Ethyl 2-(1,3-benzodioxol-5-yl)-1-[3-(1H-imidazol-1-yl)prop-yl]-1H-benzimidazole-5-carboxyl-ate.

In the title compound, C(23)H(22)N(4)O(4), the essentially planar [maximum deviation = 0.022 (1) Å] benzimidazole ring system forms dihedral angles of 86.16 (7) and 37.38 (6)°, respectively, with the imidazole and benzene rings. The dioxolane ring adopts an envelope conformation with the methyl-ene C atom at the flap. In the crystal, C-H⋯O and C-H⋯N inter-actions link the mol-ecules into a ribbon along the a axis. The crystal packing is further stabilized by weak π-π stacking inter-actions [centroid-centroid distances = 3.5954 (8) and 3.7134 (8) Å] and C-H⋯π inter-actions.

Related literature

For the biological activity of benzimidazole derivatives, see: Grassmann et al. (2002 ▶); Demirayak et al. (2002 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For a related structure, see: Yoon et al. (2011 ▶).

Experimental

Crystal data

C23H22N4O4

M = 418.45

Orthorhombic,

a = 15.8554 (2) Å

b = 15.3988 (2) Å

c = 16.2292 (2) Å

V = 3962.43 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.42 × 0.28 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.960, T max = 0.981

39067 measured reflections

5782 independent reflections

4429 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.126

S = 1.06

5782 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811054572/is5032sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054572/is5032Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811054572/is5032Isup3.cml

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

C23H22N4O4	F(000) = 1760
Mr = 418.45	Dx = 1.403 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7948 reflections
a = 15.8554 (2) Å	θ = 2.2–29.9°
b = 15.3988 (2) Å	µ = 0.10 mm−1
c = 16.2292 (2) Å	T = 100 K
V = 3962.43 (9) Å3	Block, yellow
Z = 8	0.42 × 0.28 × 0.20 mm

Bruker SMART APEXII CCD area-detector diffractometer	5782 independent reflections
Radiation source: fine-focus sealed tube	4429 reflections with I > 2σ(I)
graphite	Rint = 0.054
φ and ω scans	θmax = 30.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −22→22
Tmin = 0.960, Tmax = 0.981	k = −17→21
39067 measured reflections	l = −22→22

