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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 71| Part 12| December 2015| Pages o947-o948
https://doi.org/10.1107/S2056989015021325

Crystal structure of 4-[(E)-(4-hy­dr­oxy­benzyl­­idene)amino]-1,5-di­methyl-2-phenyl-1H-pyrazol-3(2H)-one

Joel T. Mague,a Mehmet Akkurt,b Shaaban K. Mohamed,c,d Alaa F. Mohamede and Mustafa R. Albayatif*

aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, dChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, eNational Organization for Drug Control and Research, Giza, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 9 November 2015; accepted 10 November 2015; online 14 November 2015)

The asymmetric unit of the title compound, C18H17N3O2, comprises three independent mol­ecules (1, 2 and 3). In mol­ecule 1, the dihedral angles between the pyrazolone ring and the pendant phenyl and hydroxybenzene rings are 54.43 (6) and 28.72 (6)°, respectively. The corresponding data for mol­ecule 2 are 86.84 (6) and 25.69 (5)°, respectively, and for mol­ecule 3 are 47.41 (7) and 17.09 (7)°, respectively. The three mol­ecules feature an intra­molecular C—H⋯O inter­action, which closes an S(6) ring in each case. In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds, which generate [100] chains incorporating all three asymmetric mol­ecules. Two weak C—H⋯O interactions connect three independent molecules to each other along the c-axis direction.

CCDC reference: 1436039

Similar articles

1. Related literature

For the biological activities of the pyrazolone ring system, see: Nirali & Maulik (2010[Nirali, S. & Maulik, K. (2010). Int. J. Drug Dev. Res. 2, 975-978.]); Rahat et al. (2008[Rahat, K., Imam, U., Sultan, A. & Mohammad, M. (2008). Bangladesh J. Pharmacol. 3, 27-35.]); Thakkar & Joshi (2010[Thakkar, A. & Joshi, K. (2010). Eur. J. Chem. 7, 1396-1406.]); Mahmoud et al. (2011[Mahmoud, M., Ramiz, M. & Ibrahim, S. (2011). J. Chin. Chem. Soc. 58, 6-11.]); Tripathy et al. (2007[Tripathy, R., Ghose, A., Singh, J., Bacon, E., Angeles, T., Yang, S., Albom, M., Aimone, L., Herman, J. & Mallamo, J. (2007). Bioorg. Med. Chem. Lett. 17, 1793-1798.]); Brune (1997[Brune, K. (1997). Acute Pain, 1, 33-40.]); Abdel-Aziz et al. (2009[Abdel-Aziz, M., Abuo-Rahma, G. El-Din A. & Hassan, A. A. (2009). Eur. J. Med. Chem. 44, 3480-3487.]). For industrial applications, see: Karci & Ertan (2002[Karci, F. & Ertan, N. (2002). Dyes Pigm. 55, 99-108.]); Khalil et al. (2005[Khalil, A., Hassan, M., Mohamed, M. & El-Sayed, A. (2005). Dyes Pigm. 66, 241-245.]); Ho (2005[Ho, Y. W. (2005). Dyes Pigm. 64, 223-230.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C18H17N3O2

  • Mr = 307.35

  • Triclinic, [P \overline 1]

  • a = 8.1214 (7) Å

  • b = 12.5405 (10) Å

  • c = 23.1875 (19) Å

  • α = 91.121 (1)°

  • β = 90.199 (1)°

  • γ = 90.748 (1)°

  • V = 2360.9 (3) Å3

  • Z = 6

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 150 K

  • 0.30 × 0.18 × 0.15 mm

2.2. Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2015[Bruker (2015). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.86, Tmax = 0.99

  • 22491 measured reflections

  • 11415 independent reflections

  • 7110 reflections with I > 2σ(I)

  • Rint = 0.035

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.115

  • S = 0.97

  • 11415 reflections

  • 628 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯O4 0.84 1.86 2.6947 (14) 170
O3—H3A⋯O6i 0.84 1.86 2.6993 (15) 175
O5—H5A⋯O4 0.84 1.88 2.7218 (15) 179
C7—H7⋯O2 0.95 2.30 3.009 (2) 131
C25—H25⋯O4 0.95 2.46 3.0612 (18) 121
C43—H43⋯O6 0.95 2.36 2.9989 (18) 124
C33—H33⋯O6ii 0.95 2.42 3.168 (2) 135
C35—H35⋯O2ii 0.95 2.31 3.122 (2) 143
Symmetry codes: (i) x-1, y, z; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2015[Bruker (2015). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2015[Bruker (2015). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information

CCDC reference: 1436039

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015021325/hb7540sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015021325/hb7540Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015021325/hb7540Isup3.cml

checkCIF report


Comment top

The pyrazolone ring system is an important structural moiety found in numerous pharmaceutically active compounds. This is mainly due to the ease preparation and the important versatile pharmaceutical and industrial applications. Pyrazolones are mostly useful as anti-inflammatory and analgesic activities (Nirali & Maulik, 2010), but in recent times, they are known to exhibit anti-cancer (Rahat et al., 2008), anti-bacterial (Thakkar & Joshi, 2010) and several other pharmacological actions like anti-fungal (Mahmoud et al., 2011), protein kinase inhibitor (Tripathy et al., 2007), anti-pyretic (Brune, 1997), anti-convulsant (Abdel-Aziz et al., 2009). In addition, they have been used as plant growth regulator, herbicidal and as an azo-dyes (Karci & Ertan, 2002; Khalil et al., 2005; Ho, 2005). Based on such findings and following to our on-going study, we report herein the synthesis and crystal structure of the title compound.

