Ethyl 2-(4-nitro­phen­yl)-1-[3-(2-oxopyrrolidin-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/S1600536811052408

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o59

doi:10.1107/S1600536811052408

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Ethyl 2-(4-nitrophenyl)-1-[3-(2-oxopyrrolidin-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 30 November 2011; accepted 5 December 2011; online 10 December 2011)

In the title compound, C₂₃H₂₄N₄O₅, the essentially planar benzimidazole ring system [maximum deviation = 0.008 (2) Å] forms a dihedral angle of 39.22 (7)° with the attached nitrobenzene ring. The pyrrolidin-2-one ring adopts an envelope conformation with a C atom as the flap. In the crystal, molecules are connected by C—H⋯O interactions, forming sheets propagating in (011). The crystal packing also features weak π–π stacking interactions [centroid–centroid = 3.6746 (12) Å].

Related literature

For applications of benzimidazole compounds, see: Rao et al. (2002 ); Ali et al. (2007 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ). For ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₃H₂₄N₄O₅
M_r = 436.46
Triclinic, $[P \overline 1]$
a = 9.3125 (1) Å
b = 10.0941 (1) Å
c = 12.9955 (2) Å
α = 91.958 (1)°
β = 107.752 (1)°
γ = 114.465 (1)°
V = 1040.67 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.34 × 0.20 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.967, T_max = 0.987
27734 measured reflections
7466 independent reflections
5375 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.197
S = 1.04
7466 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O3ⁱ	0.99	2.41	3.355 (3)	159
C15—H15B⋯O3ⁱⁱ	0.99	2.38	3.186 (3)	139
C19—H19A⋯O2ⁱⁱⁱ	0.99	2.38	3.312 (3)	156
Symmetry codes: (i) x-1, y-1, z-1; (ii) -x, -y, -z+1; (iii) -x-1, -y, -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/S1600536811052408/hb6545sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811052408/hb6545Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811052408/hb6545Isup3.cml

checkCIF report

Comment top

Benzimidazole derivatives have many clinical applications (Rao et al., 2002) and are being currently evaluated for their anti-TB activities (Ali et al., 2007).

In the title compound, (I), Fig. 1, the benzimidazole (N1–N2/C1–C7) ring is essentially planar with maximum deviation of 0.008 (2) for atom C3. This ring also makes dihedral angles of 77.02 (11) and 39.22 (7)° with the mean plane of pyrrolidin-2-one, (O3/N3/C20–C23) and nitrobenzene, (C8–C13) groups, respectively. The mean plane of pyrrolidin-2-one, (O3/N3/C20–C23) adopts an envelope conformation with puckering parameters Q = 0.237 (3) Å and ϕ = 76.0 (6)° (Cremer & Pople, 1975).

In the crystal (Fig. 2), the molecules are connected by C15—H15A···O3, C15—H15B···O3 and C19—H19A···O2 interactions to form (011) sheets. π–π stacking interactions are observed between the benzene (C1–C6; centroid Cg3) rings with their centroids distance of 3.6746 (12) Å [symmetry code : -x,-y,1-z].

Related literature top

For applications of benzimidazole compounds, see: Rao et al. (2002); Ali et al. (2007). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For ring conformations, see: Cremer & Pople (1975).

Experimental top

Ethyl 3-amino-4-(3(2-oxopyrrolidin-1yl)propylamino)benzoate (0.84 mmol) and sodium metabisulfite adduct of 4-nitrobenzaldehyde (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 as orange blocks.

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.
	Fig. 2. The crystal packing, viewed along the a-axis, showing two-dimensional planes parallel to (011). Hydrogen atoms that not involved in hydrogen bonding (dashed lines) are omitted for clarity.

