Ethyl 2-(1,3-benzodioxol-5-yl)-1-[3-(1H-imidazol-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate

Yoon, Y.K.; Ali, M.A.; Choon, T.S.; Asik, S.I.J.; Razak, I.A.

doi:10.1107/S1600536811054572

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 1| January 2012| Pages o247-o248

doi:10.1107/S1600536811054572

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Ethyl 2-(1,3-benzodioxol-5-yl)-1-[3-(1H-imidazol-1-yl)propyl]-1H-benzimidazole-5-carboxylate

Yeong Keng Yoon,^a Mohamed Ashraf Ali,^a Tan Soo Choon,^a Safra Izuani Jama Asik ^b and Ibrahim Abdul Razak ^b ^*‡

^aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia, and ^bSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: arazaki@usm.my

(Received 14 December 2011; accepted 19 December 2011; online 23 December 2011)

In the title compound, C₂₃H₂₂N₄O₄, 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 methylene C atom at the flap. In the crystal, C—H⋯O and C—H⋯N interactions link the molecules into a ribbon along the a axis. The crystal packing is further stabilized by weak π–π stacking interactions [centroid–centroid distances = 3.5954 (8) and 3.7134 (8) Å] and C—H⋯π interactions.

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_r = 418.45
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.051
wR(F²) = 0.126
S = 1.06
5782 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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⋯Cg4^iv	0.95	2.65	3.3005 (16)	126
C16—H16C⋯Cg1^v	0.98	2.91	3.7282 (19)	142
Symmetry codes: (i) $[x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ ; (ii) x-1, y, z; (iii) -x+2, -y+2, -z+1; (iv) $[-x, y+{\script{3\over 2}}, -z+{\script{3\over 2}}]$ ; (v) -x+1, -y+2, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811054572/is5032sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811054572/is5032Isup3.cml

checkCIF report

Comment top

Benzimidazole derivatives are of wide interest because of their diverse biological activities and various clinical applications. In particular, 2-substituted benzimidazoles have been proven as effective drug leads, thus generating pharmacological interests (Grassmann et al., 2002; Demirayak et al., 2002). As part of our ongoing structural studies of benzimidazole derivatives (Yoon et al., 2011), we now report the structure of the title compound.

Fig. 1 shows the molecular structure of the title compound. The benzimidazole (N1–N2/C1–C7) ring is approximately planar with a maximum deviation of 0.022 (1) Å for atoms C6 and C7. The mean plane through this ring forms dihedral angles of 86.16 (7) and 37.38 (6)° with the mean plane through the imidazole (N3/N4/C20–C22) and benzene (C8–C13) rings, respectively. The dioxolane (O3/O4/C11/C12/C23) ring adopts an envelope conformation with puckering parameters Q = 0.1209 (14) Å and ϕ = 138.2 (7)° with atom C23 at the flap (Cremer & Pople, 1975).

In the crystal packing of (Fig. 2), intermolecular C2—H2A···O3(x - 1/2, y, -z + 3/2), C15—H15B···O4(-1 + x, y, z) and C23—H23A···N4(2 - x, 2 - y, 1 - z) interactions form the molecules into ribbon stacked along the a-axis. π–π interactions are observed within the benzimidazole ring system between the imidazole (N1/N2/C1/C6–C7; centroid Cg2) and benzene, (C1–C6; centroid Cg4) rings with a Cg2···Cg4(1 - x , 2 - y, 1 - z) distance of 3.5954 (8) Å and between the benzene, (C1–C6; centroid Cg4) rings with a Cg4···Cg4 (1 - x, 2 - y, 1 - z) distance of 3.7134 (8) Å. The crystal packing are further stabilized by weak C—H···π interactions (Table 1) involving the benzene ring of the benzimidazole moiety and the dioxolane ring with the distances of 3.3005 (16) and 3.7282 (19) Å, respectively.

Related literature top

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 top

Ethyl-4-[3-(1H-imidazol-1-yl)propylamino]-3-aminobenzoate (0.84 mmol) and sodium metabisulfite adduct of piperonal (1.68 mmol) were dissolved in DMF. The reaction mixture was reflux at 130 °C for 2 hrs. After completion, the reaction mixture was diluted in ethyl acetate (20 mL) and washed with water (20 mL). The organic layer was collected, dried over Na₂SO₄ and the evaporated in vacuo to yield the product. The product was recrystallised from ethyl acetate.

Computing details top

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

Figures top

	Fig. 1. The structure of the title compound, showing 50% probability displacement ellipsoids. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. The crystal packing, viewed along the c-axis, showing the molecules are connected into ribbon along a axis. Hydrogen bonds are shown as dashed lines.

Ethyl 2-(1,3-benzodioxol-5-yl)-1-[3-(1H-imidazol-1-yl)propyl]- 1H-benzimidazole-5-carboxylate top

Crystal data top

C₂₃H₂₂N₄O₄	F(000) = 1760
M_r = 418.45	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0539P)² + 1.7654P] where P = (F_o² + 2F_c²)/3
5782 reflections	(Δ/σ)_max = 0.001
280 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₃H₂₂N₄O₄	V = 3962.43 (9) Å³
M_r = 418.45	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 15.8554 (2) Å	µ = 0.10 mm⁻¹
b = 15.3988 (2) Å	T = 100 K
c = 16.2292 (2) Å	0.42 × 0.28 × 0.20 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5782 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4429 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.981	R_int = 0.054
39067 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.06	Δρ_max = 0.42 e Å⁻³
5782 reflections	Δρ_min = −0.26 e Å⁻³
280 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···Cg4^iv	0.95	2.65	3.3005 (16)	126
C16—H16C···Cg1^v	0.98	2.91	3.7282 (19)	142

Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) x−1, y, z; (iii) −x+2, −y+2, −z+1; (iv) −x, y+3/2, −z+3/2; (v) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₂N₄O₄
M_r	418.45
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	15.8554 (2), 15.3988 (2), 16.2292 (2)
V (Å³)	3962.43 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.42 × 0.28 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.960, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	39067, 5782, 4429
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.126, 1.06
No. of reflections	5782
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.26

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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···Cg4^iv	0.95	2.65	3.3005 (16)	126
C16—H16C···Cg1^v	0.98	2.91	3.7282 (19)	142

Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) x−1, y, z; (iii) −x+2, −y+2, −z+1; (iv) −x, y+3/2, −z+3/2; (v) −x+1, −y+2, −z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grants Nos. 1001/PFIZIK/811151 and (1001/PSK/8620012). The authors also wish to express their thanks to the Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Molecular Medicine, Universiti of Sains Malaysia, Penang.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Demirayak, Ş., Abu Mohsen, U. & Çaqri Karaburun, A. (2002). Eur. J. Med. Chem. 37, 255–260. Web of Science CrossRef PubMed CAS Google Scholar
Grassmann, S., Sadek, B., Ligneau, X., Elz, S., Ganellin, C. R., Arrang, J. M., Schwartz, J. C., Stark, H. & Schunack, W. (2002). Eur. J. Pharm. Sci. 15, 367–378. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yoon, Y. K., Ali, M. A., Wei, A. C., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o2405. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 1| January 2012| Pages o247-o248

doi:10.1107/S1600536811054572

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 2-(1,3-benzodioxol-5-yl)-1-[3-(1H-imidazol-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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Acknowledgements

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organic compounds

Ethyl 2-(1,3-benzodioxol-5-yl)-1-[3-(1H-imidazol-1-yl)propyl]-1H-benzimidazole-5-carboxylate