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Acta Crystallogr Sect E Struct Rep Online. 2012 February 1; 68(Pt 2): o251–o252.
Published online 2012 January 7. doi:  10.1107/S1600536811054833
PMCID: PMC3274946

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

Abstract

In the title compound, C23H25N3O3, the benzimidazole ring system is essentially planar [maximum deviation = 0.0240 (18) Å]. The mean plane through this ring system forms a dihedral angle of 42.23 (7)° with the benzene ring. The pyrrolidine ring is in an envelope conformation with the flap atom disordered over two sites with occupancies of 0.813 (11) and 0.187 (11). In the crystal, weak C—H(...)O hydrogen bonds form R 2 2(10) ring motifs, which are connected by further C—H(...)O inter­actions, forming ribbons along the b axis. The crystal structure is further stabilized by weak π–π inter­actions involving the imidazole and benzene rings of the benzimidazole ring system [centroid–centroid distances = 3.6788 (11) and 3.6316 (10) Å] and weak C—H(...)π inter­actions.

Related literature

For the biological activity of benzimidazole derivatives, see: Ozden et al. (2008 [triangle]); Garuti et al. (2000 [triangle]); Rao et al. (2002 [triangle]); Thakurdesai et al. (2007 [triangle]). For ring conformations, see: Cremer & Pople (1975 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-68-0o251-scheme1.jpg

Experimental

Crystal data

  • C23H25N3O3
  • M r = 391.46
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-68-0o251-efi1.jpg
  • a = 9.9469 (3) Å
  • b = 10.5845 (3) Å
  • c = 11.3184 (3) Å
  • α = 69.679 (1)°
  • β = 67.374 (1)°
  • γ = 70.135 (1)°
  • V = 1001.77 (5) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 K
  • 0.39 × 0.36 × 0.25 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.967, T max = 0.979
  • 17976 measured reflections
  • 4530 independent reflections
  • 3768 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.148
  • S = 1.04
  • 4530 reflections
  • 273 parameters
  • H-atom parameters constrained
  • Δρmax = 0.48 e Å−3
  • Δρmin = −0.29 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811054833/lh5398sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054833/lh5398Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811054833/lh5398Isup3.cml

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

Acknowledgments

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, Penang.

supplementary crystallographic information

Comment

Benzimidazoles are a class of bioactive heterocyclic compounds which exhibit a wide range of activities such as antibacterial (Ozden et al., 2008), antiproliferatives (Garuti et al., 2000), anti-HIV (Rao et al., 2002) and anti-inflammatory (Thakurdesai et al., 2007). In view of their importance, the crystal structure determination of the title compound was carried out and the results are presented here.

In the title molecule, Fig. 1, the benzimidazole, (N1–N2/C1–C7) ring is essentially planar with maximum deviation of 0.0240 (18) Å for atom C5. The mean plane through this ring makes a dihedral angle of 42.23 (7)° with the benzene, (C8–C13) ring. Atom C21 is disordered (Fig. 1) over two positions, with occupancy ratios of 0.813 (11):0.187 (11). The disordered pyrrolidine ring adopts an envelope conformation with puckering parameters Q = 0.2836 Å, [var phi] = 249.7429° with C21 at the flap and Q = 0.2163 Å, [var phi] = 77.1714° with C21X at the flap (Cremer & Pople, 1975).

In the crystal packing (Fig. 2), R22(10) ring motifs (Bernstein et al., 1995) are formed by C19—H19B···O3(1-x,-1-y,1-z) intermolecular interactions. C5—H5A···O3(1-x,-1-y,1-z) and C16—H16B···O3 (1-x,-y,1-z) interactions further link the molecules into ribbon along the b axis. π–π stacking interactions are observed within the benzimidazole ring system between the imadazole (N1–N2/C1/C6–C7); centroid Cg1) and the benzene (C1–C6; centroid Cg2) rings with a Cg1···Cg2 (1-x,-y,1-z) distance of 3.6788 (11) and between the benzene rings with a Cg2···Cg2(1-x,-y,1-z) distance of 3.6316 (10). The crystal packing is further stabilized by weak C—H···π interactions (Table 1).

