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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1472.
Published online 2010 May 26. doi:  10.1107/S1600536810018015
PMCID: PMC2979597

Methyl 3-(1H-indole-3-carboxamido)propionate hemihydrate

Abstract

The title compound, C13H14N2O3·0.5H2O, was synthesized by the condensation of methyl 3-amino­propionate with 3-trichloro­acetyl­indole. The two organic mol­ecules in the asymmetric unit are both close to planar, with r.m.s. deviations from the best fit plane through all of the non-H atoms of 0.004 (2) Å for mol­ecule A and 0.006 (1) Å for mol­ecule B. Also, the five- and six-membered rings of the indole systems are inclined at 1.67 (8) and 1.50 (8)° in mol­ecules A and B, respectively. In the crystal structure, the organic molecules are connected by inter­molecular N—H(...)O hydrogen bonds, forming chains. O—H(...)O and N—H(...)O hydrogen-bond inter­actions involving the water molecules inter­link these chains, forming double chains approximately parallel to the a axis.

Related literature

For the bioactivity of indole derivatives, see: Fabio et al. (2007 [triangle]); Sharma et al. (2004 [triangle]). For related structures, see: Huang et al. (2009 [triangle]); Siddiquee et al. (2009 [triangle]). For reference structural data, see Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1472-scheme1.jpg

Experimental

Crystal data

  • C13H14N2O3·0.5H2O
  • M r = 255.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1472-efi1.jpg
  • a = 10.8220 (13) Å
  • b = 9.7668 (12) Å
  • c = 23.623 (3) Å
  • β = 92.422 (2)°
  • V = 2494.6 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 173 K
  • 0.46 × 0.43 × 0.39 mm

Data collection

  • Bruker SMART 1K CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.955, T max = 0.962
  • 13021 measured reflections
  • 5484 independent reflections
  • 4349 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.126
  • S = 1.07
  • 5484 reflections
  • 336 parameters
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 1999 [triangle]); cell refinement: SAINT-Plus (Bruker, 1999 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810018015/sj2794sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018015/sj2794Isup2.hkl

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

Acknowledgments

We thank the Natural Science Foundation of Guangdong Province, China (No. 06300581) for generously supporting this study.

supplementary crystallographic information

Comment

Many indole derivatives show important bioactivity, acting as metabotropic receptor antagonists (Fabio et al., 2007) and showing protein kinase inhibiting activity (Sharma et al., 2004). This is the reason they have attracted our interest and the title compound is related to our previous structural investigations of methyl 3-(1-Butyl-1H-indole-3-carbonyl)aminopropionate (Huang et al., 2009).

The asymmetric unit of the title compound comprises two substituted indole molecules, A & B and a solvent water molecule, Fig. 1. The organic molecules are each reasonably planar with rms deviations from the best fit plane through all of the non hydrogen atoms of 0.004 (2) Å for A and -0.006 (1) Å for B. Also the five and six-membered rings of the indole systems are inclined at 1.67 (8) ° and 1.50 (8) ° in A and B respectively. Bond lengths in both molecules are unexceptional (Allen et al., 1987) and are comparable to those found in similar structures (Huang et al., 2009; Siddiquee et al., 2009).

In the crystal structure, molecules of the organic compound are linked through N—H···O H-bonds to form dimers that are connected by another N—H···O H-bonds to generate chains, and the O—H(W)···O and N—H···O(W) H-bond interactions link these chains to form double-chains extending to the a axis (Table 1, Fig. 2).

Experimental

The hydrochloride salt of methyl 3-aminopropionate (0.70 g, 5 mmol) and 3-trichloroacetylindole (1.32 g, 5 mmol) were added to acetonitrile (10 ml), followed by the dropwise addition of triethylamine (1.2 ml). The mixture was stirred at room temperature for 16 h and then poured into water. After filtration, the precipitate was collected as a yellow solid. The impure product was dissolved in EtOH at room temperature. Light yellow monoclinic crystals suitable for X-ray analysis (m.p. 409 K, 86.2% yield) grew over a period of one week when the solution was exposed to the air.

