N,N′-Dibenzyl-2,2′-ethyl­enedioxy­dibenzamide

The asymmetric unit of the title compound, C₃₀H₂₈N₂O₄, contains one-half of the centrosymmetric mol­ecule. All bond lengths and angles show normal values. Weak inter­molecular N—H...O hydrogen bonds link mol­ecules related by translation along the a axis into chains.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.069
• wR factor = 0.207
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

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Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C6
PLAT322_ALERT_2_C Check Hybridisation of  H15B   in Main Residue .          ?
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C1     -C6            1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The acyclic polyether compounds have good complexing ability and high selectivity to metal ions. Of which diamide-type acyclic polyethers have been used successfully as the active materials for ion-selective electrodes and extractants for metal ions (West et al., 1992; Bunzli et al., 1984; Wen et al., 2002). Recently, in our ongoing studies of structures and properties of the rare earth complexes with diamide-type acyclic polyethers (Wen & Zhang, 2007), a new flexible acyclic polyether compound 1,2-ethylenedioxy-bis(N-phenylmethyl-benzamide) (I), was synthesized. Herein we report the synthesis and structural characterization of (I).

The asymmetric part of the title compound contains a half of the centrosymmetric molecule, with the midpoint of the C15—C15ⁱⁱ bond [symmetry code: (ii): 1 - x, 1 - y, -z] located on an invesrion center (Fig. 1). All bond lengths and angles in (I) show normal values (Allen et al., 1987).

In the crystal structure, molecules are linked into chains along a axis by weak N—H···O intermolecular hydrogen bonds (Table 1 and Fig. 2).

Related literature

The structure of 1,2-ethylenedioxy-bis(N-pyridin-2-ylmethyl-benzamide) was reported by Wen & Zhang (2007). For general background, see: West et al. (1992); Bunzli et al. (1984); Wen et al. (2002); Allen et al. (1987).

S2. Experimental

1,2-Dichloroethane (0.99 g, 0.01 mol) was added dropwise to a 50 ml of DMF solution containing 2-hydroxy-N-phenylmethyl-benzamide (4.54 g, 0.02 mol), K₂CO₃ (3 g, 0.02 mol) and KI (0.5 g), and the mixture was stirred at 328 K for 48 h. After cooling to room temperature, the mixture was filtered. DMF was removed from the filtrate under reduced pressure, and the reside was washed by column chromatography (silica gel, C₂H₅OH:CH₃CO₂C₂H₅ = 1:4) resulting in a colourless solid. Colourless single crystals of (I) suitable for X-ray diffraction study were obtained by slow evaporation of an ethanol–DMF (1:1 v/v) solution over a period of 25 d.

S3. Refinement

All H atoms were located in difference Fourier maps, placed in idealized positions (C—H 0.93–0.98 Å, N—H 0.86 Å) and refined as riding, with U_iso(H) = 1.2 U_eq(C, N).

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures

	Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids and the atom numbering scheme [symmetry code: (A) 1 - x, 1 - y, 1 - z].
	Fig. 2. A packing diagram of (I), viewed down the c axis. Hydrogen bonds are indicated by dashed lines.

N,N'-Dibenzyl-2,2'-ethylenedioxydibenzamide

Crystal data

C30H28N2O4	F(000) = 508
Mr = 480.54	Dx = 1.285 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.0620 (13) Å	Cell parameters from 934 reflections
b = 16.401 (4) Å	θ = 2.5–21.0°
c = 15.056 (4) Å	µ = 0.09 mm^−1
β = 96.522 (5)°	T = 293 K
V = 1241.9 (6) Å^3	Block, colourless
Z = 2	0.42 × 0.11 × 0.05 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	2341 independent reflections
Radiation source: fine-focus sealed tube	1425 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 8.33 pixels mm^-1	θmax = 25.7°, θmin = 1.8°
ω scans	h = −6→5
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −19→16
Tmin = 0.989, Tmax = 0.996	l = −18→17
6638 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.207	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
2341 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.33 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 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 (Ų)