Experimental

Ethyl 3-amino-4-(3(2-oxopyrrolidin-1yl)propylamino)benzoate (0.84 mmol) and sodium metabisulfite adduct of 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 recrystallised from Ethyl acetate.

Refinement

All H atoms positioned geometrically and refined using a riding model with with C–H = 0.95–0.99 Å. The Uiso values were constrained to be 1.5Ueq (methyl-H atom) and 1.2Ueq (other H atoms). The rotating model group was applied for the methyl group.

Figures

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

Crystal data

C23H25N3O3Z = 2
Mr = 391.46F(000) = 416
Triclinic, P1Dx = 1.298 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.9469 (3) ÅCell parameters from 8488 reflections
b = 10.5845 (3) Åθ = 2.5–30.0°
c = 11.3184 (3) ŵ = 0.09 mm1
α = 69.679 (1)°T = 100 K
β = 67.374 (1)°Block, yellow
γ = 70.135 (1)°0.39 × 0.36 × 0.25 mm
V = 1001.77 (5) Å3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer4530 independent reflections
Radiation source: fine-focus sealed tube3768 reflections with I > 2σ(I)
graphiteRint = 0.038
[var phi] and ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −12→12
Tmin = 0.967, Tmax = 0.979k = −13→13
17976 measured reflectionsl = −14→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0797P)2 + 0.518P] where P = (Fo2 + 2Fc2)/3
4530 reflections(Δ/σ)max < 0.001
273 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = −0.29 e Å3

Special details

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)

