In the title compound, C19H19FN4O3, the two heterocyclic ring substituents lie on the same side of the central benzene ring.
Supporting information
CCDC reference: 277702
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.050
- wR factor = 0.173
- Data-to-parameter ratio = 16.0
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT411_ALERT_2_B Short Inter H...H Contact H7A .. H7A .. 2.01 Ang.
PLAT414_ALERT_2_B Short Intra D-H..H-X HN1 .. H13A .. 1.81 Ang.
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C13
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: please supply; software used to prepare material for publication: CrystalStructure.
2-(4,6-Dimethoxypyrimidin-2-yloxy)-6-fluoro-
N-(3-methylpyridyl)benzylamine
top
Crystal data top
C19H19FN4O3 | Z = 2 |
Mr = 370.38 | F(000) = 388.00 |
Triclinic, P1 | Dx = 1.376 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.849 (1) Å | Cell parameters from 3528 reflections |
b = 10.581 (1) Å | θ = 3.5–27.5° |
c = 11.3773 (8) Å | µ = 0.10 mm−1 |
α = 113.447 (1)° | T = 295 K |
β = 98.852 (1)° | Block, colorless |
γ = 106.364 (2)° | 0.42 × 0.38 × 0.22 mm |
V = 893.89 (15) Å3 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2983 reflections with I > 2σ(I) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.022 |
ω scans | θmax = 27.5°, θmin = 2.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −11→11 |
Tmin = 0.940, Tmax = 0.978 | k = −12→13 |
6292 measured reflections | l = −14→14 |
3991 independent reflections | |
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)] = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.173 | w = 1/[σ2(Fo2) + (0.1093P)2 + 0.0797P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3991 reflections | Δρmax = 0.43 e Å−3 |
249 parameters | Δρmin = −0.33 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: 0.050 (8) |
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 | |
C19 | 0.0518 (3) | 0.4570 (3) | 0.6517 (2) | 0.0642 (6) | |
H19A | 0.0862 | 0.5445 | 0.7366 | 0.096* | |
H19B | −0.0615 | 0.3966 | 0.6324 | 0.096* | |
H19C | 0.0629 | 0.4855 | 0.5823 | 0.096* | |
O3 | 0.15275 (18) | 0.37420 (16) | 0.65755 (13) | 0.0571 (4) | |
C18 | 0.1247 (2) | 0.2473 (2) | 0.54903 (17) | 0.0430 (4) | |
