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

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

doi:10.1107/S1600536809047217

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages o3088-o3089

doi:10.1107/S1600536809047217

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

Jia Hao Goh,^a ‡ Hoong-Kun Fun,^a ^*§ Nithinchandra ^b and B. Kalluraya ^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 4 November 2009; accepted 9 November 2009; online 14 November 2009)

In the title pyrazole compound, C₂₁H₁₅N₃O₄, an intramolecular C—H⋯O hydrogen bond generates an S(7) ring motif. The essentially planar furan and pyrazole rings [maximum atomic deviations of 0.011 (2) and 0.006 (2) Å, respectively] make a dihedral angle of 9.21 (11)°. The nitro group is approximately coplanar with the attached furan ring, as indicated by the dihedral angle of 4.5 (2)°. In the crystal structure, intermolecular C—H⋯O interactions form bifurcated hydrogen bonds, generating R¹₂(7) ring motifs. These hydrogen bonds link the molecules into infinite chains along the a axis. The crystal structure is further stabilized by weak intermolecular π–π interactions [centroid–centroid distance = 3.4118 (10) Å].

Related literature

For general background to and applications of the title compound, see: Hegde et al. (2006 ); Kalluraya et al. (1994 ); Rai & Kalluraya (2006 ); Rai et al. (2008 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₁H₁₅N₃O₄
M_r = 373.36
Monoclinic, P 2₁ /c
a = 11.3859 (2) Å
b = 7.5746 (2) Å
c = 21.0008 (4) Å
β = 107.202 (1)°
V = 1730.17 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.19 × 0.18 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.981, T_max = 0.990
22336 measured reflections
5085 independent reflections
2678 reflections with I > 2σ(I)
R_int = 0.085

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.135
S = 1.02
5085 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O2	0.93	2.24	2.902 (2)	128
C14—H14A⋯O3ⁱ	0.93	2.55	3.467 (2)	168
C20—H20A⋯O3ⁱ	0.93	2.46	3.373 (3)	166
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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: 10.1107/S1600536809047217/fj2257sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809047217/fj2257Isup2.hkl

checkCIF report

Comment top

The pyrazole nucleus constitutes an interesting class of organic compound with diverse chemical applications. They possess anti-pyretic, anti-tumor, tranquilizing and herbicidal activities. Sydnones are easily accessible aromatic compounds and versatile synthetic intermediates with a masked azomethine imine unit. The 1,3-dipolar cycloaddition reaction with various dipolarophiles offers a convenient synthetic route for the preparation of pyrazole derivatives and has been studied extensively (Rai & Kalluraya, 2006; Rai et al., 2008).

The incorporation of 5-nitrofuran moiety into various heterocyclic systems has found to increase their biological activities. We have reported a few heterocyclic systems carrying 5-nitrofuran moiety as potent anti-microbial agents (Hegde et al., 2006). In continuation of our studies on 1,3-dipolar cycloaddition reactions of sydnones with dipolarophiles carrying nitrofuran moiety (Kalluraya et al., 1994), we herein report the synthesis of this new pyrazole.

In the title pyrazole compound, an intramolecular C11—H11A···O2 hydrogen bond (Table 1) generates a seven-membered ring, producing an S(7) ring motif (Fig. 1, Bernstein et al., 1995). The furan (C10-C13/O1) and pyrazole (C8/C9/N2/N1/C14) rings are essentially planar, with maximum deviations of 0.011 (2) and 0.006 (2) Å, respectively, for atoms C10 and N2. These two rings are slightly twisted to one another, making a dihedral angle of 9.21 (11)° between them. The nitro group is approximately coplanar with the attached furan ring, as shown by the dihedral angle formed between the mean plane through N3/O3/O4 and the C10-C13/O1 furan ring of 4.5 (2)°. The bond lengths (Allen et al., 1987) and angles observed are within normal ranges.

In the crystal structure (Fig. 2), intermolecular C14—H14A···O3 and C20—H20A···O3 interactions (Table 1) form bifurcated acceptor hydrogen bonds which generate R¹₂(7) ring motifs. These hydrogen bonds link the molecules into one-dimensional infinite chains along the a axis. The crystal structure is further stabillized by weak intermolecular π–π interactions [Cg1···Cg1 = 3.4118 (10) Å; Cg1 is the centroid of the C8/C9/N2/N1/C14 pyrazole ring].