For the title compound there are three independent molecules in the asymmetric unit (Fig. 1) which differ in their conformations. In molecules 1 - 3, respectively, the maximum deviations from the mean planes of the pyrazolone rings are 0.0501 (8) Å (N3), 0.0305 (8) Å (N5) and -0.0367 (8) Å (N8). In molecule 1 the dihedral angles between the mean plane of the pyrazolone ring and those of the phenyl and hydroxyphenyl substituents are, respectively, 54.43 (6)° and 28.72 (6)°. In molecule 2 the corresponding angles are 86.84 (6) and 25.69 (5)° while in molecule 3 they are 47.41 (7) and 17.09 (7)°. In the asymmetric unit, molecules 1 and 3,respectively, form O1—H1···O4 and O5—H5A···O4 hydrogen bonds which tie the unit together (Fig. 1 and Table 1) while O3—H3A···O6i (i: x - 1, y, z) hydrogen bonds aid in the packing (Fig. 2 and Table 1).

Related literature top

For the biological activities of the pyrazolone ring system, see: Nirali & Maulik (2010); Rahat et al. (2008); Thakkar & Joshi (2010); Mahmoud et al. (2011); Tripathy et al. (2007); Brune (1997); Abdel-Aziz et al. (2009). For industrial applications, see: Karci & Ertan (2002); Khalil et al. (2005); Ho (2005).

Refinement top

H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å) while those attached to oxygen were placed in ocations derived from a difference map and their coordinates adjusted to give O—H = 0.84 Å. All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

Structure description top

The pyrazolone ring system is an important structural moiety found in numerous pharmaceutically active compounds. This is mainly due to the ease preparation and the important versatile pharmaceutical and industrial applications. Pyrazolones are mostly useful as anti-inflammatory and analgesic activities (Nirali & Maulik, 2010), but in recent times, they are known to exhibit anti-cancer (Rahat et al., 2008), anti-bacterial (Thakkar & Joshi, 2010) and several other pharmacological actions like anti-fungal (Mahmoud et al., 2011), protein kinase inhibitor (Tripathy et al., 2007), anti-pyretic (Brune, 1997), anti-convulsant (Abdel-Aziz et al., 2009). In addition, they have been used as plant growth regulator, herbicidal and as an azo-dyes (Karci & Ertan, 2002; Khalil et al., 2005; Ho, 2005). Based on such findings and following to our on-going study, we report herein the synthesis and crystal structure of the title compound.

For the title compound there are three independent molecules in the asymmetric unit (Fig. 1) which differ in their conformations. In molecules 1 - 3, respectively, the maximum deviations from the mean planes of the pyrazolone rings are 0.0501 (8) Å (N3), 0.0305 (8) Å (N5) and -0.0367 (8) Å (N8). In molecule 1 the dihedral angles between the mean plane of the pyrazolone ring and those of the phenyl and hydroxyphenyl substituents are, respectively, 54.43 (6)° and 28.72 (6)°. In molecule 2 the corresponding angles are 86.84 (6) and 25.69 (5)° while in molecule 3 they are 47.41 (7) and 17.09 (7)°. In the asymmetric unit, molecules 1 and 3,respectively, form O1—H1···O4 and O5—H5A···O4 hydrogen bonds which tie the unit together (Fig. 1 and Table 1) while O3—H3A···O6i (i: x - 1, y, z) hydrogen bonds aid in the packing (Fig. 2 and Table 1).

For the biological activities of the pyrazolone ring system, see: Nirali & Maulik (2010); Rahat et al. (2008); Thakkar & Joshi (2010); Mahmoud et al. (2011); Tripathy et al. (2007); Brune (1997); Abdel-Aziz et al. (2009). For industrial applications, see: Karci & Ertan (2002); Khalil et al. (2005); Ho (2005).

Computing details top

Data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015b); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015a); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit with labeling scheme and 50% probability ellipsoids. The O—H···O hydrogen bonds are shown as dotted lines.
[Figure 2] Fig. 2. The unit-cell contents viewed down the a axis. Intermolecular O—H···O and C—H···O hydrogen bonds are shown, respectively, as red and black dotted lines.
4-[(E)-(4-Hydroxybenzylidene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one top
Crystal data top
C18H17N3O2Z = 6
Mr = 307.35F(000) = 972
Triclinic, P1Dx = 1.297 Mg m−3
a = 8.1214 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.5405 (10) ÅCell parameters from 6224 reflections
c = 23.1875 (19) Åθ = 2.4–28.2°
α = 91.121 (1)°µ = 0.09 mm−1
β = 90.199 (1)°T = 150 K
γ = 90.748 (1)°Column, colourless
V = 2360.9 (3) Å30.30 × 0.18 × 0.15 mm
Data collection top
Bruker SMART APEX CCD
diffractometer		11415 independent reflections
Radiation source: fine-focus sealed tube7110 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
Detector resolution: 8.3333 pixels mm-1θmax = 28.5°, θmin = 1.6°
φ and ω scansh = −10→10
Absorption correction: multi-scan
(SADABS; Bruker, 2015)		k = −16→16
Tmin = 0.86, Tmax = 0.99l = −30→31
22491 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: mixed
wR(F2) = 0.115H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0468P)2]
where P = (Fo2 + 2Fc2)/3
11415 reflections(Δ/σ)max = 0.001
628 parametersΔρmax = 0.25 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C18H17N3O2γ = 90.748 (1)°
Mr = 307.35V = 2360.9 (3) Å3
Triclinic, P1Z = 6
a = 8.1214 (7) ÅMo Kα radiation
b = 12.5405 (10) ŵ = 0.09 mm−1
c = 23.1875 (19) ÅT = 150 K
α = 91.121 (1)°0.30 × 0.18 × 0.15 mm
β = 90.199 (1)°
Data collection top
Bruker SMART APEX CCD
diffractometer		11415 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2015)		7110 reflections with I > 2σ(I)
Tmin = 0.86, Tmax = 0.99Rint = 0.035
22491 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.115H-atom parameters constrained
S = 0.97Δρmax = 0.25 e Å−3
11415 reflectionsΔρmin = −0.21 e Å−3
628 parameters
Special details top

Experimental. The diffraction data were collected in three sets of 363 frames (0.5° width in ω) at φ = 0, 120 and 240°. A scan time of 40 sec/frame was used.

