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

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ISSN: 2056-9890

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

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[Yoon, Y. K., Ali, M. A., Choon, T. S., Asik, S. I. J. & Razak, I. A. (2012). Acta Cryst. E68, o59.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C24H25N3O5

  • Mr = 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.963, Tmax = 0.992

  • 23636 measured reflections

  • 6010 independent reflections

  • 3706 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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⋯O4iv 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


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.

Refinement top

O bound H atoms were located from a difference Fourier maps and freely refined. The remaining H atoms were positioned geometrically and refined using a riding model with C—H = 0.95–0.99 Å and Uiso(H) = 1.2Ueq(C) and 1.5Ueq(C-methyl). The ethoxy group disordered over two postion with the final refine occupancies 0.853 (14):0.147 (14). A rigid bond and similar restraint were applied for the disordered component. The same anisotropic displacement are used for the C23X and C24X.

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
[Figure 1] Fig. 1. The structure of the title compound, showing 50% probability displacement ellipsoids.
[Figure 2] 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
C24H25N3O5F(000) = 920
Mr = 435.47Dx = 1.398 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3829 reflections
a = 9.3097 (3) Åθ = 2.4–29.4°
b = 24.8252 (7) ŵ = 0.10 mm1
c = 9.6761 (3) ÅT = 100 K
β = 112.322 (1)°Plate, brown
V = 2068.71 (11) Å30.39 × 0.23 × 0.08 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD
diffractometer
6010 independent reflections
Radiation source: fine-focus sealed tube3706 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.065
ϕ and ω scansθmax = 30.1°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1313
Tmin = 0.963, Tmax = 0.992k = 3434
23636 measured reflectionsl = 813
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0444P)2 + 0.6946P]
where P = (Fo2 + 2Fc2)/3
6010 reflections(Δ/σ)max = 0.001
317 parametersΔρmax = 0.37 e Å3
69 restraintsΔρmin = 0.31 e Å3
Crystal data top
C24H25N3O5V = 2068.71 (11) Å3
Mr = 435.47Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.3097 (3) ŵ = 0.10 mm1
b = 24.8252 (7) ÅT = 100 K
c = 9.6761 (3) Å0.39 × 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)
Tmin = 0.963, Tmax = 0.992Rint = 0.065
23636 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06469 restraints
wR(F2) = 0.134H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.37 e Å3
6010 reflectionsΔρmin = 0.31 e Å3
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
xyzUiso*/UeqOcc. (<1)
