2-[({[Bis(pyridin-2-yl)methylidene]hydrazinecarbonyl}hydrazinylidene)(pyridin-2-yl)methyl]pyridinium tetra­fluoro­borate

Zhang, J.

doi:10.1107/S1600536811025359

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1874

doi:10.1107/S1600536811025359

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2-[({[Bis(pyridin-2-yl)methylidene]hydrazinecarbonyl}hydrazinylidene)(pyridin-2-yl)methyl]pyridinium tetrafluoroborate

Jie Zhang ^a ^*

^aSchool of Environment Science and Spatial Informatics, China University of Mining and Technology, Xuzhou 221116, Jiangsu Province, People's Republic of China
^*Correspondence e-mail: zhangjie973@126.com

(Received 8 June 2011; accepted 28 June 2011; online 2 July 2011)

In the title compound, C₂₃H₁₉N₈O⁺·BF₄⁻, one pyridine N atom is protonated. Two intramolecular N—H⋯N hydrogen bonds occur. In the crystal, intermolecular N—H⋯N hydrogen bond links neighboring C₂₃H₁₉N₈O⁺ units into cyclic supramolecular dimers while C—H⋯O hydrogen bonds link the C₂₃H₁₉N₈O⁺ units into a two-dimensional supramolecular network structure.

Related literature

For the synthesis and crystal structure of the precursor ligand, 1,3-bis(bis(2-pyridyl)methylene)amino)urea, see: Manoj et al. (2005 ). For a tetranuclear iron(II) complex based on a derivative of the title compound, see: Wu et al. (2009 ).

Experimental

Crystal data

C₂₃H₁₉N₈O⁺·BF₄⁻
M_r = 510.27
Triclinic, $[P \overline 1]$
a = 7.9187 (16) Å
b = 10.626 (2) Å
c = 13.623 (3) Å
α = 90.03 (3)°
β = 91.50 (3)°
γ = 97.85 (3)°
V = 1135.1 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 123 K
0.22 × 0.19 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.974, T_max = 0.981
18299 measured reflections
5175 independent reflections
4025 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.151
S = 0.98
5175 reflections
346 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N7ⁱ	0.90 (2)	1.92 (2)	2.792 (2)	163.5 (15)
N3—H30⋯N8	0.88 (2)	1.99 (2)	2.658 (2)	132.1 (19)
N4—H40⋯N6	0.83 (2)	2.02 (2)	2.640 (2)	132 (2)
C2—H2⋯O1ⁱⁱ	0.93	2.41	3.083 (2)	129 (1)
C18—H18⋯O1ⁱⁱⁱ	0.93	2.46	3.355 (2)	162 (1)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y+2, -z+1; (iii) x, y-1, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811025359/ez2251sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025359/ez2251Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811025359/ez2251Isup3.cml

checkCIF report

Comment top

Recently, the ligand 1,3-bis(bis(2-pyridyl)methylene)amino)urea and its derivatives have been employed to assembly clusters with novel topological structures and interesting magnetic and photomagnetic properties (Wu et al., 2009). In our attempt to synthesize a tetranuclear square iron cluster based on the ligand 1,3-bis(bis(2-pyridyl)methylene)amino)urea and Fe^II(BF₄)₂.4H₂O, the title compound was obtained unexpectedly. Herein, we report the crystal structure of 1,3-bis(bis(2-pyridyl)methylene)amino)urea tetrafluoroborate (I).

The geometry and labeling scheme for the crystal structure of the title complex are depicted in Figure 1. The molecular structure comprises a [C₂₃H₁₉N₈O]⁺ cation and a charge balancing anion [BF₄]^-. In the molecular structure, one pyridine nitrogen was protonated by one hydrogen. The cation adopts an EE configuration about the hydrazine bonds which is similar to its precursor 1,3-bis(bis(2-pyridyl)methylene)amino)urea (Manoj et al., 2005).

The C—O bond length is 1.2157 (18) Å. The C—N_hydrazine double bond lengths are 1.297 (2) and 1.301 (2) Å, respectively. There are two intramolecular N—H···N hydrogen bonds. A relatively strong intermolecular N—H···N hydrogen bond links two neighboring [C₂₃H₁₉N₈O]⁺ units into a cyclic supramolecular dimer. In addition, C—H···O hydrogen bonds link the [C₂₃H₁₉N₈O]⁺ units into a two-dimensional supramolecular network structure as shown in Figure 2.

