4-[(2′-Cyano­biphen­yl-4-yl)meth­yl]morpholin-4-ium tetra­fluoridoborate

Li, X.; Huang, X.; Li, K.

doi:10.1107/S160053681101186X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1061

doi:10.1107/S160053681101186X

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4-[(2′-Cyanobiphenyl-4-yl)methyl]morpholin-4-ium tetrafluoridoborate

Xiu-juan Li,^a ^* Xian-gang Huang ^a and Kang-jun Li ^a

^aCollege of Food Engineering, RiZhao Polytechnic, RiZhao 276826, People's Republic of China
^*Correspondence e-mail: lxj818@163.com

(Received 21 March 2011; accepted 30 March 2011; online 7 April 2011)

In the crystal structure of the title compound, C₁₈H₁₉N₂O⁺·BF₄⁻, bifurcated N—H⋯(F,F) hydrogen bonds link the protonated 4′-morpholinemethylbiphenyl-2-carbonitrile cations and slightly distorted tetrafluoroborate anions. π–π interactions [centroid–centroid distance = 3.805 (3) Å] help to consolidate the packing. The dihedral angle between the benzene rings in the cation is 57.24 (11)°.

Related literature

For a related structure, see: SiMa (2010 ).

Experimental

Crystal data

C₁₈H₁₉N₂O⁺·BF₄⁻
M_r = 366.16
Triclinic, $[P \overline 1]$
a = 9.059 (6) Å
b = 9.859 (8) Å
c = 10.597 (8) Å
α = 76.324 (14)°
β = 83.71 (2)°
γ = 86.50 (3)°
V = 913.5 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.978, T_max = 0.978
9817 measured reflections
4098 independent reflections
3039 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.202
S = 1.06
4098 reflections
239 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯F1	0.90 (2)	2.14 (2)	2.902 (3)	141 (2)
N2—H2⋯F3	0.90 (2)	2.35 (2)	3.219 (3)	161 (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681101186X/jh2276sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681101186X/jh2276Isup2.hkl

checkCIF report

Comment top

The crystal structure of 4'-morpholinemethylbiphenyl-2-carbonitrile with nitrate is known (SiMa, 2010).

The asymmetric unit of the title compound is built up of one 4'-morpholinemethylbiphenyl-2-carbonitrile cation with the dihedral angle of 57.24 (11)° between two benzene rings and one tetrafluoroborate anion (Fig 1). The intermolecular N—H···F hydrogen bonds link the cations and anions to chains (Table 1). The π–π stacking interactions of adjacent cyanobenzene rings with a centroid–centroid distance of 3.805 (3)Å stabilize the crystal structure (Fig 2).

Related literature top

For a related structure, see: SiMa (2010).

Experimental top

Tetrafluoroboric acid(10 mmol) was added dropwise under stirring to a solution of 4'-morpholinemethylbiphenyl-2-carbonitrile (10 mmol) ethanol solution. Water was added until all suspended substrates disappeared. Colorless single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation from the solution at room temperature after 5 d, giving a yield of ca 78%.

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of the packing of the title compound. Dashed lines indicate hydrogen bonds and π-π interactions.

4-[(2'-Cyanobiphenyl-4-yl)methyl]morpholin-4-ium tetrafluoridoborate top

Crystal data top

C₁₈H₁₉N₂O⁺·BF₄⁻	Z = 2
M_r = 366.16	F(000) = 380
Triclinic, P1	D_x = 1.331 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.059 (6) Å	Cell parameters from 2199 reflections
b = 9.859 (8) Å	θ = 2.6–27.4°
c = 10.597 (8) Å	µ = 0.11 mm⁻¹
α = 76.324 (14)°	T = 298 K
β = 83.71 (2)°	Prism, colourless
γ = 86.50 (3)°	0.20 × 0.20 × 0.20 mm
V = 913.5 (12) Å³

