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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o105–o106.
Published online 2009 December 12. doi:  10.1107/S1600536809052465
PMCID: PMC2980105

3,4,5-Trihydr­oxy-N′-(1H-indol-2-ylmethyl­idene)benzohydrazide–1H-indole-2-carbaldehyde azine–methanol (2/1/2)

Abstract

The title compound, 2C16H13N3O4·C18H14N4·2CH4O, was crystallized from the reaction between 3,4,5-trihydroxy­benzoyl­hydrazine and indole-2-carbaldehyde in a mixture of ethanol and methanol. The compound is a stoichiometric 2:1 cocrystal of the methanol-solvated reaction product, 3,4,5-trihydr­oxy-N′-(1H-indol-2-ylmethyl­idene)benzohydrazide and 1H-indole-2-carbaldehyde azine that arose unexpectedly during the synthesis. The former mol­ecules are linked by O—H(...)O hydrogen bonds and also by π–π stacking inter­actions between benzoyl­hydrazide rings into a two-dimensional network. The methanol solvent mol­ecules are hydrogen bonded to this network. The centrosymmetric azine mol­ecules are not engaged in hydrogen bonding.

Related literature

For the crystal structures of some compounds similar to 3,4,5-trihydr­oxy-N′-[(1H-indol-2-yl)methyl­idene]benzoyl­hydrazide, see: Khaledi et al. (2008a [triangle],b [triangle], 2009a [triangle],b [triangle]). For the structure of 1H-indole-2-carbaldehyde azine, see: Rizal et al. (2008 [triangle]). For the biological activity of gallic acid (3,4,5-trihydroxybenzoic acid) derivatives see: Arunkumar et al. (2006 [triangle]); Saxena et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o105-scheme1.jpg

Experimental

Crystal data

  • 2C16H13N3O4·C18H14N4·2CH4O
  • M r = 973.00
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o105-efi1.jpg
  • a = 7.4642 (15) Å
  • b = 12.791 (2) Å
  • c = 25.079 (5) Å
  • α = 95.918 (3)°
  • β = 95.166 (4)°
  • γ = 101.451 (4)°
  • V = 2319.3 (8) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 100 K
  • 0.50 × 0.12 × 0.03 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.952, T max = 0.997
  • 10985 measured reflections
  • 7939 independent reflections
  • 4029 reflections with I > 2σ(I)
  • R int = 0.054

Refinement

  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.153
  • S = 0.98
  • 7939 reflections
  • 693 parameters
  • 14 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]) and Mercury (Macrae et al., 2008 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052465/om2302sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052465/om2302Isup2.hkl

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

Acknowledgments

The authors thank the University of Malaya for funding this study (FRGS grant FP009/2008 C).

supplementary crystallographic information

Comment

Gallic acid (3,4,5-trihydroxybenzoic acid) derivatives have been studied for various biological activities including anticancer (Saxena et al., 2008), antioxidant and antimicrobial activity (Arunkumar et al., 2006). In order to prepare a new derivative of gallic acid, the reaction between 3,4,5-trihydroxybenzoylhydrazine and indole-2-carboxaldehyde was carried out to synthesize the related gallichydrazone; 3,4,5-trihydroxy-N'-[(1H-indol-2-yl)methylidene]benzoylhydrazide. However, a crystal suitable for X-ray diffraction was unexpectedly obtained during the synthesis.

A view of the title structure is illustrated in Fig. 1. The asymmetric unit contains two molecules of the gallic hydrazone with different conformation. In one of them, (I), the aromatic rings are nearly coplanar [dihedral angle = 11.00 (0.16) °], similar to the related previously reported structures (Khaledi et al., 2008a, 2008b, 2009a, 2009b), whereas in the other one, (II), they are highly twisted with respect to each other, the dihedral angle between the two ring planes being 52.43 (0.11) °. The crystal structure is an infinite two-dimensional, hydrogen bonded, network of gallic hydrazone molecules (Fig. 2) with methanol solvate molecules. In addition, π–π interactions between aromatic rings occur. The benzoylhydrazide rings of molecule (I) and the symmetry-related planes at (-x+2, -y, -z+1 and -x+1, -y, -z + 1) are arranged in an antiparallel manner above each other in an infinite one dimensional chain with centroid separations of 3.783 (2) Å and 3.973 (2) Å alternatively. The benzoylhydrazide ring of molecule (II) and the symmetry-related plane at (-x + 2, -y + 1, -z + 1) also interact with one another through π–π stacking, with a centroid-centroid distances of 3.703 (2) Å, leading to a dimer. The framework is interdigitated with solvate azine molecules (Fig. 4) in the ratio of one for every two hydrazone molecules. The azine constituent, which is an unexpected decomposition product of the reaction, is almost planar [maximum deviation 0.21 (1) A°] with a trans configuration about N—N single bond, similar to its indole-3-carbaldehyde analogue (Rizal et al., 2008).

