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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 70| Part 6| June 2014| Page o719
doi:10.1107/S1600536814011854

Ethyl 8-meth­­oxy-4-oxo-1,4-di­hydro­quinoline-3-carboxyl­ate

Yoshinobu Ishikawaa* and Nanako Yoshidaa

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 10 April 2014; accepted 21 May 2014; online 31 May 2014)

In the title compound, C13H13NO4, the asymmetric unit contains four independent mol­ecules, each exhibiting an intra­molecular N—H⋯O hydrogen bond. The ethyl group in one of the four mol­ecules is disordered, with a refined occupancy ratio of 0.295 (16):0.705 (16). A face-to-face stacking inter­action is found between the benzene rings of the quinoline units of two of the mol­ecules [centroid–centroid distance = 3.541 (2) Å], which are sandwiched by the other two mol­ecules through N—H⋯O hydrogen bonding. In the crystal, the sandwiched mol­ecules are assembled via stacking inter­actions along the b-axis direction with their translation-symmetry equivalents [centroid–centroid distance = 3.529 (2) Å], and are further linked through N—H⋯O hydrogen bonding. The other two mol­ecules are linked via stacking inter­actions with their inversion-symmetry equivalents [centroid–centroid distances = 3.512 (3) and 3.716 (4) Å] and via N—H⋯O hydrogen bonding.

CCDC reference: 1004530

Related literature

For the background of this study, see: Ishikawa & Fujii (2011[Ishikawa, Y. & Fujii, S. (2011). Bioinformation, 6, 221-225.]). For the synthesis of the title compound, see: Ozeki et al. (1987[Ozeki, K., Ishizuka, Y., Sawada, M., Ichikawa, T., Sato, M. & Yaginuma, H. (1987). Yakugaku Zasshi, 107, 123-134.]).

[Scheme 1]

Experimental

Crystal data

  • C13H13NO4

  • Mr = 247.25

  • Monoclinic, P 21 /c

  • a = 26.32 (3) Å

  • b = 7.0628 (15) Å

  • c = 25.305 (16) Å

  • β = 102.24 (6)°

  • V = 4598 (5) Å3

  • Z = 16

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 100 K

  • 0.40 × 0.23 × 0.13 mm
Data collection

  • Rigaku AFC-7R diffractometer

  • 12488 measured reflections

  • 10546 independent reflections

  • 5412 reflections with F2 > 2σ(F2)

  • Rint = 0.040

  • 3 standard reflections every 150 reflections intensity decay: 6.7%
Refinement

  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.130

  • S = 0.99

  • 10546 reflections

  • 677 parameters

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯O2 0.88 2.33 2.665 (3) 103
N1—H1A⋯O5 0.88 1.93 2.729 (3) 151
N2—H2⋯O3i 0.88 2.19 2.873 (3) 134
N2—H2⋯O6 0.88 2.31 2.656 (4) 103
N3—H3⋯O10 0.88 2.35 2.685 (3) 103
N3—H3⋯O13ii 0.88 2.21 2.857 (4) 130
N3—H3⋯O15ii 0.88 2.26 2.898 (3) 129
N4—H4A⋯O9 0.88 2.03 2.716 (3) 134
N4—H4A⋯O14 0.88 2.31 2.652 (3) 103
Symmetry codes: (i) [x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [x, -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: 1004530

Crystal structure: contains datablocks General, I. DOI: 10.1107/S1600536814011854/rn2125sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814011854/rn2125Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814011854/rn2125Isup3.cml

checkCIF report


Comment top

4-Quinolones show inhibition not only to Gram negative and Gram positive bacteria, but also to human immunodeficiency virus (HIV). The inhibition to HIV is derived from their chelating ability to metal ions in the active site of the metalloenzyme HIV integrase. According to our inhibitor design targeting the metalloenzyme influenza virus RNA polymerase (Ishikawa & Fujii, 2011), we synthesized the title compound as an intermediate of final products.

The asymmetric unit contains four independent molecules with intramolecular N–H···O hydrogen bonding, and the ethyl group in one of the four molecules is disordered with a refined occupancy ratio of 0.295 (16):0.705 (16), as shown in Fig.1. A face-to-face stacking interaction is found between the benzene rings of the quinoline units of the two molecules [centroid–centroid distances = 3.541 (2) Å], which are sandwiched by the other two molecules through intermolecular N–H···O hydrogen bonding.

In the crystal, the sandwiched molecules are assembled via stacking interaction along the b-axis direction with the translation-symmetry equivalentsi,ii [centroid-centroid distances between the benzene rings of the quinoline units = 3.529 (2) Å, i: x, y + 1, z, ii: x, y–1, z], and are further linked with the glide-reflection-symmetry equivalents through N–H···O hydrogen bonding. The other two molecules are also linked with the inversion-symmetry equivalentsiii,iv via stacking interactions [centroid-centroid distances between the benzene rings of the quinoline units = 3.512 (3) and 3.716 (4) Å, iii: –x + 1, –y + 1, –z, iv: –x + 2, –y–1, –z + 1], and with the glide-reflection-symmetry equivalents via N–H···O hydrogen bonding, as shown in Fig.2. A l l 1,3-diketones and secondary amines of the molecules are involved in the intermolecular hydrogen bonding, which leads to a higher order network.

Related literature top

For the background of this study, see: Ishikawa & Fujii (2011). For the synthesis of the title compound, see: Ozeki et al. (1987).

Experimental top

The title compound was synthesized according to the literature (Ozeki et al. 1987). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an acetonitrile solution of the compound at room temperature.

Refinement top

The hydrogen atoms of secondary amine [N–H 0.88 Å, Uiso(H) = 1.2Ueq(N)], methylene [C–H = 0.99 Å, Uiso(H) = 1.2Ueq(C)], and phenyl groups [C–H 0.95 Å, Uiso(H) = 1.2Ueq(C)] were placed in geometrical positions, and refined using a riding model. A rotating group model was applied with a distance constraint for the hydrogen atoms of methyl groups [C–H = 0.98 Å, Uiso(H) = 1.2Ueq(C)]. The ethyl group was disordered and the relative occupancies of the two orientations were refined to 0.295 (16) and 0.705 (16).

