organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

1-[(3-Benz­yl­oxy-2-nitro­phen­­oxy)meth­yl]benzene

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bChemistry Department, Manipal Institute of Technology, Manipal, India, cDepartment of Printing, Manipal Institute of Technology, Manipal 576 104, India, and dDepartment of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India
*Correspondence e-mail: hkfun@usm.my

(Received 25 June 2012; accepted 27 June 2012; online 4 July 2012)

The asymmetric unit of the title compound, C20H17NO4, consists of two crystallographically independent mol­ecules. In one of the mol­ecules, the central benzene ring forms dihedral angles of 2.26 (6) and 58.68 (6)° with the terminal benzene rings and the dihedral angle between the terminal benzene rings is 56.45 (6)°. The corresponding values for the other mol­ecule are 35.17 (6), 70.97 (6) and 69.62 (6)°, respectively. In the crystal, an inversion dimer linked by a pair of C—H⋯O hydrogen bonds occurs for one of the unique mol­ecules. C—H⋯π and ππ [centroid–centroid distances = 3.7113 (8) and 3.7216 (7) Å] inter­actions link the components into a three-dimensional network.

Related literature

For background to 1-((3-(benz­yloxy)-2-nitro­phen­oxy)meth­yl)benzene derivatives, see: Altmann et al. (2004[Altmann, E., Cowan-Jacob, S. W. & Martin Missbach, M. (2004). J. Med. Chem. 4, 5833-5836.]); Ohkubo et al. (1997[Ohkubo, M., Kawamoto, H., Ohno, T., Nakano, M. & Morishima, H. (1997). Tetrahedron, 53, 585-592.]). For related structures, see: Naveenkumar et al. (2009[Naveenkumar, H. S., Sadikun, A., Ibrahim, P., Loh, W.-S. & Fun, H.-K. (2009). Acta Cryst. E65, o2540-o2541.]); Fun et al. (2011[Fun, H.-K., Arshad, S., Sarojini, B. K., Khaleel, V. M. & Narayana, B. (2011). Acta Cryst. E67, o1372-o1373.]); Ren & Wang (2012[Ren, D. & Wang, Y. (2012). Acta Cryst. E68, o1049.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C20H17NO4

  • Mr = 335.35

  • Triclinic, [P \overline 1]

  • a = 7.6150 (4) Å

  • b = 14.6248 (7) Å

  • c = 15.2915 (8) Å

  • α = 94.706 (1)°

  • β = 101.627 (1)°

  • γ = 90.572 (1)°

  • V = 1661.80 (15) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100 K

  • 0.26 × 0.19 × 0.09 mm

Data collection
  • Bruker SMART APEXII DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.976, Tmax = 0.992

  • 35546 measured reflections

  • 9716 independent reflections

  • 7508 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.117

  • S = 1.03

  • 9716 reflections

  • 451 parameters

  • H-atom parameters constrained

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg3 and Cg4 are the centroids of the C8A–C13A, C15A–C20A and C8B–C13B rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C17A—H17A⋯O4Bi 0.95 2.49 3.2100 (16) 133
C9A—H9AACg4ii 0.95 2.68 3.5487 (13) 152
C16A—H16ACg2i 0.95 2.68 3.5161 (13) 147
C20B—H20BCg3iii 0.95 2.87 3.7013 (14) 146
Symmetry codes: (i) -x, -y, -z+1; (ii) x-1, y, z; (iii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

1-((3-(Benzyloxy)-2-nitrophenoxy)methyl)benzene derivatives are extensively used in Medicinal Chemistry as important intermediates for many pharmaceutical products (Altmann et al., 2004). 3-(Benzyloxy)-2-nitrophenol is used as intermediate for the synthesis of anticancer products and many natural products as well (Ohkubo et al., 1997). As part of our studies in this area, we hereby report the crystal structure of the title compound.

The asymmetric unit of the title compound (Fig. 1), consists of two crystallographically independent molecules, A and B. Bond lengths and angles are within normal ranges (Naveenkumar et al., 2009; Fun et al., 2011; Ren & Wang, 2012). In molecule A, the central benzene ring (C8A–C13A) forms dihedral angles of 2.26 (6) and 58.68 (6)°, respectively, with the terminal benzene rings (C1A–C6A & C15A–C20A). The dihedral angle between the terminal benzene rings is 56.45 (6)°. The corresponding values in molecule B are 35.17 (6), 70.97 (6) and 69.62 (6)°, respectively.

The crystal structure is shown in Fig. 2. The molecules are linked together with another neighbouring molecules via C17A—H17A···O4B hydrogen bonds (Table 1) to form inversion dimers. C—H···π interactions (Table 1) and ππ interactions of Cg1···Cg1 = 3.7113 (8) Å (symmetry code: 1 - x, 1 - y, 1 - z) and Cg1···Cg2 = 3.7216 (7) Å (symmetry code: -x, 1 - y, 1 - z) link the molecules into a three-dimensional network. [Cg1, Cg2, Cg3 and Cg4 are the centroids of the C1A–C6A, C8A–C13A, C15A–C20A and C8B–C13B rings, respectively].

