4-(Hydroxy­amino­carbon­yl)pyridinium chloride

The crystal structure of the title salt, C₆H₇N₂O₂⁺·Cl⁻, consists of N-hydroxy­isonicotinamidium cations and Cl⁻ anions linked through N—H...Cl, O—H...Cl and N—H...O hydrogen bonds into layers arranged parallel to the (010) plane.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.030
• wR factor = 0.079
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  O1     ..  C4      ..       2.90 Ang.

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

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

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Computing details

Data collection: COLLECT (Bruker, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

4-(Hydroxyaminocarbonyl)pyridinium chloride

Crystal data

C6H7N2O2^+·Cl^−	F(000) = 720
Mr = 174.59	Dx = 1.557 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6083 reflections
a = 7.0421 (2) Å	θ = 1.0–27.5°
b = 14.3771 (3) Å	µ = 0.46 mm^−1
c = 14.7134 (4) Å	T = 120 K
V = 1489.66 (7) Å^3	Block, colourless
Z = 8	0.28 × 0.16 × 0.08 mm

Data collection

Nonius KappaCCD area-detector diffractometer	1713 independent reflections
Radiation source: fine-focus sealed tube	1441 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	Rint = 0.047
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 2.8°
φ scans, and ω scans with κ offset	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −18→18
Tmin = 0.881, Tmax = 0.962	l = −18→19
24587 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: difference Fourier map
wR(F^2) = 0.080	All H-atom parameters refined
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0347P)^2 + 0.8006P] where P = (Fo^2 + 2Fc^2)/3
1713 reflections	(Δ/σ)max = 0.001
128 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.40487 (5)	0.26771 (2)	0.91981 (2)	0.02139 (13)
O1	0.70115 (17)	0.05181 (7)	0.66663 (7)	0.0232 (3)
O2	0.54033 (17)	0.22468 (8)	0.67394 (7)	0.0237 (3)
N1	0.72875 (18)	−0.06610 (9)	0.98268 (8)	0.0179 (3)
N2	0.58811 (19)	0.17246 (8)	0.75041 (9)	0.0190 (3)
C1	0.6583 (2)	0.08725 (10)	0.74018 (10)	0.0164 (3)
C2	0.6843 (2)	0.03478 (10)	0.82768 (9)	0.0154 (3)
C3	0.7343 (2)	0.07867 (10)	0.90854 (10)	0.0172 (3)
C4	0.7566 (2)	0.02625 (10)	0.98621 (10)	0.0177 (3)
C5	0.6824 (2)	−0.11095 (10)	0.90599 (10)	0.0202 (3)
C6	0.6605 (2)	−0.06168 (10)	0.82644 (10)	0.0192 (3)
H3	0.757 (3)	0.1439 (14)	0.9109 (11)	0.029 (5)*
H4	0.791 (2)	0.0543 (12)	1.0454 (12)	0.023 (4)*
H5	0.664 (3)	−0.1761 (15)	0.9118 (12)	0.032 (5)*
H6	0.629 (3)	−0.0915 (13)	0.7737 (12)	0.024 (4)*
H1N	0.739 (3)	−0.0994 (15)	1.0339 (14)	0.041 (6)*
H2N	0.545 (3)	0.1961 (14)	0.8043 (13)	0.030 (5)*
H2O	0.654 (3)	0.2384 (14)	0.6487 (14)	0.036 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0228 (2)	0.0204 (2)	0.0210 (2)	0.00073 (14)	0.00090 (15)	−0.00580 (14)
O1	0.0329 (6)	0.0232 (5)	0.0134 (5)	0.0012 (5)	0.0028 (5)	−0.0020 (4)
O2	0.0228 (6)	0.0283 (6)	0.0200 (6)	0.0038 (5)	−0.0003 (5)	0.0119 (5)
N1	0.0202 (7)	0.0182 (6)	0.0151 (6)	0.0023 (5)	−0.0009 (5)	0.0032 (5)
N2	0.0235 (7)	0.0198 (6)	0.0136 (6)	0.0037 (5)	0.0004 (5)	0.0040 (5)
C1	0.0152 (7)	0.0193 (7)	0.0148 (7)	−0.0020 (6)	0.0001 (6)	0.0003 (6)
C2	0.0135 (7)	0.0184 (7)	0.0142 (7)	0.0015 (5)	0.0010 (6)	0.0005 (5)
C3	0.0193 (7)	0.0147 (7)	0.0176 (7)	−0.0011 (6)	−0.0008 (6)	−0.0007 (5)
C4	0.0195 (7)	0.0172 (7)	0.0163 (7)	0.0006 (6)	−0.0015 (6)	−0.0016 (6)
C5	0.0241 (8)	0.0142 (7)	0.0224 (8)	−0.0002 (6)	−0.0018 (6)	−0.0004 (6)
C6	0.0220 (8)	0.0191 (7)	0.0166 (7)	0.0005 (6)	−0.0022 (6)	−0.0044 (6)

