Ethyl 2-(4-nitro-phen-yl)-1-[3-(2-oxopyrrolidin-1-yl)prop-yl]-1H-benzimidazole-5-carboxyl-ate.

In the title compound, C(23)H(24)N(4)O(5), the essentially planar benzimidazole ring system [maximum deviation = 0.008 (2) Å] forms a dihedral angle of 39.22 (7)° with the attached nitro-benzene ring. The pyrrolidin-2-one ring adopts an envelope conformation with a C atom as the flap. In the crystal, mol-ecules are connected by C-H⋯O inter-actions, forming sheets propagating in (011). The crystal packing also features weak π-π stacking inter-actions [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 = 436.46

Triclinic,

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[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.197

S = 1.04

7466 reflections

289 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.30 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/S1600536811052408/hb6545sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811052408/hb6545Isup3.cml

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

C23H24N4O5	Z = 2
Mr = 436.46	F(000) = 460
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0843P)2 + 0.8488P] where P = (Fo2 + 2Fc2)/3
7466 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.30 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	−0.29047 (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)

	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)

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)

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

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) ; (ii) ; (iii) .