3-{5-Eth­oxy­carbonyl-1-[3-(2-oxopyrrol­idin-1-yl)prop­yl]-1H-benzimidazol-2-yl}benzoic acid

Yoon, Y.K.; Ali, M.A.; Tan, S.C.; Rosli, M.M.; Razak, I.A.

doi:10.1107/S1600536813001116

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o304

doi:10.1107/S1600536813001116

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3-{5-Ethoxycarbonyl-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-benzimidazol-2-yl}benzoic acid

Yeong Keng Yoon,^a Mohamed Ashraf Ali,^a Soo Choon Tan,^a Mohd Mustaqim Rosli ^b and Ibrahim Abdul Razak ^b ^*

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

(Received 20 December 2012; accepted 11 January 2013; online 31 January 2013)

In the title compound, C₂₄H₂₅N₃O₅, the ethoxy group is disordered over two orientations in a 0.853 (14):0.147 (14) ratio. The benzimadazole ring system (r.m.s. deviation = 0.016 Å) makes a dihedral angle of 35.47 (7)° with the attached benzene ring. The pyrrolidine ring adopts an envelope conformation with a methylene C atom as the flap. In the crystal, inversion dimers linked by pairs of O—H⋯N hydrogen bonds generate R₂²(16) loops. C—H⋯O interactions link the dimers into a three-dimensional network.

Related literature

For a related structure and background to benzimidazoles, see: Yoon et al. (2012 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₄H₂₅N₃O₅
M_r = 435.47
Monoclinic, P 2₁ /c
a = 9.3097 (3) Å
b = 24.8252 (7) Å
c = 9.6761 (3) Å
β = 112.322 (1)°
V = 2068.71 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.39 × 0.23 × 0.08 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.963, T_max = 0.992
23636 measured reflections
6010 independent reflections
3706 reflections with I > 2σ(I)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.134
S = 1.03
6010 reflections
317 parameters
69 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯N2ⁱ	1.04 (4)	1.66 (4)	2.675 (2)	166 (3)
C5—H5A⋯O3ⁱ	0.95	2.57	3.367 (2)	141
C9—H9A⋯O2ⁱ	0.95	2.46	3.177 (2)	132
C15—H15A⋯O3ⁱⁱ	0.99	2.34	3.314 (3)	167
C17—H17B⋯O5ⁱⁱⁱ	0.99	2.51	3.429 (3)	154
C20—H20B⋯O4^iv	0.99	2.55	3.340 (3)	137
Symmetry codes: (i) -x, -y, -z-1; (ii) x, y, z+1; (iii) -x+1, -y, -z+1; (iv) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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 I, global. DOI: 10.1107/S1600536813001116/hb7017sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813001116/hb7017Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813001116/hb7017Isup3.cml

checkCIF report

Comment top

As part of our ongoing structural studies of benzimidazole derivatives (Yoon et al., 2012), we now report the structure of the title compound.

The ethoxy group is disordered over two position with the final refined occupancies of 0.853 (14):0.147 (14). The benzimidazole (N1—N2/C—C7) ring in the title compound, Fig. 1, is almost planar with maximum deviation of 0.02 Å for atom N2 and makes a dihedral angle of 35.63° with the attached benzene ring (C8—C13). The pyrrolidine ring (N3/C18—C21) adopts an envelope conformation with C19 as the flap and puckering parameters Q = 0.262 (3) Å and ϕ = 64.0 (5)°.

In the crystal (Fig. 2), O—H···N and C—H···O interactions (Table 1) link the molecules into a three-dimensional network.

Related literature top

For a related structure and background to benzimidazoles, see: Yoon et al. (2012). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For puckering parameters, 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-carboxy benzaldehyde (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 recrystallized from ethyl acetate as brown plates.

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 of (I). Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.

