3-Hydro­xy­pyridinium 3-(carboxy­methoxy)­phenoxy­acetate

The crystal structure of the title compound, C₅H₆NO⁺·C₁₀H₉O₆^-, consists of pairs of 3-hydroxy­pyridinium cations and pairs of 3-(carboxy­methoxy)­phenoxy­acetate anions that are connected via hydrogen bonding into linear ribbons, which are approximately planar. The asymmetric unit consists of one cation and one anion, each located in a general position.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.057
• wR factor = 0.129
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.790     0.978
            Tmin' and Tmax expected:      0.956     0.978
            RR' =      0.827
            Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.83
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.23
PLAT731_ALERT_1_C Bond    Calc     0.87(3), Rep   0.870(10) ......       3.00 su-Rat
              N1   -H1N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.87(3), Rep   0.870(10) ......       3.00 su-Rat
              N1   -H1N     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.77(3), Rep   1.770(10) ......       3.00 su-Rat
              H1N  -O2      1.555   1.555

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

   5 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
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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-Hydroxypyridinium 3-(carboxymethoxy)phenoxyacetate

Crystal data

C5H6NO^+·C10H9O6^−	F(000) = 672
Mr = 321.28	Dx = 1.453 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6106 reflections
a = 15.960 (2) Å	θ = 4.4–27.5°
b = 4.8404 (4) Å	µ = 0.12 mm^−1
c = 20.313 (3) Å	T = 295 K
β = 110.58 (4)°	Prism, colorless
V = 1469.1 (3) Å^3	0.38 × 0.25 × 0.19 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	3367 independent reflections
Radiation source: fine-focus sealed tube	2121 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.063
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −20→20
Tmin = 0.790, Tmax = 0.978	k = −6→5
13092 measured reflections	l = −26→26