O10.1036 (4)0.15612 (14)0.1235 (6)0.0179 (7)0.853 (14)
C230.1927 (4)0.20029 (16)0.1526 (4)0.0216 (8)0.853 (14)
H23A0.30360.19640.08680.026*0.853 (14)
H23B0.18470.19830.25750.026*0.853 (14)
C240.1357 (4)0.25307 (15)0.1261 (8)0.0427 (14)0.853 (14)
H24A0.19860.28170.14480.064*0.853 (14)
H24B0.02700.25750.19350.064*0.853 (14)
H24C0.14370.25510.02230.064*0.853 (14)
O1X0.066 (4)0.1693 (10)0.123 (4)0.043 (6)0.147 (14)
C23X0.148 (5)0.2161 (11)0.153 (3)0.054 (5)0.147 (14)
H23C0.10180.22680.25910.064*0.147 (14)
H23D0.25980.20800.12590.064*0.147 (14)
C24X0.127 (4)0.2575 (9)0.057 (3)0.054 (5)0.147 (14)
H24D0.15220.29270.08790.080*0.147 (14)
H24E0.01850.25750.06570.080*0.147 (14)
H24F0.19520.25040.04660.080*0.147 (14)
O20.02946 (16)0.06006 (5)0.61398 (17)0.0181 (3)
O30.12028 (16)0.11302 (5)0.69174 (16)0.0201 (3)
O40.43579 (19)0.23361 (6)0.23971 (19)0.0333 (4)
O50.06150 (17)0.15773 (6)0.36566 (17)0.0231 (3)
N10.30457 (18)0.03432 (6)0.07554 (19)0.0142 (3)
N20.17804 (18)0.02457 (6)0.10670 (19)0.0147 (4)
N30.61523 (19)0.17298 (6)0.2256 (2)0.0184 (4)
C10.2460 (2)0.00527 (7)0.1413 (2)0.0135 (4)
C20.2562 (2)0.01238 (8)0.2868 (2)0.0145 (4)
H2A0.31060.01240.36380.017*
C30.1832 (2)0.05727 (7)0.3144 (2)0.0151 (4)
H3A0.18970.06400.41330.018*
C40.0994 (2)0.09329 (7)0.1994 (2)0.0147 (4)
C50.0890 (2)0.08568 (8)0.0537 (2)0.0158 (4)
H5A0.03150.10970.02400.019*
C60.1663 (2)0.04131 (7)0.0261 (2)0.0139 (4)
C70.2601 (2)0.02085 (7)0.0722 (2)0.0139 (4)
C80.2977 (2)0.05271 (7)0.1826 (2)0.0145 (4)
C90.1876 (2)0.05557 (7)0.3289 (2)0.0148 (4)
H9A0.09240.03650.35480.018*
C100.2155 (2)0.08584 (7)0.4364 (2)0.0148 (4)
C110.3555 (2)0.11325 (8)0.3997 (2)0.0178 (4)
H11A0.37390.13470.47250.021*
C120.4683 (2)0.10921 (8)0.2565 (2)0.0185 (4)
H12A0.56500.12710.23250.022*
C130.4402 (2)0.07915 (8)0.1481 (2)0.0177 (4)
H13A0.51790.07650.05040.021*
C140.0980 (2)0.08844 (7)0.5930 (2)0.0153 (4)
C150.3717 (2)0.08531 (7)0.1508 (2)0.0155 (4)
H15A0.30730.09890.20440.019*
H15B0.36790.11230.07420.019*
C160.5390 (2)0.07964 (8)0.2613 (2)0.0176 (4)
H16A0.60420.06560.20900.021*
H16B0.54350.05360.34040.021*
C170.6019 (3)0.13412 (8)0.3320 (2)0.0212 (5)
H17A0.53220.14890.37860.025*
H17B0.70540.12870.41210.025*
C180.7451 (3)0.17112 (9)0.1760 (3)0.0262 (5)
H18A0.74940.13600.12930.031*
H18B0.84510.17740.26040.031*
C190.7087 (3)0.21703 (9)0.0613 (3)0.0283 (5)
H19A0.80510.23480.06450.034*
H19B0.65050.20360.04110.034*
C200.6095 (3)0.25556 (8)0.1106 (3)0.0280 (5)
H20A0.67400.28460.17430.034*
H20B0.52690.27200.02300.034*
C210.5400 (2)0.22093 (8)0.1978 (2)0.0206 (5)
C220.0213 (2)0.13958 (8)0.2405 (2)0.0181 (4)
H1O20.085 (4)0.0523 (13)0.727 (4)0.088 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0142 (12)0.0183 (13)0.0183 (12)0.0053 (9)0.0027 (10)0.0015 (11)
C230.0192 (16)0.0166 (16)0.0258 (16)0.0079 (11)0.0050 (13)0.0021 (12)
C240.0372 (19)0.0253 (16)0.064 (4)0.0002 (13)0.018 (2)0.0081 (19)
