Ethyl 2-oxo-3-(3-phthalimidoprop-yl)-2,3-dihydro-1H-1,3-benzimidazole-1-carboxyl-ate.

In the title compound, C21H19N3O5, the phthalimide and benzamidazole ring systems are linked by a propyl chain. The benzamidazole unit also carries an eth-oxy-carbonyl substit-uent. The phthalimido and benzimidazole ring systems are essentially planar, the maximum deviations from their mean planes being 0.008 (2) and 0.020 (2) Å, respectively. The two ring systems are almost orthogonal to one another, making a dihedral angle of 82.37 (8)°. In the crystal, C-H⋯O hydrogen bonds and C-H⋯π contacts stack the mol-ecules along the b axis.

Related literature

For the pharmacological and biochemical properties of benzamidazoles, see: Gravatt et al. (1994 ▶); Horton et al. (2003 ▶); Kim et al. (1996 ▶); Roth et al. (1997 ▶); Zarrinmayeh et al. (1998 ▶); Spasov et al. (1999 ▶). For their use as inter­mediates in many organic reactions, see: Bai et al. (2001 ▶); Hasegawa et al. (1999 ▶). For their use as ligands to transition metals, see: Bouwman et al. (1990 ▶). For a related structure, see: Belaziz et al. (2013 ▶).

Experimental

Crystal data

C21H19N3O5

M = 393.39

Triclinic,

a = 5.2850 (7) Å

b = 10.6663 (12) Å

c = 16.505 (2) Å

α = 86.454 (7)°

β = 83.424 (8)°

γ = 89.376 (7)°

V = 922.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.41 × 0.32 × 0.21 mm

Data collection

Bruker X8 APEXII area-detector diffractometer

19211 measured reflections

3384 independent reflections

2405 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.145

S = 1.04

3384 reflections

263 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813008325/sj5310sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008325/sj5310Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008325/sj5310Isup3.cml

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

C21H19N3O5	Z = 2
Mr = 393.39	F(000) = 412
Triclinic, P1	Dx = 1.416 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.2850 (7) Å	Cell parameters from 3384 reflections
b = 10.6663 (12) Å	θ = 1.2–25.4°
c = 16.505 (2) Å	µ = 0.10 mm−1
α = 86.454 (7)°	T = 296 K
β = 83.424 (8)°	Block, colourless
γ = 89.376 (7)°	0.41 × 0.32 × 0.21 mm
V = 922.5 (2) Å3

Bruker X8 APEXII area-detector diffractometer	2405 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 25.4°, θmin = 1.2°
φ and ω scans	h = −6→6
19211 measured reflections	k = −12→12
3384 independent reflections	l = −19→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H-atom parameters constrained
wR(F2) = 0.145	w = 1/[σ2(Fo2) + (0.0621P)2 + 0.3912P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3384 reflections	Δρmax = 0.61 e Å−3
263 parameters	Δρmin = −0.38 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (3)