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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å) while those attached to oxygen were placed in ocations derived from a difference map and their coordinates adjusted to give O—H = 0.84%A. All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.43335 (13)0.99066 (8)0.36405 (5)0.0329 (3)
H10.40410.99090.32930.040*
O20.69023 (15)0.34940 (9)0.41279 (5)0.0414 (3)
N10.69265 (15)0.56857 (10)0.48144 (5)0.0282 (3)
N20.82894 (15)0.29591 (10)0.49432 (5)0.0264 (3)
N30.89959 (15)0.34786 (10)0.54289 (5)0.0261 (3)
C10.57962 (19)0.68917 (12)0.41316 (7)0.0300 (4)
C20.54167 (18)0.76897 (12)0.45379 (7)0.0282 (4)
H20.55010.75480.49380.034*
C30.49214 (18)0.86797 (12)0.43633 (7)0.0287 (4)
H30.46600.92130.46440.034*
C40.48012 (18)0.89043 (12)0.37808 (7)0.0268 (3)
C50.5166 (2)0.81240 (13)0.33727 (7)0.0338 (4)
H50.50870.82710.29730.041*
C60.5647 (2)0.71295 (13)0.35493 (7)0.0386 (4)
H60.58810.65940.32670.046*
C70.6392 (2)0.58501 (13)0.43047 (7)0.0338 (4)
H70.63810.52780.40300.041*
C80.75333 (18)0.46864 (12)0.49509 (6)0.0259 (3)
C90.74727 (19)0.37078 (12)0.46124 (7)0.0290 (4)
C100.84009 (18)0.44934 (12)0.54448 (6)0.0260 (3)
C110.9202 (2)0.28398 (13)0.59429 (6)0.0331 (4)
H11A0.97570.32700.62450.050*
H11B0.98670.22140.58480.050*
H11C0.81190.26060.60810.050*
C120.8719 (2)0.52260 (13)0.59430 (7)0.0379 (4)
H12A0.81260.49670.62810.057*
H12B0.83400.59420.58510.057*
H12C0.99030.52530.60270.057*
C130.90702 (19)0.20424 (11)0.47004 (6)0.0253 (3)
C140.80958 (19)0.12678 (12)0.44266 (6)0.0284 (4)
H140.69320.13320.44190.034*
C150.8844 (2)0.03966 (12)0.41634 (7)0.0318 (4)
H150.8190−0.01360.39720.038*
C161.0533 (2)0.03015 (12)0.41783 (7)0.0319 (4)
H161.1039−0.02950.39970.038*
C171.1490 (2)0.10741 (12)0.44578 (7)0.0321 (4)
H171.26520.09990.44720.038*
C181.07674 (19)0.19580 (12)0.47182 (6)0.0277 (3)
H181.14260.24940.49050.033*
O3−0.07276 (14)0.38608 (8)0.19190 (5)0.0335 (3)
H3A−0.14900.38190.16740.040*
O40.30090 (12)0.99610 (8)0.25745 (4)0.0276 (2)
N4−0.05124 (15)0.88981 (10)0.24542 (5)0.0269 (3)
N50.14278 (14)1.14370 (9)0.27759 (5)0.0238 (3)
N6−0.02363 (14)1.16934 (9)0.27561 (5)0.0241 (3)
C190.00875 (18)0.70312 (11)0.24138 (6)0.0250 (3)
C200.12014 (19)0.62286 (12)0.25460 (6)0.0272 (3)
H200.21850.64140.27490.033*
C210.09102 (19)0.51762 (12)0.23895 (6)0.0274 (3)
H210.16820.46450.24870.033*
C22−0.05170 (19)0.48969 (11)0.20883 (6)0.0254 (3)
C23−0.16547 (19)0.56840 (12)0.19590 (6)0.0282 (4)
H23−0.26440.54960.17600.034*
C24−0.13492 (19)0.67315 (12)0.21193 (6)0.0278 (3)
H24−0.21320.72590.20270.033*
C250.04643 (19)0.81384 (12)0.25703 (6)0.0267 (3)
H250.14700.83020.27650.032*
C26−0.00185 (18)0.99402 (11)0.25961 (6)0.0234 (3)
C270.15973 (18)1.03778 (11)0.26465 (6)0.0231 (3)
C28−0.10963 (18)1.07782 (12)0.26662 (6)0.0250 (3)
C29−0.07842 (19)1.26236 (11)0.30874 (7)0.0297 (4)
H29A−0.19491.27490.30050.045*
H29B−0.01291.32500.29800.045*
H29C−0.06421.24960.35000.045*
C30−0.29252 (18)1.07551 (13)0.26618 (8)0.0356 (4)
H30A−0.33321.09260.30500.053*
H30B−0.33201.00430.25420.053*
H30C−0.33301.12820.23910.053*
C310.26579 (17)1.22415 (11)0.26718 (6)0.0225 (3)
C320.3001 (2)1.25156 (12)0.21120 (7)0.0318 (4)
H320.24061.21890.18010.038*
C330.4207 (2)1.32638 (14)0.20060 (8)0.0422 (4)
H330.44611.34510.16210.051*
C340.5045 (2)1.37399 (14)0.24610 (9)0.0456 (5)
