5-Benzoyl-1-n-butyl-4-phenyl­pyrimidin-2(1H)-one

The title compound, C₂₁H₂₀N₂O₂, crystallizes in the monoclinic space group P2₁/c. The pyrimidine ring is essentially planar. The structure is stabilized by intermolecular C—H...O interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.062
• wR factor = 0.197
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       5.29 Ratio
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.83 Ratio

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C7
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT432_ALERT_2_C Short Inter X...Y Contact  O2     ..  C4       =       3.00 Ang.

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PARST (Nardelli, 1995), WinGX publication routines (Farrugia, 1999).

5-benzoyl-1-n-butyl-4-phenylpyrimidin-2(1H)-one

Crystal data

C21H20N2O2	F(000) = 704
Mr = 332.39	Dx = 1.239 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 15 reflections
a = 10.125 (5) Å	θ = 25–35°
b = 15.518 (5) Å	µ = 0.08 mm^−1
c = 11.398 (5) Å	T = 293 K
β = 95.727 (5)°	Prism, white
V = 1781.9 (13) Å^3	0.42 × 0.42 × 0.33 mm
Z = 4

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.000
ω/2θ scans	θmax = 26.3°, θmin = 2.2°
Absorption correction: part of the refinement model (ΔF) (Parkin et al., 1995; cubic fit to sinθ/λ - 24 parameters)	h = −12→12
Tmin = 0.967, Tmax = 0.974	k = 0→19
3491 measured reflections	l = 0→14
3491 independent reflections	3 standard reflections every 120 min
1865 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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.197	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.1151P)^2] where P = (Fo^2 + 2Fc^2)/3
3491 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.47 e Å^−3
1 restraint	Δρmin = −0.42 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^{2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 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	1.1051 (2)	0.23118 (14)	0.29445 (16)	0.0623 (8)
O2	0.81816 (19)	−0.02863 (12)	0.57723 (16)	0.0512 (7)
N1	0.9329 (2)	0.14119 (15)	0.32296 (18)	0.0458 (7)
N2	1.0634 (2)	0.20715 (14)	0.48316 (19)	0.0496 (8)
C1	0.9989 (3)	0.16239 (18)	0.5597 (2)	0.0451 (9)
C2	0.9010 (2)	0.10559 (17)	0.5239 (2)	0.0408 (8)
C3	0.8677 (2)	0.09951 (17)	0.3988 (2)	0.0408 (8)
C4	1.0375 (3)	0.19363 (17)	0.3615 (2)	0.0448 (9)
C5	1.1691 (4)	0.2681 (2)	0.5252 (3)	0.0737 (13)
C6	1.3019 (5)	0.2285 (3)	0.5416 (5)	0.118 (2)
C7	1.3872 (5)	0.2998 (4)	0.6025 (6)	0.146 (3)
C8	1.5299 (6)	0.2676 (5)	0.6301 (10)	0.210 (5)
C9	0.8495 (2)	0.04417 (17)	0.6090 (2)	0.0397 (8)
C10	0.8382 (2)	0.07039 (18)	0.7331 (2)	0.0425 (9)
C11	0.8057 (3)	0.15306 (19)	0.7650 (2)	0.0524 (10)
C12	0.7866 (4)	0.1716 (2)	0.8811 (3)	0.0664 (11)
C13	0.8045 (3)	0.1087 (2)	0.9656 (3)	0.0684 (11)
C14	0.8402 (4)	0.0275 (2)	0.9350 (3)	0.0685 (13)
C15	0.8543 (3)	0.0073 (2)	0.8195 (2)	0.0540 (10)
