tert-Butyl N-benzyl-N-[4-(4-fluoro-benzoyl-meth-yl)-2-pyrid-yl]carbamate.

In the crystal structure of the title compound, C(25)H(25)FN(2)O(3), the pyridine ring makes dihedral angles of 75.1 (3), 39.4 (3) and 74.6 (3)° with the phenyl ring, the carbamate plane and the 4-fluoro-phenyl ring, respectively. The phenyl ring makes dihedral angles of 77.2 (3) and 23.6 (3)° with the carbamate plane and the 4-fluoro-phenyl ring, respectively. The 4-fluoro-phenyl ring is perpendicular to the carbamate plane, the dihedral angle between them being 89.5 (3)°.

Related literature

For preparation of the title compound, see: Koch et al. (2008a ▶). For applications of the vicinal 4-fluoro­phen­yl/pyridin-4-yl pharmacophore in p38 MAP kinase inhibitors, see, for example: Koch et al. (2008a ▶); for thia­zolopyridines, see: Miwatashi et al. (2005 ▶); for pyrazolopyridines, see: Stevens et al. (2005 ▶). For a related structure, see: Koch, et al. (2008b ▶).

Experimental

Crystal data

C25H25FN2O3

M = 420.47

Monoclinic,

a = 38.054 (7) Å

b = 7.9320 (6) Å

c = 14.589 (3) Å

β = 102.142 (8)°

V = 4305.1 (11) Å3

Z = 8

Cu Kα radiation

μ = 0.75 mm−1

T = 193 (2) K

0.35 × 0.30 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

4272 measured reflections

4091 independent reflections

2192 reflections with I > 2σ(I)

R int = 0.076

3 standard reflections frequency: 60 min intensity decay: 3%

Refinement

R[F 2 > 2σ(F 2)] = 0.110

wR(F 2) = 0.339

S = 1.10

4091 reflections

283 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.64 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680803448X/si2118sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803448X/si2118Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H25FN2O3	F(000) = 1776
Mr = 420.47	Dx = 1.297 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 38.054 (7) Å	θ = 15–28°
b = 7.9320 (6) Å	µ = 0.75 mm−1
c = 14.589 (3) Å	T = 193 K
β = 102.142 (8)°	Plate, colourless
V = 4305.1 (11) Å3	0.35 × 0.30 × 0.18 mm
Z = 8

Enraf–Nonius CAD-4 diffractometer	Rint = 0.076
Radiation source: rotating anode	θmax = 70.1°, θmin = 2.4°
graphite	h = −46→45
ω/2θ scans	k = −9→0
4272 measured reflections	l = 0→17
4091 independent reflections	3 standard reflections every 60 min
2192 reflections with I > 2σ(I)	intensity decay: 3%

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.110	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.339	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.182P)2] where P = (Fo2 + 2Fc2)/3
4091 reflections	(Δ/σ)max < 0.001
283 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.64 e Å−3

Experimental. No absorption correction was applied because of irregular crystal shape and low crystal quality. The crystal diffracted only very weak (less the 55% observed reflections).

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.

