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The title compound, C24H24N2O6, crystallizes in the triclinic space group P\overline1 with two half molecules in the asymmetric unit. The two independent molecules differ in the orientation of the carbonyl group. In the crystal packing, the molecules are linked into chains via intermolecular N—H...O interactions. The packing is further stabilized by C—H...π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804032180/ci6494sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804032180/ci6494Isup2.hkl
Contains datablock I

CCDC reference: 262458

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.068
  • wR factor = 0.185
  • Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.61 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.28 Ratio
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.93 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.37 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21 PLAT480_ALERT_4_C Long H...A H-Bond Reported H12 .. CG2 .. 2.89 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H13 .. CG3 .. 2.96 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C24 H24 N2 O6 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C24 H24 N2 O6
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 10 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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, 1990).

N,N'-Bis(p-methoxyphenyl)-2,2'-(p-phenylenedioxy)diacetamide top
Crystal data top
C24H24N2O6Z = 2
Mr = 436.45F(000) = 460
Triclinic, P1Dx = 1.342 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.8370 (7) ÅCell parameters from 6061 reflections
b = 10.1922 (8) Åθ = 1.9–28.0°
c = 10.9181 (8) ŵ = 0.10 mm1
α = 94.327 (1)°T = 293 K
β = 92.633 (1)°Block, colourless
γ = 97.719 (1)°0.34 × 0.22 × 0.16 mm
V = 1079.90 (14) Å3
Data collection top
Simens SMART 1000 CCD area-detector
diffractometer
4932 independent reflections
Radiation source: fine-focus sealed tube3671 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 8.33 pixels mm-1θmax = 28.0°, θmin = 1.9°
ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1313
Tmin = 0.968, Tmax = 0.985l = 1414
9528 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0865P)2 + 0.3355P]
where P = (Fo2 + 2Fc2)/3
4932 reflections(Δ/σ)max < 0.001
291 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.27 e Å3
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
xyzUiso*/Ueq
O10.3564 (3)0.05594 (19)0.36651 (17)0.0928 (7)
O20.8140 (3)0.0000 (3)0.3642 (2)0.1136 (9)
O30.18321 (16)0.3795 (2)0.05510 (16)0.0691 (5)
O40.68859 (16)0.32820 (19)0.10362 (17)0.0717 (5)
O50.42053 (15)0.39082 (15)0.28693 (13)0.0515 (4)