Related literature top

For background to 1-((3-(benzyloxy)-2-nitrophenoxy)methyl)benzene derivatives, see: Altmann et al. (2004); Ohkubo et al. (1997). For related structures, see: Naveenkumar et al. (2009); Fun et al. (2011); Ren & Wang (2012). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

To a stirred solution of 3-(benzyloxy)-2-nitrophenol (1 g, 0.006 mol) in acetonitrile (20 ml) was added potassium carbonate (0.89 g, 0.006 mol) benzyl bromide (1.1 g, 0.006 mol) drop-wise at 273 K. The reaction mixture was stirred at room temperature for 2 h. Mass analysis of crude reaction mixture confirms the completion of the reaction. The reaction mixture was concentrated and the residue was purified by column chromatography to get title compound, which was recrystallized using acetone to get orange plates. Yield: 55%, M.p. 351–353 K.

Refinement top

All the H atoms were positioned geometrically [C–H = 0.95 or 0.99 Å] and refined using a riding model with Uiso(H) = 1.2 Ueq(C). Three outliers were omitted (-1 1 0, -4 2 0 and 2 - 6 9) in the final refinement.

Structure description top

1-((3-(Benzyloxy)-2-nitrophenoxy)methyl)benzene derivatives are extensively used in Medicinal Chemistry as important intermediates for many pharmaceutical products (Altmann et al., 2004). 3-(Benzyloxy)-2-nitrophenol is used as intermediate for the synthesis of anticancer products and many natural products as well (Ohkubo et al., 1997). As part of our studies in this area, we hereby report the crystal structure of the title compound.

The asymmetric unit of the title compound (Fig. 1), consists of two crystallographically independent molecules, A and B. Bond lengths and angles are within normal ranges (Naveenkumar et al., 2009; Fun et al., 2011; Ren & Wang, 2012). In molecule A, the central benzene ring (C8A–C13A) forms dihedral angles of 2.26 (6) and 58.68 (6)°, respectively, with the terminal benzene rings (C1A–C6A & C15A–C20A). The dihedral angle between the terminal benzene rings is 56.45 (6)°. The corresponding values in molecule B are 35.17 (6), 70.97 (6) and 69.62 (6)°, respectively.

The crystal structure is shown in Fig. 2. The molecules are linked together with another neighbouring molecules via C17A—H17A···O4B hydrogen bonds (Table 1) to form inversion dimers. C—H···π interactions (Table 1) and ππ interactions of Cg1···Cg1 = 3.7113 (8) Å (symmetry code: 1 - x, 1 - y, 1 - z) and Cg1···Cg2 = 3.7216 (7) Å (symmetry code: -x, 1 - y, 1 - z) link the molecules into a three-dimensional network. [Cg1, Cg2, Cg3 and Cg4 are the centroids of the C1A–C6A, C8A–C13A, C15A–C20A and C8B–C13B rings, respectively].

