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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 67| Part 10| October 2011| Page o2571
https://doi.org/10.1107/S1600536811034854

Ethyl 2-[2-(2-meth­­oxy­phen­yl)hydrazinyl­­idene]-3-oxo­butano­ate

Hoong-Kun Fun,a*‡ Madhukar Hemamalini,a Shobhitha Shettyb and BalaKrishna Kallurayab

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 19 August 2011; accepted 25 August 2011; online 14 September 2011)

In the title compound, C13H16N2O4, an intra­molecular N—H⋯O hydrogen bond generates an S(6) ring. The mol­ecule adopts an E configuration with respect to the central C=N double bond. In the crystal, symmetry-related mol­ecules are connected into chains along [010] via weak C—H⋯N hydrogen bonds. The crystal structure is further stabilized by weak C—H⋯π inter­actions.

Related literature

For details and applications of pyrazole derivatives, see: Rai et al. (2008[Rai, N. S., Kalluraya, B., Lingappa, B., Shenoy, S. & Puranic, V. G. (2008). Eur. J. Med. Chem, 43, 1715-1720.]); Girisha et al. (2010[Girisha, K.S., Kalluraya, B., Narayana, V. & Padmashree (2010). Eur. J. Med. Chem, 45, 4640-4644.]); Isloor et al. (2009[Isloor, A. M., Kalluraya, B. & Shetty, P. (2009). Eur. J. Med. Chem, 44, 3784-3787.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). 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

  • C13H16N2O4

  • Mr = 264.28

  • Monoclinic, P 21 /c

  • a = 10.1885 (4) Å

  • b = 11.4967 (4) Å

  • c = 13.2492 (5) Å

  • β = 120.003 (3)°

  • V = 1343.97 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 100 K

  • 0.75 × 0.27 × 0.20 mm
Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.931, Tmax = 0.981

  • 14963 measured reflections

  • 3909 independent reflections

  • 3123 reflections with I > 2σ(I)

  • Rint = 0.028
Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.116

  • S = 1.03

  • 3909 reflections

  • 179 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N1⋯O3 0.90 (2) 1.886 (19) 2.5715 (15) 131.6 (14)
C13—H13C⋯N2i 0.96 2.58 3.4835 (18) 156
C12—H12B⋯Cg1ii 0.96 2.92 3.6620 (15) 135
C13—H13B⋯Cg1iii 0.96 2.66 3.4887 (14) 145
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. 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

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811034854/lh5322sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811034854/lh5322Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811034854/lh5322Isup3.cml

checkCIF report


Comment top

Pyrazole derivatives are well established in the literature as important biologically effective heterocyclic compounds (Rai et al., 2008). These derivatives are the subject of many research studies due to their widespread potential pharmacological activities such as antiinflammatory (Girisha et al., 2010), antipyretic, antimicrobial (Isloor et al., 2009) and antiviral activities. The widely prescribed anti-inflammatory pyrazole derivatives, celecoxib and deracoxib, are selective COX-2 inhibitors with reduced ulcerogenic side effects. The title compound, ethyl-2-[(2-methoxyphenyl) hydrazinylidene]-3-oxobutanoate is a key intermediate in the preparation of pyrazole derivative which in turn was obtained by the condensation of 2-[(2-substituted phenyl)hydrazinylidene]-3-oxobutanoate with thiosemicarbazide in glacial acetic acid medium.

Fig. 1 shows the molecular structure of the title compound (I). The molecule adopts an E-configuration with respect to the central C6═N1 double bond. An intramolecular N1—H1N1···O3 interaction generates an S(6) ring (Bernstein et al., 1995). In the crystal, (Fig. 2), adjacent molecules are interconnected into one-dimensional chains along [010] via intermolecular C13—H13C···N2i hydrogen bonds. Furthermore, the crystal structure is stabilized by C—H···π interactions (Table 1) involving the C1–C6 (centroid Cg1) ring.

Related literature top

For details and applications of pyrazole derivatives, see: Rai et al. (2008); Girisha et al. (2010); Isloor et al. (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was prepared by dissolving 2-methoxy aniline (0.01 mol) in dilute hydrochloric acid (10 ml) and cooled to 273K in an ice bath. To this, a cold solution of sodium nitrite (0.02 mol) was added. The resulting diazonium salt solution was filtered into a cold solution of ethyl acetoacetate (0.05 mol) and sodium acetate in ethanol. The separated yellow solid was filtered, washed with water and recrystallized from ethanol. Crystals suitable for X-ray analysis were obtained by slow evaporationfrom of a solution of (I) in a 1:2 mixture of DMF and ethanol.

