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

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ISSN: 2056-9890

1-{[(Cyclo­hexyl­­oxy)carbon­yl]­­oxy}ethyl 3-{[2′-(2-ethyl-2H-tetra­zol-5-yl)bi­phenyl-4-yl]meth­yl}-2-oxo-2,3-di­hydro-1H-benzimidazole-4-carboxyl­ate

aDepartment of Chemistry, National College, Tiruchirappali 620 001, India, and bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 26 February 2010; accepted 24 March 2010; online 31 March 2010)

In the title compound, C33H34N6O6, the dihydro­benzimidazol-2-one ring system is essentially planar (r.m.s. deviation = 0.021 Å). The cyclo­hexane ring adopts a chair conformation. In the 5-(biphenyl-2-yl)-2H-tetra­zole fragment, the tetra­zole ring is twisted away from the attached benzene ring by 35.73 (11)° and the two benzene rings form a dihedral angle of 68.00 (9)°. An intra­molecular C—H⋯O inter­action is observed. In the crystal, the mol­ecules are linked into a zigzag chain running along the b axis by inter­molecular N—H⋯O hydrogen bonds.

Related literature

For applications of tetra­zole derivatives in coordination chemistry, medicinal chemistry and materials science, see: Dunica et al. (1991[Dunica, J. V., Pierce, M. E. & Santella, J. B. III (1991). J. Org. Chem. 56, 2395-2400.]); Wittenberger & Donner (1993[Wittenberger, S. J. & Donner, B. G. (1993). J. Org. Chem. 58, 4139-4141.]); Xiong et al. (2002[Xiong, R. G., Xue, X., Zhao, H., You, X. Z., Abrahams, B. F. & Xue, Z. L. (2002). Angew. Chem. Int. Ed. 41, 3800-3803.]); Xue et al. (2002[Xue, X., Wang, X. S., Wang, L. Z., Xiong, R. G., Abrahams, B. F., You, X. Z., Xue, Z. L. & Che, C.-M. (2002). Inorg. Chem. 41, 3800-3803.]). For metal-organic coordination compounds with tetra­zole ligands, see: Hu et al. (2007[Hu, B., Xu, X.-B., Li, Y.-X. & Ye, H.-Y. (2007). Acta Cryst. E63, m2698.]); Lü (2008[Lü, Y. (2008). Acta Cryst. E64, m1255.]). 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
  • C33H34N6O6

  • Mr = 610.66

  • Monoclinic, C 2/c

  • a = 16.3770 (7) Å

  • b = 8.5928 (4) Å

  • c = 43.7733 (19) Å

  • β = 91.150 (1)°

  • V = 6158.7 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.19 × 0.14 × 0.08 mm

Data collection
  • Bruker Kappa APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2001[Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany.]) Tmin = 0.984, Tmax = 0.993

  • 34307 measured reflections

  • 7255 independent reflections

  • 5559 reflections with I > 2σ(I)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.143

  • S = 0.99

  • 7255 reflections

  • 412 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N16—H16⋯O6i 0.85 (2) 2.04 (2) 2.8508 (19) 161 (2)
C20—H20A⋯O5 0.97 2.22 3.004 (2) 137
Symmetry code: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Tetrazole derivatives have attracted considerable attention due to their biological activities. The synthesis of new ligands in this family is an important task for the development of modern coordination chemistry (Hu et al., 2007; Lü, 2008). These compounds also possess wide range of applications in coordination chemistry, medicinal chemistry and materials science (Xiong et al., 2002; Xue et al., 2002; Dunica et al., 1991; Wittenberger et al., 1993). In view of these importance and to ascertain the molecular conformation, an X-ray crystallographic study of the title compound has been carried out.

