O-(2,3,4,5,6-Penta­fluoro­benzyl)­hydroxy­laminium chloride

The crystal structure of the title compound, C₇H₅F₅NO⁺·Cl⁻, consists of two-dimensional networks of hydrogen-bonded primary NH₃⁺ cations and chloride anions with the penta­fluoro­benzyl moieties located on one side of the layer. To maximize the Coulombic interactions, the Cl⁻ anions approach the NH₃⁺ groups of the neighbouring network along the O—N bond direction [O—N...Cl = 174.3 (2)°]. The N...Cl distance between the ions belonging to two adjacent networks is 3.066 (2) Å and is shorter than the N...Cl distances in the N⁺—H...Cl⁻ hydrogen bonds [3.099 (3)–3.133 (3) Å].

Key indicators

• Single-crystal X-ray study
• T = 130 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.039
• wR factor = 0.090
• Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.55 Ratio

Author Response: In this structure there are two groups with hydrogen atoms: CH~2~ and terminal NH~3~. The CH2 group shows displacement parameters in the range 0.011-0.026 whereas higher displacement parameters (0.047 - 0.061) are observed for the ammonium group which may show some torsional disorder.

Alert level C
PLAT353_ALERT_3_C Long    N-H Bond (0.87A)   N1     -   H1B    ...       1.01 Ang.
PLAT353_ALERT_3_C Long    N-H Bond (0.87A)   N1     -   H1C    ...       1.02 Ang.

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL97.

O-(2,3,4,5,6-Pentafluorobenzyl)hydroxylaminium chloride

Crystal data

C7H5F5NO^+·Cl^−	F(000) = 496
Mr = 249.57	Dx = 1.725 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2766 reflections
a = 19.994 (3) Å	θ = 4–25°
b = 5.4020 (8) Å	µ = 0.45 mm^−1
c = 9.0305 (15) Å	T = 130 K
β = 99.939 (13)°	Needle, colourless
V = 960.7 (3) Å^3	0.42 × 0.12 × 0.03 mm
Z = 4

Data collection

Kuma KM4CCD κ-geometry diffractometer	1042 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
Graphite monochromator	θmax = 25.0°, θmin = 4.1°
ω scans	h = −23→23
3889 measured reflections	k = −6→6
1702 independent reflections	l = −10→7

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)] = 0.039	Hydrogen site location: difference Fourier map
wR(F^2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	w = 1/[σ^2(Fo^2) + (0.0436P)^2] where P = (Fo^2 + 2Fc^2)/3
1702 reflections	(Δ/σ)max < 0.001
148 parameters	Δρmax = 0.52 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.43596 (3)	0.49780 (16)	0.64572 (7)	0.0221 (2)
N1	0.59161 (11)	0.5006 (7)	0.7027 (3)	0.0199 (5)
O1	0.66373 (8)	0.5146 (4)	0.71519 (19)	0.0232 (5)
F2	0.78437 (9)	0.8558 (4)	1.01187 (19)	0.0328 (5)
F3	0.91761 (9)	0.8765 (4)	0.9974 (2)	0.0383 (5)
F4	0.97437 (8)	0.5267 (4)	0.84078 (18)	0.0393 (5)
F5	0.89702 (9)	0.1485 (4)	0.70502 (19)	0.0374 (5)
F6	0.76461 (9)	0.1228 (3)	0.72276 (19)	0.0300 (5)
C1	0.77027 (12)	0.4886 (7)	0.8679 (3)	0.0162 (6)
C2	0.81110 (15)	0.6768 (6)	0.9345 (3)	0.0217 (7)
C3	0.87928 (15)	0.6903 (6)	0.9280 (3)	0.0239 (8)
C4	0.90836 (13)	0.5140 (7)	0.8506 (3)	0.0238 (7)
C5	0.86958 (16)	0.3222 (6)	0.7817 (3)	0.0251 (8)
C6	0.80141 (15)	0.3122 (6)	0.7918 (3)	0.0209 (7)
C7	0.69560 (13)	0.4771 (7)	0.8702 (3)	0.0219 (7)
H7B	0.6832	0.3175	0.9065	0.026 (9)*
H7A	0.6823	0.6058	0.9341	0.011 (7)*
H1A	0.5747 (17)	0.647 (7)	0.748 (4)	0.047 (11)*
H1B	0.5743 (15)	0.502 (7)	0.591 (4)	0.051 (10)*
H1C	0.5814 (19)	0.335 (8)	0.749 (4)	0.061 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0215 (4)	0.0218 (4)	0.0225 (4)	0.0015 (4)	0.0024 (3)	−0.0001 (4)
N1	0.0123 (12)	0.0231 (15)	0.0238 (13)	0.0024 (16)	0.0021 (10)	−0.0028 (17)
O1	0.0124 (9)	0.0379 (13)	0.0187 (10)	0.0016 (12)	0.0010 (7)	0.0015 (12)
F2	0.0361 (11)	0.0318 (11)	0.0306 (11)	0.0028 (9)	0.0064 (8)	−0.0122 (9)
F3	0.0323 (11)	0.0440 (13)	0.0369 (11)	−0.0164 (10)	0.0010 (9)	−0.0072 (10)
F4	0.0173 (9)	0.0672 (15)	0.0341 (10)	−0.0007 (11)	0.0065 (7)	0.0049 (12)
F5	0.0321 (11)	0.0490 (13)	0.0327 (11)	0.0135 (10)	0.0104 (9)	−0.0106 (10)
F6	0.0302 (11)	0.0287 (11)	0.0304 (10)	−0.0013 (9)	0.0028 (8)	−0.0078 (9)
C1	0.0155 (13)	0.0205 (16)	0.0131 (13)	0.0014 (17)	0.0037 (11)	0.0042 (17)
C2	0.0275 (18)	0.0203 (19)	0.0177 (16)	0.0042 (15)	0.0050 (13)	0.0006 (14)
C3	0.0243 (18)	0.027 (2)	0.0185 (17)	−0.0085 (16)	−0.0030 (14)	0.0016 (15)
C4	0.0143 (14)	0.038 (2)	0.0188 (14)	−0.0030 (19)	0.0026 (11)	0.0084 (19)
C5	0.0262 (18)	0.031 (2)	0.0191 (17)	0.0117 (16)	0.0070 (14)	0.0025 (15)
C6	0.0222 (17)	0.0217 (19)	0.0167 (16)	−0.0041 (15)	−0.0024 (13)	0.0011 (14)
C7	0.0185 (14)	0.033 (2)	0.0135 (13)	0.0021 (18)	−0.0001 (11)	0.0007 (17)

