[3-(5-Nitro-2-fur­yl)-1-phenyl-1H-pyrazol-4-yl](phen­yl)methanone

Goh, J.H.; Fun, H.-K.; Nithinchandra; Kalluraya, B.; Rai, N.S.

doi:10.1107/S1600536810015199

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Pages o1229-o1230

https://doi.org/10.1107/S1600536810015199

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[3-(5-Nitro-2-furyl)-1-phenyl-1H-pyrazol-4-yl](phenyl)methanone

Jia Hao Goh,^a ‡ Hoong-Kun Fun,^a ^*§ Nithinchandra,^b B. Kalluraya ^b and N. Satheesh Rai ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 30 March 2010; accepted 26 April 2010; online 30 April 2010)

In the title pyrazole compound, C₂₀H₁₃N₃O₄, an intramolecular C—H⋯O hydrogen bond generates a seven-membered ring, producing an S(7) ring motif. The essentially planar furan and pyrazole rings [maximum deviations of 0.002 (1) and 0.007 (1) Å, respectively] are coplanar with each other, forming a dihedral angle of 3.06 (10)°. The pyrazole ring forms dihedral angles of 8.51 (9) and 56.81 (9)° with the two benzene rings. The nitro group is coplanar with the attached furan ring, as indicated by the dihedral angle of 2.5 (3)°. In the crystal packing, intermolecular C—H⋯O hydrogen bonds link adjacent molecules into two-molecule-wide chains along the a axis. The crystal packing is further stabilized by weak intermolecular C—H⋯π and π–π interactions [centroid–centroid distance = 3.4441 (10) Å].

Related literature

For general background to and applications of the title compound, see: Kalluraya et al. (1994 ); Rai & Kalluraya (2006 ); Rai et al. (2008 ); Sridhar & Perumal (2003 ). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995 ). For closely related structures, see: Goh et al. (2009a ,b ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₀H₁₃N₃O₄
M_r = 359.33
Monoclinic, P 2₁ /c
a = 11.2946 (12) Å
b = 6.9755 (8) Å
c = 22.7064 (18) Å
β = 115.015 (4)°
V = 1621.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.24 × 0.15 × 0.07 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.976, T_max = 0.992
17931 measured reflections
4725 independent reflections
2991 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.129
S = 1.02
4725 reflections
296 parameters
All H-atom parameters refined
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C15–C20 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O4ⁱ	0.98 (2)	2.45 (2)	3.190 (3)	131.8 (17)
C11—H11A⋯O2	0.98 (3)	2.23 (3)	2.950 (3)	130 (2)
C14—H14A⋯O3ⁱⁱ	0.96 (2)	2.43 (2)	3.379 (3)	169.3 (17)
C18—H18A⋯Cg1ⁱⁱⁱ	0.96 (2)	2.96 (2)	3.671 (2)	132.0 (16)
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) x-1, y, z; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{5\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810015199/tk2653sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015199/tk2653Isup2.hkl

checkCIF report

Comment top

Pyrazole derivatives are in general well-known nitrogen-containing heterocyclic compounds and various procedures have been developed for their synthesis (Rai & Kalluraya, 2006). The chemistry of pyrazole derivatives has been the subject of much interest due to their importance for various applications, and their widespread potential and proven biological and pharmacological activities (Rai et al., 2008). Steroids containing pyrazole moiety are of interest as psychopharmacological agents. Some alkyl- and aryl- substituted pyrazoles have sharply pronounced sedative action on the central nervous system. Certain alkyl pyrazoles show significant bacteriostatic, bacteriocidal, fungicidal, analgesic and anti-pyretic activities (Sridhar & Perumal, 2003). In continuation of our studies on 1,3-dipolar cyclo-addition reactions of sydnones with dipolarophiles carrying a nitrofuran or a nitrothiophene moiety (Kalluraya et al., 1994), we herein report the crystal structure of the title pyrazole compound.