Ethyl 2-(4-nitrophenyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]- 1H-benzimidazole-5-carboxylate top

Crystal data top

C₂₃H₂₄N₄O₅	Z = 2
M_r = 436.46	F(000) = 460
Triclinic, P1	D_x = 1.393 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3125 (1) Å	Cell parameters from 8871 reflections
b = 10.0941 (1) Å	θ = 2.5–32.6°
c = 12.9955 (2) Å	µ = 0.10 mm⁻¹
α = 91.958 (1)°	T = 100 K
β = 107.752 (1)°	Block, orange
γ = 114.465 (1)°	0.34 × 0.20 × 0.13 mm
V = 1040.67 (2) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	7466 independent reflections
Radiation source: fine-focus sealed tube	5375 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 32.6°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
T_min = 0.967, T_max = 0.987	k = −15→15
27734 measured reflections	l = −19→19

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.197	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0843P)² + 0.8488P] where P = (F_o² + 2F_c²)/3
7466 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₃H₂₄N₄O₅	γ = 114.465 (1)°
M_r = 436.46	V = 1040.67 (2) Å³
Triclinic, P1	Z = 2
a = 9.3125 (1) Å	Mo Kα radiation
b = 10.0941 (1) Å	µ = 0.10 mm⁻¹
c = 12.9955 (2) Å	T = 100 K
α = 91.958 (1)°	0.34 × 0.20 × 0.13 mm
β = 107.752 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	7466 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5375 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.987	R_int = 0.032
27734 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.197	H-atom parameters constrained
S = 1.04	Δρ_max = 0.50 e Å⁻³
7466 reflections	Δρ_min = −0.30 e Å⁻³
289 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	−0.29047 (16)	−0.18231 (15)	0.17443 (11)	0.0271 (3)
O2	−0.45664 (18)	−0.31986 (16)	0.26240 (12)	0.0328 (3)
O3	0.2053 (2)	0.51173 (19)	0.95685 (13)	0.0385 (4)
O4	0.82578 (18)	0.95186 (18)	0.77738 (14)	0.0371 (4)
O5	0.6533 (2)	1.04206 (17)	0.78208 (14)	0.0388 (4)
N1	0.11744 (17)	0.29815 (16)	0.46007 (12)	0.0201 (3)
N2	0.00661 (17)	0.29678 (16)	0.59278 (11)	0.0193 (3)
N3	−0.0066 (2)	0.56743 (18)	0.86162 (13)	0.0245 (3)
N4	0.6825 (2)	0.93979 (18)	0.75733 (13)	0.0268 (3)
C1	−0.0276 (2)	0.16584 (19)	0.43862 (14)	0.0189 (3)
C2	−0.1050 (2)	0.04589 (19)	0.35168 (14)	0.0201 (3)
H2A	−0.0586	0.0455	0.2959	0.024*
C3	−0.2518 (2)	−0.07262 (19)	0.34957 (14)	0.0208 (3)
C4	−0.3197 (2)	−0.0732 (2)	0.43315 (15)	0.0233 (3)
H4A	−0.4194	−0.1570	0.4299	0.028*
C5	−0.2451 (2)	0.0444 (2)	0.51921 (14)	0.0224 (3)
H5A	−0.2914	0.0443	0.5751	0.027*
C6	−0.0981 (2)	0.16403 (19)	0.52027 (14)	0.0194 (3)
C7	0.1333 (2)	0.37277 (18)	0.55203 (14)	0.0185 (3)
C8	0.2713 (2)	0.52054 (19)	0.60439 (13)	0.0193 (3)
C9	0.2460 (2)	0.6325 (2)	0.65125 (14)	0.0217 (3)
H9A	0.1366	0.6135	0.6500	0.026*
C10	0.3803 (2)	0.7712 (2)	0.69957 (14)	0.0221 (3)
H10A	0.3638	0.8478	0.7310	0.026*
C11	0.5388 (2)	0.79566 (19)	0.70104 (14)	0.0216 (3)
C12	0.5674 (2)	0.6891 (2)	0.65223 (15)	0.0237 (3)
H12A	0.6764	0.7100	0.6517	0.028*
C13	0.4322 (2)	0.5512 (2)	0.60426 (14)	0.0221 (3)
H13A	0.4491	0.4763	0.5708	0.027*
C14	−0.3446 (2)	−0.2050 (2)	0.25940 (15)	0.0234 (3)
C15	−0.3754 (2)	−0.3076 (2)	0.08290 (16)	0.0292 (4)
H15A	−0.4990	−0.3501	0.0636	0.035*
H15B	−0.3399	−0.3859	0.1032	0.035*