In the title molecule (Fig.1), the dihydrobenzimidazol-2-one ring system and tetrazole ring are planar. The cyclohexane ring adopts a chair conformation; the puckering parameters (Cremer & Pople, 1975) are: q2 = 0.006 (3) Å, q3 = -0.564 (3) Å and ϕ2 = 106.1 (1)°. The sum of the bond angles around atoms N16 (358.7°) and N18 (358.0°) of the benzimidazole ring system are in accordance with sp2 hybridization. In the 5-(2-biphenyl)-2H-tetrazole fragment, the tetrazole ring is twisted away from the attached benzene ring by 35.73 (11)°, and the two benzene rings form a dihedral angle of 68.00 (9)°. An intramolecular C—H···O interaction is observed.

Atom N16 of the molecule at (x, y, z) donates a proton to atom O6 of the molecule at (1/2-x, 1/2+y, 1/2-z ) forming an intermolecular N—H···O bond which link the molecules into a zigzag chain running along b axis as shown in Fig 2.

Related literature top

For applications of tetrazole derivatives in coordination chemistry, medicinal chemistry and materials science, see: Dunica et al. (1991); Wittenberger & Donner (1993); Xiong et al. (2002); Xue et al. (2002). For metal-organic coordination compounds with tetrazole ligands, see: Hu et al. (2007); Lü (2008). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

To a suspension of 1-{[(cyclohexyloxy)carbonyl]oxy}ethyl-2-oxo-1-{[2'-(1H- tetrazol-5-yl) biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylate (40.0 g) in N, N-dimethyl formamide (250 ml), potassium carbonate (19 g) and ethyl iodide (16.0 g) were added. The mixture was heated and stirred for 2.5 h at 343–355 K. Then the solid was filtered and washed with cold water. The above solid material (20.0 g) was separated and purified by conventional column chromatography using hexane-ethyl acetate (2:1) as eluent. Single crystals were obtained by recrystallizing the crude product from ethanol by slow evaporation technique.

Refinement top

The N-bound H atom was located in a difference map and refined freely. C-bound H atoms were positioned geometrically (C-H = 0.93-0.98 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.5Ueq(C) for methyl H and 1.2 Ueq(C) for other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids at the 30% probability level. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed down the c axis. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.
1-{[(Cyclohexyloxy)carbonyl]oxy}ethyl 3-{[2'-(2-ethyl-2H-tetrazol-5-yl)biphenyl-4-yl]methyl}- 2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate top
Crystal data top
C33H34N6O6F(000) = 2576
Mr = 610.66Dx = 1.317 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3564 reflections
a = 16.3770 (7) Åθ = 0.9–25.0°
b = 8.5928 (4) ŵ = 0.09 mm1
c = 43.7733 (19) ÅT = 293 K
β = 91.150 (1)°Plate, colourless
V = 6158.7 (5) Å30.19 × 0.14 × 0.08 mm
Z = 8
Data collection top
Bruker Kappa APEXII area-detector
diffractometer
7255 independent reflections
Radiation source: fine-focus sealed tube5559 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ω scansθmax = 28.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 2120
Tmin = 0.984, Tmax = 0.993k = 1111
34307 measured reflectionsl = 5657
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0675P)2 + 3.4615P]
where P = (Fo2 + 2Fc2)/3
7255 reflections(Δ/σ)max = 0.017
412 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C33H34N6O6V = 6158.7 (5) Å3
Mr = 610.66Z = 8
Monoclinic, C2/cMo Kα radiation
a = 16.3770 (7) ŵ = 0.09 mm1
b = 8.5928 (4) ÅT = 293 K
c = 43.7733 (19) Å0.19 × 0.14 × 0.08 mm
β = 91.150 (1)°
Data collection top
Bruker Kappa APEXII area-detector
diffractometer
7255 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
5559 reflections with I > 2σ(I)
Tmin = 0.984, Tmax = 0.993Rint = 0.026
34307 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.29 e Å3
7255 reflectionsΔρmin = 0.17 e Å3
412 parameters
Special details top

