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The crystal structure of commercially available 4-hydroxy­phenyl­acetic acid, C8H8O3, is non-centrosymmetric, with four hydrogen bonds between each mol­ecule and adjacent mol­ecules. The hydrogen bonds link the mol­ecules in the crystal structure into an infinite three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805016405/ya6248sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805016405/ya6248Isup2.hkl
Contains datablock I

CCDC reference: 274674

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.044
  • wR factor = 0.111
  • Data-to-parameter ratio = 8.6

checkCIF/PLATON results

No syntax errors found



Alert level B ABSMU01_ALERT_1_B The ratio of given/expected absorption coefficient lies outside the range 0.95 <> 1.05 Calculated value of mu = 0.105 Value of mu given = 0.100
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 26.00 From the CIF: _reflns_number_total 871 Count of symmetry unique reflns 875 Completeness (_total/calc) 99.54% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: maXus (Mackay et al., 1999).

4-Hydroxyphenylacetic acid top
Crystal data top
C8H8O3F(000) = 320
Mr = 152.15Dx = 1.368 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 74 reflections
a = 5.3100 (3) Åθ = 4.5–21.2°
b = 9.0392 (4) ŵ = 0.10 mm1
c = 15.3871 (8) ÅT = 299 K
V = 738.55 (7) Å3Block, colourless
Z = 40.49 × 0.18 × 0.16 mm
Data collection top
Nonius KappaCCD
diffractometer
Rint = 0.049
Radiation source: fine-focus sealed tubeθmax = 26.0°, θmin = 4.5°
φ and ω scansh = 56
6743 measured reflectionsk = 1011
871 independent reflectionsl = 1818
706 reflections with I > 2σ(I)
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044 w = 1/[σ2(Fo2) + (0.0415P)2 + 0.28P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.111(Δ/σ)max < 0.001
S = 1.08Δρmax = 0.22 e Å3
871 reflectionsΔρmin = 0.15 e Å3
101 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.036 (8)
Primary atom site location: structure-invariant direct methods
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
xyzUiso*/Ueq
C30.6679 (8)0.3560 (4)0.1561 (2)0.0602 (9)
H30.61200.40490.10180.072*
C20.8732 (6)0.2648 (3)0.15162 (17)0.0485 (8)
C60.8141 (7)0.1979 (4)0.29934 (19)0.0557 (9)
H60.88380.13790.34300.067*
C50.6080 (6)0.2880 (3)0.30619 (18)0.0518 (8)
C80.5346 (7)0.4459 (3)0.43709 (18)0.0522 (8)
C10.9466 (6)0.1847 (4)0.22287 (18)0.0547 (8)
H11.09980.11570.21650.066*
C40.5353 (7)0.3669 (4)0.2333 (2)0.0629 (9)
H40.37450.42300.23430.075*
C70.4698 (8)0.3061 (4)0.3902 (2)0.0671 (11)
H7A0.29790.31990.38230.080*
H7B0.42210.22810.42260.080*
O31.0014 (5)0.2594 (2)0.07362 (12)0.0631 (7)
H3A1.09020.16490.06480.076*
O10.3664 (5)0.4870 (3)0.49453 (13)0.0680 (8)
H1A0.41850.57830.51930.082*
O20.7267 (6)0.5102 (4)0.42620 (19)0.0973 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C30.075 (2)0.0557 (19)0.0498 (17)0.013 (2)0.0044 (17)0.0068 (15)
C20.0586 (19)0.0437 (15)0.0430 (14)0.0049 (16)0.0011 (13)0.0011 (12)
C60.065 (2)0.0575 (19)0.0449 (16)0.0048 (18)0.0087 (15)0.0073 (15)
C50.0602 (19)0.0466 (16)0.0484 (16)0.0158 (16)0.0018 (15)0.0074 (14)
C80.061 (2)0.0515 (17)0.0436 (15)0.0108 (17)0.0077 (15)0.0008 (13)
C10.0583 (18)0.0566 (18)0.0490 (16)0.0066 (17)0.0032 (15)0.0059 (14)
C40.063 (2)0.0559 (19)0.069 (2)0.0103 (19)0.0047 (19)0.0020 (16)
C70.079 (2)0.061 (2)0.0616 (19)0.027 (2)0.0211 (19)0.0136 (16)
O30.0820 (17)0.0580 (13)0.0492 (11)0.0191 (13)0.0154 (11)0.0096 (10)
O10.0757 (17)0.0677 (15)0.0605 (13)0.0091 (15)0.0182 (12)0.0136 (12)
O20.096 (2)0.0910 (19)0.105 (2)0.0453 (18)0.0437 (18)0.0510 (18)
Geometric parameters (Å, º) top
C3—C21.368 (5)C8—O21.186 (4)
C3—C41.383 (5)C8—O11.310 (4)
C3—H30.9915C8—C71.496 (4)
C2—C11.371 (4)C1—H11.0299
C2—O31.381 (3)C4—H40.9931
C6—C51.368 (5)C7—H7A0.9291
C6—C11.376 (4)C7—H7B0.8995
C6—H60.9402O3—H3A0.9850
C5—C41.385 (5)O1—H1A0.9504
C5—C71.496 (4)
C2—C3—C4119.5 (3)C2—C1—C6119.5 (3)
C2—C3—H3117.7C2—C1—H1117.9
C4—C3—H3122.6C6—C1—H1122.6
C3—C2—C1120.3 (3)C3—C4—C5121.1 (3)
C3—C2—O3117.3 (3)C3—C4—H4119.2
C1—C2—O3122.4 (3)C5—C4—H4119.3
C5—C6—C1121.8 (3)C8—C7—C5113.3 (3)
C5—C6—H6127.1C8—C7—H7A100.2
C1—C6—H6111.1C5—C7—H7A112.5
C6—C5—C4117.9 (3)C8—C7—H7B117.4
C6—C5—C7121.6 (3)C5—C7—H7B122.0
C4—C5—C7120.5 (3)H7A—C7—H7B84.4
O2—C8—O1122.9 (3)C2—O3—H3A112.7
O2—C8—C7122.9 (3)C8—O1—H1A108.6
O1—C8—C7114.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O2i0.981.712.676 (4)166
O1—H1A···O3ii0.951.742.689 (3)175
Symmetry codes: (i) x+2, y1/2, z+1/2; (ii) x+3/2, y+1, z+1/2.
 

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