N-(3-Hydroxy­phen­yl)acetamide

In the crystal structure of the title compound, C₈H₉NO₂, the topology of the hydrogen-bond network can be characterized by the graph-set C(6). The geometry of the hydrogen bonds in this compound is compared with the analogous parameters of similar compounds viz. acetanilide, paracetamol (forms I and II) and phenacetin.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.032
• wR factor = 0.093
• Data-to-parameter ratio = 9.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.17

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           26.96
           From the CIF: _reflns_number_total                946
           Count of symmetry unique reflns          945
           Completeness (_total/calc)            100.11%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         1
           Fraction of Friedel pairs measured     0.001
           Are heavy atom types Z>Si present         no

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

   3 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4-PC (Enraf–Nonius, 1992); cell refinement: CELDIM in CAD-4-PC Software; data reduction: XCAD4 (McArdle & Higgins, 1995); program(s) used to solve structure: OSCAIL (McArdle, 2005) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1993) and ORTEPIII (Burnett & Johnson, (1996); software used to prepare material for publication: OSCAIL.

N-(2-hydroxyphenyl)acetamide

Crystal data

C8H9NO2	F(000) = 320
Mr = 151.16	Dx = 1.322 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 25 reflections
a = 10.5199 (11) Å	θ = 14–21°
b = 17.0195 (13) Å	µ = 0.10 mm^−1
c = 4.2415 (8) Å	T = 293 K
V = 759.41 (17) Å^3	Block, colourless
Z = 4	0.40 × 0.20 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	741 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 27.0°, θmin = 2.3°
ω–2θ scans	h = 0→13
Absorption correction: ψ scan [ABSCALC in OSCAIL (McArdle & Daly, 1999; North et al., 1968)]	k = 0→21
Tmin = 0.963, Tmax = 0.986	l = 0→5
946 measured reflections	3 standard reflections every 120 min
946 independent reflections	intensity decay: 1%

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.055P)^2 + 0.0863P] where P = (Fo^2 + 2Fc^2)/3
946 reflections	(Δ/σ)max < 0.001
102 parameters	Δρmax = 0.18 e Å^−3
1 restraint	Δρmin = −0.14 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

5.4001 (0.0072) x + 4.1757 (0.0071) y + 3.4881 (0.0017) z = 6.1178 (0.0037)

* -0.0322 (0.0018) O1 * -0.0205 (0.0023) C1 * 0.0146 (0.0022) C2 * 0.0439 (0.0023) C3 * 0.0408 (0.0025) C4 * -0.0016 (0.0024) C5 * -0.0206 (0.0023) C6 * 0.0693 (0.0022) N1 * -0.0128 (0.0021) C7 * -0.0506 (0.0022) O2 * -0.0302 (0.0021) C8

Rms deviation of fitted atoms = 0.0358

5.3502 (0.0085) x + 3.8132 (0.0100) y + 3.5262 (0.0021) z = 5.9496 (0.0049)

Angle to previous plane (with approximate e.s.d.) = 1.35 (0.11)

* -0.0060 (0.0023) C1 * -0.0018 (0.0021) C2 * 0.0029 (0.0021) C3 * 0.0064 (0.0024) C4 * -0.0047 (0.0022) C5 * 0.0008 (0.0022) C6 * -0.0025 (0.0016) N1 * 0.0049 (0.0016) O1 - 0.1127 (0.0033) C7 - 0.1534 (0.0037) O2 - 0.1581 (0.0044) C8

