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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1579–o1580.
Published online 2010 June 5. doi:  10.1107/S1600536810018970
PMCID: PMC3006763

2,2-Bis(hy­droxy­meth­yl)-2,3-dihydro-1H-pyrrolizin-1-one

Abstract

The title compound, C9H11NO3, was prepared by an Aldol reaction of 2,3-dihydro-1H-pyrrolizin-1-one with formaldehyde. The asymmetric unit contains six mol­ecules. The pyrrolizine ring system in each mol­ecule is planar, the maximum atomic deviation being 0.066 (2) Å. In the crystal structure, mol­ecules are liked together by an extensive O—H(...)O hydrogen-bonding network.

Related literature

For general background to 2,3-dihydro­pyrrolizine derivatives and for the biological activity of related compounds, see: Meinwald & Meinwald (1965 [triangle]); Skvortsov & Astakhova (1992 [triangle]); Albrecht et al. (2008 [triangle]); Mishra et al. (2008 [triangle]); Morúaa et al. (2009 [triangle]). For the preparation of the starting material, see: Clemo & Ramage (1931 [triangle]); Braunholtz et al. (1962 [triangle]). For a related structure, see: Ali et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1579-scheme1.jpg

Experimental

Crystal data

  • C9H11NO3
  • M r = 181.19
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1579-efi1.jpg
  • a = 10.2601 (8) Å
  • b = 39.863 (3) Å
  • c = 12.412 (1) Å
  • β = 90.273 (6)°
  • V = 5076.4 (7) Å3
  • Z = 24
  • Cu Kα radiation
  • μ = 0.90 mm−1
  • T = 113 K
  • 0.22 × 0.18 × 0.16 mm

Data collection

  • Rigaku Saturn70 CCD diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2009 [triangle]) T min = 0.827, T max = 0.870
  • 51559 measured reflections
  • 9889 independent reflections
  • 8550 reflections with I > 2σ(I)
  • R int = 0.059

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.122
  • S = 1.09
  • 9889 reflections
  • 751 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: CrystalClear (Rigaku, 2009 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810018970/xu2763sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018970/xu2763Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

YA is grateful to the Pakistan Council of Scientific & Industrial Research, Ministry of Science & Technology, Government of Pakistan, for financial support. PY is grateful to Tianjin University of Science & Technology for research funding (research grant No. 2009 0431). The authors are grateful to Dr Song Haibin (Nankai University) for the data collection.

supplementary crystallographic information

Comment

Title compound was prepared in order to synthesize new derivatives of this series. Derivatives of 2,3-dihydropyrrolizine became known through studies of their synthesis (Clemo & Ramage, 1931; Braunholtz et al., 1962), and isolation from natural source (Meinwald & Meinwald, 1965). Depending on their structure derivatives of 2,3-dihydropyrrolizine have shown merit as analgesics, anti-inflammatory agents, myorelaxants, inhibitors of thrombocyte aggregation, fibrinolytics, temperature-lowering substances and drugs for the treatment of glaucoma and conjunctivitis (Skvortsov et al., 1992). The most important of these, Ketorolac, is reported in literature as one of the most effective nonsteroidal anti-inflammatory drugs to alleviate renoureteral colic (Morúaa et al., 2009). But it suffers from the general side effects of NSAIDs, owing to presence of free carboxylic acid group (Mishra et al., 2008). Licofelone(2-[6-(4-Chlorophenyl)-2,2- dimethyl-7-phenyl-2,3-dihydro-1Hpyrrolizin-5-yl] acetic acid) is a dual inhibitor of both cyclooxygenase isoforms and 5-lipoxygenase (Albrecht et al., 2008). Crystal structures of related molecules are reported (Ali et al., 2010).

Numbering scheme for the title compound is shown in an ORTEP (Farrugia, 1997) plot of the molecule at 70% ellipsoid probability limit (Fig. 1). In the crystal structure of the title compound, molecules are connected via intermolecular O—H···O hydrogen bonds (Table 1) to form discrete zigzag chains (Fig. 3). Assymetric unit contains, nearly identical, six molecules. The pyrrolizin ring system is almost planner [maximum deviation = 0.066 (2) Å] with two methylene groups, bearing hydroxyl groups, above and below the plane of the ring. Thus forming a flying bird like shape (Fig. 2).

Experimental

A 100 ml round bottom one neck flask, equipped with a magnetic stirrer, is charged with 20 ml of Ethanol 95%, 4.03 g (33.3 mmol) of 2,3-dihydro-1H-pyrrolizin-1-one and 8 ml formalin (formaldehyde 37% aquous). The reaction vessel is immersed in a bath of cold water and l.6 ml of 5% sodium hydroxide aqueous solution is added slowly (during about 10 minutes) from a dropping funnel. The rate of addition was adjusted so that the temperature remains between 293 and 298 K. The mixture was stirred overnight at room temperature. Dilute hydrochloric acid was added to render the mixture just acidic to litmus paper (pH = 5 to 6). Solvents were removed under diminished pressure. The residue was subjected directly to Flash Column chromatography (Petroleum Ether : Ethyl Acetate = 1:1) to give 3.77 g (62.5%) of crystalline mass, m.p. 121-122 °C. Single crystals for X-Ray analysis were prepared by evaporation from a methanol solution.

Refinement

Hydroxy H atoms were located in a difference Fourier map and refined isotropically. Other H atoms were geometrically positioned and refined using a riding model with Uiso(H) = 1.2Ueq(C) and with C—H = 0.95 or 0.99 Å.

Figures

Fig. 1.
View of the single molecule showing atom numbering scheme at 70% ellipsoids probability level. Hydrogen atoms are drawn as spheres of an arbitrary radius.
Fig. 2.
View of molecule from below, showing two hydroxyl bearign methylene groups, one above and one below the ring system.
Fig. 3.
Packing diagram of cell unit showing discrete zigzag chains.
Fig. 4.
Chemical Reaction Scheme.