Related literature top

For the synthesis and crystal structure of the precursor ligand, 1,3-bis(bis(2-pyridyl)methylene)amino)urea, see: Manoj et al. (2005). For a tetranuclear iron(II) complex based on a derivative of the title compound, see: Wu et al. (2009).

Experimental top

The title complex was prepared as following: a methanol solution (5 ml) of [Fe^II(BF₄)₂].4H₂O (60 mg, 0.2 mmol) was added slowly to a MeOH suspension (20 ml) containing the ligand 1,3-bis(bis(2-pyridyl)methylene)amino)urea (84 mg, 0.2 mmol). After stirring 30 min, the mixture was then carefully filtered and the resulting solution was kept at room temperature for about two days, producing colorless block-shape crystals of (I) with high yield (ca 60%).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of (I) with the unique atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of part of the crystal structure of (I) along the c axis, showing two-dimensional supramolecular structure through formed by N—H···N and C—H···O hydrogen bonds.

2-[({[Bis(pyridin-2-yl)methylidene]hydrazinecarbonyl}hydrazinylidene)(pyridin- 2-yl)methyl]pyridinium tetrafluoroborate top

Crystal data top

C₂₃H₁₉N₈O⁺·BF₄⁻	Z = 2
M_r = 510.27	F(000) = 524
Triclinic, P1	D_x = 1.493 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9187 (16) Å	Cell parameters from 3505 reflections
b = 10.626 (2) Å	θ = 2.3–26.7°
c = 13.623 (3) Å	µ = 0.12 mm⁻¹
α = 90.03 (3)°	T = 123 K
β = 91.50 (3)°	Block, colorless
γ = 97.85 (3)°	0.22 × 0.19 × 0.16 mm
V = 1135.1 (4) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	5175 independent reflections
Radiation source: fine-focus sealed tube	4025 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −10→10
T_min = 0.974, T_max = 0.981	k = −13→13
18299 measured reflections	l = −17→17

