N,N′-Bis[(3,4-methyl­enedioxy­phen­yl)methyl­ene]phenyl­ene-1,4-diamine

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.

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

No syntax errors found



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

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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: 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

Crystal data

C22H20N2O4	F(000) = 396
Mr = 376.40	Dx = 1.425 Mg m^−3
Monoclinic, P21/c	Melting point: 453 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.2255 (14) Å	Cell parameters from 1254 reflections
b = 4.9257 (16) Å	θ = 2.9–26.7°
c = 12.7837 (18) Å	µ = 0.10 mm^−1
β = 101.624 (3)°	T = 298 K
V = 877.4 (3) Å^3	Columnar, yellow
Z = 2	0.50 × 0.41 × 0.13 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	1532 independent reflections
Radiation source: fine-focus sealed tube	1037 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
φ and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
Tmin = 0.952, Tmax = 0.987	k = −5→5
4222 measured reflections	l = −12→15

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.136	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.067P)^2 + 0.1742P] where P = (Fo^2 + 2Fc^2)/3
1532 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.24 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
N1	0.43167 (13)	0.8565 (4)	0.32950 (16)	0.0546 (6)
H1	0.4683	0.8965	0.2858	0.066*
O1	0.05355 (11)	0.2744 (4)	0.08789 (12)	0.0557 (5)
O2	0.19647 (11)	0.3153 (4)	0.02910 (13)	0.0596 (5)
C1	0.56156 (15)	0.6203 (5)	0.44539 (18)	0.0463 (6)
H1A	0.6043	0.7009	0.4086	0.056*
C2	0.46439 (15)	0.6807 (5)	0.41489 (17)	0.0413 (6)
C3	0.40329 (15)	0.5544 (5)	0.47193 (17)	0.0453 (6)
H3	0.3377	0.5883	0.4540	0.054*
C4	0.33596 (17)	0.9717 (5)	0.3143 (2)	0.0566 (7)
H4A	0.3346	1.1394	0.2743	0.068*
H4B	0.3222	1.0160	0.3837	0.068*
C5	0.25803 (16)	0.7855 (5)	0.25625 (18)	0.0440 (6)
C6	0.27212 (15)	0.6405 (5)	0.16722 (17)	0.0423 (6)
H6	0.3291	0.6545	0.1425	0.051*
C7	0.19907 (15)	0.4767 (5)	0.11737 (17)	0.0404 (6)
C8	0.11377 (15)	0.4524 (5)	0.15223 (17)	0.0422 (6)
C9	0.09735 (16)	0.5940 (5)	0.23785 (19)	0.0518 (7)
H9	0.0395	0.5802	0.2608	0.062*
C10	0.17149 (17)	0.7616 (5)	0.29000 (19)	0.0523 (7)
H10	0.1626	0.8603	0.3492	0.063*
C11	0.10699 (16)	0.1769 (6)	0.0131 (2)	0.0546 (7)
H11A	0.0715	0.2082	−0.0590	0.066*
H11B	0.1177	−0.0168	0.0226	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0492 (12)	0.0602 (14)	0.0499 (12)	−0.0066 (10)	−0.0006 (9)	0.0147 (11)
O1	0.0443 (9)	0.0689 (12)	0.0538 (10)	−0.0138 (8)	0.0095 (8)	−0.0061 (9)
O2	0.0525 (10)	0.0726 (13)	0.0572 (11)	−0.0149 (9)	0.0195 (8)	−0.0181 (9)
C1	0.0407 (12)	0.0528 (15)	0.0454 (14)	−0.0076 (11)	0.0088 (10)	0.0046 (12)
C2	0.0445 (13)	0.0378 (13)	0.0376 (12)	−0.0070 (10)	−0.0016 (10)	−0.0020 (11)
C3	0.0366 (12)	0.0495 (15)	0.0472 (14)	−0.0020 (11)	0.0022 (10)	0.0008 (12)
C4	0.0602 (16)	0.0425 (15)	0.0584 (16)	0.0008 (12)	−0.0088 (12)	0.0068 (13)
C5	0.0454 (13)	0.0364 (13)	0.0449 (13)	0.0064 (10)	−0.0035 (10)	0.0072 (11)
C6	0.0372 (12)	0.0395 (14)	0.0489 (14)	0.0010 (10)	0.0060 (10)	0.0056 (11)
C7	0.0395 (12)	0.0435 (14)	0.0373 (13)	0.0039 (10)	0.0059 (9)	0.0032 (11)
C8	0.0367 (12)	0.0464 (15)	0.0418 (13)	0.0004 (10)	0.0039 (10)	0.0075 (11)
C9	0.0438 (13)	0.0613 (17)	0.0521 (15)	0.0047 (13)	0.0136 (11)	0.0019 (13)
C10	0.0586 (15)	0.0522 (16)	0.0455 (14)	0.0094 (13)	0.0088 (11)	−0.0040 (13)
C11	0.0491 (14)	0.0554 (17)	0.0581 (15)	−0.0056 (12)	0.0078 (11)	−0.0050 (13)