In the title compound, Fig. 1, an intramolecular C11—H11A···O2 hydrogen bond (Table 1) generates a seven-membered ring, producing an S(7) ring motif (Bernstein et al., 1995). The furan (C10-C13/O1) and pyrazole (C8/C9/N2/N1/C14) rings are essentially planar, with maximum deviations of 0.002 (1) and -0.007 (1) Å, respectively, at atoms C12 and N2. These two rings are coplanar to one another, as indicated by the dihedral angle formed between them of 3.06 (10)°. The pyrazole ring is inclined at dihedral angles of 56.81 (9) and 8.51 (9)°, respectively, with the C1-C6 and C15-C20 benzene rings. The nitro group is coplanar with the attached furan ring, making a dihedral angle of 2.5 (3)°. The bond lengths and angles agree well with those closely related pyrazole structures (Goh et al., 2009a,b).

In the crystal packing, intermolecular C2—H2A···O4 and C14—H14A···O3 hydrogen bonds (Table 1) link adjacent molecules into two-molecule-wide chains along the a axis (Fig. 2). The crystal packing is further stabilized by weak intermolecular C18—H18A···Cg1 (Table 1) and Cg2···Cg2 interactions [Cg2···Cg2ⁱ = 3.4441 (10) Å where Cg1 and Cg2 are the centroids of the C15-C20 benzene and pyrazole rings, respectively].

Related literature top

For general background to and applications of the title compound, see: Kalluraya et al. (1994); Rai & Kalluraya (2006); Rai et al. (2008); Sridhar & Perumal (2003). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995). For closely related structures, see: Goh et al. (2009a,b). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

3-Phenylsydnone (0.01 mol) and 1-phenyl-3-(5-nitro-2-furyl)-2-propyn-1-one (0.01 mol) were dissolved in dry xylene (10 ml) and refluxed for 4 h. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product obtained was purified by recrystallization from a mixture of ethanol and DMF. The solid obtained was collected by filtration, washed with ethanol and dried. Single crystals suitable for X-ray analysis were obtained from a 1:2 mixture of ethanol and DMF by slow evaporation.

Structure description top

For general background to and applications of the title compound, see: Kalluraya et al. (1994); Rai & Kalluraya (2006); Rai et al. (2008); Sridhar & Perumal (2003). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995). For closely related structures, see: Goh et al. (2009a,b). For the stability of the temperature controller used for 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

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme. An intramolecular hydrogen bond is shown as dashed line.
	Fig. 2. The crystal packing of the title compound, viewed along the c axis, showing two-molecule-wide chains along the a axis. Hydrogen atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.

[3-(5-Nitro-2-furyl)-1-phenyl-1H-pyrazol-4-yl](phenyl)methanone top

Crystal data top

C₂₀H₁₃N₃O₄	F(000) = 744
M_r = 359.33	D_x = 1.472 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2349 reflections
a = 11.2946 (12) Å	θ = 3.5–26.3°
b = 6.9755 (8) Å	µ = 0.11 mm⁻¹
c = 22.7064 (18) Å	T = 100 K
β = 115.015 (4)°	Block, brown
V = 1621.1 (3) Å³	0.24 × 0.15 × 0.07 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	4725 independent reflections
Radiation source: fine-focus sealed tube	2991 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
φ and ω scans	θ_max = 30.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
T_min = 0.976, T_max = 0.992	k = −9→9
17931 measured reflections	l = −31→31

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	All H-atom parameters refined
S = 1.02	w = 1/[σ²(F_o²) + (0.0464P)² + 0.6127P] where P = (F_o² + 2F_c²)/3
4725 reflections	(Δ/σ)_max = 0.001
296 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₀H₁₃N₃O₄	V = 1621.1 (3) Å³
M_r = 359.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.2946 (12) Å	µ = 0.11 mm⁻¹
b = 6.9755 (8) Å	T = 100 K
c = 22.7064 (18) Å	0.24 × 0.15 × 0.07 mm
β = 115.015 (4)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	4725 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2991 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.992	R_int = 0.056
17931 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.129	All H-atom parameters refined
S = 1.02	Δρ_max = 0.37 e Å⁻³
4725 reflections	Δρ_min = −0.24 e Å⁻³
296 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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(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