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
C5	−0.2365 (7)	0.1185 (3)	−0.2119 (2)	0.0843 (10)
H5	−0.3437	0.0758	−0.2415	0.101*
C21	−0.3239 (7)	0.4211 (3)	0.6009 (2)	0.0908 (10)
H21B	−0.4152	0.4241	0.6545	0.136*
H21A	−0.3239	0.5030	0.5734	0.136*
H21C	−0.1516	0.3946	0.6055	0.136*
N2	0.2008 (4)	0.34071 (17)	0.26388 (11)	0.0470 (5)
N3	0.0386 (4)	0.26952 (18)	0.38811 (11)	0.0523 (5)
N1	0.1200 (4)	0.24930 (18)	0.00965 (11)	0.0510 (5)
C12	0.3548 (4)	0.2414 (2)	0.28783 (13)	0.0443 (5)
C2	0.0804 (5)	0.2455 (2)	−0.12718 (14)	0.0500 (6)
O3	−0.1555 (4)	0.44303 (17)	0.32188 (11)	0.0689 (5)
C17	0.2542 (4)	0.1945 (2)	0.36512 (13)	0.0469 (6)
C10	0.1307 (5)	0.3982 (2)	0.11910 (14)	0.0507 (6)
H10A	−0.0524	0.3959	0.1337	0.061*
H10B	0.1674	0.4644	0.0765	0.061*
C7	−0.1005 (4)	0.1658 (2)	−0.08645 (15)	0.0506 (6)
O5	−0.2966 (4)	0.3344 (2)	0.47224 (11)	0.0810 (6)
O4	−0.0387 (4)	0.1848 (2)	0.51828 (11)	0.0833 (6)
C8	−0.0771 (5)	0.1668 (2)	0.00225 (15)	0.0522 (6)
O2	−0.1989 (4)	0.10977 (18)	0.05886 (12)	0.0750 (6)
C18	0.0058 (5)	0.3619 (2)	0.32393 (14)	0.0520 (6)
C1	0.2254 (5)	0.3000 (2)	−0.06647 (15)	0.0526 (6)
C11	0.2575 (5)	0.4292 (2)	0.19332 (13)	0.0504 (6)
H11A	0.4404	0.4313	0.1785	0.060*
H11B	0.2036	0.5125	0.2088	0.060*
C16	0.3660 (5)	0.0934 (2)	0.40379 (15)	0.0582 (7)
H16	0.2968	0.0601	0.4548	0.070*
O1	0.4014 (4)	0.37287 (19)	−0.07584 (12)	0.0772 (6)
C19	−0.0985 (6)	0.2572 (3)	0.46572 (16)	0.0624 (7)
C9	0.2183 (5)	0.2738 (2)	0.08601 (15)	0.0572 (6)
H9A	0.4030	0.2727	0.0774	0.069*
H9B	0.1645	0.2068	0.1265	0.069*
C14	0.6862 (5)	0.0914 (2)	0.28759 (17)	0.0619 (7)
H14	0.8350	0.0565	0.2626	0.074*
C13	0.5705 (5)	0.1904 (2)	0.24783 (15)	0.0534 (6)
H13	0.6362	0.2215	0.1959	0.064*
C3	0.1069 (6)	0.2628 (3)	−0.21100 (16)	0.0692 (8)
H3	0.2295	0.3166	−0.2386	0.083*
C15	0.5848 (5)	0.0436 (2)	0.36365 (17)	0.0646 (7)
H15	0.6653	−0.0238	0.3886	0.078*
C6	−0.2639 (5)	0.1006 (3)	−0.1276 (2)	0.0709 (8)
H6	−0.3871	0.0471	−0.1000	0.085*
C4	−0.0562 (7)	0.1970 (3)	−0.25264 (19)	0.0814 (10)
H4	−0.0426	0.2064	−0.3094	0.098*
C20	−0.4465 (6)	0.3326 (4)	0.55469 (18)	0.0879 (10)
H20A	−0.6216	0.3576	0.5500	0.105*
H20B	−0.4458	0.2490	0.5814	0.105*