O1X0.062 (15)0.034 (9)0.021 (8)0.021 (9)0.004 (11)0.003 (9)
C23X0.090 (13)0.025 (8)0.054 (10)0.008 (8)0.037 (10)0.004 (8)
C24X0.090 (13)0.025 (8)0.054 (10)0.008 (8)0.037 (10)0.004 (8)
O20.0158 (7)0.0229 (7)0.0141 (8)0.0050 (6)0.0041 (6)0.0017 (6)
O30.0208 (7)0.0225 (7)0.0168 (8)0.0016 (6)0.0069 (6)0.0022 (6)
O40.0335 (9)0.0364 (9)0.0320 (11)0.0089 (7)0.0148 (8)0.0014 (8)
O50.0236 (8)0.0253 (8)0.0175 (8)0.0030 (6)0.0047 (7)0.0059 (6)
N10.0123 (8)0.0176 (8)0.0125 (9)0.0010 (6)0.0045 (7)0.0019 (7)
N20.0119 (8)0.0194 (8)0.0115 (9)0.0008 (6)0.0029 (7)0.0002 (7)
N30.0173 (9)0.0187 (8)0.0185 (10)0.0009 (7)0.0060 (8)0.0018 (7)
C10.0100 (9)0.0159 (9)0.0143 (10)0.0005 (7)0.0042 (8)0.0003 (8)
C20.0134 (9)0.0174 (9)0.0113 (10)0.0008 (7)0.0031 (8)0.0002 (7)
C30.0132 (9)0.0192 (10)0.0132 (10)0.0017 (8)0.0053 (8)0.0028 (8)
C40.0124 (9)0.0169 (9)0.0144 (10)0.0010 (7)0.0046 (8)0.0011 (8)
C50.0120 (9)0.0178 (9)0.0159 (11)0.0001 (7)0.0033 (8)0.0019 (8)
C60.0122 (9)0.0183 (9)0.0097 (10)0.0015 (7)0.0024 (8)0.0003 (8)
C70.0105 (9)0.0166 (9)0.0128 (10)0.0021 (7)0.0026 (8)0.0002 (8)
C80.0146 (10)0.0172 (9)0.0130 (10)0.0014 (7)0.0067 (8)0.0001 (8)
C90.0125 (9)0.0162 (9)0.0156 (11)0.0004 (7)0.0052 (8)0.0014 (8)
C100.0154 (9)0.0154 (9)0.0139 (10)0.0018 (7)0.0058 (8)0.0010 (8)
C110.0178 (10)0.0206 (10)0.0177 (11)0.0034 (8)0.0096 (9)0.0018 (8)
C120.0151 (10)0.0234 (10)0.0180 (11)0.0038 (8)0.0076 (9)0.0011 (9)
C130.0145 (10)0.0223 (10)0.0145 (11)0.0004 (8)0.0036 (9)0.0009 (8)
C140.0160 (10)0.0154 (9)0.0152 (11)0.0010 (8)0.0066 (9)0.0007 (8)
C150.0168 (10)0.0145 (9)0.0158 (11)0.0007 (8)0.0069 (9)0.0024 (8)
C160.0175 (10)0.0176 (10)0.0149 (11)0.0006 (8)0.0032 (9)0.0007 (8)
C170.0256 (11)0.0217 (10)0.0130 (11)0.0055 (9)0.0037 (9)0.0013 (8)
C180.0201 (11)0.0253 (11)0.0361 (15)0.0011 (9)0.0141 (11)0.0038 (10)
C190.0347 (13)0.0267 (11)0.0276 (13)0.0046 (10)0.0165 (11)0.0015 (10)
C200.0372 (14)0.0202 (11)0.0266 (13)0.0011 (10)0.0120 (11)0.0029 (9)
C210.0219 (11)0.0209 (10)0.0169 (11)0.0007 (8)0.0048 (9)0.0016 (8)
C220.0143 (10)0.0172 (9)0.0216 (12)0.0001 (8)0.0056 (9)0.0005 (9)
Geometric parameters (Å, º) top
O1—C221.343 (5)C3—H3A0.9500
O1—C231.465 (3)C4—C51.388 (3)
C23—C241.472 (4)C4—C221.492 (3)
C23—H23A0.9900C5—C61.396 (3)
C23—H23B0.9900C5—H5A0.9500
C24—H24A0.9800C7—C81.475 (3)
C24—H24B0.9800C8—C91.399 (3)
C24—H24C0.9800C8—C131.402 (3)
O1X—C221.34 (3)C9—C101.386 (3)
O1X—C23X1.478 (17)C9—H9A0.9500
C23X—C24X1.446 (17)C10—C111.392 (3)
C23X—H23C0.9900C10—C141.495 (3)
C23X—H23D0.9900C11—C121.388 (3)
C24X—H24D0.9800C11—H11A0.9500
C24X—H24E0.9800C12—C131.390 (3)
C24X—H24F0.9800C12—H12A0.9500
O2—C141.328 (2)C13—H13A0.9500
O2—H1O21.03 (4)C15—C161.525 (3)
O3—C141.216 (2)C15—H15A0.9900
O4—C211.226 (2)C15—H15B0.9900
O5—C221.211 (2)C16—C171.528 (3)
N1—C71.370 (2)C16—H16A0.9900
N1—C11.390 (2)C16—H16B0.9900