Crystal data

C9H11NO3F(000) = 2304
Mr = 181.19Dx = 1.422 Mg m3
Monoclinic, P21/cMelting point: 395 K
Hall symbol: -P 2ybcCu Kα radiation, λ = 1.54187 Å
a = 10.2601 (8) ÅCell parameters from 5462 reflections
b = 39.863 (3) Åθ = 27.5–72.2°
c = 12.412 (1) ŵ = 0.90 mm1
β = 90.273 (6)°T = 113 K
V = 5076.4 (7) Å3Prism, colourless
Z = 240.22 × 0.18 × 0.16 mm

Data collection

Rigaku Saturn70 CCD camera diffractometer9889 independent reflections
Radiation source: fine-focus sealed tube8550 reflections with I > 2σ(I)
multilayerRint = 0.059
ω scansθmax = 72.7°, θmin = 2.2°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2009)h = −12→12
Tmin = 0.827, Tmax = 0.870k = −48→48
51559 measured reflectionsl = −12→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 1.09w = 1/[σ2(Fo2) + (0.0583P)2 + 1.4861P] where P = (Fo2 + 2Fc2)/3
9889 reflections(Δ/σ)max < 0.001
751 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = −0.27 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.00788 (10)0.23601 (3)0.79919 (9)0.0209 (2)
O20.12194 (13)0.26396 (3)1.04690 (11)0.0315 (3)
H20.175 (2)0.2699 (6)1.102 (2)0.050 (7)*
O30.29990 (12)0.22299 (3)0.70802 (10)0.0285 (3)
H30.376 (3)0.2300 (7)0.688 (2)0.062 (8)*
O40.50703 (11)0.24375 (3)0.58345 (9)0.0224 (3)
O50.60266 (12)0.26017 (3)0.32413 (10)0.0245 (3)
H50.651 (2)0.2602 (6)0.272 (2)0.042 (7)*
O60.79773 (11)0.23639 (3)0.67012 (10)0.0240 (3)
H60.874 (3)0.2378 (6)0.706 (2)0.044 (7)*
O71.09436 (11)0.06150 (3)0.47694 (9)0.0240 (3)
O80.80230 (11)0.07468 (3)0.38956 (9)0.0230 (3)
H80.728 (2)0.0737 (6)0.354 (2)0.045 (7)*
O90.99084 (12)0.03716 (3)0.72620 (11)0.0273 (3)
H90.941 (2)0.0409 (6)0.778 (2)0.041 (7)*
O101.09012 (11)0.05039 (3)−0.03329 (10)0.0229 (3)
O110.79658 (12)0.04535 (3)−0.12018 (9)0.0248 (3)
H110.722 (2)0.0404 (6)−0.1456 (19)0.037 (6)*
O120.98992 (12)0.06862 (3)0.22557 (10)0.0250 (3)
H120.943 (2)0.0722 (6)0.279 (2)0.044 (7)*
O130.59009 (10)0.03485 (3)0.74524 (9)0.0209 (2)
O140.47801 (12)0.05834 (3)0.49770 (10)0.0278 (3)
H140.428 (2)0.0666 (6)0.447 (2)0.041 (6)*
O150.29842 (12)0.03026 (3)0.84705 (10)0.0277 (3)
H150.217 (3)0.0385 (7)0.868 (2)0.065 (8)*
O160.59239 (10)0.07059 (3)0.25528 (9)0.0220 (2)
O170.49233 (12)0.04752 (3)−0.00169 (10)0.0255 (3)
H170.438 (3)0.0448 (7)−0.056 (2)0.054 (8)*
O180.29584 (11)0.07697 (3)0.33930 (10)0.0219 (2)
H180.226 (2)0.0734 (6)0.3752 (19)0.036 (6)*
N10.21112 (13)0.30568 (3)0.82425 (11)0.0209 (3)
N20.70994 (13)0.18680 (3)0.45337 (11)0.0189 (3)
N30.88997 (12)0.11537 (3)0.61882 (11)0.0185 (3)
N40.87478 (12)0.11657 (3)0.00760 (11)0.0188 (3)
N50.38885 (13)0.10504 (3)0.72801 (11)0.0188 (3)
N60.37989 (12)0.12235 (3)0.11227 (11)0.0188 (3)
C10.21244 (17)0.33884 (4)0.80508 (15)0.0252 (4)
H10.28130.35390.82180.030*
C20.09387 (17)0.34708 (4)0.75598 (15)0.0270 (4)
H2A0.06760.36890.73390.032*
C30.02071 (16)0.31774 (4)0.74498 (14)0.0233 (3)
H3A−0.06360.31580.71360.028*
C40.09541 (15)0.29189 (4)0.78898 (13)0.0196 (3)
C50.09389 (15)0.25707 (4)0.81614 (13)0.0174 (3)
C60.22115 (15)0.24870 (4)0.87559 (13)0.0189 (3)
C70.30154 (16)0.28135 (4)0.87220 (16)0.0255 (4)
H7A0.32840.28830.94550.031*
H7B0.38020.27860.82710.031*
C80.18828 (16)0.23812 (4)0.99139 (14)0.0228 (3)
H8A0.13310.21780.98960.027*
H8B0.26980.23251.03050.027*
C90.28809 (16)0.21894 (4)0.82123 (14)0.0214 (3)
H9A0.37610.21600.85300.026*
H9B0.23760.19830.83610.026*
C100.71767 (17)0.15398 (4)0.42930 (14)0.0247 (4)
H100.78800.14310.39410.030*
C110.60312 (18)0.13877 (4)0.46555 (15)0.0281 (4)
H11A0.58120.11570.45840.034*
C120.52670 (17)0.16340 (4)0.51397 (15)0.0250 (4)
H12A0.44380.16030.54620.030*
C130.59529 (15)0.19350 (4)0.50604 (13)0.0185 (3)
C140.59120 (14)0.22819 (4)0.53385 (13)0.0176 (3)
C150.71635 (15)0.24481 (4)0.49083 (13)0.0175 (3)
C160.79390 (15)0.21608 (4)0.43832 (14)0.0200 (3)
H16A0.80860.22050.36090.024*
H16B0.87910.21290.47460.024*
C170.67828 (15)0.27266 (4)0.41111 (13)0.0199 (3)
H17A0.62800.29010.44950.024*
H17B0.75830.28320.38260.024*
C180.78953 (15)0.26041 (4)0.58545 (13)0.0202 (3)
H18A0.87810.26710.56280.024*