H340.58741.42610.23880.055*
C350.4699 (2)1.34720 (14)0.30215 (9)0.0435 (5)
H350.52801.38110.33320.052*
C360.3501 (2)1.27070 (12)0.31313 (7)0.0321 (4)
H360.32641.25070.35150.039*
O50.43831 (13)1.00160 (8)0.15063 (5)0.0359 (3)
H5A0.39631.00050.18370.043*
O60.69633 (13)0.37408 (8)0.10793 (4)0.0302 (3)
N70.68224 (15)0.57227 (10)0.02772 (5)0.0278 (3)
N80.82733 (15)0.30098 (10)0.02799 (5)0.0255 (3)
N90.88764 (15)0.34003 (10)−0.02407 (5)0.0277 (3)
C370.53272 (18)0.69523 (12)0.08808 (7)0.0277 (4)
C380.46494 (18)0.71054 (13)0.14274 (7)0.0297 (4)
H380.44200.65030.16570.036*
C390.43024 (18)0.81153 (12)0.16433 (7)0.0286 (4)
H390.38440.82010.20170.034*
C400.46269 (18)0.89989 (12)0.13116 (7)0.0279 (4)
C410.5231 (2)0.88589 (13)0.07559 (7)0.0347 (4)
H410.54070.94610.05200.042*
C420.55773 (19)0.78528 (13)0.05449 (7)0.0326 (4)
H420.59930.77700.01640.039*
C430.58390 (18)0.58873 (12)0.07025 (7)0.0278 (4)
H430.54310.52920.09080.033*
C440.74040 (17)0.46900 (12)0.01784 (6)0.0242 (3)
C450.74410 (17)0.38185 (12)0.05700 (6)0.0244 (3)
C460.82686 (18)0.43964 (12)−0.03047 (6)0.0253 (3)
C470.9212 (2)0.26398 (13)−0.07089 (7)0.0368 (4)
H47A0.82270.2200−0.07860.055*
H47B1.01240.2181−0.05980.055*
H47C0.95120.3028−0.10570.055*
C480.8547 (2)0.50055 (13)−0.08359 (7)0.0344 (4)
H48A0.97250.5017−0.09260.052*
H48B0.81650.5738−0.07770.052*
H48C0.79350.4666−0.11560.052*
C490.90208 (19)0.21186 (12)0.05461 (6)0.0275 (3)
C500.8033 (2)0.14313 (13)0.08618 (7)0.0346 (4)
H500.68830.15460.08930.041*
C510.8750 (2)0.05781 (14)0.11303 (7)0.0413 (4)
H510.80910.01120.13540.050*
C521.0412 (2)0.03980 (14)0.10757 (7)0.0413 (4)
H521.0892−0.01960.12570.050*
C531.1383 (2)0.10819 (14)0.07575 (7)0.0389 (4)
H531.25280.09520.07180.047*
C541.06954 (19)0.19547 (13)0.04960 (7)0.0328 (4)
H541.13650.24350.02850.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0364 (6)0.0284 (6)0.0344 (6)0.0082 (5)0.0011 (5)0.0044 (5)
O20.0553 (8)0.0376 (7)0.0314 (7)0.0158 (6)−0.0136 (6)−0.0071 (5)
N10.0293 (7)0.0247 (7)0.0308 (7)0.0052 (6)0.0009 (6)0.0013 (6)
N20.0314 (7)0.0248 (7)0.0229 (7)0.0054 (6)−0.0012 (5)−0.0035 (5)
N30.0327 (7)0.0242 (7)0.0214 (7)0.0034 (6)−0.0009 (5)−0.0002 (5)
C10.0314 (9)0.0266 (9)0.0321 (9)0.0043 (7)−0.0041 (7)−0.0005 (7)
C20.0259 (8)0.0320 (9)0.0268 (8)0.0008 (7)−0.0002 (7)0.0014 (7)
C30.0284 (9)0.0276 (9)0.0302 (9)0.0053 (7)0.0026 (7)−0.0025 (7)
C40.0203 (8)0.0260 (8)0.0341 (9)0.0025 (6)−0.0003 (6)0.0029 (7)
C50.0409 (10)0.0354 (10)0.0255 (9)0.0088 (8)−0.0027 (7)0.0028 (7)
C60.0522 (11)0.0357 (10)0.0280 (9)0.0123 (8)−0.0034 (8)−0.0060 (7)
C70.0406 (10)0.0264 (9)0.0345 (10)0.0079 (7)−0.0024 (8)−0.0034 (7)
C80.0278 (8)0.0226 (8)0.0275 (8)0.0040 (6)0.0034 (7)−0.0005 (6)
C90.0303 (9)0.0287 (9)0.0281 (9)0.0069 (7)−0.0005 (7)0.0011 (7)
C100.0296 (8)0.0220 (8)0.0265 (8)0.0019 (6)0.0047 (7)0.0013 (6)
C110.0453 (10)0.0304 (9)0.0240 (9)0.0043 (8)−0.0014 (7)0.0040 (7)
C120.0550 (11)0.0292 (9)0.0296 (9)0.0049 (8)−0.0027 (8)−0.0024 (7)
C130.0335 (9)0.0196 (8)0.0230 (8)0.0044 (7)0.0031 (6)0.0014 (6)
C140.0302 (9)0.0272 (9)0.0279 (8)−0.0004 (7)0.0040 (7)0.0012 (7)
C150.0417 (10)0.0230 (9)0.0306 (9)−0.0041 (7)0.0045 (7)−0.0010 (7)
C160.0424 (10)0.0234 (9)0.0300 (9)0.0055 (7)0.0064 (7)−0.0003 (7)
C170.0326 (9)0.0291 (9)0.0348 (9)0.0080 (7)0.0024 (7)0.0020 (7)
C180.0307 (9)0.0244 (8)0.0279 (8)0.0024 (7)−0.0014 (7)−0.0001 (7)