Related literature top

For general background to and applications of the title compound, see: Hegde et al. (2006); Kalluraya et al. (1994); Rai & Kalluraya (2006); Rai et al. (2008). For hydrogen-bond motifs, see : Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

3-Phenyl sydnone (0.01 mol) and 1-(p-methylphenyl)-3-(5-nitro-2-furyl)-2-propyn-1-one (0.01 mol) were dissolved in 10 ml dry xylene 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 ethanol and DMF mixture. 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 DMF and ethanol by slow evaporation.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 structure of the title compound, viewed along the b axis, showing one dimensional infinite chains along the a axis. Intermolecular hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₂₁H₁₅N₃O₄	F(000) = 776
M_r = 373.36	D_x = 1.433 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2474 reflections
a = 11.3859 (2) Å	θ = 3.3–30.1°
b = 7.5746 (2) Å	µ = 0.10 mm⁻¹
c = 21.0008 (4) Å	T = 100 K
β = 107.202 (1)°	Block, brown
V = 1730.17 (6) Å³	0.19 × 0.18 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5085 independent reflections
Radiation source: fine-focus sealed tube	2678 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.085
ϕ and ω scans	θ_max = 30.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −15→16
T_min = 0.981, T_max = 0.990	k = −10→9
22336 measured reflections	l = −29→29

