supplementary materials


bv2227 scheme

Acta Cryst. (2013). E69, o1752    [ doi:10.1107/S160053681302998X ]

4-(3-Fluoro-4-methyl­anilino)-2-methyl­idene-4-oxo­butanoic acid

P. S. Nayak, B. Narayana, J. P. Jasinski, H. S. Yathirajan and M. Kaur

Abstract top

The title compound, C12H12FNO3, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. The dihedral angle between the mean planes of the 3-fluoro-4-methyl­phenyl ring and the oxo­amine group is 25.7 (7)° in mol­ecule A and 71.3 (7)° in mol­ecule B, while the mean plane of the 2-methyl­idene-4-oxo­butanoic acid group is twisted by 76.2 (1)° from that of the oxo­amine group in mol­ecule A and by 76.2 (4)° in mol­ecule B. In the crystal, N-H...O and O-H...O hydrogen bonds [the latter forming an R22(8) graph-set motif] link the mol­ecules into a two-dimensional network parallel to the ac plane.

Comment top

Itaconic anhydride (ITA) is a monomer obtained from renewable resources. Copolymers containing both hydrophilic and hydrophobic segments are drawing considerable attention because of their possible use in biological systems. N-Substituted itaconamic acids are strongly amphiphilic molecules. Itaconic anhydride is more reactive than maleic anhydride and is an alternative monomer for introducing polar functionality into polymers (Oishi, 1980; Urzua et al., 1998). The basic skeleton of itaconic anhydride is useful for the synthesis of various biodynamic cyclic derivatives such as imides (Shetgiri & Nayak, 2005), pyridazine (Katla et al., 2011), oxazepine (Hanoon, 2011) and oxobutanoic acid (Nayak et al., 2013) derivatives. Hence in view of the importance of anhydride derivatives, the crystal structure of the title compound, C12H12NO3F, (I), is reported here.

The title compound, (I), crystallizes with two independent molecules (A & B) in the asymmetric unit (Fig. 1). The dihedral angle between the mean planes of the 3-fluoro-4-methylphenyl ring and the oxo-amine group is 25.7 (7)° (A) and 71.3 (7)Å (B), while the mean plane of the 2-methylidene-4-oxobutanoic acid group is twisted by 76.2 (1)Å (A) and 76.2 (4)Å (B) from that of the oxo-amine group. In the crystal, N—H···O hydrogen bonds and O—H···O R22(8) graph set motif hydrogen bonds link the molecules into a 2-D network along the ac plane (Fig. 2) and influence crystal packing.

Related literature top

For properties of itaconic anhydride polymers, see: Oishi (1980); Urzua et al. (1998). For derivatives of itaconic anhydride, see: Katla et al. (2011); Shetgiri & Nayak (2005); Hanoon (2011); Nayak et al. (2013). For standard bond lengths, see: Allen et al. (1987).

Experimental top

Itaconic anhydride (0.112 g, 1 mmol) dissolved in a 30 ml acetone and it was stirred at ambient temperature and 3-fluoro-4-methyl aniline (0.125 g, 1 mmol) was added portion wise over 30 mins (Fig. 3) The mixture turned into yellow slurry. After stirring 1.5hrs, the slurry was filtered. The solid was washed with acetone and dried to give title compound (I). Single crystals were grown from methanol by the slow evaporation method and used as such for x-ray studies.(M.P.: 414-416 K).

