organic compounds
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
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806018927/bd2004sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806018927/bd20042sup2.hkl |
CCDC reference: 610689
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
C12H9ClN2O2 | F(000) = 512 |
Mr = 248.66 | Dx = 1.451 Mg m−3 |
Monoclinic, P21/n | Melting point: 498 K |
Hall symbol: -P 2yn | Cu Kα radiation, λ = 1.5418 Å |
a = 10.2191 (10) Å | Cell parameters from 25 reflections |
b = 10.8421 (14) Å | θ = 33–35° |
c = 11.3449 (15) Å | µ = 2.91 mm−1 |
β = 115.065 (11)° | T = 293 K |
V = 1138.6 (3) Å3 | Prism, colourless |
Z = 4 | 0.2 × 0.2 × 0.2 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.000 |
Radiation source: Fine-focus sealed tube | θmax = 77.9°, θmin = 4.9° |
Graphite monochromator | h = −12→11 |
Non–profiled ω scans | k = 0→13 |
2327 measured reflections | l = 0→13 |
2327 independent reflections | 1 standard reflections every 120 min |
1842 reflections with I > 2σ(I) | intensity decay: 5% |
Refinement top
Refinement on F2 | Secondary atom site location: Difmap |
Least-squares matrix: Full | Hydrogen site location: Geom |
R[F2 > 2σ(F2)] = 0.054 | H-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 reflections | Δρmax = 0.71 e Å−3 |
155 parameters | Δρmin = −0.79 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: Direct | Extinction coefficient: 0.0192 (19) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
N1 | 0.2904 (2) | 0.37560 (16) | 0.77954 (18) | 0.0430 (4) | |
C2 | 0.3699 (2) | 0.26588 (19) | 0.8057 (2) | 0.0438 (5) | |
O2 | 0.3793 (2) | 0.20882 (16) | 0.71627 (18) | 0.0591 (5) | |
N3 | 0.4332 (2) | 0.22667 (18) | 0.9317 (2) | 0.0528 (5) | |
C4 | 0.4215 (3) | 0.2938 (2) | 1.0225 (2) | 0.0537 (6) | |
H4 | 0.4657 | 0.2651 | 1.1077 | 0.064* | |
C5 | 0.3468 (3) | 0.4056 (2) | 1.0000 (3) | 0.0561 (6) | |
H5 | 0.3421 | 0.4512 | 1.0675 | 0.067* | |
C6 | 0.2823 (3) | 0.4438 (2) | 0.8761 (2) | 0.0505 (5) | |
H6 | 0.2316 | 0.5179 | 0.8563 | 0.061* | |
C7 | 0.2248 (3) | 0.4192 (2) | 0.6457 (2) | 0.0497 (5) | |
H7A | 0.1350 | 0.4612 | 0.6296 | 0.060* | |
H7B | 0.2022 | 0.3491 | 0.5872 | 0.060* | |
C8 | 0.3233 (3) | 0.5064 (2) | 0.6169 (2) | 0.0491 (5) | |
O8 | 0.4288 (2) | 0.5484 (2) | 0.7062 (2) | 0.0833 (7) | |
C9 | 0.2844 (2) | 0.5409 (2) | 0.4802 (2) | 0.0450 (5) | |
C10 | 0.1670 (3) | 0.4899 (2) | 0.3757 (2) | 0.0481 (5) | |
H10 | 0.1102 | 0.4304 | 0.3908 | 0.058* | |
C11 | 0.1345 (3) | 0.5273 (2) | 0.2499 (2) | 0.0525 (6) | |
H11 | 0.0569 | 0.4927 | 0.1802 | 0.063* | |
C12 | 0.2183 (3) | 0.6165 (2) | 0.2287 (2) | 0.0501 (6) | |
Cl12 | 0.17713 (8) | 0.66364 (6) | 0.07015 (6) | 0.0651 (3) | |
C13 | 0.3355 (3) | 0.6685 (2) | 0.3306 (3) | 0.0594 (6) | |
H13 | 0.3917 | 0.7280 | 0.3149 | 0.071* | |
C14 | 0.3673 (3) | 0.6306 (3) | 0.4551 (3) | 0.0581 (6) | |
H14 | 0.4457 | 0.6653 | 0.5241 | 0.070* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0480 (9) | 0.0370 (9) | 0.0399 (10) | −0.0015 (7) | 0.0147 (7) | 0.0036 (7) |
C2 | 0.0498 (11) | 0.0355 (10) | 0.0456 (12) | −0.0036 (8) | 0.0197 (9) | −0.0020 (8) |
O2 | 0.0771 (12) | 0.0512 (9) | 0.0524 (10) | −0.0010 (8) | 0.0306 (9) | −0.0115 (8) |
N3 | 0.0670 (12) | 0.0429 (10) | 0.0458 (11) | 0.0121 (9) | 0.0213 (9) | 0.0042 (8) |
C4 | 0.0644 (13) | 0.0518 (12) | 0.0398 (12) | 0.0092 (11) | 0.0171 (10) | 0.0066 (10) |
C5 | 0.0726 (15) | 0.0477 (12) | 0.0506 (13) | 0.0093 (11) | 0.0285 (12) | −0.0041 (10) |
C6 | 0.0607 (13) | 0.0387 (10) | 0.0506 (13) | 0.0070 (9) | 0.0222 (11) | 0.0004 (9) |
C7 | 0.0532 (12) | 0.0506 (12) | 0.0384 (11) | −0.0051 (10) | 0.0127 (9) | 0.0084 (9) |
C8 | 0.0514 (11) | 0.0467 (12) | 0.0455 (12) | −0.0069 (9) | 0.0169 (10) | −0.0001 (9) |
O8 | 0.0814 (13) | 0.1050 (17) | 0.0464 (11) | −0.0469 (13) | 0.0105 (9) | 0.0014 (11) |
C9 | 0.0476 (11) | 0.0426 (11) | 0.0433 (12) | −0.0031 (9) | 0.0178 (9) | 0.0020 (9) |
C10 | 0.0536 (12) | 0.0424 (11) | 0.0446 (12) | −0.0047 (9) | 0.0174 (10) | 0.0005 (9) |
C11 | 0.0597 (13) | 0.0507 (12) | 0.0412 (12) | −0.0019 (10) | 0.0157 (10) | 0.0006 (9) |
C12 | 0.0627 (14) | 0.0450 (11) | 0.0484 (13) | 0.0130 (10) | 0.0291 (11) | 0.0081 (9) |
Cl12 | 0.0907 (5) | 0.0601 (4) | 0.0516 (4) | 0.0205 (3) | 0.0371 (3) | 0.0163 (3) |
C13 | 0.0664 (15) | 0.0572 (14) | 0.0604 (16) | −0.0082 (11) | 0.0326 (13) | 0.0072 (12) |
C14 | 0.0567 (13) | 0.0609 (14) | 0.0534 (14) | −0.0148 (11) | 0.0203 (11) | 0.0016 (11) |
Geometric parameters (Å, º) top
N1—C6 | 1.353 (3) | C8—O8 | 1.213 (3) |
N1—C2 | 1.399 (3) | C8—C9 | 1.477 (3) |
N1—C7 | 1.455 (3) | C9—C10 | 1.395 (3) |
C2—O2 | 1.226 (3) | C9—C14 | 1.396 (3) |
C2—N3 | 1.364 (3) | C10—C11 | 1.382 (3) |
N3—C4 | 1.307 (3) | C10—H10 | 0.9300 |
C4—C5 | 1.397 (3) | C11—C12 | 1.379 (3) |
C4—H4 | 0.9300 | C11—H11 | 0.9300 |
C5—C6 | 1.341 (4) | C12—C13 | 1.384 (4) |
C5—H5 | 0.9300 | C12—Cl12 | 1.742 (2) |
C6—H6 | 0.9300 | C13—C14 | 1.371 (4) |
C7—C8 | 1.514 (3) | C13—H13 | 0.9300 |
C7—H7A | 0.9700 | C14—H14 | 0.9300 |
C7—H7B | 0.9700 | ||
C6—N1—C2 | 121.49 (19) | O8—C8—C9 | 122.0 (2) |
C6—N1—C7 | 120.52 (19) | O8—C8—C7 | 119.5 (2) |
C2—N1—C7 | 117.84 (19) | C9—C8—C7 | 118.47 (19) |
O2—C2—N3 | 122.8 (2) | C10—C9—C14 | 118.8 (2) |
O2—C2—N1 | 119.7 (2) | C10—C9—C8 | 122.9 (2) |
N3—C2—N1 | 117.53 (19) | C14—C9—C8 | 118.3 (2) |
C4—N3—C2 | 119.42 (19) | C11—C10—C9 | 120.3 (2) |
N3—C4—C5 | 124.3 (2) | C11—C10—H10 | 119.9 |
N3—C4—H4 | 117.8 | C9—C10—H10 | 119.9 |
C5—C4—H4 | 117.8 | C12—C11—C10 | 119.4 (2) |
C6—C5—C4 | 116.6 (2) | C12—C11—H11 | 120.3 |
C6—C5—H5 | 121.7 | C10—C11—H11 | 120.3 |
C4—C5—H5 | 121.7 | C11—C12—C13 | 121.4 (2) |
C5—C6—N1 | 120.5 (2) | C11—C12—Cl12 | 119.3 (2) |
C5—C6—H6 | 119.7 | C13—C12—Cl12 | 119.22 (19) |
N1—C6—H6 | 119.7 | C14—C13—C12 | 118.8 (2) |
N1—C7—C8 | 111.92 (19) | C14—C13—H13 | 120.6 |
N1—C7—H7A | 109.2 | C12—C13—H13 | 120.6 |
C8—C7—H7A | 109.2 | C13—C14—C9 | 121.3 (2) |
N1—C7—H7B | 109.2 | C13—C14—H14 | 119.4 |
C8—C7—H7B | 109.2 | C9—C14—H14 | 119.4 |
H7A—C7—H7B | 107.9 |