O30.0453 (7)0.0227 (6)0.0324 (6)0.0005 (5)−0.0041 (5)−0.0029 (5)
O40.0228 (6)0.0250 (6)0.0351 (6)0.0051 (4)0.0010 (5)−0.0013 (5)
N40.0295 (7)0.0217 (7)0.0295 (7)−0.0011 (6)0.0007 (6)−0.0015 (5)
N50.0186 (6)0.0204 (7)0.0323 (7)0.0015 (5)0.0031 (5)−0.0004 (5)
N60.0193 (6)0.0205 (7)0.0326 (7)0.0030 (5)0.0035 (5)−0.0005 (5)
C190.0300 (8)0.0215 (8)0.0237 (8)−0.0008 (6)0.0032 (6)0.0003 (6)
C200.0286 (8)0.0281 (9)0.0249 (8)−0.0008 (7)−0.0001 (6)0.0007 (6)
C210.0332 (9)0.0236 (8)0.0256 (8)0.0051 (7)0.0017 (7)0.0023 (6)
C220.0356 (9)0.0185 (8)0.0222 (8)−0.0012 (7)0.0049 (7)0.0005 (6)
C230.0282 (8)0.0281 (9)0.0281 (9)−0.0022 (7)−0.0012 (7)0.0006 (7)
C240.0289 (9)0.0236 (8)0.0311 (9)0.0024 (7)0.0005 (7)0.0032 (7)
C250.0288 (8)0.0252 (9)0.0260 (8)−0.0020 (7)0.0005 (7)0.0002 (6)
C260.0252 (8)0.0210 (8)0.0241 (8)0.0004 (6)0.0008 (6)0.0007 (6)
C270.0261 (8)0.0221 (8)0.0213 (8)0.0022 (6)0.0021 (6)0.0016 (6)
C280.0252 (8)0.0250 (8)0.0249 (8)−0.0006 (6)0.0015 (6)0.0022 (6)
C290.0302 (9)0.0221 (8)0.0371 (9)0.0067 (7)0.0084 (7)0.0003 (7)
C300.0233 (8)0.0358 (10)0.0476 (11)−0.0005 (7)0.0032 (7)−0.0003 (8)
C310.0185 (7)0.0188 (8)0.0304 (8)0.0024 (6)0.0020 (6)−0.0004 (6)
C320.0338 (9)0.0308 (9)0.0309 (9)0.0009 (7)0.0038 (7)−0.0024 (7)
C330.0394 (10)0.0380 (10)0.0495 (11)0.0006 (8)0.0162 (9)0.0093 (9)
C340.0252 (9)0.0309 (10)0.0810 (15)−0.0023 (8)0.0056 (9)0.0093 (10)
C350.0346 (10)0.0322 (10)0.0633 (13)−0.0007 (8)−0.0179 (9)−0.0042 (9)
C360.0352 (9)0.0287 (9)0.0323 (9)0.0033 (7)−0.0067 (7)−0.0003 (7)
O50.0404 (7)0.0316 (7)0.0357 (7)0.0082 (5)0.0042 (5)−0.0045 (5)
O60.0321 (6)0.0348 (6)0.0237 (6)0.0006 (5)0.0063 (5)−0.0028 (5)
N70.0279 (7)0.0304 (7)0.0250 (7)0.0035 (6)−0.0018 (6)−0.0042 (6)
N80.0264 (7)0.0277 (7)0.0223 (7)0.0023 (6)0.0043 (5)−0.0024 (5)
N90.0285 (7)0.0320 (8)0.0225 (7)0.0011 (6)0.0050 (5)−0.0053 (6)
C370.0209 (8)0.0321 (9)0.0299 (9)0.0032 (7)−0.0005 (6)−0.0026 (7)
C380.0276 (9)0.0322 (9)0.0293 (9)0.0029 (7)0.0016 (7)0.0004 (7)
C390.0257 (8)0.0353 (9)0.0247 (8)0.0049 (7)0.0013 (6)−0.0028 (7)
C400.0228 (8)0.0286 (9)0.0323 (9)0.0068 (7)−0.0020 (7)−0.0044 (7)
C410.0377 (10)0.0328 (10)0.0338 (9)0.0046 (7)0.0047 (7)0.0026 (7)
C420.0311 (9)0.0364 (10)0.0303 (9)0.0035 (7)0.0063 (7)−0.0006 (7)
C430.0229 (8)0.0298 (9)0.0306 (9)0.0013 (7)−0.0005 (7)−0.0026 (7)
C440.0219 (8)0.0266 (8)0.0238 (8)−0.0006 (6)0.0000 (6)−0.0039 (6)
C450.0178 (7)0.0290 (9)0.0262 (8)−0.0009 (6)−0.0002 (6)−0.0058 (7)
C460.0212 (8)0.0294 (9)0.0251 (8)−0.0011 (6)−0.0022 (6)−0.0039 (6)
C470.0420 (10)0.0414 (10)0.0268 (9)0.0097 (8)0.0018 (7)−0.0101 (7)
C480.0369 (10)0.0386 (10)0.0276 (9)−0.0012 (8)0.0040 (7)−0.0008 (7)
C490.0303 (9)0.0244 (8)0.0276 (8)0.0025 (7)−0.0006 (7)−0.0054 (6)
C500.0330 (9)0.0317 (9)0.0388 (10)−0.0027 (7)0.0010 (7)−0.0014 (8)
C510.0495 (12)0.0335 (10)0.0408 (11)−0.0041 (8)−0.0002 (9)0.0038 (8)
C520.0519 (12)0.0343 (10)0.0378 (10)0.0088 (9)−0.0068 (9)−0.0013 (8)
C530.0340 (10)0.0434 (11)0.0394 (10)0.0113 (8)−0.0032 (8)−0.0013 (8)
C540.0296 (9)0.0351 (10)0.0335 (9)0.0013 (7)0.0019 (7)−0.0040 (7)
Geometric parameters (Å, º) top
O1—C41.3630 (17)C25—H250.9500
O1—H10.8402C26—C281.3839 (19)
O2—C91.2369 (18)C26—C271.419 (2)
N1—C71.2791 (19)C28—C301.485 (2)
N1—C81.3942 (18)C29—H29A0.9800
N2—C91.3966 (18)C29—H29B0.9800
N2—N31.4069 (16)C29—H29C0.9800
N2—C131.4272 (18)C30—H30A0.9800