For background to 1-((3-(benzyloxy)-2-nitrophenoxy)methyl)benzene derivatives, see: Altmann et al. (2004); Ohkubo et al. (1997). For related structures, see: Naveenkumar et al. (2009); Fun et al. (2011); Ren & Wang (2012). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing of the title compound, showing the formation of the inversion dimers. For the sake of clarity, those H atoms not involved in the intermolecular interactions (dashed lines) have been omitted.
1-[(3-Benzyloxy-2-nitrophenoxy)methyl]benzene top
Crystal data top
C20H17NO4Z = 4
Mr = 335.35F(000) = 704
Triclinic, P1Dx = 1.340 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.6150 (4) ÅCell parameters from 9997 reflections
b = 14.6248 (7) Åθ = 2.7–30.1°
c = 15.2915 (8) ŵ = 0.09 mm1
α = 94.706 (1)°T = 100 K
β = 101.627 (1)°Plate, orange
γ = 90.572 (1)°0.26 × 0.19 × 0.09 mm
V = 1661.80 (15) Å3
Data collection top
Bruker SMART APEXII DUO CCD
diffractometer
9716 independent reflections
Radiation source: fine-focus sealed tube7508 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 30.1°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1010
Tmin = 0.976, Tmax = 0.992k = 2020
35546 measured reflectionsl = 2121
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.054P)2 + 0.4706P]
where P = (Fo2 + 2Fc2)/3
9716 reflections(Δ/σ)max < 0.001
451 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C20H17NO4γ = 90.572 (1)°
Mr = 335.35V = 1661.80 (15) Å3
Triclinic, P1Z = 4
a = 7.6150 (4) ÅMo Kα radiation
b = 14.6248 (7) ŵ = 0.09 mm1
c = 15.2915 (8) ÅT = 100 K
α = 94.706 (1)°0.26 × 0.19 × 0.09 mm
β = 101.627 (1)°
Data collection top
Bruker SMART APEXII DUO CCD
diffractometer
9716 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
7508 reflections with I > 2σ(I)
Tmin = 0.976, Tmax = 0.992Rint = 0.032
35546 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.03Δρmax = 0.38 e Å3
9716 reflectionsΔρmin = 0.29 e Å3
451 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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) top
xyzUiso*/Ueq
O1A0.13559 (11)0.36930 (5)0.49220 (6)0.02214 (17)
O2A0.10558 (10)0.09202 (5)0.55126 (5)0.02063 (17)
O3A0.25107 (14)0.20447 (9)0.62840 (7)0.0468 (3)
O4A0.04238 (16)0.28956 (9)0.65945 (7)0.0513 (3)
N1A0.10941 (13)0.24213 (7)0.60732 (7)0.0215 (2)
C1A0.32496 (16)0.52370 (8)0.57710 (9)0.0262 (2)
H1AA0.30240.47410.61010.031*
C2A0.42369 (17)0.60071 (9)0.62090 (11)0.0336 (3)
H2AA0.46730.60390.68380.040*
C3A0.45841 (18)0.67279 (9)0.57274 (12)0.0381 (4)
H3AA0.52580.72530.60280.046*
C4A0.39539 (19)0.66844 (9)0.48159 (12)0.0374 (3)
H4AA0.42040.71760.44870.045*
C5A0.29527 (17)0.59230 (8)0.43760 (10)0.0302 (3)
H5AA0.25090.58980.37470.036*
C6A0.25959 (15)0.51938 (8)0.48546 (9)0.0230 (2)
C7A0.14950 (15)0.43950 (8)0.43354 (8)0.0218 (2)
H7AA0.02830.45990.40700.026*
H7AB0.20680.41480.38420.026*
C8A0.03602 (14)0.29318 (7)0.45495 (8)0.0185 (2)
C9A0.04526 (15)0.27616 (8)0.36507 (8)0.0201 (2)
