3-Carboxy­pyridine N-oxide: supramolecular aggregation through O—H...O and C—H...O interactions

In the crystal structure of the title mol­ecule, C₆H₅NO₃, weak C—H...O interactions result in dimeric units which are extended by strong O—H...O hydrogen bonds to form a two-dimensional supramolecular (4,4)-layered architecture.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.135
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.29

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

   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97.

3-Pyridylcarboxylate N-oxide

Crystal data

C6H5NO3	F(000) = 288
Mr = 139.11	Dx = 1.578 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P_2ybc	Cell parameters from 3276 reflections
a = 3.7879 (7) Å	θ = 2.4–28.0°
b = 10.624 (2) Å	µ = 0.13 mm^−1
c = 14.674 (3) Å	T = 293 K
β = 97.416 (3)°	Prism, colorless
V = 585.6 (2) Å^3	0.34 × 0.26 × 0.17 mm
Z = 4

Data collection

Bruker SMART 1000 diffractometer	1222 reflections with I > 2σ(I)
ω scans	Rint = 0.053
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	θmax = 28.0°
Tmin = 0.896, Tmax = 0.980	h = −5→4
3805 measured reflections	k = −12→14
1397 independent reflections	l = −16→19

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.045	w = 1/[σ^2(Fo^2) + (0.0765P)^2 + 0.147P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.136	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.38 e Å^−3
1397 reflections	Δρmin = −0.16 e Å^−3
91 parameters

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. Full-MATRIX

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

	x	y	z	Uiso*/Ueq
O3	0.0871 (3)	0.46164 (10)	0.37573 (7)	0.0393 (3)
N1	0.2759 (3)	0.36158 (10)	0.40793 (8)	0.0284 (3)
O1	0.6440 (3)	0.10738 (10)	0.23248 (7)	0.0422 (3)
H1	0.7230	0.0528	0.2012	0.051*
C3	0.3856 (4)	0.27695 (13)	0.34885 (9)	0.0287 (3)
H3A	0.3382	0.2902	0.2858	0.034*
O2	0.8243 (4)	−0.02483 (11)	0.34773 (8)	0.0496 (4)
C4	0.3453 (4)	0.34597 (13)	0.49991 (10)	0.0325 (3)
H4A	0.2696	0.4061	0.5392	0.039*
C2	0.5690 (3)	0.17041 (12)	0.38259 (9)	0.0278 (3)
C1	0.6911 (4)	0.07337 (13)	0.31886 (9)	0.0302 (3)
C6	0.6398 (4)	0.15194 (13)	0.47712 (9)	0.0323 (3)
H6A	0.7609	0.0805	0.5006	0.039*
C5	0.5277 (4)	0.24131 (14)	0.53559 (10)	0.0353 (4)
H5A	0.5755	0.2307	0.5989	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0506 (6)	0.0289 (5)	0.0419 (6)	0.0094 (4)	0.0196 (5)	0.0069 (4)
N1	0.0321 (6)	0.0239 (6)	0.0311 (6)	−0.0028 (4)	0.0115 (4)	0.0014 (4)
O1	0.0669 (8)	0.0330 (6)	0.0279 (5)	0.0115 (5)	0.0108 (5)	−0.0010 (4)
C3	0.0337 (7)	0.0289 (7)	0.0248 (6)	−0.0027 (5)	0.0084 (5)	−0.0001 (5)
O2	0.0754 (9)	0.0356 (7)	0.0387 (6)	0.0179 (6)	0.0114 (6)	0.0031 (5)
C4	0.0387 (7)	0.0314 (7)	0.0296 (7)	−0.0075 (5)	0.0124 (5)	−0.0054 (5)
C2	0.0292 (6)	0.0266 (6)	0.0284 (7)	−0.0040 (5)	0.0067 (5)	−0.0012 (5)
C1	0.0348 (7)	0.0275 (6)	0.0291 (6)	−0.0005 (5)	0.0066 (5)	−0.0001 (5)
C6	0.0360 (7)	0.0311 (7)	0.0297 (7)	−0.0011 (5)	0.0038 (5)	0.0026 (5)
C5	0.0430 (8)	0.0383 (8)	0.0249 (6)	−0.0061 (6)	0.0058 (5)	0.0001 (5)

Geometric parameters (Å, º)

O3—N1	1.3332 (15)	C4—C5	1.376 (2)
N1—C3	1.3511 (17)	C4—H4A	0.9300
N1—C4	1.3516 (18)	C2—C6	1.3923 (18)
O1—C1	1.3078 (17)	C2—C1	1.5043 (18)
O1—H1	0.8200	C6—C5	1.383 (2)
C3—C2	1.3857 (19)	C6—H6A	0.9300
C3—H3A	0.9300	C5—H5A	0.9300
O2—C1	1.2114 (18)
O3—N1—C3	119.90 (11)	C3—C2—C1	121.19 (12)
O3—N1—C4	118.56 (11)	C6—C2—C1	119.18 (12)
C3—N1—C4	121.52 (12)	O2—C1—O1	125.13 (13)
C1—O1—H1	109.5	O2—C1—C2	121.36 (13)
N1—C3—C2	119.73 (12)	O1—C1—C2	113.49 (12)
N1—C3—H3A	120.1	C5—C6—C2	119.10 (13)
C2—C3—H3A	120.1	C5—C6—H6A	120.5
N1—C4—C5	120.15 (13)	C2—C6—H6A	120.5
N1—C4—H4A	119.9	C4—C5—C6	119.87 (13)
C5—C4—H4A	119.9	C4—C5—H5A	120.1
C3—C2—C6	119.62 (12)	C6—C5—H5A	120.1
O3—N1—C3—C2	−177.33 (11)	C6—C2—C1—O2	5.9 (2)
C4—N1—C3—C2	1.0 (2)	C3—C2—C1—O1	7.51 (19)
O3—N1—C4—C5	177.53 (12)	C6—C2—C1—O1	−172.98 (12)
C3—N1—C4—C5	−0.8 (2)	C3—C2—C6—C5	−0.6 (2)
N1—C3—C2—C6	−0.3 (2)	C1—C2—C6—C5	179.93 (12)
N1—C3—C2—C1	179.21 (12)	N1—C4—C5—C6	−0.1 (2)
C3—C2—C1—O2	−173.62 (14)	C2—C6—C5—C4	0.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3^i	0.82	1.71	2.525 (2)	169
C4—H4A···O3^ii	0.93	2.41	3.311 (2)	164

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