Refinement

All non-H atoms were refined with anisotropic displacement parameters. The H atoms bound to C and N were positioned geometrically [C—H = 0.99Å for CH2, 0.98Å for CH3, 0.95Å for CH(aromatic) and N—H = 0.88 Å] and refined using a riding model, with Uiso = 1.2Ueq (1.5Ueq for the methyl group) of the parent atom. The water H atoms were located in a difference Fourier map and were constrained in these positions with O—H = 0.8497 and 0.8533, and with Uiso = 1.5Ueq(O).

Figures

Fig. 1.
The asymmetric unit of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
Crystal packing of the hydrate (viewed along the c axis). Dashed lines indicate hydrogen bonds.

Crystal data

C13H14N2O3·0.5H2OF(000) = 1080
Mr = 255.27Dx = 1.359 Mg m3
Monoclinic, P21/nMelting point: 409 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 10.8220 (13) ÅCell parameters from 7482 reflections
b = 9.7668 (12) Åθ = 2.3–27.1°
c = 23.623 (3) ŵ = 0.10 mm1
β = 92.422 (2)°T = 173 K
V = 2494.6 (5) Å3Block, yellow
Z = 80.46 × 0.43 × 0.39 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer5484 independent reflections
Radiation source: fine-focus sealed tube4349 reflections with I > 2σ(I)
graphiteRint = 0.036
[var phi] and ω scansθmax = 27.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→11
Tmin = 0.955, Tmax = 0.962k = −8→12
13021 measured reflectionsl = −30→30