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0519P)² + 0.0761P] where P = (F_o² + 2F_c²)/3
5085 reflections	(Δ/σ)_max < 0.001
254 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₁H₁₅N₃O₄	V = 1730.17 (6) Å³
M_r = 373.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.3859 (2) Å	µ = 0.10 mm⁻¹
b = 7.5746 (2) Å	T = 100 K
c = 21.0008 (4) Å	0.19 × 0.18 × 0.10 mm
β = 107.202 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5085 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2678 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.990	R_int = 0.085
22336 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.02	Δρ_max = 0.27 e Å⁻³
5085 reflections	Δρ_min = −0.28 e Å⁻³
254 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems 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	−0.26961 (11)	0.68826 (17)	−0.02101 (6)	0.0275 (3)
O2	0.05600 (11)	0.98467 (18)	0.11675 (6)	0.0286 (3)
O3	−0.56846 (12)	0.7483 (2)	−0.01746 (8)	0.0464 (4)
O4	−0.49541 (13)	0.5852 (2)	−0.08230 (8)	0.0473 (4)
N1	0.04825 (13)	0.6498 (2)	−0.06270 (7)	0.0219 (4)
N2	−0.06690 (14)	0.6518 (2)	−0.05573 (8)	0.0245 (4)
N3	−0.48241 (15)	0.6877 (2)	−0.03543 (9)	0.0340 (4)
C1	0.33869 (18)	0.7702 (3)	0.12408 (9)	0.0284 (5)
H1A	0.3085	0.6624	0.1049	0.034*
C2	0.46370 (18)	0.7905 (3)	0.15579 (10)	0.0320 (5)
H2A	0.5160	0.6946	0.1585	0.038*
C3	0.51237 (18)	0.9510 (3)	0.18361 (10)	0.0310 (5)
C4	0.43195 (18)	1.0917 (3)	0.17911 (9)	0.0294 (5)
H4A	0.4628	1.2009	0.1965	0.035*
C5	0.30696 (18)	1.0725 (3)	0.14930 (9)	0.0269 (5)
H5A	0.2546	1.1675	0.1480	0.032*
C6	0.25869 (17)	0.9108 (3)	0.12104 (9)	0.0248 (4)
C7	0.12233 (17)	0.8988 (2)	0.09159 (9)	0.0222 (4)
C8	0.06949 (16)	0.7914 (2)	0.03174 (9)	0.0222 (4)
C9	−0.05508 (16)	0.7393 (2)	0.00105 (9)	0.0220 (4)
C10	−0.16698 (17)	0.7701 (2)	0.01993 (9)	0.0236 (4)
C11	−0.19765 (17)	0.8688 (3)	0.06673 (10)	0.0281 (5)
H11A	−0.1443	0.9338	0.1007	0.034*
C12	−0.32650 (18)	0.8533 (3)	0.05368 (10)	0.0327 (5)
H12A	−0.3752	0.9068	0.0767	0.039*
C13	−0.36327 (17)	0.7451 (3)	0.00098 (10)	0.0274 (5)
C14	0.13067 (17)	0.7302 (2)	−0.01160 (9)	0.0220 (4)
H14A	0.2143	0.7425	−0.0064	0.026*
C15	0.06792 (17)	0.5688 (2)	−0.12035 (9)	0.0232 (4)
C16	−0.02628 (18)	0.4746 (3)	−0.16354 (9)	0.0273 (5)
H16A	−0.1025	0.4664	−0.1559	0.033*
C17	−0.00643 (19)	0.3924 (3)	−0.21841 (10)	0.0331 (5)
H17A	−0.0693	0.3275	−0.2473	0.040*
C18	0.10610 (19)	0.4062 (3)	−0.23042 (10)	0.0345 (5)
H18A	0.1190	0.3516	−0.2674	0.041*
C19	0.19937 (19)	0.5017 (3)	−0.18716 (10)	0.0328 (5)
H19A	0.2751	0.5111	−0.1953	0.039*
C20	0.18140 (18)	0.5839 (3)	−0.13170 (10)	0.0278 (5)
H20A	0.2445	0.6481	−0.1026	0.033*
C21	0.64761 (18)	0.9736 (3)	0.21836 (11)	0.0425 (6)
H21A	0.6768	1.0784	0.2022	0.064*
H21B	0.6916	0.8729	0.2095	0.064*
H21C	0.6607	0.9838	0.2655	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0179 (7)	0.0278 (8)	0.0350 (8)	−0.0026 (6)	0.0053 (6)	0.0027 (6)
O2	0.0245 (8)	0.0303 (8)	0.0307 (7)	−0.0007 (6)	0.0078 (6)	−0.0007 (6)
O3	0.0191 (8)	0.0648 (12)	0.0557 (10)	−0.0010 (8)	0.0118 (8)	−0.0040 (9)
O4	0.0270 (9)	0.0471 (10)	0.0633 (11)	−0.0079 (8)	0.0062 (8)	−0.0162 (9)
N1	0.0163 (8)	0.0217 (9)	0.0264 (8)	−0.0011 (7)	0.0045 (7)	0.0028 (7)
N2	0.0185 (9)	0.0234 (9)	0.0315 (9)	0.0000 (7)	0.0073 (7)	0.0040 (7)
N3	0.0214 (10)	0.0361 (11)	0.0429 (11)	−0.0028 (8)	0.0069 (9)	0.0053 (9)
C1	0.0259 (11)	0.0278 (12)	0.0283 (11)	−0.0008 (10)	0.0031 (9)	0.0010 (9)
C2	0.0228 (11)	0.0345 (13)	0.0354 (12)	0.0051 (10)	0.0035 (10)	0.0009 (10)
C3	0.0213 (11)	0.0412 (14)	0.0279 (11)	−0.0021 (10)	0.0036 (9)	−0.0005 (10)
C4	0.0262 (11)	0.0302 (12)	0.0292 (11)	−0.0049 (10)	0.0040 (9)	−0.0017 (9)
C5	0.0244 (11)	0.0279 (12)	0.0279 (10)	0.0009 (9)	0.0070 (9)	0.0018 (9)
C6	0.0205 (10)	0.0289 (11)	0.0242 (10)	−0.0020 (9)	0.0052 (9)	0.0042 (9)
C7	0.0202 (10)	0.0216 (11)	0.0237 (10)	−0.0023 (8)	0.0046 (8)	0.0055 (8)
C8	0.0180 (10)	0.0207 (10)	0.0259 (10)	−0.0008 (8)	0.0033 (8)	0.0051 (8)
C9	0.0192 (10)	0.0184 (10)	0.0260 (10)	0.0010 (8)	0.0031 (8)	0.0058 (8)
C10	0.0187 (10)	0.0206 (11)	0.0283 (10)	−0.0031 (8)	0.0021 (9)	0.0059 (8)
C11	0.0205 (11)	0.0307 (12)	0.0321 (11)	−0.0018 (9)	0.0062 (9)	0.0013 (9)
C12	0.0242 (11)	0.0372 (13)	0.0386 (12)	−0.0002 (10)	0.0124 (10)	0.0007 (10)
C13	0.0149 (10)	0.0299 (12)	0.0363 (11)	−0.0010 (9)	0.0059 (9)	0.0066 (10)
C14	0.0164 (10)	0.0212 (11)	0.0251 (10)	−0.0016 (8)	0.0013 (8)	0.0052 (8)
C15	0.0229 (10)	0.0205 (10)	0.0240 (10)	0.0020 (9)	0.0034 (9)	0.0060 (8)
C16	0.0209 (11)	0.0295 (12)	0.0281 (10)	−0.0006 (9)	0.0020 (9)	0.0042 (9)
C17	0.0316 (13)	0.0349 (13)	0.0267 (11)	−0.0021 (10)	−0.0006 (10)	0.0000 (10)
C18	0.0383 (13)	0.0374 (13)	0.0269 (11)	0.0072 (11)	0.0083 (10)	0.0007 (10)
C19	0.0296 (12)	0.0347 (13)	0.0365 (12)	0.0051 (10)	0.0136 (10)	0.0067 (10)
C20	0.0217 (11)	0.0275 (11)	0.0319 (11)	−0.0009 (9)	0.0042 (9)	0.0030 (9)
C21	0.0238 (12)	0.0503 (16)	0.0482 (14)	−0.0021 (11)	0.0024 (11)	−0.0084 (12)