O60.89964 (17)0.37242 (15)0.30145 (14)0.0558 (4)
N10.39026 (17)0.30968 (18)0.06615 (15)0.0476 (4)
H10.46390.31150.10590.057*
N20.90288 (18)0.30275 (18)0.03154 (16)0.0505 (4)
H20.98800.32260.04620.061*
C10.3591 (5)0.0823 (3)0.3675 (3)0.1213 (16)
H1A0.27860.12940.32300.182*
H1B0.36090.10610.45090.182*
H1C0.43960.10520.32920.182*
C20.3627 (3)0.1106 (2)0.2562 (2)0.0568 (6)
C30.3733 (3)0.2477 (2)0.2626 (2)0.0578 (6)
H30.37320.29550.33860.069*
C40.3840 (2)0.3134 (2)0.1578 (2)0.0492 (5)
H4A0.39310.40570.16300.059*
C50.38145 (19)0.2427 (2)0.04446 (18)0.0432 (5)
C60.3683 (2)0.1066 (2)0.0378 (2)0.0530 (5)
H60.36510.05890.03860.064*
C70.3596 (3)0.0393 (2)0.1430 (2)0.0587 (6)
H70.35180.05300.13770.070*
C80.2882 (2)0.3689 (2)0.10900 (19)0.0480 (5)
C90.3041 (2)0.4280 (2)0.2308 (2)0.0517 (5)
H9A0.22280.39760.28440.062*
H9B0.31310.52400.21810.062*
C100.5796 (2)0.4236 (2)0.43729 (18)0.0450 (5)
H100.63340.37160.39490.054*
C110.4555 (2)0.44659 (19)0.39396 (17)0.0414 (4)
C120.3746 (2)0.5234 (2)0.45705 (19)0.0459 (5)
H120.29010.53910.42840.055*
C131.0098 (2)0.4229 (2)0.60864 (19)0.0486 (5)
H131.01600.37090.68130.058*
C140.9613 (2)0.3652 (2)0.5063 (2)0.0497 (5)
H140.93510.27380.51040.060*
C150.9508 (2)0.4412 (2)0.39733 (19)0.0457 (5)
C160.8804 (2)0.4487 (2)0.19098 (19)0.0519 (5)
H16A0.82210.51570.20750.062*
H16B0.96810.49300.15480.062*
C170.8131 (2)0.3534 (2)0.1040 (2)0.0499 (5)
C180.8761 (2)0.2212 (2)0.06565 (19)0.0465 (5)
C190.9773 (3)0.1497 (3)0.1030 (2)0.0635 (6)
H191.05820.15320.06180.076*
C200.9597 (3)0.0731 (3)0.2011 (3)0.0749 (8)
H201.02800.02410.22540.090*
C210.8399 (3)0.0690 (3)0.2635 (2)0.0688 (7)
C220.7405 (3)0.1414 (3)0.2275 (2)0.0643 (7)
H220.66090.14000.27050.077*
C230.7567 (2)0.2164 (2)0.1284 (2)0.0532 (5)
H230.68750.26400.10360.064*
C240.8739 (7)0.1017 (4)0.3829 (5)0.166 (2)
H24A0.87840.15310.30620.248*
H24B0.82280.15530.43840.248*
H24C0.96520.07280.41810.248*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.162 (2)0.0622 (12)0.0520 (11)0.0002 (12)0.0020 (12)0.0197 (9)
O20.145 (2)0.115 (2)0.0908 (17)0.0239 (17)0.0162 (15)0.0539 (15)
O30.0419 (9)0.1080 (14)0.0649 (11)0.0223 (9)0.0151 (7)0.0281 (10)
O40.0412 (9)0.1012 (14)0.0734 (12)0.0041 (8)0.0012 (8)0.0246 (10)
O50.0514 (8)0.0638 (9)0.0459 (8)0.0206 (7)0.0115 (6)0.0195 (7)
O60.0701 (10)0.0540 (9)0.0439 (8)0.0082 (7)0.0086 (7)0.0053 (7)
N10.0407 (9)0.0616 (11)0.0437 (9)0.0114 (8)0.0113 (7)0.0124 (8)
N20.0386 (9)0.0643 (11)0.0500 (10)0.0078 (8)0.0082 (7)0.0091 (9)
C10.217 (5)0.069 (2)0.078 (2)0.006 (2)0.001 (3)0.0347 (17)
C20.0696 (15)0.0529 (13)0.0463 (12)0.0002 (11)0.0005 (10)0.0092 (10)
C30.0748 (16)0.0534 (13)0.0421 (12)0.0010 (11)0.0024 (11)0.0024 (10)
C40.0530 (12)0.0431 (11)0.0510 (12)0.0035 (9)0.0043 (9)0.0045 (9)