H9AA0.03340.31950.32350.024*
C10A0.14422 (15)0.19488 (8)0.33674 (8)0.0206 (2)
H10A0.19830.18320.27510.025*
C11A0.16659 (15)0.13023 (8)0.39534 (8)0.0196 (2)
H11A0.23450.07520.37410.024*
C12A0.08803 (14)0.14722 (7)0.48569 (7)0.0176 (2)
C13A0.01607 (14)0.22707 (7)0.51330 (7)0.0176 (2)
C14A0.24977 (15)0.02361 (8)0.52786 (8)0.0198 (2)
H14A0.20900.03190.49690.024*
H14B0.35300.04800.48700.024*
C15A0.30454 (14)0.00015 (7)0.61225 (8)0.0179 (2)
C16A0.29037 (15)0.08909 (8)0.63851 (8)0.0207 (2)
H16A0.23800.13480.60490.025*
C17A0.35264 (16)0.11121 (9)0.71380 (9)0.0260 (3)
H17A0.34340.17210.73130.031*
C18A0.42811 (17)0.04469 (10)0.76329 (9)0.0297 (3)
H18A0.47090.06000.81460.036*
C19A0.44114 (19)0.04415 (10)0.73792 (9)0.0322 (3)
H19A0.49200.09000.77220.039*
C20A0.38016 (17)0.06621 (8)0.66276 (9)0.0257 (2)
H20A0.39000.12720.64550.031*
O1B0.61240 (11)0.48372 (5)0.17237 (6)0.02478 (18)
O2B0.81078 (10)0.19193 (5)0.10404 (6)0.02094 (17)
O3B0.44330 (11)0.33094 (6)0.04889 (6)0.0286 (2)
O4B0.49167 (11)0.25710 (6)0.16793 (6)0.02714 (19)
N1B0.54058 (12)0.30732 (6)0.11650 (7)0.01836 (18)
C1B0.31381 (17)0.57666 (8)0.08217 (8)0.0234 (2)
H1BA0.34440.52450.04770.028*
C2B0.14345 (17)0.61162 (8)0.06114 (8)0.0257 (2)
H2BA0.05770.58290.01260.031*
C3B0.09729 (18)0.68790 (9)0.11025 (10)0.0316 (3)
H3BA0.01920.71210.09510.038*
C4B0.2218 (2)0.72864 (10)0.18152 (11)0.0401 (4)
H4BA0.19050.78090.21570.048*
C5B0.39273 (19)0.69359 (9)0.20353 (10)0.0342 (3)
H5BA0.47740.72170.25290.041*
C6B0.44001 (16)0.61761 (8)0.15347 (8)0.0223 (2)
C7B0.62756 (17)0.58239 (8)0.17359 (9)0.0262 (2)
H7BA0.69450.59950.12790.031*
H7BB0.69230.60900.23310.031*
C8B0.76005 (15)0.43423 (8)0.16589 (8)0.0209 (2)
C9B0.93703 (16)0.46798 (8)0.18596 (8)0.0243 (2)
H9BA0.96390.53060.20650.029*
C10B1.07298 (16)0.40807 (8)0.17527 (8)0.0249 (2)
H10B1.19320.43130.18770.030*
C11B1.04041 (15)0.31547 (8)0.14720 (8)0.0224 (2)
H11B1.13650.27650.14010.027*
C12B0.86381 (14)0.28059 (7)0.12962 (7)0.0186 (2)
C13B0.72783 (14)0.34141 (7)0.13854 (7)0.0180 (2)
C14B0.94773 (16)0.12652 (8)0.09238 (10)0.0267 (3)
H14C1.05390.13730.14170.032*
H14D0.98560.13300.03490.032*
C15B0.86818 (15)0.03228 (8)0.09284 (8)0.0223 (2)
C16B0.74639 (17)0.00707 (9)0.01872 (9)0.0271 (3)
H16B0.71520.02530.03340.033*
C17B0.67035 (18)0.09329 (9)0.02052 (10)0.0307 (3)
H17B0.58680.11960.03020.037*
C18B0.71567 (17)0.14099 (9)0.09577 (10)0.0293 (3)
H18B0.66270.19990.09690.035*
C19B0.83853 (18)0.10289 (9)0.16962 (10)0.0313 (3)
H19B0.87110.13600.22110.038*
C20B0.91417 (17)0.01623 (9)0.16831 (9)0.0281 (3)
H20B0.99760.01000.21920.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0237 (4)0.0180 (4)0.0246 (4)0.0058 (3)0.0041 (3)0.0039 (3)
O2A0.0195 (4)0.0217 (4)0.0198 (4)0.0067 (3)0.0004 (3)0.0063 (3)
O3A0.0319 (5)0.0672 (8)0.0343 (6)0.0153 (5)0.0084 (4)0.0002 (5)
O4A0.0507 (7)0.0733 (8)0.0250 (5)0.0227 (6)0.0016 (5)0.0121 (5)
N1A0.0211 (4)0.0216 (5)0.0209 (5)0.0061 (4)0.0016 (4)0.0036 (4)
