N,N′-Bis(p-methyl­phenyl)-2,2′-(p-phenyl­enedioxy)diacet­amide

In the title centrosymmetric compound, C₂₄H₂₄N₂O₄, the mol­ecules are linked into a three-dimensional network through intermolecular N—H...O interactions. The crystal packing is further stabilized by C—H...π interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• R factor = 0.062
• wR factor = 0.195
• Data-to-parameter ratio = 10.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.98 Deg.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.66
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ......         C1
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

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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).

2,2'-[1,4-phenylenebis(oxy)]-bis[N-p-methylphenyl(acetamide)]

Crystal data

C24H24N2O4	F(000) = 428
Mr = 404.46	Dx = 1.264 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.8881 (14) Å	Cell parameters from 2022 reflections
b = 10.081 (2) Å	θ = 3.3–25.0°
c = 15.312 (3) Å	µ = 0.09 mm^−1
β = 91.68 (3)°	T = 293 K
V = 1062.8 (4) Å^3	Block, light brown
Z = 2	0.32 × 0.24 × 0.22 mm

Data collection

Simens SMART 1000 CCD area detector diffractometer	1859 independent reflections
Radiation source: fine-focus sealed tube	1556 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
Detector resolution: 8.33 pixels mm^-1	θmax = 25.0°, θmin = 2.4°
ω scans	h = −8→0
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→0
Tmin = 0.973, Tmax = 0.981	l = −18→18
2048 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.195	w = 1/[σ^2(Fo^2) + (0.1185P)^2 + 0.4468P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1859 reflections	Δρmax = 0.36 e Å^−3
173 parameters	Δρmin = −0.28 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.038 (8)

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	0.0016 (2)	0.27325 (18)	0.22215 (13)	0.0668 (6)
O2	0.1845 (2)	0.06445 (19)	0.39083 (11)	0.0576 (6)
N1	−0.1010 (3)	0.0744 (2)	0.27399 (13)	0.0459 (5)
H1N1	−0.067 (4)	0.006 (3)	0.3049 (18)	0.055 (8)*
C1	−0.8208 (4)	−0.0246 (4)	0.08341 (19)	0.0772 (10)
H1A	−0.8366	0.0372	0.0360	0.116*
H1B	−0.9272	−0.0156	0.1221	0.116*
H1C	−0.8186	−0.1133	0.0607	0.116*
C2	−0.6307 (3)	0.0037 (3)	0.13328 (16)	0.0532 (7)
C3	−0.5740 (3)	−0.0719 (3)	0.20499 (17)	0.0523 (7)
H3	−0.650 (5)	−0.145 (3)	0.2204 (19)	0.075 (9)*
C4	−0.3999 (3)	−0.0467 (2)	0.25098 (16)	0.0470 (6)
H4	−0.365 (4)	−0.106 (3)	0.3004 (17)	0.057 (7)*
C5	−0.2784 (3)	0.0550 (2)	0.22422 (14)	0.0416 (6)
C6	−0.3335 (3)	0.1320 (3)	0.15329 (16)	0.0551 (7)
H6	−0.267 (5)	0.209 (3)	0.1380 (18)	0.065 (8)*
C7	−0.5093 (4)	0.1052 (3)	0.10845 (17)	0.0625 (8)
H7	−0.540 (4)	0.160 (3)	0.059 (2)	0.074 (9)*
C8	0.0216 (3)	0.1777 (2)	0.27050 (15)	0.0448 (6)
C9	0.1996 (3)	0.1718 (2)	0.33228 (16)	0.0481 (6)
H9B	0.208 (4)	0.259 (3)	0.3593 (19)	0.068 (8)*
H9A	0.318 (4)	0.162 (3)	0.2943 (17)	0.057 (7)*
C10	0.3455 (3)	0.0362 (2)	0.44476 (14)	0.0447 (6)
C11	0.3279 (3)	−0.0705 (3)	0.49940 (15)	0.0499 (6)
H11	0.214 (4)	−0.121 (3)	0.4958 (16)	0.061 (7)*
C12	0.5185 (3)	0.1091 (3)	0.44485 (15)	0.0491 (6)
H12	0.533 (4)	0.189 (3)	0.4108 (17)	0.054 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0467 (10)	0.0527 (11)	0.0988 (14)	−0.0049 (7)	−0.0324 (9)	0.0153 (10)
O2	0.0326 (9)	0.0773 (13)	0.0614 (10)	−0.0101 (7)	−0.0237 (7)	0.0133 (8)
N1	0.0316 (10)	0.0512 (12)	0.0535 (11)	−0.0017 (8)	−0.0184 (8)	0.0029 (9)
C1	0.0368 (13)	0.125 (3)	0.0682 (17)	−0.0055 (15)	−0.0204 (12)	−0.0184 (17)
C2	0.0279 (11)	0.0782 (17)	0.0528 (13)	0.0002 (11)	−0.0099 (9)	−0.0135 (12)
C3	0.0327 (12)	0.0569 (15)	0.0669 (15)	−0.0044 (10)	−0.0078 (10)	−0.0085 (11)
C4	0.0344 (11)	0.0496 (13)	0.0565 (13)	0.0023 (9)	−0.0103 (9)	−0.0023 (10)
C5	0.0261 (10)	0.0502 (12)	0.0478 (12)	0.0015 (9)	−0.0118 (8)	−0.0055 (9)
C6	0.0410 (13)	0.0698 (17)	0.0535 (13)	−0.0088 (12)	−0.0154 (10)	0.0087 (12)
C7	0.0453 (14)	0.088 (2)	0.0527 (14)	−0.0002 (13)	−0.0192 (11)	0.0094 (14)
C8	0.0303 (11)	0.0467 (13)	0.0566 (13)	0.0048 (9)	−0.0120 (9)	−0.0055 (10)
C9	0.0346 (12)	0.0498 (14)	0.0589 (14)	−0.0006 (9)	−0.0154 (10)	−0.0015 (11)
C10	0.0290 (11)	0.0614 (14)	0.0429 (11)	−0.0033 (9)	−0.0137 (8)	−0.0023 (10)
C11	0.0322 (11)	0.0624 (15)	0.0543 (13)	−0.0112 (10)	−0.0143 (9)	0.0003 (11)
C12	0.0370 (12)	0.0578 (14)	0.0516 (13)	−0.0088 (10)	−0.0137 (9)	0.0035 (11)

