5-Benzo­[c]-1,5-naphthyridinium bromide

Marciniak, B.; Pavlyuk, V.; Deska, M.

doi:10.1107/S1600536802005366

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5-Benzo[c]-1,5-naphthyridinium bromide

B. Marciniak, V. Pavlyuk and M. Deska

The title compound, C₁₂H₉N₂⁺·Br⁻, crystallizes in the triclinic system (P $\overline 1$ ); it is not isostructural with its chloride analogue, which is monoclinic, P2₁/c. As in the case of the earlier known azaaromatic chlorides and iodides, we also observed a short H

Br distance for the C—H

Br interaction.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802005366/na6143sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802005366/na6143Isup2.hkl Contains datablock I

CCDC reference: 185770

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R factor = 0.025
wR factor = 0.111
Data-to-parameter ratio = 16.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.42
         From the CIF: _reflns_number_total               2240
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         2428
         Completeness (_total/calc)             92.26%
          Alert C: < 95% complete

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.42
         From the CIF: _reflns_number_total               2240
         From the CIF: _diffrn_reflns_limit_ max hkl   11.   11.    6.
         From the CIF: _diffrn_reflns_limit_ min hkl  -11.  -11.    0.
         TEST1: Expected hkl limits for theta max
         Calculated maximum hkl   14.   12.    6.
         Calculated minimum hkl  -14.  -12.   -6.
          ALERT: Expected hkl max differ from CIF values


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

Comment top

During recent years, there has been considerable interest in the structure and properties of species obtained by combining protonated aromatic nitrogen bases with halide and polyhalide ions (Hensen et al., 2000; Hendrixson et al., 1991; Liu et al., 1991, 1992; Wang et al., 1999). The crystal structures are known for C₁₂H₉N₂⁺·Cl^- (Hensen et al., 2000), 3C₁₂H₉N₂⁺·2Cl^-·HCl·Cl^-·CHCl₃ (Hensen et al., 2000), 2C₁₂H₉N₂⁺·(I₂Cl)^-·(Cl₂I)^- (Wang et al., 1999a) and 2C₁₂H₁₀N₂⁺·(ClICl)^-·Cl^- (Wang et al., 1999b). For all these structures, short H···X (X = Cl, I) contacts to aromatic H atoms are found. Furthermore, the crystal packing is stabilized by several short X···H—C contacts (Hensen et al., 2000).

Experimental top

The title compound was synthesized by treatment of benzo[c]1,5-naphthyridine with 40% hydrobromic acid. Small yellow crystals were grown from solution in acetonitrile by slow evaporation of the solvent at a constant temperature of 293 K.

Computing details top

Data collection: DARCH software; cell refinement: DARCH software; data reduction: DARCH software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. The constituent ions of the C₁₂N₉N₂⁺·Br^- compound.
	Fig. 2. The unit-cell contents viewed along c.

5-benzo[c]1,5-naphthyridinium bromide top

Crystal data top

C₁₂H₉N₂⁺·Br⁻	Z = 2
M_r = 261.12	F(000) = 260
Triclinic, P1	D_x = 1.626 Mg m⁻³
a = 11.401 (2) Å	Mo Kα radiation, λ = 0.71069 Å
b = 9.605 (2) Å	Cell parameters from 46 reflections
c = 5.142 (1) Å	θ = 5.0–20.0°
α = 80.03 (3)°	µ = 3.82 mm⁻¹
β = 79.23 (3)°	T = 293 K
γ = 76.63 (3)°	Needle, clear pale yellow
V = 533.18 (18) Å³	0.32 × 0.09 × 0.03 mm

Data collection top

DARCH-1 diffractometer	2240 independent reflections
Radiation source: BSW x-ray tube	1544 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω–2θ scans	θ_max = 27.4°, θ_min = 2.2°
Absorption correction: empirical (using intensity measurements) (DIFABS; Walker & Stuart, 1983)	h = −11→11
T_min = 0.669, T_max = 0.892	k = −11→11
2240 measured reflections	l = 0→6

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 0.80	w = 1/[σ²(F_o²) + (0.05P)²] where P = (F_o² + 2F_c²)/3
2240 reflections	(Δ/σ)_max = 0.038
137 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₂H₉N₂⁺·Br⁻	γ = 76.63 (3)°
M_r = 261.12	V = 533.18 (18) Å³
Triclinic, P1	Z = 2
a = 11.401 (2) Å	Mo Kα radiation
b = 9.605 (2) Å	µ = 3.82 mm⁻¹
c = 5.142 (1) Å	T = 293 K
α = 80.03 (3)°	0.32 × 0.09 × 0.03 mm
β = 79.23 (3)°

