N,N′-Dibenzyl-2,2′-(3,6-dioxaoctane-1,8-diyldi­oxy)dibenzamide

Wen, Y.-H.; Dai, J.-M.

doi:10.1107/S1600536811002212

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o455

doi:10.1107/S1600536811002212

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N,N′-Dibenzyl-2,2′-(3,6-dioxaoctane-1,8-diyldioxy)dibenzamide

Yong-Hong Wen ^a ^* and Ji-Min Dai ^a

^aCollege 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; online 22 January 2011)

The title compound, C₃₄H₃₆N₂O₆, located on a center of inversion, crystallizes with one half-molecule in the asymmetric 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 intermolecular 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
M_r = 568.65
Monoclinic, P 2₁ /c
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
Mo Kα radiation
μ = 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 ) T_min = 0.976, T_max = 0.983
7850 measured reflections
2707 independent reflections
1284 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.149
S = 1.00
2707 reflections
190 parameters
36 restraints
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	1.97	2.645 (3)	135
C15—H15B⋯O1ⁱ	0.97	2.69	3.580 (5)	152
Symmetry code: (i) -x+2, -y+2, -z+1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811002212/bv2169sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811002212/bv2169Isup2.hkl

checkCIF report

Comment top

Increasing attention has focused on acyclic polyether compounds, due to their complexing ability (Wen et al., 2008), selectivity (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 contains 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).

Related literature top

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 top

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.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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).

Figures top

	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 operator (1 - x,2 - y,-z).
	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 top

Crystal data top

C₃₄H₃₆N₂O₆	F(000) = 604
M_r = 568.65	D_x = 1.229 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1307 reflections
a = 12.065 (3) Å	θ = 2.6–20.3°
b = 15.964 (4) Å	µ = 0.08 mm⁻¹
c = 8.251 (2) Å	T = 294 K
β = 104.820 (5)°	Prism, colourless
V = 1536.3 (7) Å³	0.24 × 0.20 × 0.16 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	2707 independent reflections
Radiation source: fine-focus sealed tube	1284 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.976, T_max = 0.983	k = −18→18
7850 measured reflections	l = −7→9

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0574P)² + 0.3181P] where P = (F_o² + 2F_c²)/3
2707 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.21 e Å⁻³
36 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₃₄H₃₆N₂O₆	V = 1536.3 (7) Å³
M_r = 568.65	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.065 (3) Å	µ = 0.08 mm⁻¹
b = 15.964 (4) Å	T = 294 K
c = 8.251 (2) Å	0.24 × 0.20 × 0.16 mm
β = 104.820 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2707 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1284 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.983	R_int = 0.041
7850 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	36 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.00	Δρ_max = 0.21 e Å⁻³
2707 reflections	Δρ_min = −0.17 e Å⁻³
190 parameters