Geometric parameters (Å, º)

N1—C2	1.398 (3)	C4—H4A	0.9700
N1—C4	1.452 (3)	C4—H4B	0.9700
N1—H1	0.8600	C5—C10	1.389 (3)
O1—C8	1.377 (3)	C5—C6	1.392 (3)
O1—C11	1.420 (3)	C6—C7	1.367 (3)
O2—C7	1.375 (3)	C6—H6	0.9300
O2—C11	1.422 (3)	C7—C8	1.380 (3)
C1—C3^i	1.376 (3)	C8—C9	1.357 (3)
C1—C2	1.391 (3)	C9—C10	1.398 (3)
C1—H1A	0.9300	C9—H9	0.9300
C2—C3	1.389 (3)	C10—H10	0.9300
C3—C1^i	1.376 (3)	C11—H11A	0.9700
C3—H3	0.9300	C11—H11B	0.9700
C4—C5	1.513 (3)
C2—N1—C4	120.1 (2)	C6—C5—C4	120.0 (2)
C2—N1—H1	119.9	C7—C6—C5	117.6 (2)
C4—N1—H1	119.9	C7—C6—H6	121.2
C8—O1—C11	105.35 (16)	C5—C6—H6	121.2
C7—O2—C11	105.70 (17)	C6—C7—O2	128.03 (19)
C3^i—C1—C2	122.4 (2)	C6—C7—C8	122.4 (2)
C3^i—C1—H1A	118.8	O2—C7—C8	109.57 (19)
C2—C1—H1A	118.8	C9—C8—O1	128.4 (2)
C3—C2—C1	116.7 (2)	C9—C8—C7	121.4 (2)
C3—C2—N1	122.9 (2)	O1—C8—C7	110.13 (19)
C1—C2—N1	120.5 (2)	C8—C9—C10	116.9 (2)
C1^i—C3—C2	120.9 (2)	C8—C9—H9	121.6
C1^i—C3—H3	119.5	C10—C9—H9	121.6
C2—C3—H3	119.5	C5—C10—C9	122.2 (2)
N1—C4—C5	113.8 (2)	C5—C10—H10	118.9
N1—C4—H4A	108.8	C9—C10—H10	118.9
C5—C4—H4A	108.8	O1—C11—O2	109.05 (19)
N1—C4—H4B	108.8	O1—C11—H11A	109.9
C5—C4—H4B	108.8	O2—C11—H11A	109.9
H4A—C4—H4B	107.7	O1—C11—H11B	109.9
C10—C5—C6	119.5 (2)	O2—C11—H11B	109.9
C10—C5—C4	120.4 (2)	H11A—C11—H11B	108.3
C3^i—C1—C2—C3	−0.3 (4)	C11—O2—C7—C8	−2.9 (2)
C3^i—C1—C2—N1	−179.1 (2)	C11—O1—C8—C9	−178.1 (2)
C4—N1—C2—C3	16.5 (3)	C11—O1—C8—C7	2.6 (2)
C4—N1—C2—C1	−164.7 (2)	C6—C7—C8—C9	0.9 (3)
C1—C2—C3—C1^i	0.3 (4)	O2—C7—C8—C9	−179.2 (2)
N1—C2—C3—C1^i	179.1 (2)	C6—C7—C8—O1	−179.79 (19)
C2—N1—C4—C5	−82.8 (3)	O2—C7—C8—O1	0.1 (2)
N1—C4—C5—C10	138.1 (2)	O1—C8—C9—C10	179.7 (2)
N1—C4—C5—C6	−43.1 (3)	C7—C8—C9—C10	−1.1 (3)
C10—C5—C6—C7	−0.7 (3)	C6—C5—C10—C9	0.5 (3)
C4—C5—C6—C7	−179.56 (19)	C4—C5—C10—C9	179.3 (2)
C5—C6—C7—O2	−179.8 (2)	C8—C9—C10—C5	0.4 (4)
C5—C6—C7—C8	0.1 (3)	C8—O1—C11—O2	−4.4 (2)
C11—O2—C7—C6	177.1 (2)	C7—O2—C11—O1	4.5 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2^ii	0.93	2.76	3.657 (3)	162

Symmetry code: (ii) x, −y+3/2, z+1/2.