N,N'-Dibenzyl-2,2'-(3,6-dioxaoctane-1,8-diyldi-oxy)dibenzamide.

Abstract

The title compound, C(34)H(36)N(2)O(6), located on a center of inversion, crystallizes with one half-mol-ecule in the asymmetric unit. The dihedral angle between the benzene rings is 86.19 (2)°. An intra-molecular N-H⋯O hydrogen bond forms a six-membered ring; it affects the conformation of the mol-ecule which adopts a folded rather than open conformation. The crystal packing is stabilized by inter-molecular C-H⋯O inter-actions.

Full text

Page 1

N,N0 0 0-Dibenzyl-2,20 0 0-(3,6-dioxaoctane-
1,8-diyldioxy)dibenzamide
Yong-Hong Wen* and Ji-Min Dai
College of Chemistry and Molecular Engineering, Qingdao University of Science and
Technology, Qingdao 266042, People’s Republic of China
Correspondence e-mail: wenyyhh@126.com
Received 14 November 2010; accepted 14 January 2011
Key indicators: single-crystal X-ray study; T = 294 K; mean ?(C–C) = 0.005 A ˚;
R factor = 0.048; wR factor = 0.149; data-to-parameter ratio = 14.2.
The title compound, C34H36N2O6, located on a center of
inversion, crystallizes with one half-molecule in the asym-
metric unit. The dihedral angle between the benzene rings is
86.19 (2)?. An intramolecular N—H???O hydrogen bond
forms a six-membered ring; it affects the conformation of
the molecule which adopts a folded rather than open
conformation. The crystal packing is stabilized by inter-
molecular C—H???O interactions.
Related literature
For background to the applications of amide-type acyclic
polyethers, see: Wen et al. (2002, 2008); Lehn et al. (1995). For
related structures of amide-type acyclic polyethers, see: Wen et
al. (2005, 2008).
Experimental
Crystal data
C34H36N2O6
Mr= 568.65
Monoclinic, P21=c
a = 12.065 (3) A˚
b = 15.964 (4) A˚
c = 8.251 (2) A˚
? = 104.820 (5)?
V = 1536.3 (7) A˚3
Z = 2
Mo K? radiation
? = 0.08 mm?1
T = 294 K
0.24 ? 0.20 ? 0.16 mm
Data collection
Bruker SMART CCD area-detector
diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
Tmin= 0.976, Tmax= 0.983
7850 measured reflections
2707 independent reflections
1284 reflections with I > 2?(I)
Rint= 0.041
Refinement
R[F2> 2?(F2)] = 0.048
wR(F2) = 0.149
S = 1.00
2707 reflections
190 parameters
36 restraints
H-atom parameters constrained
??max= 0.21 e A˚?3
??min= ?0.17 e A˚?3
Table 1
Hydrogen-bond geometry (A˚,?).
D—H???A
N1—H1???O2
C15—H15B???O1i
Symmetry code: (i) ?x þ 2;?y þ 2;?z þ 1.
D—HH???AD???AD—H???A
0.86
0.97
1.97
2.69
2.645 (3)
3.580 (5)
135
152
Data collection: SMART (Bruker, 2001); cell refinement: SAINT
(Bruker, 2001); 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.
This work was supported by the National Natural Science
Foundation of China (No. 20971076) and the Outstanding
Adult–Young Scientific Research Encouraging Foundation of
Shandong Province, China (No. 2008BS0901).
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: BV2169).
References
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin,
USA.
Lehn, J. M. (1995). Supramolecular Chemistry, p. 61. New York: VCH
Publisher.
Sheldrick, G. M. (1996). SADABS. University of Go ¨ttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Wen, Y. H., Lahiri, S., Qin, Z., Wu, X. L. & Liu, W. S. (2002). J. Radioanal.
Nucl. Chem. 253, 263–265.
Wen, Y.-H., Li, M.-J., Zhang, S.-S. & Li, X.-M. (2005). Acta Cryst. E61, o3373–
o3374.
Wen, Y.-H., Zhang, K. & Zhang, S. S. (2008). J. Coord. Chem. 61, 1157–1164.
organic compounds
Acta Cryst. (2011). E67, o455 doi:10.1107/S1600536811002212 Wen and Dai
o455
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368