C16	0.7505 (3)	0.05085 (19)	0.3469 (2)	0.0465 (9)
C17	0.6262 (3)	0.0615 (2)	0.3889 (3)	0.0586 (10)
C18	0.5168 (3)	0.0213 (3)	0.3331 (3)	0.0733 (13)
C19	0.5272 (4)	−0.0297 (3)	0.2380 (3)	0.0846 (14)
C20	0.6490 (4)	−0.0423 (3)	0.1968 (3)	0.0894 (16)
C21	0.7600 (3)	−0.0014 (2)	0.2504 (3)	0.0653 (13)
H1	1.02180	0.17030	0.64010	0.0540*
H5A	1.14870	0.29250	0.59960	0.0880*
H5B	1.17050	0.31490	0.46890	0.0880*
H6A	1.33290	0.21310	0.46660	0.1420*
H6B	1.30190	0.17740	0.59080	0.1420*
H7A	1.35130	0.31650	0.67500	0.1750*
H7B	1.38610	0.35000	0.55160	0.1750*
H8A	1.58350	0.31290	0.66730	0.3150*
H8B	1.56480	0.25090	0.55820	0.3150*
H8C	1.53070	0.21890	0.68210	0.3150*
H11	0.79660	0.19640	0.70830	0.0630*
H12	0.76160	0.22680	0.90170	0.0800*
H13	0.79240	0.12130	1.04350	0.0820*
H14	0.85520	−0.01450	0.99290	0.0820*
H15	0.87460	−0.04890	0.79920	0.0650*
H17	0.61780	0.09580	0.45460	0.0700*
H18	0.43440	0.02900	0.36100	0.0880*
H19	0.45210	−0.05610	0.20050	0.1010*
H20	0.65640	−0.07850	0.13280	0.1070*
H21	0.84170	−0.00920	0.22120	0.0780*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0672 (13)	0.0822 (16)	0.0398 (11)	−0.0131 (11)	0.0161 (9)	0.0134 (10)
O2	0.0627 (12)	0.0476 (12)	0.0437 (11)	−0.0065 (9)	0.0075 (9)	−0.0001 (9)
N1	0.0477 (12)	0.0586 (14)	0.0319 (11)	0.0037 (11)	0.0083 (9)	0.0042 (10)
N2	0.0656 (15)	0.0510 (13)	0.0338 (12)	−0.0110 (12)	0.0133 (10)	0.0017 (10)
C1	0.0545 (16)	0.0538 (16)	0.0281 (13)	−0.0030 (13)	0.0103 (11)	0.0018 (11)
C2	0.0460 (14)	0.0467 (14)	0.0309 (13)	0.0003 (12)	0.0094 (11)	0.0020 (11)
C3	0.0429 (14)	0.0477 (15)	0.0320 (13)	0.0072 (12)	0.0054 (11)	0.0015 (11)
C4	0.0525 (16)	0.0510 (16)	0.0322 (13)	0.0024 (13)	0.0107 (12)	0.0065 (11)
C5	0.102 (3)	0.079 (2)	0.0424 (16)	−0.052 (2)	0.0187 (17)	−0.0082 (16)
C6	0.080 (3)	0.157 (5)	0.111 (4)	−0.058 (3)	−0.022 (3)	0.017 (3)
C7	0.131 (5)	0.172 (5)	0.128 (5)	−0.058 (4)	−0.019 (4)	0.020 (4)
C8	0.125 (6)	0.178 (7)	0.311 (12)	−0.008 (5)	−0.054 (7)	−0.032 (8)
C9	0.0398 (13)	0.0475 (16)	0.0317 (13)	0.0006 (12)	0.0038 (10)	0.0043 (11)
C10	0.0416 (14)	0.0532 (17)	0.0338 (13)	−0.0040 (12)	0.0092 (11)	0.0046 (12)
C11	0.0652 (18)	0.0504 (17)	0.0440 (16)	−0.0103 (14)	0.0180 (13)	0.0010 (13)
C12	0.087 (2)	0.0576 (19)	0.060 (2)	−0.0161 (17)	0.0335 (17)	−0.0152 (16)
C13	0.089 (2)	0.083 (2)	0.0368 (16)	−0.021 (2)	0.0240 (16)	−0.0078 (16)
C14	0.083 (2)	0.086 (3)	0.0384 (16)	−0.0006 (19)	0.0156 (15)	0.0163 (16)
C15	0.0605 (17)	0.0632 (18)	0.0396 (15)	0.0034 (15)	0.0113 (13)	0.0080 (13)
C16	0.0478 (15)	0.0606 (17)	0.0310 (13)	0.0016 (13)	0.0038 (11)	0.0044 (12)
C17	0.0500 (17)	0.076 (2)	0.0506 (17)	0.0054 (15)	0.0089 (14)	0.0013 (15)
C18	0.0474 (18)	0.109 (3)	0.064 (2)	−0.0078 (18)	0.0077 (16)	0.008 (2)
C19	0.065 (2)	0.122 (3)	0.065 (2)	−0.032 (2)	−0.0026 (18)	0.001 (2)
C20	0.084 (3)	0.128 (3)	0.057 (2)	−0.032 (2)	0.0110 (19)	−0.033 (2)
C21	0.0588 (18)	0.096 (3)	0.0428 (16)	−0.0180 (18)	0.0133 (14)	−0.0142 (16)