Refinement top

Atom H1N1 was located in a difference Fourier map and refined freely [N–H = 0.898 (17) Å]. The remaining H atoms were positioned geometrically [C–H = 0.93–0.97 Å] and were refined using a riding model, with Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating group model was applied to the methyl groups.

Structure description top

Pyrazole derivatives are well established in the literature as important biologically effective heterocyclic compounds (Rai et al., 2008). These derivatives are the subject of many research studies due to their widespread potential pharmacological activities such as antiinflammatory (Girisha et al., 2010), antipyretic, antimicrobial (Isloor et al., 2009) and antiviral activities. The widely prescribed anti-inflammatory pyrazole derivatives, celecoxib and deracoxib, are selective COX-2 inhibitors with reduced ulcerogenic side effects. The title compound, ethyl-2-[(2-methoxyphenyl) hydrazinylidene]-3-oxobutanoate is a key intermediate in the preparation of pyrazole derivative which in turn was obtained by the condensation of 2-[(2-substituted phenyl)hydrazinylidene]-3-oxobutanoate with thiosemicarbazide in glacial acetic acid medium.

Fig. 1 shows the molecular structure of the title compound (I). The molecule adopts an E-configuration with respect to the central C6═N1 double bond. An intramolecular N1—H1N1···O3 interaction generates an S(6) ring (Bernstein et al., 1995). In the crystal, (Fig. 2), adjacent molecules are interconnected into one-dimensional chains along [010] via intermolecular C13—H13C···N2i hydrogen bonds. Furthermore, the crystal structure is stabilized by C—H···π interactions (Table 1) involving the C1–C6 (centroid Cg1) ring.

