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The title compound, C9H14N+·Br, was synthesized by the reaction of pyridine and n-butyl bromide. The crystal packing is stabilized by inter­molecular C—H...Br hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806000353/ci6733sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806000353/ci6733Isup2.hkl
Contains datablock I

CCDC reference: 298391

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.020 Å
  • Disorder in main residue
  • R factor = 0.047
  • wR factor = 0.138
  • Data-to-parameter ratio = 8.4

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 24.93 Deg.
Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C1' PLAT341_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 20
Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2 PLAT301_ALERT_3_C Main Residue Disorder ......................... 21.00 Perc. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 7
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 24.93 From the CIF: _reflns_number_total 1072 Count of symmetry unique reflns 1074 Completeness (_total/calc) 99.81% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

N-n-butylpyridinium bromide top
Crystal data top
C9H14N+·BrF(000) = 440
Mr = 216.12Dx = 1.370 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 8.3040 (17) Åθ = 10–13°
b = 10.783 (2) ŵ = 3.87 mm1
c = 11.699 (2) ÅT = 293 K
V = 1047.6 (3) Å3Block, colourless
Z = 40.40 × 0.30 × 0.20 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
641 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 24.9°, θmin = 2.6°
ω/2θ scansh = 09
Absorption correction: ψ scan
(North et al., 1968)
k = 012
Tmin = 0.276, Tmax = 0.461l = 013
1072 measured reflections3 standard reflections every 200 reflections
1072 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.138 w = 1/[σ2(Fo2) + (0.0758P)2 + 0.5P]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max = 0.001
1072 reflectionsΔρmax = 0.36 e Å3
127 parametersΔρmin = 0.51 e Å3
42 restraintsAbsolute structure: Flack (1983); 0 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (6)
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
xyzUiso*/UeqOcc. (<1)
Br10.97562 (13)0.28210 (12)0.39186 (10)0.0616 (4)
N10.6028 (12)0.4970 (10)0.2147 (9)0.057 (3)
C10.750 (4)0.267 (3)0.089 (3)0.088 (10)0.50
H1A0.67030.24960.14630.132*0.50
H1B0.77540.19240.04830.132*0.50
H1C0.84490.29940.12450.132*0.50
C20.683 (3)0.363 (2)0.0055 (17)0.070 (7)0.50
H2A0.58280.33250.02690.084*0.50
H2B0.66010.43930.04590.084*0.50
C30.804 (3)0.388 (2)0.090 (2)0.072 (9)0.50
H3A0.80960.31430.13790.086*0.50
H3B0.90880.39940.05590.086*0.50
C1'0.743 (6)0.229 (4)0.056 (3)0.118 (16)0.50
H1'A0.72280.14260.04390.178*0.50
H1'B0.84410.23980.09420.178*0.50
H1'C0.65820.26400.10170.178*0.50
C2'0.748 (4)0.296 (2)0.060 (2)0.087 (9)0.50
H2'A0.82710.25490.10760.104*0.50
H2'B0.64390.28670.09620.104*0.50
C3'0.789 (4)0.434 (2)0.0534 (18)0.084 (11)0.50
H3'A0.89930.44300.02720.101*0.50
H3'B0.71930.47330.00220.101*0.50
C40.7704 (18)0.4987 (15)0.1678 (13)0.095 (5)
H4A0.84660.49820.23070.114*0.50
H4B0.78650.57470.12490.114*0.50
H4C0.84370.46150.22120.114*0.50
H4D0.80180.58360.15680.114*0.50
C50.5695 (16)0.4232 (12)0.3036 (10)0.058 (3)
H50.65170.37590.33550.069*
C60.4214 (19)0.4156 (13)0.3480 (11)0.073 (4)
H60.39950.36530.41070.087*
C70.3030 (18)0.4854 (15)0.2971 (13)0.082 (4)