C16	−0.3270 (3)	−0.2504 (3)	−0.01223 (19)	0.0441 (6)
H16A	−0.3815	−0.3318	−0.0754	0.066*
H16B	−0.2044	−0.2086	0.0080	0.066*
H16C	−0.3632	−0.1734	−0.0316	0.066*
C17	−0.0017 (2)	0.3308 (2)	0.70099 (13)	0.0214 (3)
H17A	0.1063	0.4151	0.7467	0.026*
H17B	−0.0149	0.2442	0.7376	0.026*
C18	−0.1456 (2)	0.3693 (2)	0.69594 (14)	0.0236 (3)
H18A	−0.2548	0.2819	0.6574	0.028*
H18B	−0.1392	0.4503	0.6540	0.028*
C19	−0.1347 (2)	0.4175 (2)	0.81236 (15)	0.0261 (4)
H19A	−0.2453	0.4099	0.8095	0.031*
H19B	−0.1099	0.3490	0.8594	0.031*
C20	−0.0400 (3)	0.6949 (2)	0.84211 (18)	0.0354 (5)
H20A	−0.1478	0.6790	0.8505	0.042*
H20B	−0.0439	0.7153	0.7676	0.042*
C21	0.1094 (4)	0.8213 (3)	0.9307 (2)	0.0443 (6)
H21A	0.1467	0.9144	0.9017	0.053*
H21B	0.0793	0.8379	0.9952	0.053*
C22	0.2468 (3)	0.7692 (2)	0.96175 (18)	0.0353 (5)
H22A	0.3248	0.8102	0.9210	0.042*
H22B	0.3121	0.7996	1.0416	0.042*
C23	0.1509 (2)	0.6021 (2)	0.92917 (15)	0.0268 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0245 (6)	0.0248 (7)	0.0246 (6)	0.0055 (5)	0.0078 (5)	−0.0053 (5)
O2	0.0311 (7)	0.0247 (7)	0.0282 (7)	0.0022 (6)	0.0062 (6)	0.0020 (6)
O3	0.0361 (8)	0.0421 (9)	0.0348 (8)	0.0228 (7)	0.0031 (6)	−0.0081 (7)
O4	0.0244 (7)	0.0338 (8)	0.0417 (9)	0.0048 (6)	0.0088 (6)	0.0019 (7)
O5	0.0404 (8)	0.0261 (8)	0.0417 (9)	0.0100 (7)	0.0116 (7)	−0.0034 (6)
N1	0.0184 (6)	0.0202 (7)	0.0214 (7)	0.0080 (5)	0.0073 (5)	0.0017 (5)
N2	0.0188 (6)	0.0213 (7)	0.0165 (6)	0.0072 (5)	0.0070 (5)	0.0028 (5)
N3	0.0271 (7)	0.0251 (8)	0.0226 (7)	0.0122 (6)	0.0097 (6)	0.0024 (6)
N4	0.0276 (7)	0.0226 (8)	0.0231 (7)	0.0048 (6)	0.0089 (6)	0.0020 (6)
C1	0.0173 (7)	0.0202 (8)	0.0204 (7)	0.0086 (6)	0.0079 (6)	0.0034 (6)
C2	0.0194 (7)	0.0206 (8)	0.0200 (7)	0.0089 (6)	0.0068 (6)	0.0019 (6)
C3	0.0193 (7)	0.0205 (8)	0.0204 (7)	0.0079 (6)	0.0053 (6)	0.0028 (6)
C4	0.0199 (7)	0.0222 (8)	0.0240 (8)	0.0058 (6)	0.0078 (6)	0.0064 (6)
C5	0.0221 (7)	0.0228 (8)	0.0205 (7)	0.0069 (7)	0.0092 (6)	0.0048 (6)
C6	0.0188 (7)	0.0199 (8)	0.0178 (7)	0.0078 (6)	0.0055 (6)	0.0025 (6)
C7	0.0181 (7)	0.0177 (7)	0.0194 (7)	0.0078 (6)	0.0064 (6)	0.0028 (6)
C8	0.0195 (7)	0.0204 (8)	0.0174 (7)	0.0086 (6)	0.0063 (6)	0.0033 (6)
C9	0.0202 (7)	0.0230 (8)	0.0232 (8)	0.0105 (7)	0.0080 (6)	0.0037 (6)
C10	0.0264 (8)	0.0190 (8)	0.0207 (8)	0.0103 (7)	0.0080 (6)	0.0027 (6)
C11	0.0222 (7)	0.0194 (8)	0.0184 (7)	0.0051 (6)	0.0066 (6)	0.0028 (6)
C12	0.0200 (7)	0.0245 (9)	0.0241 (8)	0.0067 (7)	0.0093 (6)	0.0031 (7)
C13	0.0226 (8)	0.0240 (8)	0.0215 (8)	0.0104 (7)	0.0101 (6)	0.0031 (6)
C14	0.0208 (7)	0.0236 (8)	0.0225 (8)	0.0098 (7)	0.0036 (6)	0.0029 (6)
C15	0.0267 (9)	0.0276 (10)	0.0255 (9)	0.0091 (8)	0.0046 (7)	−0.0052 (7)
C16	0.0467 (13)	0.0415 (13)	0.0320 (11)	0.0082 (11)	0.0157 (10)	−0.0058 (10)
C17	0.0224 (7)	0.0263 (9)	0.0149 (7)	0.0103 (7)	0.0067 (6)	0.0033 (6)
C18	0.0196 (7)	0.0285 (9)	0.0202 (8)	0.0084 (7)	0.0072 (6)	−0.0003 (7)
C19	0.0234 (8)	0.0301 (9)	0.0238 (8)	0.0088 (7)	0.0119 (7)	0.0000 (7)
C20	0.0498 (12)	0.0293 (10)	0.0289 (10)	0.0226 (10)	0.0095 (9)	0.0032 (8)
C21	0.0650 (16)	0.0292 (11)	0.0329 (11)	0.0212 (11)	0.0094 (11)	0.0030 (9)
C22	0.0365 (10)	0.0305 (10)	0.0285 (10)	0.0038 (9)	0.0143 (8)	−0.0019 (8)
C23	0.0284 (9)	0.0302 (10)	0.0216 (8)	0.0116 (8)	0.0114 (7)	−0.0017 (7)

