N6-(4-Fluoro­benz­yl)-3-nitro­pyridine-2,6-diamine

Ge, J.; Qian, X.

doi:10.1107/S1600536811018642

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1481

doi:10.1107/S1600536811018642

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N⁶-(4-Fluorobenzyl)-3-nitropyridine-2,6-diamine

Ji-long Ge ^a ^* and Xiao-min Qian ^b

^aChangzhou Siyao Pharmaceuticals Co. Ltd, Changzhou 213004, People's Republic of China, and ^bOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: chmsunbw@seu.edu.cn

(Received 18 April 2011; accepted 17 May 2011; online 20 May 2011)

In the title compound, C₁₂H₁₁FN₄O₂, the pyridine ring is connected to a benzene ring by a –CH₂—NH₂- chain. The nitro group is twisted out of the pyridine ring plane [torsion angle O—N—C—C = 10.41 (10)°]. An intramolecular N—H⋯O hydrogen bond occurs. The fluorobenzene ring is disordered over two positions [occupancy ratio = 0.59 (3):0.41 (3)]. Intermolecular N—H⋯O and N—H⋯N hydrogen bonds stabilize the crystal structure.

Related literature

The title compound is an intermediate in the synthesis of analgesic drugs. For the analgesic properties of flupirtine (systematic name ethyl{2-amino-6-[(4-fluorobenzyl)amino]pyridin-3-yl}carbamate), see: Klawe & Maschke (2009 ). For synthetic procedures, see: Gerhard & Ilia (2010 ). For a related structure, see: Wang (2009 ).

Experimental

Crystal data

C₁₂H₁₁FN₄O₂
M_r = 262.25
Monoclinic, P 2₁ /n
a = 14.8187 (14) Å
b = 5.9972 (6) Å
c = 14.8840 (15) Å
β = 109.827 (1)°
V = 1244.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.38 × 0.15 × 0.11 mm

Data collection

Rigaku SCXmini CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.960, T_max = 0.988
5923 measured reflections
2184 independent reflections
1169 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.140
S = 1.03
2184 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯O1	0.86	2.03	2.651 (3)	129
N3—H3A⋯N1ⁱ	0.86	2.17	3.028 (3)	174
N2—H2⋯O1ⁱⁱ	0.86	2.35	3.060 (3)	141
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018642/pv2411sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018642/pv2411Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811018642/pv2411Isup3.cml

checkCIF report

Comment top

Flupirtine, ethyl{2-amino-6-[(4-fluorobenzyl)amino]pyridin-3-yl}carbamate, is of great importance owing to its analgesic properties (Klawe & Maschke, 2009). In this article, we report the crystal structure of the title compound which is one of the key intermediates in the synthsis of analgesia drugs (Gerhard & Ilia, 2010).

In the title molecule (Fig. 1), a pyridine ring is connected with a benzene ring by –CH₂—NH₂- chain and the nitro group is twisted out of the pyridine ring plane [torsion angle O1—N4—C4—C5 = 10.41 (10)°]. The crystal structure is stabilized by intermolecular N—H···O and N—H···N hydrogen bonds (Figure 2 and Table 1).

Related literature top

The title compound is an intermediate in the synthesis of analgesic drugs. For the analgesic properties of flupirtine (systematic name ethyl{2-amino-6-[(4-fluorobenzyl)amino]pyridin-3-yl}carbamate), see: Klawe & Maschke (2009). For synthetic procedures, see: Gerhard & Ilia (2010). For a related structure, see: Wang (2009).

Experimental top

To a solution of 2-amino-3-nitro-6-chloropyridine (7.8 g, 45 mmol) in 2-propanol (50 ml) were added 4-fluorobenzylamine (5.63 g, 45 mmol) and triethylamine (6.45 g,64 mmol) (Gerhard & Ilia, 2010). Then another 30 ml 2-propanol was add to the above solution. The mixture was heated to backflow and stirred for 3 h. Then 100 ml water was add to the mixture to obtain the title compound which was recrystallized from ethanol by slow evaporation (yield 10.2 g, 91%).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. An ORTEP (Farrugia, 1997) view of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Smaller fraction of the fluorobenzene ring has been plotted with hollow bonds.
	Fig. 2. A packing diagram of the title compound showing hydrogen bonds. Smaller fraction of the fluorobenzene ring has been excluded.

