The crystal structure of the title compound, C
7H
5F
5NO
+·Cl
−, consists of two-dimensional networks of hydrogen-bonded primary NH
3+ 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 NH
3+ 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].
Supporting information
CCDC reference: 270519
Key indicators
- Single-crystal X-ray study
- T = 130 K
- Mean (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
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
top
Crystal data top
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) Å3 | 0.42 × 0.12 × 0.03 mm |
Z = 4 | |
Data collection top
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 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)] = 0.039 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.090 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.90 | w = 1/[σ2(Fo2) + (0.0436P)2] where P = (Fo2 + 2Fc2)/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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Cl1i | 0.98 (4) | 2.15 (4) | 3.107 (3) | 165 (3) |
N1—H1B···Cl1ii | 1.01 (3) | 2.11 (3) | 3.099 (3) | 166 (2) |
N1—H1C···Cl1iii | 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. |