Geometric parameters (Å, º) top

O1—C14	1.337 (2)	C10—C11	1.386 (2)
O1—C15	1.461 (2)	C10—H10A	0.9500
O2—C14	1.208 (2)	C11—C12	1.387 (3)
O3—C23	1.229 (3)	C12—C13	1.386 (3)
O4—N4	1.231 (2)	C12—H12A	0.9500
O5—N4	1.227 (2)	C13—H13A	0.9500
N1—C7	1.325 (2)	C15—C16	1.496 (3)
N1—C1	1.392 (2)	C15—H15A	0.9900
N2—C6	1.380 (2)	C15—H15B	0.9900
N2—C7	1.386 (2)	C16—H16A	0.9800
N2—C17	1.468 (2)	C16—H16B	0.9800
N3—C23	1.347 (2)	C16—H16C	0.9800
N3—C19	1.448 (2)	C17—C18	1.527 (2)
N3—C20	1.456 (3)	C17—H17A	0.9900
N4—C11	1.470 (2)	C17—H17B	0.9900
C1—C2	1.396 (2)	C18—C19	1.534 (2)
C1—C6	1.405 (2)	C18—H18A	0.9900
C2—C3	1.386 (2)	C18—H18B	0.9900
C2—H2A	0.9500	C19—H19A	0.9900
C3—C4	1.413 (2)	C19—H19B	0.9900
C3—C14	1.492 (2)	C20—C21	1.531 (3)
C4—C5	1.377 (3)	C20—H20A	0.9900
C4—H4A	0.9500	C20—H20B	0.9900
C5—C6	1.396 (2)	C21—C22	1.527 (4)
C5—H5A	0.9500	C21—H21A	0.9900
C7—C8	1.466 (2)	C21—H21B	0.9900
C8—C13	1.400 (2)	C22—C23	1.515 (3)
C8—C9	1.402 (2)	C22—H22A	0.9900
C9—C10	1.389 (3)	C22—H22B	0.9900
C9—H9A	0.9500