N⁶-(4-Fluorobenzyl)-3-nitropyridine-2,6-diamine top

Crystal data top

C₁₂H₁₁FN₄O₂	F(000) = 544
M_r = 262.25	D_x = 1.400 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1144 reflections
a = 14.8187 (14) Å	θ = 2.4–26.9°
b = 5.9972 (6) Å	µ = 0.11 mm⁻¹
c = 14.8840 (15) Å	T = 298 K
β = 109.827 (1)°	Prism, yellow
V = 1244.3 (2) Å³	0.38 × 0.15 × 0.11 mm
Z = 4

Data collection top

Rigaku SCXmini CCD diffractometer	2184 independent reflections
Radiation source: fine-focus sealed tube	1169 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
Detector resolution: 8.192 pixels mm^-1	θ_max = 25.0°, θ_min = 2.4°
ϕ and ω scans	h = −14→17
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −5→7
T_min = 0.960, T_max = 0.988	l = −17→17
5923 measured reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0585P)²] where P = (F_o² + 2F_c²)/3
2184 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₂H₁₁FN₄O₂	V = 1244.3 (2) Å³
M_r = 262.25	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.8187 (14) Å	µ = 0.11 mm⁻¹
b = 5.9972 (6) Å	T = 298 K
c = 14.8840 (15) Å	0.38 × 0.15 × 0.11 mm
β = 109.827 (1)°

