research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Ethyl 2-amino-1-(4-fluoro­phen­yl)-5-oxo-4,5-di­hydro-1H-pyrrole-3-carboxyl­ate: crystal structure and Hirshfeld surface analysis

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aDepartment of Physics, V.V. Nagar, Anand, Gujarat, India, b103, X-Ray Lab, Department of Physics, V.V. Nagar, Anand, Gujarat, India, and cOrganic Synthesis Laboratory, M. G. Science Institute, Ahmedabad, Gujarat, India
*Correspondence e-mail: chintan.jotaniya@gmail.com

Edited by P. Dastidar, Indian Association for the Cultivation of Science, India (Received 23 June 2017; accepted 8 August 2017; online 11 August 2017)

In the title mol­ecule, C12H13FN2O3, the central pyrrole ring makes a dihedral angle of 9.2 (3)° with the eth­oxy carbonyl moiety whereas the fluoro­phenyl ring is rotated by 67.6 (2)° from the pyrrole ring. Supra­molecular aggregation is due to off-centric ππ stacking inter­actions involving screw-related pairs of mol­ecules, which are further connected by N—H⋯O and C—H⋯O inter­actions, forming a sinusoidal pattern along the [001] direction on the bc plane. Three-dimensional Hirshfeld surface analysis and two-dimensional fingerprint plots confirm the contributions of these inter­actions.

1. Chemical context

Pyrrole, an electron-rich five-membered unsaturated ring, and its derivatives are widely used as inter­mediates in the synthesis of organic compounds, medicines, pharmaceuticals, agrochemicals, perfumes etc. Its derivatives possess a broad spectrum of biological activities. Substitution by a halogen (Cl, Br, F, I) is known to increase the activities of drug mol­ecules and this group of mol­ecules inter­act with receptors via halogen bonding. Organofluorine compounds display a variety of pharmacological and agro-chemical properties. Specific halogen-bonding inter­actions are responsible for the supra­molecular architecture in halogen-substituted heterocycles. Bearing in mind the importance of pyrrole and the role of halogens, we have synthesized a series of halogen-substituted pyrrole derivatives. Bromo and meth­oxy derivatives of the title mol­ecule have been reported earlier (Patel et al., 2012[Patel, B. D., Patel, U. H. & Shah, D. A. (2012). Int. J. Appl. Sci. Eng. Res. 1, 6, 755-762.], 2013[Patel, U. H., Patel, B. D. & Shah, D. A. (2013). Int. J. Appl. Sci. Eng. Res. 2, 170-180.]). As a continuation of these studies, the title mol­ecule, with fluorine as one of the substituents, was synthesized and characterized crystallographically and by Hirshfeld surface analysis.

[Scheme 1]

2. Structural commentary

In the title compound, Fig. 1[link], the F atom is displaced by 0.014 (3) Å from the phenyl ring, facilitating it in to take part in a number of inter­molecular inter­actions. The heterocyclic five-membered pyrrole ring is essentially planar with a maximum displacement of 0.022 (4) Å for atom C3 from its mean plane. The fluoro­phenyl ring forms a dihedral angle of 67.6 (2)° whereas the mean plane of eth­oxy carbonyl tail is inclined at 9.2 (3)° to the central pyrrole ring. The terminal eth­oxy carbonyl chain adopts a zigzag extended conformation, as is usually observed in analogous derivatives, with the carbonyl oxygen atom O19 on the same side as the methyl carbon atom C17 [C17—O16—C15—O19 = 5.0 (7)°] and the eth­oxy carbon atom C18 in a trans [C15—O16—C17—C18 = 144.6 (5)°] conformation with respect to the pyrrole ring. Bond lengths in the phenyl ring vary from 1.365 (6) to 1.385 (6) Å and the endocyclic angle varies from 118.0 (4) to 122.9 (4)° with an average value of 120.4 (4)°, which coincides exactly with the theoretical value 120° for sp2 hybridization.

[Figure 1]
Figure 1
ORTEP view of the title mol­ecule with the atom-labelling scheme and displacement ellipsoids drawn at the 50% probability level.