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 radii. Intermolecular hydrogen bonds are represented as dashed lines.
[Figure 2] Fig. 2. A crystal packing view of the title compound. Intermolecular hydrogen bonds are represented as dashed lines.
Ethyl 8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate top
Crystal data top
C13H13NO4F(000) = 2080.00
Mr = 247.25Dx = 1.429 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 4 reflections
a = 26.32 (3) Åθ = 16.5–16.7°
b = 7.0628 (15) ŵ = 0.11 mm−1
c = 25.305 (16) ÅT = 100 K
β = 102.24 (6)°Plate, colorless
V = 4598 (5) Å30.40 × 0.23 × 0.13 mm
Z = 16
Data collection top
Rigaku AFC-7R
diffractometer		θmax = 27.5°
ω scansh = −19→34
12488 measured reflectionsk = 0→9
10546 independent reflectionsl = −32→32
5412 reflections with F2 > 2σ(F2)3 standard reflections every 150 reflections
Rint = 0.040 intensity decay: 6.7%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0467P)2]
where P = (Fo2 + 2Fc2)/3
10546 reflections(Δ/σ)max < 0.001
677 parametersΔρmax = 0.32 e Å−3
0 restraintsΔρmin = −0.31 e Å−3
Primary atom site location: structure-invariant direct methods
Crystal data top
C13H13NO4V = 4598 (5) Å3
Mr = 247.25Z = 16
Monoclinic, P21/cMo Kα radiation
a = 26.32 (3) ŵ = 0.11 mm−1
b = 7.0628 (15) ÅT = 100 K
c = 25.305 (16) Å0.40 × 0.23 × 0.13 mm
β = 102.24 (6)°
Data collection top
Rigaku AFC-7R
diffractometer		Rint = 0.040
12488 measured reflections3 standard reflections every 150 reflections
10546 independent reflections intensity decay: 6.7%
5412 reflections with F2 > 2σ(F2)
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.130H-atom parameters constrained
S = 0.99Δρmax = 0.32 e Å−3
10546 reflectionsΔρmin = −0.31 e Å−3
677 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)
O10.90402 (9)−0.3789 (3)0.63683 (7)0.0463 (6)
O20.91957 (6)−0.4270 (3)0.40622 (6)0.0248 (5)
O30.83651 (8)−0.0767 (3)0.64383 (7)0.0383 (6)
O40.83284 (8)0.1380 (3)0.57824 (7)0.0376 (5)
O50.86082 (7)−0.0095 (3)0.38683 (6)0.0252 (5)
O60.73179 (6)−0.2342 (3)0.17433 (6)0.0258 (5)
O70.96521 (7)0.0186 (3)0.37428 (7)0.0309 (5)
O80.97691 (6)−0.0932 (3)0.29473 (6)0.0270 (5)
O90.66478 (7)0.2109 (3)0.15921 (6)0.0290 (5)
O100.74812 (6)0.3555 (3)0.39298 (6)0.0277 (5)
O110.56330 (7)0.0661 (3)0.14972 (7)0.0307 (5)
O120.52678 (6)0.1701 (3)0.21704 (6)0.0260 (5)
O130.60894 (7)0.3565 (3)−0.10036 (6)0.0287 (5)
O140.56294 (7)0.4991 (3)0.11598 (6)0.0256 (5)
O150.63913 (7)−0.0263 (3)−0.10040 (6)0.0279 (5)
O160.67734 (6)−0.1264 (3)−0.01723 (6)0.0253 (5)
N10.89152 (8)−0.2074 (3)0.48081 (8)0.0209 (5)
N20.82785 (7)−0.1588 (3)0.22772 (7)0.0188 (5)
N30.66231 (7)0.2686 (3)0.31878 (7)0.0199 (5)
N40.60684 (7)0.2617 (3)0.05784 (8)0.0212 (5)
C10.87218 (9)−0.0994 (4)0.51514 (9)0.0222 (6)
C20.87279 (10)−0.1523 (4)0.56782 (9)0.0237 (6)
C30.89838 (11)−0.3262 (4)0.58935 (10)0.0297 (7)
C40.94008 (10)−0.6225 (4)0.56378 (10)0.0293 (7)
C50.95624 (10)−0.7339 (4)0.52657 (10)0.0289 (7)
C60.94985 (9)−0.6756 (4)0.47227 (10)0.0256 (7)
C70.92876 (9)−0.5015 (4)0.45748 (9)0.0227 (6)
C80.91780 (10)−0.4447 (4)0.54940 (10)0.0250 (6)
C90.91301 (9)−0.3833 (4)0.49606 (10)0.0228 (6)
C100.93615 (10)−0.5370 (4)0.36561 (10)0.0284 (7)
C110.84653 (10)−0.0316 (5)0.60098 (10)0.0267 (7)
C140.87688 (9)−0.1256 (4)0.25245 (9)0.0194 (6)
C150.89141 (9)−0.0763 (4)0.30612 (9)0.0185 (6)
C160.85213 (9)−0.0599 (4)0.33851 (9)0.0186 (6)
C170.75829 (10)−0.1170 (4)0.33859 (10)0.0221 (6)
C180.70937 (10)−0.1697 (4)0.31279 (10)0.0252 (7)
C190.69827 (10)−0.2100 (4)0.25725 (10)0.0228 (6)
C200.73699 (9)−0.2008 (4)0.22867 (9)0.0211 (6)
C210.79901 (9)−0.1100 (4)0.31026 (9)0.0193 (6)
C220.78789 (9)−0.1553 (4)0.25547 (9)0.0187 (6)
C230.68089 (10)−0.2780 (5)0.14411 (10)0.0292 (7)
C240.94706 (9)−0.0435 (4)0.32993 (9)0.0199 (6)