H18B0.74300.28070.61080.024*
C190.88204 (17)0.14731 (4)0.65250 (15)0.0250 (4)
H190.81260.15700.69220.030*
C200.99474 (18)0.16368 (4)0.61835 (16)0.0289 (4)
H201.01590.18650.63110.035*
C211.07093 (17)0.14066 (4)0.56230 (15)0.0256 (4)
H211.15280.14490.52960.031*
C221.00406 (15)0.11023 (4)0.56347 (13)0.0198 (3)
C231.00883 (15)0.07613 (4)0.52823 (12)0.0180 (3)
C240.88236 (14)0.05865 (4)0.56444 (13)0.0172 (3)
C250.80686 (15)0.08571 (4)0.62717 (13)0.0188 (3)
H25A0.72030.08980.59410.023*
H25B0.79500.07910.70330.023*
C260.80900 (16)0.04725 (4)0.46370 (14)0.0219 (3)
H26A0.85480.02810.43020.026*
H26B0.72000.03990.48310.026*
C270.91564 (16)0.02804 (4)0.63456 (14)0.0231 (3)
H27A0.83390.01720.65840.028*
H27B0.96490.01160.59110.028*
C280.85751 (17)0.14907 (4)−0.01890 (14)0.0244 (4)
H280.78560.16280.00060.029*
C290.96452 (18)0.15888 (4)−0.08015 (15)0.0290 (4)
H290.97850.1805−0.10980.035*
C301.04757 (17)0.13129 (4)−0.09025 (14)0.0254 (4)
H301.12810.1307−0.12770.031*
C310.98977 (15)0.10492 (4)−0.03510 (13)0.0193 (3)
C321.00243 (14)0.07002 (4)−0.00908 (12)0.0170 (3)
C330.88121 (14)0.05919 (4)0.05423 (13)0.0168 (3)
C340.79884 (15)0.09140 (4)0.06617 (13)0.0198 (3)
H34A0.71130.08850.03360.024*
H34B0.78910.09770.14290.024*
C350.81048 (15)0.03267 (4)−0.01264 (13)0.0195 (3)
H35A0.86120.0115−0.01310.023*
H35B0.72370.02800.01850.023*
C360.92196 (16)0.04439 (4)0.16262 (13)0.0207 (3)
H36A0.84360.03680.20200.025*
H36B0.97870.02470.15070.025*
C370.38558 (17)0.13759 (4)0.75589 (14)0.0246 (4)
H370.31690.15290.74140.030*
C380.50179 (18)0.14466 (4)0.81014 (15)0.0286 (4)
H380.52600.16580.83920.034*
C390.57621 (16)0.11548 (4)0.81455 (14)0.0236 (4)
H390.65970.11290.84700.028*
C400.50416 (15)0.09073 (4)0.76208 (13)0.0182 (3)
C410.50526 (14)0.05629 (4)0.72993 (12)0.0160 (3)
C420.37586 (14)0.04861 (4)0.67170 (13)0.0163 (3)
C430.30152 (15)0.08220 (4)0.66999 (14)0.0211 (3)
H43A0.28640.09000.59520.025*
H43B0.21660.08020.70700.025*
C440.40411 (15)0.03513 (4)0.55893 (13)0.0197 (3)
H44A0.45270.01380.56490.024*
H44B0.32080.03050.52120.024*
C450.30486 (15)0.02149 (4)0.73617 (13)0.0195 (3)
H45A0.21550.01860.70720.023*
H45B0.3513−0.00010.72840.023*
C460.36546 (17)0.15442 (4)0.08148 (14)0.0242 (4)
H460.29520.16330.04030.029*
C470.47214 (17)0.17239 (4)0.12078 (15)0.0274 (4)
H470.48740.19570.11120.033*
C480.55255 (17)0.15008 (4)0.17670 (14)0.0247 (4)
H480.63240.15530.21190.030*
C490.49328 (15)0.11869 (4)0.17092 (13)0.0187 (3)
C500.50457 (14)0.08431 (4)0.20370 (12)0.0168 (3)
C510.38331 (14)0.06528 (4)0.16315 (13)0.0168 (3)
C520.30237 (15)0.09173 (4)0.10148 (13)0.0196 (3)
H52A0.29160.08540.02480.024*
H52B0.21520.09450.13420.024*
C530.42590 (16)0.03599 (4)0.09137 (13)0.0204 (3)
H53A0.48390.02090.13300.024*
H53B0.34820.02290.06910.024*
C540.31093 (15)0.05104 (4)0.26027 (13)0.0195 (3)
H54A0.22430.04260.23750.023*
H54B0.36070.03210.29150.023*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0194 (5)0.0193 (6)0.0238 (6)−0.0030 (4)−0.0024 (4)0.0027 (5)
O20.0339 (7)0.0348 (7)0.0258 (7)0.0121 (5)−0.0037 (6)−0.0075 (6)
O30.0235 (6)0.0382 (7)0.0239 (7)0.0002 (5)0.0059 (5)0.0027 (5)
O40.0198 (6)0.0245 (6)0.0229 (6)0.0021 (4)0.0041 (4)−0.0004 (5)
O50.0213 (6)0.0331 (7)0.0190 (6)−0.0004 (5)−0.0008 (5)0.0014 (5)
O60.0203 (6)0.0326 (7)0.0191 (6)−0.0027 (5)−0.0035 (5)0.0048 (5)
O70.0178 (5)0.0327 (7)0.0215 (6)0.0020 (5)0.0037 (4)−0.0027 (5)
O80.0193 (6)0.0300 (7)0.0196 (6)0.0003 (5)−0.0043 (5)−0.0006 (5)
O90.0235 (6)0.0372 (7)0.0213 (7)0.0065 (5)0.0007 (5)0.0055 (5)
O100.0182 (5)0.0251 (6)0.0255 (6)0.0033 (4)0.0021 (5)−0.0032 (5)
O110.0203 (6)0.0371 (7)0.0170 (6)−0.0064 (5)−0.0035 (5)0.0012 (5)
O120.0237 (6)0.0328 (7)0.0183 (6)−0.0063 (5)0.0001 (5)−0.0035 (5)
O130.0174 (5)0.0212 (6)0.0240 (6)0.0016 (4)−0.0021 (4)0.0008 (5)
O140.0236 (6)0.0413 (8)0.0183 (6)−0.0071 (5)−0.0009 (5)0.0059 (5)
O150.0200 (6)0.0461 (8)0.0170 (6)0.0011 (5)0.0037 (5)0.0013 (5)
O160.0175 (5)0.0266 (6)0.0219 (6)0.0008 (4)−0.0040 (4)0.0030 (5)
O170.0254 (6)0.0335 (7)0.0175 (6)−0.0014 (5)0.0012 (5)−0.0017 (5)