The intra­molecular N6—H61⋯O19 hydrogen bond involving the carbonyl oxygen atom O19 leads to the formation of a pseudo-six-membered ring with an S(6) graph-set motif.

3. Supra­molecular features

In the crystal, two pairs of screw-related mol­ecules are held together by off-centric ππ stacking inter­actions involving the pyrrole ring and the phenyl ring of a screw-related mol­ecule (−x, [{1\over 2}] + y, [{1\over 2}] − z) [centroid–centroid distance = 4.179 (2) Å, slippage = 2.036 Å, dihedral angle between planes = 5.9 (2)°], forming chains along [010]. The structure contains infinite zigzag chains of screw-related mol­ecules, forming a sinusoidal patterns along [001] on the bc plane as shown in Fig. 2[link].

[Figure 2]
Figure 2
View of the packing showing ππ stacking inter­actions and N—H⋯O and C—H⋯O hydrogen bonds (dashed lines) in the bc plane.

The molecular packing features N—H⋯O interactions, which lead to the formation of chains alon [001], and ππ stacking interactions, which link the molecules along [010]. In addition, C—H1⋯O inter­actions stack the molecules along [100] (Fig. 2[link], Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N6—H61⋯O19 0.86 2.2400 2.806 (4) 123
N6—H62⋯O7i 0.86 2.2100 2.970 (4) 147
C13—H13⋯O7ii 0.93 2.6000 3.320 (5) 135
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x-1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

4. Analysis of the Hirshfeld Surfaces

Crystal Explorer 3.1 (Wolff et al., 2012[Wolff, S. K., Grimwood, D. J., McKinnon, J. J., Turner, M. J., Jayatilaka, D. & Spackman, M. A. (2012). Crystal Explorer. The University of Western Australia.]) was used to generate Hirshfeld surfaces mapped over dnorm, de and electrostatic potential for the title compound. The electrostatic potentials were calculated using TONTO (Spackman et al., 2008[Spackman, M. A., McKinnon, J. J. & Jayatilaka, D. (2008). CrystEngComm, 10, 377-388.]; Jayatilaka et al., 2005[Jayatilaka, D., Grimwood, D. J., Lee, A., Lemay, A., Russel, A. J., Taylor, C., Wolff, S. K., Cassam-Chenai, P. & Whitton, A. (2005). TONTO - A System for Computational Chemistry. Available at: https://hirshfeldsurface.net/]) as integrated in Crystal Explorer and are mapped on Hirshfeld surfaces using the STO-3G basis set at the Hartree–Fock level of theory over a range ±0.10 au as shown in Fig. 3[link]. The positive electrostatic potential (blue region) over the surface indicates a hydrogen-bond donor, whereas the hydrogen-bond acceptors are represented by negative electrostatic potential (red region). The contact distances di and de from the Hirshfeld surface to the nearest atom inside and outside, respectively, enables the analysis of the inter­molecular inter­actions through the mapping of dnorm.

[Figure 3]
Figure 3
View of the Hirshfeld surface mapped over the calculated electrostatic potential for the title compound. The red and blue regions represent negative and positive electrostatic potentials, respectively.

A view of the Hirshfeld surface mapped over dnorm, shape-index and curvedness for the title compound are shown in Fig. 4[link]. Hirshfeld surfaces marked with red regions in dnorm near atoms O7, O19, N6, H62 and H10 reveal the active participation of the respective atoms in inter­molecular inter­actions. The occurrence of N—H⋯O and C—H⋯O inter­actions is confirmed by analysis of the Hirshfeld surface. N6—H62⋯O19 inter­actions are shown on the Hirshfeld surface marked with bright-red dotted lines in Fig. 5[link]. Yellow dotted lines mapped on the dnorm Hirshfeld surface in Fig. 6[link] reveal the presence of C13—H13⋯O7 and C17—H172⋯O19 inter­actions.