Experimental

A solution of indole-2-carboxaldehyde (0.725 g, 5 mmol) in methanol (20 ml) was added to a solution of 3,4,5-trihydroxybenzoylhydrazine (0.92 g, 5 mmol) in ethanol (60 ml). Furthermore, 1 ml of acetic acid was added and the mixture was refluxed for 4 h. The solution was then cooled and filtered to remove the unreacted hydrazide.The filtrate was set aside at room temperature overnight and crystals of the title compound were collected.

Refinement

C-bound hydrogen atoms were placed at calculated positions (C–H 0.95 Å), and were treated as riding on their parent carbon atoms, with U(H) set to 1.2Ueq(C). The nitrogen- and oxygen-bound H atoms were located in a difference Fourier map, and were refined with distance restraints of N–H 0.88±0.01 and O–H 0.84±0.01 Å.

Figures

Fig. 1.
Perspective view of one crystal chemical unit of the title compound defining the atom labelling scheme and showing 40% probability displacement ellipsoids.
Fig. 2.
Packing view looking down the crystallographic α unit cell edge and showing all the links, between electronegative O and N atoms, which are within the range for normal hydrogen bonds.
Fig. 3.
A view of the intermolecular π–π interactions between gallic hydrazone molecules. H atoms have been omitted for clarity. [Symmetry codes: (i) -x + 2, -y, -z + 1; (ii) -x + 1, -y, -z + 1; (iii) -x + 2, -y + 1, -z + 1.]
Fig. 4.
Packing view looking down the crystallographic b unit cell edge thus emphasizing the two-dimensional extension of the polymeric network and the interdigitation with hydrazine molecules.

Crystal data

2C16H13N3O4·C18H14N4·2CH4OZ = 2
Mr = 973.00F(000) = 1020
Triclinic, P1Dx = 1.393 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4642 (15) ÅCell parameters from 754 reflections
b = 12.791 (2) Åθ = 2.5–20.7°
c = 25.079 (5) ŵ = 0.10 mm1
α = 95.918 (3)°T = 100 K
β = 95.166 (4)°Lath, yellow
γ = 101.451 (4)°0.50 × 0.12 × 0.03 mm
V = 2319.3 (8) Å3

Data collection

Bruker APEXII CCD diffractometer7939 independent reflections
Radiation source: fine-focus sealed tube4029 reflections with I > 2σ(I)
graphiteRint = 0.054
[var phi] and ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→8
Tmin = 0.952, Tmax = 0.997k = −15→13
10985 measured reflectionsl = −29→29