Geometric parameters (Å, º)

N1—O1	1.429 (3)	C1—C2	1.376 (4)
N1—H1A	0.98 (4)	C1—C6	1.384 (4)
N1—H1B	1.01 (3)	C1—C7	1.498 (3)
N1—H1C	1.02 (4)	C2—C3	1.376 (4)
O1—C7	1.448 (3)	C3—C4	1.369 (4)
F2—C2	1.355 (3)	C4—C5	1.377 (4)
F3—C3	1.351 (3)	C5—C6	1.383 (4)
F4—C4	1.340 (3)	C7—H7B	0.9700
F5—C5	1.338 (3)	C7—H7A	0.9700
F6—C6	1.349 (3)
O1—N1—H1A	110 (2)	F4—C4—C3	120.5 (3)
O1—N1—H1B	104.3 (17)	F4—C4—C5	119.6 (3)
H1A—N1—H1B	109 (3)	C3—C4—C5	119.9 (3)
O1—N1—H1C	107 (2)	F5—C5—C4	120.8 (3)
H1A—N1—H1C	116 (2)	F5—C5—C6	120.2 (3)
H1B—N1—H1C	111 (3)	C4—C5—C6	119.0 (3)
N1—O1—C7	109.79 (18)	F6—C6—C5	117.7 (3)
C2—C1—C6	116.2 (2)	F6—C6—C1	119.7 (3)
C2—C1—C7	122.8 (3)	C5—C6—C1	122.6 (3)
C6—C1—C7	120.9 (3)	O1—C7—C1	104.7 (2)
F2—C2—C1	119.7 (3)	O1—C7—H7B	110.8
F2—C2—C3	117.8 (3)	C1—C7—H7B	110.8
C1—C2—C3	122.5 (3)	O1—C7—H7A	110.8
F3—C3—C4	119.8 (3)	C1—C7—H7A	110.8
F3—C3—C2	120.4 (3)	H7B—C7—H7A	108.9
C4—C3—C2	119.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1^i	0.98 (4)	2.15 (4)	3.107 (3)	165 (3)
N1—H1B···Cl1^ii	1.01 (3)	2.11 (3)	3.099 (3)	166 (2)
N1—H1C···Cl1^iii	1.02 (4)	2.11 (4)	3.133 (3)	177 (3)

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