C1A0.0207 (5)0.0216 (5)0.0378 (7)0.0006 (4)0.0106 (5)0.0007 (5)
C2A0.0237 (6)0.0299 (6)0.0467 (8)0.0024 (5)0.0119 (6)0.0109 (6)
C3A0.0257 (6)0.0200 (6)0.0697 (11)0.0039 (5)0.0176 (7)0.0096 (6)
C4A0.0325 (7)0.0162 (5)0.0684 (11)0.0007 (5)0.0208 (7)0.0072 (6)
C5A0.0267 (6)0.0190 (5)0.0483 (8)0.0026 (5)0.0132 (6)0.0085 (5)
C6A0.0170 (5)0.0161 (5)0.0382 (7)0.0015 (4)0.0109 (5)0.0028 (4)
C7A0.0193 (5)0.0189 (5)0.0287 (6)0.0008 (4)0.0065 (4)0.0072 (4)
C8A0.0157 (5)0.0167 (5)0.0239 (6)0.0002 (4)0.0053 (4)0.0021 (4)
C9A0.0206 (5)0.0196 (5)0.0213 (5)0.0012 (4)0.0061 (4)0.0056 (4)
C10A0.0208 (5)0.0229 (5)0.0182 (5)0.0017 (4)0.0035 (4)0.0033 (4)
C11A0.0193 (5)0.0185 (5)0.0204 (5)0.0015 (4)0.0024 (4)0.0019 (4)
C12A0.0163 (5)0.0174 (5)0.0199 (5)0.0005 (4)0.0044 (4)0.0044 (4)
C13A0.0159 (4)0.0188 (5)0.0178 (5)0.0004 (4)0.0025 (4)0.0023 (4)
C14A0.0186 (5)0.0180 (5)0.0223 (6)0.0049 (4)0.0030 (4)0.0025 (4)
C15A0.0155 (4)0.0173 (5)0.0203 (5)0.0031 (4)0.0021 (4)0.0018 (4)
C16A0.0180 (5)0.0184 (5)0.0251 (6)0.0013 (4)0.0027 (4)0.0025 (4)
C17A0.0229 (5)0.0266 (6)0.0273 (6)0.0076 (4)0.0003 (5)0.0097 (5)
C18A0.0273 (6)0.0413 (7)0.0209 (6)0.0120 (5)0.0058 (5)0.0036 (5)
C19A0.0345 (7)0.0337 (7)0.0304 (7)0.0027 (5)0.0145 (5)0.0059 (5)
C20A0.0293 (6)0.0188 (5)0.0298 (6)0.0011 (4)0.0082 (5)0.0008 (4)
O1B0.0241 (4)0.0144 (4)0.0377 (5)0.0001 (3)0.0098 (4)0.0045 (3)
O2B0.0170 (4)0.0180 (4)0.0286 (4)0.0028 (3)0.0059 (3)0.0027 (3)
O3B0.0220 (4)0.0330 (5)0.0293 (5)0.0011 (3)0.0010 (3)0.0101 (4)
O4B0.0240 (4)0.0280 (4)0.0327 (5)0.0033 (3)0.0100 (4)0.0121 (4)
N1B0.0172 (4)0.0153 (4)0.0236 (5)0.0010 (3)0.0062 (3)0.0026 (3)
C1B0.0317 (6)0.0186 (5)0.0208 (6)0.0006 (4)0.0069 (5)0.0024 (4)
C2B0.0302 (6)0.0223 (5)0.0242 (6)0.0025 (5)0.0032 (5)0.0063 (4)
C3B0.0268 (6)0.0237 (6)0.0455 (8)0.0018 (5)0.0089 (6)0.0051 (5)
C4B0.0364 (7)0.0284 (7)0.0531 (9)0.0049 (6)0.0095 (7)0.0129 (6)
C5B0.0332 (7)0.0261 (6)0.0390 (8)0.0007 (5)0.0024 (6)0.0099 (5)
C6B0.0272 (6)0.0154 (5)0.0252 (6)0.0016 (4)0.0070 (5)0.0038 (4)
C7B0.0276 (6)0.0145 (5)0.0357 (7)0.0020 (4)0.0043 (5)0.0027 (4)
C8B0.0221 (5)0.0187 (5)0.0231 (6)0.0005 (4)0.0054 (4)0.0063 (4)
C9B0.0244 (5)0.0203 (5)0.0280 (6)0.0048 (4)0.0033 (5)0.0065 (4)
C10B0.0194 (5)0.0277 (6)0.0276 (6)0.0053 (4)0.0018 (4)0.0112 (5)
C11B0.0174 (5)0.0263 (6)0.0249 (6)0.0008 (4)0.0046 (4)0.0100 (4)
C12B0.0187 (5)0.0193 (5)0.0190 (5)0.0003 (4)0.0047 (4)0.0059 (4)
C13B0.0162 (5)0.0184 (5)0.0204 (5)0.0018 (4)0.0044 (4)0.0058 (4)
C14B0.0192 (5)0.0222 (6)0.0406 (7)0.0054 (4)0.0100 (5)0.0032 (5)
C15B0.0185 (5)0.0201 (5)0.0298 (6)0.0059 (4)0.0081 (4)0.0021 (4)
C16B0.0288 (6)0.0263 (6)0.0265 (6)0.0057 (5)0.0054 (5)0.0033 (5)
C17B0.0301 (6)0.0269 (6)0.0334 (7)0.0011 (5)0.0051 (5)0.0040 (5)
C18B0.0290 (6)0.0212 (6)0.0405 (8)0.0032 (5)0.0140 (5)0.0015 (5)
C19B0.0330 (7)0.0300 (6)0.0337 (7)0.0066 (5)0.0095 (5)0.0115 (5)
C20B0.0245 (6)0.0295 (6)0.0293 (7)0.0037 (5)0.0027 (5)0.0039 (5)
Geometric parameters (Å, º) top