C251.03194 (9)−0.0446 (5)0.30958 (10)0.0284 (7)
C261.05949 (10)−0.1754 (5)0.27812 (11)0.0424 (9)
C270.61936 (9)0.2219 (4)0.28373 (9)0.0194 (6)
C280.61673 (9)0.1997 (4)0.22912 (9)0.0191 (6)
C290.66297 (10)0.2287 (4)0.20787 (9)0.0209 (6)
C300.75633 (10)0.3259 (4)0.23116 (10)0.0255 (7)
C310.79947 (10)0.3795 (4)0.26847 (11)0.0283 (7)
C320.79854 (10)0.3938 (4)0.32319 (10)0.0244 (6)
C330.75342 (10)0.3531 (4)0.34052 (10)0.0220 (6)
C340.70964 (9)0.2869 (4)0.24745 (9)0.0201 (6)
C350.70828 (9)0.3033 (4)0.30219 (9)0.0186 (6)
C360.79478 (10)0.3907 (5)0.43267 (10)0.0391 (8)
C370.56764 (10)0.1390 (4)0.19392 (9)0.0216 (6)
C380.47610 (9)0.1025 (4)0.18866 (11)0.0307 (7)
C390.43571 (10)0.2332 (5)0.20133 (10)0.0315 (7)
C400.62723 (9)0.1348 (4)0.03059 (9)0.0217 (6)
C410.62767 (9)0.1521 (4)−0.02366 (9)0.0193 (6)
C420.60759 (9)0.3223 (4)−0.05229 (9)0.0202 (6)
C430.56329 (9)0.6329 (4)−0.04349 (10)0.0225 (6)
C440.54174 (9)0.7582 (4)−0.01378 (10)0.0246 (6)
C450.54136 (9)0.7219 (4)0.04069 (10)0.0232 (6)
C460.56207 (9)0.5571 (4)0.06416 (9)0.0198 (6)
C470.58544 (9)0.4628 (4)−0.02048 (9)0.0190 (6)
C480.58500 (9)0.4274 (4)0.03387 (9)0.0186 (6)
C490.53443 (11)0.6118 (4)0.14692 (10)0.0306 (7)
C500.64771 (9)−0.0045 (4)−0.05171 (9)0.0207 (6)
C510.69833 (10)−0.2836 (4)−0.04280 (10)0.0278 (7)
C520.72593 (11)−0.4115 (5)0.00148 (12)0.0383 (8)
H1A0.8906−0.16600.44780.0251*
H10.85730.01930.50280.0266*
H20.8207−0.18360.19280.0225*
H30.66170.27780.35330.0238*
H4A0.60700.24110.09220.0254*
H40.9440−0.66600.59990.0351*
H50.9720−0.85260.53740.0347*
H60.9601−0.75610.44630.0307*
H10A0.9183−0.65960.36210.0340*
H10B0.9738−0.55710.37590.0340*
H10C0.9277−0.46970.33100.0340*
H140.9032−0.13640.23200.0233*
H170.7649−0.08480.37590.0265*
H180.6826−0.17900.33260.0303*
H190.6640−0.24370.23950.0274*
H23A0.6819−0.29300.10590.0351*
H23B0.6570−0.17500.14800.0351*
H23C0.6688−0.39600.15770.0351*
H25A1.0452−0.06200.34890.0341*
H25B1.03740.08900.30030.0341*
H26A1.0441−0.16370.23950.0508*
H26B1.0559−0.30620.28970.0508*
H26C1.0964−0.14160.28470.0508*
H270.58860.20250.29690.0233*
H300.75800.31510.19410.0306*
H310.83070.40740.25690.0339*
H320.82890.43150.34850.0292*
H36A0.80690.51980.42830.0469*
H36B0.82160.30000.42790.0469*
H36C0.78770.37640.46890.0469*
H38A0.4701−0.02770.20050.0369*
H38B0.47440.10040.14920.0369*
H39A0.44060.24680.24060.0378*
H39B0.40110.18110.18660.0378*
H39C0.43900.35730.18510.0378*
H400.64250.02520.04920.0260*
H430.56340.6607−0.08020.0270*
H440.52670.8719−0.03010.0296*
H450.52680.81170.06120.0278*
H49A0.49770.61490.12870.0368*
H49B0.54830.74100.15020.0368*
H49C0.53780.55660.18300.0368*
H51A0.7229−0.2367−0.06450.0334*
H51B0.6700−0.3530−0.06700.0334*
H52A0.7009−0.46130.02170.0459*
H52B0.7530−0.33980.02600.0459*
H52C0.7419−0.5168−0.01430.0459*
C12A0.8186 (9)0.296 (4)0.6135 (10)0.044 (6)0.295 (16)
C12B0.8007 (4)0.2488 (15)0.6076 (4)0.0358 (19)0.705 (16)
C13B0.7774 (3)0.4098 (10)0.5748 (3)0.0350 (18)0.705 (16)
C13A0.7592 (9)0.319 (4)0.5888 (5)0.059 (7)0.295 (16)
H12A0.83810.41330.61010.0524*0.295 (16)
H12B0.82490.25750.65200.0524*0.295 (16)
H13A0.75430.35750.55080.0705*0.295 (16)
H13B0.74470.41680.60900.0705*0.295 (16)
H13C0.74130.19890.59120.0705*0.295 (16)
H12C0.77290.16750.61630.0429*0.705 (16)
H12D0.82240.29510.64200.0429*0.705 (16)
H13D0.80420.47490.55990.0420*0.705 (16)
H13E0.76250.49800.59730.0420*0.705 (16)
H13F0.74990.36450.54510.0420*0.705 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0862 (17)0.0341 (13)0.0158 (10)0.0014 (12)0.0051 (10)0.0065 (10)
O20.0305 (10)0.0246 (11)0.0182 (9)0.0022 (9)0.0032 (8)−0.0007 (9)
O30.0503 (13)0.0461 (14)0.0220 (10)−0.0103 (11)0.0154 (9)0.0016 (10)
O40.0539 (13)0.0372 (14)0.0270 (11)0.0070 (11)0.0209 (10)0.0015 (10)
O50.0334 (11)0.0273 (12)0.0147 (9)0.0058 (9)0.0045 (8)−0.0009 (8)