N3—C101.3669 (18)C30—H30B0.9800
N3—C111.4593 (18)C30—H30C0.9800
C1—C61.394 (2)C31—C321.378 (2)
C1—C21.399 (2)C31—C361.380 (2)
C1—C71.462 (2)C32—C331.374 (2)
C2—C31.378 (2)C32—H320.9500
C2—H20.9500C33—C341.376 (3)
C3—C41.388 (2)C33—H330.9500
C3—H30.9500C34—C351.378 (3)
C4—C51.383 (2)C34—H340.9500
C5—C61.381 (2)C35—C361.385 (2)
C5—H50.9500C35—H350.9500
C6—H60.9500C36—H360.9500
C7—H70.9500O5—C401.3617 (17)
C8—C101.370 (2)O5—H5A0.8402
C8—C91.444 (2)O6—C451.2496 (17)
C10—C121.482 (2)N7—C431.2863 (18)
C11—H11A0.9800N7—C441.3992 (18)
C11—H11B0.9800N8—C451.3900 (18)
C11—H11C0.9800N8—N91.3993 (16)
C12—H12A0.9800N8—C491.4286 (19)
C12—H12B0.9800N9—C461.3597 (18)
C12—H12C0.9800N9—C471.4597 (18)
C13—C181.384 (2)C37—C381.395 (2)
C13—C141.388 (2)C37—C421.397 (2)
C14—C151.389 (2)C37—C431.457 (2)
C14—H140.9500C38—C391.385 (2)
C15—C161.378 (2)C38—H380.9500
C15—H150.9500C39—C401.384 (2)
C16—C171.384 (2)C39—H390.9500
C16—H160.9500C40—C411.389 (2)
C17—C181.390 (2)C41—C421.377 (2)
C17—H170.9500C41—H410.9500
C18—H180.9500C42—H420.9500
O3—C221.3584 (17)C43—H430.9500
O3—H3A0.8402C44—C461.371 (2)
O4—C271.2763 (16)C44—C451.435 (2)
N4—C251.2798 (18)C46—C481.479 (2)
N4—C261.3949 (18)C47—H47A0.9800
N5—C271.3648 (18)C47—H47B0.9800
N5—N61.3941 (16)C47—H47C0.9800
N5—C311.4350 (18)C48—H48A0.9800
N6—C281.3482 (18)C48—H48B0.9800
N6—C291.4593 (17)C48—H48C0.9800
C19—C241.394 (2)C49—C541.383 (2)
C19—C201.400 (2)C49—C501.390 (2)
C19—C251.457 (2)C50—C511.382 (2)
C20—C211.379 (2)C50—H500.9500
C20—H200.9500C51—C521.378 (2)
C21—C221.389 (2)C51—H510.9500
C21—H210.9500C52—C531.383 (2)
C22—C231.397 (2)C52—H520.9500
C23—C241.377 (2)C53—C541.385 (2)
C23—H230.9500C53—H530.9500
C24—H240.9500C54—H540.9500
C4—O1—H1109.3N5—C27—C26106.62 (12)
C7—N1—C8119.66 (13)N6—C28—C26109.55 (13)
C9—N2—N3109.04 (12)N6—C28—C30121.58 (13)
C9—N2—C13123.24 (12)C26—C28—C30128.85 (14)
N3—N2—C13119.37 (12)N6—C29—H29A109.5
C10—N3—N2106.96 (11)N6—C29—H29B109.5
C10—N3—C11123.17 (12)H29A—C29—H29B109.5
N2—N3—C11116.63 (12)N6—C29—H29C109.5
C6—C1—C2117.94 (14)H29A—C29—H29C109.5
C6—C1—C7120.32 (15)H29B—C29—H29C109.5
C2—C1—C7121.70 (14)C28—C30—H30A109.5
C3—C2—C1120.59 (14)C28—C30—H30B109.5
C3—C2—H2119.7H30A—C30—H30B109.5
C1—C2—H2119.7C28—C30—H30C109.5
C2—C3—C4120.53 (14)H30A—C30—H30C109.5
C2—C3—H3119.7H30B—C30—H30C109.5
C4—C3—H3119.7C32—C31—C36121.27 (14)
O1—C4—C5123.04 (14)C32—C31—N5119.12 (13)
O1—C4—C3117.26 (13)C36—C31—N5119.59 (14)
C5—C4—C3119.70 (14)C33—C32—C31119.66 (16)
C6—C5—C4119.61 (15)C33—C32—H32120.2
C6—C5—H5120.2C31—C32—H32120.2
C4—C5—H5120.2C32—C33—C34119.56 (17)
C5—C6—C1121.62 (15)C32—C33—H33120.2
C5—C6—H6119.2C34—C33—H33120.2
C1—C6—H6119.2C33—C34—C35120.93 (16)
N1—C7—C1122.03 (15)C33—C34—H34119.5
N1—C7—H7119.0C35—C34—H34119.5
C1—C7—H7119.0C34—C35—C36119.84 (16)
C10—C8—N1123.46 (14)C34—C35—H35120.1
C10—C8—C9107.64 (13)C36—C35—H35120.1
N1—C8—C9128.82 (13)C31—C36—C35118.73 (16)
O2—C9—N2122.70 (14)C31—C36—H36120.6
O2—C9—C8131.93 (14)C35—C36—H36120.6
N2—C9—C8105.34 (13)C40—O5—H5A109.6
N3—C10—C8110.19 (13)C43—N7—C44118.60 (13)
N3—C10—C12121.57 (13)C45—N8—N9109.06 (12)
C8—C10—C12128.24 (14)C45—N8—C49125.18 (12)
N3—C11—H11A109.5N9—N8—C49120.77 (11)
N3—C11—H11B109.5C46—N9—N8107.53 (11)
H11A—C11—H11B109.5C46—N9—C47125.54 (13)
N3—C11—H11C109.5N8—N9—C47118.42 (12)
H11A—C11—H11C109.5C38—C37—C42117.58 (14)
