1-(4-Chloro­phen­acyl)-4-methyl-6,7,8,9-tetra­hydro-5H-cyclo­hepta­[b]­pyridin-2(1H)-one

In the pyridone ring of the title compound, C₁₉H₂₀ClNO₂, single and double bonds alternate, though allowing some degree of conjugation. One C atom in the cyclo­heptene ring is disordered over two positions, which form boat and chair conformations of cyclo­heptene, respectively.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.106
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.96

Author Response: Not collected reflections were marked as collisions.

Alert level C
PLAT301_ALERT_3_C Main Residue  Disorder .........................       4.00 Perc.

   0 ALERT level A = In general: serious problem
   1 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
   0 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: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; 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-Chlorophenacyl)-4-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-2(1H)- one

Crystal data

C19H20ClNO2	Z = 2
Mr = 329.81	F(000) = 348.0
Triclinic, P1	Dx = 1.356 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.5418 Å
a = 7.9540 (7) Å	Cell parameters from 25 reflections
b = 8.6902 (7) Å	θ = 30–35°
c = 12.4984 (8) Å	µ = 2.16 mm^−1
α = 108.342 (6)°	T = 293 K
β = 94.660 (6)°	Prism, colourless
γ = 96.760 (7)°	0.30 × 0.30 × 0.30 mm
V = 807.88 (11) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.0002
Radiation source: fine–focus sealed tube	θmax = 74.7°, θmin = 3.8°
Graphite monochromator	h = −9→9
non–profiled ω scans	k = −10→10
3173 measured reflections	l = 0→15
3173 independent reflections	1 standard reflections every 200 reflections
2843 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0448P)^2 + 0.3555P] where P = (Fo^2 + 2Fc^2)/3
3173 reflections	(Δ/σ)max = 0.001
219 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	1.34240 (7)	1.05754 (6)	0.59895 (4)	0.07539 (19)
N1	0.64715 (15)	0.41444 (14)	0.08032 (9)	0.0386 (3)
C2	0.6792 (2)	0.2983 (2)	−0.01944 (12)	0.0459 (4)
O2	0.82209 (17)	0.30684 (18)	−0.05217 (11)	0.0664 (4)
C3	0.5371 (2)	0.1741 (2)	−0.07630 (13)	0.0506 (4)
H3	0.5499	0.0962	−0.1447	0.061*
C4	0.3847 (2)	0.16427 (18)	−0.03546 (13)	0.0460 (4)
C5	0.36028 (19)	0.28514 (18)	0.06748 (13)	0.0431 (3)
C6	0.1958 (2)	0.2811 (3)	0.11924 (17)	0.0600 (5)
H6A	0.1065	0.2075	0.0627	0.072*
H6B	0.1634	0.3899	0.1410	0.072*
C7	0.2101 (3)	0.2245 (3)	0.22403 (18)	0.0665 (5)
H7A	0.1162	0.2562	0.2669	0.080*
H7B	0.1983	0.1058	0.1987	0.080*
C8A	0.3758 (8)	0.2940 (6)	0.3019 (4)	0.0816 (19)	0.689 (10)
H8A	0.3614	0.2720	0.3723	0.098*	0.689 (10)
H8B	0.4621	0.2313	0.2675	0.098*	0.689 (10)
C8B	0.2867 (13)	0.3585 (12)	0.3297 (7)	0.066 (2)	0.311 (10)
H8C	0.2011	0.4291	0.3527	0.079*	0.311 (10)
H8D	0.3064	0.3089	0.3882	0.079*	0.311 (10)
C9	0.4447 (3)	0.4642 (3)	0.33150 (16)	0.0772 (6)
