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

In the title compound, C₂₁H₁₉N₃O₃, the three fused rings of the benzofuro[3,2-d]pyrimidine system are almost coplanar. The packing of the mol­ecules in the crystal structure is mainly governed by π–π and inter­molecular C—H...O hydrogen-bonding inter­actions. The C—H...O bonds link the mol­ecules into dimers.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.050
• wR factor = 0.132
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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.

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

Crystal data

C21H19N3O3	F(000) = 1520
Mr = 361.39	Dx = 1.335 Mg m^−3
Monoclinic, C2/c	Melting point: 466 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 22.8042 (16) Å	Cell parameters from 3724 reflections
b = 10.9268 (8) Å	θ = 2.2–24.5°
c = 17.7465 (12) Å	µ = 0.09 mm^−1
β = 125.562 (1)°	T = 292 K
V = 3597.3 (4) Å^3	Block, colorless
Z = 8	0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2780 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 27.0°, θmin = 2.2°
φ and ω scans	h = −29→29
14758 measured reflections	k = −13→13
3923 independent reflections	l = −22→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0618P)^2 + 0.7865P] where P = (Fo^2 + 2Fc^2)/3
3923 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

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
C1	−0.06140 (11)	1.24268 (18)	0.28387 (13)	0.0553 (5)
H1	−0.0206	1.2803	0.3342	0.066*
C2	−0.11861 (13)	1.3111 (2)	0.21474 (14)	0.0671 (6)
H2	−0.1168	1.3960	0.2188	0.081*
C3	−0.17914 (12)	1.2542 (2)	0.13892 (14)	0.0713 (6)
H3	−0.2170	1.3025	0.0935	0.086*
C4	−0.18475 (11)	1.1297 (2)	0.12903 (13)	0.0639 (6)
H4	−0.2252	1.0923	0.0781	0.077*
C5	−0.12712 (10)	1.06257 (18)	0.19876 (12)	0.0515 (5)
C6	−0.06644 (9)	1.11571 (16)	0.27612 (12)	0.0465 (4)
C7	−0.02138 (9)	1.01357 (15)	0.33176 (11)	0.0425 (4)
C8	−0.05730 (9)	0.91152 (16)	0.28412 (11)	0.0453 (4)
C9	−0.03136 (9)	0.79129 (16)	0.31572 (11)	0.0425 (4)
C10	0.07169 (9)	0.90490 (14)	0.44772 (11)	0.0396 (4)
C11	0.16069 (10)	1.00865 (16)	0.58875 (13)	0.0564 (5)
H11A	0.1214	1.0420	0.5890	0.068*
H11B	0.1744	1.0690	0.5615	0.068*
C12	0.22368 (12)	0.9813 (2)	0.68605 (14)	0.0731 (6)
H12A	0.2393	1.0562	0.7221	0.088*
H12B	0.2089	0.9243	0.7139	0.088*
C13	0.25989 (10)	0.81958 (18)	0.63821 (14)	0.0640 (6)
H13A	0.2455	0.7620	0.6663	0.077*
H13B	0.3001	0.7843	0.6410	0.077*
C14	0.19794 (9)	0.83969 (17)	0.53858 (12)	0.0517 (5)
H14A	0.2130	0.8927	0.5089	0.062*
H14B	0.1829	0.7621	0.5060	0.062*
C15	0.06837 (9)	0.65706 (15)	0.53064 (11)	0.0462 (4)
H15	0.0565	0.7187	0.5557	0.055*
C16	0.06368 (9)	0.67807 (14)	0.45087 (11)	0.0398 (4)
C17	0.08116 (9)	0.58697 (16)	0.41331 (11)	0.0479 (4)
