3-(4-Chloro-phen-yl)-2-(diisopropyl-amino)-1-benzofuro[3,2-d]pyrimidin-4(3H)-one.

In the mol-ecule of the title compound, C(22)H(22)ClN(3)O(2), the three fused rings of the benzofuro[3,2-d]pyrimidine system are almost coplanar. This ring system is oriented with respect to the substituted benzene ring at a dihedral angle of 79.05 (3)°. Intra-molecular C-H⋯N hydrogen bonding results in the formation of a six-membered ring. In the crystal structure, π-π stacking inter-actions involving the furan, pyrimidinone and benzene rings are present [centroid-to-centroid distances in the range 3.258 (1)-3.870 (1) Å].

Related literature

For general background, see: Bodke & Sangapure (2003 ▶); Ding et al. (2004 ▶); Janiak (2000 ▶). For a related structure, see: Liu et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C22H22ClN3O2

M = 395.88

Monoclinic,

a = 11.3713 (7) Å

b = 23.2686 (10) Å

c = 7.8405 (5) Å

β = 105.994 (1)°

V = 1994.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 295 (2) K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.958, T max = 0.979

6825 measured reflections

3919 independent reflections

3221 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.139

S = 1.14

3919 reflections

257 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.32 e Å−3

Absolute structure: Flack (1983 ▶), with 1735 Friedel pairs

Flack parameter: −0.01 (9)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL (Bruker, 2001 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807060412/hk2383sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807060412/hk2383Isup2.hkl

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

C22H22ClN3O2	F000 = 832
Mr = 395.88	Dx = 1.319 Mg m−3
Monoclinic, Cc	Mo Kα radiation λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 3139 reflections
a = 11.3713 (7) Å	θ = 2.7–26.0º
b = 23.2686 (10) Å	µ = 0.21 mm−1
c = 7.8405 (5) Å	T = 295 (2) K
β = 105.994 (1)º	Block, blue
V = 1994.2 (2) Å3	0.20 × 0.10 × 0.10 mm
Z = 4

Bruker SMART 4K CCD area-detector diffractometer	3919 independent reflections
Radiation source: fine-focus sealed tube	3221 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.043
T = 295(2) K	θmax = 27.0º
φ and ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)	h = −14→14
Tmin = 0.958, Tmax = 0.979	k = −26→29
6825 measured reflections	l = −9→9

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049	w = 1/[σ2(Fo2) + (0.059P)2 + 1.0112P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.139	(Δ/σ)max < 0.001
S = 1.14	Δρmax = 0.27 e Å−3
3919 reflections	Δρmin = −0.32 e Å−3
257 parameters	Extinction correction: none
2 restraints	Absolute structure: Flack (1983), with 1735 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.01 (9)
Secondary atom site location: difference Fourier map