Refinement top

All of the H atoms were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 0.93Å (CH), 0.97Å (CH2), 0.96Å (CH3), 0.82Å (OH) or 0.86Å (NH). Isotropic displacement parameters for these atoms were set to 1.2 (CH, CH2, NH) or 1.5 (CH3, OH) times Ueq of the parent atom. Idealised Me and tetrahedral OH refined as rotating groups.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. ORTEP drawing of (I), C12H12FNO3, showing the labeling scheme with two molecules (A & B) in the asymmetric unit and 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. Molecular packing for (I) viewed along the b axis. Dashed lines indicate N—H···O hydrogen bonds and O—H···O R22(8) graph set motif hydrogen bonds which link the molecules into a 2-D network along the ac plane. H atoms not involved in hydrogen bonding have been removed for clarity.
[Figure 3] Fig. 3. Synthesis scheme of (I).
4-(3-Fluoro-4-methylanilino)-2-methylidene-4-oxobutanoic acid top
Crystal data top
C12H12FNO3Z = 4
Mr = 237.23F(000) = 496
Triclinic, P1Dx = 1.442 Mg m3
a = 6.3368 (3) ÅMo Kα radiation, λ = 0.7107 Å
b = 8.2642 (4) ÅCell parameters from 3167 reflections
c = 21.0277 (11) Åθ = 3.3–32.7°
α = 84.057 (4)°µ = 0.12 mm1
β = 89.798 (4)°T = 173 K
γ = 86.062 (4)°Irregular, colourless
V = 1092.69 (9) Å30.38 × 0.32 × 0.16 mm
Data collection top
Agilent Xcalibur (Eos, Gemini)
diffractometer
7221 independent reflections
Radiation source: Enhance (Mo) X-ray Source4872 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 16.0416 pixels mm-1θmax = 32.8°, θmin = 3.3°
ω scansh = 99
Absorption correction: multi-scan
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)
k = 1112
Tmin = 0.673, Tmax = 1.000l = 3031
13094 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.081H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.221 w = 1/[σ2(Fo2) + (0.0895P)2 + 0.6971P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
7221 reflectionsΔρmax = 0.68 e Å3
327 parametersΔρmin = 0.28 e Å3
0 restraints
Crystal data top
C12H12FNO3γ = 86.062 (4)°
Mr = 237.23V = 1092.69 (9) Å3
Triclinic, P1Z = 4
a = 6.3368 (3) ÅMo Kα radiation
b = 8.2642 (4) ŵ = 0.12 mm1
c = 21.0277 (11) ÅT = 173 K
α = 84.057 (4)°0.38 × 0.32 × 0.16 mm
β = 89.798 (4)°
Data collection top
Agilent Xcalibur (Eos, Gemini)
diffractometer
7221 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)
4872 reflections with I > 2σ(I)
Tmin = 0.673, Tmax = 1.000Rint = 0.032
13094 measured reflectionsθmax = 32.8°