C10 | 0.3747 (2) | 0.5012 (2) | 0.3153 (2) | 0.0559 (5) | |
H10 | 0.4648 | 0.5713 | 0.3900 | 0.067* | |
C17 | 0.2302 (2) | 0.1753 (2) | 0.55333 (18) | 0.0480 (4) | |
H17 | 0.3160 | 0.2093 | 0.6304 | 0.058* | |
C9 | 0.2567 (2) | 0.3925 (2) | 0.32238 (19) | 0.0508 (5) | |
H9 | 0.2694 | 0.3896 | 0.4039 | 0.061* | |
C11 | 0.3570 (2) | 0.5047 (2) | 0.1936 (2) | 0.0555 (5) | |
H11 | 0.4376 | 0.5767 | 0.1856 | 0.067* | |
N4 | −0.00199 (17) | 0.19744 (16) | 0.44190 (13) | 0.0417 (3) | |
C15 | 0.2016 (2) | 0.0490 (2) | 0.43636 (18) | 0.0433 (4) | |
O2 | 0.30662 (17) | −0.01969 (17) | 0.43701 (14) | 0.0576 (4) | |
N2 | 0.12326 (17) | 0.28925 (17) | 0.21955 (14) | 0.0450 (4) | |
C12 | 0.2223 (2) | 0.4033 (2) | 0.08507 (19) | 0.0480 (4) | |
C14 | −0.01760 (19) | 0.07357 (19) | 0.33883 (16) | 0.0399 (4) | |
N3 | 0.07727 (17) | −0.00513 (16) | 0.32577 (14) | 0.0426 (4) | |
C16 | 0.2832 (3) | −0.1497 (3) | 0.3189 (2) | 0.0688 (6) | |
H16A | 0.3682 | −0.1860 | 0.3346 | 0.103* | |
H16B | 0.2884 | −0.1260 | 0.2461 | 0.103* | |
H16C | 0.1771 | −0.2248 | 0.2963 | 0.103* | |
C8 | 0.1059 (2) | 0.29660 (19) | 0.10413 (17) | 0.0409 (4) | |
C3 | −0.4448 (2) | 0.1928 (2) | 0.2747 (2) | 0.0585 (5) | |
H3 | −0.5083 | 0.2185 | 0.3315 | 0.070* | |
C4 | −0.3421 (2) | 0.1243 (2) | 0.2978 (2) | 0.0527 (5) | |
H4 | −0.3373 | 0.1010 | 0.3686 | 0.063* | |
C13 | 0.1972 (4) | 0.4033 (3) | −0.0486 (2) | 0.0792 (8) | |
H13A | 0.0954 | 0.3239 | −0.1108 | 0.119* | |
H13B | 0.2873 | 0.3892 | −0.0823 | 0.119* | |
H13C | 0.1928 | 0.4967 | −0.0380 | 0.119* | |
C2 | −0.4550 (2) | 0.2239 (2) | 0.1679 (2) | 0.0552 (5) | |
H2 | −0.5253 | 0.2698 | 0.1515 | 0.066* | |
C5 | −0.24492 (19) | 0.09004 (19) | 0.21373 (17) | 0.0415 (4) | |
O1 | −0.14749 (15) | 0.01096 (14) | 0.22764 (12) | 0.0469 (3) | |
C1 | −0.3592 (2) | 0.1857 (2) | 0.08630 (18) | 0.0468 (4) | |
C6 | −0.24989 (19) | 0.11984 (18) | 0.10563 (16) | 0.0402 (4) | |
N1 | −0.03503 (18) | 0.19620 (18) | 0.00161 (16) | 0.0477 (4) | |
F1 | −0.37115 (16) | 0.21398 (15) | −0.02089 (12) | 0.0660 (4) | |
C7 | −0.1505 (2) | 0.0748 (2) | 0.01023 (18) | 0.0461 (4) | |
H7A | −0.0895 | 0.0234 | 0.0383 | 0.055* | |
H7B | −0.2266 | 0.0048 | −0.0789 | 0.055* | |