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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H atoms treated by a mixture of independent and constrained refinement
S = 0.98w = 1/[σ2(Fo2) + (0.0463P)2] where P = (Fo2 + 2Fc2)/3
7939 reflections(Δ/σ)max = 0.021
693 parametersΔρmax = 0.30 e Å3
14 restraintsΔρmin = −0.31 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
O100.7343 (4)0.2306 (2)0.60742 (10)0.0276 (7)
O130.7280 (4)0.0510 (2)0.41802 (11)0.0333 (8)
H13O0.749 (6)0.003 (3)0.3953 (14)0.050*
O140.7874 (4)−0.1457 (2)0.42855 (11)0.0280 (7)
H14O0.823 (6)−0.201 (2)0.4370 (17)0.042*
O150.8285 (4)−0.2137 (2)0.52914 (10)0.0259 (7)
H15O0.846 (6)−0.225 (3)0.5616 (6)0.039*
N10.5730 (5)0.2917 (3)0.78752 (12)0.0211 (8)
H1N0.571 (5)0.321 (3)0.7570 (8)0.025*
N20.6671 (5)0.1652 (2)0.70038 (13)0.0242 (8)
N30.6927 (5)0.0943 (3)0.65781 (13)0.0260 (8)
H3N0.668 (5)0.0250 (10)0.6599 (15)0.031*
C10.6341 (5)0.1973 (3)0.79275 (15)0.0203 (9)
C20.6431 (5)0.1802 (3)0.84590 (15)0.0263 (10)
H20.68150.12150.86040.032*
C30.5848 (5)0.2656 (3)0.87524 (15)0.0232 (10)
C40.5625 (6)0.2922 (3)0.92965 (16)0.0290 (11)
H40.59370.24860.95600.035*
C50.4951 (6)0.3823 (3)0.94423 (16)0.0317 (11)
H50.47910.40070.98090.038*
C60.4495 (6)0.4473 (3)0.90547 (17)0.0325 (11)
H60.40250.50880.91670.039*
C70.4705 (5)0.4250 (3)0.85215 (16)0.0263 (10)
H70.43860.46960.82630.032*
C80.5402 (5)0.3347 (3)0.83727 (15)0.0222 (10)
C90.6730 (5)0.1316 (3)0.74681 (16)0.0258 (10)
H90.70280.06390.75090.031*
C100.7225 (6)0.1329 (3)0.61037 (16)0.0235 (10)
C110.7412 (5)0.0573 (3)0.56412 (15)0.0199 (9)
C120.7246 (5)0.0893 (3)0.51285 (15)0.0219 (10)
H120.70200.15850.50830.026*
C130.7412 (5)0.0194 (3)0.46881 (15)0.0207 (9)
C140.7731 (5)−0.0820 (3)0.47460 (15)0.0203 (9)
C150.7928 (5)−0.1131 (3)0.52580 (15)0.0191 (9)
C160.7771 (5)−0.0445 (3)0.57041 (15)0.0223 (10)
H160.7907−0.06610.60540.027*
O260.8842 (4)0.7516 (2)0.62971 (10)0.0246 (7)
O291.3673 (4)0.6412 (2)0.51863 (11)0.0276 (7)
H29O1.430 (5)0.601 (3)0.5035 (15)0.041*
O301.3089 (4)0.4224 (2)0.51396 (10)0.0225 (7)
H30O1.254 (5)0.3578 (13)0.5053 (15)0.034*
O311.0303 (4)0.3140 (2)0.56466 (11)0.0279 (7)
H31O0.938 (4)0.293 (3)0.5802 (15)0.042*
N40.5999 (5)0.7939 (3)0.79555 (12)0.0230 (8)
H4N0.609 (5)0.820 (3)0.7648 (8)0.028*
N50.7553 (5)0.6765 (2)0.71588 (12)0.0243 (8)
N60.8261 (5)0.6142 (3)0.67896 (13)0.0240 (8)
H6N0.818 (5)0.5464 (12)0.6837 (15)0.029*
C170.6739 (5)0.7044 (3)0.80452 (15)0.0233 (10)