Geometric parameters (Å, º) top

O1—C13	1.352 (2)	C8—C14	1.380 (2)
O1—C10	1.377 (2)	C8—C9	1.429 (2)
O2—C7	1.229 (2)	C9—C10	1.461 (2)
O3—N3	1.2377 (19)	C10—C11	1.360 (3)
O4—N3	1.228 (2)	C11—C12	1.415 (3)
N1—C14	1.345 (2)	C11—H11A	0.9300
N1—N2	1.3617 (19)	C12—C13	1.341 (3)
N1—C15	1.433 (2)	C12—H12A	0.9300
N2—C9	1.336 (2)	C14—H14A	0.9300
N3—C13	1.414 (2)	C15—C16	1.381 (3)
C1—C2	1.390 (3)	C15—C20	1.386 (2)
C1—C6	1.391 (3)	C16—C17	1.386 (3)
C1—H1A	0.9300	C16—H16A	0.9300
C2—C3	1.391 (3)	C17—C18	1.381 (3)
C2—H2A	0.9300	C17—H17A	0.9300
C3—C4	1.390 (3)	C18—C19	1.380 (3)
C3—C21	1.506 (3)	C18—H18A	0.9300
C4—C5	1.383 (3)	C19—C20	1.388 (3)
C4—H4A	0.9300	C19—H19A	0.9300
C5—C6	1.400 (3)	C20—H20A	0.9300
C5—H5A	0.9300	C21—H21A	0.9600
C6—C7	1.494 (3)	C21—H21B	0.9600
C7—C8	1.468 (3)	C21—H21C	0.9600

C13—O1—C10	104.64 (15)	O1—C10—C9	113.95 (16)
C14—N1—N2	112.07 (14)	C10—C11—C12	106.71 (18)
C14—N1—C15	128.45 (15)	C10—C11—H11A	126.6
N2—N1—C15	119.47 (15)	C12—C11—H11A	126.6
C9—N2—N1	104.81 (15)	C13—C12—C11	105.26 (17)
O4—N3—O3	124.09 (18)	C13—C12—H12A	127.4
O4—N3—C13	119.78 (17)	C11—C12—H12A	127.4
O3—N3—C13	116.12 (18)	C12—C13—O1	113.05 (17)
C2—C1—C6	120.08 (19)	C12—C13—N3	130.51 (18)
C2—C1—H1A	120.0	O1—C13—N3	116.41 (18)
C6—C1—H1A	120.0	N1—C14—C8	108.03 (16)
C1—C2—C3	121.47 (19)	N1—C14—H14A	126.0
C1—C2—H2A	119.3	C8—C14—H14A	126.0
C3—C2—H2A	119.3	C16—C15—C20	120.81 (18)
C4—C3—C2	117.98 (19)	C16—C15—N1	119.41 (16)
C4—C3—C21	120.30 (19)	C20—C15—N1	119.78 (17)
C2—C3—C21	121.72 (19)	C15—C16—C17	119.49 (17)
C5—C4—C3	121.27 (19)	C15—C16—H16A	120.3
C5—C4—H4A	119.4	C17—C16—H16A	120.3
C3—C4—H4A	119.4	C18—C17—C16	120.4 (2)
C4—C5—C6	120.43 (18)	C18—C17—H17A	119.8
C4—C5—H5A	119.8	C16—C17—H17A	119.8
C6—C5—H5A	119.8	C19—C18—C17	119.62 (19)
C1—C6—C5	118.74 (18)	C19—C18—H18A	120.2
C1—C6—C7	123.94 (18)	C17—C18—H18A	120.2
C5—C6—C7	117.27 (17)	C18—C19—C20	120.77 (18)
O2—C7—C8	120.88 (17)	C18—C19—H19A	119.6
O2—C7—C6	119.03 (17)	C20—C19—H19A	119.6
C8—C7—C6	120.04 (16)	C15—C20—C19	118.91 (19)
C14—C8—C9	103.72 (16)	C15—C20—H20A	120.5
C14—C8—C7	126.29 (17)	C19—C20—H20A	120.5
C9—C8—C7	129.78 (16)	C3—C21—H21A	109.5
N2—C9—C8	111.36 (15)	C3—C21—H21B	109.5
N2—C9—C10	117.12 (17)	H21A—C21—H21B	109.5
C8—C9—C10	131.49 (18)	C3—C21—H21C	109.5
C11—C10—O1	110.30 (15)	H21A—C21—H21C	109.5
C11—C10—C9	135.64 (18)	H21B—C21—H21C	109.5