Geometric parameters (Å, º)

O1—C8	1.220 (3)	C4—H4	0.99 (3)
O2—C10	1.392 (2)	C5—C6	1.379 (3)
O2—C9	1.411 (3)	C6—C7	1.401 (3)
N1—C8	1.343 (3)	C6—H6	0.93 (3)
N1—C5	1.434 (2)	C7—H7	0.96 (3)
N1—H1N1	0.86 (3)	C8—C9	1.527 (3)
C1—C2	1.524 (3)	C9—H9B	0.97 (3)
C1—H1A	0.9600	C9—H9A	1.02 (3)
C1—H1B	0.9600	C10—C11	1.370 (3)
C1—H1C	0.9600	C10—C12	1.400 (3)
C2—C7	1.381 (4)	C11—C12^i	1.395 (3)
C2—C3	1.383 (4)	C11—H11	0.94 (3)
C3—C4	1.396 (3)	C12—C11^i	1.395 (3)
C3—H3	0.94 (3)	C12—H12	0.97 (3)
C4—C5	1.393 (3)
C10—O2—C9	117.50 (17)	C5—C6—H6	122.8 (19)
C8—N1—C5	127.7 (2)	C7—C6—H6	117.3 (19)
C8—N1—H1N1	118.6 (18)	C2—C7—C6	122.0 (2)
C5—N1—H1N1	113.3 (18)	C2—C7—H7	121.5 (19)
C2—C1—H1A	109.5	C6—C7—H7	116.5 (19)
C2—C1—H1B	109.5	O1—C8—N1	125.17 (19)
H1A—C1—H1B	109.5	O1—C8—C9	118.76 (19)
C2—C1—H1C	109.5	N1—C8—C9	116.1 (2)
H1A—C1—H1C	109.5	O2—C9—C8	110.55 (18)
H1B—C1—H1C	109.5	O2—C9—H9B	115.3 (17)
C7—C2—C3	117.9 (2)	C8—C9—H9B	105.3 (17)
C7—C2—C1	121.3 (2)	O2—C9—H9A	111.4 (15)
C3—C2—C1	120.9 (2)	C8—C9—H9A	106.9 (15)
C2—C3—C4	121.2 (2)	H9B—C9—H9A	107 (2)
C2—C3—H3	119.1 (19)	C11—C10—O2	116.09 (19)
C4—C3—H3	119.6 (19)	C11—C10—C12	120.1 (2)
C5—C4—C3	120.0 (2)	O2—C10—C12	123.8 (2)
C5—C4—H4	122.5 (16)	C10—C11—C12^i	120.9 (2)
C3—C4—H4	117.4 (16)	C10—C11—H11	118.6 (17)
C6—C5—C4	119.5 (2)	C12^i—C11—H11	120.3 (17)
C6—C5—N1	123.5 (2)	C11^i—C12—C10	118.9 (2)
C4—C5—N1	117.0 (2)	C11^i—C12—H12	118.5 (16)
C5—C6—C7	119.4 (2)	C10—C12—H12	122.5 (16)
C7—C2—C3—C4	0.0 (4)	C5—N1—C8—O1	−1.0 (4)
C1—C2—C3—C4	179.9 (2)	C5—N1—C8—C9	179.5 (2)
C2—C3—C4—C5	−0.9 (4)	C10—O2—C9—C8	172.70 (19)
C3—C4—C5—C6	1.4 (4)	O1—C8—C9—O2	172.0 (2)
C3—C4—C5—N1	−179.4 (2)	N1—C8—C9—O2	−8.4 (3)
C8—N1—C5—C6	11.4 (4)	C9—O2—C10—C11	−178.5 (2)
C8—N1—C5—C4	−167.8 (2)	C9—O2—C10—C12	1.0 (3)
C4—C5—C6—C7	−1.1 (4)	O2—C10—C11—C12^i	178.9 (2)
N1—C5—C6—C7	179.7 (2)	C12—C10—C11—C12^i	−0.7 (4)
C3—C2—C7—C6	0.3 (4)	C11—C10—C12—C11^i	0.7 (4)
C1—C2—C7—C6	−179.6 (3)	O2—C10—C12—C11^i	−178.8 (2)
C5—C6—C7—C2	0.2 (4)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2	0.86 (3)	2.22 (3)	2.621 (3)	108 (2)
N1—H1N1···O1^ii	0.86 (3)	2.43 (3)	3.112 (3)	137 (2)
C6—H6···O1	0.93 (3)	2.32 (3)	2.885 (3)	119 (2)
C9—H9A···Cg1^iii	1.02 (3)	2.74	3.68	154

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