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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
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
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(1
H)-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 | | |
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