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
Cl1	0.25733 (9)	0.34136 (4)	0.47013 (15)	0.0711 (3)
O1	0.6847 (2)	0.52195 (10)	0.5144 (4)	0.0575 (6)
O2	0.9123 (2)	0.56254 (9)	0.4447 (3)	0.0529 (6)
N1	0.7409 (2)	0.43085 (11)	0.4491 (4)	0.0413 (6)
N2	0.9243 (2)	0.41095 (11)	0.3704 (3)	0.0431 (6)
N3	0.7909 (2)	0.33618 (10)	0.3863 (3)	0.0409 (6)
C1	0.6217 (3)	0.41096 (13)	0.4567 (4)	0.0400 (7)
C2	0.5982 (3)	0.40193 (15)	0.6176 (4)	0.0505 (8)
H2	0.6582	0.4099	0.7224	0.061*
C3	0.4858 (3)	0.38108 (16)	0.6236 (5)	0.0541 (8)
H3	0.4694	0.3744	0.7317	0.065*
C4	0.3987 (3)	0.37038 (14)	0.4665 (5)	0.0498 (8)
C5	0.4187 (3)	0.38198 (15)	0.3056 (5)	0.0524 (8)
H5	0.3571	0.3759	0.2011	0.063*
C6	0.5316 (3)	0.40281 (15)	0.3004 (5)	0.0487 (8)
H6	0.5465	0.4112	0.1923	0.058*
C7	0.8236 (3)	0.39358 (12)	0.4014 (4)	0.0383 (6)
C8	0.9451 (3)	0.46920 (13)	0.3863 (4)	0.0435 (7)
C9	0.8700 (3)	0.50707 (13)	0.4357 (4)	0.0436 (7)
C10	0.7588 (3)	0.49109 (13)	0.4729 (4)	0.0440 (7)
C11	0.7984 (3)	0.30526 (14)	0.5543 (4)	0.0488 (8)
H11	0.7911	0.3343	0.6414	0.059*
C12	0.9206 (4)	0.2748 (2)	0.6309 (7)	0.0820 (14)
H12A	0.9271	0.2429	0.5563	0.123*
H12B	0.9252	0.2611	0.7480	0.123*
H12C	0.9864	0.3012	0.6365	0.123*
C13	0.6927 (4)	0.26389 (17)	0.5353 (6)	0.0696 (11)
H13A	0.6169	0.2838	0.4871	0.104*
H13B	0.6944	0.2485	0.6496	0.104*
H13C	0.6997	0.2331	0.4572	0.104*
C14	0.8065 (3)	0.30269 (14)	0.2347 (4)	0.0490 (8)
H14	0.7785	0.2637	0.2498	0.059*
C15	0.9372 (4)	0.2964 (2)	0.2164 (7)	0.0784 (13)
H15A	0.9655	0.3330	0.1872	0.118*
H15B	0.9372	0.2693	0.1242	0.118*
H15C	0.9905	0.2830	0.3266	0.118*
C16	0.7213 (5)	0.32524 (17)	0.0659 (5)	0.0676 (11)
H16A	0.6384	0.3222	0.0721	0.101*
H16B	0.7309	0.3031	−0.0328	0.101*
H16C	0.7401	0.3648	0.0504	0.101*
C17	1.0477 (3)	0.50223 (14)	0.3637 (4)	0.0451 (7)
C18	1.1556 (3)	0.49026 (17)	0.3222 (5)	0.0557 (9)
H18	1.1752	0.4529	0.2984	0.067*
C19	1.2333 (4)	0.53513 (19)	0.3170 (6)	0.0678 (11)
H19	1.3052	0.5281	0.2859	0.081*
C20	1.2061 (4)	0.59093 (19)	0.3576 (6)	0.0714 (12)
H20	1.2615	0.6202	0.3564	0.086*
C21	1.0995 (4)	0.60384 (17)	0.3995 (5)	0.0634 (10)
H21	1.0807	0.6412	0.4252	0.076*
C22	1.0216 (3)	0.55846 (14)	0.4014 (4)	0.0494 (8)