Geometric parameters (Å, º)

O1—C4	1.223 (3)	C18—C19	1.355 (6)
O2—C9	1.219 (3)	C19—C20	1.377 (6)
N1—C3	1.310 (3)	C20—C21	1.379 (5)
N1—C4	1.373 (4)	C1—H1	0.9307
N2—C1	1.336 (3)	C5—H5A	0.9696
N2—C4	1.401 (3)	C5—H5B	0.9702
N2—C5	1.472 (4)	C6—H6A	0.9695
C1—C2	1.358 (4)	C6—H6B	0.9712
C2—C3	1.435 (3)	C7—H7A	0.9706
C2—C9	1.491 (3)	C7—H7B	0.9707
C3—C16	1.479 (4)	C8—H8A	0.9605
C5—C6	1.473 (6)	C8—H8B	0.9599
C6—C7	1.527 (8)	C8—H8C	0.9600
C7—C8	1.532 (9)	C11—H11	0.9309
C9—C10	1.487 (3)	C12—H12	0.9300
C10—C11	1.382 (4)	C13—H13	0.9292
C10—C15	1.387 (4)	C14—H14	0.9292
C11—C12	1.387 (4)	C15—H15	0.9305
C12—C13	1.371 (5)	C17—H17	0.9295
C13—C14	1.366 (5)	C18—H18	0.9297
C14—C15	1.375 (4)	C19—H19	0.9294
C16—C17	1.400 (4)	C20—H20	0.9296
C16—C21	1.378 (4)	C21—H21	0.9299
C17—C18	1.371 (5)
O1···C6	3.284 (6)	C3···H12^i	2.9029
O1···C5^i	3.199 (4)	C4···H15^ii	3.0849
O1···C1^i	3.236 (4)	C8···H11^v	2.9710
O2···C1^ii	3.279 (4)	C9···H17	2.9015
O2···C17	3.084 (4)	C10···H1	2.7159
O2···C4^ii	2.996 (4)	C11···H1	2.7399
O2···C2^ii	3.390 (3)	C11···H8C^vi	3.0273
O2···C16	2.920 (3)	C11···H19^iii	3.0719
O2···N2^ii	3.123 (3)	C12···H19^iii	3.0773
O2···N1^ii	3.182 (3)	C21···H13^viii	3.0739
O2···C3^ii	3.351 (3)	H1···C10	2.7159
O1···H1^i	2.4182	H1···C11	2.7399
O1···H5B	2.4119	H1···H5A	2.3618
O1···H5A^i	2.3362	H1···H11	2.5142
O1···H6A	2.8888	H1···O1^iv	2.4182
O2···H15	2.5569	H5A···H1	2.3618
O2···H18^iii	2.7192	H5A···H7A	2.1756
N1···C12^i	3.357 (4)	H5A···O1^iv	2.3362
N1···O2^ii	3.182 (3)	H5B···O1	2.4119
N2···O2^ii	3.123 (3)	H5B···H7B	2.3537
N1···H21	2.7259	H6A···O1	2.8888
N1···H12^i	2.8846	H6A···H8B	2.5412
N1···H15^ii	2.8862	H6B···C1	3.0618
C1···C11	3.200 (4)	H6B···H8C	2.5265
C1···O1^iv	3.236 (4)	H7A···H5A	2.1756
C1···O2^ii	3.279 (4)	H7B···H5B	2.3537
C2···O2^ii	3.390 (3)	H7B···H20^ix	2.3777
C3···O2^ii	3.351 (3)	H8B···H6A	2.5412
C4···C11^i	3.444 (4)	H8C···C11^v	3.0273