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0539P)2 + 1.7654P] where P = (Fo2 + 2Fc2)/3
5782 reflections	(Δ/σ)max = 0.001
280 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.21824 (6)	0.91984 (8)	0.49482 (7)	0.0282 (3)
O2	0.25425 (7)	0.90679 (7)	0.62843 (7)	0.0271 (2)
O3	0.89060 (6)	0.92843 (7)	0.71394 (6)	0.0239 (2)
O4	0.98149 (6)	0.84912 (7)	0.63028 (7)	0.0263 (2)
N1	0.58208 (7)	0.86631 (8)	0.59836 (7)	0.0194 (2)
N2	0.61041 (7)	0.87485 (8)	0.46195 (7)	0.0187 (2)
N3	0.79424 (8)	0.84083 (8)	0.26915 (7)	0.0225 (3)
N4	0.91848 (9)	0.89721 (9)	0.30370 (9)	0.0296 (3)
C1	0.50764 (8)	0.87928 (9)	0.55479 (8)	0.0182 (3)
C2	0.42516 (8)	0.88928 (9)	0.58316 (9)	0.0190 (3)
H2A	0.4125	0.8865	0.6403	0.023*
C3	0.36188 (8)	0.90350 (9)	0.52518 (9)	0.0191 (3)
C4	0.38044 (9)	0.90927 (9)	0.44011 (9)	0.0202 (3)
H4A	0.3360	0.9195	0.4021	0.024*
C5	0.46187 (9)	0.90041 (9)	0.41113 (8)	0.0200 (3)
H5A	0.4747	0.9048	0.3541	0.024*
C6	0.52433 (8)	0.88464 (9)	0.46988 (8)	0.0182 (3)
C7	0.64171 (9)	0.86485 (9)	0.54132 (9)	0.0184 (3)
C8	0.73210 (8)	0.85749 (9)	0.56059 (8)	0.0182 (3)
C9	0.78806 (9)	0.81167 (10)	0.51027 (9)	0.0212 (3)
H9A	0.7671	0.7838	0.4622	0.025*
C10	0.87401 (9)	0.80575 (10)	0.52865 (9)	0.0221 (3)
H10A	0.9118	0.7742	0.4944	0.027*
C11	0.90130 (8)	0.84735 (9)	0.59813 (9)	0.0196 (3)
C12	0.84659 (9)	0.89351 (9)	0.64855 (8)	0.0185 (3)
C13	0.76188 (9)	0.89913 (9)	0.63259 (8)	0.0195 (3)
H13A	0.7248	0.9297	0.6683	0.023*
C14	0.27411 (9)	0.91028 (9)	0.55607 (9)	0.0203 (3)
C15	0.13033 (9)	0.92811 (14)	0.51877 (11)	0.0346 (4)
H15A	0.1172	0.9892	0.5326	0.042*
H15B	0.1185	0.8917	0.5677	0.042*
C16	0.07810 (10)	0.89887 (12)	0.44744 (11)	0.0332 (4)
H16A	0.0182	0.9039	0.4615	0.050*
H16B	0.0914	0.8382	0.4346	0.050*
H16C	0.0904	0.9353	0.3994	0.050*
C17	0.65550 (9)	0.89081 (10)	0.38489 (8)	0.0205 (3)
H17A	0.7154	0.9030	0.3976	0.025*
H17B	0.6316	0.9431	0.3582	0.025*
C18	0.65105 (9)	0.81489 (10)	0.32436 (9)	0.0239 (3)
H18A	0.6717	0.7613	0.3515	0.029*
H18B	0.5918	0.8053	0.3075	0.029*
C19	0.70487 (10)	0.83430 (11)	0.24854 (9)	0.0270 (3)
H19A	0.6968	0.7876	0.2074	0.032*
H19B	0.6859	0.8896	0.2235	0.032*
C20	0.84682 (9)	0.77241 (10)	0.28605 (9)	0.0241 (3)
H20A	0.8332	0.7124	0.2839	0.029*
C21	0.92254 (10)	0.80816 (10)	0.30661 (9)	0.0252 (3)
H21A	0.9715	0.7759	0.3210	0.030*
C22	0.84051 (10)	0.91387 (10)	0.28135 (9)	0.0273 (3)
H22A	0.8188	0.9709	0.2745	0.033*
C23	0.97877 (9)	0.91055 (11)	0.69681 (9)	0.0248 (3)
H23A	1.0084	0.9647	0.6811	0.030*
H23B	1.0066	0.8861	0.7463	0.030*

