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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 4| April 2015| Page o235
doi:10.1107/S2056989015004661

Crystal structure of N-[(2-hy­dr­oxy­naphthalen-1-yl)(4-methyl­phen­yl)meth­yl]acetamide

CROSSMARK_Color_square_no_text.svg
Sharanbasappa Khanapure,a Gajanan Rashinkar,a Tarulata Chhowala,b Sumati Anthalc and Rajni Kantc*

aDepartment of Chemistry, Shivaji University, Kolhapur 416 004, M.S., India, bVeerNarmad South Gujrat University, Surat 395 007, Gujrat, India, and cX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India
*Correspondence e-mail: rkant.ju@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 2 March 2015; accepted 6 March 2015; online 14 March 2015)

In the title mol­ecule, C20H19NO2, the naphthalene ring system subtends a dihedral angle of 82.50 (7)° with the benzene ring and an intra­molecular N—H⋯O hydrogen bond closes an S(6) ring. In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds, which generate C(8) chains propagating in the [010] direction. The crystal structure also features weak π–π inter­actions [centroid–centroid separation = 3.7246 (10) Å].

CCDC reference: 959797

Similar articles

1. Related literature

For background to N-(substituted phen­yl)acetamides, see: Schleiss et al. (2008[Schleiss, M., Eickhoff, J., Auerochs, S., Leis, M., Abele, S., Rechter, S., Choi, S., Anderson, J., Scott, G., Rawlinson, W., Michel, D., Ensminger, S., Klebl, B., Stamminger, T. & Marschall, M. (2008). Antiviral Res. 79, 49-61.]). For further synthetic details, see: Shaterian et al. (2008[Shaterian, H. R., Hosseinian, A. & Ghashang, M. (2008). Synth. Commun. 38, 3375-3389.]). For related structures, see: Mosslemin et al. (2007[Mosslemin, M. H., Arab-Salmanabadi, S. & Masoudi, M. (2007). Acta Cryst. E63, o444-o445.]); NizamMohideen et al. (2009[NizamMohideen, M., SubbiahPandi, A., Panneer Selvam, N. & Perumal, P. T. (2009). Acta Cryst. E65, o714-o715.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C20H19NO2

  • Mr = 305.36

  • Monoclinic, P 21 /n

  • a = 10.4324 (4) Å

  • b = 14.0786 (5) Å

  • c = 11.0356 (4) Å

  • β = 98.741 (2)°

  • V = 1602.01 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 296 K

  • 0.25 × 0.20 × 0.20 mm

2.2. Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.980, Tmax = 0.984

  • 12272 measured reflections

  • 2821 independent reflections

  • 2391 reflections with I > 2σ(I)

  • Rint = 0.020

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.122

  • S = 1.05

  • 2821 reflections

  • 209 parameters

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯O1 0.86 2.20 2.7396 (16) 121
O1—H1B⋯O2i 0.82 1.85 2.6498 (15) 165
Symmetry code: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 959797

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2056989015004661/hb7375sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015004661/hb7375Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015004661/hb7375Isup3.cml

checkCIF report


Comment top

1-Amidoalkyl-2-naphthol scaffolds are of significant medicinal relevance since they can be converted into hypertensive and bradycardiac active 1-aminoalkyl-2-naphthols by amine hydrolysis reactions [Schleiss et al., 2008]. As part of our studies in this area, we now describe the synthesis and structure of the title compound, (I).

The conformation of (I), together with the atom-numbering scheme, is shown in Fig. 1. In the structure, all bond lengths are comparable with those in previously reported structures (Mosslemin et al., 2007, NizamMohideen et al., 2009). Atom O1 deviating by 0.009 (1) Å from the least squares plane of the naphthalene ring. The dihedral angle between the naphthalene and benzene ring(C2/C3/C4/C5/C7/C8) is 82.5 (10)°. Examination of non bonded contacts reveals the presence of one N—H···O intramolecular hydrogen bond between N1 and hydroxyl atom O1 via H1 which results in the formation of pseudo six membered ring with S(6) graph-set motif. In this crystal, adjacent molecules are interconnected through O—H···O hydrogen bonds, which link the molecules into chains running along b axis. The crystal structure is further stabilized by π-π interactions between phenyl rings [centroid-centroid separation = 3.725 Å, interplaner spacing = 3.571 Å and centroid shift = 1.06 Å] where Cg1 and Cg2 represents the centre of gravity of rings (C2/C3/C4/C5/C7/C8) and (C11—C16), respectively.