Data collection top

Rigaku SCXmini CCD diffractometer	2184 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1169 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.988	R_int = 0.056
5923 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.03	Δρ_max = 0.21 e Å⁻³
2184 reflections	Δρ_min = −0.22 e Å⁻³
227 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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	Occ. (<1)
F1	0.6846 (16)	0.5113 (18)	0.0036 (13)	0.121 (4)	0.59 (3)
F1'	0.7330 (17)	0.538 (2)	0.050 (2)	0.105 (5)	0.41 (3)
N1	0.55771 (13)	0.2584 (4)	0.46588 (14)	0.0474 (6)
N2	0.49151 (15)	0.4615 (4)	0.33021 (15)	0.0608 (7)
H2	0.4453	0.3666	0.3173	0.073*
N3	0.61662 (15)	0.0425 (4)	0.59818 (14)	0.0597 (7)
H3A	0.5670	−0.0413	0.5754	0.072*
H3B	0.6593	0.0109	0.6523	0.072*
N4	0.78769 (16)	0.3201 (4)	0.66405 (17)	0.0611 (7)
O1	0.78379 (14)	0.1726 (4)	0.72145 (14)	0.0792 (7)
O2	0.86264 (15)	0.4308 (4)	0.68041 (15)	0.0852 (7)
C1	0.56363 (18)	0.4356 (5)	0.41323 (18)	0.0487 (7)
C2	0.6413 (2)	0.5883 (5)	0.4429 (2)	0.0604 (8)
H2A	0.6429	0.7126	0.4061	0.072*
C3	0.71288 (19)	0.5481 (5)	0.5260 (2)	0.0581 (8)
H3	0.7649	0.6448	0.5463	0.070*
C4	0.70977 (17)	0.3639 (4)	0.58174 (18)	0.0488 (7)
C5	0.62743 (17)	0.2205 (4)	0.54982 (17)	0.0454 (6)
C6	0.4844 (2)	0.6355 (5)	0.2601 (2)	0.0666 (8)
H6A	0.5020	0.7765	0.2934	0.080*
H6B	0.4180	0.6470	0.2188	0.080*
C7	0.5459 (2)	0.6006 (5)	0.1989 (2)	0.0611 (8)
C8	0.6128 (14)	0.425 (4)	0.2145 (16)	0.067 (4)	0.59 (3)
H8	0.6195	0.3224	0.2632	0.081*	0.59 (3)
C9	0.669 (3)	0.407 (6)	0.156 (3)	0.097 (7)	0.59 (3)
H9	0.7225	0.3149	0.1712	0.116*	0.59 (3)
C10	0.6390 (18)	0.540 (6)	0.071 (2)	0.087 (6)	0.59 (3)
C11	0.5858 (15)	0.726 (3)	0.0609 (13)	0.082 (4)	0.59 (3)
H11	0.5823	0.8329	0.0145	0.099*	0.59 (3)
C12	0.5373 (18)	0.747 (4)	0.1241 (16)	0.072 (4)	0.59 (3)
H12	0.4958	0.8669	0.1164	0.086*	0.59 (3)
C8'	0.581 (2)	0.398 (6)	0.186 (2)	0.081 (6)	0.41 (3)
H8'	0.5631	0.2733	0.2137	0.097*	0.41 (3)
C9'	0.641 (3)	0.369 (8)	0.134 (3)	0.086 (8)	0.41 (3)
H9'	0.6603	0.2268	0.1225	0.103*	0.41 (3)
C10'	0.673 (3)	0.559 (7)	0.098 (3)	0.078 (7)	0.41 (3)
C11'	0.626 (2)	0.753 (4)	0.099 (2)	0.082 (6)	0.41 (3)
H11'	0.6350	0.8719	0.0630	0.099*	0.41 (3)
C12'	0.566 (2)	0.782 (7)	0.152 (3)	0.080 (7)	0.41 (3)
H12'	0.5393	0.9213	0.1550	0.096*	0.41 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.158 (10)	0.109 (4)	0.135 (8)	0.014 (5)	0.100 (7)	0.009 (5)
F1'	0.124 (10)	0.090 (5)	0.141 (11)	0.018 (6)	0.097 (9)	0.018 (6)
N1	0.0386 (12)	0.0553 (15)	0.0437 (12)	−0.0061 (10)	0.0080 (10)	0.0023 (11)
N2	0.0504 (14)	0.0698 (17)	0.0557 (14)	−0.0039 (11)	0.0096 (12)	0.0163 (12)
N3	0.0514 (13)	0.0679 (17)	0.0481 (12)	−0.0160 (12)	0.0016 (11)	0.0080 (12)
N4	0.0469 (15)	0.0722 (18)	0.0548 (15)	−0.0129 (13)	0.0050 (13)	−0.0155 (14)
O1	0.0631 (13)	0.0991 (18)	0.0574 (12)	−0.0146 (12)	−0.0030 (10)	0.0125 (12)
O2	0.0537 (13)	0.0941 (18)	0.0881 (15)	−0.0231 (12)	−0.0015 (11)	−0.0111 (13)
C1	0.0441 (15)	0.0529 (18)	0.0504 (15)	−0.0001 (13)	0.0180 (13)	0.0025 (14)
C2	0.0638 (18)	0.0505 (19)	0.0666 (19)	−0.0090 (15)	0.0218 (16)	0.0059 (14)
C3	0.0485 (16)	0.0545 (19)	0.0687 (18)	−0.0170 (14)	0.0165 (15)	−0.0079 (16)
C4	0.0418 (15)	0.0527 (18)	0.0478 (15)	−0.0069 (12)	0.0100 (13)	−0.0068 (13)
C5	0.0399 (14)	0.0534 (18)	0.0417 (14)	−0.0054 (13)	0.0121 (12)	−0.0031 (13)
C6	0.0653 (19)	0.071 (2)	0.0636 (18)	0.0142 (16)	0.0224 (16)	0.0190 (16)
C7	0.0670 (19)	0.054 (2)	0.0666 (19)	0.0078 (16)	0.0278 (16)	0.0107 (16)
C8	0.078 (9)	0.056 (7)	0.074 (8)	0.010 (6)	0.034 (7)	0.010 (6)
C9	0.108 (15)	0.074 (14)	0.122 (15)	0.017 (10)	0.056 (12)	0.005 (9)
C10	0.101 (14)	0.081 (11)	0.102 (13)	0.014 (11)	0.063 (10)	0.009 (9)
C11	0.101 (10)	0.073 (7)	0.083 (8)	0.011 (7)	0.044 (7)	0.024 (6)
C12	0.082 (11)	0.064 (9)	0.079 (10)	0.015 (7)	0.039 (8)	0.019 (7)
C8'	0.101 (18)	0.060 (9)	0.090 (16)	−0.004 (11)	0.045 (12)	0.012 (10)
C9'	0.11 (2)	0.057 (12)	0.111 (19)	0.010 (13)	0.069 (16)	0.007 (13)
C10'	0.096 (18)	0.057 (10)	0.11 (2)	−0.003 (13)	0.066 (14)	0.010 (12)
C11'	0.098 (14)	0.067 (9)	0.098 (14)	−0.004 (9)	0.054 (11)	0.019 (10)
C12'	0.091 (17)	0.062 (10)	0.097 (19)	0.003 (11)	0.044 (13)	0.010 (11)