Data collection top

Rigaku SCXmini diffractometer	4098 independent reflections
Radiation source: fine-focus sealed tube	3039 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.4°, θ_min = 2.6°
ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→12
T_min = 0.978, T_max = 0.978	l = −13→13
9817 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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.202	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.1049P)² + 0.2107P] where P = (F_o² + 2F_c²)/3
4098 reflections	(Δ/σ)_max < 0.001
239 parameters	Δρ_max = 0.49 e Å⁻³
1 restraint	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₈H₁₉N₂O⁺·BF₄⁻	γ = 86.50 (3)°
M_r = 366.16	V = 913.5 (12) Å³
Triclinic, P1	Z = 2
a = 9.059 (6) Å	Mo Kα radiation
b = 9.859 (8) Å	µ = 0.11 mm⁻¹
c = 10.597 (8) Å	T = 298 K
α = 76.324 (14)°	0.20 × 0.20 × 0.20 mm
β = 83.71 (2)°

Data collection top

Rigaku SCXmini diffractometer	4098 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3039 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.978	R_int = 0.028
9817 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	1 restraint
wR(F²) = 0.202	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.49 e Å⁻³
4098 reflections	Δρ_min = −0.30 e Å⁻³
239 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
C1	0.9918 (2)	0.3886 (3)	0.3969 (2)	0.0559 (5)
C2	1.0478 (2)	0.2599 (2)	0.47565 (19)	0.0472 (5)
C3	1.1901 (2)	0.2084 (3)	0.4395 (2)	0.0613 (6)
H3A	1.2463	0.2570	0.3658	0.074*
C4	1.2460 (3)	0.0863 (3)	0.5129 (3)	0.0662 (7)
H4A	1.3404	0.0522	0.4890	0.079*
C5	1.1631 (3)	0.0144 (3)	0.6214 (2)	0.0644 (6)
H5A	1.2009	−0.0692	0.6700	0.077*
C6	1.0234 (2)	0.0653 (2)	0.6593 (2)	0.0533 (5)
H6A	0.9695	0.0162	0.7341	0.064*
C7	0.9623 (2)	0.1888 (2)	0.58744 (18)	0.0436 (4)
C8	0.8154 (2)	0.24449 (19)	0.63377 (18)	0.0424 (4)
C9	0.7937 (2)	0.2673 (2)	0.75930 (19)	0.0521 (5)
H9A	0.8707	0.2464	0.8128	0.062*
C10	0.6601 (2)	0.3203 (3)	0.8053 (2)	0.0564 (5)
H10A	0.6487	0.3376	0.8885	0.068*
C11	0.5416 (2)	0.3483 (2)	0.7281 (2)	0.0475 (5)
C12	0.5617 (2)	0.3237 (2)	0.6039 (2)	0.0513 (5)
H12A	0.4831	0.3409	0.5519	0.062*
C13	0.6973 (2)	0.2736 (2)	0.55624 (19)	0.0480 (5)
H13A	0.7098	0.2594	0.4720	0.058*
C14	0.3952 (2)	0.4050 (2)	0.7809 (2)	0.0570 (6)
H14A	0.4119	0.4897	0.8081	0.068*
H14B	0.3293	0.4291	0.7120	0.068*
C16	0.2802 (2)	0.1734 (2)	0.8569 (2)	0.0523 (5)
H16A	0.3689	0.1267	0.8251	0.063*
H16B	0.2158	0.1995	0.7870	0.063*
C17	0.2012 (3)	0.0752 (2)	0.9722 (3)	0.0633 (6)
H17A	0.1733	−0.0066	0.9457	0.076*
H17B	0.2678	0.0446	1.0400	0.076*
C18	0.1109 (3)	0.2580 (3)	1.0663 (2)	0.0645 (6)
H18A	0.1768	0.2267	1.1345	0.077*
