2-[Hydro­xy(2-pyridyl)­methyl]-2-cyclopenten-1-one: the Baylis–Hillman adduct of 2-pyridine­carbox­aldehyde and 2-cyclo­penten-1-one

In the title compound, C₁₁H₁₁NO₂, the cyclo­pentene ring is planar to within 0.025 (2) Å. The dihedral angle between the cyclo­pentene plane and the pyridine ring plane is 83.1 (1)°. Strong intermolecular O—H...N hydrogen bonds link the mol­ecules into a chain which runs parallel to the a axis and has a graph-set motif of C(5). Weak C—H...O interactions form a three-dimensional network in the crystal stucture.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.095
• Data-to-parameter ratio = 9.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

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           26.97
           From the CIF: _reflns_number_total               1217
           Count of symmetry unique reflns         1218
           Completeness (_total/calc)             99.92%
           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
   0 ALERT level B = Potentially serious problem
   1 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
   0 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: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

2-[hydroxy(2-pyridyl)methyl]-2-cyclopenten-1-one

Crystal data

C11H11NO2	Dx = 1.310 Mg m^−3
Mr = 189.21	Melting point: 388 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4137 reflections
a = 8.427 (2) Å	θ = 2.7–22.9°
b = 10.200 (2) Å	µ = 0.09 mm^−1
c = 11.163 (3) Å	T = 293 K
V = 959.5 (4) Å^3	Block, colourless
Z = 4	0.30 × 0.20 × 0.20 mm
F(000) = 400

Data collection

Bruker SMART 1K CCD area-detector diffractometer	1217 independent reflections
Radiation source: fine-focus sealed tube	1108 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 27.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
Tmin = 0.973, Tmax = 0.982	k = −13→11
5333 measured reflections	l = −14→7

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.05P)^2 + 0.1216P] where P = (Fo^2 + 2Fc^2)/3
1217 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.16 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.

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	0.54339 (15)	0.24789 (15)	0.36429 (14)	0.0572 (4)
H1	0.6013	0.3028	0.3955	0.086*
O2	0.3307 (2)	0.52112 (16)	0.4531 (2)	0.0877 (6)
N	0.24356 (19)	0.06904 (16)	0.52646 (15)	0.0488 (4)
C7	0.3596 (2)	0.09379 (17)	0.44780 (17)	0.0410 (4)
C8	0.4347 (3)	−0.00488 (19)	0.38531 (18)	0.0532 (5)
H8	0.5150	0.0144	0.3309	0.064*
C9	0.3880 (3)	−0.1337 (2)	0.4052 (2)	0.0630 (6)
H9	0.4357	−0.2019	0.3633	0.076*
C10	0.2721 (3)	−0.1592 (2)	0.4865 (2)	0.0604 (6)
H10	0.2407	−0.2449	0.5023	0.073*
C11	0.2026 (3)	−0.0563 (2)	0.5445 (2)	0.0591 (6)
H11	0.1225	−0.0741	0.5994	0.071*
C2	0.2708 (2)	0.31116 (18)	0.36972 (16)	0.0434 (4)
C1	0.2545 (3)	0.4540 (2)	0.3846 (2)	0.0554 (5)
C5	0.1252 (3)	0.5001 (3)	0.3022 (2)	0.0732 (7)
H5A	0.1677	0.5580	0.2412	0.088*
H5B	0.0439	0.5467	0.3467	0.088*
C4	0.0574 (3)	0.3763 (3)	0.2458 (2)	0.0776 (8)
H4A	−0.0525	0.3636	0.2690	0.093*
H4B	0.0638	0.3801	0.1591	0.093*
C3	0.1598 (3)	0.2701 (2)	0.29421 (19)	0.0598 (5)
H3	0.1471	0.1824	0.2734	0.072*
C6	0.4011 (2)	0.23686 (17)	0.43135 (16)	0.0420 (4)
H6	0.4185	0.2759	0.5105	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0450 (7)	0.0610 (9)	0.0657 (9)	−0.0104 (6)	0.0031 (7)	−0.0064 (8)
O2	0.0738 (11)	0.0456 (8)	0.1436 (18)	0.0030 (8)	−0.0178 (12)	−0.0234 (11)
N	0.0435 (8)	0.0410 (8)	0.0620 (10)	0.0061 (7)	0.0033 (8)	0.0009 (7)
C7	0.0394 (8)	0.0411 (9)	0.0424 (9)	0.0043 (7)	−0.0066 (8)	−0.0022 (7)
C8	0.0587 (12)	0.0500 (11)	0.0509 (10)	0.0097 (9)	0.0025 (10)	−0.0046 (9)
C9	0.0804 (15)	0.0420 (11)	0.0665 (13)	0.0156 (11)	−0.0072 (14)	−0.0111 (10)
C10	0.0675 (13)	0.0390 (9)	0.0748 (13)	0.0024 (10)	−0.0132 (13)	0.0052 (10)
C11	0.0524 (11)	0.0479 (11)	0.0769 (14)	0.0017 (9)	0.0024 (11)	0.0100 (11)
C2	0.0471 (10)	0.0423 (9)	0.0409 (9)	−0.0003 (8)	0.0004 (8)	0.0018 (7)
C1	0.0486 (10)	0.0452 (10)	0.0725 (13)	0.0049 (10)	0.0042 (11)	0.0054 (10)
C5	0.0654 (14)	0.0729 (15)	0.0811 (15)	0.0235 (13)	0.0119 (14)	0.0295 (14)
C4	0.0644 (14)	0.114 (2)	0.0542 (12)	0.0280 (15)	−0.0126 (12)	0.0062 (14)
C3	0.0584 (12)	0.0670 (13)	0.0541 (11)	0.0090 (11)	−0.0121 (10)	−0.0080 (11)
C6	0.0418 (9)	0.0413 (9)	0.0429 (8)	−0.0015 (7)	−0.0054 (8)	−0.0038 (8)