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) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.1033P)² + 0.3032P] where P = (F_o² + 2F_c²)/3
5175 reflections	(Δ/σ)_max < 0.001
346 parameters	Δρ_max = 0.68 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₂₃H₁₉N₈O⁺·BF₄⁻	γ = 97.85 (3)°
M_r = 510.27	V = 1135.1 (4) Å³
Triclinic, P1	Z = 2
a = 7.9187 (16) Å	Mo Kα radiation
b = 10.626 (2) Å	µ = 0.12 mm⁻¹
c = 13.623 (3) Å	T = 123 K
α = 90.03 (3)°	0.22 × 0.19 × 0.16 mm
β = 91.50 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5175 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	4025 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.981	R_int = 0.032
18299 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.68 e Å⁻³
5175 reflections	Δρ_min = −0.49 e Å⁻³
346 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
H1	−0.020 (3)	0.896 (2)	0.6632 (16)	0.033 (6)*
H30	0.224 (3)	0.592 (2)	0.5650 (17)	0.041 (6)*
H40	0.141 (3)	0.567 (2)	0.3285 (17)	0.038 (6)*
O1	0.07813 (16)	0.75955 (10)	0.40804 (8)	0.0215 (3)
N1	0.05189 (17)	0.93425 (12)	0.70991 (9)	0.0151 (3)
N2	0.16150 (16)	0.75693 (12)	0.60077 (9)	0.0149 (3)
N3	0.17522 (17)	0.65646 (12)	0.54249 (9)	0.0147 (3)
N4	0.16693 (18)	0.56751 (12)	0.38758 (10)	0.0164 (3)
N6	0.15116 (17)	0.43582 (12)	0.22247 (9)	0.0178 (3)
N7	0.20613 (16)	0.14392 (12)	0.42932 (9)	0.0154 (3)
N8	0.32921 (18)	0.55934 (13)	0.69471 (10)	0.0210 (3)
N5	0.21894 (16)	0.46491 (12)	0.43220 (9)	0.0147 (3)
C13	0.24217 (19)	0.36556 (14)	0.38154 (11)	0.0143 (3)
C8	0.27284 (19)	0.65124 (14)	0.74875 (11)	0.0163 (3)
C19	0.22420 (19)	0.34758 (14)	0.27322 (11)	0.0152 (3)
C14	0.29165 (19)	0.26067 (14)	0.44455 (11)	0.0142 (3)
C20	0.2835 (2)	0.24569 (15)	0.22615 (12)	0.0193 (3)
H20	0.3378	0.1878	0.2621	0.023*
C15	0.4159 (2)	0.28667 (15)	0.51871 (11)	0.0175 (3)
H15	0.4729	0.3685	0.5276	0.021*
C5	0.2903 (2)	0.93506 (16)	0.81632 (12)	0.0219 (4)
H5	0.3817	0.8971	0.8408	0.026*
C1	0.13426 (19)	0.66862 (14)	0.44403 (11)	0.0152 (3)
C16	0.4535 (2)	0.18811 (15)	0.57937 (11)	0.0185 (3)
H16	0.5366	0.2026	0.6291	0.022*
C6	0.1830 (2)	0.87492 (14)	0.74368 (11)	0.0158 (3)
C17	0.3646 (2)	0.06836 (15)	0.56384 (11)	0.0183 (3)
H17	0.3867	0.0008	0.6033	0.022*
C9	0.2753 (2)	0.64769 (16)	0.85125 (12)	0.0207 (3)
H9	0.2326	0.7102	0.8871	0.025*
C18	0.2421 (2)	0.05004 (14)	0.48887 (11)	0.0174 (3)
H18	0.1821	−0.0308	0.4794	0.021*
C7	0.20552 (19)	0.75424 (14)	0.69332 (11)	0.0151 (3)
C12	0.3918 (2)	0.46578 (17)	0.74277 (13)	0.0261 (4)
H12	0.4309	0.4025	0.7059	0.031*
C2	0.0211 (2)	1.04672 (15)	0.74398 (12)	0.0208 (3)
H2	−0.0712	1.0831	0.7189	0.025*
C23	0.1328 (2)	0.42228 (16)	0.12492 (12)	0.0218 (4)
H23	0.0845	0.4838	0.0896	0.026*
C22	0.1824 (2)	0.32125 (17)	0.07416 (12)	0.0245 (4)
H22	0.1634	0.3135	0.0066	0.029*
C10	0.3423 (2)	0.54963 (16)	0.89862 (12)	0.0237 (4)
H10	0.3467	0.5465	0.9669	0.028*
C11	0.4023 (2)	0.45699 (16)	0.84425 (13)	0.0254 (4)
H11	0.4485	0.3905	0.8745	0.030*
C21	0.2605 (2)	0.23194 (16)	0.12549 (12)	0.0239 (4)
H21	0.2970	0.1639	0.0930	0.029*
C3	0.1261 (2)	1.10889 (17)	0.81633 (13)	0.0276 (4)
