1,4-Di­methyl-1,5,6,7-tetra­hydro-2H-cyclo­penta­[b]­pyridin-2-one

In the pyridone ring of the title compound, C₁₀H₁₃NO, single and double bonds alternate, though allowing some degree of delocalization.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.103
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           74.89
           From the CIF: _reflns_number_total               1740
           From the CIF: _diffrn_reflns_limit_ max hkl   10.    8.   16.
           From the CIF: _diffrn_reflns_limit_ min hkl  -12.    0.    0.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   12.    8.   19.
           Calculated minimum hkl  -12.   -8.  -19.

   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
   1 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: CAD-4 EXPRESS; cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1,4-dimethyl-1,5,6,7-tetrahydro-2H-cyclopenta[b]pyridin-2-one

Crystal data

C10H13NO	F(000) = 352
Mr = 163.21	Dx = 1.251 Mg m^−3
Monoclinic, P21/c	Melting point: 383 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.5418 Å
a = 9.7125 (15) Å	Cell parameters from 25 reflections
b = 6.8262 (16) Å	θ = 30–33°
c = 15.285 (3) Å	µ = 0.64 mm^−1
β = 121.233 (11)°	T = 293 K
V = 866.5 (3) Å^3	Prism, colourless
Z = 4	0.43 × 0.40 × 0.36 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.001
Radiation source: fine-focus sealed tube	θmax = 74.9°, θmin = 5.3°
Graphite monochromator	h = −12→10
non–profiled ω scans	k = 0→8
1740 measured reflections	l = 0→16
1740 independent reflections	1 standard reflections every 200 reflections
1183 reflections with I > 2σ(I)	intensity decay: 2%

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H-atom parameters constrained
S = 0.87	w = 1/[σ^2(Fo^2) + (0.0733P)^2] where P = (Fo^2 + 2Fc^2)/3
1740 reflections	(Δ/σ)max < 0.001
111 parameters	Δρmax = 0.18 e Å^−3
3 restraints	Δρmin = −0.16 e Å^−3

Special details

Experimental. ¹H NMR spectrum was recorded on a Bruker AMX–400. Atoms are numbered according to Fig. 1.

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

	x	y	z	Uiso*/Ueq
N1	0.69836 (12)	0.94894 (16)	0.22243 (8)	0.0464 (3)
C2	0.77458 (16)	0.7657 (2)	0.25108 (9)	0.0505 (3)
O2	0.76782 (14)	0.66679 (17)	0.31733 (8)	0.0735 (4)
C3	0.85733 (15)	0.7086 (2)	0.20056 (9)	0.0493 (3)
H3	0.9128	0.5903	0.2192	0.059*
C4	0.85993 (14)	0.81668 (19)	0.12692 (9)	0.0444 (3)
C5	0.77345 (15)	0.99668 (18)	0.09830 (9)	0.0430 (3)
C6	0.75942 (18)	1.1479 (2)	0.02242 (11)	0.0578 (4)
H6A	0.7213	1.0895	−0.0442	0.069*
H6B	0.8621	1.2112	0.0455	0.069*
C7	0.63584 (19)	1.2939 (2)	0.01846 (11)	0.0588 (4)
H7A	0.6735	1.4271	0.0225	0.071*
H7B	0.5336	1.2792	−0.0452	0.071*
C8	0.61549 (18)	1.2512 (2)	0.10903 (11)	0.0563 (4)
H8A	0.6674	1.3508	0.1616	0.068*
H8B	0.5026	1.2436	0.0877	0.068*
C9	0.69713 (14)	1.05589 (17)	0.14644 (9)	0.0419 (3)
C10	0.95316 (19)	0.7562 (2)	0.07853 (12)	0.0632 (4)
H10A	1.0449	0.8404	0.1020	0.095*
H10B	0.8857	0.7661	0.0055	0.095*
H10C	0.9888	0.6233	0.0970	0.095*
C11	0.6208 (2)	1.0223 (3)	0.27586 (13)	0.0658 (4)
H11A	0.6550	1.1544	0.2978	0.099*
H11B	0.6502	0.9413	0.3344	0.099*
H11C	0.5060	1.0194	0.2306	0.099*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0476 (6)	0.0512 (6)	0.0421 (6)	−0.0042 (5)	0.0245 (5)	−0.0032 (5)
C2	0.0476 (7)	0.0545 (8)	0.0420 (7)	−0.0037 (6)	0.0181 (5)	0.0048 (6)
O2	0.0823 (8)	0.0787 (8)	0.0630 (7)	0.0045 (6)	0.0402 (6)	0.0234 (6)
C3	0.0464 (7)	0.0478 (7)	0.0454 (7)	0.0041 (6)	0.0179 (5)	0.0028 (6)
C4	0.0399 (6)	0.0486 (7)	0.0406 (6)	−0.0027 (5)	0.0180 (5)	−0.0053 (5)
C5	0.0446 (6)	0.0437 (7)	0.0395 (6)	−0.0036 (5)	0.0210 (5)	−0.0005 (5)
C6	0.0663 (9)	0.0566 (8)	0.0561 (8)	−0.0016 (7)	0.0358 (7)	0.0068 (6)
C7	0.0643 (8)	0.0476 (7)	0.0575 (8)	−0.0005 (6)	0.0266 (7)	0.0052 (6)
C8	0.0588 (8)	0.0437 (8)	0.0663 (9)	0.0022 (6)	0.0324 (7)	−0.0012 (6)
C9	0.0428 (6)	0.0399 (6)	0.0419 (6)	−0.0055 (5)	0.0212 (5)	−0.0034 (5)
C10	0.0614 (8)	0.0692 (10)	0.0660 (9)	0.0078 (8)	0.0379 (7)	−0.0040 (8)
C11	0.0720 (10)	0.0743 (11)	0.0667 (9)	−0.0005 (8)	0.0470 (8)	−0.0029 (8)