	x	y	z	Uiso*/Ueq
C1	0.30976 (15)	0.4803 (7)	0.3672 (4)	0.0242 (12)
C2	0.33725 (17)	0.5800 (8)	0.4143 (4)	0.0324 (14)
H2	0.3612	0.5383	0.4269	0.039*
C3	0.33038 (19)	0.7421 (8)	0.4438 (5)	0.0406 (16)
H3	0.3495	0.8094	0.4773	0.049*
C4	0.2957 (2)	0.8035 (9)	0.4240 (5)	0.0422 (17)
H4	0.2909	0.9137	0.4437	0.051*
C5	0.26812 (18)	0.7057 (9)	0.3759 (4)	0.0386 (16)
H5	0.2443	0.7486	0.3619	0.046*
C6	0.27507 (16)	0.5439 (8)	0.3476 (4)	0.0297 (13)
H6	0.2559	0.4764	0.3146	0.036*
C7	0.31548 (15)	0.3018 (8)	0.3346 (4)	0.0265 (13)
H7A	0.2945	0.2325	0.3406	0.032*
H7B	0.3163	0.3058	0.2672	0.032*
N8	0.34806 (12)	0.2177 (6)	0.3852 (3)	0.0273 (11)
C9	0.37651 (15)	0.1822 (7)	0.3379 (4)	0.0241 (12)
N10	0.38074 (14)	0.3047 (6)	0.2779 (3)	0.0326 (12)
C11	0.40604 (19)	0.2738 (9)	0.2270 (5)	0.0440 (18)
H11	0.4097	0.3582	0.1838	0.053*
C12	0.42649 (17)	0.1328 (9)	0.2326 (4)	0.0389 (16)
H12	0.4433	0.1178	0.1934	0.047*
C13	0.42200 (15)	0.0098 (8)	0.2982 (4)	0.0268 (13)
C14	0.39684 (15)	0.0377 (7)	0.3519 (4)	0.0240 (12)
H14	0.3936	−0.0418	0.3981	0.029*
C15	0.44316 (16)	−0.1512 (8)	0.3080 (4)	0.0297 (13)
H15A	0.4419	−0.1996	0.2448	0.036*
H15B	0.4319	−0.2328	0.3443	0.036*
C16	0.48232 (17)	−0.1287 (8)	0.3558 (5)	0.0341 (15)
O17	0.49559 (13)	0.0077 (6)	0.3700 (5)	0.0666 (18)
C18	0.50420 (15)	−0.2837 (8)	0.3851 (4)	0.0268 (13)
C19	0.49111 (16)	−0.4454 (8)	0.3620 (4)	0.0279 (13)
H19	0.4676	−0.4597	0.3249	0.034*
C20	0.51188 (18)	−0.5852 (8)	0.3923 (4)	0.0337 (15)
H20	0.5030	−0.6957	0.3766	0.040*
C21	0.54570 (18)	−0.5608 (8)	0.4458 (4)	0.0332 (14)
C22	0.55982 (19)	−0.4035 (9)	0.4691 (5)	0.0413 (17)
H22	0.5835	−0.3907	0.5054	0.050*
C23	0.53868 (16)	−0.2635 (8)	0.4385 (4)	0.0325 (14)
H23	0.5479	−0.1535	0.4541	0.039*
F24	0.56589 (11)	−0.6962 (5)	0.4773 (3)	0.0487 (11)
C25	0.35189 (15)	0.1753 (7)	0.4796 (3)	0.0213 (12)
O26	0.37827 (11)	0.1119 (5)	0.5264 (3)	0.0299 (10)
O27	0.32169 (10)	0.2188 (5)	0.5079 (2)	0.0260 (9)
C28	0.32262 (16)	0.2339 (8)	0.6097 (3)	0.0307 (14)
C29	0.32429 (19)	0.0591 (10)	0.6534 (4)	0.0440 (18)
H29A	0.3033	−0.0063	0.6227	0.066*
H29B	0.3245	0.0693	0.7204	0.066*
H29C	0.3462	0.0018	0.6451	0.066*
C30	0.3536 (2)	0.3456 (11)	0.6559 (5)	0.053 (2)
H30A	0.3763	0.2953	0.6482	0.080*
H30B	0.3537	0.3566	0.7228	0.080*
H30C	0.3509	0.4573	0.6265	0.080*
C31	0.28696 (18)	0.3212 (10)	0.6091 (4)	0.0443 (18)
H31A	0.2861	0.4284	0.5752	0.066*
H31B	0.2847	0.3428	0.6737	0.066*
H31C	0.2672	0.2488	0.5779	0.066*