3-{5-Ethoxycarbonyl-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H- benzimidazol-2-yl}benzoic acid top

Crystal data top

C₂₄H₂₅N₃O₅	F(000) = 920
M_r = 435.47	D_x = 1.398 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3829 reflections
a = 9.3097 (3) Å	θ = 2.4–29.4°
b = 24.8252 (7) Å	µ = 0.10 mm⁻¹
c = 9.6761 (3) Å	T = 100 K
β = 112.322 (1)°	Plate, brown
V = 2068.71 (11) Å³	0.39 × 0.23 × 0.08 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	6010 independent reflections
Radiation source: fine-focus sealed tube	3706 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
ϕ and ω scans	θ_max = 30.1°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
T_min = 0.963, T_max = 0.992	k = −34→34
23636 measured reflections	l = −8→13

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0444P)² + 0.6946P] where P = (F_o² + 2F_c²)/3
6010 reflections	(Δ/σ)_max = 0.001
317 parameters	Δρ_max = 0.37 e Å⁻³
69 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₄H₂₅N₃O₅	V = 2068.71 (11) Å³
M_r = 435.47	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.3097 (3) Å	µ = 0.10 mm⁻¹
b = 24.8252 (7) Å	T = 100 K
c = 9.6761 (3) Å	0.39 × 0.23 × 0.08 mm
β = 112.322 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	6010 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3706 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.992	R_int = 0.065
23636 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	69 restraints
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.37 e Å⁻³
6010 reflections	Δρ_min = −0.31 e Å⁻³
317 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 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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	−0.1036 (4)	−0.15612 (14)	0.1235 (6)	0.0179 (7)	0.853 (14)
C23	−0.1927 (4)	−0.20029 (16)	0.1526 (4)	0.0216 (8)	0.853 (14)
H23A	−0.3036	−0.1964	0.0868	0.026*	0.853 (14)
H23B	−0.1847	−0.1983	0.2575	0.026*	0.853 (14)
C24	−0.1357 (4)	−0.25307 (15)	0.1261 (8)	0.0427 (14)	0.853 (14)
H24A	−0.1986	−0.2817	0.1448	0.064*	0.853 (14)
H24B	−0.0270	−0.2575	0.1935	0.064*	0.853 (14)
H24C	−0.1437	−0.2551	0.0223	0.064*	0.853 (14)
O1X	−0.066 (4)	−0.1693 (10)	0.123 (4)	0.043 (6)	0.147 (14)
C23X	−0.148 (5)	−0.2161 (11)	0.153 (3)	0.054 (5)	0.147 (14)
H23C	−0.1018	−0.2268	0.2591	0.064*	0.147 (14)
H23D	−0.2598	−0.2080	0.1259	0.064*	0.147 (14)
C24X	−0.127 (4)	−0.2575 (9)	0.057 (3)	0.054 (5)	0.147 (14)
