1-Allyl-4-amino­pyridinium bromide

Seethalakshmi, T.; Venkatesan, P.; Butcher, R.J.; Nallu, M.; Kaliannan, P.

doi:10.1107/S160053680603875X

1-Allyl-4-aminopyridinium bromide

T. Seethalakshmi, P. Venkatesan, R. J. Butcher, M. Nallu and P. Kaliannan

The asymmetric unit of the title structure, C₈H₁₁N₂⁺·Br⁻, contains two independent cations and two anions. In one cation, the dihedral angle between the mean planes of the pyridinium ring and the allyl group is 86.43 (6)°, while in the other cation this dihedral angle is 72.93 (7)°. In the crystal structure, anions and cations are linked via intermolecular N—H

Br hydrogen bonds, forming one-dimensional chains along [010].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603875X/lh2184sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680603875X/lh2184Isup2.hkl Contains datablock I

CCDC reference: 624919

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.009 Å
R factor = 0.064
wR factor = 0.164
Data-to-parameter ratio = 23.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         12

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXL97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

1-Allyl-4-aminopyridinium bromide top

Crystal data top

C₈H₁₁N₂⁺·Br⁻	Z = 4
M_r = 215.10	F(000) = 432
Triclinic, P1	D_x = 1.606 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9085 (19) Å	Cell parameters from 2476 reflections
b = 9.179 (3) Å	θ = 3.0–27.6°
c = 14.186 (4) Å	µ = 4.56 mm⁻¹
α = 90.096 (4)°	T = 293 K
β = 97.446 (4)°	Block, colourless
γ = 94.164 (4)°	0.49 × 0.32 × 0.26 mm
V = 889.6 (5) Å³

Data collection top

Bruker APEX-2 CCD area-detector diffractometer	4585 independent reflections
Radiation source: fine-focus sealed tube	3443 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
φ and ω scans	θ_max = 28.9°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.171, T_max = 0.307	k = −12→12
9293 measured reflections	l = 0→19

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0581P)² + 8.4291P] where P = (F_o² + 2F_c²)/3
4585 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 1.98 e Å⁻³
0 restraints	Δρ_min = −1.25 e Å⁻³