Geometric parameters (Å, º)

O1—C1	1.2336 (17)	C2—C3	1.392 (2)
O2—N2	1.3938 (16)	C2—C6	1.397 (2)
O2—H2O	0.90 (2)	C3—C4	1.378 (2)
N1—C5	1.3400 (19)	C3—H3	0.95 (2)
N1—C4	1.3431 (19)	C4—H4	0.990 (18)
N1—H1N	0.90 (2)	C5—C6	1.377 (2)
N2—C1	1.3296 (19)	C5—H5	0.95 (2)
N2—H2N	0.916 (19)	C6—H6	0.914 (18)
C1—C2	1.5033 (19)
N2—O2—H2O	103.7 (13)	C4—C3—C2	119.33 (13)
C5—N1—C4	122.94 (13)	C4—C3—H3	119.3 (10)
C5—N1—H1N	118.0 (13)	C2—C3—H3	121.4 (10)
C4—N1—H1N	119.0 (13)	N1—C4—C3	119.47 (13)
C1—N2—O2	119.65 (12)	N1—C4—H4	118.2 (10)
C1—N2—H2N	124.4 (12)	C3—C4—H4	122.3 (10)
O2—N2—H2N	114.7 (12)	N1—C5—C6	119.71 (13)
O1—C1—N2	124.80 (13)	N1—C5—H5	115.6 (11)
O1—C1—C2	120.95 (13)	C6—C5—H5	124.7 (11)
N2—C1—C2	114.24 (12)	C5—C6—C2	119.09 (14)
C3—C2—C6	119.44 (13)	C5—C6—H6	120.6 (11)
C3—C2—C1	122.36 (13)	C2—C6—H6	120.3 (11)
C6—C2—C1	118.19 (13)
O2—N2—C1—O1	6.5 (2)	C1—C2—C3—C4	−179.69 (13)
O2—N2—C1—C2	−173.80 (12)	C5—N1—C4—C3	1.1 (2)
O1—C1—C2—C3	145.92 (15)	C2—C3—C4—N1	−0.4 (2)
N2—C1—C2—C3	−33.8 (2)	C4—N1—C5—C6	−0.4 (2)
O1—C1—C2—C6	−32.8 (2)	N1—C5—C6—C2	−1.0 (2)
N2—C1—C2—C6	147.46 (14)	C3—C2—C6—C5	1.6 (2)
C6—C2—C3—C4	−1.0 (2)	C1—C2—C6—C5	−179.59 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.90 (2)	2.11 (2)	2.7588 (16)	128.3 (18)
N1—H1N···Cl1^ii	0.90 (2)	2.71 (2)	3.3683 (13)	131.3 (17)
N2—H2N···Cl1	0.916 (19)	2.22 (2)	3.1230 (14)	170.0 (17)
O2—H2O···Cl1^iii	0.90 (2)	2.08 (2)	2.9792 (13)	175.3 (19)

Symmetry codes: (i) −x+3/2, −y, z+1/2; (ii) −x+1, −y, −z+2; (iii) x+1/2, y, −z+3/2.