[Figure 4]
Figure 4
View of the Hirshfeld surface mapped over (a) dnorm, (b) shape-index and (c) curvedness.
[Figure 5]
Figure 5
dnorm mapped on the Hirshfeld surface for visualizing the N—H⋯O inter­molecular inter­actions of the title compound. Red dotted lines represent hydrogen bonds.
[Figure 6]
Figure 6
dnorm mapped on the Hirshfeld surface for visualizing the C—H⋯O inter­molecular inter­actions (yellow dotted lines) of the title compound.

The two-dimensional fingerprint plots (Rohl et al., 2008[Rohl, A. L., Moret, M., Kaminsky, W., Claborn, K., McKinnon, J. J. & Kahr, B. (2008). Cryst. Growth Des. 8, 4517-4525.]) for the title mol­ecule are shown in Fig. 7[link]. The inter atomic H⋯H contacts appear as scattered points over the larger part of the plot along with one distinct spike with the highest contribution within the Hirshfeld surface of 44.9% (Fig. 7[link]b), followed by 20.8% for O⋯H/H⋯O contacts, which appear as pairs of adjacent spikes having almost same length. The contributions of H⋯F/F⋯H and C⋯H/H⋯C contacts are 12.8 and 10.4%, respectively. The contribution of C⋯C contacts, i.e. 3.0%, shows the ππ stacking inter­actions in the compound have a relatively smaller contribution. Apart from these, C⋯O/O⋯C, C⋯N/N⋯C, O⋯F/F⋯O, O⋯N/N⋯O and C⋯F/F⋯C contacts are found, as summarized in Table 2[link].

Table 2
Summary of various contacts and their percentage contributions to the Hirshfeld surface

Type of contact Contribution
H⋯H 44.9
O⋯H/H⋯O 20.8
H⋯F/F⋯H 12.8
C⋯H/H⋯C 10.4
C⋯C 3.4
C⋯O/O⋯C 3.0
C⋯N/N⋯C 1.8
O⋯F/F⋯O 1.0
O⋯N/N⋯O 0.6
C⋯F/F⋯C 0.5
[Figure 7]
Figure 7
The two-dimensional fingerprint plots for the title compound, showing contributions from different contacts, (a) all, (b) H⋯H, (c) O⋯H/H⋯O, (d) H⋯F/F⋯H, (e) C⋯H/H⋯C and (f) C⋯C, respectively.

5. Database survey

Two analogous structures, 2-amino-1(4-bromo­phen­yl)-5-oxo-4,5-di­hydro-1H-pyrrole-3-carb­oxy­lic acid ethyl ester (Patel et al., 2012[Patel, B. D., Patel, U. H. & Shah, D. A. (2012). Int. J. Appl. Sci. Eng. Res. 1, 6, 755-762.]) and 2-amino-1-(4-meth­oxy­phen­yl)-5-oxo-4,5-di­hydro-1H-pyrrole-3-carb­oxy­lic acid ethyl ester (Patel et al., 2013[Patel, U. H., Patel, B. D. & Shah, D. A. (2013). Int. J. Appl. Sci. Eng. Res. 2, 170-180.]), in which the fluoro­phenyl ring of the title compound is replaced by a bromo or meth­oxy­phenyl ring, are reported in the Cambridge Structural Database (Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]).

6. Synthesis and crystallization

In a 50 ml flat-bottom flask, a mixture of dry toluene (15 ml), potassium hydroxide (0.012 mol, 0.672 g) and 18-crown-6 (0.0005 mol, 0.132 g) were prepared. Ethyl cyano­acetate (0.006 mol, 0.6787 g) was then added to this stirred mixture, followed by the portionwise addition of N-(4-fluoro­phen­yl)-2-chloro­acetamide (0.005 mol, 1.2425 g) after 5 min. The stirring was continued until the chloro­acetamide derivative had been consumed (20 min), monitored TLC (hexa­ne:ethyl acetate 7:3). On completion of the reaction, water (25 ml) was added to the reaction mixture and stirring continued for a further 5 min. This was then taken into a separating funnel and the aqueous phase was neutralized with glacial acetic acid (pH = 7). The phases were separated and the aqueous phase extracted with toluene (10 ml). The combined organic layers were dried over magnesium sulfate and the toluene removed in vacuo to obtain a solid product. The crude product was crystallized from ethanol to obtain 1.42 g (87% yield) of 2-amino-1-(4-fluoro­phen­yl)-oxo-4,5-di­hydro-1H-pyrrole-3-carb­oxy­lic acid ethyl ester, m.p. 783.24 K. It is more or less soluble in different solvents such as benzene, ethanol, DMF, DMSO, CH2CL2, CHCl3, ethyl acetate but diffraction quality crystal could be grown by the slow evaporation method at room temperature from ethyl acetate only after repeated trials.

7. Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 3[link]. Carbon-bound H atoms were placed in their calculated positions (C—H = 0.93–0.97 Å) and are included in the refinement in the riding-model approximation, with Uiso(H) set to 1.2Ueq(C).

Table 3
Experimental details

Crystal data
Chemical formula C13H13FN2O3
Mr 264.25
Crystal system, space group Orthorhombic, P212121
Temperature (K) 273
a, b, c (Å) 5.5357 (16), 8.548 (2), 27.026 (7)
V3) 1278.9 (6)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.11
Crystal size (mm) 0.7 × 0.3 × 0.2
 
Data collection
Diffractometer Bruker SMART APEX CCD
Absorption correction Multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.962, 0.979
No. of measured, independent and observed [I > 2Σ(I)] reflections 7696, 2975, 2322
Rint 0.032
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.075, 0.148, 1.18
No. of reflections 2975
No. of parameters 173
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.23, −0.24
Computer programs: APEX2 and SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2013 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

Ethyl 2-amino-1-(4-fluorophenyl)-5-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate: top
Crystal data top
C13H13FN2O3Dx = 1.372 Mg m3
Mr = 264.25Melting point: 783.39 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 7696 reflections
a = 5.5357 (16) Åθ = 1.5–28.2°
b = 8.548 (2) ŵ = 0.11 mm1
c = 27.026 (7) ÅT = 273 K
V = 1278.9 (6) Å3Transparent, colourless
Z = 40.7 × 0.3 × 0.2 mm
F(000) = 552
Data collection top
Bruker SMART APEX CCD
diffractometer
2975 independent reflections
Radiation source: SEALED TUBE2322 reflections with I > 2Σ(I)
Graphite monochromatorRint = 0.032
ω–2θ scanθmax = 28.2°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 76
Tmin = 0.962, Tmax = 0.979k = 1011
7696 measured reflectionsl = 3432
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.075H-atom parameters constrained
wR(F2) = 0.148Weighting scheme based on measured s.u.'s
S = 1.18(Δ/σ)max = 0.006
2975 reflectionsΔρmax = 0.23 e Å3
173 parametersΔρmin = 0.24 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F140.0103 (6)0.1908 (3)0.41628 (9)0.0777 (11)
O70.3466 (5)0.3868 (3)0.20473 (10)0.0501 (9)
O160.0782 (6)0.1173 (4)0.04855 (10)0.0675 (11)
O190.3634 (6)0.0024 (4)0.09592 (11)0.0665 (11)
N10.0226 (5)0.2174 (3)0.21258 (11)0.0380 (9)
N60.3131 (6)0.0484 (3)0.19821 (11)0.0449 (10)
C20.1947 (7)0.3016 (4)0.18607 (14)0.0402 (11)
C30.1510 (8)0.2676 (4)0.13223 (14)0.0457 (12)
C40.0711 (7)0.1663 (4)0.13244 (13)0.0403 (11)
C50.1342 (6)0.1388 (4)0.18000 (13)0.0351 (11)