O1A—C8A1.3579 (13)O1B—C8B1.3591 (14)
O1A—C7A1.4343 (13)O1B—C7B1.4448 (13)
O2A—C12A1.3636 (13)O2B—C12B1.3565 (13)
O2A—C14A1.4476 (13)O2B—C14B1.4495 (13)
O3A—N1A1.2131 (14)O3B—N1B1.2214 (12)
O4A—N1A1.2073 (14)O4B—N1B1.2263 (12)
N1A—C13A1.4675 (14)N1B—C13B1.4697 (14)
C1A—C6A1.3854 (19)C1B—C2B1.3856 (17)
C1A—C2A1.3924 (18)C1B—C6B1.3892 (17)
C1A—H1AA0.9500C1B—H1BA0.9500
C2A—C3A1.387 (2)C2B—C3B1.3815 (18)
C2A—H2AA0.9500C2B—H2BA0.9500
C3A—C4A1.376 (2)C3B—C4B1.381 (2)
C3A—H3AA0.9500C3B—H3BA0.9500
C4A—C5A1.388 (2)C4B—C5B1.391 (2)
C4A—H4AA0.9500C4B—H4BA0.9500
C5A—C6A1.3961 (17)C5B—C6B1.3892 (17)
C5A—H5AA0.9500C5B—H5BA0.9500
C6A—C7A1.5026 (16)C6B—C7B1.5045 (17)
C7A—H7AA0.9900C7B—H7BA0.9900
C7A—H7AB0.9900C7B—H7BB0.9900
C8A—C9A1.3899 (16)C8B—C13B1.3916 (15)
C8A—C13A1.3954 (15)C8B—C9B1.3962 (16)
C9A—C10A1.3909 (16)C9B—C10B1.3889 (17)
C9A—H9AA0.9500C9B—H9BA0.9500
C10A—C11A1.3868 (15)C10B—C11B1.3909 (17)
C10A—H10A0.9500C10B—H10B0.9500
C11A—C12A1.3914 (16)C11B—C12B1.3997 (15)
C11A—H11A0.9500C11B—H11B0.9500
C12A—C13A1.3915 (15)C12B—C13B1.3919 (15)
C14A—C15A1.4992 (16)C14B—C15B1.5010 (17)
C14A—H14A0.9900C14B—H14C0.9900
C14A—H14B0.9900C14B—H14D0.9900
C15A—C16A1.3914 (15)C15B—C20B1.3907 (17)
C15A—C20A1.3919 (16)C15B—C16B1.3910 (18)
C16A—C17A1.3903 (17)C16B—C17B1.3869 (18)
C16A—H16A0.9500C16B—H16B0.9500
C17A—C18A1.3838 (19)C17B—C18B1.381 (2)
C17A—H17A0.9500C17B—H17B0.9500
C18A—C19A1.385 (2)C18B—C19B1.386 (2)
C18A—H18A0.9500C18B—H18B0.9500
C19A—C20A1.3833 (19)C19B—C20B1.3903 (19)
C19A—H19A0.9500C19B—H19B0.9500
C20A—H20A0.9500C20B—H20B0.9500
C8A—O1A—C7A116.28 (9)C8B—O1B—C7B117.97 (9)
C12A—O2A—C14A115.70 (8)C12B—O2B—C14B117.79 (9)
O4A—N1A—O3A123.50 (11)O3B—N1B—O4B124.10 (10)
O4A—N1A—C13A119.39 (10)O3B—N1B—C13B118.39 (9)
O3A—N1A—C13A117.10 (10)O4B—N1B—C13B117.50 (9)
C6A—C1A—C2A120.03 (12)C2B—C1B—C6B120.28 (11)
C6A—C1A—H1AA120.0C2B—C1B—H1BA119.9
C2A—C1A—H1AA120.0C6B—C1B—H1BA119.9
C3A—C2A—C1A120.08 (14)C3B—C2B—C1B120.54 (12)
C3A—C2A—H2AA120.0C3B—C2B—H2BA119.7
C1A—C2A—H2AA120.0C1B—C2B—H2BA119.7
C4A—C3A—C2A120.12 (13)C4B—C3B—C2B119.47 (12)
C4A—C3A—H3AA119.9C4B—C3B—H3BA120.3
C2A—C3A—H3AA119.9C2B—C3B—H3BA120.3
C3A—C4A—C5A120.13 (13)C3B—C4B—C5B120.38 (13)
C3A—C4A—H4AA119.9C3B—C4B—H4BA119.8
C5A—C4A—H4AA119.9C5B—C4B—H4BA119.8
C4A—C5A—C6A120.20 (14)C6B—C5B—C4B120.19 (13)
C4A—C5A—H5AA119.9C6B—C5B—H5BA119.9
C6A—C5A—H5AA119.9C4B—C5B—H5BA119.9
C1A—C6A—C5A119.44 (12)C5B—C6B—C1B119.13 (11)
C1A—C6A—C7A123.28 (11)C5B—C6B—C7B120.56 (11)
C5A—C6A—C7A117.28 (12)C1B—C6B—C7B120.26 (11)
O1A—C7A—C6A109.51 (10)O1B—C7B—C6B107.15 (9)
O1A—C7A—H7AA109.8O1B—C7B—H7BA110.3
C6A—C7A—H7AA109.8C6B—C7B—H7BA110.3
O1A—C7A—H7AB109.8O1B—C7B—H7BB110.3
C6A—C7A—H7AB109.8C6B—C7B—H7BB110.3
H7AA—C7A—H7AB108.2H7BA—C7B—H7BB108.5
O1A—C8A—C9A125.74 (10)O1B—C8B—C13B115.54 (10)
O1A—C8A—C13A115.96 (10)O1B—C8B—C9B125.85 (11)
C9A—C8A—C13A118.30 (10)C13B—C8B—C9B118.59 (10)
C8A—C9A—C10A119.19 (10)C10B—C9B—C8B118.60 (11)
C8A—C9A—H9AA120.4C10B—C9B—H9BA120.7