O180.0210 (6)0.0247 (6)0.0201 (6)−0.0005 (5)0.0048 (5)−0.0014 (5)
N10.0216 (7)0.0167 (7)0.0242 (8)−0.0015 (5)−0.0006 (5)0.0000 (5)
N20.0202 (6)0.0175 (7)0.0190 (7)0.0008 (5)−0.0004 (5)−0.0006 (5)
N30.0198 (6)0.0175 (7)0.0182 (7)−0.0001 (5)−0.0004 (5)−0.0005 (5)
N40.0198 (6)0.0168 (7)0.0198 (7)−0.0002 (5)−0.0008 (5)0.0020 (5)
N50.0200 (6)0.0169 (7)0.0194 (7)0.0009 (5)−0.0003 (5)−0.0015 (5)
N60.0198 (6)0.0178 (7)0.0189 (7)0.0003 (5)0.0002 (5)0.0019 (5)
C10.0309 (9)0.0169 (8)0.0277 (9)−0.0044 (7)0.0059 (7)0.0007 (7)
C20.0321 (9)0.0190 (8)0.0300 (10)0.0046 (7)0.0069 (7)0.0075 (7)
C30.0232 (8)0.0228 (8)0.0239 (9)0.0036 (6)0.0016 (6)0.0039 (7)
C40.0190 (7)0.0191 (8)0.0207 (8)−0.0009 (6)0.0008 (6)0.0015 (6)
C50.0182 (7)0.0180 (8)0.0160 (8)0.0009 (6)0.0002 (6)0.0008 (6)
C60.0173 (7)0.0165 (8)0.0228 (9)0.0005 (6)−0.0021 (6)0.0008 (6)
C70.0206 (8)0.0196 (8)0.0361 (10)−0.0001 (6)−0.0063 (7)0.0015 (7)
C80.0233 (8)0.0235 (8)0.0216 (9)0.0049 (6)−0.0027 (6)−0.0008 (7)
C90.0202 (8)0.0213 (8)0.0228 (9)0.0023 (6)0.0014 (6)0.0007 (6)
C100.0304 (9)0.0191 (8)0.0245 (9)0.0040 (7)−0.0060 (7)−0.0031 (7)
C110.0358 (10)0.0173 (8)0.0311 (10)−0.0019 (7)−0.0119 (8)0.0007 (7)
C120.0248 (8)0.0226 (9)0.0275 (9)−0.0047 (6)−0.0047 (7)0.0058 (7)
C130.0192 (7)0.0178 (8)0.0185 (8)0.0010 (6)−0.0014 (6)0.0015 (6)
C140.0162 (7)0.0215 (8)0.0152 (8)0.0003 (6)−0.0027 (6)0.0015 (6)
C150.0179 (7)0.0175 (8)0.0170 (8)−0.0003 (6)0.0003 (6)0.0001 (6)
C160.0194 (7)0.0189 (8)0.0216 (9)0.0001 (6)0.0015 (6)0.0001 (6)
C170.0218 (8)0.0192 (8)0.0187 (8)0.0007 (6)0.0005 (6)0.0006 (6)
C180.0203 (8)0.0205 (8)0.0198 (8)−0.0013 (6)−0.0010 (6)−0.0002 (6)
C190.0288 (9)0.0205 (8)0.0255 (9)0.0026 (7)−0.0027 (7)−0.0013 (7)
C200.0354 (9)0.0176 (8)0.0335 (10)−0.0045 (7)−0.0085 (8)0.0026 (7)
C210.0238 (8)0.0246 (9)0.0282 (10)−0.0050 (7)−0.0038 (7)0.0062 (7)
C220.0187 (7)0.0231 (8)0.0175 (8)−0.0013 (6)−0.0006 (6)0.0019 (6)
C230.0172 (7)0.0237 (8)0.0132 (8)0.0003 (6)−0.0014 (6)0.0001 (6)
C240.0163 (7)0.0174 (8)0.0179 (8)0.0013 (6)0.0008 (6)−0.0011 (6)
C250.0183 (7)0.0179 (8)0.0204 (8)−0.0002 (6)0.0026 (6)0.0009 (6)
C260.0206 (8)0.0210 (8)0.0242 (9)−0.0007 (6)−0.0002 (6)−0.0041 (7)
C270.0246 (8)0.0215 (8)0.0232 (9)0.0040 (6)0.0030 (6)0.0012 (7)
C280.0292 (9)0.0164 (8)0.0275 (9)0.0008 (6)−0.0056 (7)0.0009 (7)
C290.0364 (10)0.0196 (8)0.0309 (10)−0.0084 (7)−0.0070 (8)0.0076 (7)
C300.0252 (8)0.0267 (9)0.0244 (9)−0.0062 (7)0.0007 (7)0.0048 (7)
C310.0180 (7)0.0217 (8)0.0183 (8)−0.0013 (6)0.0002 (6)−0.0002 (6)
C320.0166 (7)0.0203 (8)0.0142 (8)−0.0013 (6)−0.0005 (6)−0.0012 (6)
C330.0169 (7)0.0156 (7)0.0180 (8)0.0001 (6)0.0009 (6)0.0010 (6)
C340.0201 (8)0.0183 (8)0.0209 (8)−0.0001 (6)0.0036 (6)0.0023 (6)
C350.0197 (7)0.0195 (8)0.0192 (8)−0.0014 (6)0.0004 (6)0.0006 (6)
C360.0236 (8)0.0195 (8)0.0189 (8)−0.0016 (6)−0.0012 (6)−0.0006 (6)
C370.0292 (9)0.0178 (8)0.0269 (9)0.0033 (6)0.0033 (7)−0.0044 (7)
C380.0344 (9)0.0206 (9)0.0309 (10)−0.0044 (7)0.0024 (7)−0.0109 (7)
C390.0228 (8)0.0258 (9)0.0222 (9)−0.0041 (6)0.0007 (6)−0.0042 (7)
C400.0191 (7)0.0195 (8)0.0160 (8)0.0003 (6)0.0011 (6)−0.0002 (6)
C410.0165 (7)0.0176 (8)0.0141 (8)−0.0011 (6)0.0013 (6)0.0012 (6)
C420.0158 (7)0.0166 (7)0.0164 (8)0.0003 (6)−0.0013 (6)−0.0002 (6)
C430.0201 (8)0.0190 (8)0.0240 (9)0.0024 (6)−0.0038 (6)−0.0027 (6)
C440.0205 (8)0.0218 (8)0.0168 (8)−0.0008 (6)0.0010 (6)−0.0011 (6)
C450.0178 (7)0.0219 (8)0.0187 (8)−0.0012 (6)0.0006 (6)0.0015 (6)
C460.0298 (9)0.0202 (8)0.0228 (9)0.0041 (7)0.0031 (7)0.0067 (7)
C470.0350 (9)0.0182 (8)0.0289 (10)−0.0038 (7)0.0079 (7)0.0022 (7)
C480.0257 (8)0.0233 (9)0.0252 (9)−0.0065 (6)0.0032 (7)−0.0016 (7)
C490.0183 (7)0.0206 (8)0.0172 (8)−0.0001 (6)0.0000 (6)0.0008 (6)
C500.0167 (7)0.0196 (8)0.0142 (8)−0.0003 (6)0.0017 (6)0.0002 (6)
C510.0157 (7)0.0173 (7)0.0173 (8)0.0001 (6)−0.0010 (6)0.0008 (6)
C520.0192 (7)0.0181 (8)0.0215 (8)−0.0003 (6)−0.0028 (6)0.0008 (6)
C530.0241 (8)0.0194 (8)0.0177 (8)−0.0010 (6)−0.0008 (6)−0.0002 (6)
C540.0201 (7)0.0187 (8)0.0197 (8)−0.0008 (6)0.0004 (6)0.0010 (6)

