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In the title compound, C22H20N2O4, the mol­ecule is centrosymmetric. The mol­ecules are linked by one C—H...O and one C—H...π inter­action into an [001] chain of R22(30) rings and an [010] chain of R22(22) rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806052755/hg2148sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806052755/hg2148Isup2.hkl
Contains datablock I

CCDC reference: 628482

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.047
  • wR factor = 0.136
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1 ... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H10 .. O2 .. 2.76 Ang.
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 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 0 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

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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.

N,N'-Bis[(3,4-methylenedioxyphenyl)methylene]phenylene-1,4-diamine top
Crystal data top
C22H20N2O4F(000) = 396
Mr = 376.40Dx = 1.425 Mg m3
Monoclinic, P21/cMelting point: 453 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 14.2255 (14) ÅCell parameters from 1254 reflections
b = 4.9257 (16) Åθ = 2.9–26.7°
c = 12.7837 (18) ŵ = 0.10 mm1
β = 101.624 (3)°T = 298 K
V = 877.4 (3) Å3Columnar, yellow
Z = 20.50 × 0.41 × 0.13 mm
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
1532 independent reflections
Radiation source: fine-focus sealed tube1037 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1616
Tmin = 0.952, Tmax = 0.987k = 55
4222 measured reflectionsl = 1215
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.067P)2 + 0.1742P]
where P = (Fo2 + 2Fc2)/3
1532 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.24 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
N10.43167 (13)0.8565 (4)0.32950 (16)0.0546 (6)
H10.46830.89650.28580.066*
O10.05355 (11)0.2744 (4)0.08789 (12)0.0557 (5)
O20.19647 (11)0.3153 (4)0.02910 (13)0.0596 (5)
C10.56156 (15)0.6203 (5)0.44539 (18)0.0463 (6)
H1A0.60430.70090.40860.056*
C20.46439 (15)0.6807 (5)0.41489 (17)0.0413 (6)
C30.40329 (15)0.5544 (5)0.47193 (17)0.0453 (6)
H30.33770.58830.45400.054*
C40.33596 (17)0.9717 (5)0.3143 (2)0.0566 (7)
H4A0.33461.13940.27430.068*
H4B0.32221.01600.38370.068*
C50.25803 (16)0.7855 (5)0.25625 (18)0.0440 (6)
C60.27212 (15)0.6405 (5)0.16722 (17)0.0423 (6)
H60.32910.65450.14250.051*
C70.19907 (15)0.4767 (5)0.11737 (17)0.0404 (6)
C80.11377 (15)0.4524 (5)0.15223 (17)0.0422 (6)
C90.09735 (16)0.5940 (5)0.23785 (19)0.0518 (7)
H90.03950.58020.26080.062*
C100.17149 (17)0.7616 (5)0.29000 (19)0.0523 (7)
H100.16260.86030.34920.063*
C110.10699 (16)0.1769 (6)0.0131 (2)0.0546 (7)
H11A0.07150.20820.05900.066*
H11B0.11770.01680.02260.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0492 (12)0.0602 (14)0.0499 (12)0.0066 (10)0.0006 (9)0.0147 (11)