H18B	0.0222	0.3002	1.1034	0.077*
C19	0.1868 (2)	0.3662 (2)	0.9572 (2)	0.0550 (5)
H19A	0.1184	0.4039	0.8922	0.066*
H19B	0.2162	0.4423	0.9914	0.066*
N1	0.9501 (3)	0.4903 (3)	0.3325 (2)	0.0805 (7)
N2	0.32178 (17)	0.30144 (17)	0.89484 (16)	0.0432 (4)
H2	0.384 (2)	0.273 (3)	0.958 (2)	0.064 (7)*
O1	0.07139 (17)	0.14212 (18)	1.02265 (16)	0.0638 (4)
B1	0.5558 (3)	0.2295 (3)	1.1710 (3)	0.0583 (6)
F1	0.4631 (2)	0.33813 (19)	1.1168 (2)	0.1044 (7)
F2	0.70030 (18)	0.2643 (2)	1.13544 (18)	0.0962 (6)
F3	0.5250 (3)	0.1264 (2)	1.1129 (3)	0.1298 (9)
F4	0.5317 (2)	0.2022 (4)	1.29990 (17)	0.1466 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0508 (12)	0.0678 (14)	0.0446 (11)	−0.0121 (10)	−0.0021 (9)	−0.0030 (10)
C2	0.0432 (10)	0.0557 (11)	0.0435 (10)	−0.0053 (8)	−0.0042 (8)	−0.0122 (8)
C3	0.0464 (12)	0.0853 (16)	0.0557 (12)	−0.0068 (11)	0.0029 (9)	−0.0257 (12)
C4	0.0478 (12)	0.0833 (17)	0.0756 (16)	0.0131 (11)	−0.0107 (11)	−0.0360 (14)
C5	0.0664 (14)	0.0620 (13)	0.0698 (15)	0.0143 (11)	−0.0248 (12)	−0.0215 (12)
C6	0.0572 (12)	0.0519 (11)	0.0503 (11)	0.0005 (9)	−0.0105 (9)	−0.0090 (9)
C7	0.0411 (10)	0.0486 (10)	0.0421 (10)	−0.0043 (8)	−0.0064 (7)	−0.0107 (8)
C8	0.0398 (9)	0.0442 (10)	0.0409 (9)	−0.0062 (7)	−0.0018 (7)	−0.0049 (8)
C9	0.0424 (10)	0.0708 (13)	0.0423 (10)	−0.0109 (9)	−0.0033 (8)	−0.0099 (9)
C10	0.0463 (11)	0.0756 (15)	0.0490 (11)	−0.0132 (10)	0.0053 (8)	−0.0196 (10)
C11	0.0411 (10)	0.0427 (10)	0.0556 (11)	−0.0074 (8)	0.0039 (8)	−0.0077 (8)
C12	0.0441 (10)	0.0528 (11)	0.0541 (11)	−0.0020 (8)	−0.0094 (8)	−0.0047 (9)
C13	0.0476 (11)	0.0542 (11)	0.0423 (10)	−0.0019 (8)	−0.0062 (8)	−0.0106 (8)
C14	0.0495 (11)	0.0417 (10)	0.0723 (14)	−0.0059 (8)	0.0111 (10)	−0.0054 (10)
C16	0.0475 (11)	0.0501 (11)	0.0614 (12)	−0.0106 (8)	0.0070 (9)	−0.0208 (10)
C17	0.0554 (13)	0.0523 (12)	0.0777 (15)	−0.0121 (10)	0.0077 (11)	−0.0101 (11)
C18	0.0563 (13)	0.0836 (16)	0.0521 (12)	−0.0033 (11)	0.0075 (10)	−0.0183 (12)
C19	0.0485 (11)	0.0586 (12)	0.0594 (12)	0.0031 (9)	0.0049 (9)	−0.0224 (10)
N1	0.0768 (15)	0.0817 (15)	0.0685 (13)	−0.0147 (12)	−0.0147 (11)	0.0177 (12)
N2	0.0370 (8)	0.0448 (8)	0.0486 (9)	−0.0033 (6)	−0.0026 (7)	−0.0125 (7)
O1	0.0457 (8)	0.0748 (11)	0.0671 (10)	−0.0151 (7)	0.0091 (7)	−0.0123 (8)
B1	0.0525 (14)	0.0645 (15)	0.0594 (15)	0.0077 (11)	−0.0145 (11)	−0.0158 (12)
F1	0.1023 (14)	0.0844 (12)	0.1375 (16)	0.0327 (10)	−0.0665 (12)	−0.0316 (11)
F2	0.0606 (10)	0.1263 (15)	0.0970 (12)	−0.0091 (9)	−0.0087 (8)	−0.0145 (11)
F3	0.1141 (16)	0.0880 (13)	0.211 (3)	−0.0028 (11)	−0.0255 (16)	−0.0766 (16)
F4	0.0801 (13)	0.281 (3)	0.0580 (10)	0.0229 (16)	−0.0057 (8)	−0.0060 (14)