Special details top

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
O1	0.8814 (2)	0.90823 (13)	0.7723 (3)	0.1004 (8)
O2	0.83284 (14)	1.05219 (11)	0.3438 (2)	0.0662 (5)
O3	0.63670 (17)	1.03915 (16)	0.0958 (3)	0.0971 (8)
N1	0.7835 (2)	0.91898 (14)	0.5028 (3)	0.0738 (7)
H1	0.7665	0.9504	0.4152	0.089*
C1	0.5392 (3)	0.7869 (2)	0.3307 (5)	0.1097 (13)
H1A	0.5756	0.7521	0.2699	0.132*
C2	0.4202 (4)	0.7860 (3)	0.2970 (5)	0.1218 (14)
H2	0.3780	0.7504	0.2147	0.146*
C3	0.3657 (3)	0.8361 (2)	0.3827 (5)	0.0925 (10)
H3	0.2861	0.8355	0.3603	0.111*
C4	0.4281 (3)	0.88690 (19)	0.5011 (4)	0.0820 (10)
H4	0.3913	0.9219	0.5611	0.098*
C5	0.5463 (3)	0.88771 (18)	0.5347 (4)	0.0750 (9)
H5	0.5878	0.9235	0.6172	0.090*
C6	0.6031 (3)	0.83769 (17)	0.4504 (4)	0.0670 (8)
C7	0.7328 (3)	0.83619 (18)	0.4915 (5)	0.0901 (10)
H7B	0.7619	0.8074	0.5974	0.108*
H7A	0.7564	0.8045	0.4057	0.108*
C8	0.8553 (3)	0.94947 (19)	0.6421 (4)	0.0679 (8)
C9	0.9030 (2)	1.03553 (16)	0.6358 (3)	0.0562 (7)
C10	0.9664 (3)	1.0684 (2)	0.7883 (4)	0.0741 (9)
H10	0.9754	1.0363	0.8848	0.089*
C11	1.0157 (3)	1.1460 (2)	0.8009 (4)	0.0831 (10)
H11	1.0576	1.1658	0.9045	0.100*
C12	1.0031 (2)	1.1942 (2)	0.6606 (4)	0.0752 (9)
H12	1.0360	1.2472	0.6687	0.090*
C13	0.9419 (2)	1.16458 (18)	0.5074 (4)	0.0644 (8)
H13	0.9334	1.1978	0.4124	0.077*
C14	0.8926 (2)	1.08525 (17)	0.4938 (3)	0.0549 (7)
C15	0.8169 (2)	1.09965 (18)	0.1928 (3)	0.0706 (8)
H15B	0.8901	1.1111	0.1691	0.085*
H15A	0.7796	1.1525	0.2029	0.085*
C16	0.7438 (2)	1.0481 (2)	0.0572 (4)	0.0816 (9)
H16B	0.7341	1.0755	−0.0504	0.098*
H16A	0.7786	0.9936	0.0524	0.098*
C17	0.5563 (2)	0.9992 (3)	−0.0245 (4)	0.1032 (12)
H17A	0.5797	0.9418	−0.0352	0.124*
H17B	0.5477	1.0270	−0.1316	0.124*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1298 (19)	0.0877 (16)	0.0854 (16)	0.0126 (13)	0.0307 (15)	0.0363 (13)
O2	0.0697 (12)	0.0723 (12)	0.0529 (12)	−0.0104 (10)	0.0088 (10)	0.0102 (10)
O3	0.0592 (12)	0.166 (2)	0.0638 (13)	−0.0177 (13)	0.0111 (11)	−0.0132 (14)
N1	0.0729 (15)	0.0547 (15)	0.094 (2)	−0.0021 (12)	0.0223 (15)	0.0136 (13)
C1	0.104 (3)	0.111 (3)	0.135 (3)	−0.023 (2)	0.070 (3)	−0.057 (3)
C2	0.109 (3)	0.143 (4)	0.123 (3)	−0.039 (3)	0.048 (3)	−0.060 (3)
C3	0.078 (2)	0.095 (3)	0.112 (3)	−0.005 (2)	0.038 (2)	0.004 (2)
C4	0.093 (3)	0.063 (2)	0.104 (3)	0.0074 (18)	0.052 (2)	0.0007 (19)
C5	0.088 (2)	0.060 (2)	0.082 (2)	0.0002 (16)	0.0303 (19)	−0.0095 (15)
C6	0.080 (2)	0.0470 (17)	0.084 (2)	−0.0002 (15)	0.0404 (18)	0.0021 (15)
C7	0.082 (2)	0.061 (2)	0.136 (3)	0.0042 (17)	0.042 (2)	0.0050 (19)
C8	0.0675 (18)	0.069 (2)	0.072 (2)	0.0162 (16)	0.0270 (17)	0.0122 (18)
C9	0.0540 (15)	0.0587 (17)	0.0592 (18)	0.0141 (13)	0.0206 (14)	0.0100 (14)
C10	0.085 (2)	0.082 (2)	0.056 (2)	0.0255 (18)	0.0178 (17)	0.0048 (17)
C11	0.085 (2)	0.090 (3)	0.072 (2)	0.015 (2)	0.0155 (19)	−0.021 (2)
C12	0.0698 (19)	0.075 (2)	0.083 (2)	−0.0045 (16)	0.0235 (18)	−0.021 (2)
C13	0.0664 (17)	0.0639 (19)	0.068 (2)	−0.0026 (15)	0.0261 (16)	0.0025 (15)
C14	0.0453 (14)	0.0676 (19)	0.0531 (17)	0.0065 (13)	0.0152 (13)	0.0018 (14)
C15	0.0653 (18)	0.087 (2)	0.0589 (18)	−0.0016 (16)	0.0151 (15)	0.0157 (16)
C16	0.0552 (18)	0.129 (3)	0.060 (2)	−0.0024 (18)	0.0141 (16)	0.0139 (19)
C17	0.077 (2)	0.161 (3)	0.071 (2)	−0.031 (2)	0.0201 (19)	−0.019 (2)

Geometric parameters (Å, º) top

O1—C8	1.231 (3)	C7—H7A	0.9700
O2—C14	1.369 (3)	C8—C9	1.496 (4)
O2—C15	1.429 (3)	C9—C14	1.394 (3)
O3—C17	1.356 (3)	C9—C10	1.397 (4)
O3—C16	1.415 (3)	C10—C11	1.365 (4)
N1—C8	1.341 (3)	C10—H10	0.9300
N1—C7	1.449 (3)	C11—C12	1.366 (4)
N1—H1	0.8600	C11—H11	0.9300
C1—C6	1.356 (4)	C12—C13	1.374 (4)
C1—C2	1.392 (5)	C12—H12	0.9300
C1—H1A	0.9300	C13—C14	1.391 (4)
C2—C3	1.345 (4)	C13—H13	0.9300
C2—H2	0.9300	C15—C16	1.484 (4)
C3—C4	1.343 (4)	C15—H15B	0.9700
C3—H3	0.9300	C15—H15A	0.9700
C4—C5	1.381 (4)	C16—H16B	0.9700
C4—H4	0.9300	C16—H16A	0.9700
C5—C6	1.355 (4)	C17—C17ⁱ	1.514 (6)
C5—H5	0.9300	C17—H17A	0.9700
C6—C7	1.514 (4)	C17—H17B	0.9700
C7—H7B	0.9700