C180.6735 (5)0.6888 (3)0.85733 (15)0.0241 (10)
H180.71630.63310.87360.029*
C190.5975 (5)0.7705 (3)0.88380 (15)0.0232 (10)
C200.5626 (6)0.7976 (3)0.93695 (16)0.0284 (11)
H200.59550.75760.96480.034*
C210.4798 (6)0.8830 (3)0.94795 (16)0.0312 (11)
H210.45620.90240.98380.037*
C220.4298 (6)0.9418 (3)0.90718 (17)0.0315 (11)
H220.37100.99960.91600.038*
C230.4630 (5)0.9184 (3)0.85492 (16)0.0250 (10)
H230.42640.95830.82740.030*
C240.5516 (5)0.8349 (3)0.84352 (15)0.0209 (9)
C250.7390 (5)0.6424 (3)0.76214 (15)0.0233 (10)
H250.77010.57580.76830.028*
C260.8945 (5)0.6580 (3)0.63666 (15)0.0209 (9)
C270.9906 (5)0.5921 (3)0.60161 (14)0.0201 (9)
C281.1271 (5)0.6445 (3)0.57419 (14)0.0198 (9)
H281.14940.72060.57560.024*
C291.2315 (5)0.5871 (3)0.54470 (15)0.0209 (9)
C301.1997 (5)0.4760 (3)0.54255 (14)0.0183 (9)
C311.0592 (5)0.4240 (3)0.56948 (14)0.0185 (9)
C320.9561 (5)0.4800 (3)0.59929 (14)0.0188 (9)
H320.86270.44340.61810.023*
N7−0.1199 (5)0.3424 (3)1.11800 (14)0.0329 (9)
H7N−0.160 (5)0.2730 (11)1.1082 (15)0.039*
N8−0.0309 (5)0.2620 (3)1.01631 (15)0.0412 (10)
N90.0213 (5)0.2391 (3)0.96486 (15)0.0413 (10)
N100.0984 (5)0.1700 (3)0.86232 (16)0.0390 (10)
H10N0.140 (6)0.2386 (12)0.8734 (17)0.047*
C33−0.0304 (6)0.4065 (4)1.08362 (17)0.0338 (11)
C340.0234 (6)0.5092 (4)1.10970 (17)0.0338 (11)
H340.08830.56941.09520.041*
C35−0.0343 (6)0.5100 (4)1.16199 (17)0.0318 (11)
C36−0.0175 (6)0.5877 (4)1.20641 (18)0.0365 (12)
H360.04270.65981.20470.044*
C37−0.0892 (6)0.5589 (4)1.25316 (18)0.0364 (12)
H37−0.07830.61161.28350.044*
C38−0.1782 (6)0.4520 (4)1.25592 (18)0.0355 (12)
H38−0.22670.43371.28830.043*
C39−0.1965 (6)0.3734 (4)1.21283 (17)0.0342 (11)
H39−0.25650.30141.21510.041*
C40−0.1247 (6)0.4023 (3)1.16585 (17)0.0299 (11)
C410.0086 (6)0.3637 (4)1.03193 (17)0.0351 (12)
H410.06480.41131.00870.042*
C42−0.0074 (6)0.1373 (4)0.94922 (19)0.0404 (12)
H42−0.05280.08740.97290.048*
C430.0283 (6)0.0996 (4)0.8971 (2)0.0404 (12)
C44−0.0064 (6)−0.0023 (4)0.8699 (2)0.0450 (13)
H44−0.0547−0.06670.88420.054*
C450.0423 (6)0.0051 (4)0.8166 (2)0.0388 (12)
C460.0367 (6)−0.0702 (4)0.7703 (2)0.0505 (15)
H46−0.0038−0.14500.77160.061*
C470.0905 (7)−0.0332 (5)0.7238 (2)0.0575 (16)
H470.0874−0.08310.69270.069*
C480.1500 (6)0.0768 (4)0.7210 (2)0.0519 (15)
H480.18420.10020.68790.062*
C490.1598 (6)0.1511 (4)0.76502 (19)0.0454 (13)
H490.20180.22560.76310.055*
C500.1067 (6)0.1146 (4)0.81268 (19)0.0379 (12)
O510.3727 (4)0.6124 (2)0.31454 (11)0.0291 (7)
H51O0.348 (6)0.6718 (18)0.3249 (16)0.044*