H24D	−0.1522	−0.2927	0.0879	0.080*	0.147 (14)
H24E	−0.0185	−0.2575	0.0657	0.080*	0.147 (14)
H24F	−0.1952	−0.2504	−0.0466	0.080*	0.147 (14)
O2	−0.02946 (16)	0.06006 (5)	−0.61398 (17)	0.0181 (3)
O3	0.12028 (16)	0.11302 (5)	−0.69174 (16)	0.0201 (3)
O4	0.43579 (19)	0.23361 (6)	0.23971 (19)	0.0333 (4)
O5	0.06150 (17)	−0.15773 (6)	0.36566 (17)	0.0231 (3)
N1	0.30457 (18)	0.03432 (6)	0.07554 (19)	0.0142 (3)
N2	0.17804 (18)	−0.02457 (6)	−0.10670 (19)	0.0147 (4)
N3	0.61523 (19)	0.17298 (6)	0.2256 (2)	0.0184 (4)
C1	0.2460 (2)	−0.00527 (7)	0.1413 (2)	0.0135 (4)
C2	0.2562 (2)	−0.01238 (8)	0.2868 (2)	0.0145 (4)
H2A	0.3106	0.0124	0.3638	0.017*
C3	0.1832 (2)	−0.05727 (7)	0.3144 (2)	0.0151 (4)
H3A	0.1897	−0.0640	0.4133	0.018*
C4	0.0994 (2)	−0.09329 (7)	0.1994 (2)	0.0147 (4)
C5	0.0890 (2)	−0.08568 (8)	0.0537 (2)	0.0158 (4)
H5A	0.0315	−0.1097	−0.0240	0.019*
C6	0.1663 (2)	−0.04131 (7)	0.0261 (2)	0.0139 (4)
C7	0.2601 (2)	0.02085 (7)	−0.0722 (2)	0.0139 (4)
C8	0.2977 (2)	0.05271 (7)	−0.1826 (2)	0.0145 (4)
C9	0.1876 (2)	0.05557 (7)	−0.3289 (2)	0.0148 (4)
H9A	0.0924	0.0365	−0.3548	0.018*
C10	0.2155 (2)	0.08584 (7)	−0.4364 (2)	0.0148 (4)
C11	0.3555 (2)	0.11325 (8)	−0.3997 (2)	0.0178 (4)
H11A	0.3739	0.1347	−0.4725	0.021*
C12	0.4683 (2)	0.10921 (8)	−0.2565 (2)	0.0185 (4)
H12A	0.5650	0.1271	−0.2325	0.022*
C13	0.4402 (2)	0.07915 (8)	−0.1481 (2)	0.0177 (4)
H13A	0.5179	0.0765	−0.0504	0.021*
C14	0.0980 (2)	0.08844 (7)	−0.5930 (2)	0.0153 (4)
C15	0.3717 (2)	0.08531 (7)	0.1508 (2)	0.0155 (4)
H15A	0.3073	0.0989	0.2044	0.019*
H15B	0.3679	0.1123	0.0742	0.019*
C16	0.5390 (2)	0.07964 (8)	0.2613 (2)	0.0176 (4)
H16A	0.6042	0.0656	0.2090	0.021*
H16B	0.5435	0.0536	0.3404	0.021*
C17	0.6019 (3)	0.13412 (8)	0.3320 (2)	0.0212 (5)
H17A	0.5322	0.1489	0.3786	0.025*
H17B	0.7054	0.1287	0.4121	0.025*
C18	0.7451 (3)	0.17112 (9)	0.1760 (3)	0.0262 (5)
H18A	0.7494	0.1360	0.1293	0.031*
H18B	0.8451	0.1774	0.2604	0.031*
C19	0.7087 (3)	0.21703 (9)	0.0613 (3)	0.0283 (5)
H19A	0.8051	0.2348	0.0645	0.034*
H19B	0.6505	0.2036	−0.0411	0.034*
C20	0.6095 (3)	0.25556 (8)	0.1106 (3)	0.0280 (5)
H20A	0.6740	0.2846	0.1743	0.034*
H20B	0.5269	0.2720	0.0230	0.034*
C21	0.5400 (2)	0.22093 (8)	0.1978 (2)	0.0206 (5)
C22	0.0213 (2)	−0.13958 (8)	0.2405 (2)	0.0181 (4)
H1O2	−0.085 (4)	0.0523 (13)	−0.727 (4)	0.088 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0142 (12)	0.0183 (13)	0.0183 (12)	−0.0053 (9)	0.0027 (10)	0.0015 (11)
C23	0.0192 (16)	0.0166 (16)	0.0258 (16)	−0.0079 (11)	0.0050 (13)	0.0021 (12)