HN1 | −0.037 (2) | 0.182 (2) | −0.081 (2) | 0.048 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C19 | 0.0749 (14) | 0.0536 (12) | 0.0559 (12) | 0.0290 (11) | 0.0138 (10) | 0.0168 (10) |
O3 | 0.0643 (8) | 0.0536 (8) | 0.0397 (7) | 0.0240 (7) | 0.0043 (6) | 0.0118 (6) |
C18 | 0.0425 (8) | 0.0446 (9) | 0.0369 (9) | 0.0113 (7) | 0.0101 (7) | 0.0185 (7) |
C10 | 0.0451 (10) | 0.0523 (11) | 0.0489 (11) | 0.0080 (8) | 0.0047 (8) | 0.0140 (9) |
C17 | 0.0418 (9) | 0.0550 (11) | 0.0408 (10) | 0.0141 (8) | 0.0034 (7) | 0.0225 (8) |
C9 | 0.0477 (9) | 0.0572 (11) | 0.0430 (10) | 0.0176 (8) | 0.0109 (7) | 0.0216 (9) |
C11 | 0.0532 (11) | 0.0451 (10) | 0.0586 (12) | 0.0093 (8) | 0.0184 (9) | 0.0208 (9) |
N4 | 0.0405 (7) | 0.0432 (8) | 0.0390 (8) | 0.0156 (6) | 0.0087 (6) | 0.0182 (6) |
C15 | 0.0377 (8) | 0.0505 (10) | 0.0485 (10) | 0.0172 (7) | 0.0122 (7) | 0.0291 (8) |
O2 | 0.0536 (8) | 0.0703 (9) | 0.0566 (8) | 0.0352 (7) | 0.0106 (6) | 0.0308 (7) |
N2 | 0.0403 (7) | 0.0503 (9) | 0.0418 (8) | 0.0156 (6) | 0.0114 (6) | 0.0202 (7) |
C12 | 0.0526 (10) | 0.0414 (10) | 0.0472 (10) | 0.0153 (8) | 0.0159 (8) | 0.0192 (8) |
C14 | 0.0371 (8) | 0.0426 (9) | 0.0400 (9) | 0.0138 (7) | 0.0086 (6) | 0.0213 (7) |
N3 | 0.0404 (7) | 0.0442 (8) | 0.0441 (8) | 0.0169 (6) | 0.0104 (6) | 0.0215 (7) |
C16 | 0.0715 (14) | 0.0703 (15) | 0.0703 (14) | 0.0446 (12) | 0.0160 (11) | 0.0280 (12) |
C8 | 0.0414 (8) | 0.0412 (9) | 0.0409 (9) | 0.0201 (7) | 0.0134 (7) | 0.0166 (7) |
C3 | 0.0423 (9) | 0.0692 (13) | 0.0571 (12) | 0.0252 (9) | 0.0168 (8) | 0.0195 (10) |
C4 | 0.0446 (9) | 0.0619 (12) | 0.0465 (10) | 0.0189 (9) | 0.0118 (8) | 0.0219 (9) |
C13 | 0.0933 (17) | 0.0704 (16) | 0.0594 (14) | 0.0034 (13) | 0.0176 (12) | 0.0372 (12) |
C2 | 0.0419 (9) | 0.0542 (11) | 0.0639 (13) | 0.0254 (8) | 0.0095 (8) | 0.0196 (10) |
C5 | 0.0323 (7) | 0.0386 (9) | 0.0419 (9) | 0.0112 (7) | 0.0021 (6) | 0.0126 (7) |
O1 | 0.0426 (6) | 0.0436 (7) | 0.0437 (7) | 0.0185 (5) | 0.0008 (5) | 0.0129 (5) |
C1 | 0.0430 (9) | 0.0453 (10) | 0.0456 (10) | 0.0165 (8) | 0.0050 (7) | 0.0182 (8) |
C6 | 0.0315 (7) | 0.0342 (8) | 0.0417 (9) | 0.0092 (6) | 0.0042 (6) | 0.0099 (7) |
N1 | 0.0421 (8) | 0.0522 (9) | 0.0407 (8) | 0.0127 (7) | 0.0093 (6) | 0.0188 (7) |
F1 | 0.0723 (8) | 0.0757 (9) | 0.0641 (8) | 0.0380 (7) | 0.0160 (6) | 0.0407 (7) |
C7 | 0.0417 (9) | 0.0429 (10) | 0.0429 (9) | 0.0138 (7) | 0.0101 (7) | 0.0122 (7) |
Geometric parameters (Å, º) top
C19—O3 | 1.428 (2) | C14—O1 | 1.3479 (19) |
C19—H19A | 0.9600 | C16—H16A | 0.9600 |
C19—H19B | 0.9600 | C16—H16B | 0.9600 |
C19—H19C | 0.9600 | C16—H16C | 0.9600 |
O3—C18 | 1.337 (2) | C8—N1 | 1.365 (2) |
C18—N4 | 1.325 (2) | C3—C4 | 1.367 (3) |
C18—C17 | 1.367 (3) | C3—C2 | 1.375 (3) |
C10—C9 | 1.358 (3) | C3—H3 | 0.9300 |
C10—C11 | 1.386 (3) | C4—C5 | 1.393 (3) |
C10—H10 | 0.9300 | C4—H4 | 0.9300 |
C17—C15 | 1.383 (3) | C13—H13A | 0.9600 |
C17—H17 | 0.9300 | C13—H13B | 0.9600 |
C9—N2 | 1.337 (2) | C13—H13C | 0.9600 |
C9—H9 | 0.9300 | C2—C1 | 1.371 (3) |
C11—C12 | 1.367 (3) | C2—H2 | 0.9300 |
C11—H11 | 0.9300 | C5—C6 | 1.383 (2) |
N4—C14 | 1.318 (2) | C5—O1 | 1.3922 (19) |
C15—N3 | 1.329 (2) | C1—F1 | 1.363 (2) |
C15—O2 | 1.332 (2) | C1—C6 | 1.381 (2) |
O2—C16 | 1.422 (3) | C6—C7 | 1.516 (2) |
N2—C8 | 1.334 (2) | N1—C7 | 1.447 (2) |
C12—C8 | 1.411 (3) | N1—HN1 | 0.89 (2) |
C12—C13 | 1.503 (3) | C7—H7A | 0.9700 |
C14—N3 | 1.324 (2) | C7—H7B | 0.9700 |
| | | |
O3—C19—H19A | 109.5 | H16A—C16—H16C | 109.5 |
O3—C19—H19B | 109.5 | H16B—C16—H16C | 109.5 |
H19A—C19—H19B | 109.5 | N2—C8—N1 | 116.89 (16) |
O3—C19—H19C | 109.5 | N2—C8—C12 | 123.53 (16) |
H19A—C19—H19C | 109.5 | N1—C8—C12 | 119.57 (16) |
H19B—C19—H19C | 109.5 | C4—C3—C2 | 120.47 (18) |
C18—O3—C19 | 119.06 (15) | C4—C3—H3 | 119.8 |
N4—C18—O3 | 119.03 (16) | C2—C3—H3 | 119.8 |
N4—C18—C17 | 122.82 (17) | C3—C4—C5 | 118.97 (19) |
O3—C18—C17 | 118.14 (15) | C3—C4—H4 | 120.5 |
C9—C10—C11 | 118.10 (18) | C5—C4—H4 | 120.5 |
C9—C10—H10 | 120.9 | C12—C13—H13A | 109.5 |
C11—C10—H10 | 120.9 | C12—C13—H13B | 109.5 |
C18—C17—C15 | 116.05 (15) | H13A—C13—H13B | 109.5 |
C18—C17—H17 | 122.0 | C12—C13—H13C | 109.5 |
C15—C17—H17 | 122.0 | H13A—C13—H13C | 109.5 |
N2—C9—C10 | 124.09 (18) | H13B—C13—H13C | 109.5 |
N2—C9—H9 | 118.0 | C1—C2—C3 | 118.56 (17) |
C10—C9—H9 | 118.0 | C1—C2—H2 | 120.7 |
C12—C11—C10 | 120.61 (18) | C3—C2—H2 | 120.7 |
C12—C11—H11 | 119.7 | C6—C5—O1 | 116.13 (15) |
C10—C11—H11 | 119.7 | C6—C5—C4 | 122.74 (16) |
C14—N4—C18 | 114.73 (15) | O1—C5—C4 | 120.88 (17) |
N3—C15—O2 | 119.50 (16) | C14—O1—C5 | 119.72 (13) |