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
N1A	0.8152 (8)	0.8349 (6)	0.1140 (4)	0.0188 (10)
N2A	0.6904 (8)	1.0354 (6)	−0.1439 (4)	0.0222 (11)
H2A1	0.6769	1.1278	−0.1443	0.027*
H2A2	0.6781	0.9871	−0.1966	0.027*
C1A	0.7953 (9)	0.9792 (7)	0.1090 (5)	0.0213 (13)
H1A	0.8127	1.0341	0.1650	0.026*
C2A	0.7502 (9)	1.0484 (7)	0.0241 (5)	0.0199 (12)
H2A	0.7327	1.1479	0.0229	0.024*
C3A	0.7308 (9)	0.9666 (7)	−0.0612 (5)	0.0212 (13)
C4A	0.7525 (9)	0.8146 (7)	−0.0539 (5)	0.0230 (13)
H4A	0.7380	0.7566	−0.1085	0.028*
C5A	0.7941 (9)	0.7542 (7)	0.0319 (5)	0.0207 (12)
H5A	0.8089	0.6544	0.0354	0.025*
C6A	0.8683 (11)	0.7693 (8)	0.2098 (5)	0.0263 (14)
H6A1	0.8854	0.6662	0.2022	0.032*
H6A2	0.9916	0.8161	0.2395	0.032*
C7A	0.7145 (10)	0.7872 (7)	0.2724 (5)	0.0259 (14)
H7A	0.5887	0.7460	0.2529	0.031*
C8A	0.7479 (11)	0.8577 (7)	0.3528 (5)	0.0260 (14)
H8A1	0.8726	0.8999	0.3738	0.031*
H8A2	0.6470	0.8661	0.3896	0.031*
N1B	0.7435 (7)	0.3245 (5)	0.4124 (4)	0.0167 (10)
N2B	0.7598 (8)	0.5437 (6)	0.6664 (4)	0.0211 (11)
H2B1	0.7694	0.6377	0.6672	0.025*
H2B2	0.7561	0.4966	0.7186	0.025*
C1B	0.7382 (9)	0.2481 (7)	0.4937 (5)	0.0204 (12)
H1B	0.7321	0.1466	0.4912	0.024*
C2B	0.7417 (8)	0.3167 (7)	0.5786 (4)	0.0178 (12)
H2B	0.7381	0.2619	0.6335	0.021*
C3B	0.7507 (8)	0.4713 (6)	0.5846 (4)	0.0160 (11)
C4B	0.7567 (8)	0.5475 (7)	0.4983 (4)	0.0159 (11)
H4B	0.7633	0.6491	0.4986	0.019*
C5B	0.7530 (8)	0.4736 (6)	0.4153 (4)	0.0155 (11)
H5B	0.7569	0.5254	0.3592	0.019*
C6B	0.7481 (10)	0.2448 (7)	0.3211 (5)	0.0206 (12)
H6B1	0.8823	0.2253	0.3156	0.025*
H6B2	0.6731	0.1515	0.3227	0.025*
C7B	0.6686 (11)	0.3256 (7)	0.2361 (5)	0.0267 (14)
H7B	0.5409	0.3528	0.2328	0.032*
C8B	0.7665 (12)	0.3616 (7)	0.1647 (5)	0.0307 (16)
H8B1	0.8946	0.3361	0.1656	0.037*
H8B2	0.7075	0.4125	0.1134	0.037*
Br1	0.27604 (9)	0.59387 (6)	0.11717 (4)	0.02016 (17)
Br2	0.25624 (9)	0.09134 (6)	0.36364 (4)	0.01973 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.023 (3)	0.022 (3)	0.014 (3)	0.004 (2)	0.008 (2)	0.004 (2)
N2A	0.027 (3)	0.024 (3)	0.015 (3)	0.001 (2)	0.002 (2)	0.003 (2)
C1A	0.027 (3)	0.020 (3)	0.018 (3)	0.002 (2)	0.007 (2)	0.000 (2)
C2A	0.027 (3)	0.018 (3)	0.016 (3)	0.006 (2)	0.004 (2)	0.001 (2)
C3A	0.017 (3)	0.020 (3)	0.028 (4)	−0.001 (2)	0.006 (2)	0.001 (2)
C4A	0.023 (3)	0.020 (3)	0.025 (3)	−0.001 (2)	0.002 (3)	−0.007 (2)
C5A	0.020 (3)	0.016 (3)	0.026 (3)	0.003 (2)	0.005 (2)	−0.002 (2)
C6A	0.036 (4)	0.025 (3)	0.019 (3)	0.010 (3)	0.005 (3)	0.009 (3)
C7A	0.025 (3)	0.025 (3)	0.027 (4)	0.001 (3)	0.000 (3)	0.007 (3)
C8A	0.031 (4)	0.024 (3)	0.024 (4)	0.001 (3)	0.009 (3)	0.004 (3)
N1B	0.019 (2)	0.019 (2)	0.013 (2)	0.0034 (19)	0.0032 (19)	0.0027 (19)
N2B	0.033 (3)	0.018 (2)	0.011 (2)	0.001 (2)	0.002 (2)	−0.0016 (19)
C1B	0.024 (3)	0.017 (3)	0.021 (3)	0.001 (2)	0.007 (2)	0.005 (2)
C2B	0.015 (3)	0.022 (3)	0.016 (3)	0.006 (2)	−0.003 (2)	0.010 (2)
C3B	0.012 (2)	0.021 (3)	0.013 (3)	0.001 (2)	−0.003 (2)	0.002 (2)
C4B	0.017 (3)	0.019 (3)	0.012 (3)	0.002 (2)	−0.001 (2)	0.001 (2)
C5B	0.020 (3)	0.012 (3)	0.015 (3)	0.001 (2)	0.007 (2)	0.003 (2)
C6B	0.029 (3)	0.015 (3)	0.018 (3)	0.003 (2)	0.005 (2)	−0.004 (2)
C7B	0.033 (4)	0.027 (3)	0.020 (3)	0.006 (3)	0.002 (3)	−0.001 (3)
C8B	0.053 (5)	0.019 (3)	0.019 (3)	−0.003 (3)	0.005 (3)	−0.005 (3)
Br1	0.0300 (3)	0.0180 (3)	0.0120 (3)	0.0021 (2)	0.0011 (2)	0.0011 (2)
Br2	0.0255 (3)	0.0175 (3)	0.0165 (3)	0.0018 (2)	0.0037 (2)	0.0010 (2)

Geometric parameters (Å, º) top

N1A—C1A	1.343 (8)	N1B—C1B	1.354 (8)
N1A—C5A	1.365 (8)	N1B—C5B	1.366 (7)
N1A—C6A	1.500 (8)	N1B—C6B	1.491 (8)
N2A—C3A	1.341 (9)	N2B—C3B	1.328 (8)
N2A—H2A1	0.8600	N2B—H2B1	0.8600
N2A—H2A2	0.8600	N2B—H2B2	0.8600
C1A—C2A	1.373 (9)	C1B—C2B	1.355 (9)
C1A—H1A	0.9300	C1B—H1B	0.9300
C2A—C3A	1.409 (9)	C2B—C3B	1.418 (8)
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—C4A	1.417 (9)	C3B—C4B	1.415 (8)
C4A—C5A	1.343 (10)	C4B—C5B	1.354 (8)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C7A	1.487 (10)	C6B—C7B	1.483 (9)
C6A—H6A1	0.9700	C6B—H6B1	0.9700
C6A—H6A2	0.9700	C6B—H6B2	0.9700
C7A—C8A	1.297 (10)	C7B—C8B	1.318 (10)
C7A—H7A	0.9300	C7B—H7B	0.9300
C8A—H8A1	0.9300	C8B—H8B1	0.9300
C8A—H8A2	0.9300	C8B—H8B2	0.9300