C24	0.0372 (19)	0.0253 (16)	0.064 (4)	−0.0002 (13)	0.018 (2)	−0.0081 (19)
O1X	0.062 (15)	0.034 (9)	0.021 (8)	−0.021 (9)	0.004 (11)	0.003 (9)
C23X	0.090 (13)	0.025 (8)	0.054 (10)	−0.008 (8)	0.037 (10)	−0.004 (8)
C24X	0.090 (13)	0.025 (8)	0.054 (10)	−0.008 (8)	0.037 (10)	−0.004 (8)
O2	0.0158 (7)	0.0229 (7)	0.0141 (8)	−0.0050 (6)	0.0041 (6)	−0.0017 (6)
O3	0.0208 (7)	0.0225 (7)	0.0168 (8)	−0.0016 (6)	0.0069 (6)	0.0022 (6)
O4	0.0335 (9)	0.0364 (9)	0.0320 (11)	0.0089 (7)	0.0148 (8)	−0.0014 (8)
O5	0.0236 (8)	0.0253 (8)	0.0175 (8)	−0.0030 (6)	0.0047 (7)	0.0059 (6)
N1	0.0123 (8)	0.0176 (8)	0.0125 (9)	−0.0010 (6)	0.0045 (7)	−0.0019 (7)
N2	0.0119 (8)	0.0194 (8)	0.0115 (9)	−0.0008 (6)	0.0029 (7)	0.0002 (7)
N3	0.0173 (9)	0.0187 (8)	0.0185 (10)	−0.0009 (7)	0.0060 (8)	0.0018 (7)
C1	0.0100 (9)	0.0159 (9)	0.0143 (10)	0.0005 (7)	0.0042 (8)	−0.0003 (8)
C2	0.0134 (9)	0.0174 (9)	0.0113 (10)	0.0008 (7)	0.0031 (8)	0.0002 (7)
C3	0.0132 (9)	0.0192 (10)	0.0132 (10)	0.0017 (8)	0.0053 (8)	0.0028 (8)
C4	0.0124 (9)	0.0169 (9)	0.0144 (10)	0.0010 (7)	0.0046 (8)	0.0011 (8)
C5	0.0120 (9)	0.0178 (9)	0.0159 (11)	0.0001 (7)	0.0033 (8)	−0.0019 (8)
C6	0.0122 (9)	0.0183 (9)	0.0097 (10)	0.0015 (7)	0.0024 (8)	0.0003 (8)
C7	0.0105 (9)	0.0166 (9)	0.0128 (10)	0.0021 (7)	0.0026 (8)	−0.0002 (8)
C8	0.0146 (10)	0.0172 (9)	0.0130 (10)	0.0014 (7)	0.0067 (8)	−0.0001 (8)
C9	0.0125 (9)	0.0162 (9)	0.0156 (11)	−0.0004 (7)	0.0052 (8)	−0.0014 (8)
C10	0.0154 (9)	0.0154 (9)	0.0139 (10)	0.0018 (7)	0.0058 (8)	−0.0010 (8)
C11	0.0178 (10)	0.0206 (10)	0.0177 (11)	−0.0034 (8)	0.0096 (9)	−0.0018 (8)
C12	0.0151 (10)	0.0234 (10)	0.0180 (11)	−0.0038 (8)	0.0076 (9)	−0.0011 (9)
C13	0.0145 (10)	0.0223 (10)	0.0145 (11)	−0.0004 (8)	0.0036 (9)	−0.0009 (8)
C14	0.0160 (10)	0.0154 (9)	0.0152 (11)	0.0010 (8)	0.0066 (9)	−0.0007 (8)
C15	0.0168 (10)	0.0145 (9)	0.0158 (11)	−0.0007 (8)	0.0069 (9)	−0.0024 (8)
C16	0.0175 (10)	0.0176 (10)	0.0149 (11)	−0.0006 (8)	0.0032 (9)	0.0007 (8)
C17	0.0256 (11)	0.0217 (10)	0.0130 (11)	−0.0055 (9)	0.0037 (9)	0.0013 (8)
C18	0.0201 (11)	0.0253 (11)	0.0361 (15)	0.0011 (9)	0.0141 (11)	0.0038 (10)
C19	0.0347 (13)	0.0267 (11)	0.0276 (13)	−0.0046 (10)	0.0165 (11)	0.0015 (10)
C20	0.0372 (14)	0.0202 (11)	0.0266 (13)	−0.0011 (10)	0.0120 (11)	0.0029 (9)
C21	0.0219 (11)	0.0209 (10)	0.0169 (11)	0.0007 (8)	0.0048 (9)	−0.0016 (8)
C22	0.0143 (10)	0.0172 (9)	0.0216 (12)	0.0001 (8)	0.0056 (9)	0.0005 (9)