Refinement top
R[F2 > 2σ(F2)] = 0.081H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.221Δρmax = 0.68 e Å3
S = 1.06Δρmin = 0.28 e Å3
7221 reflectionsAbsolute structure: ?
327 parametersAbsolute structure parameter: ?
0 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F1A0.2264 (3)0.7138 (2)0.08603 (8)0.0598 (5)
O1A0.0578 (3)0.49102 (19)0.28774 (8)0.0317 (4)
O2A0.2598 (3)0.4663 (2)0.46934 (8)0.0326 (4)
H2A0.19780.50690.49730.049*
O3A0.0704 (2)0.3813 (2)0.44375 (8)0.0301 (3)
N1A0.1954 (3)0.3003 (2)0.26309 (9)0.0267 (4)
H1A0.24660.20260.27450.032*
C1A0.0240 (3)0.3514 (2)0.29537 (9)0.0223 (4)
C2A0.0635 (3)0.2194 (2)0.34215 (10)0.0253 (4)
H2AA0.13450.14430.31840.030*
H2AB0.05280.15840.36560.030*
C3A0.2160 (3)0.2886 (2)0.38861 (10)0.0239 (4)
C4A0.1221 (3)0.3827 (2)0.43641 (10)0.0236 (4)
C5A0.4195 (4)0.2636 (3)0.38952 (12)0.0324 (5)
H5AA0.518 (5)0.312 (4)0.4188 (14)0.038 (8)*
H5AB0.483 (5)0.204 (4)0.3585 (15)0.049 (9)*
C6A0.3022 (4)0.3877 (3)0.21259 (10)0.0266 (4)
C7A0.2073 (4)0.5190 (3)0.17415 (11)0.0310 (5)
H7A0.07010.55930.18200.037*
C8A0.3231 (4)0.5879 (3)0.12384 (11)0.0349 (5)
C9A0.5269 (4)0.5377 (3)0.10906 (12)0.0351 (5)
C10A0.6179 (4)0.4087 (3)0.14927 (13)0.0388 (6)
H10A0.75700.37160.14210.047*
C11A0.5091 (4)0.3328 (3)0.19983 (12)0.0337 (5)
H11A0.57430.24500.22530.040*
C12A0.6457 (5)0.6181 (4)0.05352 (13)0.0477 (7)
H12D0.55740.70580.03200.072*
H12E0.68430.53940.02420.072*
H12F0.77120.66020.06890.072*
F1B0.6414 (3)1.0662 (3)0.05324 (7)0.0555 (5)
O1B0.4220 (3)0.97672 (18)0.28923 (8)0.0288 (3)
O2B0.2374 (3)0.9727 (2)0.47086 (8)0.0350 (4)
H2B0.30501.01690.49650.053*
O3B0.5598 (2)0.8739 (2)0.44475 (8)0.0318 (4)
N1B0.6529 (3)0.7751 (2)0.26178 (9)0.0278 (4)
H1B0.69690.67430.26960.033*
C1B0.4934 (3)0.8347 (2)0.29677 (9)0.0214 (4)
C2B0.4038 (3)0.7091 (2)0.34588 (10)0.0248 (4)
H2BA0.32500.63480.32400.030*
H2BB0.51940.64600.36890.030*
C3B0.2614 (3)0.7880 (2)0.39254 (9)0.0234 (4)
C4B0.3671 (3)0.8823 (2)0.43834 (9)0.0233 (4)
C5B0.0546 (4)0.7733 (3)0.39513 (12)0.0321 (5)
H5BA0.030 (4)0.831 (3)0.4239 (12)0.029 (7)*
H5BB0.013 (5)0.715 (4)0.3643 (14)0.040 (8)*
C6B0.7520 (3)0.8736 (3)0.21197 (10)0.0260 (4)
C7B0.6465 (4)0.9236 (3)0.15526 (11)0.0304 (5)
H7B0.50930.89500.14890.036*
C8B0.7488 (4)1.0169 (3)0.10828 (11)0.0334 (5)
C9B0.9529 (4)1.0626 (3)0.11392 (11)0.0324 (5)
C10B1.0547 (4)1.0105 (3)0.17149 (11)0.0340 (5)
H10B1.19191.03940.17760.041*
C11B0.9578 (4)0.9164 (3)0.22030 (11)0.0308 (5)
H11B1.03010.88230.25830.037*
