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The title compound, C12H9ClN2O2, was synthesized and characterized by 1H NMR and IR spectrocopy and X-ray diffraction techniques. The chlorobenzoyl fragment in the structure is almost flat, whereas the carbonyl group is almost perpendicular to the pyrimidine ring plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806018927/bd2004sup1.cif
Contains datablocks global, 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806018927/bd20042sup2.hkl
Contains datablock 2

CCDC reference: 610689

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.054
  • wR factor = 0.161
  • Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.96
Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT431_ALERT_2_C Short Inter HL..A Contact Cl12 .. O2 .. 3.09 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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-Chlorobenzoylmethyl)pyrimidin-2(1H)-one top
Crystal data top
C12H9ClN2O2F(000) = 512
Mr = 248.66Dx = 1.451 Mg m3
Monoclinic, P21/nMelting point: 498 K
Hall symbol: -P 2ynCu Kα radiation, λ = 1.5418 Å
a = 10.2191 (10) ÅCell parameters from 25 reflections
b = 10.8421 (14) Åθ = 33–35°
c = 11.3449 (15) ŵ = 2.91 mm1
β = 115.065 (11)°T = 293 K
V = 1138.6 (3) Å3Prism, colourless
Z = 40.2 × 0.2 × 0.2 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.000
Radiation source: Fine-focus sealed tubeθmax = 77.9°, θmin = 4.9°
Graphite monochromatorh = 1211
Non–profiled ω scansk = 013
2327 measured reflectionsl = 013
2327 independent reflections1 standard reflections every 120 min
1842 reflections with I > 2σ(I) intensity decay: 5%
Refinement top
Refinement on F2Secondary atom site location: Difmap
Least-squares matrix: FullHydrogen site location: Geom
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.161 w = 1/[σ2(Fo2) + (0.0895P)2 + 0.2167P]
where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max = 0.002
2327 reflectionsΔρmax = 0.71 e Å3
155 parametersΔρmin = 0.79 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: DirectExtinction coefficient: 0.0192 (19)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.2904 (2)0.37560 (16)0.77954 (18)0.0430 (4)
C20.3699 (2)0.26588 (19)0.8057 (2)0.0438 (5)
O20.3793 (2)0.20882 (16)0.71627 (18)0.0591 (5)
N30.4332 (2)0.22667 (18)0.9317 (2)0.0528 (5)
C40.4215 (3)0.2938 (2)1.0225 (2)0.0537 (6)
H40.46570.26511.10770.064*
C50.3468 (3)0.4056 (2)1.0000 (3)0.0561 (6)
H50.34210.45121.06750.067*
C60.2823 (3)0.4438 (2)0.8761 (2)0.0505 (5)
H60.23160.51790.85630.061*
C70.2248 (3)0.4192 (2)0.6457 (2)0.0497 (5)
H7A0.13500.46120.62960.060*
H7B0.20220.34910.58720.060*
C80.3233 (3)0.5064 (2)0.6169 (2)0.0491 (5)
O80.4288 (2)0.5484 (2)0.7062 (2)0.0833 (7)
C90.2844 (2)0.5409 (2)0.4802 (2)0.0450 (5)