	U11	U22	U33	U12	U13	U23
C5	0.092 (2)	0.084 (2)	0.088 (2)	0.0255 (19)	−0.044 (2)	−0.0318 (19)
C21	0.089 (2)	0.099 (2)	0.083 (2)	0.0039 (19)	−0.0046 (18)	−0.0065 (19)
N2	0.0562 (11)	0.0444 (10)	0.0386 (10)	−0.0012 (9)	0.0001 (9)	0.0030 (8)
N3	0.0660 (13)	0.0537 (12)	0.0354 (10)	−0.0038 (10)	0.0003 (9)	0.0002 (9)
N1	0.0568 (12)	0.0541 (11)	0.0418 (11)	0.0000 (9)	−0.0056 (9)	−0.0010 (9)
C12	0.0512 (13)	0.0402 (12)	0.0427 (12)	−0.0087 (10)	−0.0106 (10)	−0.0005 (9)
C2	0.0597 (15)	0.0449 (12)	0.0456 (13)	0.0100 (11)	−0.0090 (11)	−0.0001 (10)
O3	0.0777 (13)	0.0662 (12)	0.0581 (11)	0.0161 (10)	0.0075 (9)	0.0029 (9)
C17	0.0591 (14)	0.0431 (12)	0.0399 (12)	−0.0089 (11)	−0.0103 (10)	−0.0029 (10)
C10	0.0571 (14)	0.0498 (13)	0.0427 (13)	0.0048 (11)	−0.0006 (11)	0.0054 (10)
C7	0.0503 (13)	0.0463 (13)	0.0561 (14)	0.0097 (11)	−0.0084 (11)	−0.0066 (11)
O5	0.0870 (15)	0.1053 (16)	0.0465 (11)	0.0083 (13)	0.0089 (10)	−0.0017 (10)
O4	0.1133 (17)	0.0836 (14)	0.0472 (11)	0.0033 (12)	0.0056 (11)	0.0141 (10)
C8	0.0491 (14)	0.0495 (13)	0.0551 (15)	0.0054 (11)	0.0044 (11)	−0.0007 (11)
O2	0.0758 (13)	0.0763 (13)	0.0664 (12)	−0.0086 (10)	0.0165 (10)	0.0047 (10)
C18	0.0630 (15)	0.0501 (13)	0.0418 (13)	−0.0022 (12)	−0.0014 (11)	−0.0025 (10)
C1	0.0587 (15)	0.0473 (13)	0.0498 (14)	0.0003 (12)	−0.0006 (11)	0.0021 (11)
C11	0.0627 (15)	0.0427 (12)	0.0434 (13)	−0.0030 (11)	0.0013 (11)	0.0038 (10)
C16	0.0827 (19)	0.0492 (14)	0.0447 (13)	−0.0104 (13)	−0.0186 (13)	0.0035 (11)
O1	0.0802 (13)	0.0746 (13)	0.0742 (13)	−0.0261 (11)	0.0018 (10)	0.0006 (10)
C19	0.0784 (19)	0.0636 (16)	0.0436 (14)	−0.0090 (14)	−0.0001 (13)	−0.0002 (13)
C9	0.0647 (16)	0.0600 (15)	0.0483 (14)	0.0081 (12)	−0.0134 (12)	−0.0038 (11)
C14	0.0581 (16)	0.0607 (16)	0.0689 (18)	0.0043 (12)	−0.0151 (13)	−0.0067 (13)
C13	0.0532 (14)	0.0545 (14)	0.0521 (14)	−0.0036 (11)	−0.0048 (11)	−0.0010 (11)
C3	0.090 (2)	0.0646 (17)	0.0515 (16)	0.0143 (15)	−0.0071 (15)	0.0041 (13)
C15	0.0774 (19)	0.0518 (15)	0.0684 (18)	0.0036 (13)	−0.0271 (15)	−0.0007 (13)
C6	0.0623 (17)	0.0625 (17)	0.091 (2)	0.0050 (13)	−0.0164 (15)	−0.0170 (15)
C4	0.114 (3)	0.079 (2)	0.0558 (17)	0.031 (2)	−0.0304 (18)	−0.0124 (16)
C20	0.087 (2)	0.113 (3)	0.0630 (19)	−0.005 (2)	0.0007 (17)	−0.0131 (18)

