In the title compound, C
14H
14ClN
3O
2, the pyrimidine ring is twisted with respect to the benzene ring, making a dihedral angle of 42.77 (5)°. The crystal packing is stabilized by N—H
O, N—H
N and C—H
Cl hydrogen bonds.
Supporting information
CCDC reference: 628434
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C)= 0.002 Å
- R factor = 0.031
- wR factor = 0.090
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
Crystal data top
C14H14ClN3O2 | F(000) = 608 |
Mr = 291.73 | Dx = 1.416 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 12101 reflections |
a = 9.1751 (2) Å | θ = 3.1–27.5° |
b = 9.2232 (2) Å | µ = 0.28 mm−1 |
c = 16.2613 (3) Å | T = 153 K |
β = 96.223 (1)° | Block, colourless |
V = 1367.98 (5) Å3 | 0.50 × 0.44 × 0.27 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2916 reflections with I > 2σ(I) |
Radiation source: Rotating Anode | Rint = 0.016 |
Graphite monochromator | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −11→11 |
13106 measured reflections | k = −11→11 |
3118 independent reflections | l = −20→21 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.0512P)2 + 0.639P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
3118 reflections | Δρmax = 0.35 e Å−3 |
192 parameters | Δρmin = −0.36 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0099 (17) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 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 (Å2) top | x | y | z | Uiso*/Ueq | |
Cl | 0.96445 (3) | 0.56130 (4) | 0.594010 (19) | 0.03022 (12) | |
O1 | 0.48770 (9) | 0.28768 (9) | 0.75532 (5) | 0.02119 (19) | |
O2 | 0.28390 (10) | 0.41609 (11) | 0.77055 (5) | 0.0281 (2) | |
N1 | 0.33901 (10) | 0.19080 (10) | 0.51325 (6) | 0.0180 (2) | |
N2 | 0.11347 (10) | 0.13062 (11) | 0.56816 (6) | 0.0197 (2) | |
N3 | 0.16205 (12) | 0.05230 (12) | 0.43972 (6) | 0.0228 (2) | |
C1 | 0.64235 (12) | 0.26975 (13) | 0.55261 (7) | 0.0193 (2) | |
H1 | 0.6295 | 0.1752 | 0.5298 | 0.023* | |
C2 | 0.77822 (12) | 0.33747 (13) | 0.55462 (7) | 0.0214 (2) | |
H2 | 0.8586 | 0.2895 | 0.5342 | 0.026* | |
C3 | 0.79400 (13) | 0.47664 (13) | 0.58708 (7) | 0.0206 (2) | |
C4 | 0.67742 (13) | 0.54953 (12) | 0.61580 (7) | 0.0207 (2) | |
H4 | 0.6895 | 0.6457 | 0.6364 | 0.025* | |
C5 | 0.54312 (13) | 0.48033 (13) | 0.61405 (7) | 0.0198 (2) | |
H5 | 0.4627 | 0.5294 | 0.6337 | 0.024* | |
C6 | 0.52483 (12) | 0.33918 (12) | 0.58368 (6) | 0.0170 (2) | |
C7 | 0.38214 (12) | 0.26279 (12) | 0.58260 (7) | 0.0168 (2) | |
C8 | 0.20634 (12) | 0.12648 (12) | 0.50875 (7) | 0.0179 (2) | |
C9 | 0.15860 (12) | 0.20124 (13) | 0.63796 (7) | 0.0195 (2) | |
C10 | 0.29644 (12) | 0.26900 (12) | 0.64942 (7) | 0.0180 (2) | |
C11 | 0.35166 (12) | 0.33447 (13) | 0.73048 (7) | 0.0195 (2) | |
C12 | 0.56557 (14) | 0.36010 (15) | 0.82669 (7) | 0.0265 (3) | |
H12A | 0.5244 | 0.3313 | 0.8781 | 0.032* | |
H12B | 0.5575 | 0.4667 | 0.8206 | 0.032* | |
