1-[(4-Chloro­benzo­yl)meth­yl]-4,6-dimethyl-2(1H)-pyrimidone

In the title mol­ecule, C₁₄H₁₃ClN₂O₂, all bond lengths and angles show normal values. The mean planes of the heterocyclic ring and the carbonyl group make a dihedral angle of 81.38 (5)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.086
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 EXPRESS; cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wokadlo, (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-Chlorobenzoyl)methyl]-4,6-dimethyl-2(1H)-pyrimidone

Crystal data

C14H13ClN2O2	F(000) = 576
Mr = 276.71	Dx = 1.403 Mg m^−3
Monoclinic, P21/n	Melting point: 446 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.5418 Å
a = 7.1975 (8) Å	Cell parameters from 25 reflections
b = 9.3817 (10) Å	θ = 30–33°
c = 19.422 (3) Å	µ = 2.58 mm^−1
β = 92.314 (9)°	T = 293 K
V = 1310.4 (3) Å^3	Prism, colourless
Z = 4	0.2 × 0.2 × 0.2 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.090
Radiation source: Fine-focus sealed tube	θmax = 74.9°, θmin = 4.6°
Graphite monochromator	h = −9→9
ω scans	k = 0→11
2760 measured reflections	l = 0→24
2683 independent reflections	1 standard reflections every 60 min
1907 reflections with I > 2σ(I)	intensity decay: 4%

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.086	H-atom parameters constrained
S = 0.96	w = 1/[σ^2(Fo^2) + (0.0422P)^2] where P = (Fo^2 + 2Fc^2)/3
2683 reflections	(Δ/σ)max = 0.003
174 parameters	Δρmax = 0.12 e Å^−3
0 restraints	Δρmin = −0.14 e Å^−3

Special details

Experimental. Spectroscopic analysis: ¹H NMR (DMSO-d₆/TMS, δ, J, Hz): 2.24 (3H, s, CH₃), 2.29 (3H, s, CH₃), 5.50 (2H, s, CH₂), 6.23 (1H, s, H-5), 7.56 (2H, m, p-ClPh), 8.08 (2H, m, p-ClPh); IR (nujol, ν_CO, cm^-1): 1695, 1610.

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

	x	y	z	Uiso*/Ueq
N1	0.06506 (16)	0.44796 (13)	0.72057 (6)	0.0447 (3)
C2	0.0976 (2)	0.54726 (17)	0.66780 (8)	0.0525 (4)
O2	0.24693 (18)	0.60918 (14)	0.66857 (7)	0.0749 (4)
N3	−0.0403 (2)	0.57024 (15)	0.61881 (7)	0.0588 (4)
C4	−0.1962 (2)	0.49939 (18)	0.62188 (8)	0.0543 (4)
C41	−0.3433 (3)	0.5293 (3)	0.56670 (10)	0.0871 (7)
H41A	−0.3350	0.6270	0.5525	0.131*
H41B	−0.4638	0.5118	0.5844	0.131*
H41C	−0.3251	0.4681	0.5279	0.131*
C5	−0.2315 (2)	0.39954 (17)	0.67347 (9)	0.0544 (4)
H5	−0.3440	0.3508	0.6734	0.065*
C6	−0.0981 (2)	0.37535 (16)	0.72360 (8)	0.0460 (3)
C61	−0.1249 (2)	0.2720 (2)	0.78081 (10)	0.0645 (5)
H61A	−0.2454	0.2289	0.7752	0.097*
H61B	−0.1155	0.3213	0.8241	0.097*
H61C	−0.0309	0.1995	0.7798	0.097*
C7	0.2147 (2)	0.43830 (17)	0.77377 (8)	0.0505 (4)
H7A	0.3338	0.4357	0.7522	0.061*
H7B	0.2015	0.3507	0.7997	0.061*
C8	0.2092 (2)	0.56504 (18)	0.82245 (8)	0.0494 (4)
O8	0.07713 (17)	0.64427 (14)	0.82093 (7)	0.0755 (4)
C9	0.3723 (2)	0.58649 (16)	0.87126 (7)	0.0460 (3)
C10	0.5266 (2)	0.5011 (2)	0.87179 (9)	0.0658 (5)
H10	0.5316	0.4254	0.8410	0.079*
C11	0.6757 (2)	0.5261 (2)	0.91776 (10)	0.0695 (5)
H11	0.7813	0.4691	0.9172	0.083*
C12	0.6654 (2)	0.63622 (19)	0.96415 (8)	0.0537 (4)
C13	0.5112 (2)	0.7211 (2)	0.96540 (9)	0.0614 (4)
H13	0.5053	0.7948	0.9973	0.074*
C14	0.3639 (2)	0.69656 (19)	0.91894 (8)	0.0564 (4)
H14	0.2587	0.7540	0.9196	0.068*
Cl12	0.85163 (7)	0.66768 (6)	1.02110 (3)	0.07873 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0469 (6)	0.0388 (7)	0.0486 (7)	−0.0027 (5)	0.0044 (5)	−0.0018 (6)
C2	0.0634 (9)	0.0423 (9)	0.0522 (9)	−0.0095 (7)	0.0072 (7)	0.0009 (7)
O2	0.0757 (8)	0.0680 (9)	0.0809 (9)	−0.0302 (7)	0.0020 (7)	0.0097 (7)
N3	0.0728 (9)	0.0489 (8)	0.0543 (8)	−0.0026 (7)	−0.0019 (7)	0.0066 (7)
C4	0.0579 (9)	0.0507 (10)	0.0543 (9)	0.0038 (7)	0.0026 (7)	−0.0080 (8)
C41	0.0881 (14)	0.0882 (16)	0.0823 (14)	0.0122 (12)	−0.0283 (11)	−0.0002 (12)
C5	0.0475 (8)	0.0431 (9)	0.0728 (11)	−0.0042 (7)	0.0049 (7)	−0.0064 (8)
C6	0.0491 (7)	0.0355 (8)	0.0541 (8)	0.0028 (6)	0.0131 (6)	−0.0029 (7)
C61	0.0659 (10)	0.0556 (11)	0.0739 (11)	0.0052 (8)	0.0272 (9)	0.0151 (9)
C7	0.0498 (8)	0.0477 (9)	0.0539 (8)	0.0047 (7)	0.0003 (7)	−0.0031 (7)
C8	0.0525 (8)	0.0486 (9)	0.0476 (8)	0.0068 (7)	0.0088 (6)	−0.0011 (7)
O8	0.0681 (7)	0.0770 (9)	0.0804 (9)	0.0294 (7)	−0.0095 (6)	−0.0245 (7)
C9	0.0495 (8)	0.0446 (9)	0.0446 (7)	0.0004 (6)	0.0097 (6)	0.0003 (7)
C10	0.0693 (10)	0.0624 (12)	0.0649 (10)	0.0143 (9)	−0.0078 (9)	−0.0171 (9)
C11	0.0619 (10)	0.0684 (12)	0.0772 (12)	0.0162 (9)	−0.0076 (9)	−0.0169 (10)
C12	0.0555 (8)	0.0581 (11)	0.0481 (8)	−0.0089 (8)	0.0075 (7)	0.0014 (7)
C13	0.0679 (10)	0.0607 (11)	0.0562 (9)	−0.0067 (9)	0.0110 (8)	−0.0112 (9)
C14	0.0587 (9)	0.0547 (11)	0.0564 (9)	0.0036 (8)	0.0092 (7)	−0.0136 (8)
Cl12	0.0758 (3)	0.0869 (4)	0.0721 (3)	−0.0159 (3)	−0.0137 (2)	−0.0039 (3)