C5—C4	1.365 (5)	C10—H10B	0.9700
C5—C6	1.383 (4)	C7—C6	1.377 (4)
C5—H5	0.9300	C7—C8	1.484 (3)
C21—C20	1.452 (4)	O5—C19	1.324 (3)
C21—H21B	0.9600	O5—C20	1.493 (3)
C21—H21A	0.9600	O4—C19	1.193 (3)
C21—H21C	0.9600	C8—O2	1.208 (3)
N2—C18	1.373 (3)	C1—O1	1.209 (3)
N2—C12	1.394 (3)	C11—H11A	0.9700
N2—C11	1.458 (3)	C11—H11B	0.9700
N3—C19	1.397 (3)	C16—C15	1.383 (4)
N3—C17	1.415 (3)	C16—H16	0.9300
N3—C18	1.426 (3)	C9—H9A	0.9700
N1—C8	1.391 (3)	C9—H9B	0.9700
N1—C1	1.394 (3)	C14—C15	1.377 (4)
N1—C9	1.456 (3)	C14—C13	1.383 (3)
C12—C13	1.374 (3)	C14—H14	0.9300
C12—C17	1.390 (3)	C13—H13	0.9300
C2—C7	1.374 (3)	C3—C4	1.384 (4)
C2—C3	1.376 (3)	C3—H3	0.9300
C2—C1	1.478 (3)	C15—H15	0.9300
O3—C18	1.209 (3)	C6—H6	0.9300
C17—C16	1.381 (3)	C4—H4	0.9300
C10—C9	1.514 (3)	C20—H20A	0.9700
C10—C11	1.517 (3)	C20—H20B	0.9700
C10—H10A	0.9700
C4—C5—C6	121.8 (3)	O1—C1—C2	130.4 (2)
C4—C5—H5	119.1	N1—C1—C2	106.0 (2)
C6—C5—H5	119.1	N2—C11—C10	114.17 (19)
C20—C21—H21B	109.5	N2—C11—H11A	108.7
C20—C21—H21A	109.5	C10—C11—H11A	108.7
H21B—C21—H21A	109.5	N2—C11—H11B	108.7
C20—C21—H21C	109.5	C10—C11—H11B	108.7
H21B—C21—H21C	109.5	H11A—C11—H11B	107.6
H21A—C21—H21C	109.5	C17—C16—C15	117.4 (2)
C18—N2—C12	111.02 (18)	C17—C16—H16	121.3
C18—N2—C11	121.51 (19)	C15—C16—H16	121.3
C12—N2—C11	126.41 (19)	O4—C19—O5	125.7 (3)
C19—N3—C17	122.5 (2)	O4—C19—N3	122.5 (3)
C19—N3—C18	127.8 (2)	O5—C19—N3	111.7 (2)
C17—N3—C18	109.47 (18)	N1—C9—C10	113.48 (19)
C8—N1—C1	111.4 (2)	N1—C9—H9A	108.9
C8—N1—C9	125.0 (2)	C10—C9—H9A	108.9
C1—N1—C9	123.5 (2)	N1—C9—H9B	108.9
C13—C12—C17	121.4 (2)	C10—C9—H9B	108.9
C13—C12—N2	130.5 (2)	H9A—C9—H9B	107.7
C17—C12—N2	108.1 (2)	C15—C14—C13	121.0 (3)
C7—C2—C3	121.3 (3)	C15—C14—H14	119.5
C7—C2—C1	108.5 (2)	C13—C14—H14	119.5
C3—C2—C1	130.2 (3)	C12—C13—C14	117.6 (2)
C16—C17—C12	120.9 (2)	C12—C13—H13	121.2
C16—C17—N3	132.8 (2)	C14—C13—H13	121.2
C12—C17—N3	106.32 (19)	C2—C3—C4	117.4 (3)
C9—C10—C11	112.89 (19)	C2—C3—H3	121.3
C9—C10—H10A	109.0	C4—C3—H3	121.3
C11—C10—H10A	109.0	C14—C15—C16	121.6 (2)
C9—C10—H10B	109.0	C14—C15—H15	119.2
C11—C10—H10B	109.0	C16—C15—H15	119.2
H10A—C10—H10B	107.8	C7—C6—C5	116.9 (3)
C2—C7—C6	121.6 (3)	C7—C6—H6	121.5
C2—C7—C8	107.9 (2)	C5—C6—H6	121.5
C6—C7—C8	130.5 (3)	C5—C4—C3	121.1 (3)
C19—O5—C20	115.4 (2)	C5—C4—H4	119.4
O2—C8—N1	124.7 (2)	C3—C4—H4	119.4
O2—C8—C7	129.2 (2)	C21—C20—O5	106.3 (3)
N1—C8—C7	106.2 (2)	C21—C20—H20A	110.5
O3—C18—N2	126.6 (2)	O5—C20—H20A	110.5
O3—C18—N3	128.4 (2)	C21—C20—H20B	110.5
N2—C18—N3	105.1 (2)	O5—C20—H20B	110.5
O1—C1—N1	123.6 (2)	H20A—C20—H20B	108.7

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O2i	0.97	2.72	3.523 (3)	141
C13—H13···O2i	0.93	2.67	3.375 (3)	133
C21—H21B···O3ii	0.96	2.67	3.261 (4)	121
C11—H11A···O1iii	0.97	2.68	3.201 (3)	114
C5—H5···Cg1iv	0.93	2.91	3.750 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C12–C17 ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O2i	0.97	2.72	3.523 (3)	141
C13—H13⋯O2i	0.93	2.67	3.375 (3)	133
C21—H21B⋯O3ii	0.96	2.67	3.261 (4)	121
C11—H11A⋯O1iii	0.97	2.68	3.201 (3)	114
C5—H5⋯Cg1iv	0.93	2.91	3.750 (3)	151

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .