N,N,N′N′-Tetra­phenyl-2,2′-(o-phenyl­enedioxy)diacetamide

In the title compound, C₃₄H₂₈N₂O₄, the mol­ecule lies on a crystallographic twofold axis. In the crystal structure, the mol­ecules are linked by C—H...O hydrogen bonds into double chains along the c axis. These chains are inter­linked via C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.042
• wR factor = 0.105
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

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

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

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S1. Comment

In our ongoing study of amide-type polyethers, we have synthesized the title compound, (I). Here, we report its crystal structure.

The asymmetric unit of (I) contains one half-molecule, the other half being related by a crystallographic twofold axis (Fig. 1). Bond lengths in (I) (Table 1) are within normal ranges (Allen et al., 1987). The sum of the angles around atom N1 is 359.9 (1)°, implying a planar configuration. The dihedral angle between the two benzene rings attached to atom N1 is 83.91 (5)°, while these two rings make angles of 62.68 (5) and 54.89 (6)°, respectively, with the central benzene ring.

In the crystal structure, molecules of (I) are linked into double chains along the c axis (Fig. 2) via C11—H11A···O1ⁱ hydrogen bonds (symmetry code as in Table 2). The packing is further stabilized by C—H···π interactions involving the C1—C6 benzene ring (centroid Cg1).

S2. Experimental

Compound (I) was prepared according to the literature method of Wen et al. (2005). Yellow single crystals suitable for X-ray diffraction study were obtained by slow evaporation of a petroleum ether–ethyl acetate solution (1:3, v/v) over a period of 8 d.

S3. Refinement

All H atoms were positioned geometrically and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, and with U_iso(H) = 1.2U_eq(C).

Computing details

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

Figures

	Fig. 1. The structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme. Unlabelled atoms are related to labelled atoms by the symmetry operator (−x, y, 1/2 − z).
	Fig. 2. The crystal packing of (I), showing a hydrogen-bonded (dashed lines) double chain.

N,N,N'N'-Tetraphenyl-2,2'-(o-phenylenedioxy)diacetamide

Crystal data

C34H28N2O4	F(000) = 1112
Mr = 528.58	Dx = 1.290 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2861 reflections
a = 16.0863 (10) Å	θ = 2.4–26.0°
b = 11.0050 (7) Å	µ = 0.09 mm^−1
c = 16.5816 (11) Å	T = 293 K
β = 111.981 (1)°	Plate, yellow
V = 2722.1 (3) Å^3	0.32 × 0.19 × 0.08 mm
Z = 4