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 > 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*/Ueq
O10.10538 (9)0.40762 (15)0.08077 (3)0.0628 (3)
O20.08267 (10)0.24202 (17)0.11988 (3)0.0791 (4)
O30.14741 (9)0.47031 (16)0.12506 (3)0.0666 (4)
O40.09830 (8)0.58427 (14)0.16718 (3)0.0574 (3)
O50.05644 (7)0.45285 (14)0.20880 (3)0.0568 (3)
O60.24689 (8)0.63668 (14)0.25144 (3)0.0567 (3)
C10.01658 (15)0.3068 (4)0.05704 (6)0.1087 (10)
H1A0.04030.27600.07660.130*
H1B0.03290.41320.05300.130*
C20.04851 (15)0.2007 (5)0.03206 (7)0.1128 (11)
H2A0.10730.21250.03080.135*
H2B0.03710.09320.03720.135*
C30.00998 (16)0.2383 (3)0.00197 (6)0.0852 (7)
H3A0.02860.16480.01320.102*
H3B0.02660.34170.00430.102*
C40.08144 (16)0.2316 (3)0.00346 (5)0.0871 (7)
H4A0.09820.12550.00750.105*
H4B0.10500.26230.01610.105*
C50.11349 (14)0.3378 (3)0.02823 (5)0.0725 (6)
H5A0.10200.44530.02310.087*
H5B0.17220.32580.02960.087*
C60.07367 (11)0.2981 (2)0.05837 (4)0.0570 (4)
H60.08950.19230.06410.068*
C70.10780 (11)0.3606 (2)0.10939 (4)0.0528 (4)
C80.14875 (11)0.4568 (2)0.15726 (4)0.0564 (4)
H80.12610.35690.16410.068*
C90.23394 (14)0.4783 (3)0.16790 (5)0.0839 (7)
H9A0.25530.57490.16010.126*
H9B0.23400.48000.18980.126*
H9C0.26740.39390.16060.126*
C100.05646 (9)0.56936 (19)0.19372 (3)0.0443 (3)
C110.01429 (9)0.71732 (18)0.20158 (3)0.0444 (3)
C120.05366 (11)0.8580 (2)0.19443 (4)0.0552 (4)
H120.10340.85460.18380.066*
C130.02180 (12)1.0009 (2)0.20246 (5)0.0621 (5)
H130.05051.09110.19750.074*
C140.05270 (12)1.0113 (2)0.21790 (4)0.0572 (4)
H140.07481.10720.22340.069*
C150.09259 (10)0.87500 (18)0.22476 (4)0.0452 (4)
N160.16694 (9)0.85162 (16)0.23946 (3)0.0479 (3)
H160.1995 (13)0.923 (2)0.2449 (5)0.064 (6)*
C170.18479 (10)0.69756 (18)0.24083 (3)0.0444 (3)
N180.11883 (8)0.62020 (14)0.22739 (3)0.0408 (3)
C190.06123 (9)0.72809 (17)0.21703 (3)0.0401 (3)
C200.12542 (10)0.45543 (17)0.21919 (3)0.0429 (3)
H20A0.07290.40530.22170.052*
H20B0.16460.40510.23280.052*
C210.15208 (9)0.43559 (17)0.18655 (4)0.0424 (3)
C220.22015 (11)0.5131 (2)0.17578 (4)0.0556 (4)
H220.25080.57560.18900.067*
C230.24300 (11)0.4989 (2)0.14583 (4)0.0569 (4)
H230.28840.55320.13910.068*
C240.19952 (10)0.40521 (19)0.12553 (4)0.0484 (4)
C250.13343 (12)0.3242 (2)0.13648 (4)0.0572 (4)
H250.10460.25740.12350.069*
C260.10931 (11)0.3405 (2)0.16638 (4)0.0538 (4)
H260.06370.28680.17300.065*
C270.22306 (10)0.3941 (2)0.09282 (4)0.0502 (4)