N1—C151.475 (2)C17—H17A0.9900
N2—C71.331 (2)C17—H17B0.9900
N2—C61.394 (2)C18—C191.536 (3)
N3—C211.355 (3)C18—H18A0.9900
N3—C171.450 (3)C18—H18B0.9900
N3—C181.462 (3)C19—C201.527 (3)
C1—C21.386 (3)C19—H19A0.9900
C1—C61.401 (3)C19—H19B0.9900
C2—C31.383 (3)C20—C211.511 (3)
C2—H2A0.9500C20—H20A0.9900
C3—C41.410 (3)C20—H20B0.9900
C22—O1—C23116.1 (4)C12—C11—C10119.99 (19)
O1—C23—C24111.4 (3)C12—C11—H11A120.0
O1—C23—H23A109.3C10—C11—H11A120.0
C24—C23—H23A109.3C11—C12—C13120.27 (19)
O1—C23—H23B109.3C11—C12—H12A119.9
C24—C23—H23B109.3C13—C12—H12A119.9
H23A—C23—H23B108.0C12—C13—C8120.24 (19)
C22—O1X—C23X117 (2)C12—C13—H13A119.9
C24X—C23X—O1X103.0 (18)C8—C13—H13A119.9
C24X—C23X—H23C111.2O3—C14—O2123.72 (19)
O1X—C23X—H23C111.2O3—C14—C10122.72 (18)
C24X—C23X—H23D111.2O2—C14—C10113.53 (17)
O1X—C23X—H23D111.2N1—C15—C16113.28 (15)
H23C—C23X—H23D109.1N1—C15—H15A108.9
C23X—C24X—H24D109.5C16—C15—H15A108.9
C23X—C24X—H24E109.5N1—C15—H15B108.9
H24D—C24X—H24E109.5C16—C15—H15B108.9
C23X—C24X—H24F109.5H15A—C15—H15B107.7
H24D—C24X—H24F109.5C15—C16—C17110.36 (16)
H24E—C24X—H24F109.5C15—C16—H16A109.6
C14—O2—H1O2108.8 (19)C17—C16—H16A109.6
C7—N1—C1106.81 (15)C15—C16—H16B109.6
C7—N1—C15128.88 (16)C17—C16—H16B109.6
C1—N1—C15123.18 (16)H16A—C16—H16B108.1
C7—N2—C6105.04 (16)N3—C17—C16113.13 (17)
C21—N3—C17123.25 (18)N3—C17—H17A109.0
C21—N3—C18113.08 (17)C16—C17—H17A109.0
C17—N3—C18121.13 (17)N3—C17—H17B109.0
C2—C1—N1131.88 (18)C16—C17—H17B109.0
C2—C1—C6122.52 (18)H17A—C17—H17B107.8
N1—C1—C6105.60 (17)N3—C18—C19103.34 (17)
C3—C2—C1116.74 (18)N3—C18—H18A111.1
C3—C2—H2A121.6C19—C18—H18A111.1
C1—C2—H2A121.6N3—C18—H18B111.1
C2—C3—C4121.57 (19)C19—C18—H18B111.1
C2—C3—H3A119.2H18A—C18—H18B109.1
C4—C3—H3A119.2C20—C19—C18103.47 (18)
C5—C4—C3121.29 (18)C20—C19—H19A111.1
C5—C4—C22121.47 (18)C18—C19—H19A111.1
C3—C4—C22117.23 (18)C20—C19—H19B111.1
C4—C5—C6117.34 (18)C18—C19—H19B111.1
C4—C5—H5A121.3H19A—C19—H19B109.0
C6—C5—H5A121.3C21—C20—C19104.83 (17)
N2—C6—C5129.66 (18)C21—C20—H20A110.8
N2—C6—C1109.85 (17)C19—C20—H20A110.8
C5—C6—C1120.48 (19)C21—C20—H20B110.8
N2—C7—N1112.70 (17)C19—C20—H20B110.8
N2—C7—C8122.94 (18)H20A—C20—H20B108.9
N1—C7—C8124.36 (17)O4—C21—N3125.0 (2)
C9—C8—C13118.74 (18)O4—C21—C20126.77 (19)
C9—C8—C7118.40 (17)N3—C21—C20108.20 (18)
C13—C8—C7122.84 (19)O5—C22—O1X120.1 (11)
C10—C9—C8120.84 (18)O5—C22—O1124.7 (2)
C10—C9—H9A119.6O1X—C22—O120.7 (16)
C8—C9—H9A119.6O5—C22—C4123.81 (19)
C9—C10—C11119.84 (19)O1X—C22—C4113.4 (11)
C9—C10—C14120.71 (17)O1—C22—C4111.4 (2)
C11—C10—C14119.43 (18)
C22—O1—C23—C2490.3 (5)C10—C11—C12—C131.9 (3)
C22—O1X—C23X—C24X138 (3)C11—C12—C13—C80.0 (3)
C7—N1—C1—C2179.4 (2)C9—C8—C13—C122.4 (3)
C15—N1—C1—C211.8 (3)C7—C8—C13—C12179.14 (18)
C7—N1—C1—C60.3 (2)C9—C10—C14—O3177.43 (18)
C15—N1—C1—C6168.44 (16)C11—C10—C14—O31.2 (3)
N1—C1—C2—C3179.75 (19)C9—C10—C14—O20.5 (3)
C6—C1—C2—C30.0 (3)C11—C10—C14—O2179.16 (17)