Geometric parameters (Å, º) top

C1—N1	1.140 (3)	C13—H13A	0.9300
C1—C2	1.441 (3)	C14—N2	1.506 (3)
C2—C7	1.403 (3)	C14—H14A	0.9700
C2—C3	1.403 (3)	C14—H14B	0.9700
C3—C4	1.372 (4)	C16—N2	1.493 (3)
C3—H3A	0.9300	C16—C17	1.509 (3)
C4—C5	1.371 (4)	C16—H16A	0.9700
C4—H4A	0.9300	C16—H16B	0.9700
C5—C6	1.386 (3)	C17—O1	1.428 (3)
C5—H5A	0.9300	C17—H17A	0.9700
C6—C7	1.393 (3)	C17—H17B	0.9700
C6—H6A	0.9300	C18—O1	1.408 (3)
C7—C8	1.486 (3)	C18—C19	1.510 (3)
C8—C9	1.392 (3)	C18—H18A	0.9700
C8—C13	1.395 (3)	C18—H18B	0.9700
C9—C10	1.374 (3)	C19—N2	1.505 (3)
C9—H9A	0.9300	C19—H19A	0.9700
C10—C11	1.396 (3)	C19—H19B	0.9700
C10—H10A	0.9300	N2—H2	0.904 (16)
C11—C12	1.386 (3)	B1—F4	1.324 (3)
C11—C14	1.509 (3)	B1—F3	1.363 (3)
C12—C13	1.384 (3)	B1—F2	1.363 (3)
C12—H12A	0.9300	B1—F1	1.374 (3)

N1—C1—C2	178.5 (3)	N2—C14—H14B	109.2
C7—C2—C3	120.7 (2)	C11—C14—H14B	109.2
C7—C2—C1	120.47 (18)	H14A—C14—H14B	107.9
C3—C2—C1	118.78 (19)	N2—C16—C17	110.42 (18)
C4—C3—C2	120.0 (2)	N2—C16—H16A	109.6
C4—C3—H3A	120.0	C17—C16—H16A	109.6
C2—C3—H3A	120.0	N2—C16—H16B	109.6
C5—C4—C3	120.1 (2)	C17—C16—H16B	109.6
C5—C4—H4A	120.0	H16A—C16—H16B	108.1
C3—C4—H4A	120.0	O1—C17—C16	110.81 (19)
C4—C5—C6	120.5 (2)	O1—C17—H17A	109.5
C4—C5—H5A	119.8	C16—C17—H17A	109.5
C6—C5—H5A	119.8	O1—C17—H17B	109.5
C5—C6—C7	121.3 (2)	C16—C17—H17B	109.5
C5—C6—H6A	119.4	H17A—C17—H17B	108.1
C7—C6—H6A	119.4	O1—C18—C19	111.95 (18)
C6—C7—C2	117.45 (19)	O1—C18—H18A	109.2
C6—C7—C8	120.07 (17)	C19—C18—H18A	109.2
C2—C7—C8	122.40 (18)	O1—C18—H18B	109.2
C9—C8—C13	118.51 (18)	C19—C18—H18B	109.2
C9—C8—C7	119.17 (17)	H18A—C18—H18B	107.9
C13—C8—C7	122.31 (18)	N2—C19—C18	110.08 (18)
C10—C9—C8	121.01 (19)	N2—C19—H19A	109.6
C10—C9—H9A	119.5	C18—C19—H19A	109.6
C8—C9—H9A	119.5	N2—C19—H19B	109.6
C9—C10—C11	120.4 (2)	C18—C19—H19B	109.6
C9—C10—H10A	119.8	H19A—C19—H19B	108.2
C11—C10—H10A	119.8	C16—N2—C19	109.84 (16)
C12—C11—C10	118.88 (19)	C16—N2—C14	112.09 (17)
C12—C11—C14	121.43 (19)	C19—N2—C14	111.26 (16)
C10—C11—C14	119.7 (2)	C16—N2—H2	107.1 (16)
C13—C12—C11	120.69 (19)	C19—N2—H2	105.8 (16)
C13—C12—H12A	119.7	C14—N2—H2	110.5 (16)
C11—C12—H12A	119.7	C18—O1—C17	110.10 (17)
C12—C13—C8	120.45 (19)	F4—B1—F3	116.5 (3)
C12—C13—H13A	119.8	F4—B1—F2	108.7 (2)
C8—C13—H13A	119.8	F3—B1—F2	109.0 (2)
N2—C14—C11	112.09 (17)	F4—B1—F1	109.9 (2)
N2—C14—H14A	109.2	F3—B1—F1	102.7 (2)
C11—C14—H14A	109.2	F2—B1—F1	109.9 (2)