C510.5272 (6)0.6038 (4)0.35040 (18)0.0448 (13)
H51A0.63260.66070.34640.067*
H51B0.55800.53350.34180.067*
H51C0.49710.61140.38760.067*
O520.3718 (4)0.1291 (2)0.31264 (11)0.0270 (7)
H52O0.303 (5)0.173 (3)0.3177 (17)0.040*
C520.5328 (6)0.1969 (3)0.34338 (17)0.0348 (11)
H52A0.55200.26850.33150.052*
H52B0.64040.16560.33780.052*
H52C0.51570.20280.38180.052*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O100.0363 (18)0.0170 (17)0.0324 (17)0.0056 (13)0.0150 (14)0.0060 (13)
O130.052 (2)0.034 (2)0.0181 (17)0.0156 (16)0.0047 (15)0.0088 (13)
O140.0370 (19)0.0241 (18)0.0239 (16)0.0105 (14)0.0041 (14)−0.0008 (13)
O150.0401 (19)0.0190 (16)0.0207 (16)0.0095 (14)0.0071 (15)0.0033 (13)
N10.025 (2)0.023 (2)0.0172 (19)0.0072 (16)0.0037 (16)0.0043 (15)
N20.034 (2)0.0181 (19)0.021 (2)0.0060 (16)0.0088 (16)0.0013 (15)
N30.036 (2)0.0176 (19)0.024 (2)0.0029 (17)0.0120 (17)−0.0006 (16)
C10.019 (2)0.019 (2)0.025 (2)0.0060 (18)0.0048 (18)0.0023 (18)
C20.029 (3)0.024 (3)0.024 (2)0.003 (2)0.001 (2)0.0049 (19)
C30.028 (3)0.019 (2)0.021 (2)0.0014 (19)0.0034 (19)0.0030 (18)
C40.036 (3)0.031 (3)0.018 (2)0.004 (2)0.003 (2)0.0018 (19)
C50.041 (3)0.033 (3)0.019 (2)0.004 (2)0.005 (2)−0.003 (2)
C60.032 (3)0.033 (3)0.031 (3)0.004 (2)0.008 (2)−0.005 (2)
C70.025 (3)0.025 (3)0.029 (3)0.007 (2)0.003 (2)0.0004 (19)
C80.022 (2)0.024 (2)0.019 (2)0.0013 (19)0.0024 (18)0.0006 (18)
C90.026 (3)0.024 (3)0.026 (2)0.0009 (19)0.004 (2)0.0033 (19)
C100.025 (2)0.017 (2)0.027 (2)−0.0002 (19)0.0068 (19)0.0010 (18)
C110.019 (2)0.018 (2)0.023 (2)0.0029 (18)0.0064 (18)0.0027 (18)
C120.026 (2)0.015 (2)0.025 (2)0.0039 (18)0.0035 (19)0.0062 (18)
C130.021 (2)0.025 (2)0.017 (2)0.0053 (19)0.0022 (18)0.0061 (18)
C140.020 (2)0.022 (2)0.016 (2)0.0013 (18)0.0054 (18)−0.0020 (18)
C150.021 (2)0.012 (2)0.025 (2)0.0049 (17)0.0039 (18)0.0047 (17)
C160.026 (2)0.019 (2)0.022 (2)0.0021 (19)0.0061 (19)0.0043 (18)
O260.0384 (18)0.0154 (16)0.0228 (15)0.0097 (13)0.0091 (13)0.0030 (12)
O290.0279 (18)0.0197 (17)0.0383 (18)0.0050 (13)0.0181 (14)0.0051 (13)
O300.0223 (17)0.0174 (16)0.0282 (16)0.0030 (13)0.0085 (13)0.0017 (13)
O310.0291 (18)0.0205 (17)0.0366 (18)0.0061 (14)0.0190 (14)0.0000 (13)
N40.026 (2)0.025 (2)0.019 (2)0.0074 (16)0.0045 (17)0.0001 (16)
N50.032 (2)0.025 (2)0.0176 (19)0.0059 (16)0.0091 (16)0.0011 (15)
N60.035 (2)0.019 (2)0.0201 (19)0.0070 (17)0.0120 (16)0.0019 (16)
C170.021 (2)0.026 (3)0.024 (2)0.0051 (19)0.0069 (19)0.0025 (19)
C180.028 (3)0.027 (2)0.021 (2)0.011 (2)0.0047 (19)0.0057 (18)