	U11	U22	U33	U12	U13	U23
O1	0.0160 (5)	0.0441 (7)	0.0245 (5)	0.0033 (4)	0.0008 (4)	0.0050 (5)
O2	0.0243 (5)	0.0349 (6)	0.0220 (5)	0.0040 (5)	0.0030 (4)	0.0006 (5)
O3	0.0217 (5)	0.0320 (6)	0.0181 (5)	−0.0026 (4)	−0.0009 (4)	−0.0034 (4)
O4	0.0179 (5)	0.0356 (6)	0.0253 (5)	−0.0013 (4)	−0.0006 (4)	−0.0055 (5)
N1	0.0199 (5)	0.0202 (6)	0.0182 (6)	0.0012 (4)	−0.0008 (4)	−0.0003 (4)
N2	0.0174 (5)	0.0210 (6)	0.0178 (5)	0.0014 (4)	0.0011 (4)	−0.0003 (4)
N3	0.0263 (6)	0.0261 (7)	0.0151 (5)	0.0031 (5)	0.0024 (4)	−0.0009 (5)
N4	0.0328 (7)	0.0283 (7)	0.0276 (7)	−0.0050 (6)	0.0045 (5)	0.0027 (6)
C1	0.0212 (6)	0.0171 (7)	0.0163 (6)	0.0011 (5)	−0.0008 (5)	0.0002 (5)
C2	0.0213 (6)	0.0182 (7)	0.0174 (6)	0.0007 (5)	0.0011 (5)	−0.0007 (5)
C3	0.0193 (6)	0.0179 (7)	0.0199 (7)	0.0012 (5)	0.0011 (5)	−0.0007 (5)
C4	0.0199 (6)	0.0210 (7)	0.0196 (7)	0.0010 (5)	−0.0018 (5)	0.0015 (5)
C5	0.0223 (7)	0.0218 (7)	0.0160 (6)	0.0009 (5)	0.0003 (5)	0.0005 (5)
C6	0.0183 (6)	0.0173 (7)	0.0188 (6)	0.0002 (5)	0.0014 (5)	−0.0009 (5)
C7	0.0209 (6)	0.0160 (7)	0.0184 (6)	0.0010 (5)	−0.0009 (5)	−0.0008 (5)
C8	0.0201 (6)	0.0170 (7)	0.0176 (6)	0.0002 (5)	−0.0010 (5)	0.0020 (5)
C9	0.0220 (6)	0.0197 (7)	0.0220 (7)	0.0011 (5)	−0.0014 (5)	−0.0037 (5)
C10	0.0211 (6)	0.0217 (7)	0.0236 (7)	0.0020 (5)	0.0025 (5)	−0.0027 (6)
C11	0.0172 (6)	0.0205 (7)	0.0212 (7)	−0.0015 (5)	0.0010 (5)	0.0034 (5)
C12	0.0229 (6)	0.0180 (7)	0.0146 (6)	−0.0022 (5)	0.0000 (5)	0.0015 (5)
C13	0.0217 (6)	0.0198 (7)	0.0171 (6)	0.0019 (5)	0.0010 (5)	−0.0002 (5)
C14	0.0206 (6)	0.0172 (7)	0.0230 (7)	0.0010 (5)	0.0000 (5)	0.0002 (5)
C15	0.0174 (7)	0.0565 (12)	0.0300 (9)	0.0047 (7)	0.0029 (6)	0.0029 (8)
C16	0.0223 (7)	0.0453 (10)	0.0320 (9)	−0.0005 (7)	−0.0004 (6)	0.0054 (7)
C17	0.0214 (6)	0.0228 (7)	0.0173 (6)	0.0009 (5)	0.0023 (5)	0.0007 (5)
C18	0.0228 (7)	0.0275 (8)	0.0215 (7)	0.0005 (6)	−0.0025 (5)	−0.0044 (6)
C19	0.0279 (7)	0.0372 (9)	0.0159 (6)	0.0055 (6)	−0.0021 (5)	−0.0030 (6)
C20	0.0296 (7)	0.0215 (7)	0.0213 (7)	0.0032 (6)	0.0015 (6)	−0.0030 (6)
C21	0.0272 (7)	0.0266 (8)	0.0219 (7)	0.0011 (6)	0.0032 (6)	−0.0003 (6)
C22	0.0381 (8)	0.0224 (8)	0.0215 (7)	0.0003 (6)	0.0041 (6)	0.0029 (6)
C23	0.0207 (6)	0.0318 (8)	0.0219 (7)	−0.0028 (6)	−0.0013 (5)	−0.0010 (6)

