N-Benzyl-4-(hydroxy­imino­meth­yl)pyridinium bromide

Odžak, R.; Halasz, I.; Tomić, S.; Čalogović, D.M.

doi:10.1107/S1600536806018356

N-Benzyl-4-(hydroxyiminomethyl)pyridinium bromide

R. Odžak, I. Halasz, S. Tomić and D. M. Čalogović

The title compound, C₁₃H₁₃N₂O⁺·Br⁻, is a quaternary derivative of 4-(hydroxyiminomethyl)pyridine. The oxime adopts the E configuration and is involved in an O—H

Br hydrogen bond. Cations are linked by C—H

π interactions into dimers.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806018356/kp2018sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806018356/kp2018Isup2.hkl Contains datablock I

CCDC reference: 610828

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.004 Å
R factor = 0.032
wR factor = 0.080
Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.65 mm
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              Br

Alert level G
ABSTM02_ALERT_3_G  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.356     0.569
            Tmin and Tmax expected:      0.200     0.394
            RR =      1.231
            Please check that your absorption correction is appropriate.

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

   0 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

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and SCHAKAL99 (Keller, 1999); software used to prepare material for publication: SHELXL97.

(I) top

Crystal data top

C₁₃H₁₃N₂O⁺·Br⁻	F(000) = 592
M_r = 293.16	D_x = 1.479 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 915 reflections
a = 10.365 (2) Å	θ = 2.6–20.7°
b = 9.556 (2) Å	µ = 3.11 mm⁻¹
c = 13.297 (3) Å	T = 295 K
β = 90.918 (16)°	Rounded block, colourless
V = 1316.9 (5) Å³	0.65 × 0.45 × 0.30 mm
Z = 4

Data collection top

Xcalibur CCD diffractometer	2571 independent reflections
Radiation source: fine-focus sealed tube	1851 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 26.1°, θ_min = 4.2°
Absorption correction: analytical (Alcock, 1970)	h = −12→12
T_min = 0.356, T_max = 0.569	k = −11→8
4817 measured reflections	l = −16→16

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.0431P)²] where P = (F_o² + 2F_c²)/3
2571 reflections	(Δ/σ)_max = 0.002
158 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.29 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
O1	−0.1988 (2)	0.7256 (3)	0.89288 (19)	0.0799 (8)
H1O	−0.212 (4)	0.773 (5)	0.943 (3)	0.115 (17)*
Br1	−0.29284 (3)	0.92022 (3)	1.06854 (2)	0.05522 (14)
N1	0.2742 (2)	0.7934 (2)	0.60940 (14)	0.0428 (5)
C3	0.0536 (2)	0.7434 (3)	0.71534 (18)	0.0416 (6)
C8	0.3858 (2)	0.8650 (3)	0.45190 (18)	0.0421 (6)
C9	0.4731 (3)	0.8169 (3)	0.38219 (19)	0.0488 (7)
H9	0.5311	0.7467	0.4002	0.059*
C2	0.1480 (2)	0.8329 (3)	0.75186 (18)	0.0436 (6)
H2	0.1370	0.8773	0.8134	0.052*
N2	−0.0836 (2)	0.7713 (3)	0.85407 (17)	0.0540 (6)
C6	−0.0632 (3)	0.7122 (3)	0.7701 (2)	0.0523 (7)
H6	−0.1230	0.6490	0.7437	0.063*
C1	0.2569 (2)	0.8566 (3)	0.69865 (18)	0.0451 (6)
H1	0.3198	0.9168	0.7241	0.054*
C7	0.3997 (2)	0.8091 (3)	0.55740 (19)	0.0532 (7)
H7A	0.4422	0.7188	0.5552	0.064*
H7B	0.4546	0.8719	0.5963	0.064*
C5	0.1847 (3)	0.7084 (3)	0.57133 (19)	0.0537 (8)
H5	0.1979	0.6663	0.5093	0.064*
C4	0.0737 (3)	0.6818 (3)	0.6218 (2)	0.0553 (8)
H4	0.0115	0.6228	0.5938	0.066*
C12	0.3007 (4)	1.0208 (4)	0.3270 (3)	0.0748 (10)
H12	0.2419	1.0897	0.3078	0.090*
C10	0.4748 (3)	0.8717 (4)	0.2869 (2)	0.0635 (9)
H10	0.5354	0.8402	0.2412	0.076*
C13	0.2999 (3)	0.9676 (4)	0.4243 (2)	0.0600 (8)
H13	0.2413	1.0015	0.4705	0.072*
C11	0.3886 (4)	0.9715 (4)	0.2591 (2)	0.0729 (10)
H11	0.3887	1.0068	0.1939	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0638 (15)	0.101 (2)	0.0765 (16)	−0.0256 (13)	0.0378 (13)	−0.0215 (15)
Br1	0.0569 (2)	0.0616 (2)	0.04745 (18)	−0.01064 (15)	0.00907 (13)	−0.00452 (13)
N1	0.0404 (12)	0.0540 (14)	0.0343 (11)	0.0006 (11)	0.0072 (9)	−0.0001 (10)
C3	0.0458 (15)	0.0398 (15)	0.0392 (13)	−0.0037 (12)	0.0062 (11)	−0.0010 (11)
C8	0.0422 (14)	0.0460 (15)	0.0382 (13)	−0.0023 (13)	0.0033 (11)	0.0020 (12)
C9	0.0460 (15)	0.0574 (18)	0.0433 (14)	−0.0027 (14)	0.0095 (12)	−0.0081 (13)
C2	0.0492 (15)	0.0486 (17)	0.0333 (13)	−0.0015 (13)	0.0051 (11)	−0.0072 (11)
N2	0.0452 (13)	0.0673 (17)	0.0501 (13)	−0.0047 (12)	0.0154 (11)	0.0002 (12)
C6	0.0471 (16)	0.0572 (19)	0.0530 (16)	−0.0094 (14)	0.0122 (13)	−0.0097 (14)
C1	0.0442 (15)	0.0521 (16)	0.0391 (13)	−0.0054 (13)	0.0019 (12)	−0.0086 (12)
C7	0.0375 (14)	0.079 (2)	0.0438 (14)	0.0029 (14)	0.0072 (12)	0.0041 (14)
C5	0.0563 (17)	0.065 (2)	0.0402 (14)	−0.0061 (15)	0.0109 (13)	−0.0194 (13)
C4	0.0535 (17)	0.0605 (19)	0.0521 (16)	−0.0152 (15)	0.0081 (13)	−0.0190 (14)
C12	0.088 (2)	0.058 (2)	0.078 (2)	0.004 (2)	−0.021 (2)	0.0146 (18)
C10	0.073 (2)	0.076 (2)	0.0409 (16)	−0.0219 (19)	0.0113 (15)	−0.0070 (16)
C13	0.0612 (19)	0.0615 (19)	0.0575 (18)	0.0103 (16)	0.0039 (15)	−0.0007 (15)
C11	0.106 (3)	0.070 (2)	0.0427 (17)	−0.031 (2)	−0.0059 (19)	0.0103 (16)