	U11	U22	U33	U12	U13	U23
C1	0.032 (3)	0.026 (3)	0.018 (3)	−0.006 (2)	0.012 (2)	0.000 (2)
C2	0.034 (3)	0.027 (3)	0.039 (3)	−0.003 (3)	0.014 (3)	0.006 (3)
C3	0.052 (4)	0.029 (4)	0.042 (4)	−0.015 (3)	0.013 (3)	−0.005 (3)
C4	0.061 (5)	0.028 (4)	0.042 (4)	0.010 (3)	0.021 (3)	−0.005 (3)
C5	0.039 (4)	0.045 (4)	0.034 (3)	0.010 (3)	0.014 (3)	0.005 (3)
C6	0.035 (3)	0.033 (3)	0.023 (3)	0.004 (3)	0.009 (2)	0.002 (3)
C7	0.031 (3)	0.036 (3)	0.013 (2)	0.002 (3)	0.006 (2)	−0.001 (2)
N8	0.029 (3)	0.037 (3)	0.018 (2)	0.003 (2)	0.0098 (19)	0.002 (2)
C9	0.027 (3)	0.027 (3)	0.019 (2)	−0.002 (2)	0.006 (2)	0.002 (2)
N10	0.044 (3)	0.029 (3)	0.027 (3)	0.007 (2)	0.015 (2)	0.009 (2)
C11	0.054 (4)	0.046 (4)	0.040 (4)	0.013 (3)	0.031 (3)	0.021 (3)
C12	0.042 (4)	0.049 (4)	0.035 (3)	0.012 (3)	0.028 (3)	0.011 (3)
C13	0.029 (3)	0.029 (3)	0.022 (3)	−0.001 (3)	0.005 (2)	−0.003 (2)
C14	0.032 (3)	0.025 (3)	0.015 (2)	−0.003 (2)	0.006 (2)	0.001 (2)
C15	0.037 (3)	0.030 (3)	0.026 (3)	0.003 (3)	0.015 (2)	0.000 (3)
C16	0.036 (3)	0.028 (3)	0.040 (3)	0.000 (3)	0.011 (3)	0.012 (3)
O17	0.042 (3)	0.028 (3)	0.118 (5)	−0.006 (2)	−0.011 (3)	0.009 (3)
C18	0.027 (3)	0.030 (3)	0.027 (3)	−0.001 (2)	0.013 (2)	0.003 (3)
C19	0.031 (3)	0.032 (3)	0.023 (3)	0.000 (3)	0.011 (2)	−0.004 (3)
C20	0.051 (4)	0.022 (3)	0.033 (3)	0.002 (3)	0.020 (3)	−0.001 (3)
C21	0.042 (4)	0.035 (4)	0.026 (3)	0.014 (3)	0.016 (3)	0.004 (3)
C22	0.035 (4)	0.050 (5)	0.039 (4)	0.006 (3)	0.008 (3)	0.009 (3)
C23	0.037 (3)	0.030 (3)	0.033 (3)	−0.001 (3)	0.013 (3)	0.005 (3)
F24	0.062 (3)	0.040 (2)	0.045 (2)	0.022 (2)	0.015 (2)	0.0098 (19)
C25	0.031 (3)	0.021 (3)	0.014 (2)	−0.007 (2)	0.008 (2)	−0.004 (2)
O26	0.032 (2)	0.040 (3)	0.0165 (19)	0.0031 (19)	0.0030 (16)	0.0027 (18)
O27	0.033 (2)	0.032 (2)	0.0157 (18)	−0.0009 (18)	0.0114 (16)	−0.0026 (17)
C28	0.042 (3)	0.043 (4)	0.009 (2)	−0.005 (3)	0.011 (2)	−0.007 (2)
C29	0.042 (4)	0.070 (5)	0.022 (3)	−0.001 (4)	0.010 (3)	0.013 (3)
C30	0.055 (5)	0.071 (6)	0.035 (4)	−0.017 (4)	0.012 (3)	−0.023 (4)
C31	0.053 (4)	0.059 (5)	0.025 (3)	0.002 (4)	0.019 (3)	−0.003 (3)