C4···C12^i	3.315 (5)	H8C···H6B	2.5265
C4···O2^ii	2.996 (4)	H11···C1	2.8346
C5···O1^iv	3.199 (4)	H11···C2	2.8221
C6···O1	3.284 (6)	H11···C8^vi	2.9710
C8···C11^v	3.531 (8)	H11···H1	2.5142
C9···C17	3.217 (4)	H12···N1^iv	2.8846
C11···C4^iv	3.444 (4)	H12···C3^iv	2.9029
C11···C1	3.200 (4)	H13···C21^x	3.0739
C11···C8^vi	3.531 (8)	H15···O2	2.5569
C12···C4^iv	3.315 (5)	H15···N1^ii	2.8862
C12···N1^iv	3.357 (4)	H15···C4^ii	3.0849
C14···C14^vii	3.527 (6)	H17···C2	2.9012
C16···O2	2.920 (3)	H17···C9	2.9015
C17···C9	3.217 (4)	H18···O2^iii	2.7192
C17···O2	3.084 (4)	H19···C11^iii	3.0719
C1···H11	2.8346	H19···C12^iii	3.0773
C1···H6B	3.0618	H20···H7B^xi	2.3777
C2···H11	2.8221	H21···N1	2.7259
C2···H17	2.9012
C3—N1—C4	120.4 (2)	C6—C5—H5A	108.86
C1—N2—C4	120.9 (2)	C6—C5—H5B	108.83
C1—N2—C5	120.6 (2)	H5A—C5—H5B	107.74
C4—N2—C5	118.5 (2)	C5—C6—H6A	111.26
N2—C1—C2	122.1 (2)	C5—C6—H6B	111.18
C1—C2—C3	115.7 (2)	C7—C6—H6A	111.17
C1—C2—C9	120.8 (2)	C7—C6—H6B	111.20
C3—C2—C9	122.8 (2)	H6A—C6—H6B	109.06
N1—C3—C2	122.6 (2)	C6—C7—H7A	109.73
N1—C3—C16	115.2 (2)	C6—C7—H7B	109.73
C2—C3—C16	122.0 (2)	C8—C7—H7A	109.76
O1—C4—N1	123.0 (2)	C8—C7—H7B	109.81
O1—C4—N2	119.1 (2)	H7A—C7—H7B	108.16
N1—C4—N2	117.9 (2)	C7—C8—H8A	109.38
N2—C5—C6	113.5 (3)	C7—C8—H8B	109.44
C5—C6—C7	102.9 (4)	C7—C8—H8C	109.47
C6—C7—C8	109.6 (5)	H8A—C8—H8B	109.55
O2—C9—C2	119.8 (2)	H8A—C8—H8C	109.51
O2—C9—C10	119.6 (2)	H8B—C8—H8C	109.48
C2—C9—C10	120.6 (2)	C10—C11—H11	119.84
C9—C10—C11	123.2 (2)	C12—C11—H11	119.94
C9—C10—C15	117.9 (2)	C11—C12—H12	119.97
C11—C10—C15	118.9 (2)	C13—C12—H12	119.92
C10—C11—C12	120.2 (2)	C12—C13—H13	120.06
C11—C12—C13	120.1 (3)	C14—C13—H13	120.11
C12—C13—C14	119.8 (3)	C13—C14—H14	119.63
C13—C14—C15	120.7 (3)	C15—C14—H14	119.67
C10—C15—C14	120.2 (3)	C10—C15—H15	119.89
C3—C16—C17	121.0 (2)	C14—C15—H15	119.90
C3—C16—C21	120.2 (3)	C16—C17—H17	120.04
C17—C16—C21	118.6 (3)	C18—C17—H17	119.97