C14—O1—C15	115.53 (15)	O1—C14—C3	112.44 (15)
C7—N1—C1	104.74 (14)	O1—C15—C16	107.13 (17)
C6—N2—C7	106.18 (13)	O1—C15—H15A	110.3
C6—N2—C17	124.31 (14)	C16—C15—H15A	110.3
C7—N2—C17	128.43 (14)	O1—C15—H15B	110.3
C23—N3—C19	123.98 (17)	C16—C15—H15B	110.3
C23—N3—C20	114.20 (17)	H15A—C15—H15B	108.5
C19—N3—C20	121.81 (16)	C15—C16—H16A	109.5
O5—N4—O4	123.33 (17)	C15—C16—H16B	109.5
O5—N4—C11	118.19 (16)	H16A—C16—H16B	109.5
O4—N4—C11	118.48 (16)	C15—C16—H16C	109.5
N1—C1—C2	129.65 (15)	H16A—C16—H16C	109.5
N1—C1—C6	110.09 (15)	H16B—C16—H16C	109.5
C2—C1—C6	120.25 (16)	N2—C17—C18	113.73 (14)
C3—C2—C1	117.63 (16)	N2—C17—H17A	108.8
C3—C2—H2A	121.2	C18—C17—H17A	108.8
C1—C2—H2A	121.2	N2—C17—H17B	108.8
C2—C3—C4	121.30 (16)	C18—C17—H17B	108.8
C2—C3—C14	121.58 (16)	H17A—C17—H17B	107.7
C4—C3—C14	117.12 (16)	C17—C18—C19	110.22 (14)
C5—C4—C3	121.73 (16)	C17—C18—H18A	109.6
C5—C4—H4A	119.1	C19—C18—H18A	109.6
C3—C4—H4A	119.1	C17—C18—H18B	109.6
C4—C5—C6	116.66 (16)	C19—C18—H18B	109.6
C4—C5—H5A	121.7	H18A—C18—H18B	108.1
C6—C5—H5A	121.7	N3—C19—C18	112.88 (15)
N2—C6—C5	131.67 (16)	N3—C19—H19A	109.0
N2—C6—C1	105.92 (14)	C18—C19—H19A	109.0
C5—C6—C1	122.42 (16)	N3—C19—H19B	109.0
N1—C7—N2	113.07 (15)	C18—C19—H19B	109.0
N1—C7—C8	122.98 (15)	H19A—C19—H19B	107.8
N2—C7—C8	123.96 (15)	N3—C20—C21	103.43 (18)
C13—C8—C9	119.31 (16)	N3—C20—H20A	111.1
C13—C8—C7	118.47 (15)	C21—C20—H20A	111.1
C9—C8—C7	122.19 (15)	N3—C20—H20B	111.1
C10—C9—C8	120.27 (15)	C21—C20—H20B	111.1
C10—C9—H9A	119.9	H20A—C20—H20B	109.0
C8—C9—H9A	119.9	C22—C21—C20	104.44 (18)
C11—C10—C9	118.67 (16)	C22—C21—H21A	110.9
C11—C10—H10A	120.7	C20—C21—H21A	110.9
C9—C10—H10A	120.7	C22—C21—H21B	110.9
C10—C11—C12	122.60 (16)	C20—C21—H21B	110.9
C10—C11—N4	118.71 (16)	H21A—C21—H21B	108.9
C12—C11—N4	118.68 (16)	C23—C22—C21	104.12 (18)
C13—C12—C11	118.05 (16)	C23—C22—H22A	110.9
C13—C12—H12A	121.0	C21—C22—H22A	110.9
C11—C12—H12A	121.0	C23—C22—H22B	110.9
C12—C13—C8	121.02 (16)	C21—C22—H22B	110.9
C12—C13—H13A	119.5	H22A—C22—H22B	109.0
C8—C13—H13A	119.5	O3—C23—N3	124.88 (19)
O2—C14—O1	123.64 (17)	O3—C23—C22	127.05 (19)
O2—C14—C3	123.92 (17)	N3—C23—C22	108.06 (18)

