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The crystal structure of the title compound, C
8H
10NO
+·Cl
−·H
2O, is composed of 4-acetylanilinium cations, chloride anions and water molecules of crystallization. The crystal packing features stacking interactions between the aromatic rings, with stacks running along the
c axis of the crystal, as well as extensive N—H
O, N—H
Cl and O—H
Cl hydrogen bonding which involves all five `active' H atoms and links cations, anions and water molecules into a three-dimensional framework.
Supporting information
CCDC reference: 236088
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.032
- wR factor = 0.070
- Data-to-parameter ratio = 18.0
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSMU01_ALERT_1_C The ratio of given/expected absorption coefficient lies
outside the range 0.99 <> 1.01
Calculated value of mu = 0.354
Value of mu given = 0.350
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 28.90
From the CIF: _reflns_number_total 2447
Count of symmetry unique reflns 1286
Completeness (_total/calc) 190.28%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1161
Fraction of Friedel pairs measured 0.903
Are heavy atom types Z>Si present yes
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
2 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
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
4-Acetylanilinium chloride monohydrate
top
Crystal data top
C8H10NO+·Cl−·H2O | F(000) = 400 |
Mr = 189.64 | Dx = 1.294 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 9241 reflections |
a = 7.690 (1) Å | θ = 2.3–28.9° |
b = 17.930 (1) Å | µ = 0.35 mm−1 |
c = 7.095 (1) Å | T = 293 K |
β = 95.70 (1)° | Prism, light yellow |
V = 973.4 (2) Å3 | 0.30 × 0.21 × 0.21 mm |
Z = 4 | |
Data collection top
Stoe IPDS-II diffractometer | 2447 independent reflections |
Radiation source: fine-focus sealed tube | 2060 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.051 |
Detector resolution: 6.67 pixels mm-1 | θmax = 28.9°, θmin = 2.3° |
ω scans | h = −10→10 |
Absorption correction: numerical (X-RED32; Stoe & Cie, 2002) | k = −24→24 |
Tmin = 0.915, Tmax = 0.928 | l = −9→9 |
7188 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.070 | w = 1/[σ2(Fo2) + (0.0444P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max = 0.001 |
2447 reflections | Δρmax = 0.26 e Å−3 |
136 parameters | Δρmin = −0.28 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 1162 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.3 (2) |
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 | |
C1 | 0.37038 (17) | 0.56770 (8) | 0.55422 (19) | 0.0358 (3) | |
C2 | 0.35176 (19) | 0.49125 (8) | 0.5448 (2) | 0.0387 (3) | |
C3 | 0.4955 (2) | 0.44711 (8) | 0.5970 (2) | 0.0394 (3) | |
C4 | 0.65569 (19) | 0.47889 (10) | 0.6609 (2) | 0.0365 (3) | |
C5 | 0.67059 (19) | 0.55637 (9) | 0.6700 (2) | 0.0391 (3) | |
C6 | 0.5283 (2) | 0.60097 (8) | 0.6164 (2) | 0.0398 (3) | |
C7 | 0.8124 (2) | 0.43265 (9) | 0.7231 (3) | 0.0434 (3) | |
C8 | 0.8012 (4) | 0.34981 (10) | 0.6994 (4) | 0.0623 (4) | |
H8A | 0.7778 | 0.3379 | 0.5674 | 0.093* | |
H8B | 0.7087 | 0.3308 | 0.7672 | 0.093* | |
H8C | 0.9100 | 0.3276 | 0.7484 | 0.093* | |
Cl1 | 0.29535 (7) | 0.73358 (2) | 0.20594 (8) | 0.05657 (12) | |
N1 | 0.21959 (17) | 0.61501 (8) | 0.5028 (2) | 0.0447 (3) | |
H1A | 0.1346 | 0.5880 | 0.4419 | 0.067* | |
H1B | 0.2496 | 0.6517 | 0.4279 | 0.067* | |
H1C | 0.1823 | 0.6343 | 0.6071 | 0.067* | |
O1 | 0.94433 (17) | 0.46252 (9) | 0.7939 (2) | 0.0640 (4) | |