C80.0114 (6)0.2105 (4)0.26584 (12)0.0345 (11)
C90.1786 (7)0.2794 (4)0.29063 (14)0.0420 (12)
C100.1843 (8)0.2732 (5)0.34181 (15)0.0503 (12)
C110.0017 (8)0.1985 (5)0.36617 (14)0.0490 (14)
C120.1879 (8)0.1282 (5)0.34218 (15)0.0527 (16)
C130.1941 (7)0.1362 (4)0.29129 (14)0.0437 (12)
C150.1869 (8)0.0873 (5)0.09193 (14)0.0473 (12)
C170.1672 (12)0.0330 (8)0.00528 (17)0.094 (2)
C180.0234 (14)0.0020 (10)0.0268 (2)0.134 (4)
H90.301240.329390.273210.0506*
H100.310420.319120.359290.0606*
H120.308510.076760.359750.0630*
H130.321960.091260.274060.0526*
H310.123080.363420.113860.0551*
H320.287130.212770.117770.0551*
H610.406560.001810.178370.0539*
H620.333750.041100.229670.0539*
H1710.285990.096430.011850.1126*
H1720.245160.063130.015730.1126*
H1810.037410.057870.054970.2012*
H1820.098460.093350.037580.2012*
H1830.140190.065450.009860.2012*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F140.087 (2)0.109 (2)0.0371 (14)0.006 (2)0.0004 (14)0.0091 (13)
O70.0503 (16)0.0487 (14)0.0512 (16)0.0128 (15)0.0068 (14)0.0092 (12)
O160.071 (2)0.098 (2)0.0334 (15)0.011 (2)0.0043 (14)0.0106 (16)
O190.064 (2)0.084 (2)0.0516 (18)0.017 (2)0.0054 (15)0.0114 (16)
N10.0386 (17)0.0400 (15)0.0355 (17)0.0025 (15)0.0067 (14)0.0008 (13)
N60.0452 (19)0.0525 (18)0.0371 (17)0.0057 (17)0.0003 (15)0.0050 (14)
C20.046 (2)0.0337 (18)0.041 (2)0.0002 (19)0.0057 (19)0.0048 (16)
C30.050 (2)0.043 (2)0.044 (2)0.001 (2)0.012 (2)0.0030 (17)
C40.042 (2)0.0419 (19)0.037 (2)0.0004 (17)0.0040 (17)0.0021 (17)
C50.0337 (19)0.0340 (17)0.0377 (19)0.0045 (16)0.0009 (16)0.0005 (15)
C80.034 (2)0.0346 (17)0.0349 (19)0.0072 (17)0.0009 (16)0.0007 (14)
C90.042 (2)0.043 (2)0.041 (2)0.008 (2)0.0008 (18)0.0053 (16)
C100.045 (2)0.057 (2)0.049 (2)0.000 (2)0.012 (2)0.0007 (19)
C110.057 (3)0.059 (2)0.031 (2)0.010 (2)0.000 (2)0.0080 (18)
C120.045 (2)0.062 (3)0.051 (3)0.001 (2)0.011 (2)0.011 (2)
C130.036 (2)0.045 (2)0.050 (2)0.0025 (19)0.0008 (18)0.0012 (18)
C150.048 (2)0.052 (2)0.042 (2)0.006 (2)0.0012 (19)0.0025 (18)
C170.091 (4)0.146 (5)0.045 (3)0.017 (5)0.002 (3)0.025 (3)
C180.108 (6)0.205 (8)0.090 (4)0.009 (6)0.017 (4)0.078 (5)
Geometric parameters (Å, º) top
F14—C111.357 (5)C9—C101.385 (6)
O7—C21.221 (5)C10—C111.365 (6)
O16—C151.343 (5)C11—C121.372 (6)
O16—C171.459 (6)C12—C131.378 (6)
O19—C151.222 (6)C17—C181.398 (9)
N1—C21.393 (5)C3—H310.9700
N1—C51.407 (4)C3—H320.9700
N1—C81.442 (4)C9—H90.9300
N6—C51.349 (5)C10—H100.9300
C2—C31.503 (5)C12—H120.9300
C3—C41.504 (6)C13—H130.9300
C4—C51.353 (5)C17—H1710.9700
C4—C151.437 (5)C17—H1720.9700
N6—H610.8600C18—H1810.9600
N6—H620.8600C18—H1820.9600