xyzUiso*/UeqOcc. (<1)
O10.51811 (13)0.43185 (12)0.18372 (11)0.0238 (3)
O20.72338 (14)0.26966 (13)0.11427 (12)0.0278 (3)
O30.38369 (15)−0.62929 (14)0.65226 (14)0.0336 (3)
N10.16338 (15)0.14323 (14)0.56013 (13)0.0183 (3)
N20.25147 (15)−0.07610 (14)0.53712 (13)0.0173 (3)
N30.17813 (16)−0.48401 (14)0.59087 (14)0.0223 (3)
C10.29539 (17)0.13446 (17)0.45592 (15)0.0175 (3)
C20.37149 (18)0.23727 (17)0.37207 (15)0.0180 (3)
H2A0.33290.33050.37940.022*
C30.50599 (18)0.19825 (17)0.27734 (15)0.0190 (3)
C40.56275 (18)0.05964 (17)0.26704 (15)0.0197 (3)
H4A0.65610.03590.20280.024*
C50.48733 (18)−0.04269 (17)0.34713 (15)0.0192 (3)
H5A0.5251−0.13560.33880.023*
C60.35264 (18)−0.00195 (17)0.44091 (15)0.0173 (3)
C70.14155 (17)0.01636 (17)0.60518 (15)0.0178 (3)
C80.01066 (17)−0.01765 (16)0.71822 (15)0.0182 (3)
C9−0.07626 (18)−0.09810 (17)0.71996 (16)0.0201 (3)
H9A−0.0472−0.14010.64930.024*
C10−0.20564 (19)−0.11690 (18)0.82509 (16)0.0235 (4)
H10A−0.2640−0.17230.82620.028*
C11−0.24936 (19)−0.05501 (19)0.92789 (17)0.0254 (4)
H11A−0.3375−0.06810.99950.030*
C12−0.1640 (2)0.02624 (19)0.92607 (17)0.0251 (4)
H12A−0.19430.06960.99600.030*
C13−0.03462 (19)0.04401 (17)0.82207 (16)0.0212 (3)
H13A0.02380.09900.82170.025*
C140.59541 (18)0.30010 (17)0.18400 (15)0.0198 (3)
C150.5951 (2)0.53843 (19)0.08991 (17)0.0267 (4)
H15A0.62700.5271−0.00090.032*
H15B0.68520.53170.11150.032*
C160.4870 (2)0.6758 (2)0.09972 (18)0.0315 (4)
H16A0.52930.74940.02850.047*
H16B0.46860.69210.18530.047*
H16C0.39230.67580.09180.047*
C170.26948 (18)−0.22474 (16)0.55756 (15)0.0179 (3)
H17A0.2068−0.26200.64750.021*
H17B0.3754−0.27370.55090.021*
C180.22422 (18)−0.25223 (16)0.45568 (15)0.0189 (3)
H18A0.1154−0.21210.46930.023*
H18B0.2782−0.20500.36590.023*
C190.25864 (19)−0.40646 (17)0.46449 (16)0.0212 (3)
H19A0.2324−0.41750.39330.025*
H19B0.3677−0.44610.44950.025*
C200.0140 (2)−0.45478 (19)0.64291 (19)0.0285 (4)
H20A−0.0309−0.43590.57240.034*0.813 (11)
H20B−0.0264−0.37410.68210.034*0.813 (11)
H20C−0.0269−0.47250.58770.034*0.187 (11)
H20D−0.0269−0.35960.64700.034*0.187 (11)
C21−0.0168 (3)−0.5853 (3)0.7469 (3)0.0277 (8)0.813 (11)
H21A−0.0297−0.65060.70940.033*0.813 (11)
H21B−0.1075−0.56430.82120.033*0.813 (11)
C21X−0.0012 (16)−0.5530 (18)0.7962 (18)0.049 (5)0.187 (11)
H21C−0.0217−0.49570.85690.059*0.187 (11)
H21D−0.0842−0.59960.82750.059*0.187 (11)