O1W | 0.1104 (2) | 0.66512 (10) | 0.8296 (3) | 0.0742 (5) | |
H2 | 0.244 (3) | 0.4719 (10) | 0.506 (3) | 0.041 (4)* | |
H1W | 0.178 (5) | 0.6825 (19) | 0.922 (5) | 0.101 (10)* | |
H3 | 0.479 (3) | 0.3944 (11) | 0.591 (3) | 0.055 (5)* | |
H2W | 0.022 (4) | 0.6955 (18) | 0.803 (4) | 0.089 (8)* | |
H5 | 0.774 (3) | 0.5786 (10) | 0.714 (3) | 0.043 (4)* | |
H6 | 0.536 (3) | 0.6553 (12) | 0.618 (3) | 0.053 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0354 (7) | 0.0417 (7) | 0.0295 (6) | −0.0018 (6) | −0.0005 (5) | 0.0012 (6) |
C2 | 0.0348 (6) | 0.0416 (7) | 0.0384 (7) | −0.0097 (6) | −0.0022 (6) | −0.0014 (6) |
C3 | 0.0411 (7) | 0.0358 (6) | 0.0408 (7) | −0.0071 (6) | 0.0017 (6) | −0.0007 (6) |
C4 | 0.0342 (7) | 0.0438 (8) | 0.0311 (6) | −0.0013 (6) | 0.0014 (5) | 0.0000 (6) |
C5 | 0.0345 (7) | 0.0453 (8) | 0.0365 (7) | −0.0092 (6) | −0.0018 (6) | −0.0026 (6) |
C6 | 0.0425 (7) | 0.0351 (7) | 0.0404 (7) | −0.0072 (6) | −0.0026 (6) | 0.0001 (6) |
C7 | 0.0375 (8) | 0.0515 (8) | 0.0407 (8) | 0.0039 (7) | 0.0019 (6) | 0.0019 (8) |
C8 | 0.0539 (9) | 0.0514 (8) | 0.0803 (11) | 0.0116 (11) | 0.0003 (8) | −0.0040 (12) |
Cl1 | 0.0564 (2) | 0.04558 (18) | 0.0653 (2) | 0.0039 (2) | −0.00585 (16) | 0.0074 (2) |
N1 | 0.0391 (6) | 0.0457 (7) | 0.0470 (7) | −0.0007 (5) | −0.0076 (5) | 0.0017 (6) |
O1 | 0.0426 (7) | 0.0627 (8) | 0.0819 (10) | 0.0033 (6) | −0.0175 (7) | −0.0005 (7) |
O1W | 0.0741 (10) | 0.0760 (10) | 0.0708 (9) | 0.0249 (9) | −0.0009 (8) | −0.0167 (8) |
Geometric parameters (Å, º) top
C1—C2 | 1.379 (2) | C6—H6 | 0.98 (2) |
C1—C6 | 1.385 (2) | C7—O1 | 1.211 (2) |
C1—N1 | 1.454 (2) | C7—C8 | 1.496 (2) |
C2—C3 | 1.380 (2) | C8—H8A | 0.9600 |
C2—H2 | 0.92 (2) | C8—H8B | 0.9600 |
C3—C4 | 1.392 (2) | C8—H8C | 0.9600 |
C3—H3 | 0.95 (2) | N1—H1A | 0.8900 |
C4—C5 | 1.395 (2) | N1—H1B | 0.8900 |
C4—C7 | 1.493 (2) | N1—H1C | 0.8900 |
C5—C6 | 1.378 (2) | O1W—H1W | 0.85 (4) |
C5—H5 | 0.92 (2) | O1W—H2W | 0.88 (3) |
| | | |
C2—C1—C6 | 121.8 (1) | C1—C6—H6 | 118.9 (13) |
C2—C1—N1 | 119.4 (1) | O1—C7—C4 | 119.7 (1) |
C6—C1—N1 | 118.74 (13) | O1—C7—C8 | 121.5 (2) |
C1—C2—C3 | 118.71 (13) | C4—C7—C8 | 118.8 (2) |
C1—C2—H2 | 118.5 (11) | C7—C8—H8A | 109.5 |
C3—C2—H2 | 122.8 (11) | C7—C8—H8B | 109.5 |
C2—C3—C4 | 120.8 (1) | H8A—C8—H8B | 109.5 |
C2—C3—H3 | 117.2 (14) | C7—C8—H8C | 109.5 |
C4—C3—H3 | 122.0 (14) | H8A—C8—H8C | 109.5 |
C3—C4—C5 | 119.26 (14) | H8B—C8—H8C | 109.5 |
C3—C4—C7 | 122.09 (15) | C1—N1—H1A | 109.5 |
C5—C4—C7 | 118.64 (13) | C1—N1—H1B | 109.5 |
C6—C5—C4 | 120.40 (13) | H1A—N1—H1B | 109.5 |
C6—C5—H5 | 118.7 (12) | C1—N1—H1C | 109.5 |
C4—C5—H5 | 120.9 (12) | H1A—N1—H1C | 109.5 |
C5—C6—C1 | 119.01 (13) | H1B—N1—H1C | 109.5 |
C5—C6—H6 | 122.0 (14) | H1W—O1W—H2W | 110 (3) |
| | | |
C6—C1—C2—C3 | −0.8 (2) | C4—C5—C6—C1 | 0.2 (2) |
N1—C1—C2—C3 | −178.97 (14) | C2—C1—C6—C5 | 0.1 (2) |
C1—C2—C3—C4 | 1.0 (2) | N1—C1—C6—C5 | 178.37 (13) |
C2—C3—C4—C5 | −0.7 (2) | C3—C4—C7—O1 | −173.21 (17) |
C2—C3—C4—C7 | 178.40 (16) | C5—C4—C7—O1 | 5.9 (3) |
C3—C4—C5—C6 | 0.1 (2) | C3—C4—C7—C8 | 5.7 (3) |
C7—C4—C5—C6 | −179.06 (16) | C5—C4—C7—C8 | −175.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.89 | 1.94 | 2.826 (2) | 175 |
O1W—H1W···Cl1ii | 0.85 (4) | 2.32 (4) | 3.147 (2) | 165 (3) |
O1W—H2W···Cl1iii | 0.88 (3) | 2.21 (3) | 3.084 (2) | 174 (3) |
N1—H1B···Cl1 | 0.89 | 2.21 | 3.089 (2) | 171 |
N1—H1C···O1W | 0.89 | 1.81 | 2.697 (2) | 175 |
Symmetry codes: (i) x−1, −y+1, z−1/2; (ii) x, y, z+1; (iii) x−1/2, −y+3/2, z+1/2. |
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