O1—C14	1.3396 (17)	C8—C13	1.4140 (19)
O1—C15	1.4526 (18)	C9—C10	1.3981 (19)
O2—C14	1.2170 (18)	C9—H9A	0.9500
O3—C12	1.3792 (16)	C10—C11	1.367 (2)
O3—C23	1.4516 (18)	C10—H10A	0.9500
O4—C11	1.3745 (17)	C11—C12	1.3883 (19)
O4—C23	1.4361 (19)	C12—C13	1.3707 (19)
N1—C7	1.3233 (18)	C13—H13A	0.9500
N1—C1	1.3902 (17)	C15—C16	1.493 (2)
N2—C6	1.3793 (17)	C15—H15A	0.9900
N2—C7	1.3889 (18)	C15—H15B	0.9900
N2—C17	1.4613 (17)	C16—H16A	0.9800
N3—C22	1.357 (2)	C16—H16B	0.9800
N3—C20	1.3713 (19)	C16—H16C	0.9800
N3—C19	1.460 (2)	C17—C18	1.529 (2)
N4—C22	1.314 (2)	C17—H17A	0.9900
N4—C21	1.374 (2)	C17—H17B	0.9900
C1—C2	1.3950 (19)	C18—C19	1.527 (2)
C1—C6	1.4055 (19)	C18—H18A	0.9900
C2—C3	1.3930 (19)	C18—H18B	0.9900
C2—H2A	0.9500	C19—H19A	0.9900
C3—C4	1.414 (2)	C19—H19B	0.9900
C3—C14	1.4827 (19)	C20—C21	1.362 (2)
C4—C5	1.3808 (19)	C20—H20A	0.9500
C4—H4A	0.9500	C21—H21A	0.9500
C5—C6	1.3960 (19)	C22—H22A	0.9500
C5—H5A	0.9500	C23—H23A	0.9900
C7—C8	1.4714 (18)	C23—H23B	0.9900
C8—C9	1.3971 (19)
C14—O1—C15	116.47 (12)	C8—C13—H13A	121.5
C12—O3—C23	105.42 (11)	O2—C14—O1	123.34 (13)
C11—O4—C23	105.71 (11)	O2—C14—C3	124.47 (13)
C7—N1—C1	104.66 (11)	O1—C14—C3	112.18 (12)
C6—N2—C7	106.21 (11)	O1—C15—C16	107.36 (14)
C6—N2—C17	123.07 (12)	O1—C15—H15A	110.2
C7—N2—C17	129.61 (11)	C16—C15—H15A	110.2
C22—N3—C20	106.20 (13)	O1—C15—H15B	110.2
C22—N3—C19	127.97 (13)	C16—C15—H15B	110.2
C20—N3—C19	125.67 (13)	H15A—C15—H15B	108.5
C22—N4—C21	104.39 (13)	C15—C16—H16A	109.5
N1—C1—C2	130.07 (13)	C15—C16—H16B	109.5
N1—C1—C6	110.32 (12)	H16A—C16—H16B	109.5
C2—C1—C6	119.58 (12)	C15—C16—H16C	109.5
C3—C2—C1	118.01 (13)	H16A—C16—H16C	109.5
C3—C2—H2A	121.0	H16B—C16—H16C	109.5
C1—C2—H2A	121.0	N2—C17—C18	113.51 (12)
C2—C3—C4	121.29 (13)	N2—C17—H17A	108.9
C2—C3—C14	117.30 (12)	C18—C17—H17A	108.9
C4—C3—C14	121.40 (12)	N2—C17—H17B	108.9
C5—C4—C3	121.39 (13)	C18—C17—H17B	108.9
C5—C4—H4A	119.3	H17A—C17—H17B	107.7
C3—C4—H4A	119.3	C19—C18—C17	110.03 (13)
C4—C5—C6	116.60 (13)	C19—C18—H18A	109.7
C4—C5—H5A	121.7	C17—C18—H18A	109.7
C6—C5—H5A	121.7	C19—C18—H18B	109.7
N2—C6—C5	131.09 (13)	C17—C18—H18B	109.7
N2—C6—C1	105.74 (12)	H18A—C18—H18B	108.2
C5—C6—C1	123.12 (13)	N3—C19—C18	111.80 (12)
N1—C7—N2	113.06 (12)	N3—C19—H19A	109.3
N1—C7—C8	123.27 (12)	C18—C19—H19A	109.3
N2—C7—C8	123.62 (12)	N3—C19—H19B	109.3
C9—C8—C13	120.01 (13)	C18—C19—H19B	109.3
C9—C8—C7	122.22 (12)	H19A—C19—H19B	107.9
C13—C8—C7	117.77 (12)	C21—C20—N3	105.91 (14)
C8—C9—C10	121.81 (13)	C21—C20—H20A	127.0
C8—C9—H9A	119.1	N3—C20—H20A	127.0
C10—C9—H9A	119.1	C20—C21—N4	110.72 (14)
C11—C10—C9	117.00 (13)	C20—C21—H21A	124.6
C11—C10—H10A	121.5	N4—C21—H21A	124.6
C9—C10—H10A	121.5	N4—C22—N3	112.77 (14)
