2-(4,6-Dimethoxy­pyrimidin-2-yl­oxy)-6-fluoro-N-(3-methyl­pyrid­yl)benzyl­amine

In the title compound, C₁₉H₁₉FN₄O₃, the two heterocyclic ring substituents lie on the same side of the central benzene ring.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.173	w = 1/[σ^2(Fo^2) + (0.1093P)^2 + 0.0797P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.050 (8)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···N3^i	0.89 (2)	2.56 (2)	3.355 (2)	149.4 (19)

Symmetry code: (i) −x, −y, −z.