C280.25473 (13)0.2562 (2)0.08167 (5)0.0660 (5)
H280.25800.16950.09440.079*
C290.28138 (14)0.2456 (3)0.05206 (5)0.0750 (6)
H290.30260.15220.04500.090*
C300.27686 (13)0.3714 (3)0.03306 (5)0.0713 (6)
H300.29630.36450.01330.086*
C310.24339 (12)0.5087 (2)0.04329 (4)0.0619 (5)
H310.23910.59360.03020.074*
C320.21603 (10)0.5215 (2)0.07304 (4)0.0503 (4)
C330.17652 (10)0.6676 (2)0.08233 (4)0.0518 (4)
N340.19874 (13)0.8085 (2)0.07278 (5)0.0880 (6)
N350.14788 (13)0.9081 (2)0.08502 (6)0.0919 (6)
N360.09842 (10)0.82671 (19)0.10133 (4)0.0671 (4)
N370.11305 (11)0.67617 (19)0.10042 (4)0.0722 (5)
C380.03020 (16)0.8941 (3)0.11829 (7)0.0923 (8)
H38A0.03230.85660.13920.111*
H38B0.03561.00650.11870.111*
C390.04796 (16)0.8525 (3)0.10426 (9)0.1114 (10)
H39A0.05010.88940.08360.167*
H39B0.09120.89920.11550.167*
H39C0.05410.74140.10440.167*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0817 (9)0.0544 (7)0.0523 (7)0.0067 (6)0.0012 (6)0.0039 (6)
O20.1041 (11)0.0636 (9)0.0700 (9)0.0226 (8)0.0118 (8)0.0078 (7)
O30.0888 (9)0.0646 (8)0.0459 (7)0.0217 (7)0.0104 (6)0.0073 (6)
O40.0671 (8)0.0548 (7)0.0496 (7)0.0036 (6)0.0145 (6)0.0028 (5)
O50.0632 (7)0.0562 (7)0.0505 (7)0.0091 (6)0.0077 (5)0.0100 (6)
O60.0564 (7)0.0507 (7)0.0624 (7)0.0044 (5)0.0168 (6)0.0005 (5)
C10.0600 (13)0.180 (3)0.0852 (17)0.0025 (16)0.0065 (12)0.0433 (19)
C20.0604 (14)0.180 (3)0.099 (2)0.0255 (17)0.0073 (13)0.036 (2)
C30.0959 (17)0.0853 (16)0.0755 (14)0.0040 (13)0.0323 (13)0.0007 (12)
C40.0925 (17)0.1098 (19)0.0588 (12)0.0266 (14)0.0034 (11)0.0175 (12)
C50.0751 (13)0.0808 (14)0.0617 (12)0.0164 (11)0.0018 (10)0.0073 (10)
C60.0629 (11)0.0526 (10)0.0558 (10)0.0027 (8)0.0068 (8)0.0049 (8)
C70.0524 (9)0.0496 (9)0.0561 (10)0.0003 (8)0.0036 (8)0.0041 (8)
C80.0665 (11)0.0564 (10)0.0459 (9)0.0010 (8)0.0097 (8)0.0012 (8)
C90.0662 (13)0.1121 (19)0.0734 (14)0.0081 (13)0.0012 (11)0.0025 (13)
C100.0421 (8)0.0518 (9)0.0390 (8)0.0031 (7)0.0011 (6)0.0004 (7)
C110.0456 (8)0.0462 (8)0.0414 (8)0.0030 (7)0.0014 (6)0.0023 (6)
C120.0525 (9)0.0562 (10)0.0565 (10)0.0106 (8)0.0068 (8)0.0040 (8)
C130.0672 (11)0.0462 (9)0.0726 (12)0.0147 (8)0.0048 (9)0.0080 (9)
C140.0693 (11)0.0377 (8)0.0644 (11)0.0019 (8)0.0012 (9)0.0035 (7)
C150.0501 (9)0.0419 (8)0.0438 (8)0.0007 (7)0.0024 (7)0.0034 (6)
N160.0503 (8)0.0408 (7)0.0525 (8)0.0040 (6)0.0022 (6)0.0014 (6)
C170.0500 (9)0.0433 (8)0.0399 (8)0.0002 (7)0.0016 (6)0.0012 (6)
