709
C15···H23B2.4815H21C···H8vii3.5978
C15···H23C3.1858H21C···H14xii3.1902
C15···H23D2.4688H21C···H21Axi3.4959
C16···H143.2640H21C···H21Bxi2.6513
C16···H183.2552H21C···H21Cxi3.4970
C16···H23D2.3755H21C···H25Avii3.0628
C18···H82.7759H21C···H23Bxii3.0047
C18···H143.2497H25A···O27Aiii1.7163
C18···H163.2589H25A···N23Aiii2.8889
C19A···H32.5904H25A···N23Aiv2.9827
C19A···H122.7932H25A···C22Aiii2.5981
C19B···H32.5904H25A···C22Aiv3.5196
C19B···H122.7932H25A···H11x3.4568
C20···H112.6426H25A···H21Bxii3.3333
C20···H142.8136H25A···H21Cx3.0628
C21···H112.8220H25A···H23Aiii2.5047
C21···H143.3967H25A···H23Aiv3.2114
C22A···H142.6320H25A···H23Biv2.8039
C22A···H162.6522H25B···O25Bi3.2598
C22B···H142.6320H25B···O27Biii1.7200
C22B···H162.6522H25B···O27Biv3.5315
H3···H42.3252H25B···N23Biii2.7850
H3···H25B3.3443H25B···N23Biv3.4966
H4···H52.3286H25B···C12ii3.5920
H5···H62.3172H25B···C19Bi3.5495
H6···H82.4218H25B···C22Biii2.5455
H8···H182.4745H25B···H3i3.1162
H11···H122.3115H25B···H11ii3.4075
H11···H21A3.1583H25B···H12ii2.8558
H11···H21C2.2998H25B···H25Bi3.3673
H12···H25A3.3341H25B···H25Bii3.3673
H14···H21A3.0075H25B···H23Ciii2.3807
H14···H23A3.2571H25B···H23Civ3.3038
H14···H23B1.8390H23A···O24Aviii1.7981
H16···H172.3329H23A···O24Aiv3.1195
H16···H23C3.2639H23A···O25Aviii3.0009
H16···H23D1.8052H23A···O25Aiv3.3417
H17···H182.3289H23A···C11xii3.4767
O24A···H3i2.6611H23A···C12xii3.5335
O24A···H12ii2.7077H23A···C19Aviii2.6965
O24A···H23Aiii1.7981H23A···C19Aiv3.1779
O24A···H23Aiv3.1195H23A···H3iv3.4509
O24A···H23Biii3.2737H23A···H11xii2.8749
O24B···H11x2.9092H23A···H12xii3.0095
O24B···H21Bxii3.5677H23A···H25Aviii2.5047
O24B···H21Cx2.7212H23A···H25Aiv3.2114
O24B···H23Ciii1.8297H23B···O24Aviii3.2737
O24B···H23Diii3.2621H23B···O25Aiv2.9887
O25A···H11x2.9801H23B···O27Aix3.3768
O25A···H21Bxii3.5143H23B···C11xii3.1379
O25A···H21Cx2.7275H23B···C19Aiv3.4180
O25A···H23Aiii3.0009H23B···H11xii2.4740
O25A···H23Aiv3.3417H23B···H12xii3.5480
O25A···H23Biv2.9887H23B···H21Cxii3.0047
O25B···H3i2.6611H23B···H25Aiv2.8039
O25B···H12ii2.6608H23C···O24Bviii1.8297
O25B···H25Bii3.2598H23C···O25Bviii2.9043
O25B···H23Ciii2.9043H23C···O27Bix2.9182
O26···H5vi2.4442H23C···C19Bviii2.6448
O26···H8vii2.6948H23C···H12viii3.5825
O26···H16v2.5039H23C···H21Bix3.1327
O26···H23Dv2.6860H23C···H25Bviii2.3807
O27A···H21Bix3.3553H23C···H25Biv3.3038
O27A···H25Aviii1.7163H23D···O24Bviii3.2621
O27A···H23Bv3.3768H23D···O26ix2.6860
O27B···H11xii3.1717H23D···O27Bix2.9533
O27B···H12xii3.5614H23D···C14ix3.2254
O27B···H25Bviii1.7200H23D···C15ix3.2963
O27B···H25Biv3.5315H23D···C20ix3.1993
O27B···H23Cv2.9182H23D···C21ix3.3449
O27B···H23Dv2.9533H23D···C22Bix3.1807
N23A···H11xii2.9961H23D···H14ix3.0506
N23A···H12xii3.5845H23D···H21Aix3.4547
N23A···H25Aviii2.8889H23D···H21Bix2.8792
N23A···H25Aiv2.9827
C2—C1—C6117.59 (19)C10—C20—C21118.6 (2)
C2—C1—C7123.86 (19)O27A—C22A—N23A123.0 (3)