Related literature top

For background to N-(substituted phenyl)acetamides, see: Schleiss et al. (2008). For further synthetic details, see: Shaterian et al. (2008). For related structures, see: Mosslemin et al. (2007); NizamMohideen et al. (2009).

Experimental top

The compound N-[(phenyl)-(2-hydroxy-naphthalen-1-yl)- methyl]acetamide was synthesized by using benzaldehyde, 2-naphthol and acetamide by using Cp2ZrCl2 as a catalyst at room temperature. A mixture of 2-naphthol (1 mmol), benzaldehyde (1 mmol), acetamide (1.2 mmol) and zirconocene dichloride (20 mol%) was stirred in ethylene dichloride (5 ml) at room temperature for 10 h. After completion of reaction, as indicated by TLC, the reaction mixture was quenched in cold water. The obtained crude solid was filtered and purified by column chromatography on silica gel (Merck. 60–120 mesh, ethyl acetate: hexane)to afford the pure product in 72% yield. The identity of the compound was ascertained on the basis of FTIR, 1HNMR and 13CNMR spectroscopy as well as by mass spectrometry. The physical and spectroscopic data are consistent with the proposed structure and are in harmony with the literature values (Shaterian et al., 2008). The IR spectrum exhibits broad absorption band at 3435 for O—H stretching and a sharp band at 3230 for N—H stretching of amide. The presence of amide group was apparent from strong absorptions at 1638 (C=O stretching) and 1597 (C—N stretching)·The 1H NMR (300 MHz, DMSO-d6) spectra of N-[(2-Hydroxynaphthalen-1-yl)(4-methylphenyl) methyl]acetamideexhibited singlets at δ 2.01 and 2.13 for protons of two methylgropus. The signals for amidic N—H and phenolic O—H protons appeared at 8.20 (s) and 9,96 (s) respectively. The two multiplets in the region 7.00–7.82 were assigned to ten aromatic protons and one methine proton. The proton decoupled 13 C NMR (75 MHz, DMSO-d6)spectra of N-[(2-Hydroxynaphthalen-1-yl) (4-methylphenyl)methyl]acetamidedisplay 19 distinct signals at 170.26, 153.43,139.67, 135.80, 132.64, 129.72, 129.08,128.86, 126.92,126.36, 123.53,122.98, 119.18, 118.82which is in agreement with the proposed structure. The Mass spectrum MS (EI): of this compound displayed the molecular ion peak at m/z = 306 (M+) which is in agreement with the proposed structure.

Refinement top

All H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C—H distances of 0.93–0.98 A; and with Uiso(H) = 1.2Ueq(C), except for the methyl groups where Uiso(H) = 1.5Ueq(C).

Structure description top

1-Amidoalkyl-2-naphthol scaffolds are of significant medicinal relevance since they can be converted into hypertensive and bradycardiac active 1-aminoalkyl-2-naphthols by amine hydrolysis reactions [Schleiss et al., 2008]. As part of our studies in this area, we now describe the synthesis and structure of the title compound, (I).

The conformation of (I), together with the atom-numbering scheme, is shown in Fig. 1. In the structure, all bond lengths are comparable with those in previously reported structures (Mosslemin et al., 2007, NizamMohideen et al., 2009). Atom O1 deviating by 0.009 (1) Å from the least squares plane of the naphthalene ring. The dihedral angle between the naphthalene and benzene ring(C2/C3/C4/C5/C7/C8) is 82.5 (10)°. Examination of non bonded contacts reveals the presence of one N—H···O intramolecular hydrogen bond between N1 and hydroxyl atom O1 via H1 which results in the formation of pseudo six membered ring with S(6) graph-set motif. In this crystal, adjacent molecules are interconnected through O—H···O hydrogen bonds, which link the molecules into chains running along b axis. The crystal structure is further stabilized by π-π interactions between phenyl rings [centroid-centroid separation = 3.725 Å, interplaner spacing = 3.571 Å and centroid shift = 1.06 Å] where Cg1 and Cg2 represents the centre of gravity of rings (C2/C3/C4/C5/C7/C8) and (C11—C16), respectively.