C12B1.0594 (5)1.1636 (4)0.06094 (13)0.0466 (7)
H12A1.17391.21560.07830.070*
H12B0.95881.24520.04100.070*
H12C1.11341.09450.02980.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F1A0.0641 (12)0.0530 (11)0.0554 (10)0.0053 (9)0.0081 (9)0.0204 (8)
O1A0.0349 (9)0.0197 (7)0.0393 (9)0.0029 (6)0.0068 (7)0.0007 (6)
O2A0.0261 (8)0.0356 (9)0.0384 (9)0.0011 (7)0.0009 (6)0.0149 (7)
O3A0.0242 (7)0.0300 (8)0.0383 (8)0.0041 (6)0.0013 (6)0.0117 (6)
N1A0.0288 (9)0.0183 (8)0.0324 (9)0.0005 (7)0.0039 (7)0.0003 (6)
C1A0.0234 (9)0.0184 (8)0.0256 (9)0.0015 (7)0.0016 (7)0.0034 (7)
C2A0.0303 (10)0.0161 (8)0.0302 (10)0.0043 (8)0.0005 (8)0.0038 (7)
C3A0.0266 (10)0.0186 (9)0.0265 (9)0.0041 (8)0.0001 (7)0.0007 (7)
C4A0.0237 (9)0.0189 (9)0.0283 (9)0.0047 (7)0.0022 (7)0.0013 (7)
C5A0.0280 (11)0.0319 (12)0.0382 (12)0.0088 (9)0.0004 (9)0.0038 (9)
C6A0.0293 (10)0.0216 (9)0.0297 (10)0.0051 (8)0.0033 (8)0.0043 (7)
C7A0.0321 (11)0.0267 (10)0.0339 (11)0.0020 (9)0.0025 (9)0.0014 (8)
C8A0.0440 (13)0.0257 (11)0.0343 (11)0.0052 (10)0.0028 (10)0.0013 (8)
C9A0.0435 (13)0.0271 (11)0.0371 (12)0.0141 (10)0.0096 (10)0.0065 (9)
C10A0.0326 (12)0.0346 (13)0.0500 (14)0.0060 (10)0.0117 (10)0.0057 (10)
C11A0.0297 (11)0.0284 (11)0.0419 (12)0.0001 (9)0.0045 (9)0.0008 (9)
C12A0.0585 (18)0.0435 (15)0.0430 (14)0.0181 (14)0.0184 (12)0.0042 (11)
F1B0.0517 (10)0.0758 (13)0.0364 (8)0.0110 (9)0.0070 (7)0.0112 (8)
O1B0.0296 (8)0.0180 (7)0.0375 (8)0.0016 (6)0.0067 (6)0.0003 (6)
O2B0.0248 (8)0.0406 (10)0.0422 (9)0.0002 (7)0.0010 (6)0.0179 (7)
O3B0.0226 (7)0.0340 (9)0.0409 (9)0.0035 (7)0.0012 (6)0.0128 (7)
N1B0.0279 (9)0.0180 (8)0.0365 (9)0.0020 (7)0.0068 (7)0.0007 (7)
C1B0.0204 (9)0.0186 (8)0.0257 (9)0.0022 (7)0.0005 (7)0.0030 (7)
C2B0.0285 (10)0.0147 (8)0.0315 (10)0.0045 (7)0.0014 (8)0.0022 (7)
C3B0.0253 (9)0.0186 (9)0.0261 (9)0.0044 (7)0.0011 (7)0.0009 (7)
C4B0.0225 (9)0.0205 (9)0.0266 (9)0.0030 (7)0.0024 (7)0.0009 (7)
C5B0.0267 (11)0.0346 (12)0.0347 (11)0.0075 (9)0.0008 (9)0.0011 (9)
C6B0.0254 (10)0.0198 (9)0.0330 (10)0.0007 (8)0.0066 (8)0.0039 (7)
C7B0.0242 (10)0.0325 (11)0.0355 (11)0.0059 (9)0.0028 (8)0.0062 (9)
C8B0.0347 (12)0.0347 (12)0.0304 (11)0.0019 (10)0.0005 (9)0.0022 (9)
C9B0.0342 (12)0.0278 (11)0.0362 (11)0.0049 (9)0.0100 (9)0.0066 (9)
C10B0.0282 (11)0.0374 (13)0.0384 (12)0.0102 (10)0.0048 (9)0.0085 (9)
C11B0.0263 (10)0.0321 (11)0.0345 (11)0.0037 (9)0.0001 (8)0.0041 (9)
C12B0.0529 (16)0.0426 (15)0.0451 (14)0.0156 (13)0.0182 (12)0.0012 (11)