Rms deviation of fitted atoms = 0.0042

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
O1	0.35956 (14)	0.38815 (8)	0.7234 (6)	0.0591 (6)
H1	0.3128	0.3546	0.8000	0.089*
O2	0.24922 (14)	0.75979 (8)	0.4440 (7)	0.0596 (6)
N1	0.37712 (15)	0.65301 (9)	0.4082 (6)	0.0396 (4)
H1A	0.4496	0.6379	0.3367	0.048*
C1	0.30029 (19)	0.45961 (11)	0.7329 (7)	0.0401 (5)
C2	0.35974 (18)	0.52038 (10)	0.5782 (6)	0.0378 (5)
H2	0.4358	0.5111	0.4727	0.045*
C3	0.30773 (18)	0.59539 (11)	0.5773 (6)	0.0350 (5)
C4	0.1944 (2)	0.60924 (12)	0.7353 (7)	0.0441 (5)
H4	0.1586	0.6592	0.7383	0.053*
C5	0.1355 (2)	0.54723 (13)	0.8886 (8)	0.0485 (6)
H5	0.0589	0.5561	0.9919	0.058*
C6	0.1869 (2)	0.47285 (12)	0.8926 (7)	0.0446 (6)
H6	0.1466	0.4323	1.0000	0.054*
C7	0.3458 (2)	0.72795 (11)	0.3434 (6)	0.0405 (6)
C8	0.4396 (3)	0.77117 (13)	0.1415 (7)	0.0528 (7)
H8A	0.3948	0.8039	−0.0057	0.079*
H8B	0.4910	0.7341	0.0285	0.079*
H8C	0.4930	0.8032	0.2725	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0412 (8)	0.0277 (6)	0.1083 (16)	0.0002 (6)	0.0057 (10)	0.0160 (10)
O2	0.0516 (9)	0.0303 (7)	0.0969 (16)	0.0102 (7)	0.0058 (11)	0.0158 (11)
N1	0.0375 (8)	0.0270 (7)	0.0544 (11)	0.0030 (6)	0.0016 (10)	0.0044 (9)
C1	0.0336 (9)	0.0270 (8)	0.0598 (15)	−0.0015 (8)	−0.0080 (11)	0.0041 (11)
C2	0.0314 (9)	0.0295 (9)	0.0526 (13)	0.0005 (7)	−0.0016 (12)	0.0022 (10)
C3	0.0339 (9)	0.0267 (8)	0.0444 (11)	−0.0003 (7)	−0.0054 (11)	0.0031 (9)
C4	0.0430 (11)	0.0306 (9)	0.0587 (14)	0.0053 (8)	0.0019 (12)	−0.0011 (12)
C5	0.0431 (11)	0.0447 (11)	0.0579 (16)	0.0008 (9)	0.0107 (13)	−0.0012 (13)
C6	0.0404 (11)	0.0385 (11)	0.0550 (15)	−0.0074 (8)	−0.0004 (13)	0.0061 (12)
C7	0.0402 (10)	0.0275 (8)	0.0536 (16)	0.0012 (8)	−0.0072 (11)	0.0048 (10)
C8	0.0557 (13)	0.0346 (10)	0.0679 (19)	−0.0026 (9)	−0.0008 (14)	0.0122 (11)

Geometric parameters (Å, º)

O1—C1	1.367 (2)	C3—C4	1.388 (3)
O1—H1	0.8200	C4—C5	1.386 (3)
O2—C7	1.228 (3)	C4—H4	0.9300
N1—C7	1.346 (2)	C5—C6	1.377 (3)
N1—C3	1.417 (3)	C5—H5	0.9300
N1—H1A	0.8600	C6—H6	0.9300
C1—C2	1.375 (3)	C7—C8	1.499 (3)
C1—C6	1.390 (4)	C8—H8A	0.9600
C2—C3	1.389 (2)	C8—H8B	0.9600
C2—H2	0.9300	C8—H8C	0.9600
C1—O1—H1	109.5	C6—C5—C4	122.0 (2)
C7—N1—C3	129.27 (19)	C6—C5—H5	119.0
C7—N1—H1A	115.4	C4—C5—H5	119.0
C3—N1—H1A	115.4	C5—C6—C1	118.7 (2)
O1—C1—C2	116.6 (2)	C5—C6—H6	120.7
O1—C1—C6	123.4 (2)	C1—C6—H6	120.7
C2—C1—C6	120.05 (18)	O2—C7—N1	123.4 (2)
C1—C2—C3	120.9 (2)	O2—C7—C8	121.76 (19)
C1—C2—H2	119.6	N1—C7—C8	114.9 (2)
C3—C2—H2	119.6	C7—C8—H8A	109.5
C4—C3—C2	119.56 (19)	C7—C8—H8B	109.5
C4—C3—N1	124.70 (17)	H8A—C8—H8B	109.5
C2—C3—N1	115.74 (19)	C7—C8—H8C	109.5
C5—C4—C3	118.76 (19)	H8A—C8—H8C	109.5
C5—C4—H4	120.6	H8B—C8—H8C	109.5
C3—C4—H4	120.6
O1—C1—C2—C3	−179.3 (2)	N1—C3—C4—C5	179.2 (3)
C6—C1—C2—C3	−0.3 (4)	C3—C4—C5—C6	1.0 (5)
C1—C2—C3—C4	0.1 (4)	C4—C5—C6—C1	−1.1 (4)
C1—C2—C3—N1	−179.6 (2)	O1—C1—C6—C5	179.7 (3)
C7—N1—C3—C4	−5.9 (4)	C2—C1—C6—C5	0.8 (4)
C7—N1—C3—C2	173.8 (2)	C3—N1—C7—O2	4.4 (4)
C2—C3—C4—C5	−0.5 (4)	C3—N1—C7—C8	−176.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.82	1.85	2.638 (2)	162
N1—H1A···O1^ii	0.86	2.11	2.963 (2)	171
C4—H4···O2	0.93	2.32	2.902 (3)	120

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