C8—C131.378 (5)C18—H1830.9600
C8—C91.379 (5)
C15—O16—C17117.0 (4)O16—C15—C4112.1 (4)
C2—N1—C5110.3 (3)O19—C15—C4124.7 (4)
C2—N1—C8124.4 (3)O16—C17—C18110.4 (5)
C5—N1—C8125.4 (3)C2—C3—H31111.00
O7—C2—N1124.5 (3)C2—C3—H32111.00
O7—C2—C3128.7 (4)C4—C3—H31111.00
N1—C2—C3106.7 (3)C4—C3—H32111.00
C2—C3—C4103.8 (3)H31—C3—H32109.00
C3—C4—C5108.4 (3)C8—C9—H9120.00
C3—C4—C15129.2 (3)C10—C9—H9120.00
C5—C4—C15121.8 (3)C9—C10—H10121.00
N1—C5—N6119.9 (3)C11—C10—H10121.00
N1—C5—C4110.6 (3)C11—C12—H12121.00
N6—C5—C4129.5 (3)C13—C12—H12121.00
C5—N6—H62120.00C8—C13—H13120.00
H61—N6—H62120.00C12—C13—H13120.00
C5—N6—H61120.00O16—C17—H171110.00
C9—C8—C13120.9 (3)O16—C17—H172110.00
N1—C8—C13119.1 (3)C18—C17—H171110.00
N1—C8—C9120.0 (3)C18—C17—H172110.00
C8—C9—C10119.1 (4)H171—C17—H172108.00
C9—C10—C11118.9 (4)C17—C18—H181109.00
F14—C11—C10118.6 (4)C17—C18—H182109.00
F14—C11—C12118.5 (4)C17—C18—H183109.00
C10—C11—C12122.9 (4)H181—C18—H182109.00
C11—C12—C13118.0 (4)H181—C18—H183109.00
C8—C13—C12120.2 (4)H182—C18—H183109.00
O16—C15—O19123.3 (4)
C17—O16—C15—O195.0 (7)C3—C4—C5—N6176.4 (3)
C17—O16—C15—C4174.9 (4)C15—C4—C5—N1173.6 (3)
C15—O16—C17—C18144.6 (5)C15—C4—C5—N64.7 (6)
C5—N1—C2—O7176.3 (3)C3—C4—C15—O162.6 (6)
C8—N1—C2—O74.7 (5)C3—C4—C5—N11.9 (4)
C5—N1—C2—C32.9 (4)C3—C4—C15—O19177.3 (4)
C5—N1—C8—C969.1 (4)C5—C4—C15—O16172.5 (4)
C2—N1—C8—C1367.1 (4)C5—C4—C15—O197.4 (7)
C5—N1—C8—C13111.7 (4)N1—C8—C9—C10179.2 (3)
C2—N1—C5—N6179.2 (3)C13—C8—C9—C100.0 (5)
C8—N1—C5—N60.2 (5)N1—C8—C13—C12179.9 (3)
C2—N1—C5—C40.7 (4)C9—C8—C13—C120.7 (5)
C8—N1—C5—C4178.3 (3)C8—C9—C10—C110.2 (6)
C2—N1—C8—C9112.1 (4)C9—C10—C11—C120.3 (7)
C8—N1—C2—C3176.1 (3)C9—C10—C11—F14179.0 (4)
O7—C2—C3—C4175.4 (4)F14—C11—C12—C13179.7 (4)
N1—C2—C3—C43.8 (4)C10—C11—C12—C131.0 (7)
C2—C3—C4—C53.5 (4)C11—C12—C13—C81.2 (6)
C2—C3—C4—C15174.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N6—H61···O190.862.24002.806 (4)123
N6—H62···O7i0.862.21002.970 (4)147
C13—H13···O7ii0.932.60003.320 (5)135
C17—H172···O190.972.33002.692 (6)101
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x1, y1/2, z+1/2.
Summary of various contacts and their percentage contributions to the Hirshfeld surface top
Type of contactContribution
H···H44.9
O···H/H···O20.8
H···F/F···H12.8
C···H/H···C10.4
C···C3.4
C···O/O···C3.0
C···N/N···C1.8
O···F/F···O1.0
O···N/N···O0.6
C···F/F···C0.5
 

Acknowledgements

The authors are thankful to the Department of Physics, SPU, for providing the financial support to carry out the work and also to CSMCRI, Bhavnagar, for the data collection.

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