3-(4-Methyl­phen­yl)-2-(1-pyrid­yl)-3H-benzo[4,5]furo[3,2-d]pyrimidin-4-one

In the crystal structure of the title compound, C₂₂H₂₁N₃O₂, the packing of the mol­ecules is mainly governed by inter­molecular C—H...O hydrogen bonds and π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.043
• wR factor = 0.117
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL.

3-(4-Methylphenyl)-2-(1-pyridyl)-3H-benzo[4,5]furo[3,2-d]pyrimidin-4-one

Crystal data

C22H21N3O2	F(000) = 760
Mr = 359.42	Dx = 1.295 Mg m^−3
Monoclinic, P21/n	Melting point: 485 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 14.4774 (12) Å	Cell parameters from 3667 reflections
b = 7.7044 (7) Å	θ = 2.5–27.3°
c = 16.6859 (15) Å	µ = 0.09 mm^−1
β = 97.754 (2)°	T = 292 K
V = 1844.1 (3) Å^3	Block, colorless
Z = 4	0.30 × 0.30 × 0.30 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer	2960 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.052
Graphite monochromator	θmax = 27.0°, θmin = 1.8°
φ and ω scans	h = −15→18
10894 measured reflections	k = −9→9
3995 independent reflections	l = −21→17

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)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0668P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max < 0.001
3995 reflections	Δρmax = 0.16 e Å^−3
246 parameters	Δρmin = −0.22 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: 0.023 (2)

Special details

Experimental. MS: (35 eV) m/z (%) 359 (61, M), 329 (48), 174 (100), 91 (97).