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	2674 independent reflections
Radiation source: fine-focus sealed tube	2284 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 2.3°
ω scans	h = −19→19
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→10
Tmin = 0.973, Tmax = 0.993	l = −20→20
7490 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0486P)^2 + 1.2205P] where P = (Fo^2 + 2Fc^2)/3
2674 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.19 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
O1	−0.08276 (7)	0.88789 (10)	0.41861 (7)	0.0523 (3)
O2	0.03323 (7)	0.88280 (8)	0.33434 (6)	0.0430 (3)
N1	0.01455 (7)	0.78979 (10)	0.53511 (7)	0.0389 (3)
C1	−0.05795 (9)	0.74950 (13)	0.56050 (9)	0.0407 (3)
C2	−0.06547 (11)	0.79548 (15)	0.63465 (10)	0.0515 (4)
H2A	−0.0256	0.8541	0.6676	0.062*
C3	−0.13393 (12)	0.7527 (2)	0.65947 (12)	0.0659 (5)
H3A	−0.1396	0.7829	0.7096	0.079*
C4	−0.19284 (11)	0.6669 (2)	0.61084 (13)	0.0692 (5)
H4A	−0.2382	0.6388	0.6280	0.083*
C5	−0.18518 (12)	0.62219 (18)	0.53703 (13)	0.0669 (5)
H5A	−0.2254	0.5639	0.5041	0.080*
C6	−0.11774 (10)	0.66345 (15)	0.51119 (11)	0.0520 (4)
H6A	−0.1128	0.6333	0.4608	0.062*
C7	0.12117 (10)	0.63044 (14)	0.60610 (10)	0.0516 (4)
H7A	0.0762	0.5736	0.5805	0.062*
C8	0.20533 (11)	0.59228 (17)	0.66053 (12)	0.0617 (5)
H8A	0.2167	0.5099	0.6716	0.074*
C9	0.27228 (11)	0.67550 (18)	0.69830 (11)	0.0615 (5)
H9A	0.3288	0.6497	0.7353	0.074*
C10	0.25533 (11)	0.79690 (18)	0.68116 (11)	0.0594 (4)
H10A	0.3011	0.8531	0.7057	0.071*
C11	0.17062 (10)	0.83698 (15)	0.62755 (10)	0.0487 (4)
H11A	0.1591	0.9195	0.6174	0.058*
C12	0.10376 (9)	0.75236 (13)	0.58960 (8)	0.0395 (3)
C13	−0.00662 (9)	0.85424 (12)	0.45982 (8)	0.0381 (3)
C14	0.06795 (10)	0.88352 (13)	0.42687 (9)	0.0422 (3)
H14A	0.0930	0.9628	0.4480	0.051*
H14B	0.1155	0.8237	0.4488	0.051*
C15	0.01612 (9)	0.77037 (12)	0.29556 (8)	0.0359 (3)
C16	0.03030 (10)	0.66109 (13)	0.33950 (9)	0.0452 (3)
H16A	0.0506	0.6606	0.3999	0.054*
C17	0.01451 (10)	0.55188 (13)	0.29432 (10)	0.0494 (4)
H17A	0.0237	0.4787	0.3244	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0463 (6)	0.0643 (7)	0.0448 (6)	0.0101 (5)	0.0154 (5)	0.0123 (5)
O2	0.0606 (6)	0.0391 (5)	0.0321 (5)	−0.0022 (4)	0.0205 (5)	−0.0016 (4)
N1	0.0360 (6)	0.0471 (7)	0.0338 (6)	0.0002 (5)	0.0132 (5)	0.0045 (5)
C1	0.0352 (7)	0.0477 (8)	0.0394 (7)	0.0054 (6)	0.0142 (6)	0.0109 (6)
C2	0.0499 (9)	0.0645 (10)	0.0423 (8)	0.0027 (7)	0.0199 (7)	0.0052 (7)
C3	0.0596 (11)	0.0931 (13)	0.0545 (10)	0.0143 (10)	0.0323 (9)	0.0166 (9)
C4	0.0416 (9)	0.0951 (14)	0.0732 (12)	0.0045 (9)	0.0241 (9)	0.0320 (11)
C5	0.0461 (9)	0.0705 (12)	0.0748 (12)	−0.0106 (8)	0.0120 (9)	0.0169 (9)
C6	0.0460 (8)	0.0550 (9)	0.0515 (9)	−0.0022 (7)	0.0144 (7)	0.0040 (7)
C7	0.0453 (8)	0.0511 (9)	0.0565 (9)	−0.0004 (7)	0.0167 (7)	0.0069 (7)
C8	0.0522 (10)	0.0620 (11)	0.0695 (11)	0.0117 (8)	0.0211 (9)	0.0179 (9)
C9	0.0378 (8)	0.0898 (14)	0.0546 (10)	0.0111 (8)	0.0147 (7)	0.0146 (9)
C10	0.0395 (8)	0.0803 (12)	0.0555 (10)	−0.0093 (8)	0.0145 (7)	−0.0040 (9)
C11	0.0462 (8)	0.0532 (9)	0.0462 (8)	−0.0051 (7)	0.0165 (7)	−0.0014 (7)
C12	0.0367 (7)	0.0506 (8)	0.0330 (7)	0.0014 (6)	0.0151 (6)	0.0037 (6)
C13	0.0423 (8)	0.0393 (7)	0.0320 (7)	0.0008 (6)	0.0133 (6)	−0.0028 (5)
C14	0.0494 (8)	0.0460 (8)	0.0325 (7)	−0.0052 (6)	0.0168 (6)	−0.0028 (6)
C15	0.0377 (7)	0.0378 (7)	0.0366 (7)	0.0002 (5)	0.0189 (6)	−0.0018 (5)
C16	0.0527 (9)	0.0468 (8)	0.0379 (7)	0.0040 (7)	0.0190 (7)	0.0049 (6)
C17	0.0578 (9)	0.0373 (8)	0.0574 (9)	0.0034 (7)	0.0266 (8)	0.0074 (6)

Geometric parameters (Å, º)