O60.0216 (10)0.0339 (12)0.0203 (9)−0.0003 (9)0.0012 (8)−0.0023 (9)
O70.0293 (11)0.0387 (13)0.0221 (10)0.0039 (10)−0.0005 (8)−0.0099 (10)
O80.0202 (9)0.0379 (13)0.0229 (9)−0.0034 (9)0.0042 (8)−0.0059 (9)
O90.0347 (11)0.0388 (13)0.0149 (9)0.0070 (10)0.0085 (8)0.0024 (9)
O100.0232 (10)0.0390 (12)0.0193 (9)−0.0031 (9)0.0011 (8)−0.0078 (9)
O110.0412 (12)0.0305 (12)0.0200 (10)−0.0064 (10)0.0053 (9)−0.0053 (9)
O120.0214 (10)0.0321 (12)0.0227 (9)−0.0006 (9)0.0007 (8)−0.0057 (9)
O130.0392 (11)0.0301 (12)0.0187 (10)0.0061 (10)0.0107 (8)0.0021 (9)
O140.0340 (11)0.0280 (11)0.0174 (9)0.0039 (9)0.0114 (8)−0.0004 (9)
O150.0417 (12)0.0252 (11)0.0183 (10)−0.0016 (9)0.0100 (9)−0.0022 (9)
O160.0284 (10)0.0247 (11)0.0224 (9)0.0050 (9)0.0043 (8)−0.0034 (9)
N10.0279 (12)0.0220 (13)0.0128 (10)−0.0008 (11)0.0041 (9)0.0032 (10)
N20.0219 (11)0.0211 (13)0.0124 (10)−0.0002 (10)0.0016 (9)0.0001 (9)
N30.0202 (11)0.0273 (13)0.0129 (10)0.0012 (10)0.0053 (9)−0.0022 (10)
N40.0274 (12)0.0242 (13)0.0124 (10)0.0033 (11)0.0056 (9)0.0011 (10)
C10.0211 (13)0.0244 (16)0.0201 (13)−0.0031 (12)0.0023 (11)−0.0013 (12)
C20.0275 (14)0.0249 (16)0.0170 (13)−0.0089 (13)0.0013 (11)−0.0014 (12)
C30.0430 (17)0.0273 (17)0.0155 (13)−0.0111 (14)−0.0012 (12)0.0001 (12)
C40.0364 (16)0.0269 (17)0.0207 (13)−0.0094 (14)−0.0024 (12)0.0055 (13)
C50.0282 (15)0.0204 (16)0.0329 (15)−0.0022 (13)−0.0053 (12)0.0077 (14)
C60.0230 (14)0.0235 (16)0.0283 (15)−0.0025 (13)0.0011 (12)0.0002 (13)
C70.0204 (14)0.0270 (16)0.0175 (13)−0.0063 (13)−0.0029 (11)−0.0005 (12)
C80.0300 (15)0.0215 (16)0.0210 (14)−0.0070 (13)−0.0004 (12)0.0009 (12)
C90.0207 (13)0.0218 (16)0.0231 (14)−0.0048 (12)−0.0014 (11)0.0042 (12)
C100.0296 (15)0.0303 (18)0.0243 (14)0.0047 (14)0.0034 (12)−0.0012 (13)
C110.0288 (15)0.0321 (18)0.0190 (14)−0.0094 (14)0.0048 (12)0.0005 (13)
C140.0210 (13)0.0192 (15)0.0188 (13)0.0006 (12)0.0059 (11)0.0020 (12)
C150.0232 (14)0.0164 (14)0.0156 (12)0.0027 (12)0.0031 (10)0.0014 (11)
C160.0243 (14)0.0139 (14)0.0173 (13)0.0047 (12)0.0039 (11)0.0031 (11)
C170.0303 (15)0.0171 (15)0.0216 (13)0.0011 (12)0.0117 (12)−0.0001 (12)
C180.0288 (15)0.0217 (16)0.0290 (15)−0.0005 (13)0.0147 (12)0.0042 (13)
C190.0208 (14)0.0169 (15)0.0315 (15)−0.0006 (12)0.0073 (12)0.0015 (12)
C200.0240 (14)0.0170 (15)0.0214 (14)−0.0001 (12)0.0024 (11)−0.0006 (12)
C210.0259 (14)0.0130 (14)0.0196 (13)0.0029 (12)0.0060 (11)0.0040 (11)
C220.0228 (14)0.0158 (14)0.0182 (13)0.0010 (11)0.0057 (11)0.0020 (11)
C230.0236 (14)0.0335 (18)0.0267 (15)−0.0030 (14)−0.0034 (12)−0.0003 (14)
C240.0264 (14)0.0150 (14)0.0177 (13)0.0022 (12)0.0036 (11)0.0015 (12)
C250.0202 (14)0.0297 (17)0.0324 (15)−0.0038 (13)−0.0011 (12)0.0007 (14)
C260.0252 (16)0.067 (3)0.0371 (17)−0.0069 (16)0.0110 (13)−0.0095 (17)
C270.0209 (13)0.0192 (15)0.0179 (12)0.0023 (12)0.0038 (11)−0.0009 (12)
C280.0254 (14)0.0167 (14)0.0153 (12)0.0015 (12)0.0043 (11)0.0015 (11)
C290.0305 (15)0.0189 (15)0.0144 (13)0.0053 (12)0.0068 (11)0.0035 (12)
C300.0302 (15)0.0247 (16)0.0249 (14)0.0050 (13)0.0132 (12)0.0052 (13)
C310.0237 (14)0.0267 (17)0.0386 (16)0.0020 (13)0.0161 (13)0.0072 (14)
C320.0210 (14)0.0168 (15)0.0341 (15)0.0027 (12)0.0033 (12)0.0035 (13)
C330.0257 (14)0.0185 (15)0.0225 (13)0.0025 (12)0.0068 (11)−0.0014 (12)
C340.0256 (14)0.0165 (14)0.0199 (13)0.0042 (12)0.0085 (11)0.0028 (11)
C350.0202 (13)0.0147 (14)0.0220 (13)0.0015 (11)0.0072 (11)0.0006 (11)
C360.0236 (15)0.061 (3)0.0285 (15)−0.0040 (16)−0.0045 (12)−0.0112 (16)
C370.0314 (15)0.0163 (15)0.0159 (13)0.0025 (12)0.0020 (11)0.0025 (12)
C380.0236 (14)0.0288 (18)0.0349 (16)−0.0007 (13)−0.0048 (12)−0.0047 (14)
C390.0274 (15)0.044 (2)0.0213 (14)−0.0011 (15)0.0005 (12)−0.0048 (14)
C400.0227 (14)0.0237 (16)0.0187 (13)−0.0002 (12)0.0045 (11)0.0009 (12)