C10A—C9A—H9AA120.4C8B—C9B—H9BA120.7
C11A—C10A—C9A122.27 (11)C9B—C10B—C11B122.72 (11)
C11A—C10A—H10A118.9C9B—C10B—H10B118.6
C9A—C10A—H10A118.9C11B—C10B—H10B118.6
C10A—C11A—C12A119.00 (10)C10B—C11B—C12B118.96 (11)
C10A—C11A—H11A120.5C10B—C11B—H11B120.5
C12A—C11A—H11A120.5C12B—C11B—H11B120.5
O2A—C12A—C11A125.33 (10)O2B—C12B—C13B115.94 (9)
O2A—C12A—C13A116.09 (10)O2B—C12B—C11B126.05 (10)
C11A—C12A—C13A118.58 (10)C13B—C12B—C11B118.01 (10)
C12A—C13A—C8A122.56 (10)C8B—C13B—C12B123.08 (10)
C12A—C13A—N1A118.74 (9)C8B—C13B—N1B117.85 (9)
C8A—C13A—N1A118.70 (9)C12B—C13B—N1B119.06 (10)
O2A—C14A—C15A108.45 (9)O2B—C14B—C15B107.41 (9)
O2A—C14A—H14A110.0O2B—C14B—H14C110.2
C15A—C14A—H14A110.0C15B—C14B—H14C110.2
O2A—C14A—H14B110.0O2B—C14B—H14D110.2
C15A—C14A—H14B110.0C15B—C14B—H14D110.2
H14A—C14A—H14B108.4H14C—C14B—H14D108.5
C16A—C15A—C20A119.12 (11)C20B—C15B—C16B119.24 (11)
C16A—C15A—C14A121.02 (10)C20B—C15B—C14B120.06 (11)
C20A—C15A—C14A119.76 (10)C16B—C15B—C14B120.69 (11)
C17A—C16A—C15A120.20 (11)C17B—C16B—C15B120.30 (12)
C17A—C16A—H16A119.9C17B—C16B—H16B119.8
C15A—C16A—H16A119.9C15B—C16B—H16B119.8
C18A—C17A—C16A120.13 (11)C18B—C17B—C16B120.26 (13)
C18A—C17A—H17A119.9C18B—C17B—H17B119.9
C16A—C17A—H17A119.9C16B—C17B—H17B119.9
C17A—C18A—C19A119.93 (12)C17B—C18B—C19B119.92 (12)
C17A—C18A—H18A120.0C17B—C18B—H18B120.0
C19A—C18A—H18A120.0C19B—C18B—H18B120.0
C20A—C19A—C18A120.04 (12)C18B—C19B—C20B120.00 (12)
C20A—C19A—H19A120.0C18B—C19B—H19B120.0
C18A—C19A—H19A120.0C20B—C19B—H19B120.0
C19A—C20A—C15A120.57 (11)C19B—C20B—C15B120.27 (12)
C19A—C20A—H20A119.7C19B—C20B—H20B119.9
C15A—C20A—H20A119.7C15B—C20B—H20B119.9
C6A—C1A—C2A—C3A0.70 (18)C6B—C1B—C2B—C3B0.48 (18)
C1A—C2A—C3A—C4A0.03 (19)C1B—C2B—C3B—C4B0.8 (2)
C2A—C3A—C4A—C5A0.6 (2)C2B—C3B—C4B—C5B0.4 (2)
C3A—C4A—C5A—C6A0.65 (19)C3B—C4B—C5B—C6B0.5 (2)
C2A—C1A—C6A—C5A0.69 (17)C4B—C5B—C6B—C1B0.8 (2)
C2A—C1A—C6A—C7A178.96 (11)C4B—C5B—C6B—C7B176.62 (13)
C4A—C5A—C6A—C1A0.02 (18)C2B—C1B—C6B—C5B0.36 (18)
C4A—C5A—C6A—C7A179.65 (11)C2B—C1B—C6B—C7B177.11 (11)
C8A—O1A—C7A—C6A178.60 (9)C8B—O1B—C7B—C6B163.48 (10)
C1A—C6A—C7A—O1A3.76 (15)C5B—C6B—C7B—O1B135.13 (12)
C5A—C6A—C7A—O1A176.59 (9)C1B—C6B—C7B—O1B47.45 (15)
C7A—O1A—C8A—C9A3.17 (15)C7B—O1B—C8B—C13B161.68 (10)
C7A—O1A—C8A—C13A177.09 (9)C7B—O1B—C8B—C9B19.83 (18)
O1A—C8A—C9A—C10A179.70 (10)O1B—C8B—C9B—C10B179.71 (11)
C13A—C8A—C9A—C10A0.56 (16)C13B—C8B—C9B—C10B1.85 (17)
C8A—C9A—C10A—C11A0.73 (17)C8B—C9B—C10B—C11B1.37 (19)
C9A—C10A—C11A—C12A0.23 (17)C9B—C10B—C11B—C12B0.57 (18)
C14A—O2A—C12A—C11A15.49 (15)C14B—O2B—C12B—C13B178.94 (10)
C14A—O2A—C12A—C13A163.81 (9)C14B—O2B—C12B—C11B0.86 (16)
C10A—C11A—C12A—O2A176.84 (10)C10B—C11B—C12B—O2B178.27 (11)
C10A—C11A—C12A—C13A2.44 (16)C10B—C11B—C12B—C13B1.93 (17)
O2A—C12A—C13A—C8A175.50 (9)O1B—C8B—C13B—C12B179.07 (10)
C11A—C12A—C13A—C8A3.85 (16)C9B—C8B—C13B—C12B0.46 (17)
O2A—C12A—C13A—N1A4.89 (14)O1B—C8B—C13B—N1B2.22 (15)
C11A—C12A—C13A—N1A175.76 (10)C9B—C8B—C13B—N1B179.17 (10)