Geometric parameters (Å, º) top

O1—C22	1.343 (5)	C3—H3A	0.9500
O1—C23	1.465 (3)	C4—C5	1.388 (3)
C23—C24	1.472 (4)	C4—C22	1.492 (3)
C23—H23A	0.9900	C5—C6	1.396 (3)
C23—H23B	0.9900	C5—H5A	0.9500
C24—H24A	0.9800	C7—C8	1.475 (3)
C24—H24B	0.9800	C8—C9	1.399 (3)
C24—H24C	0.9800	C8—C13	1.402 (3)
O1X—C22	1.34 (3)	C9—C10	1.386 (3)
O1X—C23X	1.478 (17)	C9—H9A	0.9500
C23X—C24X	1.446 (17)	C10—C11	1.392 (3)
C23X—H23C	0.9900	C10—C14	1.495 (3)
C23X—H23D	0.9900	C11—C12	1.388 (3)
C24X—H24D	0.9800	C11—H11A	0.9500
C24X—H24E	0.9800	C12—C13	1.390 (3)
C24X—H24F	0.9800	C12—H12A	0.9500
O2—C14	1.328 (2)	C13—H13A	0.9500
O2—H1O2	1.03 (4)	C15—C16	1.525 (3)
O3—C14	1.216 (2)	C15—H15A	0.9900
O4—C21	1.226 (2)	C15—H15B	0.9900
O5—C22	1.211 (2)	C16—C17	1.528 (3)
N1—C7	1.370 (2)	C16—H16A	0.9900
N1—C1	1.390 (2)	C16—H16B	0.9900
N1—C15	1.475 (2)	C17—H17A	0.9900
N2—C7	1.331 (2)	C17—H17B	0.9900
N2—C6	1.394 (2)	C18—C19	1.536 (3)
N3—C21	1.355 (3)	C18—H18A	0.9900
N3—C17	1.450 (3)	C18—H18B	0.9900
N3—C18	1.462 (3)	C19—C20	1.527 (3)
C1—C2	1.386 (3)	C19—H19A	0.9900
C1—C6	1.401 (3)	C19—H19B	0.9900
C2—C3	1.383 (3)	C20—C21	1.511 (3)
C2—H2A	0.9500	C20—H20A	0.9900
C3—C4	1.410 (3)	C20—H20B	0.9900

C22—O1—C23	116.1 (4)	C12—C11—C10	119.99 (19)
O1—C23—C24	111.4 (3)	C12—C11—H11A	120.0
O1—C23—H23A	109.3	C10—C11—H11A	120.0
C24—C23—H23A	109.3	C11—C12—C13	120.27 (19)
O1—C23—H23B	109.3	C11—C12—H12A	119.9
C24—C23—H23B	109.3	C13—C12—H12A	119.9
H23A—C23—H23B	108.0	C12—C13—C8	120.24 (19)
C22—O1X—C23X	117 (2)	C12—C13—H13A	119.9
C24X—C23X—O1X	103.0 (18)	C8—C13—H13A	119.9
C24X—C23X—H23C	111.2	O3—C14—O2	123.72 (19)
O1X—C23X—H23C	111.2	O3—C14—C10	122.72 (18)
C24X—C23X—H23D	111.2	O2—C14—C10	113.53 (17)
O1X—C23X—H23D	111.2	N1—C15—C16	113.28 (15)
H23C—C23X—H23D	109.1	N1—C15—H15A	108.9
C23X—C24X—H24D	109.5	C16—C15—H15A	108.9
C23X—C24X—H24E	109.5	N1—C15—H15B	108.9
H24D—C24X—H24E	109.5	C16—C15—H15B	108.9
C23X—C24X—H24F	109.5	H15A—C15—H15B	107.7
H24D—C24X—H24F	109.5	C15—C16—C17	110.36 (16)
H24E—C24X—H24F	109.5	C15—C16—H16A	109.6
C14—O2—H1O2	108.8 (19)	C17—C16—H16A	109.6
C7—N1—C1	106.81 (15)	C15—C16—H16B	109.6
C7—N1—C15	128.88 (16)	C17—C16—H16B	109.6
C1—N1—C15	123.18 (16)	H16A—C16—H16B	108.1
C7—N2—C6	105.04 (16)	N3—C17—C16	113.13 (17)
C21—N3—C17	123.25 (18)	N3—C17—H17A	109.0
C21—N3—C18	113.08 (17)	C16—C17—H17A	109.0
C17—N3—C18	121.13 (17)	N3—C17—H17B	109.0
C2—C1—N1	131.88 (18)	C16—C17—H17B	109.0
C2—C1—C6	122.52 (18)	H17A—C17—H17B	107.8
N1—C1—C6	105.60 (17)	N3—C18—C19	103.34 (17)
C3—C2—C1	116.74 (18)	N3—C18—H18A	111.1
C3—C2—H2A	121.6	C19—C18—H18A	111.1
C1—C2—H2A	121.6	N3—C18—H18B	111.1
C2—C3—C4	121.57 (19)	C19—C18—H18B	111.1
C2—C3—H3A	119.2	H18A—C18—H18B	109.1
C4—C3—H3A	119.2	C20—C19—C18	103.47 (18)
C5—C4—C3	121.29 (18)	C20—C19—H19A	111.1
C5—C4—C22	121.47 (18)	C18—C19—H19A	111.1
C3—C4—C22	117.23 (18)	C20—C19—H19B	111.1
C4—C5—C6	117.34 (18)	C18—C19—H19B	111.1
C4—C5—H5A	121.3	H19A—C19—H19B	109.0
C6—C5—H5A	121.3	C21—C20—C19	104.83 (17)
N2—C6—C5	129.66 (18)	C21—C20—H20A	110.8
N2—C6—C1	109.85 (17)	C19—C20—H20A	110.8
C5—C6—C1	120.48 (19)	C21—C20—H20B	110.8
N2—C7—N1	112.70 (17)	C19—C20—H20B	110.8
N2—C7—C8	122.94 (18)	H20A—C20—H20B	108.9
N1—C7—C8	124.36 (17)	O4—C21—N3	125.0 (2)
C9—C8—C13	118.74 (18)	O4—C21—C20	126.77 (19)
C9—C8—C7	118.40 (17)	N3—C21—C20	108.20 (18)
C13—C8—C7	122.84 (19)	O5—C22—O1X	120.1 (11)
C10—C9—C8	120.84 (18)	O5—C22—O1	124.7 (2)
C10—C9—H9A	119.6	O1X—C22—O1	20.7 (16)
C8—C9—H9A	119.6	O5—C22—C4	123.81 (19)
C9—C10—C11	119.84 (19)	O1X—C22—C4	113.4 (11)
C9—C10—C14	120.71 (17)	O1—C22—C4	111.4 (2)
C11—C10—C14	119.43 (18)