C50.0357 (10)0.0520 (12)0.0433 (11)0.0079 (8)0.0056 (8)0.0084 (9)
C60.0611 (13)0.0548 (13)0.0432 (11)0.0108 (10)0.0053 (10)0.0015 (10)
C70.0719 (15)0.0434 (12)0.0597 (14)0.0055 (11)0.0003 (11)0.0047 (10)
C80.0365 (10)0.0604 (13)0.0474 (12)0.0044 (9)0.0045 (8)0.0088 (10)
C90.0437 (11)0.0653 (14)0.0496 (12)0.0139 (10)0.0067 (9)0.0148 (10)
C100.0454 (11)0.0486 (11)0.0440 (11)0.0157 (9)0.0018 (8)0.0095 (9)
C110.0442 (10)0.0426 (10)0.0376 (10)0.0069 (8)0.0006 (8)0.0047 (8)
C120.0411 (10)0.0553 (12)0.0447 (11)0.0153 (9)0.0047 (8)0.0088 (9)
C130.0541 (12)0.0511 (12)0.0410 (11)0.0115 (10)0.0006 (9)0.0001 (9)
C140.0559 (12)0.0437 (11)0.0490 (12)0.0077 (9)0.0002 (9)0.0018 (9)
C150.0438 (11)0.0531 (12)0.0417 (11)0.0117 (9)0.0016 (8)0.0069 (9)
C160.0526 (12)0.0588 (13)0.0447 (12)0.0090 (10)0.0046 (9)0.0043 (10)
C170.0427 (11)0.0610 (13)0.0456 (12)0.0070 (9)0.0027 (9)0.0030 (10)
C180.0440 (11)0.0533 (12)0.0411 (11)0.0034 (9)0.0045 (8)0.0011 (9)
C190.0545 (14)0.0740 (16)0.0664 (16)0.0159 (12)0.0110 (11)0.0161 (13)
C200.0732 (17)0.0805 (19)0.0764 (18)0.0214 (14)0.0021 (14)0.0246 (15)
C210.0829 (19)0.0720 (17)0.0503 (14)0.0003 (14)0.0057 (13)0.0155 (12)
C220.0573 (14)0.0826 (18)0.0498 (13)0.0036 (13)0.0099 (11)0.0050 (12)
C230.0467 (12)0.0636 (14)0.0482 (12)0.0055 (10)0.0036 (9)0.0003 (10)
C240.274 (7)0.096 (3)0.136 (4)0.045 (4)0.008 (4)0.040 (3)
Geometric parameters (Å, º) top
O1—C21.365 (3)C9—H9A0.97
O1—C11.413 (4)C9—H9B0.97
O2—C241.284 (5)C10—C111.372 (3)
O2—C211.365 (3)C10—C12i1.379 (3)
O3—C81.225 (2)C10—H100.93
O4—C171.217 (3)C11—C121.386 (3)
O5—C111.375 (2)C12—C10i1.379 (3)
O5—C91.406 (2)C12—H120.93
O6—C151.380 (2)C13—C141.377 (3)
O6—C161.419 (3)C13—C15ii1.383 (3)
N1—C81.324 (3)C13—H130.93
N1—C51.432 (2)C14—C151.386 (3)
N1—H10.86C14—H140.93
N2—C171.339 (3)C15—C13ii1.383 (3)
N2—C181.409 (3)C16—C171.520 (3)
N2—H20.86C16—H16A0.97
C1—H1A0.96C16—H16B0.97
C1—H1B0.96C18—C191.375 (3)
C1—H1C0.96C18—C231.384 (3)
C2—C31.383 (3)C19—C201.377 (3)
C2—C71.383 (3)C19—H190.93
C3—C41.370 (3)C20—C211.385 (4)
C3—H30.93C20—H200.93
C4—C51.382 (3)C21—C221.363 (4)
C4—H4A0.93C22—C231.374 (3)
C5—C61.373 (3)C22—H220.93
C6—C71.381 (3)C23—H230.93
C6—H60.93C24—H24A0.96
C7—H70.93C24—H24B0.96
C8—C91.507 (3)C24—H24C0.96
C2—O1—C1118.3 (2)C10—C11—C12119.85 (18)
C24—O2—C21120.6 (4)O5—C11—C12124.08 (18)
C11—O5—C9117.37 (15)C10i—C12—C11119.38 (18)
C15—O6—C16116.90 (17)C10i—C12—H12120.3
C8—N1—C5121.82 (17)C11—C12—H12120.3
C8—N1—H1119.1C14—C13—C15ii119.59 (19)
C5—N1—H1119.1C14—C13—H13120.2
C17—N2—C18128.47 (18)C15ii—C13—H13120.2
C17—N2—H2115.8C13—C14—C15121.0 (2)
C18—N2—H2115.8C13—C14—H14119.5
O1—C1—H1A109.5C15—C14—H14119.5
O1—C1—H1B109.5O6—C15—C13ii124.86 (19)
H1A—C1—H1B109.5O6—C15—C14115.76 (19)