For background to N-(substituted phenyl)acetamides, see: Schleiss et al. (2008). For further synthetic details, see: Shaterian et al. (2008). For related structures, see: Mosslemin et al. (2007); NizamMohideen et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular configuration of (I). Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The packing arrangement of molecules viewed down the b axis.
N-[(2-Hydroxynaphthalen-1-yl)(4-methylphenyl)methyl]acetamide top
Crystal data top
C20H19NO2F(000) = 648
Mr = 305.36Dx = 1.266 Mg m−3
Dm = 1.264 Mg m−3
Dm measured by not measured
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6588 reflections
a = 10.4324 (4) Åθ = 2.5–28.2°
b = 14.0786 (5) ŵ = 0.08 mm−1
c = 11.0356 (4) ÅT = 296 K
β = 98.741 (2)°Block, colourless
V = 1602.01 (10) Å30.25 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer		2821 independent reflections
Radiation source: fine-focus sealed tube2391 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
φ and ω scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		h = −12→12
Tmin = 0.980, Tmax = 0.984k = −15→16
12272 measured reflectionsl = −13→10
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0595P)2 + 0.5039P]
where P = (Fo2 + 2Fc2)/3
2821 reflections(Δ/σ)max < 0.001
209 parametersΔρmax = 0.26 e Å−3
0 restraintsΔρmin = −0.16 e Å−3
Crystal data top
C20H19NO2V = 1602.01 (10) Å3
Mr = 305.36Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.4324 (4) ŵ = 0.08 mm−1
b = 14.0786 (5) ÅT = 296 K
c = 11.0356 (4) Å0.25 × 0.20 × 0.20 mm
β = 98.741 (2)°
Data collection top
Bruker APEXII CCD
diffractometer		2821 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		2391 reflections with I > 2σ(I)
Tmin = 0.980, Tmax = 0.984Rint = 0.020
12272 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.122H-atom parameters constrained
S = 1.05Δρmax = 0.26 e Å−3
2821 reflectionsΔρmin = −0.16 e Å−3
209 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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) top
xyzUiso*/Ueq
C10.70578 (14)0.25289 (10)0.87937 (14)0.0381 (3)
H10.69380.31000.92710.046*
C20.78237 (14)0.18214 (10)0.96674 (14)0.0379 (3)
C30.72170 (16)0.11312 (12)1.02635 (16)0.0510 (4)
H30.63180.10791.01100.061*
C40.79230 (18)0.05162 (13)1.10855 (18)0.0598 (5)
H40.74880.00581.14740.072*
C50.92559 (18)0.05652 (12)1.13422 (16)0.0527 (4)
C61.0028 (2)−0.01018 (15)1.2240 (2)0.0748 (6)
H6A1.09340.00451.23000.112*
H6B0.9881−0.07441.19610.112*
H6C0.9761−0.00321.30300.112*
C70.98531 (17)0.12598 (14)1.07495 (17)0.0578 (5)
H71.07520.13121.09040.069*
C80.91576 (16)0.18805 (12)0.99343 (16)0.0508 (4)
H80.95930.23460.95590.061*
C90.83298 (15)0.36630 (11)0.77479 (15)0.0426 (4)
C100.89465 (19)0.38493 (14)0.66304 (18)0.0614 (5)
H10A0.88560.32980.61120.092*
H10B0.98500.39880.68720.092*
H10C0.85290.43810.61910.092*
C110.57167 (14)0.21783 (10)0.82499 (13)0.0358 (3)
C120.56126 (15)0.14446 (10)0.74112 (14)0.0393 (4)
C130.44045 (16)0.10999 (11)0.68525 (15)0.0466 (4)