N3—C15—C17 | 123.55 (16) | F1—C1—C2 | 118.69 (16) |
O2—C15—C17 | 116.94 (15) | F1—C1—C6 | 117.22 (16) |
C15—O2—C16 | 119.15 (14) | C2—C1—C6 | 124.09 (18) |
C8—N2—C9 | 117.04 (16) | C1—C6—C5 | 115.14 (16) |
C11—C12—C8 | 116.59 (17) | C1—C6—C7 | 122.33 (17) |
C11—C12—C13 | 122.54 (19) | C5—C6—C7 | 122.43 (15) |
C8—C12—C13 | 120.87 (18) | C8—N1—C7 | 122.03 (16) |
N4—C14—N3 | 129.47 (15) | C8—N1—HN1 | 118.2 (13) |
N4—C14—O1 | 118.85 (14) | C7—N1—HN1 | 115.4 (13) |
N3—C14—O1 | 111.67 (14) | N1—C7—C6 | 115.16 (15) |
C14—N3—C15 | 113.29 (15) | N1—C7—H7A | 108.5 |
O2—C16—H16A | 109.5 | C6—C7—H7A | 108.5 |
O2—C16—H16B | 109.5 | N1—C7—H7B | 108.5 |
H16A—C16—H16B | 109.5 | C6—C7—H7B | 108.5 |
O2—C16—H16C | 109.5 | H7A—C7—H7B | 107.5 |
| | | |
C19—O3—C18—N4 | −4.0 (3) | C11—C12—C8—N1 | 177.16 (17) |
C19—O3—C18—C17 | 175.31 (19) | C13—C12—C8—N1 | −2.9 (3) |
N4—C18—C17—C15 | 2.6 (3) | C2—C3—C4—C5 | 1.6 (3) |
O3—C18—C17—C15 | −176.63 (15) | C4—C3—C2—C1 | −0.5 (3) |
C11—C10—C9—N2 | −0.7 (3) | C3—C4—C5—C6 | −1.2 (3) |
C9—C10—C11—C12 | 1.5 (3) | C3—C4—C5—O1 | −175.39 (16) |
O3—C18—N4—C14 | 178.51 (15) | N4—C14—O1—C5 | 11.5 (2) |
C17—C18—N4—C14 | −0.7 (3) | N3—C14—O1—C5 | −169.21 (14) |
C18—C17—C15—N3 | −2.0 (3) | C6—C5—O1—C14 | 118.46 (17) |
C18—C17—C15—O2 | 177.65 (16) | C4—C5—O1—C14 | −67.0 (2) |
N3—C15—O2—C16 | 0.0 (3) | C3—C2—C1—F1 | 178.87 (17) |
C17—C15—O2—C16 | −179.65 (18) | C3—C2—C1—C6 | −1.2 (3) |
C10—C9—N2—C8 | −1.0 (3) | F1—C1—C6—C5 | −178.53 (15) |
C10—C11—C12—C8 | −0.5 (3) | C2—C1—C6—C5 | 1.6 (3) |
C10—C11—C12—C13 | 179.6 (2) | F1—C1—C6—C7 | −2.2 (2) |
C18—N4—C14—N3 | −2.2 (3) | C2—C1—C6—C7 | 177.95 (17) |
C18—N4—C14—O1 | 176.98 (15) | O1—C5—C6—C1 | 174.08 (14) |
N4—C14—N3—C15 | 2.7 (3) | C4—C5—C6—C1 | −0.3 (2) |
O1—C14—N3—C15 | −176.50 (14) | O1—C5—C6—C7 | −2.3 (2) |
O2—C15—N3—C14 | 179.95 (15) | C4—C5—C6—C7 | −176.68 (17) |
C17—C15—N3—C14 | −0.4 (2) | N2—C8—N1—C7 | −7.9 (2) |
C9—N2—C8—N1 | −176.45 (16) | C12—C8—N1—C7 | 173.45 (16) |
C9—N2—C8—C12 | 2.1 (3) | C8—N1—C7—C6 | 71.4 (2) |
C11—C12—C8—N2 | −1.4 (3) | C1—C6—C7—N1 | 63.1 (2) |
C13—C12—C8—N2 | 178.57 (19) | C5—C6—C7—N1 | −120.78 (18) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—HN1···N3i | 0.89 (2) | 2.56 (2) | 3.355 (2) | 149.4 (19) |
Symmetry code: (i) −x, −y, −z. |