C7—C2—C3—C4	0.8 (3)	C9—C10—C11—C14	179.33 (19)
C1—C2—C3—C4	179.9 (2)	C10—C11—C12—C13	−0.8 (3)
C2—C3—C4—C5	0.1 (3)	C14—C11—C12—C13	179.01 (18)
C3—C4—C5—C6	−1.1 (4)	C11—C12—C13—C8	1.3 (3)
C4—C5—C6—C7	1.2 (3)	C9—C8—C13—C12	−0.2 (3)
C5—C6—C7—C2	−0.3 (3)	C7—C8—C13—C12	179.14 (18)
C5—C6—C7—C8	−177.10 (19)	C12—C11—C14—N2	114.6 (2)
C3—C2—C7—C6	−0.7 (3)	C10—C11—C14—N2	−65.7 (3)
C1—C2—C7—C6	−179.81 (19)	N2—C16—C17—O1	58.1 (3)
C3—C2—C7—C8	176.01 (18)	O1—C18—C19—N2	−56.8 (3)
C1—C2—C7—C8	−3.1 (3)	C17—C16—N2—C19	−53.4 (2)
C6—C7—C8—C9	54.6 (3)	C17—C16—N2—C14	−177.59 (18)
C2—C7—C8—C9	−122.0 (2)	C18—C19—N2—C16	52.3 (2)
C6—C7—C8—C13	−124.7 (2)	C18—C19—N2—C14	176.95 (18)
C2—C7—C8—C13	58.6 (3)	C11—C14—N2—C16	−64.1 (2)
C13—C8—C9—C10	−1.5 (3)	C11—C14—N2—C19	172.46 (17)
C7—C8—C9—C10	179.17 (19)	C19—C18—O1—C17	61.2 (2)
C8—C9—C10—C11	2.0 (3)	C16—C17—O1—C18	−61.4 (3)
C9—C10—C11—C12	−0.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···F1	0.90 (2)	2.14 (2)	2.902 (3)	141 (2)
N2—H2···F3	0.90 (2)	2.35 (2)	3.219 (3)	161 (2)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₉N₂O⁺·BF₄⁻
M_r	366.16
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.059 (6), 9.859 (8), 10.597 (8)
α, β, γ (°)	76.324 (14), 83.71 (2), 86.50 (3)
V (Å³)	913.5 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.978, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	9817, 4098, 3039
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.202, 1.06
No. of reflections	4098
No. of parameters	239
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.30

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···F1	0.904 (16)	2.14 (2)	2.902 (3)	141 (2)
N2—H2···F3	0.904 (16)	2.353 (18)	3.219 (3)	161 (2)

Acknowledgements

The authors are grateful to RiZhao Polytechnic for support.

References

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
SiMa, W. (2010). Acta Cryst. E66, o2042. Web of Science CSD CrossRef IUCr Journals Google Scholar