N180.0466 (7)0.0368 (6)0.0390 (6)0.0014 (5)0.0020 (5)0.0026 (5)
C190.0457 (8)0.0378 (7)0.0368 (7)0.0024 (6)0.0033 (6)0.0038 (6)
C200.0504 (8)0.0340 (7)0.0442 (8)0.0024 (6)0.0052 (6)0.0053 (6)
C210.0459 (8)0.0346 (7)0.0465 (8)0.0050 (6)0.0045 (6)0.0020 (6)
C220.0500 (9)0.0607 (10)0.0560 (10)0.0081 (8)0.0003 (7)0.0154 (8)
C230.0474 (9)0.0639 (11)0.0599 (10)0.0083 (8)0.0076 (8)0.0100 (9)
C240.0525 (9)0.0432 (8)0.0494 (9)0.0071 (7)0.0006 (7)0.0021 (7)
C250.0700 (11)0.0511 (10)0.0503 (9)0.0139 (8)0.0077 (8)0.0038 (8)
C260.0619 (10)0.0481 (9)0.0513 (9)0.0131 (8)0.0023 (8)0.0039 (7)
C270.0464 (8)0.0534 (9)0.0505 (9)0.0043 (7)0.0017 (7)0.0078 (7)
C280.0738 (13)0.0592 (11)0.0649 (12)0.0169 (10)0.0017 (10)0.0096 (9)
C290.0766 (13)0.0744 (14)0.0741 (14)0.0201 (11)0.0048 (11)0.0262 (11)
C300.0681 (12)0.0905 (16)0.0557 (11)0.0045 (11)0.0111 (9)0.0228 (11)
C310.0618 (11)0.0720 (12)0.0522 (10)0.0010 (9)0.0062 (8)0.0037 (9)
C320.0446 (8)0.0547 (10)0.0515 (9)0.0012 (7)0.0023 (7)0.0065 (7)
C330.0516 (9)0.0529 (9)0.0508 (9)0.0010 (8)0.0027 (7)0.0009 (7)
N340.0871 (13)0.0578 (10)0.1206 (17)0.0016 (10)0.0389 (12)0.0022 (11)
N350.0909 (14)0.0528 (10)0.1329 (19)0.0002 (10)0.0299 (13)0.0023 (11)
N360.0632 (9)0.0525 (9)0.0861 (12)0.0072 (8)0.0118 (8)0.0043 (8)
N370.0714 (10)0.0525 (9)0.0935 (13)0.0126 (8)0.0265 (9)0.0053 (8)
C380.0877 (17)0.0716 (14)0.118 (2)0.0227 (13)0.0237 (15)0.0142 (14)
C390.0715 (16)0.0864 (18)0.177 (3)0.0111 (14)0.0266 (18)0.0051 (19)
Geometric parameters (Å, º) top
O1—C71.318 (2)N16—C171.357 (2)
O1—C61.462 (2)N16—H160.85 (2)
O2—C71.188 (2)C17—N181.389 (2)
O3—C71.341 (2)N18—C191.3919 (19)
O3—C81.415 (2)N18—C201.4652 (19)
O4—C101.3432 (18)C20—C211.512 (2)
O4—C81.434 (2)C20—H20A0.97
O5—C101.1992 (19)C20—H20B0.97
O6—C171.2265 (19)C21—C261.383 (2)
C1—C61.482 (3)C21—C221.389 (2)
C1—C21.524 (4)C22—C231.376 (2)
C1—H1A0.97C22—H220.93
C1—H1B0.97C23—C241.385 (2)
C2—C31.485 (4)C23—H230.93
C2—H2A0.97C24—C251.381 (2)
C2—H2B0.97C24—C271.494 (2)
C3—C41.501 (4)C25—C261.382 (3)
C3—H3A0.97C25—H250.93
C3—H3B0.97C26—H260.93
C4—C51.519 (3)C27—C281.386 (2)
C4—H4A0.97C27—C321.399 (2)
C4—H4B0.97C28—C291.379 (3)
C5—C61.499 (3)C28—H280.93
C5—H5A0.97C29—C301.365 (3)
C5—H5B0.97C29—H290.93
C6—H60.98C30—C311.380 (3)
C8—C91.491 (3)C30—H300.93
C8—H80.98C31—C321.390 (2)
C9—H9A0.96C31—H310.93
C9—H9B0.96C32—C331.473 (2)
C9—H9C0.96C33—N371.321 (2)
C10—C111.484 (2)C33—N341.334 (2)