H3	0.1061	1.1874	0.8401	0.033*
C4	0.2611 (2)	1.05221 (18)	0.85257 (13)	0.0284 (4)
H4	0.3330	1.0925	0.9015	0.034*
B1	0.2959 (3)	0.8076 (2)	0.10945 (17)	0.0306 (5)
F1	0.3407 (2)	0.7618 (2)	0.20065 (11)	0.0788 (5)
F2	0.42071 (15)	0.78336 (12)	0.04479 (8)	0.0381 (3)
F3	0.14286 (17)	0.73994 (14)	0.07990 (12)	0.0618 (4)
F4	0.2908 (2)	0.93300 (14)	0.11734 (17)	0.0898 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0329 (7)	0.0149 (6)	0.0180 (6)	0.0091 (5)	−0.0041 (5)	−0.0001 (4)
N1	0.0181 (7)	0.0144 (6)	0.0127 (6)	0.0024 (5)	−0.0015 (5)	−0.0014 (5)
N2	0.0157 (6)	0.0142 (6)	0.0147 (6)	0.0021 (5)	0.0002 (5)	−0.0019 (5)
N3	0.0194 (7)	0.0118 (6)	0.0135 (6)	0.0049 (5)	−0.0013 (5)	−0.0010 (5)
N4	0.0245 (7)	0.0134 (6)	0.0120 (6)	0.0052 (5)	−0.0028 (5)	−0.0002 (5)
N6	0.0194 (7)	0.0182 (7)	0.0157 (6)	0.0022 (5)	−0.0008 (5)	−0.0007 (5)
N7	0.0172 (6)	0.0135 (6)	0.0157 (6)	0.0031 (5)	0.0009 (5)	−0.0016 (5)
N8	0.0269 (8)	0.0194 (7)	0.0181 (7)	0.0082 (6)	−0.0022 (6)	−0.0005 (5)
N5	0.0164 (6)	0.0116 (6)	0.0160 (6)	0.0017 (5)	−0.0014 (5)	0.0013 (5)
C13	0.0139 (7)	0.0139 (7)	0.0147 (7)	0.0008 (6)	−0.0005 (6)	−0.0006 (6)
C8	0.0141 (7)	0.0181 (8)	0.0165 (7)	0.0019 (6)	−0.0017 (6)	0.0001 (6)
C19	0.0150 (7)	0.0151 (7)	0.0147 (7)	−0.0008 (6)	0.0006 (6)	−0.0001 (6)
C14	0.0158 (7)	0.0130 (7)	0.0145 (7)	0.0037 (6)	0.0028 (6)	−0.0017 (5)
C20	0.0224 (8)	0.0177 (8)	0.0180 (8)	0.0028 (6)	0.0036 (6)	0.0002 (6)
C15	0.0176 (8)	0.0151 (7)	0.0194 (8)	0.0012 (6)	−0.0011 (6)	−0.0011 (6)
C5	0.0204 (8)	0.0261 (9)	0.0191 (8)	0.0040 (7)	−0.0034 (6)	−0.0050 (6)
C1	0.0165 (7)	0.0138 (7)	0.0150 (7)	0.0015 (6)	−0.0007 (6)	−0.0008 (6)
C16	0.0180 (8)	0.0226 (8)	0.0158 (7)	0.0058 (6)	−0.0024 (6)	−0.0003 (6)
C6	0.0167 (7)	0.0172 (7)	0.0135 (7)	0.0025 (6)	0.0015 (6)	−0.0004 (6)
C17	0.0205 (8)	0.0181 (8)	0.0175 (7)	0.0064 (6)	0.0025 (6)	0.0050 (6)
C9	0.0222 (8)	0.0231 (8)	0.0172 (8)	0.0049 (7)	0.0000 (6)	0.0001 (6)
C18	0.0199 (8)	0.0130 (7)	0.0196 (8)	0.0028 (6)	0.0027 (6)	−0.0007 (6)
C7	0.0139 (7)	0.0157 (7)	0.0158 (7)	0.0020 (6)	0.0008 (6)	−0.0005 (6)
C12	0.0361 (10)	0.0214 (8)	0.0229 (9)	0.0128 (7)	−0.0034 (7)	−0.0009 (7)
C2	0.0259 (9)	0.0180 (8)	0.0196 (8)	0.0070 (6)	0.0004 (7)	−0.0017 (6)
C23	0.0246 (9)	0.0244 (8)	0.0159 (8)	0.0025 (7)	−0.0027 (6)	0.0009 (6)
C22	0.0321 (10)	0.0275 (9)	0.0125 (8)	−0.0011 (7)	0.0006 (7)	−0.0027 (6)
C10	0.0281 (9)	0.0266 (9)	0.0158 (8)	0.0020 (7)	−0.0031 (7)	0.0044 (6)
C11	0.0306 (9)	0.0218 (8)	0.0246 (9)	0.0080 (7)	−0.0058 (7)	0.0057 (7)
C21	0.0310 (9)	0.0212 (8)	0.0195 (8)	0.0024 (7)	0.0068 (7)	−0.0050 (6)
C3	0.0351 (10)	0.0214 (9)	0.0266 (9)	0.0056 (7)	−0.0011 (8)	−0.0122 (7)
C4	0.0287 (9)	0.0302 (9)	0.0252 (9)	0.0013 (7)	−0.0055 (7)	−0.0130 (7)
B1	0.0283 (11)	0.0281 (11)	0.0357 (12)	0.0049 (9)	−0.0021 (9)	−0.0079 (9)
F1	0.0849 (13)	0.1169 (15)	0.0361 (8)	0.0202 (11)	−0.0023 (8)	0.0033 (9)
F2	0.0329 (6)	0.0449 (7)	0.0360 (6)	0.0037 (5)	−0.0016 (5)	−0.0140 (5)
F3	0.0313 (7)	0.0607 (9)	0.0918 (12)	0.0014 (6)	−0.0033 (7)	−0.0231 (8)
F4	0.0708 (12)	0.0280 (8)	0.174 (2)	0.0124 (7)	0.0381 (12)	−0.0134 (10)