C1A—N1A—C5A	119.1 (5)	C1B—N1B—C5B	119.8 (5)
C1A—N1A—C6A	118.5 (5)	C1B—N1B—C6B	119.4 (5)
C5A—N1A—C6A	122.4 (5)	C5B—N1B—C6B	120.7 (5)
C3A—N2A—H2A1	120.0	C3B—N2B—H2B1	120.0
C3A—N2A—H2A2	120.0	C3B—N2B—H2B2	120.0
H2A1—N2A—H2A2	120.0	H2B1—N2B—H2B2	120.0
N1A—C1A—C2A	122.3 (6)	N1B—C1B—C2B	121.2 (6)
N1A—C1A—H1A	118.9	N1B—C1B—H1B	119.4
C2A—C1A—H1A	118.9	C2B—C1B—H1B	119.4
C1A—C2A—C3A	119.1 (6)	C1B—C2B—C3B	120.7 (6)
C1A—C2A—H2A	120.5	C1B—C2B—H2B	119.7
C3A—C2A—H2A	120.5	C3B—C2B—H2B	119.7
N2A—C3A—C2A	118.8 (6)	N2B—C3B—C4B	120.5 (6)
N2A—C3A—C4A	123.7 (6)	N2B—C3B—C2B	122.9 (6)
C2A—C3A—C4A	117.4 (6)	C4B—C3B—C2B	116.5 (5)
C5A—C4A—C3A	120.1 (6)	C5B—C4B—C3B	120.5 (6)
C5A—C4A—H4A	120.0	C5B—C4B—H4B	119.8
C3A—C4A—H4A	120.0	C3B—C4B—H4B	119.8
C4A—C5A—N1A	122.0 (6)	C4B—C5B—N1B	121.3 (5)
C4A—C5A—H5A	119.0	C4B—C5B—H5B	119.4
N1A—C5A—H5A	119.0	N1B—C5B—H5B	119.4
C7A—C6A—N1A	111.3 (5)	C7B—C6B—N1B	113.6 (5)
C7A—C6A—H6A1	109.4	C7B—C6B—H6B1	108.9
N1A—C6A—H6A1	109.4	N1B—C6B—H6B1	108.9
C7A—C6A—H6A2	109.4	C7B—C6B—H6B2	108.9
N1A—C6A—H6A2	109.4	N1B—C6B—H6B2	108.9
H6A1—C6A—H6A2	108.0	H6B1—C6B—H6B2	107.7
C8A—C7A—C6A	123.0 (7)	C8B—C7B—C6B	124.5 (7)
C8A—C7A—H7A	118.5	C8B—C7B—H7B	117.7
C6A—C7A—H7A	118.5	C6B—C7B—H7B	117.7
C7A—C8A—H8A1	120.0	C7B—C8B—H8B1	120.0
C7A—C8A—H8A2	120.0	C7B—C8B—H8B2	120.0
H8A1—C8A—H8A2	120.0	H8B1—C8B—H8B2	120.0

C5A—N1A—C1A—C2A	1.4 (9)	C5B—N1B—C1B—C2B	0.1 (9)
C6A—N1A—C1A—C2A	178.9 (6)	C6B—N1B—C1B—C2B	177.4 (6)
N1A—C1A—C2A—C3A	−2.3 (10)	N1B—C1B—C2B—C3B	0.1 (9)
C1A—C2A—C3A—N2A	−178.7 (6)	C1B—C2B—C3B—N2B	−178.1 (6)
C1A—C2A—C3A—C4A	2.2 (9)	C1B—C2B—C3B—C4B	−0.3 (8)
N2A—C3A—C4A—C5A	179.6 (6)	N2B—C3B—C4B—C5B	178.1 (6)
C2A—C3A—C4A—C5A	−1.4 (9)	C2B—C3B—C4B—C5B	0.3 (8)
C3A—C4A—C5A—N1A	0.5 (10)	C3B—C4B—C5B—N1B	−0.1 (9)
C1A—N1A—C5A—C4A	−0.5 (9)	C1B—N1B—C5B—C4B	−0.2 (9)
C6A—N1A—C5A—C4A	−177.9 (6)	C6B—N1B—C5B—C4B	−177.4 (6)
C1A—N1A—C6A—C7A	62.5 (8)	C1B—N1B—C6B—C7B	154.8 (6)
C5A—N1A—C6A—C7A	−120.1 (7)	C5B—N1B—C6B—C7B	−28.0 (8)
N1A—C6A—C7A—C8A	−120.0 (7)	N1B—C6B—C7B—C8B	122.5 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2A1···Br1ⁱ	0.86	2.57	3.411 (6)	165
N2A—H2A2···Br2ⁱⁱ	0.86	2.58	3.399 (6)	159
N2B—H2B1···Br2ⁱⁱⁱ	0.86	2.54	3.386 (5)	167
N2B—H2B2···Br1ⁱⁱⁱ	0.86	2.51	3.354 (6)	169

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

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1-Allyl-4-amino­pyridinium bromide

Supporting information

Key indicators

checkCIF/PLATON results

1-Allyl-4-aminopyridinium bromide