	U11	U22	U33	U12	U13	U23
Cl1	0.0476 (4)	0.0739 (6)	0.0964 (7)	−0.0115 (5)	0.0277 (5)	−0.0074 (6)
O1	0.0599 (15)	0.0418 (13)	0.0756 (17)	0.0038 (11)	0.0269 (13)	−0.0060 (12)
O2	0.0596 (14)	0.0342 (11)	0.0651 (15)	−0.0081 (10)	0.0176 (12)	−0.0037 (10)
N1	0.0410 (14)	0.0345 (12)	0.0480 (14)	−0.0007 (11)	0.0119 (11)	−0.0010 (11)
N2	0.0395 (13)	0.0377 (13)	0.0508 (16)	−0.0042 (11)	0.0102 (12)	−0.0008 (11)
N3	0.0441 (13)	0.0328 (12)	0.0461 (14)	−0.0028 (11)	0.0131 (11)	−0.0016 (11)
C1	0.0376 (15)	0.0366 (15)	0.0456 (17)	−0.0016 (13)	0.0109 (13)	−0.0016 (12)
C2	0.0508 (19)	0.0566 (19)	0.0427 (18)	−0.0042 (15)	0.0105 (15)	−0.0022 (15)
C3	0.053 (2)	0.065 (2)	0.0477 (18)	−0.0045 (17)	0.0206 (16)	−0.0007 (16)
C4	0.0385 (16)	0.0467 (18)	0.064 (2)	0.0016 (14)	0.0128 (15)	−0.0021 (16)
C5	0.0418 (17)	0.062 (2)	0.0478 (19)	−0.0003 (16)	0.0028 (14)	−0.0029 (16)
C6	0.0452 (17)	0.059 (2)	0.0419 (17)	0.0010 (15)	0.0120 (14)	0.0016 (14)
C7	0.0386 (15)	0.0362 (14)	0.0397 (15)	−0.0001 (12)	0.0099 (12)	0.0020 (12)
C8	0.0438 (16)	0.0359 (15)	0.0469 (17)	−0.0072 (13)	0.0058 (14)	0.0006 (13)
C9	0.0461 (16)	0.0356 (15)	0.0463 (17)	−0.0039 (13)	0.0078 (14)	−0.0018 (13)
C10	0.0466 (15)	0.0378 (15)	0.0456 (17)	0.0034 (15)	0.0091 (13)	0.0001 (14)
C11	0.0548 (18)	0.0403 (17)	0.0467 (17)	−0.0010 (14)	0.0063 (15)	0.0053 (13)
C12	0.079 (3)	0.071 (3)	0.080 (3)	0.011 (2)	−0.005 (2)	0.013 (2)
C13	0.083 (3)	0.055 (2)	0.075 (3)	−0.021 (2)	0.029 (2)	0.009 (2)
C14	0.0580 (19)	0.0370 (16)	0.0559 (19)	−0.0073 (15)	0.0220 (16)	−0.0062 (14)
C15	0.076 (3)	0.064 (3)	0.111 (4)	−0.004 (2)	0.053 (3)	−0.026 (2)
C16	0.097 (3)	0.060 (2)	0.044 (2)	−0.003 (2)	0.016 (2)	−0.0090 (16)
C17	0.0502 (17)	0.0444 (18)	0.0378 (16)	−0.0101 (14)	0.0075 (13)	0.0009 (13)
C18	0.053 (2)	0.061 (2)	0.054 (2)	−0.0102 (17)	0.0156 (16)	−0.0016 (16)
C19	0.062 (2)	0.079 (3)	0.068 (3)	−0.026 (2)	0.027 (2)	−0.005 (2)
C20	0.085 (3)	0.070 (3)	0.061 (2)	−0.038 (2)	0.023 (2)	−0.004 (2)
C21	0.084 (3)	0.051 (2)	0.054 (2)	−0.023 (2)	0.016 (2)	−0.0026 (16)
C22	0.064 (2)	0.0402 (17)	0.0408 (17)	−0.0136 (16)	0.0095 (16)	0.0018 (13)

