3-(4-Carboxy­phen­oxy)propionic acid

Gao, S.; Ng, S.W.

doi:10.1107/S1600536806027577

3-(4-Carboxyphenoxy)propionic acid

S. Gao and S. W. Ng

The molecules of the title compound, C₁₀H₁₀O₅, are linked by O—H

O hydrogen bonds into a linear chain along [20 $\overline{1}$ ].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806027577/ci2104sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806027577/ci2104Isup2.hkl Contains datablock I

CCDC reference: 618167

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.002 Å
R factor = 0.046
wR factor = 0.153
Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.12 Ratio
PLAT731_ALERT_1_B Bond    Calc     0.83(5), Rep   0.830(10) ......       5.00 su-Ra
              O1   -H1O     1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.83(5), Rep   0.830(10) ......       5.00 su-Ra
              O1   -H1O     1.555   1.555

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.722     0.937
            Tmin(prime) and Tmax expected:      0.951     0.991
            RR(prime) =      0.803
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.80
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.06
PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ...     958.00 Ang-3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT731_ALERT_1_C Bond    Calc     0.83(4), Rep   0.840(10) ......       4.00 su-Ra
              O5   -H5O     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.83(4), Rep   0.840(10) ......       4.00 su-Ra
              O5   -H5O     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.81(5), Rep     1.82(2) ......       2.50 su-Ra
              H1O  -O4      1.555   2.664
PLAT736_ALERT_1_C H...A   Calc     1.85(4), Rep   1.850(10) ......       4.00 su-Ra
              H5O  -O2      1.555   2.465

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      1.057
            Tmax scaled      0.991 Tmin scaled      0.763

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

   7 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
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

3-(4-Carboxyphenoxy)propionic acid top

Crystal data top

C₁₀H₁₀O₅	F(000) = 440
M_r = 210.18	D_x = 1.457 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5947 reflections
a = 7.813 (4) Å	θ = 3.0–27.5°
b = 9.032 (6) Å	µ = 0.12 mm⁻¹
c = 13.631 (9) Å	T = 295 K
β = 94.92 (2)°	Plate, colourless
V = 958 (1) Å³	0.42 × 0.17 × 0.08 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	2188 independent reflections
Radiation source: fine-focus sealed tube	1359 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→8
T_min = 0.722, T_max = 0.937	k = −11→11
9176 measured reflections	l = −17→17

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0912P)²] where P = (F_o² + 2F_c²)/3
2188 reflections	(Δ/σ)_max = 0.001
144 parameters	Δρ_max = 0.23 e Å⁻³
2 restraints	Δρ_min = −0.20 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.7570 (2)	0.4302 (2)	0.2068 (1)	0.0650 (5)
O2	0.5369 (2)	0.52999 (2)	0.1178 (1)	0.0577 (4)
O3	0.3768 (2)	0.4912 (2)	0.3441 (1)	0.0454 (4)
O4	−0.0388 (2)	0.9064 (2)	0.6092 (1)	0.0628 (5)
O5	−0.2541 (2)	0.8132 (2)	0.5119 (1)	0.0608 (5)
C1	0.5972 (2)	0.4410 (2)	0.1810 (1)	0.0402 (4)
C2	0.4826 (2)	0.3328 (2)	0.2264 (2)	0.0461 (5)
C3	0.3230 (2)	0.4016 (2)	0.2608 (2)	0.0432 (5)
C4	0.2544 (2)	0.5667 (2)	0.3894 (1)	0.0380 (4)
C5	0.0802 (2)	0.5598 (2)	0.3607 (1)	0.0426 (5)
C6	−0.0322 (2)	0.6431 (2)	0.4101 (1)	0.0434 (5)
C7	0.0258 (2)	0.7344 (2)	0.4873 (1)	0.0392 (4)
C8	0.2008 (2)	0.7377 (2)	0.5162 (1)	0.0441 (5)
C9	0.3143 (2)	0.6542 (2)	0.4687 (1)	0.0441 (5)
C10	−0.0943 (2)	0.8237 (2)	0.5398 (1)	0.0432 (5)
H1O	0.804 (7)	0.494 (4)	0.174 (4)	0.21 (2)*
H5O	−0.325 (4)	0.856 (5)	0.544 (3)	0.18 (2)*
H2A	0.5466	0.2857	0.2820	0.055*
H2B	0.4493	0.2564	0.1785	0.055*
H3A	0.2656	0.4617	0.2089	0.052*
H3B	0.2442	0.3255	0.2790	0.052*
H5	0.0396	0.4995	0.3086	0.051*
H6	−0.1493	0.6379	0.3913	0.052*
H8	0.2414	0.7976	0.5686	0.053*
H9	0.4308	0.6560	0.4894	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0463 (8)	0.0904 (12)	0.0569 (10)	−0.0101 (8)	−0.0033 (7)	0.0161 (9)
O2	0.0430 (8)	0.0649 (10)	0.0663 (10)	0.0041 (7)	0.0112 (7)	0.0194 (8)
O3	0.0385 (7)	0.0534 (8)	0.0446 (8)	0.0016 (6)	0.0059 (6)	−0.0088 (6)
O4	0.0530 (9)	0.0779 (11)	0.0566 (10)	0.0052 (8)	0.0004 (7)	−0.0228 (8)
O5	0.0387 (8)	0.0706 (10)	0.0733 (11)	0.0035 (7)	0.0067 (7)	−0.0202 (8)
C1	0.0406 (9)	0.0434 (10)	0.0368 (10)	0.0016 (8)	0.0047 (8)	−0.0052 (8)
C2	0.0492 (11)	0.0406 (11)	0.0497 (12)	−0.0001 (9)	0.0117 (9)	−0.0005 (9)
C3	0.0409 (10)	0.0468 (10)	0.0425 (11)	−0.0033 (8)	0.0065 (8)	−0.0028 (8)
C4	0.0360 (9)	0.0422 (10)	0.0361 (10)	−0.0008 (8)	0.0049 (8)	0.0023 (8)
C5	0.0373 (9)	0.0488 (11)	0.0410 (10)	−0.0017 (8)	−0.0001 (8)	−0.0058 (9)
C6	0.0330 (9)	0.0523 (11)	0.0446 (11)	0.0001 (8)	0.0010 (8)	0.0005 (9)
C7	0.0374 (10)	0.0423 (10)	0.0384 (10)	0.0004 (8)	0.0057 (8)	0.0017 (8)
C8	0.0401 (10)	0.0500 (11)	0.0420 (11)	−0.0022 (8)	0.0011 (8)	−0.0060 (9)
C9	0.0336 (9)	0.0525 (11)	0.0455 (11)	−0.0014 (8)	−0.0003 (8)	−0.0027 (9)
C10	0.0390 (10)	0.0495 (11)	0.0413 (10)	−0.0007 (9)	0.0037 (9)	0.0016 (9)