C220.1275 (2)−0.6456 (2)0.7924 (2)0.0345 (5)
H22A0.1139−0.61360.86960.041*0.813 (11)
H22B0.1533−0.74830.81580.041*0.813 (11)
H22C0.1333−0.73850.79370.041*0.187 (11)
H22D0.1447−0.64890.87140.041*0.187 (11)
C230.2473 (2)−0.58904 (18)0.67283 (18)0.0257 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0232 (6)0.0232 (6)0.0213 (6)−0.0115 (5)−0.0019 (5)−0.0008 (5)
O20.0200 (6)0.0320 (7)0.0274 (6)−0.0106 (5)−0.0004 (5)−0.0060 (5)
O30.0287 (7)0.0256 (7)0.0471 (8)−0.0023 (6)−0.0203 (6)−0.0037 (6)
N10.0162 (7)0.0205 (7)0.0176 (6)−0.0064 (5)−0.0046 (5)−0.0026 (5)
N20.0160 (7)0.0189 (7)0.0168 (6)−0.0057 (5)−0.0051 (5)−0.0028 (5)
N30.0185 (7)0.0178 (7)0.0285 (7)−0.0053 (5)−0.0064 (6)−0.0033 (6)
C10.0144 (7)0.0225 (8)0.0164 (7)−0.0051 (6)−0.0060 (6)−0.0038 (6)
C20.0176 (8)0.0186 (8)0.0190 (7)−0.0046 (6)−0.0072 (6)−0.0041 (6)
C30.0174 (8)0.0245 (8)0.0166 (7)−0.0082 (6)−0.0064 (6)−0.0022 (6)
C40.0150 (8)0.0261 (9)0.0166 (7)−0.0051 (6)−0.0034 (6)−0.0049 (6)
C50.0195 (8)0.0196 (8)0.0187 (7)−0.0031 (6)−0.0068 (6)−0.0054 (6)
C60.0164 (7)0.0202 (8)0.0167 (7)−0.0069 (6)−0.0071 (6)−0.0014 (6)
C70.0158 (8)0.0219 (8)0.0173 (7)−0.0043 (6)−0.0069 (6)−0.0048 (6)
C80.0163 (8)0.0178 (8)0.0176 (7)−0.0036 (6)−0.0058 (6)−0.0006 (6)
C90.0192 (8)0.0219 (8)0.0188 (7)−0.0061 (6)−0.0057 (6)−0.0037 (6)
C100.0211 (8)0.0261 (9)0.0241 (8)−0.0110 (7)−0.0069 (7)−0.0017 (7)
C110.0198 (8)0.0309 (9)0.0204 (8)−0.0097 (7)−0.0006 (6)−0.0031 (7)
C120.0266 (9)0.0277 (9)0.0193 (8)−0.0085 (7)−0.0025 (7)−0.0068 (7)
C130.0218 (8)0.0222 (8)0.0201 (8)−0.0090 (7)−0.0055 (6)−0.0032 (6)
C140.0192 (8)0.0255 (8)0.0172 (7)−0.0084 (7)−0.0059 (6)−0.0046 (6)
C150.0285 (9)0.0292 (9)0.0224 (8)−0.0171 (8)−0.0031 (7)−0.0014 (7)
C160.0375 (11)0.0290 (10)0.0270 (9)−0.0158 (8)−0.0071 (8)−0.0012 (7)
C170.0182 (8)0.0158 (8)0.0193 (7)−0.0046 (6)−0.0065 (6)−0.0024 (6)
C180.0190 (8)0.0191 (8)0.0190 (7)−0.0051 (6)−0.0069 (6)−0.0034 (6)
C190.0191 (8)0.0222 (8)0.0226 (8)−0.0050 (7)−0.0051 (6)−0.0071 (6)
C200.0213 (9)0.0289 (10)0.0341 (10)−0.0085 (7)−0.0057 (7)−0.0072 (8)
C210.0253 (12)0.0266 (13)0.0305 (14)−0.0117 (9)−0.0087 (10)−0.0007 (10)
C21X0.043 (8)0.059 (9)0.039 (8)−0.036 (7)−0.001 (6)0.005 (7)
C220.0406 (12)0.0322 (10)0.0328 (10)−0.0193 (9)−0.0144 (9)0.0034 (8)
C230.0303 (10)0.0175 (8)0.0326 (9)−0.0069 (7)−0.0136 (8)−0.0044 (7)