Geometric parameters (Å, °)

O1—C51.2353 (19)C15—C161.541 (2)
O2—C81.415 (2)C16—H16A0.9900
O2—H20.91 (3)C16—H16B0.9900
O3—C91.420 (2)C17—H17A0.9900
O3—H30.87 (3)C17—H17B0.9900
O4—C141.231 (2)C18—H18A0.9900
O5—C171.417 (2)C18—H18B0.9900
O5—H50.82 (3)C19—C201.395 (3)
O6—C181.424 (2)C19—H190.9500
O6—H60.90 (3)C20—C211.394 (3)
O7—C231.2331 (19)C20—H200.9500
O8—C261.431 (2)C21—C221.394 (2)
O8—H80.88 (3)C21—H210.9500
O9—C271.419 (2)C22—C231.429 (2)
O9—H90.84 (3)C23—C241.542 (2)
O10—C321.2307 (19)C24—C261.526 (2)
O11—C351.434 (2)C24—C271.536 (2)
O11—H110.85 (2)C24—C251.541 (2)
O12—C361.4227 (19)C25—H25A0.9900
O12—H120.84 (3)C25—H25B0.9900
O13—C411.2339 (19)C26—H26A0.9900
O14—C441.419 (2)C26—H26B0.9900
O14—H140.87 (3)C27—H27A0.9900
O15—C451.422 (2)C27—H27B0.9900
O15—H150.93 (3)C28—C291.394 (3)
O16—C501.2309 (19)C28—H280.9500
O17—C531.420 (2)C29—C301.397 (3)
O17—H170.88 (3)C29—H290.9500
O18—C541.434 (2)C30—C311.389 (2)
O18—H180.86 (2)C30—H300.9500
N1—C11.343 (2)C31—C321.434 (2)
N1—C41.378 (2)C32—C331.536 (2)
N1—C71.466 (2)C33—C361.526 (2)
N2—C101.344 (2)C33—C351.526 (2)
N2—C131.375 (2)C33—C341.545 (2)
N2—C161.463 (2)C34—H34A0.9900
N3—C191.343 (2)C34—H34B0.9900
N3—C221.375 (2)C35—H35A0.9900
N3—C251.462 (2)C35—H35B0.9900
N4—C281.348 (2)C36—H36A0.9900
N4—C311.376 (2)C36—H36B0.9900
N4—C341.465 (2)C37—C381.395 (3)
N5—C371.343 (2)C37—H370.9500
N5—C401.378 (2)C38—C391.393 (3)
N5—C431.464 (2)C38—H380.9500
N6—C461.342 (2)C39—C401.392 (2)
N6—C491.377 (2)C39—H390.9500
N6—C521.463 (2)C40—C411.430 (2)
C1—C21.397 (3)C41—C421.539 (2)
C1—H10.9500C42—C441.528 (2)
C2—C31.396 (2)C42—C451.531 (2)
C2—H2A0.9500C42—C431.541 (2)
C3—C41.394 (2)C43—H43A0.9900
C3—H3A0.9500C43—H43B0.9900
C4—C51.428 (2)C44—H44A0.9900
C5—C61.534 (2)C44—H44B0.9900
C6—C91.529 (2)C45—H45A0.9900
C6—C81.537 (2)C45—H45B0.9900
C6—C71.541 (2)C46—C471.394 (3)
C7—H7A0.9900C46—H460.9500
C7—H7B0.9900C47—C481.396 (3)
C8—H8A0.9900C47—H470.9500
C8—H8B0.9900C48—C491.393 (2)
C9—H9A0.9900C48—H480.9500
C9—H9B0.9900C49—C501.434 (2)
C10—C111.399 (3)C50—C511.540 (2)
C10—H100.9500C51—C541.528 (2)
C11—C121.394 (3)C51—C531.534 (2)
C11—H11A0.9500C51—C521.543 (2)
C12—C131.395 (2)C52—H52A0.9900
C12—H12A0.9500C52—H52B0.9900
C13—C141.426 (2)C53—H53A0.9900
C14—C151.542 (2)C53—H53B0.9900
C15—C181.524 (2)C54—H54A0.9900
C15—C171.536 (2)C54—H54B0.9900
C8—O2—H2105.5 (16)N3—C25—H25B111.0
C9—O3—H3113.3 (19)C24—C25—H25B111.0
C17—O5—H5106.1 (17)H25A—C25—H25B109.0
C18—O6—H6111.6 (16)O8—C26—C24108.75 (13)
C26—O8—H8109.1 (16)O8—C26—H26A109.9
C27—O9—H9109.5 (17)C24—C26—H26A109.9
C35—O11—H11110.4 (16)O8—C26—H26B109.9
C36—O12—H12105.8 (17)C24—C26—H26B109.9
C44—O14—H14108.5 (15)H26A—C26—H26B108.3
C45—O15—H15113.7 (18)O9—C27—C24111.68 (14)
C53—O17—H17106.2 (17)O9—C27—H27A109.3
C54—O18—H18109.3 (15)C24—C27—H27A109.3
C1—N1—C4110.24 (14)O9—C27—H27B109.3
C1—N1—C7135.72 (14)C24—C27—H27B109.3
C4—N1—C7114.04 (13)H27A—C27—H27B107.9
C10—N2—C13110.25 (14)N4—C28—C29107.43 (15)
C10—N2—C16135.44 (14)N4—C28—H28126.3
C13—N2—C16114.30 (13)C29—C28—H28126.3
C19—N3—C22110.47 (14)C28—C29—C30108.09 (15)
C19—N3—C25135.12 (14)C28—C29—H29126.0
C22—N3—C25114.40 (13)C30—C29—H29126.0
C28—N4—C31110.01 (14)C31—C30—C29106.82 (15)
C28—N4—C34135.19 (14)C31—C30—H30126.6