Geometric parameters (Å, º)

N—C7	1.338 (2)	C1—C5	1.502 (3)
C7—C8	1.379 (3)	O2—C1	1.211 (3)
C8—C9	1.389 (3)	O1—H1	0.82
C9—C10	1.359 (3)	C8—H8	0.93
C10—C11	1.365 (3)	C9—H9	0.93
N—C11	1.339 (3)	C10—H10	0.93
C7—C6	1.512 (2)	C11—H11	0.93
O1—C6	1.418 (2)	C5—H5A	0.97
C2—C6	1.501 (3)	C5—H5B	0.97
C2—C1	1.473 (3)	C4—H4A	0.97
C2—C3	1.327 (3)	C4—H4B	0.97
C4—C3	1.487 (3)	C3—H3	0.93
C5—C4	1.522 (4)	C6—H6	0.98
C7—N—C11	117.83 (17)	C9—C10—H10	120.7
N—C7—C8	121.99 (17)	C11—C10—H10	120.7
C7—C8—C9	118.6 (2)	C4—C5—H5A	110.7
C10—C9—C8	119.5 (2)	C1—C5—H5B	110.7
C9—C10—C11	118.5 (2)	C4—C5—H5B	110.7
N—C11—C10	123.5 (2)	C10—C11—H11	118.2
N—C7—C6	115.52 (15)	H5A—C5—H5B	108.8
C8—C7—C6	122.48 (17)	N—C11—H11	118.2
O1—C6—C2	109.67 (15)	C3—C4—H4A	111.0
O1—C6—C7	109.65 (15)	C5—C4—H4A	111.0
C2—C6—C7	111.94 (15)	C3—C4—H4B	111.0
C3—C2—C1	108.57 (19)	C5—C4—H4B	111.0
C3—C2—C6	130.34 (18)	H4A—C4—H4B	109.0
C1—C2—C6	121.05 (17)	C2—C3—H3	122.9
O2—C1—C2	125.5 (2)	C4—C3—H3	122.9
O2—C1—C5	126.5 (2)	O1—C6—H6	108.5
C2—C3—C4	114.2 (2)	C2—C6—H6	108.5
C2—C1—C5	107.9 (2)	C7—C6—H6	108.5
C3—C4—C5	103.66 (18)	C7—C8—H8	120.7
C1—C5—C4	105.45 (19)	C9—C8—H8	120.7
C6—O1—H1	109.5	C10—C9—H9	120.3
C1—C5—H5A	110.7	C8—C9—H9	120.3
C11—N—C7—C8	0.8 (3)	C2—C1—C5—C4	4.4 (3)
C11—N—C7—C6	−179.85 (19)	C1—C5—C4—C3	−3.5 (2)
N—C7—C8—C9	−0.1 (3)	C1—C2—C3—C4	1.4 (3)
C6—C7—C8—C9	−179.4 (2)	C6—C2—C3—C4	−176.2 (2)
C7—C8—C9—C10	−1.0 (3)	C5—C4—C3—C2	1.4 (3)
C8—C9—C10—C11	1.4 (3)	C3—C2—C6—O1	95.4 (2)
C7—N—C11—C10	−0.4 (3)	C1—C2—C6—O1	−81.9 (2)
C9—C10—C11—N	−0.7 (4)	C3—C2—C6—C7	−26.5 (3)
C3—C2—C1—O2	175.1 (2)	C1—C2—C6—C7	156.17 (18)
C6—C2—C1—O2	−7.1 (3)	N—C7—C6—O1	169.03 (14)
C3—C2—C1—C5	−3.7 (3)	C8—C7—C6—O1	−11.6 (2)
C6—C2—C1—C5	174.14 (17)	N—C7—C6—C2	−69.0 (2)
O2—C1—C5—C4	−174.3 (2)	C8—C7—C6—C2	110.34 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N^i	0.82	1.98	2.796 (2)	178
C11—H11···O2^ii	0.93	2.58	3.154 (3)	120
C9—H9···O1^iii	0.93	2.60	3.293 (3)	132
C10—H10···O2^iv	0.93	2.56	3.319 (3)	139
C8—H8···O1	0.93	2.42	2.746 (3)	100

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