C14—O2—C15	120.4 (2)	C10—C9—C8	116.2 (3)
C17—O3—C16	113.9 (2)	C11—C10—C9	122.5 (3)
C8—N1—C7	123.7 (3)	C11—C10—H10	118.8
C8—N1—H1	118.1	C9—C10—H10	118.8
C7—N1—H1	118.1	C10—C11—C12	119.6 (3)
C6—C1—C2	121.1 (3)	C10—C11—H11	120.2
C6—C1—H1A	119.4	C12—C11—H11	120.2
C2—C1—H1A	119.4	C11—C12—C13	120.2 (3)
C3—C2—C1	120.5 (3)	C11—C12—H12	119.9
C3—C2—H2	119.8	C13—C12—H12	119.9
C1—C2—H2	119.8	C12—C13—C14	120.3 (3)
C4—C3—C2	118.9 (3)	C12—C13—H13	119.8
C4—C3—H3	120.5	C14—C13—H13	119.8
C2—C3—H3	120.5	O2—C14—C13	122.6 (2)
C3—C4—C5	120.6 (3)	O2—C14—C9	117.0 (2)
C3—C4—H4	119.7	C13—C14—C9	120.4 (3)
C5—C4—H4	119.7	O2—C15—C16	106.5 (2)
C6—C5—C4	121.6 (3)	O2—C15—H15B	110.4
C6—C5—H5	119.2	C16—C15—H15B	110.4
C4—C5—H5	119.2	O2—C15—H15A	110.4
C5—C6—C1	117.3 (3)	C16—C15—H15A	110.4
C5—C6—C7	121.6 (3)	H15B—C15—H15A	108.6
C1—C6—C7	121.1 (3)	O3—C16—C15	106.7 (2)
N1—C7—C6	113.2 (2)	O3—C16—H16B	110.4
N1—C7—H7B	108.9	C15—C16—H16B	110.4
C6—C7—H7B	108.9	O3—C16—H16A	110.4
N1—C7—H7A	108.9	C15—C16—H16A	110.4
C6—C7—H7A	108.9	H16B—C16—H16A	108.6
H7B—C7—H7A	107.7	O3—C17—C17ⁱ	108.6 (3)
O1—C8—N1	121.3 (3)	O3—C17—H17A	110.0
O1—C8—C9	120.5 (3)	C17ⁱ—C17—H17A	110.0
N1—C8—C9	118.3 (3)	O3—C17—H17B	110.0
C14—C9—C10	117.0 (3)	C17ⁱ—C17—H17B	110.0
C14—C9—C8	126.8 (3)	H17A—C17—H17B	108.3

C6—C1—C2—C3	0.3 (6)	C14—C9—C10—C11	0.7 (4)
C1—C2—C3—C4	0.0 (6)	C8—C9—C10—C11	179.5 (3)
C2—C3—C4—C5	−0.1 (5)	C9—C10—C11—C12	0.2 (5)
C3—C4—C5—C6	−0.1 (5)	C10—C11—C12—C13	−0.5 (5)
C4—C5—C6—C1	0.4 (5)	C11—C12—C13—C14	−0.2 (4)
C4—C5—C6—C7	−177.7 (3)	C15—O2—C14—C13	−1.1 (4)
C2—C1—C6—C5	−0.5 (5)	C15—O2—C14—C9	179.1 (2)
C2—C1—C6—C7	177.6 (3)	C12—C13—C14—O2	−178.7 (2)
C8—N1—C7—C6	119.0 (3)	C12—C13—C14—C9	1.2 (4)
C5—C6—C7—N1	−48.7 (4)	C10—C9—C14—O2	178.5 (2)
C1—C6—C7—N1	133.4 (3)	C8—C9—C14—O2	−0.2 (4)
C7—N1—C8—O1	−1.2 (4)	C10—C9—C14—C13	−1.3 (4)
C7—N1—C8—C9	179.0 (2)	C8—C9—C14—C13	180.0 (2)
O1—C8—C9—C14	171.6 (3)	C14—O2—C15—C16	−176.8 (2)
N1—C8—C9—C14	−8.5 (4)	C17—O3—C16—C15	174.7 (3)
O1—C8—C9—C10	−7.1 (4)	O2—C15—C16—O3	63.9 (3)
N1—C8—C9—C10	172.7 (2)	C16—O3—C17—C17ⁱ	−174.9 (4)

Symmetry code: (i) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.97	2.645 (3)	135
C15—H15B···O1ⁱⁱ	0.97	2.69	3.580 (5)	152

Symmetry code: (ii) −x+2, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₃₄H₃₆N₂O₆
M_r	568.65
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	12.065 (3), 15.964 (4), 8.251 (2)
β (°)	104.820 (5)
V (Å³)	1536.3 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.24 × 0.20 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.976, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	7850, 2707, 1284
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.149, 1.00
No. of reflections	2707
No. of parameters	190
No. of restraints	36
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.17

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.97	2.645 (3)	135
C15—H15B···O1ⁱ	0.97	2.69	3.580 (5)	152

Symmetry code: (i) −x+2, −y+2, −z+1.

Acknowledgements

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).

References

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