Geometric parameters (Å, º) top

O1—C1	1.271 (2)	C7—C10	1.469 (3)
O2—C1	1.241 (2)	C8—C9	1.369 (3)
O3—C4	1.364 (2)	O1—H1O	0.83 (1)
O3—C3	1.428 (2)	O5—H5O	0.84 (1)
O4—C10	1.253 (2)	C2—H2A	0.97
O5—C10	1.277 (2)	C2—H2B	0.97
C1—C2	1.494 (3)	C3—H3A	0.97
C2—C3	1.504 (3)	C3—H3B	0.97
C4—C5	1.385 (2)	C5—H5	0.93
C4—C9	1.387 (3)	C6—H6	0.93
C5—C6	1.375 (3)	C8—H8	0.93
C6—C7	1.382 (3)	C9—H9	0.93
C7—C8	1.390 (2)

C4—O3—C3	118.3 (1)	C10—O5—H5O	119 (3)
O2—C1—O1	123.1 (2)	C1—C2—H2A	108.8
O2—C1—C2	120.3 (2)	C3—C2—H2A	108.8
O1—C1—C2	116.4 (2)	C1—C2—H2B	108.8
C1—C2—C3	113.7 (2)	C3—C2—H2B	108.8
O3—C3—C2	106.7 (2)	H2A—C2—H2B	107.7
O3—C4—C5	124.0 (2)	O3—C3—H3A	110.4
O3—C4—C9	115.7 (2)	C2—C3—H3A	110.4
C5—C4—C9	120.2 (2)	O3—C3—H3B	110.4
C6—C5—C4	119.4 (2)	C2—C3—H3B	110.4
C5—C6—C7	121.1 (2)	H3A—C3—H3B	108.6
C6—C7—C8	118.6 (2)	C6—C5—H5	120.3
C6—C7—C10	121.1 (2)	C4—C5—H5	120.3
C8—C7—C10	120.3 (2)	C5—C6—H6	119.4
C9—C8—C7	121.1 (2)	C7—C6—H6	119.4
C8—C9—C4	119.6 (2)	C9—C8—H8	119.5
O4—C10—O5	122.4 (2)	C7—C8—H8	119.5
O4—C10—C7	120.0 (2)	C8—C9—H9	120.2
O5—C10—C7	117.6 (2)	C4—C9—H9	120.2
C1—O1—H1O	106 (4)

O2—C1—C2—C3	−48.1 (3)	C5—C6—C7—C10	179.8 (2)
O1—C1—C2—C3	135.7 (2)	C6—C7—C8—C9	0.9 (3)
C4—O3—C3—C2	179.9 (2)	C10—C7—C8—C9	179.4 (2)
C1—C2—C3—O3	−69.8 (2)	C7—C8—C9—C4	1.1 (3)
C3—O3—C4—C5	1.3 (3)	O3—C4—C9—C8	177.7 (2)
C3—O3—C4—C9	−178.8 (2)	C5—C4—C9—C8	−2.3 (3)
O3—C4—C5—C6	−178.6 (2)	C6—C7—C10—O4	−179.6 (2)
C9—C4—C5—C6	1.5 (3)	C8—C7—C10—O4	1.9 (3)
C4—C5—C6—C7	0.5 (3)	C6—C7—C10—O5	0.4 (3)
C5—C6—C7—C8	−1.7 (3)	C8—C7—C10—O5	−178.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O4ⁱ	0.83 (1)	1.82 (2)	2.618 (2)	162 (5)
O5—H5O···O2ⁱⁱ	0.84 (1)	1.85 (1)	2.676 (2)	173 (5)

Symmetry codes: (i) x+1, −y+3/2, z−1/2; (ii) x−1, −y+3/2, z+1/2.

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