C410.0182 (13)0.0220 (15)0.0178 (13)−0.0003 (12)0.0038 (10)0.0017 (12)
C420.0212 (13)0.0261 (16)0.0145 (13)−0.0054 (12)0.0064 (10)−0.0013 (12)
C430.0236 (14)0.0253 (16)0.0186 (13)−0.0015 (13)0.0045 (11)0.0042 (12)
C440.0236 (14)0.0205 (16)0.0300 (15)0.0007 (12)0.0061 (12)0.0040 (13)
C450.0244 (14)0.0201 (16)0.0265 (14)0.0001 (13)0.0086 (12)−0.0009 (12)
C460.0199 (13)0.0237 (15)0.0163 (12)−0.0032 (12)0.0049 (11)−0.0010 (12)
C470.0180 (13)0.0206 (15)0.0190 (13)−0.0043 (12)0.0053 (10)0.0012 (12)
C480.0143 (12)0.0216 (15)0.0192 (13)−0.0018 (12)0.0020 (10)0.0001 (12)
C490.0414 (17)0.0308 (18)0.0238 (14)0.0018 (14)0.0163 (13)−0.0062 (13)
C500.0197 (13)0.0242 (16)0.0185 (13)−0.0029 (12)0.0045 (11)0.0022 (12)
C510.0313 (15)0.0229 (16)0.0319 (15)0.0039 (13)0.0129 (13)−0.0068 (13)
C520.0313 (16)0.0343 (19)0.0475 (18)0.0117 (15)0.0043 (14)−0.0051 (16)
C12A0.029 (11)0.054 (13)0.053 (9)−0.012 (8)0.020 (9)−0.040 (9)
C12B0.039 (5)0.046 (5)0.025 (3)0.005 (4)0.011 (4)−0.006 (4)
C13B0.035 (3)0.044 (4)0.028 (3)0.007 (3)0.012 (2)−0.008 (3)
C13A0.069 (12)0.089 (15)0.024 (7)0.041 (11)0.024 (7)0.009 (8)
Geometric parameters (Å, º) top
O1—C31.236 (4)C42—C471.473 (4)
O2—C71.373 (3)C43—C441.361 (4)
O2—C101.428 (4)C43—C471.407 (4)
O3—C111.212 (4)C44—C451.404 (4)
O4—C111.344 (4)C45—C461.367 (4)
O4—C12A1.52 (3)C46—C481.410 (4)
O4—C12B1.466 (11)C47—C481.400 (4)
O5—C161.247 (3)C51—C521.501 (4)
O6—C201.373 (3)C12A—C13A1.57 (3)
O6—C231.429 (3)C12B—C13B1.465 (12)
O7—C241.205 (3)N1—H1A0.880
O8—C241.353 (4)N2—H20.880
O8—C251.458 (3)N3—H30.880
O9—C291.249 (3)N4—H4A0.880
O10—C331.364 (4)C1—H10.950
O10—C361.434 (3)C4—H40.950
O11—C371.214 (3)C5—H50.950
O12—C371.347 (4)C6—H60.950
O12—C381.455 (3)C10—H10A0.980
O13—C421.248 (3)C10—H10B0.980
O14—C461.369 (3)C10—H10C0.980
O14—C491.435 (4)C14—H140.950
O15—C501.215 (3)C17—H170.950
O16—C501.350 (3)C18—H180.950
O16—C511.452 (4)C19—H190.950
N1—C11.335 (4)C23—H23A0.980
N1—C91.385 (4)C23—H23B0.980
N2—C141.330 (3)C23—H23C0.980
N2—C221.383 (4)C25—H25A0.990
N3—C271.322 (3)C25—H25B0.990
N3—C351.384 (4)C26—H26A0.980
N4—C401.313 (4)C26—H26B0.980
N4—C481.385 (4)C26—H26C0.980
C1—C21.381 (4)C27—H270.950
C2—C31.451 (4)C30—H300.950
C2—C111.468 (4)C31—H310.950
C3—C81.484 (4)C32—H320.950
C4—C51.362 (4)C36—H36A0.980
C4—C81.401 (4)C36—H36B0.980
C5—C61.410 (4)C36—H36C0.980
C6—C71.368 (4)C38—H38A0.990
C7—C91.412 (4)C38—H38B0.990
C8—C91.398 (4)C39—H39A0.980
C14—C151.375 (4)C39—H39B0.980
C15—C161.454 (4)C39—H39C0.980
C15—C241.479 (4)C40—H400.950
C16—C211.472 (4)C43—H430.950
C17—C181.366 (4)C44—H440.950
C17—C211.411 (4)C45—H450.950
C18—C191.403 (4)C49—H49A0.980
C19—C201.371 (4)C49—H49B0.980
C20—C221.405 (4)C49—H49C0.980
C21—C221.392 (4)C51—H51A0.990
C25—C261.503 (5)C51—H51B0.990
C27—C281.378 (4)C52—H52A0.980
C28—C291.446 (4)C52—H52B0.980
C28—C371.469 (4)C52—H52C0.980
C29—C341.470 (4)C12A—H12A0.990
C30—C311.367 (4)C12A—H12B0.990
C30—C341.404 (4)C12B—H12C0.990
C31—C321.394 (4)C12B—H12D0.990
C32—C331.381 (4)C13B—H13D0.980
C33—C351.410 (4)C13B—H13E0.980
C34—C351.398 (4)C13B—H13F0.980
C38—C391.493 (4)C13A—H13A0.980
C40—C411.381 (4)C13A—H13B0.980
C41—C421.445 (4)C13A—H13C0.980
C41—C501.471 (4)
C7—O2—C10116.8 (2)C48—N4—H4A119.180
C11—O4—C12A118.5 (10)N1—C1—H1118.465
C11—O4—C12B112.9 (5)C2—C1—H1118.468
C20—O6—C23117.1 (2)C5—C4—H4119.570
C24—O8—C25116.95 (19)C8—C4—H4119.579
C33—O10—C36115.8 (2)C4—C5—H5119.522
C37—O12—C38117.7 (2)C6—C5—H5119.501
C46—O14—C49116.9 (2)C5—C6—H6120.434
C50—O16—C51114.97 (18)C7—C6—H6120.439
C1—N1—C9121.4 (3)O2—C10—H10A109.449
C14—N2—C22121.6 (2)O2—C10—H10B109.463
C27—N3—C35121.3 (2)O2—C10—H10C109.472
C40—N4—C48121.6 (3)H10A—C10—H10B109.476
N1—C1—C2123.1 (3)H10A—C10—H10C109.482
C1—C2—C3120.1 (3)H10B—C10—H10C109.485
C1—C2—C11119.0 (3)N2—C14—H14118.396
C3—C2—C11121.0 (3)C15—C14—H14118.373