C13 | 0.72342 (15) | 0.31307 (17) | 0.82954 (9) | 0.0348 (3) | |
H13A | 0.7293 | 0.2072 | 0.8342 | 0.042* | |
H13B | 0.7805 | 0.3573 | 0.8775 | 0.042* | |
H13C | 0.7631 | 0.3441 | 0.7788 | 0.042* | |
C14 | 0.05495 (14) | 0.19872 (17) | 0.70326 (7) | 0.0289 (3) | |
H14A | −0.0326 | 0.1428 | 0.6833 | 0.035* | |
H14B | 0.0265 | 0.2981 | 0.7156 | 0.035* | |
H14C | 0.1033 | 0.1536 | 0.7536 | 0.035* | |
H3A | 0.2163 (18) | 0.0531 (17) | 0.4007 (10) | 0.027 (4)* | |
H3B | 0.0792 (18) | 0.0052 (18) | 0.4373 (10) | 0.026 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl | 0.02518 (17) | 0.0389 (2) | 0.02844 (18) | −0.01386 (12) | 0.01160 (12) | −0.01141 (12) |
O1 | 0.0209 (4) | 0.0253 (4) | 0.0167 (4) | −0.0010 (3) | −0.0005 (3) | 0.0001 (3) |
O2 | 0.0273 (5) | 0.0363 (5) | 0.0218 (4) | 0.0029 (4) | 0.0073 (3) | −0.0064 (4) |
N1 | 0.0175 (4) | 0.0199 (5) | 0.0171 (4) | 0.0003 (4) | 0.0045 (3) | 0.0011 (4) |
N2 | 0.0171 (4) | 0.0252 (5) | 0.0174 (4) | −0.0008 (4) | 0.0042 (3) | 0.0017 (4) |
N3 | 0.0218 (5) | 0.0278 (5) | 0.0200 (5) | −0.0061 (4) | 0.0072 (4) | −0.0045 (4) |
C1 | 0.0192 (5) | 0.0204 (5) | 0.0186 (5) | 0.0005 (4) | 0.0034 (4) | −0.0028 (4) |
C2 | 0.0180 (5) | 0.0265 (6) | 0.0207 (5) | 0.0005 (4) | 0.0058 (4) | −0.0032 (4) |
C3 | 0.0197 (5) | 0.0260 (6) | 0.0166 (5) | −0.0053 (4) | 0.0046 (4) | −0.0003 (4) |
C4 | 0.0263 (6) | 0.0184 (5) | 0.0182 (5) | −0.0022 (4) | 0.0058 (4) | −0.0003 (4) |
C5 | 0.0219 (5) | 0.0197 (5) | 0.0186 (5) | 0.0028 (4) | 0.0063 (4) | 0.0014 (4) |
C6 | 0.0176 (5) | 0.0200 (5) | 0.0136 (5) | 0.0007 (4) | 0.0031 (4) | 0.0025 (4) |
C7 | 0.0169 (5) | 0.0172 (5) | 0.0167 (5) | 0.0031 (4) | 0.0030 (4) | 0.0032 (4) |
C8 | 0.0183 (5) | 0.0182 (5) | 0.0176 (5) | 0.0010 (4) | 0.0034 (4) | 0.0023 (4) |
C9 | 0.0177 (5) | 0.0248 (6) | 0.0163 (5) | 0.0016 (4) | 0.0035 (4) | 0.0034 (4) |
C10 | 0.0179 (5) | 0.0213 (5) | 0.0152 (5) | 0.0022 (4) | 0.0034 (4) | 0.0016 (4) |
C11 | 0.0202 (5) | 0.0228 (6) | 0.0162 (5) | −0.0022 (4) | 0.0046 (4) | 0.0027 (4) |
C12 | 0.0275 (6) | 0.0311 (6) | 0.0199 (6) | −0.0066 (5) | −0.0018 (5) | −0.0020 (5) |
C13 | 0.0252 (6) | 0.0399 (8) | 0.0375 (7) | −0.0077 (6) | −0.0047 (5) | 0.0003 (6) |
C14 | 0.0218 (6) | 0.0478 (8) | 0.0182 (5) | −0.0063 (5) | 0.0072 (4) | −0.0018 (5) |
Geometric parameters (Å, º) top
Cl—C3 | 1.7406 (12) | C4—H4 | 0.9500 |
O1—C11 | 1.3410 (14) | C5—C6 | 1.3960 (16) |
O1—C12 | 1.4573 (14) | C5—H5 | 0.9500 |
O2—C11 | 1.2106 (15) | C6—C7 | 1.4851 (15) |
N1—C7 | 1.3314 (14) | C7—C10 | 1.4098 (15) |
N1—C8 | 1.3490 (14) | C9—C10 | 1.4049 (16) |
N2—C9 | 1.3350 (15) | C9—C14 | 1.5005 (16) |
N2—C8 | 1.3562 (14) | C10—C11 | 1.4880 (15) |
N3—C8 | 1.3396 (15) | C12—C13 | 1.5077 (19) |
N3—H3A | 0.848 (17) | C12—H12A | 0.9900 |
N3—H3B | 0.873 (17) | C12—H12B | 0.9900 |
C1—C2 | 1.3916 (16) | C13—H13A | 0.9800 |
C1—C6 | 1.3950 (15) | C13—H13B | 0.9800 |
C1—H1 | 0.9500 | C13—H13C | 0.9800 |