Geometric parameters (Å, º) top

O1—C1	1.2157 (18)	C5—C4	1.389 (2)
N1—C2	1.337 (2)	C5—H5	0.9300
N1—C6	1.357 (2)	C16—C17	1.381 (2)
N1—H1	0.90 (2)	C16—H16	0.9300
N2—C7	1.301 (2)	C6—C7	1.488 (2)
N2—N3	1.3481 (18)	C17—C18	1.385 (2)
N3—C1	1.3820 (19)	C17—H17	0.9300
N3—H30	0.89 (2)	C9—C10	1.385 (2)
N4—N5	1.3557 (17)	C9—H9	0.9300
N4—C1	1.378 (2)	C18—H18	0.9300
N4—H40	0.82 (2)	C12—C11	1.387 (2)
N6—C23	1.339 (2)	C12—H12	0.9300
N6—C19	1.349 (2)	C2—C3	1.380 (2)
N7—C18	1.3418 (19)	C2—H2	0.9300
N7—C14	1.343 (2)	C23—C22	1.383 (2)
N8—C12	1.335 (2)	C23—H23	0.9300
N8—C8	1.353 (2)	C22—C21	1.383 (2)
N5—C13	1.297 (2)	C22—H22	0.9300
C13—C19	1.489 (2)	C10—C11	1.374 (3)
C13—C14	1.495 (2)	C10—H10	0.9300
C8—C9	1.396 (2)	C11—H11	0.9300
C8—C7	1.480 (2)	C21—H21	0.9300
C19—C20	1.399 (2)	C3—C4	1.378 (3)
C14—C15	1.392 (2)	C3—H3	0.9300
C20—C21	1.384 (2)	C4—H4	0.9300
C20—H20	0.9300	B1—F4	1.342 (3)
C15—C16	1.393 (2)	B1—F3	1.373 (3)
C15—H15	0.9300	B1—F1	1.390 (3)
C5—C6	1.384 (2)	B1—F2	1.391 (3)