	x	y	z	Uiso*/Ueq
O2	0.2700 (4)	0.43132 (12)	0.04071 (12)	0.0539 (6)
C14	0.1064 (5)	0.36654 (17)	0.01572 (19)	0.0478 (7)
C9	−0.0472 (5)	0.33705 (16)	0.08071 (19)	0.0465 (7)
C8	−0.0383 (6)	0.36742 (17)	0.1743 (2)	0.0490 (7)
N1	0.1948 (5)	0.39077 (16)	0.21573 (16)	0.0590 (7)
H1A	0.3314	0.3884	0.1867	0.071*
O1	−0.2399 (4)	0.36622 (16)	0.21280 (15)	0.0808 (8)
C15	0.4239 (5)	0.46574 (17)	−0.02322 (18)	0.0511 (8)
H15B	0.4287	0.4489	−0.0820	0.077*
H15C	0.3052	0.4862	−0.0725	0.077*
C6	0.3986 (6)	0.4961 (2)	0.3189 (2)	0.0564 (8)
C10	−0.2248 (6)	0.27390 (19)	0.0563 (2)	0.0642 (9)
H10A	−0.3315	0.2546	0.0981	0.077*
C13	0.0843 (6)	0.3322 (2)	−0.0687 (2)	0.0622 (9)
H13A	0.1851	0.3524	−0.1118	0.075*
C11	−0.2482 (8)	0.2393 (2)	−0.0265 (3)	0.0785 (11)
H11A	−0.3693	0.1974	−0.0409	0.094*
C12	−0.0899 (7)	0.2673 (2)	−0.0889 (3)	0.0752 (11)
H12A	−0.0996	0.2426	−0.1448	0.090*
C5	0.3608 (7)	0.5599 (2)	0.2607 (2)	0.0712 (10)
H5A	0.2302	0.5562	0.2121	0.085*
C4	0.5126 (9)	0.6296 (2)	0.2724 (3)	0.0817 (11)
H4A	0.4830	0.6725	0.2321	0.098*
C7	0.2325 (7)	0.4201 (2)	0.3075 (2)	0.0742 (10)
H7A	0.3172	0.3776	0.3455	0.089*
H7B	0.0599	0.4309	0.3271	0.089*
C3	0.7041 (8)	0.6360 (3)	0.3422 (3)	0.0908 (13)
H3A	0.8067	0.6830	0.3497	0.109*
C2	0.7467 (9)	0.5735 (3)	0.4013 (3)	0.1026 (15)
H2A	0.8778	0.5778	0.4496	0.123*
C1	0.5938 (7)	0.5033 (2)	0.3893 (2)	0.0802 (11)
H1B	0.6244	0.4605	0.4296	0.096*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0512 (12)	0.0616 (13)	0.0498 (12)	−0.0147 (10)	0.0101 (9)	0.0019 (10)
C14	0.0360 (16)	0.0464 (17)	0.0594 (18)	0.0058 (13)	−0.0022 (13)	0.0022 (14)
C9	0.0309 (14)	0.0425 (16)	0.0642 (18)	0.0008 (12)	−0.0022 (13)	0.0092 (14)
C8	0.0359 (16)	0.0505 (17)	0.0605 (18)	−0.0012 (13)	0.0054 (14)	0.0150 (14)
N1	0.0405 (15)	0.0810 (19)	0.0568 (15)	−0.0144 (13)	0.0107 (12)	−0.0051 (13)
O1	0.0422 (14)	0.125 (2)	0.0772 (16)	−0.0098 (13)	0.0160 (12)	0.0040 (14)
C15	0.0481 (17)	0.063 (2)	0.0423 (15)	−0.0055 (14)	0.0058 (13)	0.0110 (13)
C6	0.0483 (18)	0.069 (2)	0.0524 (17)	−0.0021 (15)	0.0071 (14)	−0.0054 (16)
C10	0.0497 (19)	0.0531 (19)	0.086 (2)	−0.0065 (15)	−0.0081 (17)	0.0112 (18)
C13	0.056 (2)	0.071 (2)	0.059 (2)	0.0062 (17)	0.0014 (15)	−0.0096 (17)
C11	0.072 (3)	0.054 (2)	0.104 (3)	−0.0091 (18)	−0.013 (2)	−0.007 (2)
C12	0.072 (2)	0.068 (2)	0.079 (2)	0.015 (2)	−0.017 (2)	−0.024 (2)
C5	0.066 (2)	0.083 (3)	0.063 (2)	−0.0006 (19)	−0.0006 (17)	−0.0004 (19)
C4	0.093 (3)	0.067 (2)	0.088 (3)	−0.002 (2)	0.018 (2)	−0.005 (2)
C7	0.071 (2)	0.096 (3)	0.056 (2)	−0.019 (2)	0.0081 (17)	0.0016 (18)
C3	0.078 (3)	0.070 (3)	0.126 (4)	−0.006 (2)	0.015 (3)	−0.034 (3)
C2	0.088 (3)	0.096 (3)	0.113 (4)	0.007 (3)	−0.031 (3)	−0.038 (3)
C1	0.084 (3)	0.080 (3)	0.071 (2)	0.006 (2)	−0.019 (2)	−0.0083 (19)

Geometric parameters (Å, º)