Geometric parameters (Å, º) top
F1A—C8A1.355 (3)F1B—C8B1.356 (3)
O1A—C1A1.228 (2)O1B—C1B1.223 (2)
O2A—H2A0.8200O2B—H2B0.8200
O2A—C4A1.315 (2)O2B—C4B1.311 (2)
O3A—C4A1.229 (3)O3B—C4B1.225 (2)
N1A—H1A0.8600N1B—H1B0.8600
N1A—C1A1.345 (3)N1B—C1B1.344 (2)
N1A—C6A1.418 (3)N1B—C6B1.429 (3)
C1A—C2A1.524 (3)C1B—C2B1.523 (3)
C2A—H2AA0.9700C2B—H2BA0.9700
C2A—H2AB0.9700C2B—H2BB0.9700
C2A—C3A1.500 (3)C2B—C3B1.499 (3)
C3A—C4A1.483 (3)C3B—C4B1.488 (3)
C3A—C5A1.320 (3)C3B—C5B1.325 (3)
C5A—H5AA0.97 (3)C5B—H5BA0.95 (3)
C5A—H5AB0.97 (3)C5B—H5BB0.96 (3)
C6A—C7A1.387 (3)C6B—C7B1.380 (3)
C6A—C11A1.392 (3)C6B—C11B1.391 (3)
C7A—H7A0.9300C7B—H7B0.9300
C7A—C8A1.382 (3)C7B—C8B1.377 (3)
C8A—C9A1.373 (4)C8B—C9B1.381 (3)
C9A—C10A1.385 (4)C9B—C10B1.388 (3)
C9A—C12A1.508 (3)C9B—C12B1.508 (3)
C10A—H10A0.9300C10B—H10B0.9300
C10A—C11A1.384 (3)C10B—C11B1.389 (3)
C11A—H11A0.9300C11B—H11B0.9300
C12A—H12D0.9600C12B—H12A0.9600
C12A—H12E0.9600C12B—H12B0.9600
C12A—H12F0.9600C12B—H12C0.9600
C4A—O2A—H2A109.5C4B—O2B—H2B109.5
C1A—N1A—H1A116.0C1B—N1B—H1B118.9
C1A—N1A—C6A128.04 (17)C1B—N1B—C6B122.27 (17)
C6A—N1A—H1A116.0C6B—N1B—H1B118.9
O1A—C1A—N1A123.59 (19)O1B—C1B—N1B123.28 (18)
O1A—C1A—C2A122.32 (18)O1B—C1B—C2B122.36 (17)
N1A—C1A—C2A114.09 (17)N1B—C1B—C2B114.34 (17)
C1A—C2A—H2AA109.1C1B—C2B—H2BA109.3
C1A—C2A—H2AB109.1C1B—C2B—H2BB109.3
H2AA—C2A—H2AB107.9H2BA—C2B—H2BB107.9
C3A—C2A—C1A112.28 (16)C3B—C2B—C1B111.76 (16)
C3A—C2A—H2AA109.1C3B—C2B—H2BA109.3
C3A—C2A—H2AB109.1C3B—C2B—H2BB109.3
C4A—C3A—C2A115.60 (18)C4B—C3B—C2B115.88 (18)
C5A—C3A—C2A123.3 (2)C5B—C3B—C2B123.4 (2)
C5A—C3A—C4A121.1 (2)C5B—C3B—C4B120.7 (2)
O2A—C4A—C3A114.93 (18)O2B—C4B—C3B114.48 (18)
O3A—C4A—O2A123.6 (2)O3B—C4B—O2B123.6 (2)
O3A—C4A—C3A121.48 (19)O3B—C4B—C3B121.93 (18)
C3A—C5A—H5AA122.7 (18)C3B—C5B—H5BA119.9 (17)
C3A—C5A—H5AB122.1 (19)C3B—C5B—H5BB120.1 (18)
H5AA—C5A—H5AB115 (3)H5BA—C5B—H5BB120 (2)
C7A—C6A—N1A123.2 (2)C7B—C6B—N1B120.5 (2)
C7A—C6A—C11A119.2 (2)C7B—C6B—C11B119.9 (2)
C11A—C6A—N1A117.53 (19)C11B—C6B—N1B119.6 (2)
C6A—C7A—H7A121.1C6B—C7B—H7B120.7
C8A—C7A—C6A117.9 (2)C8B—C7B—C6B118.5 (2)
C8A—C7A—H7A121.1C8B—C7B—H7B120.7
F1A—C8A—C7A117.0 (2)F1B—C8B—C7B117.6 (2)
F1A—C8A—C9A117.8 (2)F1B—C8B—C9B118.4 (2)
C9A—C8A—C7A125.1 (2)C7B—C8B—C9B124.0 (2)
C8A—C9A—C10A115.3 (2)C8B—C9B—C10B116.0 (2)
C8A—C9A—C12A122.7 (2)C8B—C9B—C12B122.2 (2)
C10A—C9A—C12A121.9 (2)C10B—C9B—C12B121.8 (2)
C9A—C10A—H10A118.9C9B—C10B—H10B119.0
C11A—C10A—C9A122.3 (2)C9B—C10B—C11B122.0 (2)
C11A—C10A—H10A118.9C11B—C10B—H10B119.0