	x	y	z	U_iso*/U_eq
O1	1.26743 (11)	0.74226 (19)	1.00753 (6)	0.0293 (3)
O2	0.86733 (12)	0.95863 (19)	0.85528 (6)	0.0297 (3)
O3	1.55123 (13)	0.7939 (2)	0.98584 (7)	0.0411 (4)
O4	1.52027 (15)	0.6888 (3)	1.06817 (9)	0.0764 (7)
N1	0.96246 (13)	0.6915 (2)	1.05307 (6)	0.0206 (3)
N2	1.07625 (13)	0.6992 (2)	1.04603 (7)	0.0215 (3)
N3	1.48065 (16)	0.7520 (3)	1.01308 (9)	0.0382 (4)
C1	0.62475 (17)	0.6603 (3)	0.86532 (8)	0.0286 (4)
C2	0.49042 (19)	0.6327 (4)	0.83427 (9)	0.0359 (5)
C3	0.40950 (19)	0.7816 (4)	0.80076 (9)	0.0410 (5)
C4	0.4611 (2)	0.9603 (4)	0.79806 (10)	0.0434 (6)
C5	0.5954 (2)	0.9876 (3)	0.82757 (10)	0.0362 (5)
C6	0.67801 (17)	0.8374 (3)	0.86116 (8)	0.0271 (4)
C7	0.82209 (16)	0.8692 (3)	0.88763 (8)	0.0238 (4)
C8	0.90414 (16)	0.7934 (2)	0.95280 (8)	0.0213 (3)
C9	1.04207 (16)	0.7631 (2)	0.98559 (8)	0.0208 (3)
C10	1.14371 (16)	0.7910 (2)	0.96325 (8)	0.0226 (4)
C11	1.14713 (18)	0.8593 (3)	0.90780 (9)	0.0278 (4)
C12	1.27856 (18)	0.8549 (3)	0.91693 (9)	0.0294 (4)
C13	1.34517 (17)	0.7833 (3)	0.97709 (9)	0.0282 (4)
C14	0.85851 (16)	0.7448 (2)	0.99826 (8)	0.0216 (3)
C15	0.96295 (16)	0.6275 (2)	1.11294 (8)	0.0209 (3)
C16	1.07647 (16)	0.5522 (3)	1.16079 (8)	0.0233 (4)
C17	1.07388 (18)	0.4800 (3)	1.21724 (9)	0.0281 (4)
C18	0.96039 (18)	0.4857 (3)	1.22655 (9)	0.0282 (4)
C19	0.84901 (18)	0.5655 (3)	1.17896 (9)	0.0273 (4)
C20	0.84850 (17)	0.6368 (3)	1.12181 (8)	0.0238 (4)
H1A	0.6830 (18)	0.558 (3)	0.8899 (9)	0.024 (5)*
H2A	0.458 (2)	0.505 (3)	0.8376 (11)	0.047 (7)*
H3A	0.315 (2)	0.757 (3)	0.7776 (11)	0.047 (6)*
H4A	0.406 (2)	1.071 (4)	0.7748 (12)	0.057 (7)*
H5A	0.635 (2)	1.110 (4)	0.8263 (11)	0.048 (7)*
H11A	1.071 (2)	0.900 (4)	0.8687 (12)	0.061 (7)*
H12A	1.319 (2)	0.895 (3)	0.8890 (10)	0.041 (6)*
H14A	0.7722 (19)	0.741 (3)	0.9963 (9)	0.028 (5)*
H16A	1.1530 (18)	0.549 (3)	1.1519 (9)	0.025 (5)*
H17A	1.150 (2)	0.425 (3)	1.2493 (10)	0.039 (6)*
H18A	0.9566 (19)	0.433 (3)	1.2648 (10)	0.034 (5)*
H19A	0.7709 (17)	0.575 (3)	1.1840 (8)	0.022 (5)*