C190.026 (2)0.022 (2)0.022 (2)0.0047 (19)0.0036 (19)0.0035 (18)
C200.034 (3)0.029 (3)0.021 (2)0.004 (2)0.004 (2)0.0020 (19)
C210.041 (3)0.031 (3)0.020 (2)0.005 (2)0.010 (2)−0.004 (2)
C220.032 (3)0.027 (3)0.038 (3)0.011 (2)0.010 (2)0.001 (2)
C230.030 (3)0.020 (2)0.028 (2)0.010 (2)0.008 (2)0.0051 (19)
C240.021 (2)0.022 (2)0.017 (2)0.0028 (19)0.0016 (18)−0.0025 (18)
C250.024 (2)0.023 (2)0.025 (2)0.0063 (19)0.0065 (19)0.0055 (19)
C260.022 (2)0.018 (2)0.021 (2)0.0015 (18)0.0012 (18)0.0011 (18)
C270.020 (2)0.025 (2)0.014 (2)0.0049 (19)0.0011 (17)−0.0009 (17)
C280.030 (2)0.010 (2)0.020 (2)0.0056 (18)0.0037 (19)0.0026 (17)
C290.019 (2)0.019 (2)0.024 (2)0.0018 (18)0.0028 (19)0.0010 (18)
C300.014 (2)0.022 (2)0.018 (2)0.0046 (18)0.0054 (17)−0.0017 (17)
C310.021 (2)0.012 (2)0.021 (2)0.0011 (18)0.0031 (18)0.0022 (17)
C320.022 (2)0.018 (2)0.017 (2)0.0022 (18)0.0083 (18)0.0044 (17)
N70.030 (2)0.029 (2)0.037 (2)−0.0003 (19)0.0046 (18)0.0002 (19)
N80.036 (2)0.050 (3)0.035 (2)0.005 (2)0.0053 (19)−0.001 (2)
N90.033 (2)0.052 (3)0.039 (2)0.009 (2)0.0062 (19)0.003 (2)
N100.029 (2)0.037 (3)0.047 (3)0.003 (2)0.0061 (19)−0.011 (2)
C330.023 (3)0.046 (3)0.032 (3)0.005 (2)0.003 (2)0.006 (2)
C340.026 (3)0.035 (3)0.042 (3)0.006 (2)−0.001 (2)0.011 (2)
C350.021 (3)0.038 (3)0.037 (3)0.008 (2)−0.002 (2)0.010 (2)
C360.030 (3)0.028 (3)0.048 (3)0.000 (2)−0.004 (2)0.004 (2)
C370.033 (3)0.039 (3)0.035 (3)0.008 (2)−0.003 (2)−0.001 (2)
C380.023 (3)0.044 (3)0.037 (3)0.002 (2)0.000 (2)0.009 (2)
C390.024 (3)0.032 (3)0.042 (3)−0.001 (2)−0.003 (2)0.005 (2)
C400.019 (2)0.034 (3)0.034 (3)0.003 (2)−0.002 (2)0.001 (2)
C410.019 (3)0.054 (3)0.034 (3)0.010 (2)0.003 (2)0.009 (2)
C420.030 (3)0.047 (3)0.045 (3)0.009 (2)−0.001 (2)0.010 (3)
C430.031 (3)0.038 (3)0.052 (3)0.008 (2)0.004 (3)0.003 (3)
C440.029 (3)0.031 (3)0.072 (4)0.006 (2)0.000 (3)0.003 (3)
C450.022 (3)0.035 (3)0.056 (3)0.007 (2)−0.002 (2)−0.006 (2)
C460.030 (3)0.039 (3)0.075 (4)0.008 (2)−0.008 (3)−0.019 (3)
C470.037 (3)0.063 (4)0.064 (4)0.009 (3)0.007 (3)−0.032 (3)
C480.038 (3)0.053 (4)0.057 (4)−0.002 (3)0.018 (3)−0.020 (3)
C490.033 (3)0.047 (3)0.050 (3)0.001 (2)0.009 (3)−0.012 (3)
C500.022 (3)0.035 (3)0.051 (3)0.005 (2)0.003 (2)−0.016 (2)
O510.0360 (19)0.0255 (18)0.0272 (17)0.0103 (15)0.0070 (14)−0.0004 (13)
C510.040 (3)0.053 (3)0.042 (3)0.013 (3)−0.004 (2)0.005 (2)
O520.0322 (19)0.0208 (18)0.0285 (17)0.0073 (13)0.0044 (14)0.0019 (13)
C520.027 (3)0.040 (3)0.034 (3)0.002 (2)−0.003 (2)0.007 (2)