For details and applications of pyrazole derivatives, see: Rai et al. (2008); Girisha et al. (2010); Isloor et al. (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995). 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. An intramolecular hydrogen bond is shown by a dashed line.
[Figure 2] Fig. 2. The crystal packing of the title compound (I). H atoms not involing the hydrogen bond interactions are omitted for clarity. Hydrogen bonds are shown as dashed llines.
Ethyl 2-[2-(2-methoxyphenyl)hydrazinylidene]-3-oxobutanoate top
Crystal data top
C13H16N2O4F(000) = 560
Mr = 264.28Dx = 1.306 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7354 reflections
a = 10.1885 (4) Åθ = 2.5–30.8°
b = 11.4967 (4) ŵ = 0.10 mm−1
c = 13.2492 (5) ÅT = 100 K
β = 120.003 (3)°Needle, green
V = 1343.97 (9) Å30.75 × 0.27 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		3909 independent reflections
Radiation source: fine-focus sealed tube3123 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
φ and ω scansθmax = 30.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −14→13
Tmin = 0.931, Tmax = 0.981k = −16→16
14963 measured reflectionsl = −14→18
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0513P)2 + 0.4458P]
where P = (Fo2 + 2Fc2)/3
3909 reflections(Δ/σ)max < 0.001
179 parametersΔρmax = 0.35 e Å−3
0 restraintsΔρmin = −0.30 e Å−3
Crystal data top
C13H16N2O4V = 1343.97 (9) Å3
Mr = 264.28Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.1885 (4) ŵ = 0.10 mm−1
b = 11.4967 (4) ÅT = 100 K
c = 13.2492 (5) Å0.75 × 0.27 × 0.20 mm
β = 120.003 (3)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		3909 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		3123 reflections with I > 2σ(I)
Tmin = 0.931, Tmax = 0.981Rint = 0.028
14963 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.35 e Å−3
3909 reflectionsΔρmin = −0.30 e Å−3
179 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
xyzUiso*/Ueq
O10.30643 (9)0.58032 (7)0.53563 (7)0.02056 (18)
O20.61515 (9)0.07478 (7)0.68475 (7)0.01987 (18)
O30.76423 (9)0.37484 (7)0.73708 (7)0.02157 (19)
O40.51710 (10)0.68753 (7)0.63602 (7)0.02266 (19)
N10.49890 (11)0.28280 (8)0.62667 (8)0.01539 (19)
N20.44571 (10)0.38868 (8)0.60104 (8)0.01477 (19)
C10.24246 (12)0.20271 (10)0.51384 (9)0.0164 (2)
H1A0.20100.27690.49370.020*
C20.14890 (13)0.10570 (10)0.47404 (10)0.0188 (2)
H2A0.04470.11470.42670.023*
C30.21166 (13)−0.00471 (10)0.50522 (10)0.0193 (2)
H3A0.1486−0.06950.47880.023*
C40.36743 (13)−0.02020 (10)0.57532 (10)0.0182 (2)
H4A0.4082−0.09460.59550.022*
C50.46119 (12)0.07678 (9)0.61481 (9)0.0155 (2)
C60.39815 (12)0.18864 (9)0.58381 (9)0.0149 (2)
C70.53715 (12)0.47955 (9)0.63721 (9)0.0154 (2)
C80.45682 (13)0.59306 (9)0.60453 (9)0.0160 (2)
C90.21993 (13)0.68756 (10)0.50635 (10)0.0211 (2)
H9A0.25280.74040.46630.025*
H9B0.23360.72540.57640.025*
C100.05623 (14)0.65495 (11)0.42841 (12)0.0297 (3)
H10A−0.00540.72370.40750.045*
H10B0.02550.60220.46890.045*
H10C0.04420.61820.35920.045*
C110.70375 (12)0.47143 (10)0.70367 (9)0.0172 (2)
C120.80061 (13)0.57743 (11)0.72907 (11)0.0232 (2)
H12A0.90490.55460.76330.035*
H12B0.78850.62670.78230.035*
H12C0.77060.61890.65790.035*
C130.68844 (14)−0.03669 (10)0.71190 (10)0.0215 (2)
H13A0.7964−0.02610.75430.032*
H13B0.6599−0.07820.64100.032*
H13C0.6581−0.08030.75860.032*
H1N10.5992 (19)0.2707 (14)0.6701 (14)0.037 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0175 (4)0.0120 (4)0.0265 (4)0.0022 (3)0.0067 (3)−0.0010 (3)
O20.0152 (4)0.0145 (4)0.0242 (4)0.0039 (3)0.0056 (3)0.0015 (3)
O30.0179 (4)0.0180 (4)0.0241 (4)0.0013 (3)0.0069 (3)0.0013 (3)
O40.0229 (4)0.0128 (4)0.0280 (4)−0.0026 (3)0.0095 (4)−0.0013 (3)
N10.0153 (4)0.0113 (4)0.0177 (4)0.0009 (4)0.0068 (4)0.0009 (3)
N20.0182 (4)0.0114 (4)0.0149 (4)0.0006 (3)0.0084 (4)0.0001 (3)
C10.0168 (5)0.0132 (5)0.0191 (5)0.0030 (4)0.0088 (4)0.0021 (4)
C20.0160 (5)0.0173 (5)0.0224 (5)−0.0001 (4)0.0092 (4)−0.0001 (4)
C30.0202 (5)0.0144 (5)0.0233 (5)−0.0034 (4)0.0108 (5)−0.0019 (4)
C40.0224 (6)0.0116 (5)0.0208 (5)0.0010 (4)0.0111 (4)0.0006 (4)
C50.0163 (5)0.0139 (5)0.0158 (5)0.0021 (4)0.0077 (4)0.0006 (4)
C60.0173 (5)0.0122 (5)0.0163 (5)−0.0005 (4)0.0092 (4)−0.0002 (4)
C70.0168 (5)0.0133 (5)0.0150 (5)−0.0002 (4)0.0071 (4)0.0002 (4)