C2—C3 | 1.3894 (17) | C14—H14A | 0.9800 |
C2—H2 | 0.9500 | C14—H14B | 0.9800 |
C3—C4 | 1.3866 (16) | C14—H14C | 0.9800 |
C4—C5 | 1.3852 (16) | | |
| | | |
C11—O1—C12 | 116.89 (9) | N1—C8—N2 | 125.59 (10) |
C7—N1—C8 | 116.67 (9) | N2—C9—C10 | 121.45 (10) |
C9—N2—C8 | 117.29 (10) | N2—C9—C14 | 115.60 (10) |
C8—N3—H3A | 118.2 (11) | C10—C9—C14 | 122.92 (10) |
C8—N3—H3B | 118.4 (10) | C9—C10—C7 | 116.68 (10) |
H3A—N3—H3B | 123.4 (15) | C9—C10—C11 | 120.88 (10) |
C2—C1—C6 | 120.73 (11) | C7—C10—C11 | 122.31 (10) |
C2—C1—H1 | 119.6 | O2—C11—O1 | 123.62 (11) |
C6—C1—H1 | 119.6 | O2—C11—C10 | 125.71 (11) |
C3—C2—C1 | 118.67 (10) | O1—C11—C10 | 110.65 (9) |
C3—C2—H2 | 120.7 | O1—C12—C13 | 106.20 (10) |
C1—C2—H2 | 120.7 | O1—C12—H12A | 110.5 |
C4—C3—C2 | 121.56 (11) | C13—C12—H12A | 110.5 |
C4—C3—Cl | 118.76 (9) | O1—C12—H12B | 110.5 |
C2—C3—Cl | 119.67 (9) | C13—C12—H12B | 110.5 |
C5—C4—C3 | 119.12 (11) | H12A—C12—H12B | 108.7 |
C5—C4—H4 | 120.4 | C12—C13—H13A | 109.5 |
C3—C4—H4 | 120.4 | C12—C13—H13B | 109.5 |
C4—C5—C6 | 120.63 (10) | H13A—C13—H13B | 109.5 |
C4—C5—H5 | 119.7 | C12—C13—H13C | 109.5 |
C6—C5—H5 | 119.7 | H13A—C13—H13C | 109.5 |
C1—C6—C5 | 119.22 (10) | H13B—C13—H13C | 109.5 |
C1—C6—C7 | 119.53 (10) | C9—C14—H14A | 109.5 |
C5—C6—C7 | 121.24 (10) | C9—C14—H14B | 109.5 |
N1—C7—C10 | 122.26 (10) | H14A—C14—H14B | 109.5 |
N1—C7—C6 | 115.30 (9) | C9—C14—H14C | 109.5 |
C10—C7—C6 | 122.42 (10) | H14A—C14—H14C | 109.5 |
N3—C8—N1 | 117.39 (10) | H14B—C14—H14C | 109.5 |
N3—C8—N2 | 117.03 (10) | | |
| | | |
C6—C1—C2—C3 | −0.95 (17) | C9—N2—C8—N1 | −1.82 (17) |
C1—C2—C3—C4 | −1.20 (18) | C8—N2—C9—C10 | 0.22 (16) |
C1—C2—C3—Cl | 177.55 (9) | C8—N2—C9—C14 | −177.89 (11) |
C2—C3—C4—C5 | 1.73 (18) | N2—C9—C10—C7 | 2.08 (16) |
Cl—C3—C4—C5 | −177.03 (9) | C14—C9—C10—C7 | −179.96 (11) |
C3—C4—C5—C6 | −0.12 (17) | N2—C9—C10—C11 | −173.79 (10) |
C2—C1—C6—C5 | 2.51 (17) | C14—C9—C10—C11 | 4.17 (17) |
C2—C1—C6—C7 | −178.50 (10) | N1—C7—C10—C9 | −3.13 (16) |
C4—C5—C6—C1 | −1.97 (16) | C6—C7—C10—C9 | 175.21 (10) |
C4—C5—C6—C7 | 179.07 (10) | N1—C7—C10—C11 | 172.68 (10) |
C8—N1—C7—C10 | 1.74 (15) | C6—C7—C10—C11 | −8.98 (16) |
C8—N1—C7—C6 | −176.71 (9) | C12—O1—C11—O2 | −11.42 (16) |
C1—C6—C7—N1 | −42.93 (14) | C12—O1—C11—C10 | 170.22 (9) |
C5—C6—C7—N1 | 136.04 (11) | C9—C10—C11—O2 | −48.80 (17) |
C1—C6—C7—C10 | 138.62 (11) | C7—C10—C11—O2 | 135.56 (13) |
C5—C6—C7—C10 | −42.41 (15) | C9—C10—C11—O1 | 129.51 (11) |
C7—N1—C8—N3 | −179.30 (10) | C7—C10—C11—O1 | −46.12 (14) |
C7—N1—C8—N2 | 0.84 (16) | C11—O1—C12—C13 | −167.26 (10) |
C9—N2—C8—N3 | 178.32 (10) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O2i | 0.848 (17) | 2.287 (17) | 3.0933 (13) | 159.0 (15) |
N3—H3B···N2ii | 0.873 (17) | 2.161 (17) | 3.0303 (14) | 174.4 (15) |
C14—H14C···Cliii | 0.98 | 2.75 | 3.5543 (12) | 139 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, −y, −z+1; (iii) −x+1, y−1/2, −z+3/2. |