C22—O1—C23—C24	−90.3 (5)	C10—C11—C12—C13	−1.9 (3)
C22—O1X—C23X—C24X	−138 (3)	C11—C12—C13—C8	0.0 (3)
C7—N1—C1—C2	179.4 (2)	C9—C8—C13—C12	2.4 (3)
C15—N1—C1—C2	−11.8 (3)	C7—C8—C13—C12	−179.14 (18)
C7—N1—C1—C6	−0.3 (2)	C9—C10—C14—O3	−177.43 (18)
C15—N1—C1—C6	168.44 (16)	C11—C10—C14—O3	1.2 (3)
N1—C1—C2—C3	−179.75 (19)	C9—C10—C14—O2	0.5 (3)
C6—C1—C2—C3	0.0 (3)	C11—C10—C14—O2	179.16 (17)
C1—C2—C3—C4	−1.5 (3)	C7—N1—C15—C16	−113.5 (2)
C2—C3—C4—C5	1.2 (3)	C1—N1—C15—C16	80.4 (2)
C2—C3—C4—C22	−178.28 (18)	N1—C15—C16—C17	178.68 (17)
C3—C4—C5—C6	0.8 (3)	C21—N3—C17—C16	120.6 (2)
C22—C4—C5—C6	−179.84 (17)	C18—N3—C17—C16	−78.7 (2)
C7—N2—C6—C5	178.0 (2)	C15—C16—C17—N3	−65.6 (2)
C7—N2—C6—C1	−1.1 (2)	C21—N3—C18—C19	−20.0 (2)
C4—C5—C6—N2	178.75 (18)	C17—N3—C18—C19	177.57 (18)
C4—C5—C6—C1	−2.2 (3)	N3—C18—C19—C20	26.0 (2)
C2—C1—C6—N2	−178.87 (17)	C18—C19—C20—C21	−23.6 (2)
N1—C1—C6—N2	0.9 (2)	C17—N3—C21—O4	−11.8 (3)
C2—C1—C6—C5	2.0 (3)	C18—N3—C21—O4	−173.9 (2)
N1—C1—C6—C5	−178.27 (17)	C17—N3—C21—C20	166.91 (18)
C6—N2—C7—N1	0.9 (2)	C18—N3—C21—C20	4.9 (2)
C6—N2—C7—C8	−179.02 (17)	C19—C20—C21—O4	−168.8 (2)
C1—N1—C7—N2	−0.4 (2)	C19—C20—C21—N3	12.5 (2)
C15—N1—C7—N2	−168.29 (17)	C23X—O1X—C22—O5	18 (3)
C1—N1—C7—C8	179.56 (17)	C23X—O1X—C22—O1	−91 (4)
C15—N1—C7—C8	11.6 (3)	C23X—O1X—C22—C4	−179.9 (15)
N2—C7—C8—C9	35.6 (3)	C23—O1—C22—O5	−1.6 (4)
N1—C7—C8—C9	−144.28 (19)	C23—O1—C22—O1X	82 (4)
N2—C7—C8—C13	−142.87 (19)	C23—O1—C22—C4	−177.9 (2)
N1—C7—C8—C13	37.2 (3)	C5—C4—C22—O5	156.8 (2)
C13—C8—C9—C10	−2.8 (3)	C3—C4—C22—O5	−23.7 (3)
C7—C8—C9—C10	178.65 (17)	C5—C4—C22—O1X	−4.5 (18)
C8—C9—C10—C11	0.9 (3)	C3—C4—C22—O1X	174.9 (18)
C8—C9—C10—C14	179.48 (17)	C5—C4—C22—O1	−26.8 (3)
C9—C10—C11—C12	1.5 (3)	C3—C4—C22—O1	152.6 (2)
C14—C10—C11—C12	−177.12 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N2ⁱ	1.04 (4)	1.66 (4)	2.675 (2)	166 (3)
C5—H5A···O3ⁱ	0.95	2.57	3.367 (2)	141
C9—H9A···O2ⁱ	0.95	2.46	3.177 (2)	132
C15—H15A···O3ⁱⁱ	0.99	2.34	3.314 (3)	167
C17—H17B···O5ⁱⁱⁱ	0.99	2.51	3.429 (3)	154
C20—H20B···O4^iv	0.99	2.55	3.340 (3)	137