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.06P)^2 + 0.1723P] where P = (Fo^2 + 2Fc^2)/3
3367 reflections	(Δ/σ)max = 0.001
220 parameters	Δρmax = 0.20 e Å^−3
3 restraints	Δρmin = −0.19 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.5662 (1)	0.2796 (4)	0.3703 (1)	0.0528 (5)
O2	0.2829 (1)	0.4081 (3)	0.4844 (1)	0.0463 (4)
O3	0.3853 (1)	0.0884 (3)	0.5325 (1)	0.0489 (5)
O4	0.2085 (1)	0.3617 (3)	0.5784 (1)	0.0457 (4)
O5	−0.0262 (1)	0.7256 (3)	0.6457 (1)	0.0354 (4)
O6	−0.1579 (1)	1.0966 (4)	0.6316 (1)	0.0557 (5)
O7	−0.1488 (1)	1.2422 (3)	0.5298 (1)	0.0445 (4)
N1	0.3641 (1)	0.4975 (5)	0.3935 (1)	0.0493 (5)
C1	0.4409 (2)	0.3651 (5)	0.4055 (1)	0.0420 (6)
C2	0.4875 (1)	0.4008 (5)	0.3603 (1)	0.0372 (5)
C3	0.4512 (2)	0.5730 (5)	0.3028 (1)	0.0452 (6)
C4	0.3716 (2)	0.7053 (6)	0.2926 (1)	0.0584 (7)
C5	0.3283 (2)	0.6671 (6)	0.3393 (2)	0.0591 (8)
C6	0.3192 (1)	0.2306 (5)	0.5308 (1)	0.0352 (5)
C7	0.2821 (1)	0.1822 (5)	0.5889 (1)	0.0347 (5)
C8	0.1643 (1)	0.3542 (4)	0.6254 (1)	0.0302 (5)
C9	0.0929 (1)	0.5379 (4)	0.6099 (1)	0.0308 (5)
C10	0.0447 (1)	0.5515 (4)	0.6547 (1)	0.0278 (4)
C11	0.0670 (1)	0.3836 (4)	0.7136 (1)	0.0324 (5)
C12	0.1367 (1)	0.2012 (4)	0.7271 (1)	0.0340 (5)
C13	0.1869 (1)	0.1830 (4)	0.6835 (1)	0.0328 (5)
C14	−0.0514 (1)	0.8971 (4)	0.5857 (1)	0.0323 (5)
C15	−0.1257 (1)	1.0870 (5)	0.5866 (1)	0.0336 (5)
H1o	0.577 (2)	0.156 (5)	0.402 (1)	0.09 (1)*
H7o	−0.191 (1)	1.348 (5)	0.530 (2)	0.09 (1)*
H1n	0.334 (2)	0.466 (6)	0.421 (1)	0.07 (1)*
H1	0.4632	0.2488	0.4443	0.050*
H3	0.4807	0.5989	0.2711	0.054*
H4	0.3472	0.8209	0.2540	0.070*
H5	0.2747	0.7581	0.3332	0.071*
H7a	0.2630	−0.0084	0.5882	0.042*
H7b	0.3280	0.2184	0.6343	0.042*
H9	0.0779	0.6497	0.5702	0.037*
H11	0.0348	0.3945	0.7437	0.039*
H12	0.1508	0.0871	0.7664	0.041*
H13	0.2343	0.0594	0.6931	0.039*
H14a	−0.0714	0.7845	0.5435	0.039*
H14b	−0.0004	1.0051	0.5854	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.052 (1)	0.068 (1)	0.049 (1)	0.025 (1)	0.031 (1)	0.018 (1)
O2	0.048 (1)	0.056 (1)	0.044 (1)	0.023 (1)	0.028 (1)	0.020 (1)
O3	0.047 (1)	0.060 (1)	0.050 (1)	0.025 (1)	0.030 (1)	0.017 (1)
O4	0.046 (1)	0.058 (1)	0.045 (1)	0.027 (1)	0.031 (1)	0.022 (1)
O5	0.040 (1)	0.038 (1)	0.036 (1)	0.012 (1)	0.022 (1)	0.008 (1)
O6	0.054 (1)	0.072 (1)	0.053 (1)	0.027 (1)	0.034 (1)	0.014 (1)
O7	0.048 (1)	0.048 (1)	0.042 (1)	0.021 (1)	0.023 (1)	0.013 (1)
N1	0.049 (1)	0.063 (1)	0.047 (1)	0.007 (1)	0.032 (1)	0.001 (1)
C1	0.047 (1)	0.050 (1)	0.034 (1)	0.007 (1)	0.021 (1)	0.004 (1)
C2	0.041 (1)	0.042 (1)	0.034 (1)	0.006 (1)	0.018 (1)	0.002 (1)
C3	0.050 (1)	0.056 (2)	0.037 (1)	0.011 (1)	0.025 (1)	0.010 (1)
C4	0.059 (2)	0.070 (2)	0.050 (2)	0.023 (2)	0.023 (1)	0.020 (1)
C5	0.049 (1)	0.074 (2)	0.061 (2)	0.026 (2)	0.027 (1)	0.013 (2)
C6	0.034 (1)	0.041 (1)	0.034 (1)	0.008 (1)	0.016 (1)	0.004 (1)
C7	0.032 (1)	0.041 (1)	0.035 (1)	0.010 (1)	0.015 (1)	0.005 (1)
C8	0.030 (1)	0.033 (1)	0.031 (1)	0.002 (1)	0.015 (1)	0.001 (1)
C9	0.033 (1)	0.032 (1)	0.029 (1)	0.006 (1)	0.014 (1)	0.007 (1)
C10	0.030 (1)	0.027 (1)	0.029 (1)	0.001 (1)	0.012 (1)	−0.002 (1)
C11	0.037 (1)	0.036 (1)	0.030 (1)	0.001 (1)	0.018 (1)	0.002 (1)
C12	0.038 (1)	0.035 (1)	0.029 (1)	0.002 (1)	0.011 (1)	0.008 (1)
C13	0.031 (1)	0.032 (1)	0.035 (1)	0.005 (1)	0.011 (1)	0.005 (1)
C14	0.035 (1)	0.034 (1)	0.031 (1)	0.006 (1)	0.015 (1)	0.004 (1)
C15	0.032 (1)	0.036 (1)	0.035 (1)	0.003 (1)	0.013 (1)	−0.002 (1)

Geometric parameters (Å, º)