H9A	0.5541	0.4827	0.3775	0.093*
H9B	0.3697	0.5276	0.3790	0.093*
C10	0.4711 (2)	0.5335 (2)	0.23369 (14)	0.0535 (4)
H10A	0.3735	0.5854	0.2208	0.064*
H10B	0.5710	0.6175	0.2568	0.064*
C11	0.49385 (18)	0.40686 (17)	0.12333 (12)	0.0387 (3)
C12	0.2434 (3)	0.0259 (2)	−0.09912 (18)	0.0700 (6)
H12A	0.2836	−0.0459	−0.1641	0.105*
H12B	0.1479	0.0699	−0.1237	0.105*
H12C	0.2087	−0.0344	−0.0501	0.105*
C13	0.7917 (2)	0.54131 (19)	0.14072 (12)	0.0444 (3)
H13A	0.7556	0.6483	0.1575	0.053*
H13B	0.8815	0.5374	0.0923	0.053*
C14	0.86119 (19)	0.51899 (18)	0.25049 (13)	0.0430 (3)
O14	0.82045 (17)	0.39207 (14)	0.26938 (11)	0.0618 (3)
C15	0.97934 (19)	0.65812 (18)	0.33448 (12)	0.0413 (3)
C16	1.0785 (2)	0.77602 (19)	0.30370 (13)	0.0443 (3)
H16	1.0691	0.7727	0.2283	0.053*
C17	1.1911 (2)	0.8985 (2)	0.38501 (14)	0.0505 (4)
H17	1.2594	0.9766	0.3646	0.061*
C18	1.2007 (2)	0.9032 (2)	0.49672 (13)	0.0498 (4)
C19	1.1025 (2)	0.7904 (2)	0.52965 (14)	0.0577 (4)
H19	1.1108	0.7959	0.6054	0.069*
C20	0.9905 (2)	0.6681 (2)	0.44815 (14)	0.0529 (4)
H20	0.9217	0.5914	0.4696	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0714 (3)	0.0672 (3)	0.0584 (3)	−0.0067 (2)	−0.0145 (2)	−0.0087 (2)
N1	0.0404 (6)	0.0407 (6)	0.0312 (6)	−0.0043 (5)	−0.0027 (5)	0.0123 (5)
C2	0.0529 (9)	0.0522 (9)	0.0316 (7)	0.0042 (7)	0.0012 (6)	0.0146 (6)
O2	0.0577 (8)	0.0882 (10)	0.0485 (7)	0.0053 (7)	0.0147 (6)	0.0160 (6)
C3	0.0659 (10)	0.0456 (8)	0.0331 (7)	0.0033 (7)	−0.0058 (7)	0.0077 (6)
C4	0.0550 (9)	0.0382 (7)	0.0402 (8)	−0.0047 (6)	−0.0139 (7)	0.0153 (6)
C5	0.0415 (7)	0.0441 (8)	0.0431 (8)	−0.0019 (6)	−0.0058 (6)	0.0192 (6)
C6	0.0413 (8)	0.0698 (11)	0.0703 (12)	−0.0005 (8)	0.0004 (8)	0.0294 (9)
C7	0.0591 (11)	0.0740 (12)	0.0742 (13)	0.0002 (9)	0.0176 (10)	0.0364 (10)
C8A	0.106 (4)	0.079 (3)	0.064 (2)	−0.012 (2)	−0.009 (2)	0.0433 (19)
C8B	0.070 (5)	0.070 (5)	0.071 (4)	0.016 (4)	0.014 (4)	0.038 (4)
C9	0.0917 (15)	0.0893 (15)	0.0418 (10)	−0.0120 (12)	0.0089 (10)	0.0182 (10)
C10	0.0603 (10)	0.0478 (9)	0.0453 (9)	0.0010 (7)	0.0090 (8)	0.0073 (7)
C11	0.0428 (7)	0.0375 (7)	0.0347 (7)	0.0010 (6)	−0.0003 (6)	0.0132 (5)
C12	0.0782 (13)	0.0508 (10)	0.0656 (12)	−0.0200 (9)	−0.0277 (10)	0.0170 (9)
C13	0.0455 (8)	0.0448 (8)	0.0380 (7)	−0.0093 (6)	−0.0077 (6)	0.0158 (6)
C14	0.0451 (8)	0.0419 (8)	0.0399 (7)	−0.0003 (6)	−0.0031 (6)	0.0151 (6)
O14	0.0743 (8)	0.0476 (6)	0.0610 (7)	−0.0102 (6)	−0.0171 (6)	0.0277 (6)
C15	0.0427 (8)	0.0418 (7)	0.0372 (7)	0.0026 (6)	−0.0045 (6)	0.0138 (6)
C16	0.0481 (8)	0.0474 (8)	0.0352 (7)	0.0013 (6)	−0.0014 (6)	0.0143 (6)
C17	0.0519 (9)	0.0453 (8)	0.0493 (9)	−0.0038 (7)	−0.0004 (7)	0.0139 (7)
C18	0.0489 (9)	0.0468 (8)	0.0421 (8)	0.0039 (7)	−0.0068 (7)	0.0026 (6)
C19	0.0678 (11)	0.0646 (11)	0.0346 (8)	0.0020 (9)	−0.0050 (7)	0.0134 (7)
C20	0.0581 (10)	0.0571 (9)	0.0430 (8)	−0.0035 (8)	−0.0021 (7)	0.0224 (7)

Geometric parameters (Å, º)