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₅N₃O₅
M_r	435.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.3097 (3), 24.8252 (7), 9.6761 (3)
β (°)	112.322 (1)
V (Å³)	2068.71 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.39 × 0.23 × 0.08

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.963, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	23636, 6010, 3706
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.134, 1.03
No. of reflections	6010
No. of parameters	317
No. of restraints	69
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.31

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
O2—H1O2···N2ⁱ	1.04 (4)	1.66 (4)	2.675 (2)	166 (3)
C5—H5A···O3ⁱ	0.95	2.57	3.367 (2)	141
C9—H9A···O2ⁱ	0.95	2.46	3.177 (2)	132
C15—H15A···O3ⁱⁱ	0.99	2.34	3.314 (3)	167
C17—H17B···O5ⁱⁱⁱ	0.99	2.51	3.429 (3)	154
C20—H20B···O4^iv	0.99	2.55	3.340 (3)	137

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

Acknowledgements

The authors thank the Pharmacogenetics and Novel Therapeutics Research Cluster, Institute for Research in Molecular Medicine, Universiti Sains Malaysia (USM), Penang, for supporting this work. This work was funded through Research Grant (RUC) No. 1001/PSK/8620012 and HiCoE Research Grant No. 311.CIPPM.4401005. IAR also thanks USM for the Research University Grant No. 1001/PFIZIK/811151.

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
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., Choon, T. S., Asik, S. I. J. & Razak, I. A. (2012). Acta Cryst. E68, o59. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 69| Part 2| February 2013| Page o304

doi:10.1107/S1600536813001116

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

3-{5-Eth­­oxy­carbonyl-1-[3-(2-oxopyrrol­idin-1-yl)prop­yl]-1H-benzimidazol-2-yl}benzoic acid

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-{5-Ethoxycarbonyl-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-benzimidazol-2-yl}benzoic acid