C11—C191.401 (2)N34—N351.316 (3)
C11—C121.402 (2)N35—N361.296 (3)
C12—C131.377 (3)N36—N371.316 (2)
C12—H120.93N36—C381.472 (3)
C13—C141.386 (3)C38—C391.453 (4)
C13—H130.93C38—H38A0.97
C14—C151.372 (2)C38—H38B0.97
C14—H140.93C39—H39A0.96
C15—N161.381 (2)C39—H39B0.96
C15—C191.402 (2)C39—H39C0.96
C7—O1—C6117.26 (14)C15—N16—H16124.8 (14)
C7—O3—C8117.98 (14)O6—C17—N16127.52 (15)
C10—O4—C8118.04 (13)O6—C17—N18126.02 (14)
C6—C1—C2110.8 (2)N16—C17—N18106.46 (13)
C6—C1—H1A109.5C17—N18—C19109.60 (12)
C2—C1—H1A109.5C17—N18—C20120.38 (13)
C6—C1—H1B109.5C19—N18—C20128.06 (12)
C2—C1—H1B109.5N18—C19—C11134.37 (14)
H1A—C1—H1B108.1N18—C19—C15106.18 (13)
C3—C2—C1111.2 (3)C11—C19—C15119.45 (14)
C3—C2—H2A109.4N18—C20—C21111.38 (12)
C1—C2—H2A109.4N18—C20—H20A109.4
C3—C2—H2B109.4C21—C20—H20A109.4
C1—C2—H2B109.4N18—C20—H20B109.4
H2A—C2—H2B108.0C21—C20—H20B109.4
C2—C3—C4111.1 (2)H20A—C20—H20B108.0
C2—C3—H3A109.4C26—C21—C22117.78 (15)
C4—C3—H3A109.4C26—C21—C20121.18 (14)
C2—C3—H3B109.4C22—C21—C20121.04 (14)
C4—C3—H3B109.4C23—C22—C21121.10 (16)
H3A—C3—H3B108.0C23—C22—H22119.4
C3—C4—C5111.6 (2)C21—C22—H22119.4
C3—C4—H4A109.3C22—C23—C24121.07 (16)
C5—C4—H4A109.3C22—C23—H23119.5
C3—C4—H4B109.3C24—C23—H23119.5
C5—C4—H4B109.3C25—C24—C23117.84 (16)
H4A—C4—H4B108.0C25—C24—C27121.32 (15)
C6—C5—C4109.95 (18)C23—C24—C27120.84 (16)
C6—C5—H5A109.7C24—C25—C26121.24 (16)
C4—C5—H5A109.7C24—C25—H25119.4
C6—C5—H5B109.7C26—C25—H25119.4
C4—C5—H5B109.7C21—C26—C25120.92 (16)
H5A—C5—H5B108.2C21—C26—H26119.5
O1—C6—C1111.23 (17)C25—C26—H26119.5
O1—C6—C5106.85 (15)C28—C27—C32118.54 (17)
C1—C6—C5111.75 (19)C28—C27—C24119.85 (16)
O1—C6—H6109.0C32—C27—C24121.59 (15)
C1—C6—H6109.0C29—C28—C27121.0 (2)
C5—C6—H6109.0C29—C28—H28119.5
O2—C7—O1127.88 (17)C27—C28—H28119.5
O2—C7—O3124.95 (17)C30—C29—C28120.42 (19)
O1—C7—O3107.13 (15)C30—C29—H29119.8
O3—C8—O4102.64 (14)C28—C29—H29119.8
O3—C8—C9109.53 (16)C29—C30—C31119.77 (19)
O4—C8—C9110.35 (17)C29—C30—H30120.1
O3—C8—H8111.3C31—C30—H30120.1
O4—C8—H8111.3C30—C31—C32120.61 (19)
C9—C8—H8111.3C30—C31—H31119.7
C8—C9—H9A109.5C32—C31—H31119.7
C8—C9—H9B109.5C31—C32—C27119.62 (16)
H9A—C9—H9B109.5C31—C32—C33118.51 (17)
C8—C9—H9C109.5C27—C32—C33121.80 (15)
H9A—C9—H9C109.5N37—C33—N34111.09 (16)
H9B—C9—H9C109.5N37—C33—C32124.63 (16)
O5—C10—O4123.38 (15)N34—C33—C32124.25 (17)
O5—C10—C11126.35 (14)N35—N34—C33106.52 (18)
O4—C10—C11110.23 (13)N36—N35—N34106.30 (17)