Geometric parameters (Å, º) top

O1—N2	1.379 (3)	N2—C6	1.272 (3)
O1—H1O	0.81 (4)	C6—H6	0.9300
N1—C5	1.326 (3)	C1—H1	0.9300
N1—C1	1.346 (3)	C7—H7A	0.9700
N1—C7	1.491 (3)	C7—H7B	0.9700
C3—C2	1.382 (4)	C5—C4	1.365 (4)
C3—C4	1.395 (3)	C5—H5	0.9300
C3—C6	1.454 (3)	C4—H4	0.9300
C8—C13	1.370 (4)	C12—C11	1.376 (5)
C8—C9	1.384 (3)	C12—C13	1.390 (4)
C8—C7	1.506 (4)	C12—H12	0.9300
C9—C10	1.371 (4)	C10—C11	1.355 (5)
C9—H9	0.9300	C10—H10	0.9300
C2—C1	1.361 (3)	C13—H13	0.9300
C2—H2	0.9300	C11—H11	0.9300

N2—O1—H1O	107 (3)	N1—C7—H7A	108.9
C5—N1—C1	120.6 (2)	C8—C7—H7A	108.9
C5—N1—C7	119.7 (2)	N1—C7—H7B	108.9
C1—N1—C7	119.5 (2)	C8—C7—H7B	108.9
C2—C3—C4	117.4 (2)	H7A—C7—H7B	107.7
C2—C3—C6	122.8 (2)	N1—C5—C4	121.1 (2)
C4—C3—C6	119.8 (2)	N1—C5—H5	119.5
C13—C8—C9	119.1 (2)	C4—C5—H5	119.5
C13—C8—C7	123.8 (2)	C5—C4—C3	119.9 (3)
C9—C8—C7	116.9 (2)	C5—C4—H4	120.1
C10—C9—C8	120.7 (3)	C3—C4—H4	120.1
C10—C9—H9	119.7	C11—C12—C13	119.9 (3)
C8—C9—H9	119.7	C11—C12—H12	120.0
C1—C2—C3	120.6 (2)	C13—C12—H12	120.0
C1—C2—H2	119.7	C11—C10—C9	120.2 (3)
C3—C2—H2	119.7	C11—C10—H10	119.9
C6—N2—O1	110.2 (2)	C9—C10—H10	119.9
N2—C6—C3	120.0 (3)	C8—C13—C12	119.9 (3)
N2—C6—H6	120.0	C8—C13—H13	120.1
C3—C6—H6	120.0	C12—C13—H13	120.1
N1—C1—C2	120.5 (2)	C10—C11—C12	120.2 (3)
N1—C1—H1	119.8	C10—C11—H11	119.9
C2—C1—H1	119.8	C12—C11—H11	119.9
N1—C7—C8	113.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···Br1	0.80 (4)	2.37 (4)	3.153 (3)	166 (4)

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N-Benzyl-4-(hydroxy­imino­meth­yl)pyridinium bromide

Supporting information

Key indicators

checkCIF/PLATON results

N-Benzyl-4-(hydroxyiminomethyl)pyridinium bromide