Geometric parameters (Å, º)

N1—C9	1.3666 (16)	C6—H6B	0.9700
N1—C2	1.4027 (18)	C7—C8	1.525 (2)
N1—C11	1.4574 (17)	C7—H7A	0.9700
C2—O2	1.2469 (16)	C7—H7B	0.9700
C2—C3	1.427 (2)	C8—C9	1.5044 (18)
C3—C4	1.3568 (19)	C8—H8A	0.9700
C3—H3	0.9300	C8—H8B	0.9700
C4—C5	1.4232 (18)	C10—H10A	0.9600
C4—C10	1.4940 (19)	C10—H10B	0.9600
C5—C9	1.3490 (17)	C10—H10C	0.9600
C5—C6	1.5052 (18)	C11—H11A	0.9600
C6—C7	1.537 (2)	C11—H11B	0.9600
C6—H6A	0.9700	C11—H11C	0.9600
C9—N1—C2	120.81 (10)	C8—C7—H7B	110.1
C9—N1—C11	120.91 (12)	C6—C7—H7B	110.1
C2—N1—C11	118.28 (11)	H7A—C7—H7B	108.5
O2—C2—N1	119.67 (13)	C9—C8—C7	102.93 (11)
O2—C2—C3	124.94 (14)	C9—C8—H8A	111.2
N1—C2—C3	115.38 (11)	C7—C8—H8A	111.2
C4—C3—C2	123.92 (13)	C9—C8—H8B	111.2
C4—C3—H3	118.0	C7—C8—H8B	111.2
C2—C3—H3	118.0	H8A—C8—H8B	109.1
C3—C4—C5	117.55 (12)	C5—C9—N1	122.57 (12)
C3—C4—C10	122.49 (13)	C5—C9—C8	112.87 (11)
C5—C4—C10	119.93 (12)	N1—C9—C8	124.55 (11)
C9—C5—C4	119.64 (11)	C4—C10—H10A	109.5
C9—C5—C6	111.04 (12)	C4—C10—H10B	109.5
C4—C5—C6	129.21 (12)	H10A—C10—H10B	109.5
C5—C6—C7	103.41 (11)	C4—C10—H10C	109.5
C5—C6—H6A	111.1	H10A—C10—H10C	109.5
C7—C6—H6A	111.1	H10B—C10—H10C	109.5
C5—C6—H6B	111.1	N1—C11—H11A	109.5
C7—C6—H6B	111.1	N1—C11—H11B	109.5
H6A—C6—H6B	109.0	H11A—C11—H11B	109.5
C8—C7—C6	107.84 (12)	N1—C11—H11C	109.5
C8—C7—H7A	110.1	H11A—C11—H11C	109.5
C6—C7—H7A	110.1	H11B—C11—H11C	109.5