C19—C11—C12116.65 (15)N35—N36—N37113.45 (16)
C19—C11—C10124.81 (14)N35—N36—C38123.69 (18)
C12—C11—C10118.48 (14)N37—N36—C38122.82 (18)
C13—C12—C11122.79 (16)N36—N37—C33102.65 (16)
C13—C12—H12118.6C39—C38—N36111.2 (2)
C11—C12—H12118.6C39—C38—H38A109.4
C12—C13—C14120.48 (16)N36—C38—H38A109.4
C12—C13—H13119.8C39—C38—H38B109.4
C14—C13—H13119.8N36—C38—H38B109.4
C15—C14—C13117.54 (16)H38A—C38—H38B108.0
C15—C14—H14121.2C38—C39—H39A109.5
C13—C14—H14121.2C38—C39—H39B109.5
C14—C15—N16129.65 (15)H39A—C39—H39B109.5
C14—C15—C19123.08 (15)C38—C39—H39C109.5
N16—C15—C19107.27 (13)H39A—C39—H39C109.5
C17—N16—C15110.47 (14)H39B—C39—H39C109.5
C17—N16—H16124.4 (14)
C6—C1—C2—C355.9 (4)N16—C15—C19—N180.28 (17)
C1—C2—C3—C455.3 (4)C14—C15—C19—C110.0 (2)
C2—C3—C4—C555.8 (3)N16—C15—C19—C11179.68 (14)
C3—C4—C5—C655.5 (3)C17—N18—C20—C2192.35 (16)
C7—O1—C6—C185.6 (2)C19—N18—C20—C2170.00 (19)
C7—O1—C6—C5152.22 (17)N18—C20—C21—C26128.84 (15)
C2—C1—C6—O1176.0 (2)N18—C20—C21—C2250.8 (2)
C2—C1—C6—C556.6 (3)C26—C21—C22—C231.7 (3)
C4—C5—C6—O1178.24 (19)C20—C21—C22—C23177.95 (16)
C4—C5—C6—C156.4 (3)C21—C22—C23—C240.9 (3)
C6—O1—C7—O25.0 (3)C22—C23—C24—C251.2 (3)
C6—O1—C7—O3172.79 (15)C22—C23—C24—C27178.11 (17)
C8—O3—C7—O210.3 (3)C23—C24—C25—C262.5 (3)
C8—O3—C7—O1171.84 (15)C27—C24—C25—C26176.77 (16)
C7—O3—C8—O4110.92 (17)C22—C21—C26—C250.3 (3)
C7—O3—C8—C9131.85 (19)C20—C21—C26—C25179.28 (15)
C10—O4—C8—O3150.40 (14)C24—C25—C26—C211.8 (3)
C10—O4—C8—C992.95 (19)C25—C24—C27—C2868.9 (2)
C8—O4—C10—O53.3 (2)C23—C24—C27—C28111.8 (2)
C8—O4—C10—C11174.68 (14)C25—C24—C27—C32112.8 (2)
O5—C10—C11—C1935.4 (3)C23—C24—C27—C3266.5 (2)
O4—C10—C11—C19146.73 (15)C32—C27—C28—C292.2 (3)
O5—C10—C11—C12141.61 (18)C24—C27—C28—C29176.16 (18)
O4—C10—C11—C1236.3 (2)C27—C28—C29—C300.2 (3)
C19—C11—C12—C131.3 (3)C28—C29—C30—C311.7 (3)
C10—C11—C12—C13175.95 (17)C29—C30—C31—C321.6 (3)
C11—C12—C13—C140.9 (3)C30—C31—C32—C270.4 (3)
C12—C13—C14—C150.1 (3)C30—C31—C32—C33176.57 (17)
C13—C14—C15—N16179.23 (17)C28—C27—C32—C312.3 (3)
C13—C14—C15—C190.4 (3)C24—C27—C32—C31176.01 (16)
C14—C15—N16—C17178.38 (18)C28—C27—C32—C33174.63 (16)
C19—C15—N16—C171.28 (18)C24—C27—C32—C337.1 (2)
C15—N16—C17—O6177.55 (16)C31—C32—C33—N37141.6 (2)
C15—N16—C17—N181.74 (17)C27—C32—C33—N3735.3 (3)
O6—C17—N18—C19177.75 (15)C31—C32—C33—N3436.2 (3)
N16—C17—N18—C191.55 (17)C27—C32—C33—N34146.8 (2)
O6—C17—N18—C2012.4 (2)N37—C33—N34—N350.3 (3)