O1—C3—C2124.8 (3)C18—C17—H17119.749
O1—C3—C8120.3 (3)C21—C17—H17119.763
C2—C3—C8114.9 (3)C17—C18—H18119.704
C5—C4—C8120.9 (3)C19—C18—H18119.692
C4—C5—C6121.0 (3)C18—C19—H19120.039
C5—C6—C7119.1 (3)C20—C19—H19120.048
O2—C7—C6125.7 (3)O6—C23—H23A109.461
O2—C7—C9114.1 (3)O6—C23—H23B109.472
C6—C7—C9120.3 (3)O6—C23—H23C109.468
C3—C8—C4120.9 (3)H23A—C23—H23B109.467
C3—C8—C9120.6 (3)H23A—C23—H23C109.478
C4—C8—C9118.4 (3)H23B—C23—H23C109.481
N1—C9—C7120.0 (3)O8—C25—H25A110.428
N1—C9—C8119.7 (3)O8—C25—H25B110.435
C7—C9—C8120.3 (3)C26—C25—H25A110.441
O3—C11—O4121.9 (3)C26—C25—H25B110.440
O3—C11—C2125.3 (3)H25A—C25—H25B108.637
O4—C11—C2112.9 (3)C25—C26—H26A109.481
N2—C14—C15123.2 (3)C25—C26—H26B109.475
C14—C15—C16119.7 (2)C25—C26—H26C109.464
C14—C15—C24119.1 (3)H26A—C26—H26B109.474
C16—C15—C24121.3 (2)H26A—C26—H26C109.462
O5—C16—C15124.8 (3)H26B—C26—H26C109.471
O5—C16—C21120.2 (3)N3—C27—H27118.144
C15—C16—C21115.0 (2)C28—C27—H27118.141
C18—C17—C21120.5 (3)C31—C30—H30119.924
C17—C18—C19120.6 (3)C34—C30—H30119.929
C18—C19—C20119.9 (3)C30—C31—H31119.357
O6—C20—C19126.4 (2)C32—C31—H31119.367
O6—C20—C22113.9 (3)C31—C32—H32120.064
C19—C20—C22119.7 (3)C33—C32—H32120.076
C16—C21—C17120.5 (3)O10—C36—H36A109.470
C16—C21—C22121.1 (3)O10—C36—H36B109.468
C17—C21—C22118.4 (3)O10—C36—H36C109.477
N2—C22—C20120.1 (2)H36A—C36—H36B109.463
N2—C22—C21119.2 (2)H36A—C36—H36C109.482
C20—C22—C21120.7 (3)H36B—C36—H36C109.467
O7—C24—O8122.4 (3)O12—C38—H38A110.084
O7—C24—C15126.8 (3)O12—C38—H38B110.079
O8—C24—C15110.8 (2)C39—C38—H38A110.071
O8—C25—C26106.5 (2)C39—C38—H38B110.075
N3—C27—C28123.7 (3)H38A—C38—H38B108.416
C27—C28—C29119.3 (2)C38—C39—H39A109.465
C27—C28—C37119.5 (3)C38—C39—H39B109.469
C29—C28—C37121.2 (3)C38—C39—H39C109.467
O9—C29—C28124.3 (3)H39A—C39—H39B109.476
O9—C29—C34119.9 (3)H39A—C39—H39C109.467
C28—C29—C34115.7 (2)H39B—C39—H39C109.483
C31—C30—C34120.1 (3)N4—C40—H40118.233
C30—C31—C32121.3 (3)C41—C40—H40118.243
C31—C32—C33119.9 (3)C44—C43—H43119.611
O10—C33—C32125.4 (3)C47—C43—H43119.613
O10—C33—C35115.3 (3)C43—C44—H44119.518
C32—C33—C35119.3 (3)C45—C44—H44119.533
C29—C34—C30120.8 (3)C44—C45—H45120.107
C29—C34—C35120.3 (3)C46—C45—H45120.099
C30—C34—C35118.8 (2)O14—C49—H49A109.459
N3—C35—C33119.9 (3)O14—C49—H49B109.467
N3—C35—C34119.6 (2)O14—C49—H49C109.474
C33—C35—C34120.5 (3)H49A—C49—H49B109.475
O11—C37—O12122.8 (3)H49A—C49—H49C109.477
O11—C37—C28125.5 (3)H49B—C49—H49C109.475
O12—C37—C28111.7 (2)O16—C51—H51A110.256
O12—C38—C39108.1 (3)O16—C51—H51B110.268
N4—C40—C41123.5 (3)C52—C51—H51A110.255
C40—C41—C42119.5 (3)C52—C51—H51B110.268
C40—C41—C50119.5 (3)H51A—C51—H51B108.515
C42—C41—C50120.9 (2)C51—C52—H52A109.468
O13—C42—C41124.5 (3)C51—C52—H52B109.471
O13—C42—C47119.9 (3)C51—C52—H52C109.462
C41—C42—C47115.6 (2)H52A—C52—H52B109.481
C44—C43—C47120.8 (3)H52A—C52—H52C109.468
C43—C44—C45120.9 (3)H52B—C52—H52C109.478
C44—C45—C46119.8 (3)O4—C12A—H12A111.542
O14—C46—C45126.5 (3)O4—C12A—H12B111.524
O14—C46—C48113.9 (3)C13A—C12A—H12A111.524
C45—C46—C48119.6 (3)C13A—C12A—H12B111.522
C42—C47—C43121.8 (3)H12A—C12A—H12B109.344
C42—C47—C48120.2 (3)O4—C12B—H12C109.639
C43—C47—C48118.0 (3)O4—C12B—H12D109.628
N4—C48—C46119.8 (3)C13B—C12B—H12C109.631
N4—C48—C47119.4 (3)C13B—C12B—H12D109.629
C46—C48—C47120.8 (3)H12C—C12B—H12D108.141
O15—C50—O16122.1 (3)C12B—C13B—H13D109.464
O15—C50—C41125.2 (3)C12B—C13B—H13E109.486
O16—C50—C41112.6 (2)C12B—C13B—H13F109.469
O16—C51—C52107.3 (3)H13D—C13B—H13E109.471
O4—C12A—C13A101.2 (15)H13D—C13B—H13F109.469
O4—C12B—C13B110.1 (7)H13E—C13B—H13F109.469
C1—N1—H1A119.319C12A—C13A—H13A109.463
C9—N1—H1A119.326C12A—C13A—H13B109.488
C14—N2—H2119.188C12A—C13A—H13C109.480
C22—N2—H2119.186H13A—C13A—H13B109.471
C27—N3—H3119.376H13A—C13A—H13C109.455
C35—N3—H3119.367H13B—C13A—H13C109.470
C40—N4—H4A119.184