Geometric parameters (Å, º) top

F1—C10	1.39 (3)	C6—H6B	0.9700
F1'—C10'	1.32 (4)	C7—C8'	1.36 (3)
N1—C1	1.341 (3)	C7—C12'	1.38 (4)
N1—C5	1.343 (3)	C7—C12	1.39 (3)
N2—C1	1.341 (3)	C7—C8	1.41 (2)
N2—C6	1.454 (3)	C8—C9	1.40 (4)
N2—H2	0.8600	C8—H8	0.9300
N3—C5	1.327 (3)	C9—C10	1.43 (5)
N3—H3A	0.8600	C9—H9	0.9300
N3—H3B	0.8600	C10—C11	1.35 (4)
N4—O1	1.245 (3)	C11—C12	1.37 (3)
N4—O2	1.245 (3)	C11—H11	0.9300
N4—C4	1.394 (3)	C12—H12	0.9300
C1—C2	1.419 (4)	C8'—C9'	1.38 (6)
C2—C3	1.350 (4)	C8'—H8'	0.9300
C2—H2A	0.9300	C9'—C10'	1.41 (7)
C3—C4	1.392 (4)	C9'—H9'	0.9300
C3—H3	0.9300	C10'—C11'	1.36 (5)
C4—C5	1.436 (3)	C11'—C12'	1.38 (4)
C6—C7	1.506 (4)	C11'—H11'	0.9300
C6—H6A	0.9700	C12'—H12'	0.9300

C1—N1—C5	119.7 (2)	C12—C7—C8	118.1 (15)
C1—N2—C6	125.8 (2)	C8'—C7—C6	123.0 (15)
C1—N2—H2	117.1	C12'—C7—C6	118.4 (18)
C6—N2—H2	117.1	C12—C7—C6	119.2 (12)
C5—N3—H3A	120.0	C8—C7—C6	122.6 (10)
C5—N3—H3B	120.0	C9—C8—C7	119 (2)
H3A—N3—H3B	120.0	C9—C8—H8	120.4
O1—N4—O2	119.4 (2)	C7—C8—H8	120.4
O1—N4—C4	121.3 (2)	C8—C9—C10	116 (3)
O2—N4—C4	119.3 (3)	C8—C9—H9	122.0
N2—C1—N1	116.1 (2)	C10—C9—H9	122.0
N2—C1—C2	121.4 (3)	C11—C10—F1	116 (2)
N1—C1—C2	122.5 (2)	C11—C10—C9	123 (3)
C3—C2—C1	118.1 (3)	F1—C10—C9	119 (3)
C3—C2—H2A	120.9	C10—C11—C12	115 (2)
C1—C2—H2A	120.9	C10—C11—H11	122.5
C2—C3—C4	120.9 (3)	C12—C11—H11	122.5
C2—C3—H3	119.6	C11—C12—C7	125 (2)
C4—C3—H3	119.6	C11—C12—H12	117.7
C3—C4—N4	119.2 (2)	C7—C12—H12	117.7
C3—C4—C5	118.3 (2)	C7—C8'—C9'	123 (3)
N4—C4—C5	122.4 (2)	C7—C8'—H8'	118.7
N3—C5—N1	116.4 (2)	C9'—C8'—H8'	118.7
N3—C5—C4	123.2 (2)	C8'—C9'—C10'	119 (4)
N1—C5—C4	120.4 (2)	C8'—C9'—H9'	120.7
N2—C6—C7	115.0 (2)	C10'—C9'—H9'	120.7
N2—C6—H6A	108.5	F1'—C10'—C11'	122 (3)
C7—C6—H6A	108.5	F1'—C10'—C9'	120 (4)
N2—C6—H6B	108.5	C11'—C10'—C9'	116 (4)
C7—C6—H6B	108.5	C10'—C11'—C12'	123 (3)
H6A—C6—H6B	107.5	C10'—C11'—H11'	118.3
C8'—C7—C12'	119 (2)	C12'—C11'—H11'	118.3
C8'—C7—C12	112.9 (17)	C7—C12'—C11'	119 (3)
C12'—C7—C12	21.8 (14)	C7—C12'—H12'	120.7
C8'—C7—C8	22.5 (12)	C11'—C12'—H12'	120.7
C12'—C7—C8	114.4 (19)