C31—N4—C34114.75 (13)C29—C30—H30126.6
C37—N5—C40110.07 (14)N4—C31—C30107.64 (14)
C37—N5—C43135.33 (14)N4—C31—C32108.52 (13)
C40—N5—C43114.59 (13)C30—C31—C32143.79 (15)
C46—N6—C49110.08 (14)O10—C32—C31128.86 (15)
C46—N6—C52135.20 (14)O10—C32—C33122.74 (14)
C49—N6—C52114.67 (13)C31—C32—C33108.37 (13)
N1—C1—C2107.41 (15)C36—C33—C35109.85 (12)
N1—C1—H1126.3C36—C33—C32109.91 (12)
C2—C1—H1126.3C35—C33—C32107.49 (13)
C3—C2—C1108.20 (15)C36—C33—C34112.62 (13)
C3—C2—H2A125.9C35—C33—C34111.67 (13)
C1—C2—H2A125.9C32—C33—C34105.07 (12)
C4—C3—C2106.65 (15)N4—C34—C33103.25 (12)
C4—C3—H3A126.7N4—C34—H34A111.1
C2—C3—H3A126.7C33—C34—H34A111.1
N1—C4—C3107.49 (14)N4—C34—H34B111.1
N1—C4—C5108.86 (14)C33—C34—H34B111.1
C3—C4—C5143.53 (15)H34A—C34—H34B109.1
O1—C5—C4128.96 (14)O11—C35—C33107.89 (12)
O1—C5—C6122.68 (14)O11—C35—H35A110.1
C4—C5—C6108.35 (13)C33—C35—H35A110.1
C9—C6—C5109.86 (13)O11—C35—H35B110.1
C9—C6—C8107.51 (13)C33—C35—H35B110.1
C5—C6—C8108.64 (13)H35A—C35—H35B108.4
C9—C6—C7113.67 (13)O12—C36—C33110.70 (13)
C5—C6—C7104.92 (13)O12—C36—H36A109.5
C8—C6—C7112.15 (14)C33—C36—H36A109.5
N1—C7—C6103.41 (12)O12—C36—H36B109.5
N1—C7—H7A111.1C33—C36—H36B109.5
C6—C7—H7A111.1H36A—C36—H36B108.1
N1—C7—H7B111.1N5—C37—C38107.29 (15)
C6—C7—H7B111.1N5—C37—H37126.4
H7A—C7—H7B109.0C38—C37—H37126.4
O2—C8—C6111.33 (14)C39—C38—C37108.50 (15)
O2—C8—H8A109.4C39—C38—H38125.8
C6—C8—H8A109.4C37—C38—H38125.8
O2—C8—H8B109.4C40—C39—C38106.47 (15)
C6—C8—H8B109.4C40—C39—H39126.8
H8A—C8—H8B108.0C38—C39—H39126.8
O3—C9—C6112.89 (13)N5—C40—C39107.67 (14)
O3—C9—H9A109.0N5—C40—C41108.64 (13)
C6—C9—H9A109.0C39—C40—C41143.69 (15)
O3—C9—H9B109.0O13—C41—C40128.95 (14)
C6—C9—H9B109.0O13—C41—C42122.72 (14)
H9A—C9—H9B107.8C40—C41—C42108.32 (13)
N2—C10—C11107.45 (15)C44—C42—C45108.87 (13)
N2—C10—H10126.3C44—C42—C41109.46 (12)
C11—C10—H10126.3C45—C42—C41107.85 (12)
C12—C11—C10107.97 (15)C44—C42—C43112.88 (13)
C12—C11—H11A126.0C45—C42—C43112.57 (13)
C10—C11—H11A126.0C41—C42—C43105.02 (12)
C11—C12—C13106.87 (15)N5—C43—C42103.40 (12)
C11—C12—H12A126.6N5—C43—H43A111.1
C13—C12—H12A126.6C42—C43—H43A111.1
N2—C13—C12107.45 (14)N5—C43—H43B111.1
N2—C13—C14109.24 (13)C42—C43—H43B111.1
C12—C13—C14143.30 (16)H43A—C43—H43B109.0
O4—C14—C13129.15 (15)O14—C44—C42111.44 (13)
O4—C14—C15122.96 (14)O14—C44—H44A109.3
C13—C14—C15107.88 (13)C42—C44—H44A109.3
C18—C15—C17108.93 (13)O14—C44—H44B109.3
C18—C15—C16112.08 (13)C42—C44—H44B109.3
C17—C15—C16113.26 (13)H44A—C44—H44B108.0
C18—C15—C14108.44 (13)O15—C45—C42110.90 (13)
C17—C15—C14108.88 (12)O15—C45—H45A109.5
C16—C15—C14105.06 (12)C42—C45—H45A109.5
N2—C16—C15103.49 (12)O15—C45—H45B109.5
N2—C16—H16A111.1C42—C45—H45B109.5
C15—C16—H16A111.1H45A—C45—H45B108.0
N2—C16—H16B111.1N6—C46—C47107.72 (15)
C15—C16—H16B111.1N6—C46—H46126.1
H16A—C16—H16B109.0C47—C46—H46126.1
O5—C17—C15111.92 (13)C46—C47—C48107.93 (15)
O5—C17—H17A109.2C46—C47—H47126.0
C15—C17—H17A109.2C48—C47—H47126.0
O5—C17—H17B109.2C49—C48—C47106.85 (15)
C15—C17—H17B109.2C49—C48—H48126.6
H17A—C17—H17B107.9C47—C48—H48126.6
O6—C18—C15108.77 (13)N6—C49—C48107.42 (14)
O6—C18—H18A109.9N6—C49—C50108.56 (13)
C15—C18—H18A109.9C48—C49—C50144.01 (15)
O6—C18—H18B109.9O16—C50—C49129.06 (14)
C15—C18—H18B109.9O16—C50—C51122.65 (14)