H17	0.0783	0.6011	0.3596	0.057*
C18	0.10289 (10)	0.47465 (16)	0.45657 (12)	0.0511 (5)
H18	0.1145	0.4130	0.4311	0.061*
C19	0.10801 (9)	0.45087 (15)	0.53710 (12)	0.0473 (4)
C20	0.09072 (10)	0.54445 (16)	0.57344 (12)	0.0504 (4)
H20	0.0942	0.5312	0.6277	0.061*
C21	0.12914 (12)	0.32632 (17)	0.58111 (15)	0.0651 (6)
H21A	0.1205	0.3216	0.6280	0.098*
H21B	0.1794	0.3126	0.6087	0.098*
H21C	0.1010	0.2651	0.5348	0.098*
N1	0.03722 (7)	0.79546 (12)	0.40418 (9)	0.0408 (3)
N2	0.04476 (7)	1.01322 (12)	0.41493 (9)	0.0442 (3)
N3	0.13733 (7)	0.89601 (12)	0.53389 (9)	0.0438 (3)
O1	−0.12301 (6)	0.93638 (12)	0.20149 (8)	0.0550 (3)
O2	−0.06073 (7)	0.69479 (11)	0.27873 (8)	0.0562 (4)
O3	0.28198 (7)	0.93070 (13)	0.68882 (9)	0.0722 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0661 (12)	0.0537 (11)	0.0534 (10)	0.0163 (10)	0.0388 (10)	0.0128 (9)
C2	0.0886 (16)	0.0629 (13)	0.0627 (13)	0.0291 (12)	0.0513 (13)	0.0215 (10)
C3	0.0711 (15)	0.0834 (16)	0.0581 (13)	0.0401 (13)	0.0368 (12)	0.0308 (12)
C4	0.0513 (12)	0.0825 (16)	0.0458 (10)	0.0216 (11)	0.0213 (9)	0.0161 (10)
C5	0.0479 (11)	0.0625 (12)	0.0448 (10)	0.0150 (9)	0.0274 (9)	0.0115 (9)
C6	0.0459 (10)	0.0527 (11)	0.0453 (9)	0.0124 (8)	0.0289 (9)	0.0101 (8)
C7	0.0405 (9)	0.0456 (10)	0.0406 (9)	0.0080 (8)	0.0232 (8)	0.0076 (7)
C8	0.0352 (9)	0.0544 (11)	0.0366 (8)	0.0032 (8)	0.0153 (7)	0.0034 (8)
C9	0.0350 (9)	0.0488 (10)	0.0362 (8)	−0.0002 (8)	0.0164 (7)	−0.0024 (7)
C10	0.0357 (9)	0.0375 (9)	0.0395 (8)	0.0000 (7)	0.0183 (7)	−0.0015 (7)
C11	0.0455 (11)	0.0432 (10)	0.0574 (11)	−0.0003 (8)	0.0168 (9)	−0.0122 (8)
C12	0.0613 (14)	0.0730 (15)	0.0540 (12)	0.0004 (11)	0.0159 (11)	−0.0190 (10)
C13	0.0404 (11)	0.0579 (12)	0.0621 (12)	0.0063 (9)	0.0119 (9)	−0.0013 (10)
C14	0.0384 (10)	0.0495 (11)	0.0521 (10)	0.0016 (8)	0.0178 (8)	−0.0043 (8)
C15	0.0504 (10)	0.0421 (10)	0.0445 (9)	0.0009 (8)	0.0267 (8)	−0.0040 (7)
C16	0.0354 (9)	0.0353 (9)	0.0382 (8)	−0.0017 (7)	0.0153 (7)	−0.0025 (7)
C17	0.0524 (11)	0.0467 (10)	0.0417 (9)	0.0018 (8)	0.0257 (9)	−0.0023 (8)
C18	0.0553 (11)	0.0408 (10)	0.0526 (10)	0.0051 (8)	0.0287 (9)	−0.0058 (8)
C19	0.0418 (10)	0.0382 (9)	0.0494 (10)	−0.0008 (8)	0.0195 (8)	0.0003 (8)
C20	0.0590 (12)	0.0466 (10)	0.0438 (9)	0.0004 (9)	0.0289 (9)	0.0017 (8)
C21	0.0668 (14)	0.0457 (11)	0.0744 (14)	0.0060 (9)	0.0363 (12)	0.0094 (9)
N1	0.0361 (7)	0.0380 (8)	0.0376 (7)	0.0022 (6)	0.0154 (6)	0.0005 (6)
N2	0.0388 (8)	0.0408 (8)	0.0443 (8)	0.0055 (6)	0.0192 (7)	0.0044 (6)
N3	0.0357 (8)	0.0360 (8)	0.0428 (7)	0.0010 (6)	0.0133 (6)	−0.0044 (6)
O1	0.0419 (7)	0.0615 (8)	0.0419 (7)	0.0079 (6)	0.0132 (6)	0.0062 (6)
O2	0.0444 (7)	0.0530 (8)	0.0487 (7)	−0.0056 (6)	0.0143 (6)	−0.0101 (6)
O3	0.0413 (8)	0.0688 (9)	0.0625 (9)	−0.0009 (7)	0.0052 (7)	−0.0144 (7)

Geometric parameters (Å, º)

C1—C2	1.380 (3)	C12—O3	1.414 (3)
C1—C6	1.392 (3)	C12—H12A	0.9700
C1—H1	0.9300	C12—H12B	0.9700
C2—C3	1.394 (3)	C13—O3	1.417 (2)
C2—H2	0.9300	C13—C14	1.505 (2)
C3—C4	1.368 (3)	C13—H13A	0.9700
C3—H3	0.9300	C13—H13B	0.9700
C4—C5	1.380 (2)	C14—N3	1.470 (2)
C4—H4	0.9300	C14—H14A	0.9700
C5—O1	1.381 (2)	C14—H14B	0.9700
C5—C6	1.388 (3)	C15—C16	1.375 (2)
C6—C7	1.448 (2)	C15—C20	1.379 (2)
C7—C8	1.350 (2)	C15—H15	0.9300
C7—N2	1.365 (2)	C16—C17	1.379 (2)
C8—O1	1.3833 (19)	C16—N1	1.4541 (19)
C8—C9	1.416 (2)	C17—C18	1.378 (2)
C9—O2	1.2165 (19)	C17—H17	0.9300
C9—N1	1.434 (2)	C18—C19	1.389 (2)
C10—N2	1.3042 (19)	C18—H18	0.9300
C10—N3	1.388 (2)	C19—C20	1.383 (2)
C10—N1	1.392 (2)	C19—C21	1.502 (2)
C11—N3	1.464 (2)	C20—H20	0.9300
C11—C12	1.500 (3)	C21—H21A	0.9600
C11—H11A	0.9700	C21—H21B	0.9600
C11—H11B	0.9700	C21—H21C	0.9600
C2—C1—C6	118.1 (2)	C14—C13—H13A	109.4
C2—C1—H1	121.0	O3—C13—H13B	109.4
C6—C1—H1	121.0	C14—C13—H13B	109.4
C1—C2—C3	120.7 (2)	H13A—C13—H13B	108.0
C1—C2—H2	119.7	N3—C14—C13	109.69 (15)
C3—C2—H2	119.7	N3—C14—H14A	109.7
C4—C3—C2	122.25 (19)	C13—C14—H14A	109.7
C4—C3—H3	118.9	N3—C14—H14B	109.7
C2—C3—H3	118.9	C13—C14—H14B	109.7
C3—C4—C5	116.4 (2)	H14A—C14—H14B	108.2
C3—C4—H4	121.8	C16—C15—C20	119.90 (15)
C5—C4—H4	121.8	C16—C15—H15	120.0
C4—C5—O1	124.88 (19)	C20—C15—H15	120.0
C4—C5—C6	123.11 (19)	C15—C16—C17	120.36 (15)
O1—C5—C6	112.00 (15)	C15—C16—N1	119.46 (14)
C5—C6—C1	119.48 (16)	C17—C16—N1	120.13 (14)
C5—C6—C7	104.83 (16)	C18—C17—C16	119.01 (16)
C1—C6—C7	135.70 (17)	C18—C17—H17	120.5
C8—C7—N2	124.13 (15)	C16—C17—H17	120.5
C8—C7—C6	106.14 (16)	C17—C18—C19	121.84 (16)
N2—C7—C6	129.72 (16)	C17—C18—H18	119.1
C7—C8—O1	112.97 (15)	C19—C18—H18	119.1
C7—C8—C9	123.82 (15)	C20—C19—C18	117.73 (16)
O1—C8—C9	123.20 (15)	C20—C19—C21	121.31 (17)
O2—C9—C8	128.21 (16)	C18—C19—C21	120.93 (16)
O2—C9—N1	121.72 (15)	C15—C20—C19	121.16 (16)
C8—C9—N1	110.03 (14)	C15—C20—H20	119.4
N2—C10—N3	118.77 (14)	C19—C20—H20	119.4
N2—C10—N1	124.37 (15)	C19—C21—H21A	109.5
N3—C10—N1	116.77 (13)	C19—C21—H21B	109.5
N3—C11—C12	109.42 (15)	H21A—C21—H21B	109.5
N3—C11—H11A	109.8	C19—C21—H21C	109.5
C12—C11—H11A	109.8	H21A—C21—H21C	109.5
N3—C11—H11B	109.8	H21B—C21—H21C	109.5
C12—C11—H11B	109.8	C10—N1—C9	122.62 (13)
H11A—C11—H11B	108.2	C10—N1—C16	121.88 (13)
O3—C12—C11	111.69 (17)	C9—N1—C16	115.01 (13)
O3—C12—H12A	109.3	C10—N2—C7	114.98 (14)
C11—C12—H12A	109.3	C10—N3—C11	114.58 (13)
O3—C12—H12B	109.3	C10—N3—C14	117.88 (13)
C11—C12—H12B	109.3	C11—N3—C14	110.35 (14)
H12A—C12—H12B	107.9	C5—O1—C8	104.05 (13)
O3—C13—C14	111.36 (15)	C12—O3—C13	109.42 (15)
O3—C13—H13A	109.4
C6—C1—C2—C3	−0.8 (3)	C18—C19—C20—C15	0.7 (3)
C1—C2—C3—C4	−0.3 (3)	C21—C19—C20—C15	−177.18 (17)
C2—C3—C4—C5	0.3 (3)	N2—C10—N1—C9	2.4 (2)
C3—C4—C5—O1	179.49 (17)	N3—C10—N1—C9	178.99 (14)
C3—C4—C5—C6	0.8 (3)	N2—C10—N1—C16	−169.11 (15)
C4—C5—C6—C1	−2.0 (3)	N3—C10—N1—C16	7.4 (2)
O1—C5—C6—C1	179.21 (15)	O2—C9—N1—C10	−179.94 (15)
C4—C5—C6—C7	178.22 (16)	C8—C9—N1—C10	−2.0 (2)
O1—C5—C6—C7	−0.61 (19)	O2—C9—N1—C16	−7.9 (2)
C2—C1—C6—C5	1.9 (3)	C8—C9—N1—C16	170.11 (13)
C2—C1—C6—C7	−178.35 (18)	C15—C16—N1—C10	60.1 (2)
C5—C6—C7—C8	0.67 (18)	C17—C16—N1—C10	−122.48 (17)
C1—C6—C7—C8	−179.11 (19)	C15—C16—N1—C9	−112.02 (17)
C5—C6—C7—N2	179.65 (16)	C17—C16—N1—C9	65.4 (2)
C1—C6—C7—N2	−0.1 (3)	N3—C10—N2—C7	−177.21 (14)
N2—C7—C8—O1	−179.58 (14)	N1—C10—N2—C7	−0.7 (2)
C6—C7—C8—O1	−0.52 (19)	C8—C7—N2—C10	−1.2 (2)
N2—C7—C8—C9	1.5 (3)	C6—C7—N2—C10	180.00 (16)
C6—C7—C8—C9	−179.48 (16)	N2—C10—N3—C11	14.5 (2)
C7—C8—C9—O2	177.97 (17)	N1—C10—N3—C11	−162.29 (15)
O1—C8—C9—O2	−0.9 (3)	N2—C10—N3—C14	−117.96 (17)
C7—C8—C9—N1	0.2 (2)	N1—C10—N3—C14	65.3 (2)
O1—C8—C9—N1	−178.69 (14)	C12—C11—N3—C10	168.81 (17)
N3—C11—C12—O3	58.5 (2)	C12—C11—N3—C14	−55.3 (2)
O3—C13—C14—N3	−57.6 (2)	C13—C14—N3—C10	−170.65 (15)
C20—C15—C16—C17	0.1 (3)	C13—C14—N3—C11	55.07 (19)
C20—C15—C16—N1	177.48 (15)	C4—C5—O1—C8	−178.50 (17)
C15—C16—C17—C18	0.4 (3)	C6—C5—O1—C8	0.31 (18)
N1—C16—C17—C18	−176.99 (15)	C7—C8—O1—C5	0.15 (19)
C16—C17—C18—C19	−0.3 (3)	C9—C8—O1—C5	179.12 (16)
C17—C18—C19—C20	−0.2 (3)	C11—C12—O3—C13	−60.5 (2)
C17—C18—C19—C21	177.68 (17)	C14—C13—O3—C12	59.9 (2)
C16—C15—C20—C19	−0.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2^i	0.93	2.47	3.372 (2)	164

Symmetry code: (i) −x, y, −z+1/2.