C1—C2	1.374 (8)	O27—C28	1.484 (6)
C1—C6	1.385 (8)	C28—C30	1.515 (9)
C1—C7	1.525 (8)	C28—C29	1.521 (9)
C2—C3	1.398 (9)	C28—C31	1.522 (9)
C3—C4	1.378 (10)	C2—H2	0.9500
C4—C5	1.375 (10)	C3—H3	0.9500
C5—C6	1.391 (9)	C4—H4	0.9500
C7—N8	1.464 (7)	C5—H5	0.9500
N8—C25	1.396 (6)	C6—H6	0.9500
N8—C9	1.429 (7)	C7—H7A	0.9900
C9—N10	1.340 (7)	C7—H7B	0.9900
C9—C14	1.374 (8)	C11—H11	0.9500
N10—C11	1.356 (7)	C12—H12	0.9500
C11—C12	1.355 (9)	C14—H14	0.9500
C12—C13	1.403 (8)	C15—H15A	0.9900
C13—C14	1.376 (7)	C15—H15B	0.9900
C13—C15	1.500 (8)	C19—H19	0.9500
C15—C16	1.517 (9)	C20—H20	0.9500
C16—O17	1.194 (8)	C22—H22	0.9500
C16—C18	1.496 (8)	C23—H23	0.9500
C18—C23	1.387 (8)	C29—H29A	0.9800
C18—C19	1.391 (8)	C29—H29B	0.9800
C19—C20	1.380 (8)	C29—H29C	0.9800
C20—C21	1.371 (9)	C30—H30A	0.9800
C21—F24	1.344 (7)	C30—H30B	0.9800
C21—C22	1.373 (10)	C30—H30C	0.9800
C22—C23	1.389 (9)	C31—H31A	0.9800
C25—O26	1.199 (7)	C31—H31B	0.9800
C25—O27	1.345 (6)	C31—H31C	0.9800
C2—C1—C6	119.1 (6)	C4—C3—H3	120.00
C2—C1—C7	123.2 (5)	C3—C4—H4	120.00
C6—C1—C7	117.8 (5)	C5—C4—H4	120.00
C1—C2—C3	120.7 (6)	C4—C5—H5	120.00
C4—C3—C2	119.6 (6)	C6—C5—H5	120.00
C5—C4—C3	120.2 (6)	C1—C6—H6	120.00
C4—C5—C6	120.0 (6)	C5—C6—H6	120.00
C1—C6—C5	120.5 (6)	N8—C7—H7A	108.00
N8—C7—C1	115.3 (5)	N8—C7—H7B	108.00
C25—N8—C9	119.8 (5)	C1—C7—H7A	109.00
C25—N8—C7	120.7 (4)	C1—C7—H7B	108.00
C9—N8—C7	119.5 (4)	H7A—C7—H7B	107.00
N10—C9—C14	124.1 (5)	N10—C11—H11	117.00
N10—C9—N8	112.3 (5)	C12—C11—H11	117.00
C14—C9—N8	123.5 (5)	C11—C12—H12	121.00
C9—N10—C11	115.0 (5)	C13—C12—H12	121.00
C12—C11—N10	125.5 (6)	C9—C14—H14	120.00
C11—C12—C13	117.7 (5)	C13—C14—H14	120.00
C14—C13—C12	118.4 (5)	C13—C15—H15A	109.00
C14—C13—C15	120.5 (5)	C13—C15—H15B	109.00
C12—C13—C15	121.1 (5)	C16—C15—H15A	109.00
C9—C14—C13	119.1 (5)	C16—C15—H15B	109.00
C13—C15—C16	113.6 (5)	H15A—C15—H15B	108.00
O17—C16—C18	120.4 (6)	C18—C19—H19	120.00
O17—C16—C15	121.7 (6)	C20—C19—H19	120.00
C18—C16—C15	118.0 (5)	C19—C20—H20	121.00
C23—C18—C19	119.4 (6)	C21—C20—H20	121.00
C23—C18—C16	118.0 (6)	C21—C22—H22	121.00
C19—C18—C16	122.6 (5)	C23—C22—H22	121.00