H20A	0.7707 (18)	0.686 (3)	1.0903 (9)	0.022 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0199 (6)	0.0361 (7)	0.0344 (7)	0.0003 (5)	0.0140 (5)	0.0054 (6)
O2	0.0304 (7)	0.0320 (7)	0.0293 (6)	−0.0019 (6)	0.0152 (5)	0.0027 (6)
O3	0.0260 (7)	0.0555 (10)	0.0492 (8)	−0.0051 (7)	0.0230 (6)	−0.0074 (7)
O4	0.0283 (8)	0.1271 (18)	0.0727 (12)	0.0171 (10)	0.0201 (8)	0.0604 (13)
N1	0.0185 (7)	0.0227 (7)	0.0226 (7)	−0.0021 (6)	0.0106 (5)	−0.0021 (6)
N2	0.0184 (6)	0.0232 (7)	0.0252 (7)	−0.0015 (6)	0.0115 (5)	−0.0030 (6)
N3	0.0244 (8)	0.0450 (11)	0.0475 (10)	0.0010 (7)	0.0176 (7)	0.0061 (9)
C1	0.0235 (9)	0.0393 (11)	0.0230 (8)	0.0008 (8)	0.0098 (7)	0.0008 (8)
C2	0.0274 (10)	0.0548 (14)	0.0264 (9)	−0.0065 (10)	0.0125 (8)	−0.0022 (10)
C3	0.0222 (9)	0.0738 (17)	0.0254 (9)	0.0009 (10)	0.0086 (8)	0.0023 (10)
C4	0.0268 (10)	0.0670 (16)	0.0350 (10)	0.0134 (11)	0.0116 (8)	0.0175 (11)
C5	0.0324 (10)	0.0443 (13)	0.0337 (10)	0.0069 (10)	0.0157 (8)	0.0113 (9)
C6	0.0240 (8)	0.0385 (11)	0.0205 (8)	0.0027 (8)	0.0110 (7)	0.0013 (8)
C7	0.0255 (8)	0.0242 (9)	0.0232 (8)	0.0008 (7)	0.0117 (7)	−0.0024 (7)
C8	0.0214 (8)	0.0199 (8)	0.0242 (8)	−0.0021 (7)	0.0112 (6)	−0.0029 (7)
C9	0.0216 (8)	0.0172 (8)	0.0246 (8)	−0.0027 (7)	0.0108 (6)	−0.0050 (7)
C10	0.0189 (8)	0.0216 (8)	0.0271 (8)	−0.0021 (7)	0.0095 (7)	−0.0040 (7)
C11	0.0258 (9)	0.0337 (10)	0.0276 (9)	−0.0023 (8)	0.0148 (7)	−0.0026 (8)
C12	0.0276 (9)	0.0352 (11)	0.0303 (9)	−0.0065 (8)	0.0171 (7)	−0.0070 (8)
C13	0.0193 (8)	0.0301 (10)	0.0387 (10)	−0.0020 (7)	0.0157 (7)	−0.0026 (8)
C14	0.0197 (8)	0.0214 (8)	0.0239 (8)	0.0003 (7)	0.0095 (6)	−0.0030 (7)
C15	0.0225 (8)	0.0196 (8)	0.0221 (7)	−0.0030 (7)	0.0108 (6)	−0.0027 (7)
C16	0.0207 (8)	0.0245 (9)	0.0257 (8)	−0.0017 (7)	0.0106 (7)	−0.0032 (7)
C17	0.0270 (9)	0.0287 (10)	0.0251 (8)	−0.0012 (8)	0.0077 (7)	0.0007 (8)
C18	0.0327 (10)	0.0291 (10)	0.0240 (8)	−0.0073 (8)	0.0131 (7)	−0.0024 (8)
C19	0.0254 (9)	0.0305 (10)	0.0315 (9)	−0.0041 (8)	0.0173 (7)	−0.0042 (8)
C20	0.0204 (8)	0.0248 (9)	0.0262 (8)	−0.0013 (7)	0.0099 (7)	−0.0020 (7)