C7—O2—C10—H10A60.2H17—C17—C18—H18−2.7
C7—O2—C10—H10B−59.8H17—C17—C21—C162.2
C7—O2—C10—H10C−179.8H17—C17—C21—C22−179.1
C10—O2—C7—C6−3.6 (4)C17—C18—C19—C201.4 (4)
C10—O2—C7—C9178.04 (18)C17—C18—C19—H19−178.6
C11—O4—C12A—C13A−112.4 (11)H18—C18—C19—C20−178.6
C11—O4—C12A—H12A128.9H18—C18—C19—H191.4
C11—O4—C12A—H12B6.3C18—C19—C20—O6−179.2 (3)
C12A—O4—C11—O317.5 (10)C18—C19—C20—C221.5 (4)
C12A—O4—C11—C2−164.0 (10)H19—C19—C20—O60.8
C11—O4—C12B—C13B−167.1 (4)H19—C19—C20—C22−178.5
C11—O4—C12B—H12C−46.4O6—C20—C22—N2−3.9 (4)
C11—O4—C12B—H12D72.2O6—C20—C22—C21177.35 (19)
C12B—O4—C11—O3−6.0 (5)C19—C20—C22—N2175.4 (3)
C12B—O4—C11—C2172.4 (4)C19—C20—C22—C21−3.3 (4)
C12A—O4—C12B—C13B83 (3)C16—C21—C22—N22.0 (4)
C12A—O4—C12B—H12C−156.1C16—C21—C22—C20−179.2 (2)
C12A—O4—C12B—H12D−37.5C17—C21—C22—N2−176.7 (2)
C12B—O4—C12A—C13A−31.8 (16)C17—C21—C22—C202.1 (4)
C12B—O4—C12A—H12A−150.5O8—C25—C26—H26A55.7
C12B—O4—C12A—H12B86.9O8—C25—C26—H26B−64.3
C20—O6—C23—H23A177.4O8—C25—C26—H26C175.7
C20—O6—C23—H23B57.4H25A—C25—C26—H26A175.6
C20—O6—C23—H23C−62.6H25A—C25—C26—H26B55.6
C23—O6—C20—C191.8 (4)H25A—C25—C26—H26C−64.4
C23—O6—C20—C22−178.91 (19)H25B—C25—C26—H26A−64.2
C24—O8—C25—C26157.98 (18)H25B—C25—C26—H26B175.8
C24—O8—C25—H25A38.1H25B—C25—C26—H26C55.8
C24—O8—C25—H25B−82.1N3—C27—C28—C29−0.1 (4)
C25—O8—C24—O7−8.2 (4)N3—C27—C28—C37177.2 (2)
C25—O8—C24—C15171.78 (18)H27—C27—C28—C29179.9
C33—O10—C36—H36A65.9H27—C27—C28—C37−2.8
C33—O10—C36—H36B−54.1C27—C28—C29—O9179.5 (3)
C33—O10—C36—H36C−174.1C27—C28—C29—C34−1.9 (4)
C36—O10—C33—C32−4.6 (4)C27—C28—C37—O11−158.9 (3)
C36—O10—C33—C35175.1 (2)C27—C28—C37—O1219.8 (4)
C37—O12—C38—C39−148.8 (2)C29—C28—C37—O1118.4 (4)
C37—O12—C38—H38A90.9C29—C28—C37—O12−162.9 (2)
C37—O12—C38—H38B−28.6C37—C28—C29—O92.2 (4)
C38—O12—C37—O113.7 (4)C37—C28—C29—C34−179.2 (2)
C38—O12—C37—C28−175.01 (19)O9—C29—C34—C301.0 (4)
C46—O14—C49—H49A59.8O9—C29—C34—C35−178.7 (2)
C46—O14—C49—H49B−60.2C28—C29—C34—C30−177.6 (2)
C46—O14—C49—H49C179.8C28—C29—C34—C352.7 (4)
C49—O14—C46—C457.3 (4)C31—C30—C34—C29−179.8 (3)
C49—O14—C46—C48−172.14 (18)C31—C30—C34—C35−0.2 (4)
C50—O16—C51—C52−175.17 (18)C34—C30—C31—C321.0 (4)
C50—O16—C51—H51A64.7C34—C30—C31—H31−179.0
C50—O16—C51—H51B−55.1H30—C30—C31—C32−179.0
C51—O16—C50—O150.5 (4)H30—C30—C31—H311.0
C51—O16—C50—C41−179.79 (18)H30—C30—C34—C290.2
C1—N1—C9—C7174.2 (2)H30—C30—C34—C35179.8
C1—N1—C9—C8−4.3 (4)C30—C31—C32—C330.1 (4)
C9—N1—C1—C21.0 (4)C30—C31—C32—H32−179.9
C9—N1—C1—H1−179.0H31—C31—C32—C33−179.9
H1A—N1—C1—C2−179.0H31—C31—C32—H320.1
H1A—N1—C1—H11.0C31—C32—C33—O10177.6 (3)
H1A—N1—C9—C7−5.8C31—C32—C33—C35−2.0 (4)
H1A—N1—C9—C8175.8H32—C32—C33—O10−2.4
C14—N2—C22—C20−176.7 (2)H32—C32—C33—C35178.0
C14—N2—C22—C212.1 (4)O10—C33—C35—N32.6 (4)
C22—N2—C14—C15−3.4 (4)O10—C33—C35—C34−176.83 (19)
C22—N2—C14—H14176.6C32—C33—C35—N3−177.7 (2)
H2—N2—C14—C15176.6C32—C33—C35—C342.8 (4)
H2—N2—C14—H14−3.4C29—C34—C35—N3−1.5 (4)
H2—N2—C22—C203.3C29—C34—C35—C33177.9 (2)
H2—N2—C22—C21−177.9C30—C34—C35—N3178.8 (2)
C27—N3—C35—C33179.9 (2)C30—C34—C35—C33−1.7 (4)
C27—N3—C35—C34−0.7 (4)O12—C38—C39—H39A−52.5
C35—N3—C27—C281.5 (4)O12—C38—C39—H39B−172.5
C35—N3—C27—H27−178.5O12—C38—C39—H39C67.4
H3—N3—C27—C28−178.5H38A—C38—C39—H39A67.7
H3—N3—C27—H271.5H38A—C38—C39—H39B−52.3
H3—N3—C35—C33−0.1H38A—C38—C39—H39C−172.3
H3—N3—C35—C34179.3H38B—C38—C39—H39A−172.8
C40—N4—C48—C46178.00 (19)H38B—C38—C39—H39B67.2
C40—N4—C48—C47−1.2 (4)H38B—C38—C39—H39C−52.8
C48—N4—C40—C41−1.6 (4)N4—C40—C41—C423.7 (4)
C48—N4—C40—H40178.4N4—C40—C41—C50−175.2 (2)
H4A—N4—C40—C41178.4H40—C40—C41—C42−176.3
H4A—N4—C40—H40−1.6H40—C40—C41—C504.8
H4A—N4—C48—C46−2.0C40—C41—C42—O13175.7 (2)
H4A—N4—C48—C47178.8C40—C41—C42—C47−2.9 (3)
N1—C1—C2—C34.3 (4)C40—C41—C50—O15161.5 (3)
N1—C1—C2—C11−174.7 (2)C40—C41—C50—O16−18.2 (3)