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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0626P)2 + 0.3718P] where P = (Fo2 + 2Fc2)/3
5484 reflections(Δ/σ)max = 0.001
336 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = −0.23 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
C10.80813 (13)−0.08599 (15)0.03833 (6)0.0318 (3)
H10.8269−0.06660.00020.038*
C20.71838 (12)−0.02181 (14)0.06810 (6)0.0272 (3)
C30.72133 (12)−0.08192 (14)0.12390 (6)0.0275 (3)
C40.65431 (14)−0.06387 (16)0.17297 (6)0.0341 (3)
H40.59170.00410.17430.041*
C50.68093 (15)−0.14651 (17)0.21922 (6)0.0398 (4)
H50.6352−0.13560.25240.048*
C60.77349 (16)−0.24579 (17)0.21840 (7)0.0421 (4)
H60.7892−0.30120.25100.051*
C70.84253 (14)−0.26528 (16)0.17145 (7)0.0373 (3)
H70.9061−0.33230.17100.045*
C80.81497 (12)−0.18210 (14)0.12439 (6)0.0297 (3)
C90.62911 (13)0.08453 (15)0.04984 (6)0.0305 (3)
C100.53881 (13)0.24140 (15)−0.01892 (6)0.0311 (3)
H10A0.55360.32260.00550.037*
H10B0.45440.2074−0.01250.037*
C110.54663 (13)0.28339 (15)−0.08026 (6)0.0321 (3)
H11A0.63160.3150−0.08720.039*
H11B0.52860.2034−0.10500.039*
C120.45597 (13)0.39641 (15)−0.09478 (6)0.0308 (3)
C130.39062 (16)0.55673 (18)−0.16381 (7)0.0433 (4)
H13A0.39590.6307−0.13580.065*
H13B0.30560.5222−0.16700.065*
H13C0.41450.5917−0.20070.065*
C140.29377 (13)0.36840 (16)0.06182 (6)0.0341 (3)
H140.31020.36920.02260.041*
C150.21024 (12)0.45232 (14)0.08725 (6)0.0290 (3)
C160.21441 (12)0.41712 (14)0.14649 (6)0.0284 (3)
C170.15418 (14)0.46235 (16)0.19450 (6)0.0354 (3)
H170.09280.53170.19130.042*
C180.18574 (16)0.40417 (17)0.24654 (7)0.0432 (4)
H180.14460.43350.27910.052*
C190.27677 (16)0.30334 (18)0.25209 (7)0.0441 (4)
H190.29770.26690.28850.053*
C200.33663 (15)0.25580 (17)0.20592 (7)0.0399 (4)
H200.39810.18660.20970.048*
C210.30395 (13)0.31267 (15)0.15322 (6)0.0319 (3)
C220.13786 (12)0.56060 (14)0.05926 (6)0.0290 (3)
C230.08226 (13)0.69102 (15)−0.02576 (6)0.0301 (3)
H23A0.10480.7807−0.00880.036*
H23B−0.00720.6763−0.02110.036*
C240.10799 (13)0.69297 (15)−0.08814 (6)0.0328 (3)
H24A0.19720.7095−0.09290.039*
H24B0.08660.6029−0.10510.039*
C250.03353 (13)0.80346 (15)−0.11816 (6)0.0310 (3)
C26−0.01206 (18)0.91058 (19)−0.20573 (7)0.0497 (4)
H26A−0.10050.8992−0.19970.075*
H26B0.00330.8978−0.24600.075*
H26C0.01391.0028−0.19400.075*
N10.86589 (11)−0.18166 (13)0.07191 (5)0.0333 (3)
H1A0.9265−0.23510.06170.040*
N20.62849 (11)0.13484 (13)−0.00271 (5)0.0317 (3)
H20.68110.1044−0.02720.038*
N30.34897 (12)0.28454 (14)0.10095 (5)0.0375 (3)
H30.40480.22200.09400.045*
N40.15203 (11)0.58337 (12)0.00368 (5)0.0320 (3)
H4A0.20390.5327−0.01500.038*
O10.55464 (11)0.12826 (13)0.08443 (5)0.0466 (3)
O20.37724 (10)0.43840 (12)−0.06434 (4)0.0405 (3)