C6A—C11A—H11A119.9C6B—C11B—H11B120.2
C10A—C11A—C6A120.1 (2)C10B—C11B—C6B119.5 (2)
C10A—C11A—H11A119.9C10B—C11B—H11B120.2
C9A—C12A—H12D109.5C9B—C12B—H12A109.5
C9A—C12A—H12E109.5C9B—C12B—H12B109.5
C9A—C12A—H12F109.5C9B—C12B—H12C109.5
H12D—C12A—H12E109.5H12A—C12B—H12B109.5
H12D—C12A—H12F109.5H12A—C12B—H12C109.5
H12E—C12A—H12F109.5H12B—C12B—H12C109.5
F1A—C8A—C9A—C10A180.0 (2)F1B—C8B—C9B—C10B179.3 (2)
F1A—C8A—C9A—C12A0.7 (4)F1B—C8B—C9B—C12B0.5 (4)
O1A—C1A—C2A—C3A15.6 (3)O1B—C1B—C2B—C3B13.9 (3)
N1A—C1A—C2A—C3A165.26 (18)N1B—C1B—C2B—C3B167.55 (19)
N1A—C6A—C7A—C8A175.9 (2)N1B—C6B—C7B—C8B179.3 (2)
N1A—C6A—C11A—C10A177.1 (2)N1B—C6B—C11B—C10B179.2 (2)
C1A—N1A—C6A—C7A22.6 (4)C1B—N1B—C6B—C7B71.6 (3)
C1A—N1A—C6A—C11A160.4 (2)C1B—N1B—C6B—C11B109.7 (2)
C1A—C2A—C3A—C4A69.2 (2)C1B—C2B—C3B—C4B69.6 (2)
C1A—C2A—C3A—C5A113.4 (2)C1B—C2B—C3B—C5B112.1 (2)
C2A—C3A—C4A—O2A168.57 (17)C2B—C3B—C4B—O2B168.70 (17)
C2A—C3A—C4A—O3A11.3 (3)C2B—C3B—C4B—O3B11.7 (3)
C5A—C3A—C4A—O2A14.0 (3)C5B—C3B—C4B—O2B13.0 (3)
C5A—C3A—C4A—O3A166.2 (2)C5B—C3B—C4B—O3B166.6 (2)
C6A—N1A—C1A—O1A5.3 (4)C6B—N1B—C1B—O1B0.6 (3)
C6A—N1A—C1A—C2A173.9 (2)C6B—N1B—C1B—C2B177.90 (19)
C6A—C7A—C8A—F1A178.7 (2)C6B—C7B—C8B—F1B179.3 (2)
C6A—C7A—C8A—C9A0.7 (4)C6B—C7B—C8B—C9B0.8 (4)
C7A—C6A—C11A—C10A0.1 (4)C7B—C6B—C11B—C10B0.5 (3)
C7A—C8A—C9A—C10A0.6 (4)C7B—C8B—C9B—C10B0.7 (4)
C7A—C8A—C9A—C12A179.9 (3)C7B—C8B—C9B—C12B179.4 (2)
C8A—C9A—C10A—C11A1.6 (4)C8B—C9B—C10B—C11B0.6 (4)
C9A—C10A—C11A—C6A1.3 (4)C9B—C10B—C11B—C6B0.6 (4)
C11A—C6A—C7A—C8A1.0 (4)C11B—C6B—C7B—C8B0.6 (3)
C12A—C9A—C10A—C11A179.1 (3)C12B—C9B—C10B—C11B179.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H2A···O3Ai0.821.842.658 (2)174
O2B—H2B···O3Bii0.821.852.667 (2)176
N1A—H1A···O1Biii0.862.102.948 (2)168
N1B—H1B···O1Aiv0.862.102.884 (2)151
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+2, z+1; (iii) x, y1, z; (iv) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H2A···O3Ai0.821.842.658 (2)174.0
O2B—H2B···O3Bii0.821.852.667 (2)175.9
N1A—H1A···O1Biii0.862.102.948 (2)168.2
N1B—H1B···O1Aiv0.862.102.884 (2)151.2
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+2, z+1; (iii) x, y1, z; (iv) x+1, y, z.
Acknowledgements top

BN thanks the UGC for a BSR one-time grant for the purchase of chemicals and the DST–PURSE for financial assistance. HSY thanks the University of Mysore for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

references
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