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
C1	0.98557 (10)	0.89048 (19)	0.20666 (9)	0.0568 (4)
H1A	0.9978	0.9666	0.2532	0.068*
H1B	0.9222	0.8475	0.2040	0.068*
C2	0.99595 (12)	0.9902 (2)	0.13075 (12)	0.0739 (5)
H2A	0.9526	1.0869	0.1252	0.089*
H2B	0.9812	0.9152	0.0841	0.089*
C3	1.09500 (12)	1.0577 (2)	0.13374 (11)	0.0722 (5)
H3A	1.1025	1.1123	0.0826	0.087*
H3B	1.1071	1.1443	0.1761	0.087*
C4	1.16384 (10)	0.9096 (2)	0.15014 (9)	0.0592 (4)
H4A	1.1578	0.8326	0.1037	0.071*
H4B	1.2268	0.9557	0.1576	0.071*
C5	1.14794 (9)	0.8077 (2)	0.22439 (8)	0.0528 (4)
H5A	1.1908	0.7104	0.2315	0.063*
H5B	1.1598	0.8812	0.2718	0.063*
C6	1.03427 (8)	0.61595 (16)	0.27083 (7)	0.0382 (3)
C14	0.92818 (9)	0.37540 (17)	0.29687 (8)	0.0434 (3)
C15	0.99067 (9)	0.36340 (17)	0.36989 (7)	0.0415 (3)
C16	1.06770 (8)	0.46433 (17)	0.38684 (7)	0.0393 (3)
C17	1.11222 (9)	0.41024 (17)	0.46557 (7)	0.0418 (3)
C22	1.19169 (10)	0.45896 (19)	0.51785 (8)	0.0502 (4)
H22	1.2309	0.5461	0.5037	0.060*
C21	1.21030 (10)	0.3741 (2)	0.59100 (8)	0.0566 (4)
H21	1.2628	0.4045	0.6267	0.068*
C20	1.15168 (11)	0.2437 (2)	0.61234 (9)	0.0579 (4)
H20	1.1661	0.1890	0.6621	0.069*
C19	1.07341 (11)	0.19333 (19)	0.56228 (8)	0.0539 (4)
H19	1.0345	0.1061	0.5767	0.065*
C18	1.05552 (9)	0.27903 (17)	0.48931 (8)	0.0441 (3)
C7	0.90211 (8)	0.52632 (16)	0.16850 (7)	0.0381 (3)
C12	0.93833 (9)	0.46096 (18)	0.10260 (8)	0.0441 (3)
H12	0.9974	0.4114	0.1088	0.053*
C11	0.88597 (10)	0.46976 (19)	0.02711 (8)	0.0496 (4)
H11	0.9105	0.4253	−0.0174	0.060*
C10	0.79806 (10)	0.54313 (19)	0.01613 (8)	0.0489 (3)
C9	0.76312 (9)	0.60688 (19)	0.08365 (8)	0.0489 (3)
H9	0.7041	0.6568	0.0776	0.059*
C8	0.81392 (9)	0.59794 (18)	0.15939 (8)	0.0451 (3)
H8	0.7890	0.6399	0.2042	0.054*
C13	0.74067 (12)	0.5483 (2)	−0.06649 (9)	0.0703 (5)
H13A	0.7812	0.5626	−0.1071	0.106*
H13B	0.6978	0.6438	−0.0690	0.106*
H13C	0.7066	0.4417	−0.0758	0.106*
N3	1.09122 (7)	0.59430 (14)	0.33739 (6)	0.0410 (3)
N2	0.95590 (7)	0.51259 (14)	0.24810 (6)	0.0390 (3)
N1	1.05135 (7)	0.74362 (14)	0.21580 (6)	0.0421 (3)
O1	0.86125 (7)	0.28385 (14)	0.27402 (6)	0.0606 (3)
O2	0.98035 (6)	0.24643 (12)	0.43062 (5)	0.0489 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0496 (8)	0.0436 (8)	0.0775 (10)	−0.0011 (6)	0.0097 (7)	0.0093 (7)
C2	0.0670 (10)	0.0593 (11)	0.0929 (13)	−0.0016 (8)	0.0014 (9)	0.0322 (9)
C3	0.0752 (11)	0.0598 (11)	0.0818 (12)	−0.0134 (8)	0.0118 (9)	0.0266 (9)
C4	0.0560 (9)	0.0663 (10)	0.0564 (9)	−0.0175 (8)	0.0114 (7)	0.0097 (8)
C5	0.0424 (7)	0.0638 (10)	0.0506 (8)	−0.0128 (7)	0.0009 (6)	0.0104 (7)
C6	0.0351 (6)	0.0387 (7)	0.0409 (7)	−0.0012 (5)	0.0060 (5)	0.0022 (5)
C14	0.0423 (7)	0.0450 (8)	0.0433 (7)	−0.0050 (6)	0.0068 (6)	0.0043 (6)
C15	0.0457 (7)	0.0398 (7)	0.0396 (7)	−0.0005 (6)	0.0078 (6)	0.0066 (5)
C16	0.0397 (7)	0.0395 (7)	0.0390 (7)	0.0026 (5)	0.0067 (5)	0.0021 (5)
C17	0.0446 (7)	0.0424 (7)	0.0387 (7)	0.0083 (6)	0.0070 (6)	0.0019 (5)
C22	0.0474 (8)	0.0562 (9)	0.0458 (8)	0.0058 (6)	0.0021 (6)	−0.0004 (6)
C21	0.0567 (9)	0.0680 (10)	0.0431 (8)	0.0144 (8)	−0.0008 (6)	−0.0025 (7)
C20	0.0743 (10)	0.0603 (10)	0.0390 (8)	0.0247 (8)	0.0072 (7)	0.0061 (6)
C19	0.0707 (10)	0.0460 (8)	0.0466 (8)	0.0106 (7)	0.0137 (7)	0.0081 (6)
C18	0.0499 (8)	0.0418 (7)	0.0410 (7)	0.0082 (6)	0.0071 (6)	0.0023 (6)
C7	0.0367 (6)	0.0402 (7)	0.0365 (7)	−0.0041 (5)	0.0021 (5)	0.0048 (5)
C12	0.0381 (7)	0.0493 (8)	0.0454 (8)	0.0014 (6)	0.0077 (6)	0.0036 (6)
C11	0.0525 (8)	0.0563 (9)	0.0410 (7)	−0.0042 (7)	0.0097 (6)	−0.0002 (6)
C10	0.0515 (8)	0.0482 (8)	0.0443 (8)	−0.0081 (6)	−0.0037 (6)	0.0089 (6)
C9	0.0399 (7)	0.0488 (8)	0.0556 (8)	0.0027 (6)	−0.0017 (6)	0.0060 (6)
C8	0.0392 (7)	0.0492 (8)	0.0473 (7)	0.0005 (6)	0.0071 (6)	−0.0017 (6)
C13	0.0726 (10)	0.0795 (12)	0.0527 (9)	−0.0076 (9)	−0.0140 (8)	0.0082 (8)
N3	0.0383 (6)	0.0433 (6)	0.0406 (6)	−0.0024 (5)	0.0024 (5)	0.0059 (5)
N2	0.0359 (5)	0.0426 (6)	0.0381 (6)	−0.0037 (4)	0.0032 (4)	0.0050 (4)
N1	0.0377 (6)	0.0438 (6)	0.0439 (6)	−0.0053 (5)	0.0022 (5)	0.0108 (5)
O1	0.0568 (6)	0.0664 (7)	0.0562 (6)	−0.0262 (5)	−0.0009 (5)	0.0110 (5)
O2	0.0554 (6)	0.0463 (6)	0.0449 (5)	−0.0052 (4)	0.0064 (4)	0.0104 (4)

