4-Acetyl­anilinium chloride monohydrate

The crystal structure of the title compound, C₈H₁₀NO⁺·Cl⁻·H₂O, 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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	0.30 × 0.21 × 0.21 mm
Z = 4

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.070	w = 1/[σ^2(Fo^2) + (0.0444P)^2] where P = (Fo^2 + 2Fc^2)/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

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
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^i	0.89	1.94	2.826 (2)	175
O1W—H1W···Cl1^ii	0.85 (4)	2.32 (4)	3.147 (2)	165 (3)
O1W—H2W···Cl1^iii	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.