C1—C2—C3—C41.5 (3)C7—N1—C15—C16113.5 (2)
C2—C3—C4—C51.2 (3)C1—N1—C15—C1680.4 (2)
C2—C3—C4—C22178.28 (18)N1—C15—C16—C17178.68 (17)
C3—C4—C5—C60.8 (3)C21—N3—C17—C16120.6 (2)
C22—C4—C5—C6179.84 (17)C18—N3—C17—C1678.7 (2)
C7—N2—C6—C5178.0 (2)C15—C16—C17—N365.6 (2)
C7—N2—C6—C11.1 (2)C21—N3—C18—C1920.0 (2)
C4—C5—C6—N2178.75 (18)C17—N3—C18—C19177.57 (18)
C4—C5—C6—C12.2 (3)N3—C18—C19—C2026.0 (2)
C2—C1—C6—N2178.87 (17)C18—C19—C20—C2123.6 (2)
N1—C1—C6—N20.9 (2)C17—N3—C21—O411.8 (3)
C2—C1—C6—C52.0 (3)C18—N3—C21—O4173.9 (2)
N1—C1—C6—C5178.27 (17)C17—N3—C21—C20166.91 (18)
C6—N2—C7—N10.9 (2)C18—N3—C21—C204.9 (2)
C6—N2—C7—C8179.02 (17)C19—C20—C21—O4168.8 (2)
C1—N1—C7—N20.4 (2)C19—C20—C21—N312.5 (2)
C15—N1—C7—N2168.29 (17)C23X—O1X—C22—O518 (3)
C1—N1—C7—C8179.56 (17)C23X—O1X—C22—O191 (4)
C15—N1—C7—C811.6 (3)C23X—O1X—C22—C4179.9 (15)
N2—C7—C8—C935.6 (3)C23—O1—C22—O51.6 (4)
N1—C7—C8—C9144.28 (19)C23—O1—C22—O1X82 (4)
N2—C7—C8—C13142.87 (19)C23—O1—C22—C4177.9 (2)
N1—C7—C8—C1337.2 (3)C5—C4—C22—O5156.8 (2)
C13—C8—C9—C102.8 (3)C3—C4—C22—O523.7 (3)
C7—C8—C9—C10178.65 (17)C5—C4—C22—O1X4.5 (18)
C8—C9—C10—C110.9 (3)C3—C4—C22—O1X174.9 (18)
C8—C9—C10—C14179.48 (17)C5—C4—C22—O126.8 (3)
C9—C10—C11—C121.5 (3)C3—C4—C22—O1152.6 (2)
C14—C10—C11—C12177.12 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1O2···N2i1.04 (4)1.66 (4)2.675 (2)166 (3)
C5—H5A···O3i0.952.573.367 (2)141
C9—H9A···O2i0.952.463.177 (2)132
C15—H15A···O3ii0.992.343.314 (3)167
C17—H17B···O5iii0.992.513.429 (3)154
C20—H20B···O4iv0.992.553.340 (3)137
Symmetry codes: (i) x, y, z1; (ii) x, y, z+1; (iii) x+1, y, z+1; (iv) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC24H25N3O5
Mr435.47
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)9.3097 (3), 24.8252 (7), 9.6761 (3)
β (°) 112.322 (1)
V3)2068.71 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.39 × 0.23 × 0.08
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.963, 0.992
No. of measured, independent and
observed [I > 2σ(I)] reflections
23636, 6010, 3706
Rint0.065
(sin θ/λ)max1)0.705
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.134, 1.03
No. of reflections6010
No. of parameters317
No. of restraints69
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O2—H1O2···N2i1.04 (4)1.66 (4)2.675 (2)166 (3)
C5—H5A···O3i0.952.573.367 (2)141
C9—H9A···O2i0.952.463.177 (2)132
C15—H15A···O3ii0.992.343.314 (3)167
C17—H17B···O5iii0.992.513.429 (3)154
C20—H20B···O4iv0.992.553.340 (3)137
Symmetry codes: (i) x, y, z1; (ii) x, y, z+1; (iii) x+1, y, z+1; (iv) x, y+1/2, z1/2.
 

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

First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.  CrossRef CAS Web of Science IUCr Journals
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals
First citationYoon, 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

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