N16—C17—N18—C20166.86 (13)C32—C33—N34—N35177.82 (19)
C17—N18—C19—C11178.49 (16)C33—N34—N35—N360.5 (3)
C20—N18—C19—C1114.6 (3)N34—N35—N36—N370.6 (3)
C17—N18—C19—C150.78 (16)N34—N35—N36—C38178.2 (2)
C20—N18—C19—C15164.66 (14)N35—N36—N37—C330.5 (3)
C12—C11—C19—N18178.42 (16)C38—N36—N37—C33178.1 (2)
C10—C11—C19—N184.6 (3)N34—C33—N37—N360.1 (2)
C12—C11—C19—C150.8 (2)C32—C33—N37—N36178.19 (17)
C10—C11—C19—C15176.23 (14)N35—N36—C38—C39109.2 (3)
C14—C15—C19—N18179.41 (16)N37—N36—C38—C3968.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N16—H16···O6i0.85 (2)2.04 (2)2.8508 (19)161 (2)
C20—H20A···O50.972.223.004 (2)137
Symmetry code: (i) x+1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC33H34N6O6
Mr610.66
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)16.3770 (7), 8.5928 (4), 43.7733 (19)
β (°) 91.150 (1)
V3)6158.7 (5)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.19 × 0.14 × 0.08
Data collection
DiffractometerBruker Kappa APEXII area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2001)
Tmin, Tmax0.984, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
34307, 7255, 5559
Rint0.026
(sin θ/λ)max1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.143, 0.99
No. of reflections7255
No. of parameters412
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.29, 0.17

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N16—H16···O6i0.85 (2)2.04 (2)2.8508 (19)161 (2)
C20—H20A···O50.972.223.004 (2)137
Symmetry code: (i) x+1/2, y+1/2, z+1/2.
 

Acknowledgements

The authors thank the Management and Principal of National College, Tiruchirappalli, Tamil Nadu, India, for their support.

References

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First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
First citationDunica, J. V., Pierce, M. E. & Santella, J. B. III (1991). J. Org. Chem. 56, 2395–2400.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
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First citationXiong, R. G., Xue, X., Zhao, H., You, X. Z., Abrahams, B. F. & Xue, Z. L. (2002). Angew. Chem. Int. Ed. 41, 3800–3803.  CrossRef CAS Google Scholar
First citationXue, X., Wang, X. S., Wang, L. Z., Xiong, R. G., Abrahams, B. F., You, X. Z., Xue, Z. L. & Che, C.-M. (2002). Inorg. Chem. 41, 3800–3803.  Web of Science CSD CrossRef Google Scholar

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