C7—N1—C1—C2	179.48 (17)	C9—C10—C11—N4	−176.78 (16)
C7—N1—C1—C6	0.23 (19)	O5—N4—C11—C10	−13.9 (3)
N1—C1—C2—C3	−179.08 (17)	O4—N4—C11—C10	166.00 (17)
C6—C1—C2—C3	0.1 (2)	O5—N4—C11—C12	166.58 (18)
C1—C2—C3—C4	−0.9 (3)	O4—N4—C11—C12	−13.5 (3)
C1—C2—C3—C14	179.30 (15)	C10—C11—C12—C13	−2.7 (3)
C2—C3—C4—C5	1.2 (3)	N4—C11—C12—C13	176.81 (16)
C14—C3—C4—C5	−179.04 (16)	C11—C12—C13—C8	0.4 (3)
C3—C4—C5—C6	−0.5 (3)	C9—C8—C13—C12	1.7 (3)
C7—N2—C6—C5	−179.83 (18)	C7—C8—C13—C12	179.80 (16)
C17—N2—C6—C5	11.2 (3)	C15—O1—C14—O2	−0.5 (3)
C7—N2—C6—C1	0.53 (18)	C15—O1—C14—C3	179.81 (15)
C17—N2—C6—C1	−168.39 (15)	C2—C3—C14—O2	167.84 (18)
C4—C5—C6—N2	−179.88 (17)	C4—C3—C14—O2	−12.0 (3)
C4—C5—C6—C1	−0.3 (3)	C2—C3—C14—O1	−12.4 (2)
N1—C1—C6—N2	−0.49 (19)	C4—C3—C14—O1	167.77 (15)
C2—C1—C6—N2	−179.81 (15)	C14—O1—C15—C16	167.07 (17)
N1—C1—C6—C5	179.83 (16)	C6—N2—C17—C18	−77.5 (2)
C2—C1—C6—C5	0.5 (3)	C7—N2—C17—C18	116.10 (19)
C1—N1—C7—N2	0.12 (19)	N2—C17—C18—C19	−174.58 (15)
C1—N1—C7—C8	−179.84 (15)	C23—N3—C19—C18	−95.5 (2)
C6—N2—C7—N1	−0.42 (19)	C20—N3—C19—C18	85.1 (2)
C17—N2—C7—N1	167.89 (16)	C17—C18—C19—N3	77.3 (2)
C6—N2—C7—C8	179.53 (15)	C23—N3—C20—C21	−13.5 (2)
C17—N2—C7—C8	−12.2 (3)	C19—N3—C20—C21	165.93 (18)
N1—C7—C8—C13	−38.3 (2)	N3—C20—C21—C22	22.3 (2)
N2—C7—C8—C13	141.76 (17)	C20—C21—C22—C23	−23.2 (2)
N1—C7—C8—C9	139.76 (18)	C19—N3—C23—O3	0.2 (3)
N2—C7—C8—C9	−40.2 (2)	C20—N3—C23—O3	179.69 (19)
C13—C8—C9—C10	−1.7 (3)	C19—N3—C23—C22	179.15 (16)
C7—C8—C9—C10	−179.69 (16)	C20—N3—C23—C22	−1.4 (2)
C8—C9—C10—C11	−0.5 (3)	C21—C22—C23—O3	−165.3 (2)
C9—C10—C11—C12	2.7 (3)	C21—C22—C23—N3	15.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O3ⁱ	0.99	2.41	3.355 (3)	159
C15—H15B···O3ⁱⁱ	0.99	2.38	3.186 (3)	139
C19—H19A···O2ⁱⁱⁱ	0.99	2.38	3.312 (3)	156

Symmetry codes: (i) x−1, y−1, z−1; (ii) −x, −y, −z+1; (iii) −x−1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₄N₄O₅
M_r	436.46
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.3125 (1), 10.0941 (1), 12.9955 (2)
α, β, γ (°)	91.958 (1), 107.752 (1), 114.465 (1)
V (Å³)	1040.67 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.34 × 0.20 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.967, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	27734, 7466, 5375
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.758

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.197, 1.04
No. of reflections	7466
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.30

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O3ⁱ	0.99	2.41	3.355 (3)	159
C15—H15B···O3ⁱⁱ	0.99	2.38	3.186 (3)	139
C19—H19A···O2ⁱⁱⁱ	0.99	2.38	3.312 (3)	156

Symmetry codes: (i) x−1, y−1, z−1; (ii) −x, −y, −z+1; (iii) −x−1, −y, −z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant (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.

References

Ali, M. A., Shahar Yar, M. & Siddiqui, A. A. (2007). Eur. J. Med. Chem. 42, 268–275. Web of Science CrossRef PubMed CAS Google Scholar
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
Rao, A., Chimirri, A., Clercq, E. D., Monforte, A. M., Monforte, P., Pannecouque, C. & Zappala, M. (2002). Farmaco, 57, 819–823. 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

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

Ethyl 2-(4-nitro­phen­yl)-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Ethyl 2-(4-nitrophenyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-benzimidazole-5-carboxylate