H11B—C11—H11C109.5C38—C37—C43119.10 (14)
C10—C12—H12A109.5C42—C37—C43123.19 (14)
C10—C12—H12B109.5C39—C38—C37121.56 (15)
H12A—C12—H12B109.5C39—C38—H38119.2
C10—C12—H12C109.5C37—C38—H38119.2
H12A—C12—H12C109.5C40—C39—C38119.73 (14)
H12B—C12—H12C109.5C40—C39—H39120.1
C18—C13—C14121.21 (14)C38—C39—H39120.1
C18—C13—N2120.28 (14)O5—C40—C39122.79 (14)
C14—C13—N2118.45 (13)O5—C40—C41117.71 (14)
C13—C14—C15119.14 (14)C39—C40—C41119.50 (14)
C13—C14—H14120.4C42—C41—C40120.38 (15)
C15—C14—H14120.4C42—C41—H41119.8
C16—C15—C14120.28 (15)C40—C41—H41119.8
C16—C15—H15119.9C41—C42—C37121.12 (15)
C14—C15—H15119.9C41—C42—H42119.4
C15—C16—C17120.02 (15)C37—C42—H42119.4
C15—C16—H16120.0N7—C43—C37122.46 (15)
C17—C16—H16120.0N7—C43—H43118.8
C16—C17—C18120.62 (15)C37—C43—H43118.8
C16—C17—H17119.7C46—C44—N7123.26 (14)
C18—C17—H17119.7C46—C44—C45107.84 (13)
C13—C18—C17118.72 (15)N7—C44—C45128.33 (13)
C13—C18—H18120.6O6—C45—N8122.91 (14)
C17—C18—H18120.6O6—C45—C44131.57 (14)
C22—O3—H3A109.0N8—C45—C44105.39 (13)
C25—N4—C26118.39 (13)N9—C46—C44109.75 (13)
C27—N5—N6109.15 (11)N9—C46—C48121.71 (13)
C27—N5—C31124.66 (12)C44—C46—C48128.54 (14)
N6—N5—C31119.98 (11)N9—C47—H47A109.5
C28—N6—N5107.53 (11)N9—C47—H47B109.5
C28—N6—C29126.16 (12)H47A—C47—H47B109.5
N5—N6—C29118.27 (12)N9—C47—H47C109.5
C24—C19—C20117.65 (14)H47A—C47—H47C109.5
C24—C19—C25122.16 (14)H47B—C47—H47C109.5
C20—C19—C25120.16 (14)C46—C48—H48A109.5
C21—C20—C19121.82 (15)C46—C48—H48B109.5
C21—C20—H20119.1H48A—C48—H48B109.5
C19—C20—H20119.1C46—C48—H48C109.5
C20—C21—C22119.61 (14)H48A—C48—H48C109.5
C20—C21—H21120.2H48B—C48—H48C109.5
C22—C21—H21120.2C54—C49—C50120.93 (15)
O3—C22—C21117.97 (13)C54—C49—N8120.48 (14)
O3—C22—C23122.58 (14)C50—C49—N8118.58 (14)
C21—C22—C23119.44 (14)C51—C50—C49119.05 (16)
C24—C23—C22120.30 (14)C51—C50—H50120.5
C24—C23—H23119.9C49—C50—H50120.5
C22—C23—H23119.9C52—C51—C50120.49 (17)
C23—C24—C19121.16 (14)C52—C51—H51119.8
C23—C24—H24119.4C50—C51—H51119.8
C19—C24—H24119.4C51—C52—C53120.06 (16)
N4—C25—C19122.26 (14)C51—C52—H52120.0
N4—C25—H25118.9C53—C52—H52120.0
C19—C25—H25118.9C52—C53—C54120.32 (16)
C28—C26—N4123.84 (13)C52—C53—H53119.8
C28—C26—C27106.85 (13)C54—C53—H53119.8
N4—C26—C27129.10 (13)C49—C54—C53119.14 (16)
O4—C27—N5121.76 (13)C49—C54—H54120.4
O4—C27—C26131.57 (14)C53—C54—H54120.4
C9—N2—N3—C109.42 (15)N4—C26—C27—O40.6 (3)
C13—N2—N3—C10158.68 (12)C28—C26—C27—N53.35 (16)
C9—N2—N3—C11151.86 (13)N4—C26—C27—N5178.09 (14)
C13—N2—N3—C11−58.87 (17)N5—N6—C28—C26−3.20 (16)
C6—C1—C2—C3−0.4 (2)C29—N6—C28—C26−150.99 (14)
C7—C1—C2—C3177.34 (15)N5—N6—C28—C30175.78 (13)
C1—C2—C3—C4−0.4 (2)C29—N6—C28—C3028.0 (2)
C2—C3—C4—O1−178.79 (13)N4—C26—C28—N6−175.15 (13)
C2—C3—C4—C50.6 (2)C27—C26—C28—N6−0.06 (16)
O1—C4—C5—C6179.40 (15)N4—C26—C28—C306.0 (2)
C3—C4—C5—C60.0 (2)C27—C26—C28—C30−178.94 (15)
C4—C5—C6—C1−0.9 (3)C27—N5—C31—C3269.87 (18)
C2—C1—C6—C51.1 (3)N6—N5—C31—C32−79.37 (17)
C7—C1—C6—C5−176.72 (16)C27—N5—C31—C36−108.60 (17)
C8—N1—C7—C1−177.79 (14)N6—N5—C31—C36102.17 (16)
C6—C1—C7—N1162.55 (16)C36—C31—C32—C330.2 (2)
C2—C1—C7—N1−15.1 (3)N5—C31—C32—C33−178.24 (14)
C7—N1—C8—C10167.52 (15)C31—C32—C33—C34−0.8 (2)
C7—N1—C8—C9−8.9 (2)C32—C33—C34—C350.4 (3)
N3—N2—C9—O2171.47 (15)C33—C34—C35—C360.5 (3)
C13—N2—C9—O223.6 (2)C32—C31—C36—C350.7 (2)
N3—N2—C9—C8−6.85 (16)N5—C31—C36—C35179.17 (13)
C13—N2—C9—C8−154.68 (13)C34—C35—C36—C31−1.1 (2)