C100.1670 (3)0.4899 (2)0.3757 (2)0.0481 (5)
H100.11020.43040.39080.058*
C110.1345 (3)0.5273 (2)0.2499 (2)0.0525 (6)
H110.05690.49270.18020.063*
C120.2183 (3)0.6165 (2)0.2287 (2)0.0501 (6)
Cl120.17713 (8)0.66364 (6)0.07015 (6)0.0651 (3)
C130.3355 (3)0.6685 (2)0.3306 (3)0.0594 (6)
H130.39170.72800.31490.071*
C140.3673 (3)0.6306 (3)0.4551 (3)0.0581 (6)
H140.44570.66530.52410.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0480 (9)0.0370 (9)0.0399 (10)0.0015 (7)0.0147 (7)0.0036 (7)
C20.0498 (11)0.0355 (10)0.0456 (12)0.0036 (8)0.0197 (9)0.0020 (8)
O20.0771 (12)0.0512 (9)0.0524 (10)0.0010 (8)0.0306 (9)0.0115 (8)
N30.0670 (12)0.0429 (10)0.0458 (11)0.0121 (9)0.0213 (9)0.0042 (8)
C40.0644 (13)0.0518 (12)0.0398 (12)0.0092 (11)0.0171 (10)0.0066 (10)
C50.0726 (15)0.0477 (12)0.0506 (13)0.0093 (11)0.0285 (12)0.0041 (10)
C60.0607 (13)0.0387 (10)0.0506 (13)0.0070 (9)0.0222 (11)0.0004 (9)
C70.0532 (12)0.0506 (12)0.0384 (11)0.0051 (10)0.0127 (9)0.0084 (9)
C80.0514 (11)0.0467 (12)0.0455 (12)0.0069 (9)0.0169 (10)0.0001 (9)
O80.0814 (13)0.1050 (17)0.0464 (11)0.0469 (13)0.0105 (9)0.0014 (11)
C90.0476 (11)0.0426 (11)0.0433 (12)0.0031 (9)0.0178 (9)0.0020 (9)
C100.0536 (12)0.0424 (11)0.0446 (12)0.0047 (9)0.0174 (10)0.0005 (9)
C110.0597 (13)0.0507 (12)0.0412 (12)0.0019 (10)0.0157 (10)0.0006 (9)
C120.0627 (14)0.0450 (11)0.0484 (13)0.0130 (10)0.0291 (11)0.0081 (9)
Cl120.0907 (5)0.0601 (4)0.0516 (4)0.0205 (3)0.0371 (3)0.0163 (3)
C130.0664 (15)0.0572 (14)0.0604 (16)0.0082 (11)0.0326 (13)0.0072 (12)
C140.0567 (13)0.0609 (14)0.0534 (14)0.0148 (11)0.0203 (11)0.0016 (11)
Geometric parameters (Å, º) top
N1—C61.353 (3)C8—O81.213 (3)
N1—C21.399 (3)C8—C91.477 (3)
N1—C71.455 (3)C9—C101.395 (3)
C2—O21.226 (3)C9—C141.396 (3)
C2—N31.364 (3)C10—C111.382 (3)
N3—C41.307 (3)C10—H100.9300
C4—C51.397 (3)C11—C121.379 (3)
C4—H40.9300C11—H110.9300
C5—C61.341 (4)C12—C131.384 (4)
C5—H50.9300C12—Cl121.742 (2)
C6—H60.9300C13—C141.371 (4)
C7—C81.514 (3)C13—H130.9300
C7—H7A0.9700C14—H140.9300
C7—H7B0.9700
C6—N1—C2121.49 (19)O8—C8—C9122.0 (2)
C6—N1—C7120.52 (19)O8—C8—C7119.5 (2)
C2—N1—C7117.84 (19)C9—C8—C7118.47 (19)
O2—C2—N3122.8 (2)C10—C9—C14118.8 (2)
O2—C2—N1119.7 (2)C10—C9—C8122.9 (2)
N3—C2—N1117.53 (19)C14—C9—C8118.3 (2)
C4—N3—C2119.42 (19)C11—C10—C9120.3 (2)
N3—C4—C5124.3 (2)C11—C10—H10119.9
N3—C4—H4117.8C9—C10—H10119.9
C5—C4—H4117.8C12—C11—C10119.4 (2)
C6—C5—C4116.6 (2)C12—C11—H11120.3
C6—C5—H5121.7C10—C11—H11120.3
C4—C5—H5121.7C11—C12—C13121.4 (2)
C5—C6—N1120.5 (2)C11—C12—Cl12119.3 (2)
C5—C6—H6119.7C13—C12—Cl12119.22 (19)
N1—C6—H6119.7C14—C13—C12118.8 (2)
N1—C7—C8111.92 (19)C14—C13—H13120.6
N1—C7—H7A109.2C12—C13—H13120.6
C8—C7—H7A109.2C13—C14—C9121.3 (2)
N1—C7—H7B109.2C13—C14—H14119.4
C8—C7—H7B109.2C9—C14—H14119.4
H7A—C7—H7B107.9
 

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