N,N′-Bis(4-fluoro­phen­yl)urea

Loh, W.-S.; Fun, H.-K.; Sarveswari, S.; Vijayakumar, V.; Ragavan, R.V.

doi:10.1107/S1600536810016399

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1319

https://doi.org/10.1107/S1600536810016399

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N,N′-Bis(4-fluorophenyl)urea

Wan-Sin Loh,^a ‡ Hoong-Kun Fun,^a ^*§ S. Sarveswari,^b V. Vijayakumar ^b and R. Venkat Ragavan ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India
^*Correspondence e-mail: hkfun@usm.my

(Received 28 April 2010; accepted 5 May 2010; online 12 May 2010)

The asymmetric unit of the title compound, C₁₃H₁₀F₂N₂O, contains one and a half N,N′-bis(4-fluorophenyl)urea molecules. One of the molecules has crystallographic twofold rotation symmetry. The benzene rings are twisted from each other by dihedral angles of 29.69 (6)° for the molecule in a general position and 89.83 (6)° for the symmetry-generated molecule. In the crystal structure, a pair of intermolecular N—H⋯O hydrogen bonds link symmetry-related molecules into chains along the b axis, forming R₂¹(6) ring motifs.

Related literature

For background to and the biological activity of bis-arylureas, see: Khire et al. (2004 ); McDonnell et al. (2008 ); Francisco et al. (2004 ); Bigi et al. (1998 ). For the synthetic method, see: Sarveswari & Raja (2006 ). For a related structure, see: Jai-nhuknan et al. (1997 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₃H₁₀F₂N₂O
M_r = 248.23
Monoclinic, C 2/c
a = 67.541 (4) Å
b = 4.5750 (3) Å
c = 10.7098 (6) Å
β = 95.969 (2)°
V = 3291.4 (3) Å³
Z = 12
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 100 K
0.59 × 0.12 × 0.09 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.932, T_max = 0.990
21915 measured reflections
5986 independent reflections
4304 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.159
S = 1.05
5986 reflections
257 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.69 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1NA⋯O1Aⁱ	0.83 (2)	2.08 (2)	2.8331 (13)	151.7 (18)
N1B—H1NB⋯O1Bⁱ	0.89 (3)	2.02 (3)	2.8392 (18)	153.3 (19)
N2A—H2NA⋯O1Aⁱ	0.855 (18)	2.080 (17)	2.8547 (16)	150.5 (13)
Symmetry code: (i) x, y+1, z.

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/S1600536810016399/lh5040sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016399/lh5040Isup2.hkl

checkCIF report

Comment top

The synthesis of bis-arylureas has received considerable attention due to their wide range of biological applications. They act as potential Raf kinase inhibitors (Khire et al., 2004) and antagonists of human vanilloid receptor 1 (VR 1) (McDonnell et al., 2008). Phenyl thiazolylurea derivatives have been reported as inhibitors of Murine receptor A and Murine receptor B (Francisco et al., 2004). Some substituted ureas are used as antidiabetic and tranquilizing drugs, antioxidants in gasoline, corrosion inhibitor and herbicides (Bigi et al., 1998).

The asymmetric unit of the title compound (Fig. 1), comprises of one and a half N,N'-bis-(4-fluorophenyl)urea molecules. The half molecule has a twofold rotation symmetry, generated by symmetry code -x, y, -z+3/2. In the molecule with suffix A, both benzene rings (C1A–C6A and C8A–C13A) are twisted from each other with a dihedral angle of 29.69 (6)° whereas in molecule with suffix B, the dihedral angle between the benzene rings (C1B–C6B and C1BA–C6BA) is 89.83 (6)°. The structure is comparable to the related structure (Jai-nhuknan et al., 1997).

In the crystal packing (Fig. 2), intermolecular N1A—H1NA···O1A and N2A—H2NA···O1A hydrogen bonds (Table 1) link the adjacent molecules into chains along the b axis, forming R₂¹(6) ring motifs (Bernstein et al., 1995).

Related literature top

For background to and the biological activity of bis-arylureas, see: Khire et al. (2004); McDonnell et al. (2008); Francisco et al. (2004); Bigi et al. (1998). For the synthetic method, see: Sarveswari & Raja (2006). For a related structure, see: Jai-nhuknan et al. (1997). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

The compound N,N'-bis-(4-fluorophenyl)urea was synthesized using the method available in the literature (Sarveswari & Raja, 2006) and the obtained crude product was recrystallized from absolute ethanol. M.P.: 519 K. Yield: 56%.