C6—C1—C7118.5 (2)O27A—C22A—C15120.5 (2)
C1—C2—C3119.9 (2)N23A—C22A—C15116.41 (18)
C1—C2—C19A122.55 (18)O27B—C22B—N23B123.0 (3)
C1—C2—C19B122.55 (18)O27B—C22B—C15121.2 (3)
C3—C2—C19A117.3 (2)N23B—C22B—C15115.8 (3)
C3—C2—C19B117.3 (2)C19A—O25A—H25A109.468
C2—C3—C4121.2 (3)C19B—O25B—H25B109.472
C3—C4—C5119.4 (3)C22A—N23A—H23A119.991
C4—C5—C6120.2 (3)C22A—N23A—H23B119.999
C1—C6—C5121.6 (3)H23A—N23A—H23B120.010
C1—C7—C8119.34 (19)C22B—N23B—H23C120.003
C1—C7—C12122.66 (19)C22B—N23B—H23D119.996
C8—C7—C12117.97 (19)H23C—N23B—H23D120.001
C7—C8—C9122.6 (2)C2—C3—H3119.404
C8—C9—C10118.71 (19)C4—C3—H3119.397
C8—C9—C13118.60 (19)C3—C4—H4120.310
C10—C9—C13122.65 (18)C5—C4—H4120.297
C9—C10—C11118.59 (19)C4—C5—H5119.883
C9—C10—C20121.66 (19)C6—C5—H5119.871
C11—C10—C20119.4 (2)C1—C6—H6119.186
C10—C11—C12121.6 (2)C5—C6—H6119.188
C7—C12—C11120.5 (2)C7—C8—H8118.701
C9—C13—C14121.38 (19)C9—C8—H8118.708
C9—C13—C18119.75 (19)C10—C11—H11119.201
C14—C13—C18118.8 (2)C12—C11—H11119.198
C13—C14—C15120.6 (2)C7—C12—H12119.750
C14—C15—C16120.1 (2)C11—C12—H12119.749
C14—C15—C22A119.38 (19)C13—C14—H14119.694
C14—C15—C22B119.38 (19)C15—C14—H14119.708
C16—C15—C22A120.48 (18)C15—C16—H16120.253
C16—C15—C22B120.48 (18)C17—C16—H16120.260
C15—C16—C17119.5 (2)C16—C17—H17119.827
C16—C17—C18120.4 (2)C18—C17—H17119.822
C13—C18—C17120.5 (2)C13—C18—H18119.731
O24A—C19A—O25A123.5 (5)C17—C18—H18119.720
O24A—C19A—C2118.1 (4)C20—C21—H21A109.468
O25A—C19A—C2118.4 (4)C20—C21—H21B109.469
O24B—C19B—O25B123.4 (5)C20—C21—H21C109.470
O24B—C19B—C2117.8 (4)H21A—C21—H21B109.473
O25B—C19B—C2118.5 (4)H21A—C21—H21C109.473
O26—C20—C10120.51 (19)H21B—C21—H21C109.475
O26—C20—C21120.8 (2)
H25A—O25A—C19A—O24A−5.5H8—C8—C9—C131.5
H25A—O25A—C19A—C2173.8C8—C9—C10—C11−1.0 (3)
H25B—O25B—C19B—O24B−6.2C8—C9—C10—C20172.06 (19)
H25B—O25B—C19B—C2179.2C8—C9—C13—C14129.7 (2)
H23A—N23A—C22A—O27A0.0C8—C9—C13—C18−48.4 (3)
H23A—N23A—C22A—C15179.0C10—C9—C13—C14−48.3 (4)
H23B—N23A—C22A—O27A−180.0C10—C9—C13—C18133.6 (2)
H23B—N23A—C22A—C15−1.0C13—C9—C10—C11176.98 (19)
H23C—N23B—C22B—O27B−0.0C13—C9—C10—C20−10.0 (4)
H23C—N23B—C22B—C15178.0C9—C10—C11—C122.2 (4)
H23D—N23B—C22B—O27B180.0C9—C10—C11—H11−177.8
H23D—N23B—C22B—C15−2.0C9—C10—C20—O26−44.3 (4)
C2—C1—C6—C50.3 (4)C9—C10—C20—C21137.2 (2)
C2—C1—C6—H6−179.7C11—C10—C20—O26128.6 (3)
C6—C1—C2—C31.1 (4)C11—C10—C20—C21−49.8 (3)
C6—C1—C2—C19A−173.7 (2)C20—C10—C11—C12−170.9 (2)
C6—C1—C2—C19B−173.7 (2)C20—C10—C11—H119.0
C2—C1—C7—C8−137.0 (3)C10—C11—C12—C7−2.1 (4)
C2—C1—C7—C1245.2 (4)C10—C11—C12—H12177.9
C7—C1—C2—C3−175.7 (2)H11—C11—C12—C7177.9
C7—C1—C2—C19A9.4 (4)H11—C11—C12—H12−2.0
C7—C1—C2—C19B9.4 (4)C9—C13—C14—C15179.61 (19)
C6—C1—C7—C846.2 (4)C9—C13—C14—H14−0.4
C6—C1—C7—C12−131.6 (3)C9—C13—C18—C17179.93 (19)
C7—C1—C6—C5177.3 (2)C9—C13—C18—H18−0.1
C7—C1—C6—H6−2.7C14—C13—C18—C171.8 (4)
C1—C2—C3—C4−2.2 (4)C14—C13—C18—H18−178.2
C1—C2—C3—H3177.8C18—C13—C14—C15−2.3 (4)