H18A—C18—H18B108.3C49—C50—C51108.30 (13)
N3—C19—C20107.30 (15)C54—C51—C53108.44 (13)
N3—C19—H19126.3C54—C51—C50108.67 (13)
C20—C19—H19126.3C53—C51—C50109.45 (12)
C21—C20—C19108.12 (15)C54—C51—C52112.50 (13)
C21—C20—H20125.9C53—C51—C52112.71 (13)
C19—C20—H20125.9C50—C51—C52104.93 (12)
C22—C21—C20106.90 (15)N6—C52—C51103.51 (12)
C22—C21—H21126.6N6—C52—H52A111.1
C20—C21—H21126.6C51—C52—H52A111.1
N3—C22—C21107.20 (15)N6—C52—H52B111.1
N3—C22—C23108.97 (13)C51—C52—H52B111.1
C21—C22—C23143.82 (16)H52A—C52—H52B109.0
O7—C23—C22129.30 (15)O17—C53—C51111.41 (13)
O7—C23—C24122.61 (14)O17—C53—H53A109.3
C22—C23—C24108.09 (13)C51—C53—H53A109.3
C26—C24—C27109.57 (13)O17—C53—H53B109.3
C26—C24—C25112.05 (13)C51—C53—H53B109.3
C27—C24—C25112.37 (13)H53A—C53—H53B108.0
C26—C24—C23107.96 (13)O18—C54—C51109.04 (13)
C27—C24—C23109.81 (12)O18—C54—H54A109.9
C25—C24—C23104.88 (12)C51—C54—H54A109.9
N3—C25—C24103.62 (12)O18—C54—H54B109.9
N3—C25—H25A111.0C51—C54—H54B109.9
C24—C25—H25A111.0H54A—C54—H54B108.3
C4—N1—C1—C20.14 (19)C31—N4—C28—C29−0.26 (19)
C7—N1—C1—C2179.88 (18)C34—N4—C28—C29−177.52 (17)
N1—C1—C2—C3−0.5 (2)N4—C28—C29—C300.1 (2)
C1—C2—C3—C40.7 (2)C28—C29—C30—C310.2 (2)
C1—N1—C4—C30.30 (19)C28—N4—C31—C300.36 (19)
C7—N1—C4—C3−179.50 (14)C34—N4—C31—C30178.23 (14)
C1—N1—C4—C5−176.64 (14)C28—N4—C31—C32−177.71 (14)
C7—N1—C4—C53.56 (19)C34—N4—C31—C320.16 (19)
C2—C3—C4—N1−0.62 (19)C29—C30—C31—N4−0.31 (19)
C2—C3—C4—C5174.5 (2)C29—C30—C31—C32176.6 (2)
N1—C4—C5—O1179.58 (16)N4—C31—C32—O10179.08 (16)
C3—C4—C5—O14.5 (4)C30—C31—C32—O102.2 (4)
N1—C4—C5—C60.81 (18)N4—C31—C32—C331.16 (17)
C3—C4—C5—C6−174.3 (2)C30—C31—C32—C33−175.7 (2)
O1—C5—C6—C954.1 (2)O10—C32—C33—C3658.6 (2)
C4—C5—C6—C9−127.00 (14)C31—C32—C33—C36−123.34 (14)
O1—C5—C6—C8−63.2 (2)O10—C32—C33—C35−60.95 (19)
C4—C5—C6—C8115.65 (15)C31—C32—C33—C35117.13 (14)
O1—C5—C6—C7176.68 (15)O10—C32—C33—C34179.98 (14)
C4—C5—C6—C7−4.45 (17)C31—C32—C33—C34−1.93 (17)
C1—N1—C7—C6174.07 (18)C28—N4—C34—C33175.80 (17)
C4—N1—C7—C6−6.20 (19)C31—N4—C34—C33−1.37 (18)
C9—C6—C7—N1126.15 (14)C36—C33—C34—N4121.53 (14)
C5—C6—C7—N16.10 (17)C35—C33—C34—N4−114.32 (14)
C8—C6—C7—N1−111.65 (15)C32—C33—C34—N41.91 (16)
C9—C6—C8—O2−178.12 (13)C36—C33—C35—O11−168.99 (12)
C5—C6—C8—O2−59.28 (17)C32—C33—C35—O11−49.42 (16)
C7—C6—C8—O256.23 (18)C34—C33—C35—O1165.33 (16)
C5—C6—C9—O350.03 (17)C35—C33—C36—O12179.10 (12)
C8—C6—C9—O3168.08 (13)C32—C33—C36—O1261.02 (17)
C7—C6—C9—O3−67.18 (18)C34—C33—C36—O12−55.75 (17)
C13—N2—C10—C111.16 (19)C40—N5—C37—C38−0.29 (19)
C16—N2—C10—C11−179.96 (17)C43—N5—C37—C38−179.10 (17)
N2—C10—C11—C12−1.0 (2)N5—C37—C38—C390.0 (2)
C10—C11—C12—C130.4 (2)C37—C38—C39—C400.2 (2)
C10—N2—C13—C12−0.91 (19)C37—N5—C40—C390.44 (19)
C16—N2—C13—C12179.94 (14)C43—N5—C40—C39179.52 (14)
C10—N2—C13—C14178.12 (14)C37—N5—C40—C41−179.23 (14)
C16—N2—C13—C14−1.02 (19)C43—N5—C40—C41−0.15 (19)
C11—C12—C13—N20.29 (19)C38—C39—C40—N5−0.41 (19)
C11—C12—C13—C14−178.2 (2)C38—C39—C40—C41179.1 (2)
N2—C13—C14—O4−178.10 (16)N5—C40—C41—O13−179.63 (15)
C12—C13—C14—O40.4 (4)C39—C40—C41—O130.9 (4)
N2—C13—C14—C151.49 (17)N5—C40—C41—C42−1.05 (17)
C12—C13—C14—C15179.9 (2)C39—C40—C41—C42179.5 (2)
O4—C14—C15—C1858.23 (19)O13—C41—C42—C44−58.11 (19)
C13—C14—C15—C18−121.39 (14)C40—C41—C42—C44123.21 (14)