C80.0182 (5)0.0140 (5)0.0158 (5)−0.0001 (4)0.0085 (4)0.0001 (4)
C90.0210 (6)0.0122 (5)0.0272 (6)0.0038 (4)0.0100 (5)−0.0004 (4)
C100.0205 (6)0.0212 (6)0.0420 (7)0.0040 (5)0.0116 (6)0.0000 (5)
C110.0170 (5)0.0177 (5)0.0152 (5)−0.0010 (4)0.0067 (4)−0.0007 (4)
C120.0184 (5)0.0204 (6)0.0264 (6)−0.0038 (5)0.0078 (5)0.0001 (5)
C130.0215 (6)0.0192 (6)0.0243 (6)0.0081 (5)0.0119 (5)0.0052 (4)
Geometric parameters (Å, º) top
O1—C81.3430 (14)C4—H4A0.9300
O1—C91.4510 (13)C5—C61.4041 (15)
O2—C51.3660 (13)C7—C111.4732 (16)
O2—C131.4355 (13)C7—C81.4852 (15)
O3—C111.2393 (13)C9—C101.5053 (17)
O4—C81.2143 (13)C9—H9A0.9700
N1—N21.3064 (12)C9—H9B0.9700
N1—C61.4019 (14)C10—H10A0.9600
N1—H1N10.898 (17)C10—H10B0.9600
N2—C71.3201 (14)C10—H10C0.9600
C1—C21.3885 (15)C11—C121.4967 (16)
C1—C61.3896 (15)C12—H12A0.9600
C1—H1A0.9300C12—H12B0.9600
C2—C31.3880 (16)C12—H12C0.9600
C2—H2A0.9300C13—H13A0.9600
C3—C41.3925 (16)C13—H13B0.9600
C3—H3A0.9300C13—H13C0.9600
C4—C51.3891 (15)
C8—O1—C9115.03 (9)O1—C8—C7112.17 (9)
C5—O2—C13117.52 (9)O1—C9—C10106.76 (9)
N2—N1—C6119.32 (9)O1—C9—H9A110.4
N2—N1—H1N1120.1 (11)C10—C9—H9A110.4
C6—N1—H1N1120.6 (11)O1—C9—H9B110.4
N1—N2—C7121.15 (9)C10—C9—H9B110.4
C2—C1—C6119.85 (10)H9A—C9—H9B108.6
C2—C1—H1A120.1C9—C10—H10A109.5
C6—C1—H1A120.1C9—C10—H10B109.5
C3—C2—C1119.66 (10)H10A—C10—H10B109.5
C3—C2—H2A120.2C9—C10—H10C109.5
C1—C2—H2A120.2H10A—C10—H10C109.5
C2—C3—C4121.15 (10)H10B—C10—H10C109.5
C2—C3—H3A119.4O3—C11—C7119.26 (10)
C4—C3—H3A119.4O3—C11—C12119.68 (10)
C5—C4—C3119.23 (10)C7—C11—C12121.05 (10)
C5—C4—H4A120.4C11—C12—H12A109.5
C3—C4—H4A120.4C11—C12—H12B109.5
O2—C5—C4125.60 (10)H12A—C12—H12B109.5
O2—C5—C6114.58 (9)C11—C12—H12C109.5
C4—C5—C6119.81 (10)H12A—C12—H12C109.5
C1—C6—N1122.73 (10)H12B—C12—H12C109.5
C1—C6—C5120.29 (10)O2—C13—H13A109.5
N1—C6—C5116.98 (9)O2—C13—H13B109.5
N2—C7—C11124.05 (10)H13A—C13—H13B109.5
N2—C7—C8113.80 (9)O2—C13—H13C109.5
C11—C7—C8122.15 (10)H13A—C13—H13C109.5
O4—C8—O1122.70 (10)H13B—C13—H13C109.5
O4—C8—C7125.13 (10)
C6—N1—N2—C7−178.24 (9)C4—C5—C6—N1179.90 (10)
C6—C1—C2—C30.46 (16)N1—N2—C7—C112.76 (16)
C1—C2—C3—C4−0.43 (17)N1—N2—C7—C8−177.39 (9)
C2—C3—C4—C50.18 (17)C9—O1—C8—O4−3.10 (15)
C13—O2—C5—C45.71 (15)C9—O1—C8—C7176.32 (9)
C13—O2—C5—C6−174.96 (9)N2—C7—C8—O4174.02 (10)
C3—C4—C5—O2179.33 (10)C11—C7—C8—O4−6.12 (17)
C3—C4—C5—C60.03 (16)N2—C7—C8—O1−5.37 (13)
C2—C1—C6—N1179.86 (10)C11—C7—C8—O1174.48 (9)
C2—C1—C6—C5−0.26 (15)C8—O1—C9—C10179.35 (10)
N2—N1—C6—C10.42 (15)N2—C7—C11—O3−6.31 (16)
N2—N1—C6—C5−179.46 (9)C8—C7—C11—O3173.85 (10)
O2—C5—C6—C1−179.36 (9)N2—C7—C11—C12172.36 (10)
C4—C5—C6—C10.01 (15)C8—C7—C11—C12−7.48 (15)
O2—C5—C6—N10.53 (13)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O30.90 (2)1.886 (19)2.5715 (15)131.6 (14)
C13—H13C···N2i0.962.583.4835 (18)156
C12—H12B···Cg1ii0.962.923.6620 (15)135
C13—H13B···Cg1iii0.962.663.4887 (14)145
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, y+1/2, −z+3/2; (iii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formulaC13H16N2O4
Mr264.28
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)10.1885 (4), 11.4967 (4), 13.2492 (5)
β (°) 120.003 (3)
V (Å3)1343.97 (9)
Z4
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.75 × 0.27 × 0.20
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.931, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections		14963, 3909, 3123
Rint0.028
(sin θ/λ)max (Å−1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.116, 1.03
No. of reflections3909
No. of parameters179
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.35, −0.30

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

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O30.90 (2)1.886 (19)2.5715 (15)131.6 (14)
C13—H13C···N2i0.962.58003.4835 (18)156
C12—H12B···Cg1ii0.962.923.6620 (15)135
C13—H13B···Cg1iii0.962.663.4887 (14)145
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, y+1/2, −z+3/2; (iii) −x+1, −y, −z+1.
 

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

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ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2571
https://doi.org/10.1107/S1600536811034854
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