O1A—C8A—C13A—C12A177.34 (10)O2B—C12B—C13B—C8B178.73 (10)
C9A—C8A—C13A—C12A2.89 (16)C11B—C12B—C13B—C8B1.46 (17)
O1A—C8A—C13A—N1A3.04 (14)O2B—C12B—C13B—N1B2.58 (15)
C9A—C8A—C13A—N1A176.72 (10)C11B—C12B—C13B—N1B177.24 (10)
O4A—N1A—C13A—C12A97.23 (14)O3B—N1B—C13B—C8B69.71 (14)
O3A—N1A—C13A—C12A81.92 (14)O4B—N1B—C13B—C8B109.84 (12)
O4A—N1A—C13A—C8A83.14 (14)O3B—N1B—C13B—C12B109.06 (12)
O3A—N1A—C13A—C8A97.71 (13)O4B—N1B—C13B—C12B71.39 (14)
C12A—O2A—C14A—C15A154.61 (9)C12B—O2B—C14B—C15B162.67 (10)
O2A—C14A—C15A—C16A118.80 (11)O2B—C14B—C15B—C20B103.79 (12)
O2A—C14A—C15A—C20A64.84 (13)O2B—C14B—C15B—C16B75.37 (14)
C20A—C15A—C16A—C17A0.58 (17)C20B—C15B—C16B—C17B0.69 (18)
C14A—C15A—C16A—C17A175.80 (10)C14B—C15B—C16B—C17B178.48 (11)
C15A—C16A—C17A—C18A0.37 (17)C15B—C16B—C17B—C18B0.35 (19)
C16A—C17A—C18A—C19A0.19 (19)C16B—C17B—C18B—C19B0.43 (19)
C17A—C18A—C19A—C20A0.5 (2)C17B—C18B—C19B—C20B0.85 (19)
C18A—C19A—C20A—C15A0.3 (2)C18B—C19B—C20B—C15B0.50 (19)
C16A—C15A—C20A—C19A0.23 (18)C16B—C15B—C20B—C19B0.27 (18)
C14A—C15A—C20A—C19A176.19 (11)C14B—C15B—C20B—C19B178.91 (11)
Hydrogen-bond geometry (Å, º) top
Cg2 , Cg3 and Cg4 are the centroids of the C8A–C13A, C15A–C20A and C8B–C13B rings, respectively.
D—H···AD—HH···AD···AD—H···A
C17A—H17A···O4Bi0.952.493.2100 (16)133
C9A—H9AA···Cg4ii0.952.683.5487 (13)152
C16A—H16A···Cg2i0.952.683.5161 (13)147
C20B—H20B···Cg3iii0.952.873.7013 (14)146
Symmetry codes: (i) x, y, z+1; (ii) x1, y, z; (iii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC20H17NO4
Mr335.35
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.6150 (4), 14.6248 (7), 15.2915 (8)
α, β, γ (°)94.706 (1), 101.627 (1), 90.572 (1)
V3)1661.80 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.26 × 0.19 × 0.09
Data collection
DiffractometerBruker SMART APEXII DUO CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.976, 0.992
No. of measured, independent and
observed [I > 2σ(I)] reflections
35546, 9716, 7508
Rint0.032
(sin θ/λ)max1)0.706
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.117, 1.03
No. of reflections9716
No. of parameters451
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.29

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg2 , Cg3 and Cg4 are the centroids of the C8A–C13A, C15A–C20A and C8B–C13B rings, respectively.
D—H···AD—HH···AD···AD—H···A
C17A—H17A···O4Bi0.952.493.2100 (16)133
C9A—H9AA···Cg4ii0.952.683.5487 (13)152
C16A—H16A···Cg2i0.952.683.5161 (13)147
C20B—H20B···Cg3iii0.952.873.7013 (14)146
Symmetry codes: (i) x, y, z+1; (ii) x1, y, z; (iii) x+1, y, z+1.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and SA thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). SA also thanks the Malaysian Government and USM for the Academic Staff Training Scheme (ASTS) award. AMI thanks the Board of Research in Nuclear Sciences, Government of India, for a 'Young Scientist' award.

References

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