Structure description top

For background to and the biological activity of bis-arylureas, see: Khire et al. (2004); McDonnell et al. (2008); Francisco et al. (2004); Bigi et al. (1998). For the synthetic method, see: Sarveswari & Raja (2006). For a related structure, see: Jai-nhuknan et al. (1997). For hydrogen-bond motifs, see: Bernstein et al. (1995). 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 and the atom-numbering scheme. Atoms with suffix BA [C1BA–C6BA/N1BA/F1BA] are generated by symmetry code -x, y, -z+3/2.
	Fig. 2. The crystal packing of the title compound, viewed approximately along the a axis, showing R₂¹(6) ring motifs. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

N,N'-Bis(4-fluorophenyl)urea top

Crystal data top

C₁₃H₁₀F₂N₂O	F(000) = 1536
M_r = 248.23	D_x = 1.503 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3635 reflections
a = 67.541 (4) Å	θ = 2.4–32.1°
b = 4.5750 (3) Å	µ = 0.12 mm⁻¹
c = 10.7098 (6) Å	T = 100 K
β = 95.969 (2)°	Block, brown
V = 3291.4 (3) Å³	0.59 × 0.12 × 0.09 mm
Z = 12

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	5986 independent reflections
Radiation source: fine-focus sealed tube	4304 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
φ and ω scans	θ_max = 32.7°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −102→102
T_min = 0.932, T_max = 0.990	k = −6→6
21915 measured reflections	l = −16→16