O30.47321 (10)0.44687 (12)−0.14607 (4)0.0393 (3)
O40.06489 (10)0.63299 (11)0.08581 (4)0.0396 (3)
O5−0.03955 (10)0.87601 (12)−0.09532 (4)0.0402 (3)
O60.05767 (10)0.80986 (12)−0.17246 (4)0.0413 (3)
O1W0.20002 (11)0.89955 (13)0.09463 (5)0.0507 (3)
H1B0.15370.83010.09940.076*
H1C0.15920.97040.10310.076*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0314 (7)0.0312 (7)0.0330 (7)0.0062 (6)0.0043 (5)0.0008 (6)
C20.0245 (6)0.0256 (6)0.0314 (7)0.0024 (5)0.0014 (5)−0.0018 (5)
C30.0257 (6)0.0249 (6)0.0317 (7)0.0006 (5)−0.0005 (5)−0.0032 (5)
C40.0347 (7)0.0341 (8)0.0338 (7)0.0017 (6)0.0035 (6)−0.0060 (6)
C50.0477 (9)0.0418 (9)0.0303 (7)−0.0043 (7)0.0050 (6)−0.0012 (6)
C60.0537 (10)0.0372 (8)0.0349 (8)−0.0022 (7)−0.0066 (7)0.0058 (7)
C70.0395 (8)0.0307 (7)0.0411 (8)0.0050 (6)−0.0056 (6)0.0029 (6)
C80.0279 (7)0.0270 (7)0.0341 (7)0.0006 (5)−0.0005 (5)−0.0024 (6)
C90.0288 (7)0.0297 (7)0.0331 (7)0.0048 (6)−0.0001 (5)−0.0024 (6)
C100.0319 (7)0.0298 (7)0.0315 (7)0.0067 (6)−0.0002 (5)−0.0002 (6)
C110.0298 (7)0.0335 (7)0.0329 (7)0.0029 (6)0.0000 (6)−0.0017 (6)
C120.0311 (7)0.0322 (7)0.0289 (7)−0.0009 (6)−0.0006 (5)−0.0002 (6)
C130.0491 (9)0.0457 (9)0.0353 (8)0.0135 (8)0.0020 (7)0.0086 (7)
C140.0337 (7)0.0351 (8)0.0337 (7)0.0100 (6)0.0053 (6)0.0028 (6)
C150.0259 (6)0.0268 (7)0.0345 (7)0.0041 (5)0.0027 (5)0.0002 (6)
C160.0268 (6)0.0243 (6)0.0341 (7)0.0008 (5)0.0004 (5)0.0001 (5)
C170.0389 (8)0.0294 (7)0.0381 (8)0.0072 (6)0.0045 (6)−0.0022 (6)
C180.0561 (10)0.0393 (9)0.0347 (8)0.0068 (7)0.0078 (7)−0.0024 (7)
C190.0588 (10)0.0387 (9)0.0344 (8)0.0063 (8)−0.0015 (7)0.0052 (7)
C200.0431 (8)0.0356 (8)0.0409 (8)0.0106 (7)−0.0001 (7)0.0071 (7)
C210.0304 (7)0.0303 (7)0.0352 (7)0.0044 (6)0.0033 (6)0.0009 (6)
C220.0263 (6)0.0261 (7)0.0348 (7)0.0031 (5)0.0018 (5)0.0007 (6)
C230.0299 (7)0.0281 (7)0.0324 (7)0.0049 (6)0.0010 (5)0.0012 (6)
C240.0331 (7)0.0315 (7)0.0341 (7)0.0051 (6)0.0048 (6)−0.0007 (6)
C250.0335 (7)0.0303 (7)0.0293 (7)−0.0022 (6)0.0032 (5)−0.0012 (6)
C260.0705 (12)0.0463 (10)0.0321 (8)0.0024 (9)−0.0013 (8)0.0089 (7)
N10.0307 (6)0.0316 (6)0.0378 (7)0.0109 (5)0.0052 (5)0.0001 (5)
N20.0305 (6)0.0324 (6)0.0323 (6)0.0086 (5)0.0027 (5)0.0000 (5)
N30.0371 (7)0.0375 (7)0.0381 (7)0.0170 (6)0.0061 (5)0.0035 (5)
N40.0322 (6)0.0307 (6)0.0333 (6)0.0102 (5)0.0046 (5)0.0017 (5)
O10.0473 (6)0.0551 (7)0.0382 (6)0.0289 (6)0.0098 (5)0.0055 (5)
O20.0419 (6)0.0452 (6)0.0348 (5)0.0147 (5)0.0070 (4)0.0054 (5)
O30.0441 (6)0.0426 (6)0.0314 (5)0.0128 (5)0.0050 (4)0.0057 (5)
O40.0419 (6)0.0392 (6)0.0381 (6)0.0197 (5)0.0084 (4)0.0045 (5)
O50.0467 (6)0.0393 (6)0.0350 (5)0.0148 (5)0.0056 (5)0.0025 (5)
O60.0523 (7)0.0422 (6)0.0298 (5)0.0042 (5)0.0061 (5)0.0037 (5)
O1W0.0556 (7)0.0471 (7)0.0506 (7)0.0176 (6)0.0152 (6)0.0011 (6)