O1—C13	1.2157 (16)	C7—H7A	0.93
O2—C15	1.3740 (15)	C8—C9	1.373 (3)
O2—C14	1.4228 (16)	C8—H8A	0.93
N1—C13	1.3635 (17)	C9—C10	1.372 (3)
N1—C12	1.4404 (17)	C9—H9A	0.93
N1—C1	1.4496 (17)	C10—C11	1.391 (2)
C1—C2	1.376 (2)	C10—H10A	0.93
C1—C6	1.379 (2)	C11—C12	1.383 (2)
C2—C3	1.394 (2)	C11—H11A	0.93
C2—H2A	0.93	C13—C14	1.5272 (19)
C3—C4	1.367 (3)	C14—H14A	0.97
C3—H3A	0.93	C14—H14B	0.97
C4—C5	1.367 (3)	C15—C16	1.3802 (19)
C4—H4A	0.93	C15—C15^i	1.402 (3)
C5—C6	1.384 (2)	C16—C17	1.389 (2)
C5—H5A	0.93	C16—H16A	0.93
C6—H6A	0.93	C17—C17^i	1.365 (3)
C7—C12	1.377 (2)	C17—H17A	0.93
C7—C8	1.382 (2)
C15—O2—C14	116.03 (10)	C10—C9—H9A	120.2
C13—N1—C12	124.88 (11)	C8—C9—H9A	120.2
C13—N1—C1	118.21 (11)	C9—C10—C11	120.82 (16)
C12—N1—C1	116.82 (10)	C9—C10—H10A	119.6
C2—C1—C6	120.47 (14)	C11—C10—H10A	119.6
C2—C1—N1	119.76 (13)	C12—C11—C10	119.09 (16)
C6—C1—N1	119.76 (13)	C12—C11—H11A	120.5
C1—C2—C3	118.88 (16)	C10—C11—H11A	120.5
C1—C2—H2A	120.6	C7—C12—C11	119.99 (14)
C3—C2—H2A	120.6	C7—C12—N1	118.95 (13)
C4—C3—C2	120.61 (17)	C11—C12—N1	121.02 (13)
C4—C3—H3A	119.7	O1—C13—N1	121.80 (12)
C2—C3—H3A	119.7	O1—C13—C14	119.71 (12)
C5—C4—C3	120.12 (16)	N1—C13—C14	118.49 (12)
C5—C4—H4A	119.9	O2—C14—C13	109.92 (11)
C3—C4—H4A	119.9	O2—C14—H14A	109.7
C4—C5—C6	120.21 (18)	C13—C14—H14A	109.7
C4—C5—H5A	119.9	O2—C14—H14B	109.7
C6—C5—H5A	119.9	C13—C14—H14B	109.7
C1—C6—C5	119.71 (16)	H14A—C14—H14B	108.2
C1—C6—H6A	120.1	O2—C15—C16	124.96 (12)
C5—C6—H6A	120.1	O2—C15—C15^i	115.66 (6)
C12—C7—C8	120.17 (15)	C16—C15—C15^i	119.37 (8)
C12—C7—H7A	119.9	C15—C16—C17	120.57 (13)
C8—C7—H7A	119.9	C15—C16—H16A	119.7
C9—C8—C7	120.31 (17)	C17—C16—H16A	119.7
C9—C8—H8A	119.8	C17^i—C17—C16	120.04 (9)
C7—C8—H8A	119.8	C17^i—C17—H17A	120.0
C10—C9—C8	119.60 (15)	C16—C17—H17A	120.0
C13—N1—C1—C2	−114.46 (15)	C10—C11—C12—C7	0.9 (2)
C12—N1—C1—C2	68.89 (17)	C10—C11—C12—N1	178.68 (13)
C13—N1—C1—C6	66.92 (17)	C13—N1—C12—C7	−121.45 (15)
C12—N1—C1—C6	−109.74 (15)	C1—N1—C12—C7	54.96 (17)
C6—C1—C2—C3	0.6 (2)	C13—N1—C12—C11	60.79 (18)
N1—C1—C2—C3	−177.97 (13)	C1—N1—C12—C11	−122.81 (14)
C1—C2—C3—C4	−0.2 (3)	C12—N1—C13—O1	−176.65 (13)
C2—C3—C4—C5	−0.1 (3)	C1—N1—C13—O1	7.0 (2)
C3—C4—C5—C6	0.1 (3)	C12—N1—C13—C14	3.8 (2)
C2—C1—C6—C5	−0.7 (2)	C1—N1—C13—C14	−172.59 (12)
N1—C1—C6—C5	177.92 (14)	C15—O2—C14—C13	−75.01 (14)
C4—C5—C6—C1	0.3 (3)	O1—C13—C14—O2	−33.65 (18)
C12—C7—C8—C9	−0.2 (3)	N1—C13—C14—O2	145.93 (12)
C7—C8—C9—C10	−0.5 (3)	C14—O2—C15—C16	−0.14 (19)
C8—C9—C10—C11	1.5 (3)	C14—O2—C15—C15^i	−178.59 (13)
C9—C10—C11—C12	−1.7 (2)	O2—C15—C16—C17	−177.18 (13)
C8—C7—C12—C11	0.0 (2)	C15^i—C15—C16—C17	1.2 (2)
C8—C7—C12—N1	−177.79 (14)	C15—C16—C17—C17^i	0.6 (3)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1^ii	0.93	2.41	3.308 (2)	162
C17—H17A···Cg1^iii	0.93	2.70	3.563 (2)	154

Symmetry codes: (ii) −x, −y+2, −z+1; (iii) −x, −y+1, −z+1.