Geometric parameters (Å, °)

O1—C141.344 (2)C13—H13A0.9500
O1—C151.455 (2)C15—C161.497 (3)
O2—C141.213 (2)C15—H15A0.9900
O3—C231.229 (2)C15—H15B0.9900
N1—C71.322 (2)C16—H16A0.9800
N1—C11.388 (2)C16—H16B0.9800
N2—C71.377 (2)C16—H16C0.9800
N2—C61.384 (2)C17—C181.529 (2)
N2—C171.466 (2)C17—H17A0.9900
N3—C231.351 (2)C17—H17B0.9900
N3—C191.453 (2)C18—C191.525 (2)
N3—C201.466 (2)C18—H18A0.9900
C1—C21.396 (2)C18—H18B0.9900
C1—C61.405 (2)C19—H19A0.9900
C2—C31.392 (2)C19—H19B0.9900
C2—H2A0.9500C20—C211.507 (3)
C3—C41.411 (2)C20—C21X1.663 (16)
C3—C141.486 (2)C20—H20A0.9900
C4—C51.380 (2)C20—H20B0.9900
C4—H4A0.9500C20—H20C0.9600
C5—C61.392 (2)C20—H20D0.9600
C5—H5A0.9500C21—C221.566 (4)
C7—C81.476 (2)C21—H21A0.9900
C8—C131.391 (2)C21—H21B0.9900
C8—C91.396 (2)C21X—C221.318 (15)
C9—C101.394 (2)C21X—H21C0.9900
C9—H9A0.9500C21X—H21D0.9900
C10—C111.385 (2)C22—C231.514 (3)
C10—H10A0.9500C22—H22A0.9900
C11—C121.390 (3)C22—H22B0.9900
C11—H11A0.9500C22—H22C0.9601
C12—C131.386 (2)C22—H22D0.9599
C12—H12A0.9500
C14—O1—C15115.89 (13)C18—C17—H17B109.3
C7—N1—C1104.67 (13)H17A—C17—H17B108.0
C7—N2—C6106.22 (13)C19—C18—C17112.60 (13)
C7—N2—C17130.10 (13)C19—C18—H18A109.1
C6—N2—C17123.66 (13)C17—C18—H18A109.1
C23—N3—C19123.22 (15)C19—C18—H18B109.1
C23—N3—C20113.37 (15)C17—C18—H18B109.1
C19—N3—C20123.40 (14)H18A—C18—H18B107.8
N1—C1—C2129.67 (15)N3—C19—C18113.27 (13)
N1—C1—C6110.17 (14)N3—C19—H19A108.9
C2—C1—C6120.16 (14)C18—C19—H19A108.9
C3—C2—C1117.58 (15)N3—C19—H19B108.9
C3—C2—H2A121.2C18—C19—H19B108.9
C1—C2—H2A121.2H19A—C19—H19B107.7
C2—C3—C4120.96 (14)N3—C20—C21104.03 (16)
C2—C3—C14121.55 (15)N3—C20—C21X98.5 (5)
C4—C3—C14117.49 (14)N3—C20—H20A110.9
C5—C4—C3122.24 (15)C21—C20—H20A110.9
C5—C4—H4A118.9C21X—C20—H20A137.8
C3—C4—H4A118.9N3—C20—H20B110.9
C4—C5—C6116.13 (15)C21—C20—H20B110.9
C4—C5—H5A121.9C21X—C20—H20B86.5
C6—C5—H5A121.9H20A—C20—H20B109.0
N2—C6—C5131.52 (15)N3—C20—H20C110.6
N2—C6—C1105.56 (13)C21—C20—H20C91.1
C5—C6—C1122.89 (14)C21X—C20—H20C119.9
N1—C7—N2113.37 (14)H20B—C20—H20C125.6
N1—C7—C8121.39 (14)N3—C20—H20D110.5
N2—C7—C8125.23 (14)C21—C20—H20D129.9
C13—C8—C9119.02 (15)C21X—C20—H20D108.2
C13—C8—C7117.69 (14)H20A—C20—H20D89.5
C9—C8—C7123.04 (14)H20C—C20—H20D108.7
C10—C9—C8120.16 (15)C20—C21—C22102.78 (19)
C10—C9—H9A119.9C20—C21—H21A111.2
C8—C9—H9A119.9C22—C21—H21A111.2
C11—C10—C9120.22 (16)C20—C21—H21B111.2
C11—C10—H10A119.9C22—C21—H21B111.2
C9—C10—H10A119.9H21A—C21—H21B109.1
C10—C11—C12119.86 (15)C22—C21X—C20106.7 (10)
C10—C11—H11A120.1C22—C21X—H21C110.4
C12—C11—H11A120.1C20—C21X—H21C110.4
C13—C12—C11119.93 (16)C22—C21X—H21D110.4
C13—C12—H12A120.0C20—C21X—H21D110.4
C11—C12—H12A120.0H21C—C21X—H21D108.6
C12—C13—C8120.81 (15)C21X—C22—C23108.3 (5)
C12—C13—H13A119.6C23—C22—C21103.66 (16)
C8—C13—H13A119.6C21X—C22—H22A80.3
O2—C14—O1123.01 (15)C23—C22—H22A111.0
O2—C14—C3124.58 (16)C21—C22—H22A111.0
O1—C14—C3112.41 (14)C21X—C22—H22B132.2
O1—C15—C16107.21 (14)C23—C22—H22B111.0
O1—C15—H15A110.3C21—C22—H22B111.0
C16—C15—H15A110.3H22A—C22—H22B109.0
O1—C15—H15B110.3C21X—C22—H22C118.6
C16—C15—H15B110.3C23—C22—H22C109.4