C2—N1—C6	123.20 (14)	C16—C17—H17	120.4
C2—N1—H1	117.6 (14)	C18—C17—H17	120.4
C6—N1—H1	119.2 (14)	C10—C9—C8	118.98 (15)
C7—N2—N3	120.02 (13)	C10—C9—H9	120.5
N2—N3—C1	116.77 (13)	C8—C9—H9	120.5
N2—N3—H30	120.6 (15)	N7—C18—C17	122.81 (14)
C1—N3—H30	121.9 (15)	N7—C18—H18	118.6
N5—N4—C1	119.28 (13)	C17—C18—H18	118.6
N5—N4—H40	121.7 (16)	N2—C7—C8	128.54 (14)
C1—N4—H40	118.4 (16)	N2—C7—C6	111.30 (13)
C23—N6—C19	118.19 (14)	C8—C7—C6	120.15 (13)
C18—N7—C14	118.10 (13)	N8—C12—C11	124.13 (16)
C12—N8—C8	117.68 (14)	N8—C12—H12	117.9
C13—N5—N4	120.72 (13)	C11—C12—H12	117.9
N5—C13—C19	127.73 (14)	N1—C2—C3	120.10 (16)
N5—C13—C14	112.55 (13)	N1—C2—H2	119.9
C19—C13—C14	119.72 (13)	C3—C2—H2	119.9
N8—C8—C9	121.70 (14)	N6—C23—C22	123.18 (16)
N8—C8—C7	116.38 (13)	N6—C23—H23	118.4
C9—C8—C7	121.90 (14)	C22—C23—H23	118.4
N6—C19—C20	121.65 (14)	C21—C22—C23	118.89 (15)
N6—C19—C13	116.70 (13)	C21—C22—H22	120.6
C20—C19—C13	121.63 (14)	C23—C22—H22	120.6
N7—C14—C15	122.42 (14)	C11—C10—C9	119.63 (15)
N7—C14—C13	117.28 (13)	C11—C10—H10	120.2
C15—C14—C13	120.22 (13)	C9—C10—H10	120.2
C21—C20—C19	119.31 (15)	C10—C11—C12	117.84 (15)
C21—C20—H20	120.3	C10—C11—H11	121.1
C19—C20—H20	120.3	C12—C11—H11	121.1
C14—C15—C16	118.96 (14)	C22—C21—C20	118.71 (15)
C14—C15—H15	120.5	C22—C21—H21	120.6
C16—C15—H15	120.5	C20—C21—H21	120.6
C6—C5—C4	119.88 (16)	C4—C3—C2	118.64 (16)
C6—C5—H5	120.1	C4—C3—H3	120.7
C4—C5—H5	120.1	C2—C3—H3	120.7
O1—C1—N4	121.74 (14)	C3—C4—C5	120.25 (16)
O1—C1—N3	124.77 (14)	C3—C4—H4	119.9
N4—C1—N3	113.48 (13)	C5—C4—H4	119.9
C17—C16—C15	118.44 (14)	F4—B1—F3	113.43 (19)
C17—C16—H16	120.8	F4—B1—F1	108.7 (2)
C15—C16—H16	120.8	F3—B1—F1	107.76 (19)
N1—C6—C5	117.93 (14)	F4—B1—F2	110.79 (19)
N1—C6—C7	116.20 (13)	F3—B1—F2	108.98 (17)
C5—C6—C7	125.70 (14)	F1—B1—F2	106.95 (17)
C16—C17—C18	119.25 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N7ⁱ	0.90 (2)	1.92 (2)	2.792 (2)	163.5 (15)
N3—H30···N8	0.88 (2)	1.99 (2)	2.658 (2)	132.1 (19)
N4—H40···N6	0.83 (2)	2.02 (2)	2.640 (2)	132 (2)
C2—H2···O1ⁱⁱ	0.93	2.41	3.083 (2)	129 (1)
C18—H18···O1ⁱⁱⁱ	0.93	2.46	3.355 (2)	162 (1)

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

Experimental details

Crystal data
Chemical formula	C₂₃H₁₉N₈O⁺·BF₄⁻
M_r	510.27
Crystal system, space group	Triclinic, P1
Temperature (K)	123
a, b, c (Å)	7.9187 (16), 10.626 (2), 13.623 (3)
α, β, γ (°)	90.03 (3), 91.50 (3), 97.85 (3)
V (Å³)	1135.1 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.22 × 0.19 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.974, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	18299, 5175, 4025
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.151, 0.98
No. of reflections	5175
No. of parameters	346
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.49

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N7ⁱ	0.90 (2)	1.92 (2)	2.792 (2)	163.5 (15)
N3—H30···N8	0.88 (2)	1.99 (2)	2.658 (2)	132.1 (19)
N4—H40···N6	0.83 (2)	2.02 (2)	2.640 (2)	132 (2)
C2—H2···O1ⁱⁱ	0.930	2.411	3.083 (2)	129.11 (15)
C18—H18···O1ⁱⁱⁱ	0.930	2.458	3.355 (2)	161.92 (15)

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

Acknowledgements

This work was supported by supported by the Fundamental Research Funds for the Central Universities (China University of Mining and Technology, No. 2011QNA08).

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison,Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Manoj, E., Prathapachandra Kurup, M. R., Fun, H.-K. & Chantrapromma, S. (2005). Acta Cryst. E61, o4110–o4112. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wu, D.-Y., Sato, O., Einaga, Y. & Duan, C.-Y. (2009). Angew. Chem. Int. Ed. 48, 1475–1478. Web of Science CSD CrossRef CAS Google Scholar

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Volume 67| Part 8| August 2011| Page o1874

doi:10.1107/S1600536811025359

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-[({[Bis(pyridin-2-yl)methyl­idene]hydrazine­carbonyl}hydrazinyl­idene)(pyridin-2-yl)methyl]pyridinium tetra­fluoro­borate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-[({[Bis(pyridin-2-yl)methylidene]hydrazinecarbonyl}hydrazinylidene)(pyridin-2-yl)methyl]pyridinium tetrafluoroborate