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0899P)² + 0.1948P] where P = (F_o² + 2F_c²)/3
5986 reflections	(Δ/σ)_max < 0.001
257 parameters	Δρ_max = 0.69 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₁₃H₁₀F₂N₂O	V = 3291.4 (3) Å³
M_r = 248.23	Z = 12
Monoclinic, C2/c	Mo Kα radiation
a = 67.541 (4) Å	µ = 0.12 mm⁻¹
b = 4.5750 (3) Å	T = 100 K
c = 10.7098 (6) Å	0.59 × 0.12 × 0.09 mm
β = 95.969 (2)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	5986 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4304 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.990	R_int = 0.050
21915 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.69 e Å⁻³
5986 reflections	Δρ_min = −0.51 e Å⁻³
257 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 > σ(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
F1A	0.244179 (12)	0.5229 (2)	0.33663 (8)	0.02522 (19)
O1A	0.167883 (13)	0.5447 (2)	0.62122 (9)	0.0198 (2)
N1A	0.180685 (15)	0.9777 (2)	0.55991 (10)	0.0162 (2)
N2A	0.153498 (15)	0.9743 (3)	0.67129 (11)	0.0175 (2)
C1A	0.209007 (17)	0.6417 (3)	0.56407 (11)	0.0163 (2)
H1AA	0.2064	0.5746	0.6426	0.020*
C2A	0.225076 (17)	0.5295 (3)	0.50863 (12)	0.0180 (2)
H2AA	0.2332	0.3860	0.5486	0.022*
C3A	0.228714 (17)	0.6362 (3)	0.39263 (12)	0.0178 (2)
C4A	0.217243 (18)	0.8517 (3)	0.33077 (11)	0.0184 (2)
H4AA	0.2203	0.9236	0.2539	0.022*
C5A	0.200924 (18)	0.9591 (3)	0.38612 (11)	0.0172 (2)
H5AA	0.1928	1.1008	0.3451	0.021*
C6A	0.196784 (16)	0.8543 (3)	0.50280 (10)	0.0142 (2)
C7A	0.167422 (16)	0.8158 (3)	0.61783 (11)	0.0150 (2)
C8A	0.138631 (16)	0.8455 (3)	0.73842 (11)	0.0154 (2)
C9A	0.143599 (18)	0.6409 (3)	0.83227 (12)	0.0187 (2)
H9AA	0.1568	0.5838	0.8508	0.022*
C10A	0.128905 (18)	0.5208 (3)	0.89873 (12)	0.0207 (3)
H10A	0.1320	0.3818	0.9610	0.025*
C11A	0.109514 (19)	0.6143 (3)	0.86946 (12)	0.0209 (3)
C12A	0.104185 (18)	0.8202 (3)	0.77910 (12)	0.0219 (3)
H12A	0.0910	0.8809	0.7630	0.026*
C13A	0.118945 (18)	0.9362 (3)	0.71211 (12)	0.0193 (2)
H13A	0.1157	1.0745	0.6497	0.023*
F2A	0.095139 (12)	0.4948 (2)	0.93363 (9)	0.0309 (2)
F1B	0.072613 (12)	0.6424 (2)	1.16351 (8)	0.0289 (2)
O1B	0.0000	0.6661 (3)	0.7500	0.0262 (3)
N1B	0.013863 (16)	1.0982 (3)	0.82126 (11)	0.0193 (2)
C1B	0.024299 (18)	0.7613 (3)	0.99248 (12)	0.0200 (2)
H1BA	0.0112	0.6961	0.9919	0.024*
C2B	0.03907 (2)	0.6455 (3)	1.07851 (12)	0.0213 (3)
H2BA	0.0362	0.4998	1.1343	0.026*
C3B	0.058161 (18)	0.7529 (3)	1.07883 (12)	0.0210 (3)
C4B	0.063141 (18)	0.9679 (3)	0.99790 (12)	0.0212 (3)
H4BA	0.0761	1.0385	1.0018	0.025*
C5B	0.048369 (18)	1.0776 (3)	0.91008 (12)	0.0194 (2)
H5BA	0.0515	1.2200	0.8533	0.023*
C6B	0.028914 (17)	0.9741 (3)	0.90722 (12)	0.0170 (2)
C7B	0.0000	0.9380 (4)	0.7500	0.0181 (3)
H1NA	0.1792 (3)	1.157 (5)	0.5567 (17)	0.028 (5)*
H1NB	0.0136 (3)	1.289 (6)	0.8078 (19)	0.043 (6)*
H2NA	0.1535 (2)	1.160 (4)	0.6624 (16)	0.022 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1A	0.0210 (3)	0.0251 (5)	0.0312 (4)	0.0051 (3)	0.0105 (3)	−0.0019 (4)
O1A	0.0215 (4)	0.0090 (4)	0.0302 (5)	−0.0003 (3)	0.0084 (3)	−0.0003 (4)
N1A	0.0180 (4)	0.0082 (5)	0.0231 (5)	0.0010 (4)	0.0059 (4)	0.0014 (4)
N2A	0.0184 (4)	0.0094 (5)	0.0258 (5)	0.0014 (4)	0.0076 (4)	0.0010 (4)
C1A	0.0170 (5)	0.0144 (6)	0.0175 (5)	0.0004 (4)	0.0018 (4)	0.0011 (4)
C2A	0.0159 (5)	0.0147 (6)	0.0232 (6)	0.0025 (4)	0.0015 (4)	0.0012 (5)
C3A	0.0148 (5)	0.0171 (6)	0.0220 (5)	0.0005 (4)	0.0040 (4)	−0.0041 (5)
C4A	0.0195 (5)	0.0187 (6)	0.0174 (5)	−0.0004 (5)	0.0046 (4)	0.0001 (5)
C5A	0.0183 (5)	0.0151 (6)	0.0181 (5)	0.0007 (5)	0.0021 (4)	0.0006 (4)
C6A	0.0150 (4)	0.0106 (5)	0.0170 (5)	−0.0005 (4)	0.0017 (4)	−0.0015 (4)
C7A	0.0153 (4)	0.0119 (5)	0.0178 (5)	0.0006 (4)	0.0015 (4)	−0.0001 (4)
C8A	0.0157 (4)	0.0114 (5)	0.0195 (5)	−0.0011 (4)	0.0039 (4)	−0.0013 (4)
C9A	0.0178 (5)	0.0176 (6)	0.0205 (5)	−0.0003 (5)	0.0016 (4)	0.0011 (5)
C10A	0.0212 (5)	0.0207 (7)	0.0205 (6)	0.0006 (5)	0.0039 (4)	0.0035 (5)
C11A	0.0201 (5)	0.0200 (6)	0.0239 (6)	−0.0038 (5)	0.0078 (4)	−0.0015 (5)
C12A	0.0161 (5)	0.0215 (7)	0.0286 (6)	0.0010 (5)	0.0044 (4)	0.0005 (5)
C13A	0.0174 (5)	0.0168 (6)	0.0238 (6)	0.0019 (5)	0.0030 (4)	0.0020 (5)
F2A	0.0247 (4)	0.0319 (5)	0.0384 (5)	−0.0037 (4)	0.0150 (3)	0.0060 (4)
F1B	0.0284 (4)	0.0301 (5)	0.0263 (4)	0.0062 (4)	−0.0060 (3)	0.0031 (4)
O1B	0.0302 (7)	0.0107 (6)	0.0351 (7)	0.000	−0.0093 (6)	0.000
N1B	0.0177 (4)	0.0112 (5)	0.0280 (5)	−0.0008 (4)	−0.0017 (4)	0.0004 (4)
C1B	0.0194 (5)	0.0172 (6)	0.0235 (6)	−0.0020 (5)	0.0031 (4)	−0.0001 (5)
C2B	0.0275 (6)	0.0165 (6)	0.0200 (5)	−0.0009 (5)	0.0029 (4)	0.0015 (5)
C3B	0.0216 (5)	0.0203 (6)	0.0201 (5)	0.0039 (5)	−0.0024 (4)	−0.0008 (5)
C4B	0.0168 (5)	0.0223 (7)	0.0244 (6)	−0.0004 (5)	0.0011 (4)	−0.0012 (5)
C5B	0.0184 (5)	0.0180 (6)	0.0218 (5)	−0.0010 (5)	0.0022 (4)	0.0007 (5)
C6B	0.0171 (5)	0.0123 (6)	0.0213 (5)	0.0007 (4)	0.0010 (4)	−0.0016 (4)
C7B	0.0170 (7)	0.0136 (8)	0.0234 (8)	0.000	0.0005 (6)	0.000