C1—C2	1.375 (5)	C12—H12B	0.9600
C1—C6	1.377 (4)	C12—H12C	0.9600
C1—N1	1.449 (4)	C13—H13A	0.9600
C2—C3	1.380 (5)	C13—H13B	0.9600
C2—H2	0.9300	C13—H13C	0.9600
C3—C4	1.374 (5)	C14—N3	1.472 (4)
C3—H3	0.9300	C14—C16	1.504 (5)
C4—C5	1.369 (5)	C14—C15	1.539 (5)
C4—Cl1	1.751 (3)	C14—H14	0.9800
C5—C6	1.383 (5)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C7—N2	1.299 (4)	C16—H16A	0.9600
C7—N3	1.383 (4)	C16—H16B	0.9600
C7—N1	1.404 (4)	C16—H16C	0.9600
C8—C9	1.356 (5)	C17—C18	1.381 (5)
C8—N2	1.376 (4)	C17—C22	1.391 (5)
C8—C17	1.448 (5)	C18—C19	1.376 (5)
C9—O2	1.373 (4)	C18—H18	0.9300
C9—C10	1.423 (5)	C19—C20	1.392 (6)
C10—O1	1.218 (4)	C19—H19	0.9300
C10—N1	1.421 (4)	C20—C21	1.374 (6)
C11—N3	1.483 (4)	C20—H20	0.9300
C11—C13	1.515 (5)	C21—C22	1.380 (5)
C11—C12	1.528 (5)	C21—H21	0.9300
C11—H11	0.9800	C22—O2	1.379 (4)
C12—H12A	0.9600
C2—C1—C6	120.7 (3)	H13A—C13—H13C	109.5
C2—C1—N1	120.4 (3)	H13B—C13—H13C	109.5
C6—C1—N1	118.9 (3)	N3—C14—C16	109.5 (3)
C1—C2—C3	120.0 (3)	N3—C14—C15	117.4 (3)
C1—C2—H2	120.0	C16—C14—C15	110.9 (3)
C3—C2—H2	120.0	N3—C14—H14	106.1
C4—C3—C2	118.6 (3)	C16—C14—H14	106.1
C4—C3—H3	120.7	C15—C14—H14	106.1
C2—C3—H3	120.7	C14—C15—H15A	109.5
C5—C4—C3	121.9 (3)	C14—C15—H15B	109.5
C5—C4—Cl1	118.5 (3)	H15A—C15—H15B	109.5
C3—C4—Cl1	119.6 (3)	C14—C15—H15C	109.5
C4—C5—C6	119.1 (3)	H15A—C15—H15C	109.5
C4—C5—H5	120.4	H15B—C15—H15C	109.5
C6—C5—H5	120.4	C14—C16—H16A	109.5
C1—C6—C5	119.4 (3)	C14—C16—H16B	109.5
C1—C6—H6	120.3	H16A—C16—H16B	109.5
C5—C6—H6	120.3	C14—C16—H16C	109.5
N2—C7—N3	121.0 (3)	H16A—C16—H16C	109.5
N2—C7—N1	123.2 (3)	H16B—C16—H16C	109.5
N3—C7—N1	115.8 (3)	C18—C17—C22	119.6 (3)
C9—C8—N2	124.1 (3)	C18—C17—C8	136.0 (3)
C9—C8—C17	106.4 (3)	C22—C17—C8	104.3 (3)
N2—C8—C17	129.5 (3)	C19—C18—C17	118.3 (4)
C8—C9—O2	112.7 (3)	C19—C18—H18	120.9
C8—C9—C10	123.6 (3)	C17—C18—H18	120.9
O2—C9—C10	123.6 (3)	C18—C19—C20	121.1 (4)
O1—C10—N1	122.1 (3)	C18—C19—H19	119.5
O1—C10—C9	128.3 (3)	C20—C19—H19	119.5
N1—C10—C9	109.5 (3)	C21—C20—C19	121.7 (4)
N3—C11—C13	111.7 (3)	C21—C20—H20	119.2
N3—C11—C12	113.5 (4)	C19—C20—H20	119.2
C13—C11—C12	110.8 (3)	C20—C21—C22	116.5 (4)
N3—C11—H11	106.8	C20—C21—H21	121.8