O1—C1—H1C109.5C13ii—C15—C14119.4 (2)
H1A—C1—H1C109.5O6—C16—C17107.15 (18)
H1B—C1—H1C109.5O6—C16—H16A110.3
O1—C2—C3115.4 (2)C17—C16—H16A110.3
O1—C2—C7124.8 (2)O6—C16—H16B110.3
C3—C2—C7119.8 (2)C17—C16—H16B110.3
C4—C3—C2120.4 (2)H16A—C16—H16B108.5
C4—C3—H3119.8O4—C17—N2125.2 (2)
C2—C3—H3119.8O4—C17—C16121.1 (2)
C3—C4—C5120.1 (2)N2—C17—C16113.69 (18)
C3—C4—H4A120.0C19—C18—C23119.4 (2)
C5—C4—H4A120.0C19—C18—N2117.73 (19)
C6—C5—C4119.50 (19)C23—C18—N2122.8 (2)
C6—C5—N1119.66 (19)C18—C19—C20120.4 (2)
C4—C5—N1120.84 (19)C18—C19—H19119.8
C5—C6—C7120.9 (2)C20—C19—H19119.8
C5—C6—H6119.5C19—C20—C21119.8 (3)
C7—C6—H6119.5C19—C20—H20120.1
C6—C7—C2119.2 (2)C21—C20—H20120.1
C6—C7—H7120.4C22—C21—O2115.7 (3)
C2—C7—H7120.4C22—C21—C20119.7 (2)
O3—C8—N1124.0 (2)O2—C21—C20124.6 (3)
O3—C8—C9118.49 (19)C21—C22—C23120.7 (2)
N1—C8—C9117.48 (17)C21—C22—H22119.7
O5—C9—C8110.61 (17)C23—C22—H22119.7
O5—C9—H9A109.5C22—C23—C18120.0 (2)
C8—C9—H9A109.5C22—C23—H23120.0
O5—C9—H9B109.5C18—C23—H23120.0
C8—C9—H9B109.5O2—C24—H24A109.5
H9A—C9—H9B108.1O2—C24—H24B109.5
C11—C10—C12i120.77 (18)H24A—C24—H24B109.5
C11—C10—H10119.6O2—C24—H24C109.5
C12i—C10—H10119.6H24A—C24—H24C109.5
C10—C11—O5116.07 (17)H24B—C24—H24C109.5
C1—O1—C2—C3173.9 (3)C15ii—C13—C14—C150.3 (3)
C1—O1—C2—C75.8 (5)C16—O6—C15—C13ii3.2 (3)
O1—C2—C3—C4178.2 (2)C16—O6—C15—C14176.51 (19)
C7—C2—C3—C41.5 (4)C13—C14—C15—O6179.46 (19)
C2—C3—C4—C51.3 (4)C13—C14—C15—C13ii0.3 (3)
C3—C4—C5—C60.1 (3)C15—O6—C16—C17175.41 (17)
C3—C4—C5—N1179.0 (2)C18—N2—C17—O46.0 (4)
C8—N1—C5—C6108.6 (2)C18—N2—C17—C16174.1 (2)
C8—N1—C5—C470.5 (3)O6—C16—C17—O489.5 (3)
C4—C5—C6—C71.0 (3)O6—C16—C17—N290.5 (2)
N1—C5—C6—C7180.0 (2)C17—N2—C18—C19161.1 (2)
C5—C6—C7—C20.8 (4)C17—N2—C18—C2322.7 (3)
O1—C2—C7—C6179.2 (2)C23—C18—C19—C200.7 (4)
C3—C2—C7—C60.5 (4)N2—C18—C19—C20177.0 (2)
C5—N1—C8—O35.1 (3)C18—C19—C20—C210.8 (4)
C5—N1—C8—C9175.76 (19)C24—O2—C21—C22157.3 (4)
C11—O5—C9—C8174.49 (17)C24—O2—C21—C2025.1 (6)
O3—C8—C9—O5171.9 (2)C19—C20—C21—C220.2 (4)
N1—C8—C9—O58.9 (3)C19—C20—C21—O2177.7 (3)
C12i—C10—C11—O5179.03 (19)O2—C21—C22—C23179.0 (2)
C12i—C10—C11—C120.3 (3)C20—C21—C22—C231.2 (4)
C9—O5—C11—C10171.12 (19)C21—C22—C23—C181.3 (4)
C9—O5—C11—C128.2 (3)C19—C18—C23—C220.3 (3)
C10—C11—C12—C10i0.3 (3)N2—C18—C23—C22175.8 (2)
O5—C11—C12—C10i178.98 (19)
Symmetry codes: (i) x+1, y+1, z1; (ii) x+2, y+1, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O40.862.192.965 (2)149
N1—H1···O50.862.242.624 (2)107
N2—H2···O3iii0.861.942.793 (2)172
C23—H23···O40.932.402.941 (3)117
C3—H3···Cg1iv0.932.753.57147
C12—H12···Cg2v0.932.893.67142
C13—H13···Cg3vi0.932.963.72140
Symmetry codes: (iii) x+1, y, z; (iv) x, y, z+1; (v) x1, y, z; (vi) x, y, z1.
 

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