Geometric parameters (Å, º) top

F1A—C3A	1.3601 (13)	C10A—H10A	0.9300
O1A—C7A	1.2412 (15)	C11A—F2A	1.3611 (14)
N1A—C7A	1.3606 (15)	C11A—C12A	1.371 (2)
N1A—C6A	1.4190 (15)	C12A—C13A	1.3925 (17)
N1A—H1NA	0.83 (2)	C12A—H12A	0.9300
N2A—C7A	1.3602 (15)	C13A—H13A	0.9300
N2A—C8A	1.4223 (15)	F1B—C3B	1.3589 (15)
N2A—H2NA	0.85 (2)	O1B—C7B	1.244 (2)
C1A—C2A	1.3886 (16)	N1B—C7B	1.3593 (15)
C1A—C6A	1.3948 (17)	N1B—C6B	1.4173 (16)
C1A—H1AA	0.9300	N1B—H1NB	0.88 (3)
C2A—C3A	1.3805 (18)	C1B—C2B	1.3902 (18)
C2A—H2AA	0.9300	C1B—C6B	1.3921 (18)
C3A—C4A	1.3799 (18)	C1B—H1BA	0.9300
C4A—C5A	1.3941 (16)	C2B—C3B	1.3798 (19)
C4A—H4AA	0.9300	C2B—H2BA	0.9300
C5A—C6A	1.3937 (16)	C3B—C4B	1.376 (2)
C5A—H5AA	0.9300	C4B—C5B	1.3916 (18)
C8A—C9A	1.3888 (18)	C4B—H4BA	0.9300
C8A—C13A	1.3935 (16)	C5B—C6B	1.3942 (17)
C9A—C10A	1.3929 (17)	C5B—H5BA	0.9300
C9A—H9AA	0.9300	C7B—N1Bⁱ	1.3593 (15)
C10A—C11A	1.3824 (18)