C14—N1—N2—C9	1.1 (2)	N2—C9—C10—O1	6.0 (2)
C15—N1—N2—C9	−178.35 (15)	C8—C9—C10—O1	−176.27 (17)
C6—C1—C2—C3	−1.6 (3)	O1—C10—C11—C12	−1.9 (2)
C1—C2—C3—C4	0.3 (3)	C9—C10—C11—C12	174.0 (2)
C1—C2—C3—C21	179.66 (18)	C10—C11—C12—C13	0.9 (2)
C2—C3—C4—C5	1.4 (3)	C11—C12—C13—O1	0.4 (2)
C21—C3—C4—C5	−177.92 (17)	C11—C12—C13—N3	−177.31 (19)
C3—C4—C5—C6	−1.9 (3)	C10—O1—C13—C12	−1.5 (2)
C2—C1—C6—C5	1.2 (3)	C10—O1—C13—N3	176.56 (16)
C2—C1—C6—C7	−176.31 (17)	O4—N3—C13—C12	−179.2 (2)
C4—C5—C6—C1	0.5 (3)	O3—N3—C13—C12	1.7 (3)
C4—C5—C6—C7	178.19 (16)	O4—N3—C13—O1	3.2 (3)
C1—C6—C7—O2	144.79 (18)	O3—N3—C13—O1	−175.94 (16)
C5—C6—C7—O2	−32.7 (2)	N2—N1—C14—C8	−0.6 (2)
C1—C6—C7—C8	−37.8 (3)	C15—N1—C14—C8	178.73 (16)
C5—C6—C7—C8	144.68 (17)	C9—C8—C14—N1	−0.1 (2)
O2—C7—C8—C14	160.61 (18)	C7—C8—C14—N1	−175.08 (17)
C6—C7—C8—C14	−16.7 (3)	C14—N1—C15—C16	172.41 (18)
O2—C7—C8—C9	−13.1 (3)	N2—N1—C15—C16	−8.3 (3)
C6—C7—C8—C9	169.56 (18)	C14—N1—C15—C20	−6.8 (3)
N1—N2—C9—C8	−1.1 (2)	N2—N1—C15—C20	172.55 (16)
N1—N2—C9—C10	177.03 (15)	C20—C15—C16—C17	0.8 (3)
C14—C8—C9—N2	0.8 (2)	N1—C15—C16—C17	−178.34 (17)
C7—C8—C9—N2	175.53 (17)	C15—C16—C17—C18	−0.9 (3)
C14—C8—C9—C10	−177.03 (19)	C16—C17—C18—C19	0.4 (3)
C7—C8—C9—C10	−2.3 (3)	C17—C18—C19—C20	0.0 (3)
C13—O1—C10—C11	2.0 (2)	C16—C15—C20—C19	−0.4 (3)
C13—O1—C10—C9	−174.79 (15)	N1—C15—C20—C19	178.79 (17)
N2—C9—C10—C11	−169.7 (2)	C18—C19—C20—C15	−0.1 (3)
C8—C9—C10—C11	8.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O2	0.93	2.24	2.902 (2)	128
C14—H14A···O3ⁱ	0.93	2.55	3.467 (2)	168
C20—H20A···O3ⁱ	0.93	2.46	3.373 (3)	166

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₅N₃O₄
M_r	373.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.3859 (2), 7.5746 (2), 21.0008 (4)
β (°)	107.202 (1)
V (Å³)	1730.17 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.19 × 0.18 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.981, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	22336, 5085, 2678
R_int	0.085
(sin θ/λ)_max (Å⁻¹)	0.706

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.135, 1.02
No. of reflections	5085
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.28

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O2	0.9300	2.2400	2.902 (2)	128
C14—H14A···O3ⁱ	0.9300	2.5500	3.467 (2)	168
C20—H20A···O3ⁱ	0.9300	2.4600	3.373 (3)	166

Symmetry code: (i) x+1, y, z.

Footnotes

‡Thomson Reuters ResearcherID: C-7576-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and JHG 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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