Geometric parameters (Å, °)

O10—C101.246 (4)C22—H220.9500
O13—C131.376 (4)C23—C241.383 (5)
O13—H13O0.844 (10)C23—H230.9500
O14—C141.368 (4)C25—H250.9500
O14—H14O0.843 (10)C26—C271.482 (5)
O15—C151.374 (4)C27—C281.382 (5)
O15—H15O0.845 (10)C27—C321.400 (5)
N1—C81.373 (5)C28—C291.383 (5)
N1—C11.387 (5)C28—H280.9500
N1—H1N0.884 (10)C29—C301.388 (5)
N2—C91.282 (5)C30—C311.393 (5)
N2—N31.380 (4)C31—C321.370 (5)
N3—C101.354 (5)C32—H320.9500
N3—H3N0.877 (10)N7—C401.363 (5)
C1—C21.371 (5)N7—C331.376 (5)
C1—C91.440 (5)N7—H7N0.879 (10)
C2—C31.415 (5)N8—C411.286 (5)
C2—H20.9500N8—N91.400 (5)
C3—C41.405 (5)N9—C421.290 (5)
C3—C81.426 (5)N10—C431.378 (6)
C4—C51.375 (5)N10—C501.380 (5)
C4—H40.9500N10—H10N0.877 (10)
C5—C61.404 (6)C33—C341.371 (6)
C5—H50.9500C33—C411.432 (6)
C6—C71.368 (5)C34—C351.416 (6)
C6—H60.9500C34—H340.9500
C7—C81.389 (5)C35—C361.394 (6)
C7—H70.9500C35—C401.425 (6)
C9—H90.9500C36—C371.386 (6)
C10—C111.467 (5)C36—H360.9500
C11—C121.392 (5)C37—C381.409 (6)
C11—C161.401 (5)C37—H370.9500
C12—C131.378 (5)C38—C391.375 (6)
C12—H120.9500C38—H380.9500
C13—C141.384 (5)C39—C401.392 (6)
C14—C151.387 (5)C39—H390.9500
C15—C161.377 (5)C41—H410.9500
C16—H160.9500C42—C431.414 (6)
O26—C261.243 (4)C42—H420.9500
O29—C291.367 (4)C43—C441.371 (6)
O29—H29O0.845 (10)C44—C451.425 (6)
O30—C301.369 (4)C44—H440.9500
O30—H30O0.841 (10)C45—C501.405 (6)
O31—C311.372 (4)C45—C461.423 (6)
O31—H31O0.836 (10)C46—C471.367 (7)
N4—C241.370 (5)C46—H460.9500
N4—C171.396 (5)C47—C481.399 (7)
N4—H4N0.876 (10)C47—H470.9500
N5—C251.289 (5)C48—C491.367 (6)
N5—N61.369 (4)C48—H480.9500
N6—C261.344 (5)C49—C501.389 (6)
N6—H6N0.877 (10)C49—H490.9500
C17—C181.360 (5)O51—C511.427 (5)
C17—C251.438 (5)O51—H51O0.839 (10)
C18—C191.419 (5)C51—H51A0.9800
C18—H180.9500C51—H51B0.9800
C19—C201.403 (5)C51—H51C0.9800
C19—C241.428 (5)O52—C521.440 (5)
C20—C211.374 (5)O52—H52O0.837 (10)
C20—H200.9500C52—H52A0.9800
C21—C221.397 (6)C52—H52B0.9800
C21—H210.9500C52—H52C0.9800
C22—C231.369 (5)
C13—O13—H13O110 (3)O26—C26—C27122.7 (4)
C14—O14—H14O109 (3)N6—C26—C27116.9 (4)
C15—O15—H15O111 (3)C28—C27—C32120.0 (3)
C8—N1—C1109.0 (3)C28—C27—C26118.3 (4)
C8—N1—H1N128 (2)C32—C27—C26121.5 (3)
C1—N1—H1N123 (2)C27—C28—C29120.5 (4)
C9—N2—N3116.0 (3)C27—C28—H28119.7
C10—N3—N2117.8 (3)C29—C28—H28119.7
C10—N3—H3N121 (3)O29—C29—C28119.2 (3)
N2—N3—H3N120 (3)O29—C29—C30120.8 (3)
C2—C1—N1109.0 (3)C28—C29—C30120.0 (4)
C2—C1—C9129.2 (4)O30—C30—C29118.2 (3)
N1—C1—C9121.8 (4)O30—C30—C31122.9 (3)
C1—C2—C3107.8 (4)C29—C30—C31118.9 (3)
C1—C2—H2126.1C32—C31—O31121.9 (3)
C3—C2—H2126.1C32—C31—C30121.7 (4)
C4—C3—C2134.7 (4)O31—C31—C30116.4 (3)
C4—C3—C8118.5 (4)C31—C32—C27118.9 (3)
C2—C3—C8106.8 (3)C31—C32—H32120.5
C5—C4—C3119.1 (4)C27—C32—H32120.5
C5—C4—H4120.4C40—N7—C33109.8 (4)
C3—C4—H4120.4C40—N7—H7N130 (3)
C4—C5—C6120.7 (4)C33—N7—H7N120 (3)
C4—C5—H5119.6C41—N8—N9111.2 (4)
C6—C5—H5119.6C42—N9—N8112.7 (4)
C7—C6—C5122.2 (4)C43—N10—C50110.2 (4)
C7—C6—H6118.9C43—N10—H10N121 (3)
C5—C6—H6118.9C50—N10—H10N128 (3)
C6—C7—C8117.3 (4)C34—C33—N7108.4 (4)
C6—C7—H7121.3C34—C33—C41129.2 (4)
C8—C7—H7121.3N7—C33—C41122.2 (4)
N1—C8—C7130.5 (4)C33—C34—C35108.3 (4)
N1—C8—C3107.4 (3)C33—C34—H34125.9
C7—C8—C3122.1 (4)C35—C34—H34125.9
N2—C9—C1119.6 (4)C36—C35—C34135.0 (4)
N2—C9—H9120.2C36—C35—C40119.0 (4)