Geometric parameters (Å, º)

C1—N1	1.4735 (18)	C17—C18	1.3930 (19)
C1—C2	1.506 (2)	C17—C22	1.3981 (18)
C1—H1A	0.9700	C22—C21	1.379 (2)
C1—H1B	0.9700	C22—H22	0.9300
C2—C3	1.520 (2)	C21—C20	1.392 (2)
C2—H2A	0.9700	C21—H21	0.9300
C2—H2B	0.9700	C20—C19	1.370 (2)
C3—C4	1.516 (2)	C20—H20	0.9300
C3—H3A	0.9700	C19—C18	1.3785 (18)
C3—H3B	0.9700	C19—H19	0.9300
C4—C5	1.5103 (19)	C18—O2	1.3852 (15)
C4—H4A	0.9700	C7—C12	1.3759 (18)
C4—H4B	0.9700	C7—C8	1.3803 (17)
C5—N1	1.4715 (16)	C7—N2	1.4501 (15)
C5—H5A	0.9700	C12—C11	1.3814 (18)
C5—H5B	0.9700	C12—H12	0.9300
C6—N3	1.3015 (15)	C11—C10	1.382 (2)
C6—N1	1.3904 (16)	C11—H11	0.9300
C6—N2	1.3961 (15)	C10—C9	1.386 (2)
C14—O1	1.2174 (15)	C10—C13	1.5111 (19)
C14—C15	1.4193 (17)	C9—C8	1.3755 (17)
C14—N2	1.4243 (16)	C9—H9	0.9300
C15—C16	1.3576 (17)	C8—H8	0.9300
C15—O2	1.3791 (15)	C13—H13A	0.9600
C16—N3	1.3694 (16)	C13—H13B	0.9600
C16—C17	1.4444 (17)	C13—H13C	0.9600
N1—C1—C2	110.02 (12)	C21—C22—H22	120.9
N1—C1—H1A	109.7	C17—C22—H22	120.9
C2—C1—H1A	109.7	C22—C21—C20	121.03 (14)
N1—C1—H1B	109.7	C22—C21—H21	119.5
C2—C1—H1B	109.7	C20—C21—H21	119.5
H1A—C1—H1B	108.2	C19—C20—C21	122.07 (13)
C1—C2—C3	110.35 (14)	C19—C20—H20	119.0
C1—C2—H2A	109.6	C21—C20—H20	119.0
C3—C2—H2A	109.6	C20—C19—C18	116.38 (15)
C1—C2—H2B	109.6	C20—C19—H19	121.8
C3—C2—H2B	109.6	C18—C19—H19	121.8
H2A—C2—H2B	108.1	C19—C18—O2	125.01 (13)
C4—C3—C2	110.04 (13)	C19—C18—C17	123.44 (13)
C4—C3—H3A	109.7	O2—C18—C17	111.55 (11)
C2—C3—H3A	109.7	C12—C7—C8	120.33 (12)
C4—C3—H3B	109.7	C12—C7—N2	119.33 (11)
C2—C3—H3B	109.7	C8—C7—N2	120.29 (11)
H3A—C3—H3B	108.2	C7—C12—C11	119.30 (12)
C5—C4—C3	111.73 (13)	C7—C12—H12	120.4
C5—C4—H4A	109.3	C11—C12—H12	120.4
C3—C4—H4A	109.3	C12—C11—C10	121.54 (13)
C5—C4—H4B	109.3	C12—C11—H11	119.2
C3—C4—H4B	109.3	C10—C11—H11	119.2
H4A—C4—H4B	107.9	C11—C10—C9	117.90 (12)
N1—C5—C4	110.02 (11)	C11—C10—C13	120.99 (14)
N1—C5—H5A	109.7	C9—C10—C13	121.08 (13)
C4—C5—H5A	109.7	C8—C9—C10	121.38 (12)
N1—C5—H5B	109.7	C8—C9—H9	119.3
C4—C5—H5B	109.7	C10—C9—H9	119.3
H5A—C5—H5B	108.2	C9—C8—C7	119.54 (12)
N3—C6—N1	120.37 (10)	C9—C8—H8	120.2
N3—C6—N2	123.83 (11)	C7—C8—H8	120.2
N1—C6—N2	115.76 (10)	C10—C13—H13A	109.5
O1—C14—C15	128.27 (12)	C10—C13—H13B	109.5
O1—C14—N2	121.65 (11)	H13A—C13—H13B	109.5