O2—C14	1.373 (3)	C10—H10A	0.9300
O2—C15	1.422 (3)	C13—C12	1.394 (5)
C14—C13	1.383 (4)	C13—H13A	0.9300
C14—C9	1.403 (4)	C11—C12	1.380 (5)
C9—C10	1.393 (4)	C11—H11A	0.9300
C9—C8	1.491 (4)	C12—H12A	0.9300
C8—O1	1.229 (3)	C5—C4	1.378 (5)
C8—N1	1.327 (4)	C5—H5A	0.9300
N1—C7	1.455 (4)	C4—C3	1.350 (5)
N1—H1A	0.8600	C4—H4A	0.9300
C15—C15^i	1.491 (5)	C7—H7A	0.9700
C15—H15B	0.9300	C7—H7B	0.9700
C15—H15C	0.9599	C3—C2	1.358 (6)
C6—C5	1.364 (5)	C3—H3A	0.9300
C6—C1	1.369 (4)	C2—C1	1.388 (6)
C6—C7	1.503 (5)	C2—H2A	0.9300
C10—C11	1.362 (5)	C1—H1B	0.9300
C14—O2—C15	118.8 (2)	C10—C11—C12	119.2 (3)
O2—C14—C13	123.4 (3)	C10—C11—H11A	120.4
O2—C14—C9	116.1 (2)	C12—C11—H11A	120.4
C13—C14—C9	120.5 (3)	C11—C12—C13	120.5 (3)
C10—C9—C14	117.7 (3)	C11—C12—H12A	119.8
C10—C9—C8	116.6 (3)	C13—C12—H12A	119.8
C14—C9—C8	125.8 (3)	C6—C5—C4	121.2 (3)
O1—C8—N1	121.7 (3)	C6—C5—H5A	119.4
O1—C8—C9	120.1 (3)	C4—C5—H5A	119.4
N1—C8—C9	118.1 (3)	C3—C4—C5	120.3 (4)
C8—N1—C7	123.7 (3)	C3—C4—H4A	119.8
C8—N1—H1A	118.1	C5—C4—H4A	119.8
C7—N1—H1A	118.1	N1—C7—C6	113.2 (3)
O2—C15—C15^i	106.0 (3)	N1—C7—H7A	108.9
O2—C15—H15B	127.0	C6—C7—H7A	108.9
C15^i—C15—H15B	127.0	N1—C7—H7B	108.9
O2—C15—H15C	108.6	C6—C7—H7B	108.9
C15^i—C15—H15C	110.1	H7A—C7—H7B	107.7
H15B—C15—H15C	56.6	C4—C3—C2	119.9 (4)
C5—C6—C1	117.9 (3)	C4—C3—H3A	120.1
C5—C6—C7	121.8 (3)	C2—C3—H3A	120.1
C1—C6—C7	120.3 (3)	C3—C2—C1	119.7 (4)
C11—C10—C9	122.5 (3)	C3—C2—H2A	120.1
C11—C10—H10A	118.7	C1—C2—H2A	120.1
C9—C10—H10A	118.7	C6—C1—C2	121.0 (4)
C14—C13—C12	119.6 (3)	C6—C1—H1B	119.5
C14—C13—H13A	120.2	C2—C1—H1B	119.5
C12—C13—H13A	120.2
C15—O2—C14—C13	0.5 (4)	C9—C14—C13—C12	−0.7 (4)
C15—O2—C14—C9	−177.9 (2)	C9—C10—C11—C12	0.3 (5)
O2—C14—C9—C10	177.0 (2)	C10—C11—C12—C13	−2.5 (5)
C13—C14—C9—C10	−1.4 (4)	C14—C13—C12—C11	2.7 (5)
O2—C14—C9—C8	−2.9 (4)	C1—C6—C5—C4	−0.4 (5)
C13—C14—C9—C8	178.7 (3)	C7—C6—C5—C4	179.3 (3)
C10—C9—C8—O1	−31.8 (4)	C6—C5—C4—C3	0.3 (6)
C14—C9—C8—O1	148.1 (3)	C8—N1—C7—C6	−134.0 (3)
C10—C9—C8—N1	144.3 (3)	C5—C6—C7—N1	44.4 (4)
C14—C9—C8—N1	−35.8 (4)	C1—C6—C7—N1	−135.9 (3)
O1—C8—N1—C7	−2.8 (5)	C5—C4—C3—C2	−0.3 (6)
C9—C8—N1—C7	−178.8 (3)	C4—C3—C2—C1	0.4 (7)
C14—O2—C15—C15^i	179.5 (3)	C5—C6—C1—C2	0.5 (5)
C14—C9—C10—C11	1.7 (5)	C7—C6—C1—C2	−179.2 (4)
C8—C9—C10—C11	−178.4 (3)	C3—C2—C1—C6	−0.5 (6)
O2—C14—C13—C12	−179.0 (3)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^ii	0.86	2.19	2.895 (3)	139

Symmetry code: (ii) x+1, y, z.