Geometric parameters (Å, º)

N1—C6	1.3607 (18)	C7—C8	1.521 (2)
N1—C2	1.4116 (19)	C7—H7A	0.9700
N1—C7	1.4648 (16)	C7—H7B	0.9700
C2—O2	1.2210 (18)	C8—O8	1.2061 (18)
C2—N3	1.3645 (18)	C8—C9	1.4924 (18)
N3—C4	1.307 (2)	C9—C10	1.370 (2)
C4—C5	1.402 (2)	C9—C14	1.390 (2)
C4—C41	1.502 (2)	C10—C11	1.388 (2)
C41—H41A	0.9600	C10—H10	0.9300
C41—H41B	0.9600	C11—C12	1.374 (2)
C41—H41C	0.9600	C11—H11	0.9300
C5—C6	1.3586 (19)	C12—C13	1.367 (2)
C5—H5	0.9300	C12—Cl12	1.7284 (15)
C6—C61	1.493 (2)	C13—C14	1.383 (2)
C61—H61A	0.9600	C13—H13	0.9300
C61—H61B	0.9600	C14—H14	0.9300
C61—H61C	0.9600
C6—N1—C2	122.06 (12)	N1—C7—C8	110.70 (12)
C6—N1—C7	123.33 (13)	N1—C7—H7A	109.5
C2—N1—C7	114.45 (12)	C8—C7—H7A	109.5
O2—C2—N3	123.27 (16)	N1—C7—H7B	109.5
O2—C2—N1	118.50 (14)	C8—C7—H7B	109.5
N3—C2—N1	118.23 (14)	H7A—C7—H7B	108.1
C4—N3—C2	119.31 (15)	O8—C8—C9	122.09 (15)
N3—C4—C5	123.56 (14)	O8—C8—C7	120.45 (14)
N3—C4—C41	116.99 (17)	C9—C8—C7	117.45 (13)
C5—C4—C41	119.45 (16)	C10—C9—C14	119.13 (14)
C4—C41—H41A	109.5	C10—C9—C8	122.87 (14)
C4—C41—H41B	109.5	C14—C9—C8	117.98 (13)
H41A—C41—H41B	109.5	C9—C10—C11	120.76 (17)
C4—C41—H41C	109.5	C9—C10—H10	119.6
H41A—C41—H41C	109.5	C11—C10—H10	119.6
H41B—C41—H41C	109.5	C12—C11—C10	119.22 (17)
C6—C5—C4	118.71 (15)	C12—C11—H11	120.4
C6—C5—H5	120.6	C10—C11—H11	120.4
C4—C5—H5	120.6	C13—C12—C11	120.97 (14)
C5—C6—N1	118.13 (15)	C13—C12—Cl12	119.89 (13)
C5—C6—C61	122.21 (15)	C11—C12—Cl12	119.14 (13)
N1—C6—C61	119.66 (13)	C12—C13—C14	119.53 (16)
C6—C61—H61A	109.5	C12—C13—H13	120.2
C6—C61—H61B	109.5	C14—C13—H13	120.2
H61A—C61—H61B	109.5	C13—C14—C9	120.36 (16)
C6—C61—H61C	109.5	C13—C14—H14	119.8
H61A—C61—H61C	109.5	C9—C14—H14	119.8
H61B—C61—H61C	109.5