C6—N2—C1—N1	−177.6 (2)	C12—C7—C8—C9	1.3 (19)
C6—N2—C1—C2	2.4 (4)	C6—C7—C8—C9	−178.4 (13)
C5—N1—C1—N2	179.7 (2)	C7—C8—C9—C10	−14 (3)
C5—N1—C1—C2	−0.3 (4)	C8—C9—C10—C11	24 (3)
N2—C1—C2—C3	−178.1 (2)	C8—C9—C10—F1	−172.7 (18)
N1—C1—C2—C3	2.0 (4)	F1—C10—C11—C12	176.8 (13)
C1—C2—C3—C4	−0.9 (4)	C9—C10—C11—C12	−19 (3)
C2—C3—C4—N4	176.0 (2)	C10—C11—C12—C7	5 (2)
C2—C3—C4—C5	−1.5 (4)	C8'—C7—C12—C11	−21 (2)
O1—N4—C4—C3	171.9 (3)	C12'—C7—C12—C11	89 (8)
O2—N4—C4—C3	−8.0 (4)	C8—C7—C12—C11	3.6 (19)
O1—N4—C4—C5	−10.7 (4)	C6—C7—C12—C11	−176.7 (11)
O2—N4—C4—C5	169.3 (2)	C12'—C7—C8'—C9'	5 (3)
C1—N1—C5—N3	179.8 (2)	C12—C7—C8'—C9'	29 (3)
C1—N1—C5—C4	−2.3 (3)	C8—C7—C8'—C9'	−80 (6)
C3—C4—C5—N3	−179.0 (2)	C6—C7—C8'—C9'	−177 (2)
N4—C4—C5—N3	3.6 (4)	C7—C8'—C9'—C10'	5 (4)
C3—C4—C5—N1	3.2 (4)	C8'—C9'—C10'—F1'	178 (3)
N4—C4—C5—N1	−174.2 (2)	C8'—C9'—C10'—C11'	−14 (5)
C1—N2—C6—C7	77.2 (3)	F1'—C10'—C11'—C12'	−177.8 (19)
N2—C6—C7—C8'	20.6 (16)	C9'—C10'—C11'—C12'	15 (4)
N2—C6—C7—C12'	−161.0 (15)	C8'—C7—C12'—C11'	−5 (2)
N2—C6—C7—C12	174.1 (10)	C12—C7—C12'—C11'	−85 (8)
N2—C6—C7—C8	−6.3 (10)	C8—C7—C12'—C11'	20 (2)
C8'—C7—C8—C9	83 (6)	C6—C7—C12'—C11'	176.8 (13)
C12'—C7—C8—C9	−23 (2)	C10'—C11'—C12'—C7	−6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O1	0.86	2.03	2.651 (3)	129
N3—H3A···N1ⁱ	0.86	2.17	3.028 (3)	174
N2—H2···O1ⁱⁱ	0.86	2.35	3.060 (3)	141

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₁FN₄O₂
M_r	262.25
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	14.8187 (14), 5.9972 (6), 14.8840 (15)
β (°)	109.827 (1)
V (Å³)	1244.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.38 × 0.15 × 0.11

Data collection
Diffractometer	Rigaku SCXmini CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.960, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	5923, 2184, 1169
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.140, 1.03
No. of reflections	2184
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.22

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O1	0.86	2.03	2.651 (3)	129
N3—H3A···N1ⁱ	0.86	2.17	3.028 (3)	174
N2—H2···O1ⁱⁱ	0.86	2.35	3.060 (3)	141

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1/2, −y+1/2, z−1/2.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gerhard. J & Ilia, F. (2010). Patent WO 2010/136113 A1, 2 December 2010. Google Scholar
Klawe, C. & Maschke, M. (2009). Expert Opin. Pharmacother. 10, 1495–1500. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, B. (2009). Acta Cryst. E65, m861. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 6| June 2011| Page o1481

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