C1—C2—C19A—O24A−146.0 (3)C18—C13—C14—H14177.7
C1—C2—C19A—O25A34.7 (4)C13—C14—C15—C161.1 (4)
C1—C2—C19B—O24B38.5 (4)C13—C14—C15—C22A−177.7 (2)
C1—C2—C19B—O25B−146.6 (3)C13—C14—C15—C22B−177.7 (2)
C3—C2—C19A—O24A39.0 (4)H14—C14—C15—C16−178.9
C3—C2—C19A—O25A−140.3 (3)H14—C14—C15—C22A2.3
C19A—C2—C3—C4172.9 (2)H14—C14—C15—C22B2.3
C19A—C2—C3—H3−7.1C14—C15—C16—C170.6 (4)
C3—C2—C19B—O24B−136.5 (3)C14—C15—C16—H16−179.4
C3—C2—C19B—O25B38.4 (4)C14—C15—C22A—O27A164.9 (2)
C19B—C2—C3—C4172.9 (2)C14—C15—C22A—N23A−14.1 (4)
C19B—C2—C3—H3−7.1C14—C15—C22B—O27B2.7 (4)
C2—C3—C4—C51.8 (4)C14—C15—C22B—N23B−175.4 (2)
C2—C3—C4—H4−178.2C16—C15—C22A—O27A−14.0 (4)
H3—C3—C4—C5−178.2C16—C15—C22A—N23A167.0 (2)
H3—C3—C4—H41.8C22A—C15—C16—C17179.4 (2)
C3—C4—C5—C6−0.4 (4)C22A—C15—C16—H16−0.6
C3—C4—C5—H5179.6C16—C15—C22B—O27B−176.1 (3)
H4—C4—C5—C6179.6C16—C15—C22B—N23B5.8 (4)
H4—C4—C5—H5−0.4C22B—C15—C16—C17179.4 (2)
C4—C5—C6—C1−0.7 (4)C22B—C15—C16—H16−0.6
C4—C5—C6—H6179.3C15—C16—C17—C18−1.1 (4)
H5—C5—C6—C1179.3C15—C16—C17—H17178.9
H5—C5—C6—H6−0.7H16—C16—C17—C18178.9
C1—C7—C8—C9−177.22 (19)H16—C16—C17—H17−1.1
C1—C7—C8—H82.8C16—C17—C18—C13−0.1 (4)
C1—C7—C12—C11178.4 (2)C16—C17—C18—H18179.9
C1—C7—C12—H12−1.6H17—C17—C18—C13179.9
C8—C7—C12—C110.6 (4)H17—C17—C18—H18−0.1
C8—C7—C12—H12−179.4O26—C20—C21—H21A121.5
C12—C7—C8—C90.7 (4)O26—C20—C21—H21B1.5
C12—C7—C8—H8−179.3O26—C20—C21—H21C−118.5
C7—C8—C9—C10−0.5 (4)C10—C20—C21—H21A−60.1
C7—C8—C9—C13−178.49 (19)C10—C20—C21—H21B179.9
H8—C8—C9—C10179.5C10—C20—C21—H21C59.9
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+3/2, z+1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) −x+1, −y+1, −z+1; (v) x, −y+1/2, z−1/2; (vi) −x+2, −y+1, −z+1; (vii) x, y, z−1; (viii) −x+1, y−1/2, −z+1/2; (ix) x, −y+1/2, z+1/2; (x) x, y, z+1; (xi) −x+1, −y+1, −z−1; (xii) −x+1, −y+1, −z; (xiii) −x+2, y+1/2, −z+3/2; (xiv) −x+2, −y+1, −z+2; (xv) −x+2, y−1/2, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O25A—H25A···O27Aiii0.841.722.544 (9)168
O25B—H25B···O27Biii0.841.722.546 (8)167
N23A—H23A···O24Aviii0.881.802.661 (8)166
N23B—H23C···O24Bviii0.881.832.667 (10)161
Symmetry codes: (iii) −x+1, y+1/2, −z+1/2; (viii) −x+1, y−1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O25A—H25A···O27Ai0.841.722.544 (9)167.78
O25B—H25B···O27Bi0.841.722.546 (8)167.35
N23A—H23A···O24Aii0.881.802.661 (8)166.13
N23B—H23C···O24Bii0.881.832.667 (10)160.89
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2.
 

Acknowledgements

This work was partly supported by Grants-in-Aid (No. 24590141 to YI) for Scientific Research from the Japan Society for the Promotion of Science. We acknowledge the University of Shizuoka for instrumental support.

References

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ISSN: 2056-9890
Volume 69| Part 10| October 2013| Page o1596
doi:10.1107/S1600536813026482
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