H70.19790.48070.32410.099*
C80.3378 (19)0.5613 (15)0.2078 (14)0.085 (5)
H80.25830.61150.17620.103*
C90.490 (2)0.5631 (11)0.1651 (10)0.074 (4)
H90.51360.61090.10120.089*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0563 (6)0.0669 (7)0.0617 (6)0.0017 (6)0.0001 (6)0.0046 (7)
N10.049 (6)0.057 (7)0.067 (7)0.015 (6)0.014 (6)0.011 (6)
C10.090 (13)0.088 (13)0.086 (13)0.009 (9)0.003 (9)0.002 (10)
C20.076 (11)0.064 (11)0.069 (10)0.005 (9)0.006 (9)0.000 (9)
C30.063 (11)0.084 (12)0.068 (11)0.002 (9)0.005 (9)0.007 (9)
C1'0.116 (18)0.123 (18)0.116 (18)0.004 (10)0.016 (10)0.000 (10)
C2'0.087 (11)0.091 (12)0.083 (12)0.003 (9)0.007 (9)0.005 (9)
C3'0.080 (14)0.083 (14)0.089 (14)0.000 (9)0.007 (9)0.012 (10)
C40.074 (11)0.097 (11)0.115 (13)0.040 (9)0.021 (10)0.022 (11)
C50.073 (9)0.055 (8)0.045 (7)0.000 (7)0.009 (7)0.012 (6)
C60.099 (11)0.071 (10)0.048 (8)0.024 (8)0.019 (7)0.017 (7)
C70.065 (11)0.096 (12)0.086 (10)0.018 (9)0.007 (9)0.027 (10)
C80.075 (11)0.088 (12)0.093 (11)0.018 (9)0.027 (9)0.015 (10)
C90.110 (13)0.051 (8)0.060 (7)0.023 (10)0.007 (9)0.015 (6)
Geometric parameters (Å, º) top
N1—C91.314 (15)C2'—H2'A0.97
N1—C51.339 (15)C2'—H2'B0.97
N1—C41.496 (16)C3'—C41.519 (10)
C1—C21.523 (10)C3'—H3'A0.97
C1—H1A0.96C3'—H3'B0.97
C1—H1B0.96C4—H4A0.97
C1—H1C0.96C4—H4B0.97
C2—C31.528 (10)C4—H4C0.96
C2—H2A0.97C4—H4D0.96
C2—H2B0.97C5—C61.337 (18)
C3—C41.525 (10)C5—H50.93
C3—H3A0.97C6—C71.374 (19)
C3—H3B0.97C6—H60.93
C1'—C2'1.528 (10)C7—C81.36 (2)
C1'—H1'A0.96C7—H70.93
C1'—H1'B0.96C8—C91.357 (17)
C1'—H1'C0.96C8—H80.93
C2'—C3'1.528 (10)C9—H90.93
C9—N1—C5121.2 (10)C2'—C3'—H3'A109.1
C9—N1—C4119.8 (13)C4—C3'—H3'B109.1
C5—N1—C4119.0 (13)C2'—C3'—H3'B109.1
C2—C1—H1A109.5H3'A—C3'—H3'B107.8
C2—C1—H1B109.5N1—C4—C3'114.3 (17)
H1A—C1—H1B109.5N1—C4—C3112.1 (14)
C2—C1—H1C109.5N1—C4—H4A109.2
H1A—C1—H1C109.5C3'—C4—H4A126.8
H1B—C1—H1C109.5C3—C4—H4A109.2
C1—C2—C3110.6 (19)N1—C4—H4B109.2
C1—C2—H2A109.5C3'—C4—H4B85.4
C3—C2—H2A109.5C3—C4—H4B109.2
C1—C2—H2B109.5H4A—C4—H4B107.9
C3—C2—H2B109.5N1—C4—H4C110.3
H2A—C2—H2B108.1C3'—C4—H4C108.4
C4—C3—C2117.2 (17)C3—C4—H4C86.8
C4—C3—H3A108.0N1—C4—H4D108.3
C2—C3—H3A108.0C3'—C4—H4D107.1
C4—C3—H3B108.0C3—C4—H4D128.2
C2—C3—H3B108.0H4C—C4—H4D108.3
H3A—C3—H3B107.2C6—C5—N1121.9 (12)
C2'—C1'—H1'A109.5C6—C5—H5119.1
C2'—C1'—H1'B109.5N1—C5—H5119.1
H1'A—C1'—H1'B109.5C5—C6—C7117.1 (12)
C2'—C1'—H1'C109.5C5—C6—H6121.4
H1'A—C1'—H1'C109.5C7—C6—H6121.4
H1'B—C1'—H1'C109.5C8—C7—C6120.8 (14)
C1'—C2'—C3'115 (2)C8—C7—H7119.6
C1'—C2'—H2'A108.5C6—C7—H7119.6
C3'—C2'—H2'A108.5C9—C8—C7119.3 (14)
C1'—C2'—H2'B108.5C9—C8—H8120.3
C3'—C2'—H2'B108.5C7—C8—H8120.3
H2'A—C2'—H2'B107.5N1—C9—C8119.6 (12)
C4—C3'—C2'112.6 (19)N1—C9—H9120.2
C4—C3'—H3'A109.1C8—C9—H9120.2
C1—C2—C3—C4168 (2)C2—C3—C4—C3'49 (4)
C1'—C2'—C3'—C4172 (3)C9—N1—C5—C62 (2)
C9—N1—C4—C3'70 (2)C4—N1—C5—C6178.7 (12)
C5—N1—C4—C3'107.0 (18)N1—C5—C6—C71 (2)
C9—N1—C4—C397.5 (19)C5—C6—C7—C82 (2)
C5—N1—C4—C379.5 (19)C6—C7—C8—C93 (2)
C2'—C3'—C4—N162 (3)C5—N1—C9—C83.0 (19)
C2'—C3'—C4—C329 (3)C4—N1—C9—C8179.9 (13)
C2—C3—C4—N151 (3)C7—C8—C9—N14 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4D···Br1i0.962.883.778 (16)155
C6—H6···Br1ii0.932.873.743 (13)156
C8—H8···Br1iii0.932.793.715 (16)172
C9—H9···Br1iv0.932.713.618 (12)166
Symmetry codes: (i) x+2, y+1/2, z+1/2; (ii) x1/2, y+1/2, z+1; (iii) x+1, y+1/2, z+1/2; (iv) x+3/2, y+1, z1/2.
 

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