C15—C14—N2	110.04 (10)	C10—C13—H13C	109.5
C16—C15—O2	112.87 (11)	H13A—C13—H13C	109.5
C16—C15—C14	123.51 (12)	H13B—C13—H13C	109.5
O2—C15—C14	123.61 (11)	C6—N3—C16	115.31 (10)
C15—C16—N3	123.87 (11)	C6—N2—C14	123.33 (10)
C15—C16—C17	106.10 (11)	C6—N2—C7	121.57 (10)
N3—C16—C17	129.97 (12)	C14—N2—C7	114.80 (9)
C18—C17—C22	118.97 (12)	C6—N1—C5	115.10 (10)
C18—C17—C16	105.09 (11)	C6—N1—C1	116.20 (10)
C22—C17—C16	135.94 (13)	C5—N1—C1	110.18 (11)
C21—C22—C17	118.10 (14)	C15—O2—C18	104.38 (10)
N1—C1—C2—C3	−59.02 (19)	C13—C10—C9—C8	178.06 (13)
C1—C2—C3—C4	54.0 (2)	C10—C9—C8—C7	0.9 (2)
C2—C3—C4—C5	−52.98 (19)	C12—C7—C8—C9	−1.35 (19)
C3—C4—C5—N1	56.25 (18)	N2—C7—C8—C9	−178.73 (12)
O1—C14—C15—C16	174.74 (14)	N1—C6—N3—C16	−179.70 (11)
N2—C14—C15—C16	−3.14 (18)	N2—C6—N3—C16	−2.19 (17)
O1—C14—C15—O2	−4.3 (2)	C15—C16—N3—C6	−0.44 (18)
N2—C14—C15—O2	177.82 (11)	C17—C16—N3—C6	−177.13 (12)
O2—C15—C16—N3	−177.53 (11)	N3—C6—N2—C14	2.12 (19)
C14—C15—C16—N3	3.3 (2)	N1—C6—N2—C14	179.74 (11)
O2—C15—C16—C17	−0.17 (15)	N3—C6—N2—C7	−171.28 (11)
C14—C15—C16—C17	−179.30 (12)	N1—C6—N2—C7	6.34 (17)
C15—C16—C17—C18	−0.47 (14)	O1—C14—N2—C6	−177.44 (12)
N3—C16—C17—C18	176.67 (13)	C15—C14—N2—C6	0.60 (17)
C15—C16—C17—C22	−179.60 (15)	O1—C14—N2—C7	−3.63 (18)
N3—C16—C17—C22	−2.5 (2)	C15—C14—N2—C7	174.42 (10)
C18—C17—C22—C21	0.00 (19)	C12—C7—N2—C6	73.26 (15)
C16—C17—C22—C21	179.03 (14)	C8—C7—N2—C6	−109.33 (14)
C17—C22—C21—C20	0.0 (2)	C12—C7—N2—C14	−100.67 (14)
C22—C21—C20—C19	0.1 (2)	C8—C7—N2—C14	76.74 (14)
C21—C20—C19—C18	−0.1 (2)	N3—C6—N1—C5	18.96 (17)
C20—C19—C18—O2	179.72 (12)	N2—C6—N1—C5	−158.75 (11)
C20—C19—C18—C17	0.0 (2)	N3—C6—N1—C1	−111.98 (13)
C22—C17—C18—C19	0.0 (2)	N2—C6—N1—C1	70.32 (15)
C16—C17—C18—C19	−179.29 (12)	C4—C5—N1—C6	165.73 (12)
C22—C17—C18—O2	−179.73 (11)	C4—C5—N1—C1	−60.50 (16)
C16—C17—C18—O2	0.96 (14)	C2—C1—N1—C6	−164.39 (12)
C8—C7—C12—C11	0.8 (2)	C2—C1—N1—C5	62.40 (15)
N2—C7—C12—C11	178.22 (11)	C16—C15—O2—C18	0.74 (14)
C7—C12—C11—C10	0.2 (2)	C14—C15—O2—C18	179.87 (12)
C12—C11—C10—C9	−0.6 (2)	C19—C18—O2—C15	179.21 (13)
C12—C11—C10—C13	−178.62 (13)	C17—C18—O2—C15	−1.05 (13)
C11—C10—C9—C8	0.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1^i	0.93	2.51	3.2369 (16)	135

Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.