H130.43610.06110.62800.056*
C140.32992 (16)0.14825 (12)0.71506 (16)0.0493 (4)
H140.25010.12550.67720.059*
C150.33371 (15)0.22181 (12)0.80244 (15)0.0448 (4)
C160.45625 (14)0.25743 (10)0.85831 (13)0.0385 (4)
C170.45539 (16)0.33110 (12)0.94630 (16)0.0492 (4)
H170.53380.35560.98510.059*
C180.34242 (18)0.36669 (15)0.97517 (19)0.0632 (5)
H180.34500.41501.03300.076*
C190.22255 (18)0.33162 (16)0.9191 (2)0.0685 (6)
H190.14590.35650.93910.082*
C200.21922 (17)0.26107 (14)0.83527 (19)0.0601 (5)
H200.13930.23780.79830.072*
N10.77811 (12)0.28136 (9)0.78136 (12)0.0424 (3)
H1A0.78560.24080.72460.051*
O10.67338 (11)0.10791 (8)0.71078 (11)0.0497 (3)
H1B0.65950.05460.68180.075*
O20.83171 (12)0.42693 (8)0.85572 (11)0.0548 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0395 (8)0.0307 (7)0.0462 (8)−0.0022 (6)0.0133 (7)−0.0001 (6)
C20.0374 (8)0.0347 (8)0.0420 (8)−0.0016 (6)0.0073 (6)−0.0045 (6)
C30.0395 (9)0.0529 (10)0.0601 (10)−0.0034 (7)0.0065 (8)0.0127 (8)
C40.0596 (11)0.0546 (11)0.0628 (12)−0.0048 (8)0.0017 (9)0.0175 (9)
C50.0580 (11)0.0473 (10)0.0486 (10)0.0063 (8)−0.0051 (8)−0.0065 (7)
C60.0827 (15)0.0659 (13)0.0670 (13)0.0196 (11)−0.0172 (11)−0.0003 (10)
C70.0391 (9)0.0678 (12)0.0630 (11)0.0021 (8)−0.0038 (8)−0.0070 (9)
C80.0410 (9)0.0523 (10)0.0587 (10)−0.0089 (7)0.0063 (7)−0.0005 (8)
C90.0406 (8)0.0347 (8)0.0531 (9)−0.0017 (6)0.0090 (7)0.0078 (7)
C100.0683 (12)0.0529 (10)0.0681 (12)−0.0112 (9)0.0271 (10)0.0078 (9)
C110.0382 (8)0.0299 (7)0.0399 (8)−0.0006 (6)0.0079 (6)0.0058 (6)
C120.0444 (8)0.0305 (7)0.0443 (8)0.0006 (6)0.0108 (7)0.0051 (6)
C130.0550 (10)0.0365 (8)0.0472 (9)−0.0065 (7)0.0045 (7)−0.0016 (7)
C140.0449 (9)0.0481 (9)0.0527 (10)−0.0073 (7)0.0004 (7)0.0039 (7)
C150.0400 (9)0.0455 (9)0.0493 (9)−0.0001 (7)0.0078 (7)0.0082 (7)
C160.0405 (8)0.0361 (8)0.0400 (8)−0.0001 (6)0.0090 (6)0.0063 (6)
C170.0449 (9)0.0520 (10)0.0528 (10)−0.0019 (7)0.0138 (7)−0.0055 (8)
C180.0571 (11)0.0668 (12)0.0699 (12)0.0024 (9)0.0240 (9)−0.0157 (10)
C190.0452 (10)0.0796 (14)0.0850 (14)0.0078 (9)0.0238 (10)−0.0075 (11)
C200.0389 (9)0.0704 (12)0.0715 (12)−0.0007 (8)0.0103 (8)−0.0005 (10)
N10.0474 (8)0.0336 (7)0.0491 (8)−0.0052 (5)0.0166 (6)−0.0001 (5)
O10.0517 (7)0.0348 (6)0.0656 (8)0.0005 (5)0.0183 (6)−0.0076 (5)
O20.0699 (8)0.0352 (6)0.0617 (8)−0.0099 (5)0.0179 (6)0.0019 (5)
Geometric parameters (Å, º) top
C1—N11.4657 (19)C10—H10B0.9600
C1—C111.519 (2)C10—H10C0.9600
C1—C21.525 (2)C11—C121.380 (2)
C1—H10.9800C11—C161.425 (2)
C2—C31.380 (2)C12—O11.3653 (18)
C2—C81.380 (2)C12—C131.403 (2)
C3—C41.383 (2)C13—C141.358 (2)
C3—H30.9300C13—H130.9300
C4—C51.378 (3)C14—C151.412 (2)
C4—H40.9300C14—H140.9300
C5—C71.377 (3)C15—C201.412 (2)
C5—C61.506 (3)C15—C161.423 (2)
C6—H6A0.9600C16—C171.422 (2)
C6—H6B0.9600C17—C181.362 (2)
C6—H6C0.9600C17—H170.9300
C7—C81.379 (3)C18—C191.398 (3)
C7—H70.9300C18—H180.9300
C8—H80.9300C19—C201.354 (3)
C9—O21.237 (2)C19—H190.9300
C9—N11.3325 (19)C20—H200.9300