Cl1—C18	1.7414 (16)	C9—C10	1.542 (3)
N1—C11	1.3747 (19)	C9—H9A	0.9700
N1—C2	1.399 (2)	C9—H9B	0.9700
N1—C13	1.4641 (17)	C10—C11	1.509 (2)
C2—O2	1.241 (2)	C10—H10A	0.9700
C2—C3	1.431 (2)	C10—H10B	0.9700
C3—C4	1.357 (2)	C12—H12A	0.9600
C3—H3	0.9300	C12—H12B	0.9600
C4—C5	1.426 (2)	C12—H12C	0.9600
C4—C12	1.509 (2)	C13—C14	1.5150 (19)
C5—C11	1.3730 (19)	C13—H13A	0.9700
C5—C6	1.507 (2)	C13—H13B	0.9700
C6—C7	1.538 (3)	C14—O14	1.2122 (18)
C6—H6A	0.9700	C14—C15	1.490 (2)
C6—H6B	0.9700	C15—C16	1.388 (2)
C7—C8B	1.485 (9)	C15—C20	1.391 (2)
C7—C8A	1.511 (5)	C16—C17	1.384 (2)
C7—H7A	0.9700	C16—H16	0.9300
C7—H7B	0.9700	C17—C18	1.379 (2)
C8A—C9	1.434 (4)	C17—H17	0.9300
C8A—H8A	0.9700	C18—C19	1.367 (3)
C8A—H8B	0.9700	C19—C20	1.382 (2)
C8B—C9	1.461 (8)	C19—H19	0.9300
C8B—H8C	0.9700	C20—H20	0.9300
C8B—H8D	0.9700
C11—N1—C2	122.99 (12)	C8A—C9—H9B	107.9
C11—N1—C13	121.37 (12)	C8B—C9—H9B	70.1
C2—N1—C13	115.56 (13)	C10—C9—H9B	107.9
O2—C2—N1	120.49 (14)	H9A—C9—H9B	107.2
O2—C2—C3	124.82 (15)	C11—C10—C9	114.24 (15)
N1—C2—C3	114.69 (14)	C11—C10—H10A	108.7
C4—C3—C2	123.28 (15)	C9—C10—H10A	108.7
C4—C3—H3	118.4	C11—C10—H10B	108.7
C2—C3—H3	118.4	C9—C10—H10B	108.7
C3—C4—C5	119.42 (13)	H10A—C10—H10B	107.6
C3—C4—C12	119.76 (16)	C5—C11—N1	120.98 (13)
C5—C4—C12	120.82 (16)	C5—C11—C10	119.17 (14)
C11—C5—C4	118.58 (14)	N1—C11—C10	119.85 (13)
C11—C5—C6	118.81 (15)	C4—C12—H12A	109.5
C4—C5—C6	122.58 (14)	C4—C12—H12B	109.5
C5—C6—C7	112.55 (15)	H12A—C12—H12B	109.5
C5—C6—H6A	109.1	C4—C12—H12C	109.5
C7—C6—H6A	109.1	H12A—C12—H12C	109.5
C5—C6—H6B	109.1	H12B—C12—H12C	109.5
C7—C6—H6B	109.1	N1—C13—C14	111.69 (12)
H6A—C6—H6B	107.8	N1—C13—H13A	109.3
C8B—C7—C6	113.0 (3)	C14—C13—H13A	109.3
C8A—C7—C6	114.07 (18)	N1—C13—H13B	109.3
C8B—C7—H7A	73.9	C14—C13—H13B	109.3
C8A—C7—H7A	108.7	H13A—C13—H13B	107.9
C6—C7—H7A	108.7	O14—C14—C15	121.28 (13)
C8B—C7—H7B	135.1	O14—C14—C13	120.76 (13)
C8A—C7—H7B	108.7	C15—C14—C13	117.95 (12)
C6—C7—H7B	108.7	C16—C15—C20	119.24 (14)
H7A—C7—H7B	107.6	C16—C15—C14	122.80 (13)
C9—C8A—C7	120.5 (4)	C20—C15—C14	117.96 (14)
C9—C8A—H8A	107.2	C17—C16—C15	120.11 (14)
C7—C8A—H8A	107.2	C17—C16—H16	119.9
C9—C8A—H8B	107.2	C15—C16—H16	119.9
C7—C8A—H8B	107.2	C18—C17—C16	119.08 (15)
H8A—C8A—H8B	106.8	C18—C17—H17	120.5
C9—C8B—C7	120.5 (7)	C16—C17—H17	120.5
C9—C8B—H8C	107.2	C19—C18—C17	122.00 (15)
C7—C8B—H8C	107.2	C19—C18—Cl1	118.96 (13)
C9—C8B—H8D	107.2	C17—C18—Cl1	119.04 (13)
C7—C8B—H8D	107.2	C18—C19—C20	118.72 (15)
H8C—C8B—H8D	106.8	C18—C19—H19	120.6
C8A—C9—C10	117.6 (2)	C20—C19—H19	120.6
C8B—C9—C10	120.8 (3)	C19—C20—C15	120.81 (16)
C8A—C9—H9A	107.9	C19—C20—H20	119.6
C8B—C9—H9A	129.9	C15—C20—H20	119.6
C10—C9—H9A	107.9