C10—C8—C9—O2−176.28 (18)C45—N8—N9—C46−6.79 (15)
N1—C8—C9—O20.5 (3)C49—N8—N9—C46−163.01 (13)
C10—C8—C9—N21.81 (17)C45—N8—N9—C47−156.57 (13)
N1—C8—C9—N2178.63 (14)C49—N8—N9—C4747.21 (18)
N2—N3—C10—C8−8.28 (16)C42—C37—C38—C39−2.9 (2)
C11—N3—C10—C8−147.67 (14)C43—C37—C38—C39173.08 (14)
N2—N3—C10—C12172.00 (14)C37—C38—C39—C400.2 (2)
C11—N3—C10—C1232.6 (2)C38—C39—C40—O5−177.08 (14)
N1—C8—C10—N3−172.97 (13)C38—C39—C40—C412.8 (2)
C9—C8—C10—N34.06 (17)O5—C40—C41—C42176.88 (14)
N1—C8—C10—C126.7 (3)C39—C40—C41—C42−3.0 (2)
C9—C8—C10—C12−176.24 (15)C40—C41—C42—C370.2 (2)
C9—N2—C13—C18112.19 (17)C38—C37—C42—C412.7 (2)
N3—N2—C13—C18−32.53 (19)C43—C37—C42—C41−173.10 (15)
C9—N2—C13—C14−65.07 (19)C44—N7—C43—C37172.49 (13)
N3—N2—C13—C14150.21 (13)C38—C37—C43—N7−162.46 (14)
C18—C13—C14—C15−0.4 (2)C42—C37—C43—N713.3 (2)
N2—C13—C14—C15176.85 (13)C43—N7—C44—C46170.79 (14)
C13—C14—C15—C160.5 (2)C43—N7—C44—C45−19.0 (2)
C14—C15—C16—C170.2 (2)N9—N8—C45—O6−170.23 (13)
C15—C16—C17—C18−0.9 (2)C49—N8—C45—O6−15.3 (2)
C14—C13—C18—C17−0.3 (2)N9—N8—C45—C446.01 (15)
N2—C13—C18—C17−177.52 (13)C49—N8—C45—C44160.93 (13)
C16—C17—C18—C131.0 (2)C46—C44—C45—O6172.67 (15)
C27—N5—N6—C285.40 (15)N7—C44—C45—O61.2 (3)
C31—N5—N6—C28158.95 (13)C46—C44—C45—N8−3.10 (16)
C27—N5—N6—C29156.14 (12)N7—C44—C45—N8−174.53 (14)
C31—N5—N6—C29−50.31 (17)N8—N9—C46—C444.76 (16)
C24—C19—C20—C210.5 (2)C47—N9—C46—C44151.81 (14)
C25—C19—C20—C21−178.02 (13)N8—N9—C46—C48−174.57 (13)
C19—C20—C21—C220.5 (2)C47—N9—C46—C48−27.5 (2)
C20—C21—C22—O3177.13 (13)N7—C44—C46—N9170.93 (13)
C20—C21—C22—C23−1.4 (2)C45—C44—C46—N9−1.03 (16)
O3—C22—C23—C24−177.20 (13)N7—C44—C46—C48−9.8 (2)
C21—C22—C23—C241.2 (2)C45—C44—C46—C48178.24 (14)
C22—C23—C24—C19−0.2 (2)C45—N8—C49—C54−119.28 (16)
C20—C19—C24—C23−0.6 (2)N9—N8—C49—C5432.9 (2)
C25—C19—C24—C23177.84 (14)C45—N8—C49—C5059.9 (2)
C26—N4—C25—C19−177.08 (13)N9—N8—C49—C50−147.93 (14)
C24—C19—C25—N41.1 (2)C54—C49—C50—C510.4 (2)
C20—C19—C25—N4179.49 (14)N8—C49—C50—C51−178.77 (14)
C25—N4—C26—C28−158.83 (14)C49—C50—C51—C52−1.4 (3)
C25—N4—C26—C2727.2 (2)C50—C51—C52—C531.0 (3)
N6—N5—C27—O4172.41 (12)C51—C52—C53—C540.5 (3)
C31—N5—C27—O420.4 (2)C50—C49—C54—C531.1 (2)
N6—N5—C27—C26−5.35 (15)N8—C49—C54—C53−179.82 (14)
C31—N5—C27—C26−157.38 (13)C52—C53—C54—C49−1.5 (2)
C28—C26—C27—O4−174.11 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O40.841.862.6947 (14)170
O3—H3A···O6i0.841.862.6993 (15)175
O5—H5A···O40.841.882.7218 (15)179
C7—H7···O20.952.303.009 (2)131
C25—H25···O40.952.463.0612 (18)121
C43—H43···O60.952.362.9989 (18)124
C33—H33···O6ii0.952.423.168 (2)135
C35—H35···O2ii0.952.313.122 (2)143
Symmetry codes: (i) x−1, y, z; (ii) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O40.841.862.6947 (14)170
O3—H3A···O6i0.841.862.6993 (15)175
O5—H5A···O40.841.882.7218 (15)179
C7—H7···O20.952.303.009 (2)131
C25—H25···O40.952.463.0612 (18)121
C43—H43···O60.952.362.9989 (18)124
C33—H33···O6ii0.952.423.168 (2)135
C35—H35···O2ii0.952.313.122 (2)143
Symmetry codes: (i) x−1, y, z; (ii) x, y+1, z.
 

Acknowledgements

The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

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ISSN: 2056-9890
Volume 71| Part 12| December 2015| Pages o947-o948
https://doi.org/10.1107/S2056989015021325
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