Geometric parameters (Å, º) top

O1—C13	1.358 (2)	C7—C8	1.472 (2)
O1—C10	1.375 (2)	C8—C14	1.377 (2)
O2—C7	1.228 (2)	C8—C9	1.430 (2)
O3—N3	1.233 (2)	C9—C10	1.451 (2)
O4—N3	1.219 (2)	C10—C11	1.362 (2)
N1—C14	1.353 (2)	C11—C12	1.410 (3)
N1—N2	1.3616 (18)	C11—H11A	0.98 (2)
N1—C15	1.429 (2)	C12—C13	1.346 (3)
N2—C9	1.335 (2)	C12—H12A	0.96 (2)
N3—C13	1.414 (2)	C14—H14A	0.96 (2)
C1—C2	1.390 (3)	C15—C16	1.387 (2)
C1—C6	1.395 (3)	C15—C20	1.391 (2)
C1—H1A	0.97 (2)	C16—C17	1.389 (2)
C2—C3	1.380 (3)	C16—H16A	0.968 (18)
C2—H2A	0.98 (2)	C17—C18	1.385 (3)
C3—C4	1.388 (3)	C17—H17A	0.94 (2)
C3—H3A	0.99 (2)	C18—C19	1.382 (3)
C4—C5	1.389 (3)	C18—H18A	0.96 (2)
C4—H4A	1.00 (3)	C19—C20	1.387 (2)
C5—C6	1.396 (3)	C19—H19A	0.939 (18)
C5—H5A	0.97 (2)	C20—H20A	0.933 (18)
C6—C7	1.494 (2)

C13—O1—C10	104.57 (13)	C8—C9—C10	130.30 (15)
C14—N1—N2	112.10 (13)	C11—C10—O1	110.18 (14)
C14—N1—C15	127.88 (14)	C11—C10—C9	134.91 (16)
N2—N1—C15	120.00 (13)	O1—C10—C9	114.89 (14)
C9—N2—N1	104.88 (13)	C10—C11—C12	107.23 (16)
O4—N3—O3	124.47 (17)	C10—C11—H11A	125.5 (14)
O4—N3—C13	119.14 (17)	C12—C11—H11A	127.2 (14)
O3—N3—C13	116.38 (17)	C13—C12—C11	105.03 (16)
C2—C1—C6	119.85 (19)	C13—C12—H12A	124.0 (13)
C2—C1—H1A	121.2 (11)	C11—C12—H12A	131.0 (13)
C6—C1—H1A	118.9 (11)	C12—C13—O1	112.99 (15)
C3—C2—C1	120.1 (2)	C12—C13—N3	130.37 (17)
C3—C2—H2A	123.0 (14)	O1—C13—N3	116.60 (16)
C1—C2—H2A	116.9 (13)	N1—C14—C8	107.64 (15)
C2—C3—C4	120.51 (19)	N1—C14—H14A	120.4 (11)
C2—C3—H3A	118.6 (14)	C8—C14—H14A	132.0 (11)
C4—C3—H3A	120.8 (14)	C16—C15—C20	120.80 (16)
C3—C4—C5	119.7 (2)	C16—C15—N1	119.63 (14)
C3—C4—H4A	122.8 (14)	C20—C15—N1	119.55 (15)
C5—C4—H4A	117.5 (14)	C15—C16—C17	119.16 (16)
C4—C5—C6	120.2 (2)	C15—C16—H16A	117.3 (11)
C4—C5—H5A	122.1 (13)	C17—C16—H16A	123.6 (11)
C6—C5—H5A	117.7 (14)	C18—C17—C16	120.84 (17)
C1—C6—C5	119.62 (17)	C18—C17—H17A	119.5 (13)
C1—C6—C7	122.14 (17)	C16—C17—H17A	119.6 (13)
C5—C6—C7	118.10 (18)	C19—C18—C17	119.16 (17)
O2—C7—C8	122.64 (16)	C19—C18—H18A	119.1 (12)
O2—C7—C6	119.53 (15)	C17—C18—H18A	121.7 (12)
C8—C7—C6	117.83 (15)	C18—C19—C20	121.20 (17)
C14—C8—C9	104.11 (14)	C18—C19—H19A	121.7 (11)
C14—C8—C7	124.45 (15)	C20—C19—H19A	117.1 (11)
C9—C8—C7	131.35 (15)	C19—C20—C15	118.82 (16)
N2—C9—C8	111.25 (14)	C19—C20—H20A	118.7 (11)
N2—C9—C10	118.45 (15)	C15—C20—H20A	122.5 (11)