Data collection top

DARCH-1 diffractometer	2240 independent reflections
Absorption correction: empirical (using intensity measurements) (DIFABS; Walker & Stuart, 1983)	1544 reflections with I > 2σ(I)
T_min = 0.669, T_max = 0.892	R_int = 0.021
2240 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 0.80	Δρ_max = 0.34 e Å⁻³
2240 reflections	Δρ_min = −0.30 e Å⁻³
137 parameters

Special details top

Experimental. The DIFABS absorption correction (Stuart & Walker, 1983) was found to have no significant effect on the refinement results

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
Br1	0.69051 (4)	0.11332 (5)	0.08397 (9)	0.1001 (2)
N1	0.2650 (3)	0.1280 (4)	0.2938 (7)	0.0927 (9)
H1	0.2780	0.0673	0.1816	0.111 (5)*
N2	0.0083 (3)	0.3423 (4)	0.6928 (7)	0.0977 (9)
C1	0.1459 (4)	0.1881 (4)	0.3927 (8)	0.0839 (9)
C2	0.0487 (4)	0.1491 (5)	0.3087 (9)	0.0993 (11)
H2	0.0618	0.0863	0.1824	0.111 (5)*
C3	−0.0667 (4)	0.2091 (5)	0.4241 (11)	0.1073 (14)
H3	−0.1349	0.1878	0.3774	0.111 (5)*
C4	−0.0798 (4)	0.3016 (5)	0.6105 (11)	0.1061 (13)
H4	−0.1592	0.3391	0.6858	0.111 (5)*
C5	0.1237 (4)	0.2830 (4)	0.5815 (8)	0.0871 (10)
C6	0.2247 (4)	0.3244 (4)	0.6547 (7)	0.0846 (9)
C7	0.2123 (4)	0.4263 (4)	0.8267 (9)	0.0946 (11)
H7	0.1354	0.4708	0.9040	0.111 (5)*
C8	0.3145 (5)	0.4599 (5)	0.8800 (10)	0.1090 (13)
H8	0.3054	0.5315	0.9873	0.111 (5)*
C9	0.4300 (5)	0.3924 (6)	0.7818 (10)	0.1100 (14)
H9	0.4974	0.4141	0.8313	0.111 (5)*
C10	0.4454 (4)	0.2943 (5)	0.6130 (9)	0.0993 (11)
H10	0.5235	0.2501	0.5421	0.111 (5)*
C11	0.3442 (4)	0.2596 (4)	0.5453 (7)	0.0853 (9)
C12	0.3580 (4)	0.1605 (5)	0.3655 (8)	0.0912 (10)
H12	0.4363	0.1165	0.2949	0.111 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0969 (3)	0.1042 (3)	0.1005 (3)	−0.0219 (2)	−0.0135 (2)	−0.0178 (2)
N1	0.102 (2)	0.0898 (19)	0.0827 (19)	−0.0130 (17)	−0.0132 (17)	−0.0128 (16)
N2	0.087 (2)	0.104 (2)	0.097 (2)	−0.0171 (17)	−0.0090 (18)	−0.0066 (19)
C1	0.092 (2)	0.079 (2)	0.078 (2)	−0.0148 (18)	−0.0176 (18)	0.0006 (17)
C2	0.107 (3)	0.098 (3)	0.095 (3)	−0.025 (2)	−0.023 (2)	−0.006 (2)
C3	0.088 (3)	0.103 (3)	0.131 (4)	−0.029 (2)	−0.033 (3)	0.014 (3)
C4	0.087 (3)	0.104 (3)	0.115 (3)	−0.009 (2)	−0.013 (3)	0.001 (3)
C5	0.091 (2)	0.082 (2)	0.079 (2)	−0.0143 (17)	−0.0151 (18)	0.0118 (17)
C6	0.094 (2)	0.086 (2)	0.0714 (19)	−0.0155 (18)	−0.0127 (17)	−0.0068 (17)
C7	0.097 (3)	0.093 (2)	0.087 (2)	−0.011 (2)	−0.011 (2)	−0.009 (2)
C8	0.126 (4)	0.103 (3)	0.100 (3)	−0.017 (3)	−0.022 (3)	−0.022 (2)
C9	0.102 (3)	0.125 (3)	0.113 (3)	−0.031 (3)	−0.018 (3)	−0.030 (3)
C10	0.097 (3)	0.107 (3)	0.096 (3)	−0.025 (2)	−0.017 (2)	−0.013 (2)
C11	0.095 (3)	0.095 (2)	0.0684 (18)	−0.0227 (19)	−0.0166 (17)	−0.0094 (17)
C12	0.087 (3)	0.104 (3)	0.080 (2)	−0.014 (2)	−0.0137 (19)	−0.011 (2)