H1—C1—C2—C3−175.7C42—C41—C50—O15−17.4 (4)
H1—C1—C2—C115.3C42—C41—C50—O16163.0 (2)
C1—C2—C3—O1174.9 (3)C50—C41—C42—O13−5.4 (4)
C1—C2—C3—C8−5.9 (4)C50—C41—C42—C47175.99 (19)
C1—C2—C11—O3166.6 (3)O13—C42—C47—C433.0 (4)
C1—C2—C11—O4−11.7 (4)O13—C42—C47—C48−178.39 (19)
C3—C2—C11—O3−12.4 (4)C41—C42—C47—C43−178.36 (19)
C3—C2—C11—O4169.3 (3)C41—C42—C47—C480.3 (3)
C11—C2—C3—O1−6.1 (4)C44—C43—C47—C42178.1 (2)
C11—C2—C3—C8173.1 (2)C44—C43—C47—C48−0.5 (4)
O1—C3—C8—C43.7 (4)C47—C43—C44—C450.5 (4)
O1—C3—C8—C9−178.0 (3)C47—C43—C44—H44−179.5
C2—C3—C8—C4−175.6 (2)H43—C43—C44—C45−179.5
C2—C3—C8—C92.8 (4)H43—C43—C44—H440.5
C5—C4—C8—C3177.7 (3)H43—C43—C47—C42−1.9
C5—C4—C8—C9−0.6 (4)H43—C43—C47—C48179.5
C8—C4—C5—C6−1.6 (4)C43—C44—C45—C46−1.1 (4)
C8—C4—C5—H5178.4C43—C44—C45—H45178.8
H4—C4—C5—C6178.4H44—C44—C45—C46178.8
H4—C4—C5—H5−1.5H44—C44—C45—H45−1.2
H4—C4—C8—C3−2.3C44—C45—C46—O14−177.6 (2)
H4—C4—C8—C9179.3C44—C45—C46—C481.8 (4)
C4—C5—C6—C72.3 (4)H45—C45—C46—O142.4
C4—C5—C6—H6−177.7H45—C45—C46—C48−178.2
H5—C5—C6—C7−177.7O14—C46—C48—N4−1.6 (3)
H5—C5—C6—H62.3O14—C46—C48—C47177.60 (18)
C5—C6—C7—O2−179.1 (2)C45—C46—C48—N4178.9 (2)
C5—C6—C7—C9−0.8 (4)C45—C46—C48—C47−1.9 (4)
H6—C6—C7—O20.9C42—C47—C48—N41.8 (4)
H6—C6—C7—C9179.2C42—C47—C48—C46−177.45 (19)
O2—C7—C9—N1−1.4 (3)C43—C47—C48—N4−179.54 (19)
O2—C7—C9—C8177.04 (18)C43—C47—C48—C461.2 (4)
C6—C7—C9—N1−179.8 (2)O16—C51—C52—H52A62.3
C6—C7—C9—C8−1.4 (4)O16—C51—C52—H52B−57.7
C3—C8—C9—N12.2 (4)O16—C51—C52—H52C−177.7
C3—C8—C9—C7−176.2 (2)H51A—C51—C52—H52A−177.6
C4—C8—C9—N1−179.5 (2)H51A—C51—C52—H52B62.4
C4—C8—C9—C72.1 (4)H51A—C51—C52—H52C−57.6
N2—C14—C15—C160.4 (4)H51B—C51—C52—H52A−57.8
N2—C14—C15—C24179.6 (2)H51B—C51—C52—H52B−177.8
H14—C14—C15—C16−179.6H51B—C51—C52—H52C62.2
H14—C14—C15—C24−0.4O4—C12A—C13A—H13A−61.5
C14—C15—C16—O5−177.2 (3)O4—C12A—C13A—H13B178.5
C14—C15—C16—C213.4 (4)O4—C12A—C13A—H13C58.5
C14—C15—C24—O7171.8 (3)H12A—C12A—C13A—H13A57.3
C14—C15—C24—O8−8.1 (4)H12A—C12A—C13A—H13B−62.8
C16—C15—C24—O7−9.0 (4)H12A—C12A—C13A—H13C177.2
C16—C15—C24—O8171.1 (2)H12B—C12A—C13A—H13A179.8
C24—C15—C16—O53.6 (4)H12B—C12A—C13A—H13B59.8
C24—C15—C16—C21−175.8 (2)H12B—C12A—C13A—H13C−60.2
O5—C16—C21—C17−5.3 (4)O4—C12B—C13B—H13D−47.5
O5—C16—C21—C22176.0 (2)O4—C12B—C13B—H13E−167.5
C15—C16—C21—C17174.1 (2)O4—C12B—C13B—H13F72.5
C15—C16—C21—C22−4.6 (4)H12C—C12B—C13B—H13D−168.2
C18—C17—C21—C16−177.8 (2)H12C—C12B—C13B—H13E71.8
C18—C17—C21—C220.9 (4)H12C—C12B—C13B—H13F−48.2
C21—C17—C18—C19−2.7 (4)H12D—C12B—C13B—H13D73.2
C21—C17—C18—H18177.3H12D—C12B—C13B—H13E−46.8
H17—C17—C18—C19177.3H12D—C12B—C13B—H13F−166.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O20.882.332.665 (3)103
N1—H1A···O50.881.932.729 (3)151
N2—H2···O3i0.882.192.873 (3)134
N2—H2···O60.882.312.656 (4)103
N3—H3···O100.882.352.685 (3)103
N3—H3···O13ii0.882.212.857 (4)130
N3—H3···O15ii0.882.262.898 (3)129
N4—H4A···O90.882.032.716 (3)134
N4—H4A···O140.882.312.652 (3)103
Symmetry codes: (i) x, −y−1/2, z−1/2; (ii) x, −y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O20.8802.3302.665 (3)102.7
N1—H1A···O50.8801.9252.729 (3)151.2
N2—H2···O3i0.8802.1902.873 (3)134.1
N2—H2···O60.8802.3142.656 (4)103.1
N3—H3···O100.8802.3502.685 (3)102.7
N3—H3···O13ii0.8802.2112.857 (4)129.9
N3—H3···O15ii0.8802.2592.898 (3)129.4
N4—H4A···O90.8802.0342.716 (3)133.5
N4—H4A···O140.8802.3092.652 (3)103.2
Symmetry codes: (i) x, −y−1/2, z−1/2; (ii) x, −y+1/2, z+1/2.
 

Acknowledgements

This work was supported in partby JSPS KAKENHI Grant No. 24590141. We acknowledge the University of Shizuoka for instrumental support.

References

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ISSN: 2056-9890
Volume 70| Part 6| June 2014| Page o719
doi:10.1107/S1600536814011854
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