C14—N1—N2—C9	1.32 (18)	C8—C9—C10—O1	−178.34 (16)
C15—N1—N2—C9	179.83 (15)	O1—C10—C11—C12	−0.2 (2)
C6—C1—C2—C3	−1.6 (3)	C9—C10—C11—C12	178.25 (19)
C1—C2—C3—C4	−0.4 (3)	C10—C11—C12—C13	0.3 (2)
C2—C3—C4—C5	2.1 (3)	C11—C12—C13—O1	−0.3 (2)
C3—C4—C5—C6	−1.6 (3)	C11—C12—C13—N3	−177.8 (2)
C2—C1—C6—C5	2.1 (3)	C10—O1—C13—C12	0.2 (2)
C2—C1—C6—C7	−173.56 (16)	C10—O1—C13—N3	178.07 (16)
C4—C5—C6—C1	−0.5 (3)	O4—N3—C13—C12	178.3 (2)
C4—C5—C6—C7	175.34 (18)	O3—N3—C13—C12	−0.8 (3)
C1—C6—C7—O2	135.87 (18)	O4—N3—C13—O1	0.9 (3)
C5—C6—C7—O2	−39.8 (2)	O3—N3—C13—O1	−178.27 (17)
C1—C6—C7—C8	−45.1 (2)	N2—N1—C14—C8	−1.0 (2)
C5—C6—C7—C8	139.15 (17)	C15—N1—C14—C8	−179.35 (16)
O2—C7—C8—C14	159.65 (17)	C9—C8—C14—N1	0.24 (19)
C6—C7—C8—C14	−19.3 (3)	C7—C8—C14—N1	−176.58 (16)
O2—C7—C8—C9	−16.2 (3)	C14—N1—C15—C16	170.60 (17)
C6—C7—C8—C9	164.80 (17)	N2—N1—C15—C16	−7.6 (2)
N1—N2—C9—C8	−1.14 (18)	C14—N1—C15—C20	−7.7 (3)
N1—N2—C9—C10	178.84 (14)	N2—N1—C15—C20	174.08 (15)
C14—C8—C9—N2	0.58 (19)	C20—C15—C16—C17	2.0 (3)
C7—C8—C9—N2	177.09 (17)	N1—C15—C16—C17	−176.24 (16)
C14—C8—C9—C10	−179.40 (17)	C15—C16—C17—C18	−1.1 (3)
C7—C8—C9—C10	−2.9 (3)	C16—C17—C18—C19	−0.4 (3)
C13—O1—C10—C11	0.0 (2)	C17—C18—C19—C20	1.1 (3)
C13—O1—C10—C9	−178.77 (15)	C18—C19—C20—C15	−0.2 (3)
N2—C9—C10—C11	−176.7 (2)	C16—C15—C20—C19	−1.3 (3)
C8—C9—C10—C11	3.2 (3)	N1—C15—C20—C19	176.91 (16)
N2—C9—C10—O1	1.7 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C15–C20 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O4ⁱ	0.98 (2)	2.45 (2)	3.190 (3)	131.8 (17)
C11—H11A···O2	0.98 (3)	2.23 (3)	2.950 (3)	130 (2)
C14—H14A···O3ⁱⁱ	0.96 (2)	2.43 (2)	3.379 (3)	169.3 (17)
C18—H18A···Cg1ⁱⁱⁱ	0.96 (2)	2.96 (2)	3.671 (2)	132.0 (16)

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) x−1, y, z; (iii) −x+2, y−1/2, −z+5/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₃N₃O₄
M_r	359.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.2946 (12), 6.9755 (8), 22.7064 (18)
β (°)	115.015 (4)
V (Å³)	1621.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.24 × 0.15 × 0.07

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.976, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	17931, 4725, 2991
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.129, 1.02
No. of reflections	4725
No. of parameters	296
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.24

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C15–C20 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O4ⁱ	0.98 (2)	2.45 (2)	3.190 (3)	131.8 (17)
C11—H11A···O2	0.98 (3)	2.23 (3)	2.950 (3)	130 (2)
C14—H14A···O3ⁱⁱ	0.96 (2)	2.43 (2)	3.379 (3)	169.3 (17)
C18—H18A···Cg1ⁱⁱⁱ	0.96 (2)	2.96 (2)	3.671 (2)	132.0 (16)

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) x−1, y, z; (iii) −x+2, y−1/2, −z+5/2.

Footnotes

‡Thomson Reuters ResearcherID: C-7576-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship.

References

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