C10—C11—O4	127.96 (13)	N4—C22—H22A	123.6
C10—C11—C12	121.89 (13)	N3—C22—H22A	123.6
O4—C11—C12	110.12 (12)	O4—C23—O3	107.33 (11)
C13—C12—O3	128.07 (13)	O4—C23—H23A	110.2
C13—C12—C11	122.22 (13)	O3—C23—H23A	110.2
O3—C12—C11	109.69 (12)	O4—C23—H23B	110.2
C12—C13—C8	117.05 (13)	O3—C23—H23B	110.2
C12—C13—H13A	121.5	H23A—C23—H23B	108.5
C7—N1—C1—C2	−177.49 (15)	C23—O4—C11—C10	172.62 (15)
C7—N1—C1—C6	0.61 (16)	C23—O4—C11—C12	−9.19 (16)
N1—C1—C2—C3	178.57 (14)	C23—O3—C12—C13	−174.54 (15)
C6—C1—C2—C3	0.6 (2)	C23—O3—C12—C11	6.74 (15)
C1—C2—C3—C4	−1.1 (2)	C10—C11—C12—C13	1.0 (2)
C1—C2—C3—C14	177.48 (13)	O4—C11—C12—C13	−177.28 (13)
C2—C3—C4—C5	0.5 (2)	C10—C11—C12—O3	179.84 (13)
C14—C3—C4—C5	−178.07 (13)	O4—C11—C12—O3	1.53 (16)
C3—C4—C5—C6	0.7 (2)	O3—C12—C13—C8	179.77 (13)
C7—N2—C6—C5	176.99 (15)	C11—C12—C13—C8	−1.7 (2)
C17—N2—C6—C5	8.0 (2)	C9—C8—C13—C12	1.3 (2)
C7—N2—C6—C1	−0.47 (15)	C7—C8—C13—C12	−178.39 (12)
C17—N2—C6—C1	−169.43 (12)	C15—O1—C14—O2	1.4 (2)
C4—C5—C6—N2	−178.25 (14)	C15—O1—C14—C3	−179.31 (13)
C4—C5—C6—C1	−1.2 (2)	C2—C3—C14—O2	2.2 (2)
N1—C1—C6—N2	−0.08 (16)	C4—C3—C14—O2	−179.15 (14)
C2—C1—C6—N2	178.25 (12)	C2—C3—C14—O1	−177.08 (13)
N1—C1—C6—C5	−177.79 (13)	C4—C3—C14—O1	1.5 (2)
C2—C1—C6—C5	0.5 (2)	C14—O1—C15—C16	−155.28 (14)
C1—N1—C7—N2	−0.93 (16)	C6—N2—C17—C18	−81.03 (16)
C1—N1—C7—C8	176.36 (13)	C7—N2—C17—C18	112.77 (16)
C6—N2—C7—N1	0.91 (16)	N2—C17—C18—C19	−175.90 (12)
C17—N2—C7—N1	168.90 (13)	C22—N3—C19—C18	−99.29 (17)
C6—N2—C7—C8	−176.38 (13)	C20—N3—C19—C18	75.53 (18)
C17—N2—C7—C8	−8.4 (2)	C17—C18—C19—N3	64.76 (16)
N1—C7—C8—C9	144.90 (15)	C22—N3—C20—C21	−0.74 (16)
N2—C7—C8—C9	−38.1 (2)	C19—N3—C20—C21	−176.49 (13)
N1—C7—C8—C13	−35.4 (2)	N3—C20—C21—N4	0.52 (17)
N2—C7—C8—C13	141.59 (14)	C22—N4—C21—C20	−0.09 (18)
C13—C8—C9—C10	−0.3 (2)	C21—N4—C22—N3	−0.41 (17)
C7—C8—C9—C10	179.35 (13)	C20—N3—C22—N4	0.74 (17)
C8—C9—C10—C11	−0.4 (2)	C19—N3—C22—N4	176.37 (13)
C9—C10—C11—O4	178.02 (14)	C11—O4—C23—O3	13.14 (15)
C9—C10—C11—C12	0.0 (2)	C12—O3—C23—O4	−12.24 (15)

Cg1 and Cg4 are the centroids of C11/C12/O3/C23/O4 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O3i	0.95	2.48	3.3922 (17)	162
C15—H15B···O4ii	0.99	2.49	3.213 (2)	130
C23—H23A···N4iii	0.99	2.43	3.379 (2)	159
C10—H10A···Cg4iv	0.95	2.65	3.3005 (16)	126
C16—H16C···Cg1v	0.98	2.91	3.7282 (19)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg4 are the centroids of C11/C12/O3/C23/O4 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O3i	0.95	2.48	3.3922 (17)	162
C15—H15B⋯O4ii	0.99	2.49	3.213 (2)	130
C23—H23A⋯N4iii	0.99	2.43	3.379 (2)	159
C10—H10A⋯Cg4iv	0.95	2.65	3.3005 (16)	126
C16—H16C⋯Cg1v	0.98	2.91	3.7282 (19)	142

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