C13—C11—H11	106.8	C22—C21—H21	121.8
C12—C11—H11	106.8	O2—C22—C21	125.0 (3)
C11—C12—H12A	109.5	O2—C22—C17	112.1 (3)
C11—C12—H12B	109.5	C21—C22—C17	122.9 (4)
H12A—C12—H12B	109.5	C7—N1—C10	124.2 (3)
C11—C12—H12C	109.5	C7—N1—C1	121.1 (2)
H12A—C12—H12C	109.5	C10—N1—C1	114.3 (3)
H12B—C12—H12C	109.5	C7—N2—C8	115.4 (3)
C11—C13—H13A	109.5	C7—N3—C14	119.4 (3)
C11—C13—H13B	109.5	C7—N3—C11	116.4 (2)
H13A—C13—H13B	109.5	C14—N3—C11	118.0 (2)
C11—C13—H13C	109.5	C9—O2—C22	104.5 (3)
C6—C1—C2—C3	4.1 (5)	N2—C7—N1—C10	−1.5 (5)
N1—C1—C2—C3	−177.7 (3)	N3—C7—N1—C10	179.4 (3)
C1—C2—C3—C4	−0.7 (5)	N2—C7—N1—C1	170.8 (3)
C2—C3—C4—C5	−2.7 (5)	N3—C7—N1—C1	−8.4 (4)
C2—C3—C4—Cl1	177.6 (3)	O1—C10—N1—C7	180.0 (3)
C3—C4—C5—C6	2.8 (5)	C9—C10—N1—C7	1.8 (4)
Cl1—C4—C5—C6	−177.5 (3)	O1—C10—N1—C1	7.2 (4)
C2—C1—C6—C5	−4.0 (5)	C9—C10—N1—C1	−171.0 (3)
N1—C1—C6—C5	177.8 (3)	C2—C1—N1—C7	105.9 (4)
C4—C5—C6—C1	0.6 (5)	C6—C1—N1—C7	−75.9 (4)
N2—C8—C9—O2	178.8 (3)	C2—C1—N1—C10	−81.1 (4)
C17—C8—C9—O2	1.2 (4)	C6—C1—N1—C10	97.1 (3)
N2—C8—C9—C10	−1.6 (5)	N3—C7—N2—C8	178.6 (3)
C17—C8—C9—C10	−179.3 (3)	N1—C7—N2—C8	−0.4 (4)
C8—C9—C10—O1	−178.4 (3)	C9—C8—N2—C7	2.0 (5)
O2—C9—C10—O1	1.1 (5)	C17—C8—N2—C7	179.0 (3)
C8—C9—C10—N1	−0.3 (4)	N2—C7—N3—C14	−42.8 (4)
O2—C9—C10—N1	179.2 (3)	N1—C7—N3—C14	136.3 (3)
C9—C8—C17—C18	177.2 (4)	N2—C7—N3—C11	109.0 (3)
N2—C8—C17—C18	−0.3 (6)	N1—C7—N3—C11	−71.9 (4)
C9—C8—C17—C22	−0.7 (3)	C16—C14—N3—C7	−66.1 (4)
N2—C8—C17—C22	−178.1 (3)	C15—C14—N3—C7	61.4 (4)
C22—C17—C18—C19	−1.0 (5)	C16—C14—N3—C11	142.5 (3)
C8—C17—C18—C19	−178.6 (4)	C15—C14—N3—C11	−89.9 (4)
C17—C18—C19—C20	1.9 (6)	C13—C11—N3—C7	140.8 (3)
C18—C19—C20—C21	−1.9 (7)	C12—C11—N3—C7	−93.0 (4)
C19—C20—C21—C22	0.8 (6)	C13—C11—N3—C14	−67.0 (4)
C20—C21—C22—O2	178.2 (3)	C12—C11—N3—C14	59.2 (4)
C20—C21—C22—C17	0.1 (5)	C8—C9—O2—C22	−1.2 (3)
C18—C17—C22—O2	−178.3 (3)	C10—C9—O2—C22	179.3 (3)
C8—C17—C22—O2	0.0 (3)	C21—C22—O2—C9	−177.5 (3)
C18—C17—C22—C21	0.0 (5)	C17—C22—O2—C9	0.7 (3)
C8—C17—C22—C21	178.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···N2	0.96	2.44	2.946 (5)	113

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯N2	0.96	2.44	2.946 (5)	113