Geometric parameters (Å, º) top

Br1—Br1	0.0000 (13)	C5—C6	1.432 (6)
N1—C12	1.303 (5)	C6—C7	1.397 (6)
N1—C1	1.385 (5)	C6—C11	1.415 (5)
N1—H1	0.8600	C7—C8	1.363 (6)
N2—C4	1.318 (6)	C7—H7	0.9300
N2—C5	1.367 (5)	C8—C9	1.371 (7)
C1—C5	1.395 (6)	C8—H8	0.9300
C1—C2	1.407 (6)	C9—C10	1.350 (6)
C2—C3	1.376 (6)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.390 (6)
C3—C4	1.382 (7)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.402 (5)
C4—H4	0.9300	C12—H12	0.9300

C12—N1—C1	122.1 (4)	C7—C6—C5	123.8 (4)
C12—N1—H1	119.0	C11—C6—C5	118.4 (4)
C1—N1—H1	119.0	C8—C7—C6	119.2 (4)
C4—N2—C5	114.9 (4)	C8—C7—H7	120.4
N1—C1—C5	119.5 (4)	C6—C7—H7	120.4
N1—C1—C2	119.7 (4)	C7—C8—C9	122.6 (5)
C5—C1—C2	120.8 (4)	C7—C8—H8	118.7
C3—C2—C1	116.1 (4)	C9—C8—H8	118.7
C3—C2—H2	121.9	C10—C9—C8	119.7 (5)
C1—C2—H2	121.9	C10—C9—H9	120.1
C2—C3—C4	119.0 (4)	C8—C9—H9	120.1
C2—C3—H3	120.5	C9—C10—C11	119.9 (4)
C4—C3—H3	120.5	C9—C10—H10	120.1
N2—C4—C3	126.9 (4)	C11—C10—H10	120.1
N2—C4—H4	116.6	C10—C11—C12	120.8 (4)
C3—C4—H4	116.6	C10—C11—C6	120.7 (4)
N2—C5—C1	122.2 (4)	C12—C11—C6	118.4 (4)
N2—C5—C6	118.6 (4)	N1—C12—C11	122.3 (4)
C1—C5—C6	119.2 (4)	N1—C12—H12	118.9
C7—C6—C11	117.8 (4)	C11—C12—H12	118.9

C12—N1—C1—C5	−2.1 (5)	C1—C5—C6—C11	−4.2 (5)
C12—N1—C1—C2	−179.9 (4)	C11—C6—C7—C8	0.5 (6)
N1—C1—C2—C3	177.5 (4)	C5—C6—C7—C8	−178.9 (4)
C5—C1—C2—C3	−0.3 (6)	C6—C7—C8—C9	−3.3 (7)
C1—C2—C3—C4	0.0 (6)	C7—C8—C9—C10	3.9 (8)
C5—N2—C4—C3	−1.2 (7)	C8—C9—C10—C11	−1.7 (7)
C2—C3—C4—N2	0.8 (7)	C9—C10—C11—C12	178.5 (4)
C4—N2—C5—C1	0.8 (6)	C9—C10—C11—C6	−1.0 (6)
C4—N2—C5—C6	178.4 (3)	C7—C6—C11—C10	1.5 (6)
N1—C1—C5—N2	−177.9 (3)	C5—C6—C11—C10	−179.0 (3)
C2—C1—C5—N2	−0.1 (6)	C7—C6—C11—C12	−177.9 (3)
N1—C1—C5—C6	4.5 (5)	C5—C6—C11—C12	1.5 (5)
C2—C1—C5—C6	−177.7 (3)	C1—N1—C12—C11	−0.7 (6)
N2—C5—C6—C7	−2.4 (6)	C10—C11—C12—N1	−178.5 (4)
C1—C5—C6—C7	175.3 (3)	C6—C11—C12—N1	0.9 (6)
N2—C5—C6—C11	178.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Br1ⁱ	0.86	2.31	3.171 (4)	174
C12—H12···Br1	0.93	2.89	3.749 (4)	154

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₂H₉N₂⁺·Br⁻
M_r	261.12
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	11.401 (2), 9.605 (2), 5.142 (1)
α, β, γ (°)	80.03 (3), 79.23 (3), 76.63 (3)
V (Å³)	533.18 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.82
Crystal size (mm)	0.32 × 0.09 × 0.03

Data collection
Diffractometer	DARCH-1 diffractometer
Absorption correction	Empirical (using intensity measurements) (DIFABS; Walker & Stuart, 1983)
T_min, T_max	0.669, 0.892
No. of measured, independent and observed [I > 2σ(I)] reflections	2240, 2240, 1544
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.111, 0.80
No. of reflections	2240
No. of parameters	137
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.30

Computer programs: DARCH software, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2000), SHELXL97.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Br1ⁱ	0.86	2.31	3.171 (4)	174
C12—H12···Br1	0.93	2.89	3.749 (4)	154

Symmetry code: (i) −x+1, −y, −z.

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