C7A—N1A—C6A	123.39 (11)	C9A—C10A—H10A	121.0
C7A—N1A—H1NA	118.3 (13)	F2A—C11A—C12A	118.92 (12)
C6A—N1A—H1NA	118.3 (13)	F2A—C11A—C10A	118.03 (12)
C7A—N2A—C8A	123.17 (11)	C12A—C11A—C10A	123.05 (12)
C7A—N2A—H2NA	118.4 (11)	C11A—C12A—C13A	118.42 (12)
C8A—N2A—H2NA	118.4 (11)	C11A—C12A—H12A	120.8
C2A—C1A—C6A	120.49 (11)	C13A—C12A—H12A	120.8
C2A—C1A—H1AA	119.8	C12A—C13A—C8A	120.09 (12)
C6A—C1A—H1AA	119.8	C12A—C13A—H13A	120.0
C3A—C2A—C1A	118.30 (11)	C8A—C13A—H13A	120.0
C3A—C2A—H2AA	120.8	C7B—N1B—C6B	123.66 (12)
C1A—C2A—H2AA	120.8	C7B—N1B—H1NB	116.0 (14)
F1A—C3A—C4A	118.63 (11)	C6B—N1B—H1NB	120.2 (14)
F1A—C3A—C2A	118.60 (11)	C2B—C1B—C6B	120.46 (11)
C4A—C3A—C2A	122.77 (11)	C2B—C1B—H1BA	119.8
C3A—C4A—C5A	118.48 (11)	C6B—C1B—H1BA	119.8
C3A—C4A—H4AA	120.8	C3B—C2B—C1B	118.17 (13)
C5A—C4A—H4AA	120.8	C3B—C2B—H2BA	120.9
C6A—C5A—C4A	120.08 (12)	C1B—C2B—H2BA	120.9
C6A—C5A—H5AA	120.0	F1B—C3B—C4B	118.73 (12)
C4A—C5A—H5AA	120.0	F1B—C3B—C2B	118.40 (13)
C5A—C6A—C1A	119.84 (11)	C4B—C3B—C2B	122.87 (12)
C5A—C6A—N1A	118.94 (11)	C3B—C4B—C5B	118.59 (12)
C1A—C6A—N1A	121.14 (10)	C3B—C4B—H4BA	120.7
O1A—C7A—N2A	122.47 (11)	C5B—C4B—H4BA	120.7
O1A—C7A—N1A	122.79 (11)	C4B—C5B—C6B	120.01 (13)
N2A—C7A—N1A	114.74 (11)	C4B—C5B—H5BA	120.0
C9A—C8A—C13A	120.06 (11)	C6B—C5B—H5BA	120.0
C9A—C8A—N2A	121.00 (10)	C1B—C6B—C5B	119.87 (12)
C13A—C8A—N2A	118.90 (11)	C1B—C6B—N1B	120.79 (11)
C8A—C9A—C10A	120.28 (11)	C5B—C6B—N1B	119.26 (12)
C8A—C9A—H9AA	119.9	O1B—C7B—N1Bⁱ	122.63 (9)
C10A—C9A—H9AA	119.9	O1B—C7B—N1B	122.63 (8)
C11A—C10A—C9A	118.08 (12)	N1Bⁱ—C7B—N1B	114.74 (17)
C11A—C10A—H10A	121.0

Symmetry code: (i) −x, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···O1Aⁱⁱ	0.83 (2)	2.08 (2)	2.8331 (13)	151.7 (18)
N1B—H1NB···O1Bⁱⁱ	0.89 (3)	2.02 (3)	2.8392 (18)	153.3 (19)
N2A—H2NA···O1Aⁱⁱ	0.855 (18)	2.080 (17)	2.8547 (16)	150.5 (13)

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀F₂N₂O
M_r	248.23
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	67.541 (4), 4.5750 (3), 10.7098 (6)
β (°)	95.969 (2)
V (Å³)	3291.4 (3)
Z	12
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.59 × 0.12 × 0.09

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.932, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	21915, 5986, 4304
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.761

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.159, 1.05
No. of reflections	5986
No. of parameters	257
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.51

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
N1A—H1NA···O1Aⁱ	0.83 (2)	2.08 (2)	2.8331 (13)	151.7 (18)
N1B—H1NB···O1Bⁱ	0.89 (3)	2.02 (3)	2.8392 (18)	153.3 (19)
N2A—H2NA···O1Aⁱ	0.855 (18)	2.080 (17)	2.8547 (16)	150.5 (13)

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

Footnotes

‡Thomson Reuters ResearcherID: C-7581-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (1001/PFIZIK/811012). WSL thanks the Malaysian Government and USM for the award of Research Fellowship. VV is grateful to the DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

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