O4—C14—C15—C17−60.2 (2)O13—C41—C42—C4560.19 (19)
C13—C14—C15—C17120.22 (14)C40—C41—C42—C45−118.50 (14)
O4—C14—C15—C16178.23 (14)O13—C41—C42—C43−179.55 (15)
C13—C14—C15—C16−1.39 (17)C40—C41—C42—C431.76 (16)
C10—N2—C16—C15−178.75 (17)C37—N5—C43—C42−179.98 (18)
C13—N2—C16—C150.10 (18)C40—N5—C43—C421.25 (18)
C18—C15—C16—N2118.34 (14)C44—C42—C43—N5−120.92 (14)
C17—C15—C16—N2−117.93 (14)C45—C42—C43—N5115.33 (14)
C14—C15—C16—N20.78 (16)C41—C42—C43—N5−1.74 (16)
C18—C15—C17—O5−176.35 (13)C45—C42—C44—O14−175.90 (12)
C16—C15—C17—O558.21 (17)C41—C42—C44—O14−58.24 (17)
C14—C15—C17—O5−58.27 (17)C43—C42—C44—O1458.33 (17)
C17—C15—C18—O6166.48 (12)C44—C42—C45—O15168.90 (12)
C16—C15—C18—O6−67.40 (16)C41—C42—C45—O1550.23 (16)
C14—C15—C18—O648.12 (16)C43—C42—C45—O15−65.15 (16)
C22—N3—C19—C20−0.12 (19)C49—N6—C46—C470.03 (19)
C25—N3—C19—C20−179.88 (17)C52—N6—C46—C47177.21 (17)
N3—C19—C20—C210.3 (2)N6—C46—C47—C480.1 (2)
C19—C20—C21—C22−0.4 (2)C46—C47—C48—C49−0.2 (2)
C19—N3—C22—C21−0.14 (19)C46—N6—C49—C48−0.13 (19)
C25—N3—C22—C21179.66 (14)C52—N6—C49—C48−177.95 (14)
C19—N3—C22—C23−179.59 (14)C46—N6—C49—C50179.19 (13)
C25—N3—C22—C230.22 (19)C52—N6—C49—C501.38 (18)
C20—C21—C22—N30.35 (19)C47—C48—C49—N60.18 (19)
C20—C21—C22—C23179.5 (2)C47—C48—C49—C50−178.7 (2)
N3—C22—C23—O7−179.57 (16)N6—C49—C50—O16178.45 (16)
C21—C22—C23—O71.3 (4)C48—C49—C50—O16−2.6 (4)
N3—C22—C23—C241.09 (17)N6—C49—C50—C51−1.64 (17)
C21—C22—C23—C24−178.0 (2)C48—C49—C50—C51177.3 (2)
O7—C23—C24—C26−61.64 (19)O16—C50—C51—C5460.67 (19)
C22—C23—C24—C26117.76 (14)C49—C50—C51—C54−119.24 (14)
O7—C23—C24—C2757.8 (2)O16—C50—C51—C53−57.58 (19)
C22—C23—C24—C27−122.83 (14)C49—C50—C51—C53122.50 (14)
O7—C23—C24—C25178.73 (14)O16—C50—C51—C52−178.78 (14)
C22—C23—C24—C25−1.88 (17)C49—C50—C51—C521.31 (16)
C19—N3—C25—C24178.35 (17)C46—N6—C52—C51−177.59 (17)
C22—N3—C25—C24−1.40 (17)C49—N6—C52—C51−0.50 (18)
C26—C24—C25—N3−114.97 (14)C54—C51—C52—N6117.47 (14)
C27—C24—C25—N3121.14 (14)C53—C51—C52—N6−119.54 (14)
C23—C24—C25—N31.90 (16)C50—C51—C52—N6−0.51 (16)
C27—C24—C26—O8−168.30 (12)C54—C51—C53—O17179.10 (13)
C25—C24—C26—O866.26 (16)C50—C51—C53—O17−62.50 (17)
C23—C24—C26—O8−48.74 (16)C52—C51—C53—O1753.87 (17)
C26—C24—C27—O9176.49 (13)C53—C51—C54—O18167.38 (12)
C25—C24—C27—O9−58.26 (17)C50—C51—C54—O1848.49 (16)
C23—C24—C27—O958.07 (17)C52—C51—C54—O18−67.26 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.91 (3)1.85 (3)2.7513 (19)172 (2)
O3—H3···O40.87 (3)1.95 (3)2.7612 (17)154 (3)
O5—H5···O6ii0.82 (3)1.98 (3)2.7776 (17)166 (2)
O6—H6···O1iii0.90 (3)1.80 (3)2.6801 (16)168 (2)
O8—H8···O160.88 (3)1.85 (3)2.7219 (16)168 (2)
O9—H9···O11iv0.84 (3)1.96 (3)2.7841 (18)168 (2)
O11—H11···O13v0.85 (2)1.92 (2)2.7239 (16)157 (2)
O12—H12···O80.84 (3)2.00 (3)2.8186 (18)167 (2)
O14—H14···O180.87 (3)1.95 (3)2.8063 (18)168 (2)
O15—H15···O10vi0.93 (3)1.86 (3)2.7290 (16)155 (3)
O17—H17···O15v0.88 (3)1.96 (3)2.8144 (18)166 (3)
O18—H18···O7vii0.86 (2)1.92 (2)2.7579 (17)168 (2)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2; (iii) x+1, y, z; (iv) x, y, z+1; (v) x, y, z−1; (vi) x−1, y, z+1; (vii) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2763).

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