Page 2

supplementary materials

Page 3

supplementary materials
sup-1
Acta Cryst. (2011). E67, o455 [ doi:10.1107/S1600536811002212 ]
N,N'-Dibenzyl-2,2'-(3,6-dioxaoctane-1,8-diyldioxy)dibenzamide
Y.-H. Wen and J.-M. Dai
Comment
Increasing attention has focused on acyclic polyether compounds, due to their complexing ability (Wen et al., 2008), se-
lectivity (Wen et al., 2002) to metal ions and their potential application in supramolecular chemistry (Lehn et al., 1995). In
our ongoing studies of structures and properties of diamide-type acyclic polyethers, a new flexible acyclic polyether ligand
3,6-dioxa-1,8-octylenedi(N-benzyl-salicylamide) was synthesized. Herein we report the synthesis and structure of the title
compound, (Fig. 1).
The title compound crystallizes in the monoclinic space group P21/c. The asymmetric unit of the title compound con-
tains one half-molecule, the other half being related by a crystallographic center of inversion (Fig. 1). All bond lengths
and angles in the title compound are within normal ranges, and comparable with those in the related compounds (Wen et
al., 2005, & Wen et al., 2008). In the asymmetric unit, the dihedral angle between two benzene rings is 86.19 (2)°. An
intramolecular N(1)—H(1)···O(2) hydrogen bond (Table 1) forms a six-numbered ring, and affects the conformation of the
molecule which thus adopts a folded rather than open conformation. The crystal packing is stabilized by intermolecular
C(15)—H(15B)···O(1) short-contact interactions (Table 1).
Experimental
The title compound was synthesized according to literature method (Wen et al., 2008). Colourless single cystals suitable for
X-ray diffraction were obtained by slow evaporation of an ethanol solution over a period of 5 d.
Refinement
H atoms were positioned geometrically, with N—H = 0.86 Å and C—H = 0.95–0.99 Å, respectively, and constrained to
ride on their parent atoms, with Uiso(H) = 1.2 Ueq(C,N). In the refinement, SIMU was used to restraint the displacement
parameters of the atoms N1, C7, C6, C5, C1, C2 and C3 to move similarly.
Figures
Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability
displacement ellipsoids, Unlabelled atoms are related to labelled atoms by the symmetry oper-
ator (1 - x,2 - y,-z).

Page 4

supplementary materials
sup-2
Fig. 2. The packing diagram of the title compound, viewed down the a axis.
N,N'-Dibenzyl-2,2'-(3,6-dioxaoctane-1,8-diyldioxy)dibenzamide
Crystal data
C34H36N2O6
F(000) = 604
Dx = 1.229 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 1307 reflections
θ = 2.6–20.3°
µ = 0.08 mm−1
T = 294 K
Prism, colourless
Mr = 568.65
Monoclinic, P21/c
Hall symbol: -P 2ybc
a = 12.065 (3) Å
b = 15.964 (4) Å
c = 8.251 (2) Å
β = 104.820 (5)°
V = 1536.3 (7) Å3
Z = 2
0.24 × 0.20 × 0.16 mm
Data collection
Bruker SMART CCD area-detector
diffractometer
Radiation source: fine-focus sealed tube
graphite
φ and ω scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
Tmin = 0.976, Tmax = 0.983
7850 measured reflections
2707 independent reflections
1284 reflections with I > 2σ(I)
Rint = 0.041
θmax = 25.0°, θmin = 1.8°
h = −14→14
k = −18→18
l = −7→9
Refinement
Refinement on F2
Primary atom site location: structure-invariant direct
methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring
sites
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.048
wR(F2) = 0.149
H-atom parameters constrained
S = 1.00
w = 1/[σ2(Fo2) + (0.0574P)2 + 0.3181P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.21 e Å−3
2707 reflections
190 parameters

Page 5

supplementary materials
sup-3
36 restraints
Δρmin = −0.17 e Å−3
Special details
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 mat-
rix. 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, convention-
al 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)
x
0.8814 (2)
0.83284 (14)
0.63670 (17)
0.7835 (2)
0.7665
0.5392 (3)
0.5756
0.4202 (4)
0.3780
0.3657 (3)
0.2861
0.4281 (3)
0.3913
0.5463 (3)
0.5878
0.6031 (3)
0.7328 (3)
0.7619
0.7564
0.8553 (3)
0.9030 (2)
0.9664 (3)
0.9754
1.0157 (3)
1.0576
1.0031 (2)
1.0360
0.9419 (2)
0.9334
0.8926 (2)
0.8169 (2)
y
0.90823 (13)
1.05219 (11)
1.03915 (16)
0.91898 (14)
0.9504
0.7869 (2)
0.7521
0.7860 (3)
0.7504
0.8361 (2)
0.8355
0.88690 (19)
0.9219
0.88771 (18)
0.9235
0.83769 (17)
0.83619 (18)
0.8074
0.8045
0.94947 (19)
1.03553 (16)
1.0684 (2)
1.0363
1.1460 (2)
1.1658
1.1942 (2)
1.2472
1.16458 (18)
1.1978
1.08525 (17)
1.09965 (18)
z
0.7723 (3)
0.3438 (2)
0.0958 (3)
0.5028 (3)
0.4152
0.3307 (5)
0.2699
0.2970 (5)
0.2147
0.3827 (5)
0.3603
0.5011 (4)
0.5611
0.5347 (4)
0.6172
0.4504 (4)
0.4915 (5)
0.5974
0.4057
0.6421 (4)
0.6358 (3)
0.7883 (4)
0.8848
0.8009 (4)
0.9045
0.6606 (4)
0.6687
0.5074 (4)
0.4124
0.4938 (3)
0.1928 (3)
Uiso*/Ueq
0.1004 (8)
0.0662 (5)
0.0971 (8)
0.0738 (7)
0.089*
0.1097 (13)
0.132*
0.1218 (14)
0.146*
0.0925 (10)
0.111*
0.0820 (10)
0.098*
0.0750 (9)
0.090*
0.0670 (8)
0.0901 (10)
0.108*
0.108*
0.0679 (8)
0.0562 (7)
0.0741 (9)
0.089*
0.0831 (10)
0.100*
0.0752 (9)
0.090*
0.0644 (8)
0.077*
0.0549 (7)
0.0706 (8)
O1
O2
O3
N1
H1
C1
H1A
C2
H2
C3
H3
C4
H4
C5
H5
C6
C7
H7B
H7A
C8
C9
C10
H10
C11
H11
C12
H12
C13
H13
C14
C15