O1—C2	1.334 (3)	C10—C11	1.385 (3)
O2—C6	1.257 (3)	C11—C12	1.370 (3)
O3—C6	1.250 (2)	C12—C13	1.391 (3)
O4—C8	1.374 (2)	C14—C15	1.506 (3)
O4—C7	1.416 (2)	O1—H1o	0.86 (1)
O5—C10	1.371 (2)	O7—H7o	0.85 (1)
O5—C14	1.410 (2)	N1—H1n	0.87 (1)
O6—C15	1.196 (2)	C1—H1	0.93
O7—C15	1.318 (3)	C3—H3	0.93
N1—C1	1.327 (3)	C4—H4	0.93
N1—C5	1.331 (3)	C5—H5	0.93
C1—C2	1.383 (3)	C7—H7a	0.97
C2—C3	1.385 (3)	C7—H7b	0.97
C3—C4	1.372 (3)	C9—H9	0.93
C4—C5	1.369 (4)	C11—H11	0.93
C6—C7	1.514 (3)	C12—H12	0.93
C8—C9	1.391 (3)	C13—H13	0.93
C8—C13	1.382 (3)	C14—H14a	0.97
C9—C10	1.384 (3)	C14—H14b	0.97
C7—O4—C8	118.7 (2)	C15—O7—H7o	108 (2)
C10—O5—C14	116.7 (2)	C1—N1—H1n	119 (2)
C1—N1—C5	123.4 (2)	C5—N1—H1n	117 (2)
N1—C1—C2	119.7 (2)	N1—C1—H1	120.2
O1—C2—C1	122.7 (2)	C2—C1—H1	120.2
O1—C2—C3	119.1 (2)	C4—C3—H3	120.0
C1—C2—C3	118.2 (2)	C2—C3—H3	120.0
C2—C3—C4	120.0 (2)	C5—C4—H4	120.0
C3—C4—C5	120.0 (2)	C3—C4—H4	120.0
N1—C5—C4	118.8 (2)	N1—C5—H5	120.6
O3—C6—O2	124.0 (2)	C4—C5—H5	120.6
O3—C6—C7	116.8 (2)	O4—C7—H7a	110.0
O2—C6—C7	119.2 (2)	C6—C7—H7a	110.0
O4—C7—C6	108.5 (2)	O4—C7—H7b	110.0
O4—C8—C13	124.4 (2)	C6—C7—H7b	110.0
O4—C8—C9	114.0 (2)	H7a—C7—H7b	108.4
C9—C8—C13	121.6 (2)	C10—C9—H9	120.6
C8—C9—C10	118.8 (2)	C8—C9—H9	120.6
O5—C10—C9	124.4 (2)	C12—C11—H11	120.1
O5—C10—C11	115.2 (2)	C10—C11—H11	120.1
C9—C10—C11	120.4 (2)	C11—C12—H12	119.3
C10—C11—C12	119.7 (2)	C13—C12—H12	119.3
C11—C12—C13	121.4 (2)	C8—C13—H13	121.0
C8—C13—C12	118.0 (2)	C12—C13—H13	121.0
O5—C14—C15	109.6 (2)	O5—C14—H14a	109.8
O6—C15—O7	125.8 (2)	C15—C14—H14a	109.7
O6—C15—C14	125.8 (2)	O5—C14—H14b	109.7
O7—C15—C14	108.4 (2)	C15—C14—H14b	109.8
C2—O1—H1o	111 (2)	H14a—C14—H14b	108.2
C5—N1—C1—C2	−0.1 (4)	C13—C8—C9—C10	1.0 (3)
N1—C1—C2—O1	178.2 (2)	C14—O5—C10—C9	1.1 (3)
N1—C1—C2—C3	−0.8 (4)	C14—O5—C10—C11	−179.2 (2)
O1—C2—C3—C4	−178.3 (2)	C8—C9—C10—O5	179.3 (2)
C1—C2—C3—C4	0.9 (4)	C8—C9—C10—C11	−0.4 (3)
C2—C3—C4—C5	0.0 (4)	O5—C10—C11—C12	179.7 (2)
C1—N1—C5—C4	1.0 (4)	C9—C10—C11—C12	−0.6 (3)
C3—C4—C5—N1	−1.0 (4)	C10—C11—C12—C13	0.9 (3)
C8—O4—C7—C6	−179.8 (2)	O4—C8—C13—C12	179.0 (2)
O3—C6—C7—O4	179.7 (2)	C9—C8—C13—C12	−0.7 (3)
O2—C6—C7—O4	−0.2 (3)	C11—C12—C13—C8	−0.3 (3)
C7—O4—C8—C13	0.5 (3)	C10—O5—C14—C15	−176.2 (2)
C7—O4—C8—C9	−179.8 (2)	O5—C14—C15—O6	1.2 (3)
O4—C8—C9—C10	−178.7 (2)	O5—C14—C15—O7	−179.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O2	0.87 (1)	1.77 (1)	2.638 (3)	173 (3)
O1—H1o···O3^i	0.86 (1)	1.72 (1)	2.569 (2)	172 (3)
O7—H7o···O2^ii	0.85 (1)	1.82 (1)	2.663 (2)	170 (3)

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