C16—C17—C18	120.0 (3)	C17—C18—H18	119.59
C17—C18—C19	120.9 (3)	C19—C18—H18	119.53
C18—C19—C20	120.0 (4)	C18—C19—H19	120.01
C19—C20—C21	120.1 (4)	C20—C19—H19	120.01
C16—C21—C20	120.4 (3)	C19—C20—H20	119.91
N2—C1—H1	118.98	C21—C20—H20	119.98
C2—C1—H1	118.95	C16—C21—H21	119.86
N2—C5—H5A	108.92	C20—C21—H21	119.75
N2—C5—H5B	108.89
C3—N1—C4—O1	176.9 (3)	C2—C3—C16—C17	47.5 (4)
C3—N1—C4—N2	−5.9 (4)	C2—C3—C16—C21	−137.1 (3)
C4—N1—C3—C2	−0.3 (4)	N2—C5—C6—C7	−171.5 (4)
C4—N1—C3—C16	175.2 (2)	C5—C6—C7—C8	178.1 (6)
C5—N2—C1—C2	−179.9 (3)	O2—C9—C10—C15	30.0 (3)
C1—N2—C5—C6	89.8 (4)	C2—C9—C10—C15	−148.9 (2)
C4—N2—C1—C2	−3.6 (4)	O2—C9—C10—C11	−146.5 (3)
C1—N2—C4—N1	8.0 (4)	C2—C9—C10—C11	34.6 (3)
C5—N2—C4—N1	−175.7 (2)	C9—C10—C11—C12	174.9 (3)
C1—N2—C4—O1	−174.8 (3)	C11—C10—C15—C14	−1.1 (4)
C4—N2—C5—C6	−86.6 (4)	C9—C10—C15—C14	−177.7 (3)
C5—N2—C4—O1	1.6 (4)	C15—C10—C11—C12	−1.5 (4)
N2—C1—C2—C9	167.8 (2)	C10—C11—C12—C13	2.3 (5)
N2—C1—C2—C3	−2.5 (4)	C11—C12—C13—C14	−0.5 (5)
C9—C2—C3—N1	−165.5 (2)	C12—C13—C14—C15	−2.1 (5)
C1—C2—C3—C16	−170.6 (3)	C13—C14—C15—C10	2.9 (5)
C3—C2—C9—C10	−154.8 (2)	C17—C16—C21—C20	−0.1 (5)
C9—C2—C3—C16	19.4 (4)	C21—C16—C17—C18	−0.9 (5)
C1—C2—C3—N1	4.6 (4)	C3—C16—C21—C20	−175.6 (3)
C1—C2—C9—O2	−143.2 (3)	C3—C16—C17—C18	174.5 (3)
C3—C2—C9—O2	26.3 (3)	C16—C17—C18—C19	0.7 (6)
C1—C2—C9—C10	35.7 (3)	C17—C18—C19—C20	0.6 (6)
N1—C3—C16—C17	−128.0 (3)	C18—C19—C20—C21	−1.6 (6)
N1—C3—C16—C21	47.4 (4)	C19—C20—C21—C16	1.4 (6)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+2, −y, −z+1; (iii) −x+1, −y, −z+1; (iv) x, −y+1/2, z+1/2; (v) x+1, y, z; (vi) x−1, y, z; (vii) −x+2, −y, −z+2; (viii) x, y, z−1; (ix) −x+2, y+1/2, −z+1/2; (x) x, y, z+1; (xi) −x+2, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1^iv	0.93	2.42	3.236 (4)	147
C5—H5A···O1^iv	0.97	2.34	3.199 (4)	148

Symmetry code: (iv) x, −y+1/2, z+1/2.