C1—C9—H9120.2C34—C35—C40106.0 (4)
O10—C10—N3119.5 (3)C37—C36—C35119.5 (4)
O10—C10—C11122.3 (4)C37—C36—H36120.3
N3—C10—C11118.2 (4)C35—C36—H36120.3
C12—C11—C16119.8 (3)C36—C37—C38120.4 (4)
C12—C11—C10118.2 (4)C36—C37—H37119.8
C16—C11—C10121.9 (4)C38—C37—H37119.8
C13—C12—C11119.2 (4)C39—C38—C37121.5 (4)
C13—C12—H12120.4C39—C38—H38119.3
C11—C12—H12120.4C37—C38—H38119.3
O13—C13—C12119.7 (3)C38—C39—C40118.1 (4)
O13—C13—C14119.0 (3)C38—C39—H39120.9
C12—C13—C14121.3 (4)C40—C39—H39120.9
O14—C14—C13117.1 (3)N7—C40—C39131.0 (4)
O14—C14—C15123.5 (4)N7—C40—C35107.5 (4)
C13—C14—C15119.4 (3)C39—C40—C35121.5 (4)
O15—C15—C16122.9 (4)N8—C41—C33121.3 (4)
O15—C15—C14116.8 (3)N8—C41—H41119.3
C16—C15—C14120.3 (4)C33—C41—H41119.3
C15—C16—C11119.9 (4)N9—C42—C43120.3 (5)
C15—C16—H16120.0N9—C42—H42119.8
C11—C16—H16120.0C43—C42—H42119.8
C29—O29—H29O113 (3)C44—C43—N10107.8 (4)
C30—O30—H30O109 (3)C44—C43—C42130.9 (5)
C31—O31—H31O107 (3)N10—C43—C42121.2 (4)
C24—N4—C17108.0 (3)C43—C44—C45108.2 (4)
C24—N4—H4N131 (3)C43—C44—H44125.9
C17—N4—H4N120 (3)C45—C44—H44125.9
C25—N5—N6116.1 (3)C50—C45—C46118.1 (5)
C26—N6—N5118.8 (3)C50—C45—C44107.0 (4)
C26—N6—H6N124 (3)C46—C45—C44134.9 (5)
N5—N6—H6N117 (3)C47—C46—C45119.0 (5)
C18—C17—N4109.7 (3)C47—C46—H46120.5
C18—C17—C25128.0 (4)C45—C46—H46120.5
N4—C17—C25122.2 (4)C46—C47—C48121.2 (5)
C17—C18—C19107.8 (4)C46—C47—H47119.4
C17—C18—H18126.1C48—C47—H47119.4
C19—C18—H18126.1C49—C48—C47121.3 (5)
C20—C19—C18134.9 (4)C49—C48—H48119.4
C20—C19—C24118.8 (4)C47—C48—H48119.4
C18—C19—C24106.3 (3)C48—C49—C50118.1 (5)
C21—C20—C19118.8 (4)C48—C49—H49121.0
C21—C20—H20120.6C50—C49—H49121.0
C19—C20—H20120.6N10—C50—C49130.9 (4)
C20—C21—C22121.0 (4)N10—C50—C45106.9 (4)
C20—C21—H21119.5C49—C50—C45122.2 (4)
C22—C21—H21119.5C51—O51—H51O106 (3)
C23—C22—C21122.0 (4)O51—C51—H51A109.5
C23—C22—H22119.0O51—C51—H51B109.5
C21—C22—H22119.0H51A—C51—H51B109.5
C22—C23—C24117.7 (4)O51—C51—H51C109.5
C22—C23—H23121.2H51A—C51—H51C109.5
C24—C23—H23121.2H51B—C51—H51C109.5
N4—C24—C23130.2 (4)C52—O52—H52O95 (3)
N4—C24—C19108.1 (3)O52—C52—H52A109.5
C23—C24—C19121.6 (4)O52—C52—H52B109.5
N5—C25—C17120.5 (4)H52A—C52—H52B109.5
N5—C25—H25119.8O52—C52—H52C109.5
C17—C25—H25119.8H52A—C52—H52C109.5
O26—C26—N6120.4 (3)H52B—C52—H52C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O13—H13O···O140.84 (1)2.21 (4)2.674 (4)115 (4)
O14—H14O···O31i0.84 (1)1.98 (2)2.778 (4)158 (4)
O14—H14O···O150.84 (1)2.33 (4)2.763 (4)112 (3)
O15—H15O···O26ii0.85 (1)1.77 (1)2.617 (4)179 (4)
N1—H1N···O51iii0.88 (1)2.11 (1)2.976 (4)167 (3)
N3—H3N···O52iv0.88 (1)2.13 (2)2.983 (4)165 (4)
O29—H29O···O30v0.85 (1)2.11 (2)2.858 (4)148 (4)
O30—H30O···O15i0.84 (1)1.91 (2)2.732 (4)165 (4)
O31—H31O···O100.84 (1)1.80 (1)2.626 (4)172 (4)
N4—H4N···O52iii0.88 (1)2.12 (1)2.992 (4)175 (3)
N6—H6N···O51iii0.88 (1)2.24 (2)3.011 (4)146 (3)
O51—H51O···O10iii0.84 (1)2.21 (3)2.934 (4)145 (4)
O51—H51O···N2iii0.84 (1)2.26 (3)2.975 (4)143 (4)
O52—H52O···N5iii0.84 (1)2.29 (3)2.963 (4)138 (4)
O52—H52O···O26iii0.84 (1)2.29 (2)3.046 (4)150 (4)

Symmetry codes: (i) −x+2, −y, −z+1; (ii) x, y−1, z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) −x+3, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2302).

References

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