C9—C101.498 (2)N1—H1A0.8600
C10—H10A0.9600O1—H1B0.8200
N1—C1—C11110.12 (12)H10A—C10—H10C109.5
N1—C1—C2111.48 (12)H10B—C10—H10C109.5
C11—C1—C2113.60 (11)C12—C11—C16118.85 (14)
N1—C1—H1107.1C12—C11—C1118.83 (13)
C11—C1—H1107.1C16—C11—C1122.32 (13)
C2—C1—H1107.1O1—C12—C11117.61 (13)
C3—C2—C8117.48 (15)O1—C12—C13120.52 (14)
C3—C2—C1121.80 (13)C11—C12—C13121.84 (14)
C8—C2—C1120.65 (14)C14—C13—C12119.71 (15)
C2—C3—C4121.09 (16)C14—C13—H13120.1
C2—C3—H3119.5C12—C13—H13120.1
C4—C3—H3119.5C13—C14—C15121.33 (15)
C5—C4—C3121.59 (17)C13—C14—H14119.3
C5—C4—H4119.2C15—C14—H14119.3
C3—C4—H4119.2C14—C15—C20121.69 (16)
C7—C5—C4116.94 (16)C14—C15—C16118.98 (15)
C7—C5—C6121.31 (18)C20—C15—C16119.33 (16)
C4—C5—C6121.74 (19)C17—C16—C15117.02 (14)
C5—C6—H6A109.5C17—C16—C11123.71 (14)
C5—C6—H6B109.5C15—C16—C11119.26 (14)
H6A—C6—H6B109.5C18—C17—C16121.57 (16)
C5—C6—H6C109.5C18—C17—H17119.2
H6A—C6—H6C109.5C16—C17—H17119.2
H6B—C6—H6C109.5C17—C18—C19120.91 (18)
C5—C7—C8121.93 (16)C17—C18—H18119.5
C5—C7—H7119.0C19—C18—H18119.5
C8—C7—H7119.0C20—C19—C18119.33 (17)
C7—C8—C2120.96 (16)C20—C19—H19120.3
C7—C8—H8119.5C18—C19—H19120.3
C2—C8—H8119.5C19—C20—C15121.82 (18)
O2—C9—N1121.89 (15)C19—C20—H20119.1
O2—C9—C10121.78 (14)C15—C20—H20119.1
N1—C9—C10116.33 (15)C9—N1—C1124.00 (13)
C9—C10—H10A109.5C9—N1—H1A118.0
C9—C10—H10B109.5C1—N1—H1A118.0
H10A—C10—H10B109.5C12—O1—H1B109.5
C9—C10—H10C109.5
N1—C1—C2—C3−148.79 (15)C11—C12—C13—C14−1.0 (2)
C11—C1—C2—C3−23.7 (2)C12—C13—C14—C15−0.6 (2)
N1—C1—C2—C834.33 (19)C13—C14—C15—C20−179.08 (16)
C11—C1—C2—C8159.45 (14)C13—C14—C15—C161.2 (2)
C8—C2—C3—C4−0.8 (3)C14—C15—C16—C17−179.63 (15)
C1—C2—C3—C4−177.72 (16)C20—C15—C16—C170.6 (2)
C2—C3—C4—C5−0.1 (3)C14—C15—C16—C11−0.2 (2)
C3—C4—C5—C70.5 (3)C20—C15—C16—C11−179.93 (15)
C3—C4—C5—C6179.83 (18)C12—C11—C16—C17178.05 (14)
C4—C5—C7—C8−0.1 (3)C1—C11—C16—C17−1.4 (2)
C6—C5—C7—C8−179.40 (18)C12—C11—C16—C15−1.3 (2)
C5—C7—C8—C2−0.8 (3)C1—C11—C16—C15179.22 (13)
C3—C2—C8—C71.2 (2)C15—C16—C17—C18−0.6 (2)
C1—C2—C8—C7178.18 (15)C11—C16—C17—C18−179.98 (16)
N1—C1—C11—C1256.06 (17)C16—C17—C18—C190.1 (3)
C2—C1—C11—C12−69.78 (17)C17—C18—C19—C200.2 (3)
N1—C1—C11—C16−124.50 (14)C18—C19—C20—C15−0.2 (3)
C2—C1—C11—C16109.65 (15)C14—C15—C20—C19179.99 (18)
C16—C11—C12—O1179.95 (12)C16—C15—C20—C19−0.3 (3)
C1—C11—C12—O1−0.6 (2)O2—C9—N1—C13.4 (2)
C16—C11—C12—C132.0 (2)C10—C9—N1—C1−175.71 (14)
C1—C11—C12—C13−178.56 (13)C11—C1—N1—C9125.81 (15)
O1—C12—C13—C14−178.92 (14)C2—C1—N1—C9−107.16 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.862.202.7396 (16)121
O1—H1B···O2i0.821.852.6498 (15)165
Symmetry code: (i) −x+3/2, y−1/2, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.862.202.7396 (16)121
O1—H1B···O2i0.821.852.6498 (15)165
Symmetry code: (i) −x+3/2, y−1/2, −z+3/2.
 

References

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ISSN: 2056-9890
Volume 71| Part 4| April 2015| Page o235
doi:10.1107/S2056989015004661
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