H15A—C15—H15B108.5C21—C22—H22C92.5
C15—C16—H16A109.5H22A—C22—H22C125.7
C15—C16—H16B109.5C21X—C22—H22D102.6
H16A—C16—H16B109.5C23—C22—H22D109.4
C15—C16—H16C109.5C21—C22—H22D131.5
H16A—C16—H16C109.5H22B—C22—H22D89.0
H16B—C16—H16C109.5H22C—C22—H22D108.1
N2—C17—C18111.47 (13)O3—C23—N3125.09 (17)
N2—C17—H17A109.3O3—C23—C22126.97 (17)
C18—C17—H17A109.3N3—C23—C22107.94 (15)
N2—C17—H17B109.3
C7—N1—C1—C2179.81 (16)C9—C8—C13—C120.0 (2)
C7—N1—C1—C6−0.59 (17)C7—C8—C13—C12174.46 (15)
N1—C1—C2—C3177.87 (15)C15—O1—C14—O22.4 (2)
C6—C1—C2—C3−1.7 (2)C15—O1—C14—C3−176.97 (13)
C1—C2—C3—C40.0 (2)C2—C3—C14—O2167.58 (15)
C1—C2—C3—C14−179.74 (14)C4—C3—C14—O2−12.1 (2)
C2—C3—C4—C51.5 (2)C2—C3—C14—O1−13.1 (2)
C14—C3—C4—C5−178.76 (14)C4—C3—C14—O1167.23 (13)
C3—C4—C5—C6−1.1 (2)C14—O1—C15—C16176.49 (14)
C7—N2—C6—C5177.41 (16)C7—N2—C17—C18103.28 (18)
C17—N2—C6—C5−1.0 (3)C6—N2—C17—C18−78.68 (18)
C7—N2—C6—C1−0.75 (16)N2—C17—C18—C19173.40 (12)
C17—N2—C6—C1−179.19 (13)C23—N3—C19—C18−119.11 (17)
C4—C5—C6—N2−178.55 (15)C20—N3—C19—C1860.0 (2)
C4—C5—C6—C1−0.7 (2)C17—C18—C19—N361.78 (18)
N1—C1—C6—N20.85 (17)C23—N3—C20—C21−19.5 (2)
C2—C1—C6—N2−179.51 (13)C19—N3—C20—C21161.3 (2)
N1—C1—C6—C5−177.51 (14)C23—N3—C20—C21X10.4 (9)
C2—C1—C6—C52.1 (2)C19—N3—C20—C21X−168.8 (9)
C1—N1—C7—N20.10 (17)N3—C20—C21—C2227.4 (3)
C1—N1—C7—C8179.80 (13)C21X—C20—C21—C22−55.1 (10)
C6—N2—C7—N10.42 (18)N3—C20—C21X—C22−20.9 (15)
C17—N2—C7—N1178.73 (14)C21—C20—C21X—C2282.6 (17)
C6—N2—C7—C8−179.26 (14)C20—C21X—C22—C2323.0 (16)
C17—N2—C7—C8−1.0 (3)C20—C21X—C22—C21−63.6 (13)
N1—C7—C8—C13−38.6 (2)C20—C21—C22—C21X76.2 (10)
N2—C7—C8—C13141.03 (16)C20—C21—C22—C23−26.5 (3)
N1—C7—C8—C9135.58 (16)C19—N3—C23—O31.5 (3)
N2—C7—C8—C9−44.8 (2)C20—N3—C23—O3−177.71 (17)
C13—C8—C9—C10−0.6 (2)C19—N3—C23—C22−178.94 (15)
C7—C8—C9—C10−174.69 (15)C20—N3—C23—C221.9 (2)
C8—C9—C10—C110.5 (3)C21X—C22—C23—O3162.4 (12)
C9—C10—C11—C120.1 (3)C21—C22—C23—O3−164.6 (2)
C10—C11—C12—C13−0.6 (3)C21X—C22—C23—N3−17.2 (12)
C11—C12—C13—C80.6 (3)C21—C22—C23—N315.8 (2)

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
C5—H5A···O3i0.952.323.266 (2)172
C16—H16B···O3ii0.982.563.341 (3)137
C19—H19B···O3i0.992.573.391 (3)141
C10—H10A···Cgiii0.952.903.516 (2)124

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5398).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.
  • Bruker (2009). APEX2, SAINT and SADABSBruker AXS Inc., Madison, Wisconsin, USA.
  • Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.
  • Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.
  • Garuti, L., Roberti, M., Malagoli, M., Rossi, T. & Castelli, M. (2000). Bioorg. Med. Chem. Lett. 10, 2193–2195. [PubMed]
  • Ozden, S., Atabey, D., Yildiz, S. & Goker, H. (2008). Eur. J. Med. Chem. 43, 1390–1402. [PubMed]
  • Rao, A., Chimirri, A., Clercq, E. D., Monforte, A. M., Monforte, P., Pannecouque, C. & Zappala, M. (2002). Farmaco, 57, 819–823. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Thakurdesai, P. A., Wadodkar, S. G. & Chopade, C. T. (2007). Pharmacol. Online, 1, 314–329.

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