C20—C19—C18	120.8 (6)	C18—C23—H23	120.00
C21—C20—C19	118.4 (6)	C22—C23—H23	120.00
F24—C21—C20	118.9 (6)	C28—C29—H29A	109.00
F24—C21—C22	118.4 (6)	C28—C29—H29B	109.00
C20—C21—C22	122.7 (6)	C28—C29—H29C	109.00
C21—C22—C23	118.5 (6)	H29A—C29—H29B	110.00
C18—C23—C22	120.3 (6)	H29A—C29—H29C	109.00
O26—C25—O27	126.9 (5)	H29B—C29—H29C	109.00
O26—C25—N8	124.3 (5)	C28—C30—H30A	109.00
O27—C25—N8	108.8 (5)	C28—C30—H30B	110.00
C25—O27—C28	119.0 (4)	C28—C30—H30C	109.00
O27—C28—C30	110.2 (5)	H30A—C30—H30B	109.00
O27—C28—C29	109.6 (5)	H30A—C30—H30C	109.00
C30—C28—C29	112.8 (6)	H30B—C30—H30C	109.00
O27—C28—C31	101.4 (5)	C28—C31—H31A	109.00
C30—C28—C31	110.2 (6)	C28—C31—H31B	109.00
C29—C28—C31	112.1 (5)	C28—C31—H31C	109.00
C1—C2—H2	120.00	H31A—C31—H31B	109.00
C3—C2—H2	120.00	H31A—C31—H31C	109.00
C2—C3—H3	120.00	H31B—C31—H31C	110.00
C6—C1—C2—C3	1.3 (8)	C12—C13—C15—C16	73.5 (7)
C7—C1—C2—C3	−179.1 (5)	C13—C15—C16—O17	−11.2 (9)
C1—C2—C3—C4	−1.1 (9)	C13—C15—C16—C18	168.9 (5)
C2—C3—C4—C5	0.2 (10)	O17—C16—C18—C23	7.5 (9)
C3—C4—C5—C6	0.5 (10)	C15—C16—C18—C23	−172.6 (5)
C2—C1—C6—C5	−0.6 (8)	O17—C16—C18—C19	−173.4 (7)
C7—C1—C6—C5	179.8 (5)	C15—C16—C18—C19	6.5 (8)
C4—C5—C6—C1	−0.3 (9)	C23—C18—C19—C20	0.6 (8)
C2—C1—C7—N8	22.7 (7)	C16—C18—C19—C20	−178.4 (5)
C6—C1—C7—N8	−157.7 (5)	C18—C19—C20—C21	0.0 (8)
C1—C7—N8—C25	66.5 (7)	C19—C20—C21—F24	178.7 (5)
C1—C7—N8—C9	−112.1 (5)	C19—C20—C21—C22	−0.9 (9)
C25—N8—C9—N10	−141.6 (5)	F24—C21—C22—C23	−178.5 (5)
C7—N8—C9—N10	37.1 (7)	C20—C21—C22—C23	1.1 (10)
C25—N8—C9—C14	39.1 (8)	C19—C18—C23—C22	−0.5 (9)
C7—N8—C9—C14	−142.3 (6)	C16—C18—C23—C22	178.6 (6)
C14—C9—N10—C11	2.8 (9)	C21—C22—C23—C18	−0.4 (9)
N8—C9—N10—C11	−176.5 (6)	C9—N8—C25—O26	1.4 (9)
C9—N10—C11—C12	0.0 (11)	C7—N8—C25—O26	−177.2 (6)
N10—C11—C12—C13	−1.9 (12)	C9—N8—C25—O27	−179.2 (5)
C11—C12—C13—C14	1.0 (10)	C7—N8—C25—O27	2.2 (7)
C11—C12—C13—C15	179.1 (6)	O26—C25—O27—C28	17.1 (8)
N10—C9—C14—C13	−3.7 (9)	N8—C25—O27—C28	−162.3 (5)
N8—C9—C14—C13	175.5 (5)	C25—O27—C28—C30	51.0 (7)
C12—C13—C14—C9	1.6 (8)	C25—O27—C28—C29	−73.6 (6)
C15—C13—C14—C9	−176.5 (5)	C25—O27—C28—C31	167.7 (5)
C14—C13—C15—C16	−108.4 (6)