O10.0443 (9)0.0689 (12)0.0538 (10)0.0138 (8)0.0095 (8)0.0061 (9)
O20.0525 (10)0.0726 (13)0.0572 (11)0.0149 (9)0.0195 (8)0.0181 (9)
C10.0407 (12)0.0528 (15)0.0454 (14)0.0076 (11)0.0088 (10)0.0046 (12)
C20.0445 (13)0.0378 (13)0.0376 (12)0.0070 (10)0.0016 (10)0.0020 (11)
C30.0366 (12)0.0495 (15)0.0472 (14)0.0020 (11)0.0022 (10)0.0008 (12)
C40.0602 (16)0.0425 (15)0.0584 (16)0.0008 (12)0.0088 (12)0.0068 (13)
C50.0454 (13)0.0364 (13)0.0449 (13)0.0064 (10)0.0035 (10)0.0072 (11)
C60.0372 (12)0.0395 (14)0.0489 (14)0.0010 (10)0.0060 (10)0.0056 (11)
C70.0395 (12)0.0435 (14)0.0373 (13)0.0039 (10)0.0059 (9)0.0032 (11)
C80.0367 (12)0.0464 (15)0.0418 (13)0.0004 (10)0.0039 (10)0.0075 (11)
C90.0438 (13)0.0613 (17)0.0521 (15)0.0047 (13)0.0136 (11)0.0019 (13)
C100.0586 (15)0.0522 (16)0.0455 (14)0.0094 (13)0.0088 (11)0.0040 (13)
C110.0491 (14)0.0554 (17)0.0581 (15)0.0056 (12)0.0078 (11)0.0050 (13)
Geometric parameters (Å, º) top
N1—C21.398 (3)C4—H4A0.9700
N1—C41.452 (3)C4—H4B0.9700
N1—H10.8600C5—C101.389 (3)
O1—C81.377 (3)C5—C61.392 (3)
O1—C111.420 (3)C6—C71.367 (3)
O2—C71.375 (3)C6—H60.9300
O2—C111.422 (3)C7—C81.380 (3)
C1—C3i1.376 (3)C8—C91.357 (3)
C1—C21.391 (3)C9—C101.398 (3)
C1—H1A0.9300C9—H90.9300
C2—C31.389 (3)C10—H100.9300
C3—C1i1.376 (3)C11—H11A0.9700
C3—H30.9300C11—H11B0.9700
C4—C51.513 (3)
C2—N1—C4120.1 (2)C6—C5—C4120.0 (2)
C2—N1—H1119.9C7—C6—C5117.6 (2)
C4—N1—H1119.9C7—C6—H6121.2
C8—O1—C11105.35 (16)C5—C6—H6121.2
C7—O2—C11105.70 (17)C6—C7—O2128.03 (19)
C3i—C1—C2122.4 (2)C6—C7—C8122.4 (2)
C3i—C1—H1A118.8O2—C7—C8109.57 (19)
C2—C1—H1A118.8C9—C8—O1128.4 (2)
C3—C2—C1116.7 (2)C9—C8—C7121.4 (2)
C3—C2—N1122.9 (2)O1—C8—C7110.13 (19)
C1—C2—N1120.5 (2)C8—C9—C10116.9 (2)
C1i—C3—C2120.9 (2)C8—C9—H9121.6
C1i—C3—H3119.5C10—C9—H9121.6
C2—C3—H3119.5C5—C10—C9122.2 (2)
N1—C4—C5113.8 (2)C5—C10—H10118.9
N1—C4—H4A108.8C9—C10—H10118.9
C5—C4—H4A108.8O1—C11—O2109.05 (19)
N1—C4—H4B108.8O1—C11—H11A109.9
C5—C4—H4B108.8O2—C11—H11A109.9
H4A—C4—H4B107.7O1—C11—H11B109.9
C10—C5—C6119.5 (2)O2—C11—H11B109.9
C10—C5—C4120.4 (2)H11A—C11—H11B108.3
C3i—C1—C2—C30.3 (4)C11—O2—C7—C82.9 (2)
C3i—C1—C2—N1179.1 (2)C11—O1—C8—C9178.1 (2)
C4—N1—C2—C316.5 (3)C11—O1—C8—C72.6 (2)
C4—N1—C2—C1164.7 (2)C6—C7—C8—C90.9 (3)
C1—C2—C3—C1i0.3 (4)O2—C7—C8—C9179.2 (2)
N1—C2—C3—C1i179.1 (2)C6—C7—C8—O1179.79 (19)
C2—N1—C4—C582.8 (3)O2—C7—C8—O10.1 (2)
N1—C4—C5—C10138.1 (2)O1—C8—C9—C10179.7 (2)
N1—C4—C5—C643.1 (3)C7—C8—C9—C101.1 (3)
C10—C5—C6—C70.7 (3)C6—C5—C10—C90.5 (3)
C4—C5—C6—C7179.56 (19)C4—C5—C10—C9179.3 (2)
C5—C6—C7—O2179.8 (2)C8—C9—C10—C50.4 (4)
C5—C6—C7—C80.1 (3)C8—O1—C11—O24.4 (2)
C11—O2—C7—C6177.1 (2)C7—O2—C11—O14.5 (3)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O2ii0.932.763.657 (3)162
Symmetry code: (ii) x, y+3/2, z+1/2.
 

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