Geometric parameters (Å, °)

C1—N11.3606 (18)C15—C161.4399 (19)
C1—C21.3744 (19)C15—C221.4579 (19)
C1—H10.9500C16—C171.403 (2)
C2—C31.4421 (19)C16—C211.4114 (19)
C2—C91.4706 (19)C17—C181.384 (2)
C3—C41.404 (2)C17—H170.9500
C3—C81.4083 (19)C18—C191.395 (2)
C4—C51.379 (2)C18—H180.9500
C4—H40.9500C19—C201.373 (2)
C5—C61.395 (2)C19—H190.9500
C5—H50.9500C20—C211.395 (2)
C6—C71.376 (2)C20—H200.9500
C6—H60.9500C21—N31.3743 (19)
C7—C81.399 (2)C22—O41.2485 (17)
C7—H70.9500C22—N41.3467 (18)
C8—N11.3779 (19)C23—N41.4543 (17)
C9—O11.2470 (17)C23—C241.511 (2)
C9—N21.3348 (18)C23—H23A0.9900
C10—N21.4630 (17)C23—H23B0.9900
C10—C111.512 (2)C24—C251.506 (2)
C10—H10A0.9900C24—H24A0.9900
C10—H10B0.9900C24—H24B0.9900
C11—C121.507 (2)C25—O51.2062 (18)
C11—H11A0.9900C25—O61.3212 (17)
C11—H11B0.9900C26—O61.451 (2)
C12—O21.2095 (17)C26—H26A0.9800
C12—O31.3285 (17)C26—H26B0.9800
C13—O31.4470 (19)C26—H26C0.9800
C13—H13A0.9800N1—H1A0.8800
C13—H13B0.9800N2—H20.8800
C13—H13C0.9800N3—H30.8800
C14—N31.3548 (19)N4—H4A0.8800
C14—C151.377 (2)O1W—H1B0.8533
C14—H140.9500O1W—H1C0.8497
N1—C1—C2109.39 (12)C21—C16—C15105.98 (12)
N1—C1—H1125.3C18—C17—C16118.89 (14)
C2—C1—H1125.3C18—C17—H17120.6
C1—C2—C3107.05 (12)C16—C17—H17120.6
C1—C2—C9129.92 (13)C17—C18—C19121.33 (15)
C3—C2—C9122.99 (12)C17—C18—H18119.3
C4—C3—C8118.49 (13)C19—C18—H18119.3
C4—C3—C2135.33 (13)C20—C19—C18121.28 (15)
C8—C3—C2106.17 (12)C20—C19—H19119.4
C5—C4—C3118.86 (14)C18—C19—H19119.4
C5—C4—H4120.6C19—C20—C21117.64 (14)
C3—C4—H4120.6C19—C20—H20121.2
C4—C5—C6121.47 (15)C21—C20—H20121.2
C4—C5—H5119.3N3—C21—C20129.50 (13)
C6—C5—H5119.3N3—C21—C16108.12 (12)
C7—C6—C5121.46 (15)C20—C21—C16122.37 (14)
C7—C6—H6119.3O4—C22—N4119.79 (12)
C5—C6—H6119.3O4—C22—C15121.47 (13)
C6—C7—C8117.08 (14)N4—C22—C15118.73 (12)
C6—C7—H7121.5N4—C23—C24111.22 (11)
C8—C7—H7121.5N4—C23—H23A109.4
N1—C8—C7129.56 (13)C24—C23—H23A109.4
N1—C8—C3107.79 (12)N4—C23—H23B109.4
C7—C8—C3122.63 (14)C24—C23—H23B109.4
O1—C9—N2120.34 (13)H23A—C23—H23B108.0
O1—C9—C2118.97 (13)C25—C24—C23110.56 (11)
N2—C9—C2120.68 (12)C25—C24—H24A109.5
N2—C10—C11112.37 (11)C23—C24—H24A109.5
N2—C10—H10A109.1C25—C24—H24B109.5
C11—C10—H10A109.1C23—C24—H24B109.5
N2—C10—H10B109.1H24A—C24—H24B108.1
C11—C10—H10B109.1O5—C25—O6124.53 (13)
H10A—C10—H10B107.9O5—C25—C24123.92 (13)
C12—C11—C10110.78 (12)O6—C25—C24111.54 (12)
C12—C11—H11A109.5O6—C26—H26A109.5
C10—C11—H11A109.5O6—C26—H26B109.5
C12—C11—H11B109.5H26A—C26—H26B109.5
C10—C11—H11B109.5O6—C26—H26C109.5
H11A—C11—H11B108.1H26A—C26—H26C109.5
O2—C12—O3123.10 (13)H26B—C26—H26C109.5
O2—C12—C11125.54 (13)C1—N1—C8109.60 (11)
O3—C12—C11111.36 (12)C1—N1—H1A125.2
O3—C13—H13A109.5C8—N1—H1A125.2
O3—C13—H13B109.5C9—N2—C10118.86 (11)
H13A—C13—H13B109.5C9—N2—H2120.6
O3—C13—H13C109.5C10—N2—H2120.6
H13A—C13—H13C109.5C14—N3—C21109.23 (12)
H13B—C13—H13C109.5C14—N3—H3125.4
N3—C14—C15109.93 (13)C21—N3—H3125.4
N3—C14—H14125.0C22—N4—C23120.49 (11)
C15—C14—H14125.0C22—N4—H4A119.8
C14—C15—C16106.73 (12)C23—N4—H4A119.8
C14—C15—C22125.74 (13)C12—O3—C13115.49 (12)
C16—C15—C22127.45 (12)C25—O6—C26116.00 (12)
C17—C16—C21118.46 (13)H1B—O1W—H1C107.6
C17—C16—C15135.56 (13)
N1—C1—C2—C30.15 (16)C16—C17—C18—C190.8 (3)
N1—C1—C2—C9−177.67 (14)C17—C18—C19—C20−1.5 (3)
C1—C2—C3—C4−179.04 (15)C18—C19—C20—C210.5 (3)
C9—C2—C3—C4−1.0 (2)C19—C20—C21—N3179.75 (16)
C1—C2—C3—C8−0.29 (15)C19—C20—C21—C161.1 (2)
C9—C2—C3—C8177.72 (12)C17—C16—C21—N3179.37 (13)
C8—C3—C4—C5−1.3 (2)C15—C16—C21—N3−1.26 (16)
C2—C3—C4—C5177.35 (15)C17—C16—C21—C20−1.7 (2)
C3—C4—C5—C60.8 (2)C15—C16—C21—C20177.67 (14)
C4—C5—C6—C70.2 (2)C14—C15—C22—O4−179.26 (14)
C5—C6—C7—C8−0.6 (2)C16—C15—C22—O4−3.1 (2)
C6—C7—C8—N1−177.99 (14)C14—C15—C22—N4−0.2 (2)
C6—C7—C8—C30.1 (2)C16—C15—C22—N4175.97 (13)
C4—C3—C8—N1179.32 (12)N4—C23—C24—C25179.09 (12)
C2—C3—C8—N10.31 (15)C23—C24—C25—O5−2.6 (2)
C4—C3—C8—C70.9 (2)C23—C24—C25—O6177.96 (12)
C2—C3—C8—C7−178.12 (13)C2—C1—N1—C80.05 (16)
C1—C2—C9—O1179.73 (15)C7—C8—N1—C1178.05 (15)
C3—C2—C9—O12.2 (2)C3—C8—N1—C1−0.23 (16)
C1—C2—C9—N2−1.0 (2)O1—C9—N2—C10−0.2 (2)
C3—C2—C9—N2−178.56 (12)C2—C9—N2—C10−179.46 (12)
N2—C10—C11—C12−178.09 (12)C11—C10—N2—C9−177.74 (12)
C10—C11—C12—O2−8.0 (2)C15—C14—N3—C21−0.72 (18)
C10—C11—C12—O3171.58 (12)C20—C21—N3—C14−177.58 (16)
N3—C14—C15—C16−0.08 (17)C16—C21—N3—C141.25 (17)
N3—C14—C15—C22176.72 (13)O4—C22—N4—C23−0.5 (2)
C14—C15—C16—C17−179.97 (16)C15—C22—N4—C23−179.56 (13)
C22—C15—C16—C173.3 (3)C24—C23—N4—C22−177.04 (12)
C14—C15—C16—C210.82 (16)O2—C12—O3—C13−0.2 (2)
C22—C15—C16—C21−175.91 (14)C11—C12—O3—C13−179.74 (13)
C21—C16—C17—C180.7 (2)O5—C25—O6—C26−1.2 (2)
C15—C16—C17—C18−178.40 (16)C24—C25—O6—C26178.26 (13)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O4i0.882.042.8219 (15)148
N2—H2···O1Wii0.882.092.9348 (17)161
N3—H3···O10.881.882.7404 (16)164
N4—H4A···O20.882.433.2952 (15)167
O1W—H1B···O40.852.172.9890 (18)161
O1W—H1C···O5iii0.851.982.7970 (16)160

Symmetry codes: (i) x+1, y−1, z; (ii) −x+1, −y+1, −z; (iii) −x, −y+2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2794).

References

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