6,6′-Dimeth­oxy-2,2′-(ethane-1,2-diyldiimino­dimethyl­ene)diphenol

In the crystal structure of the title compound, C₁₈H₂₄O₂N₄, centrosymmetric mol­ecules are linked into a layer via C—H...O and O—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.136
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1C    ..  O2      ..       2.68 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   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
   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.

6,6'-Dimethoxy-2,2'-(ethane-1,2-diyldiiminodimethylene)diphenol

Crystal data

C18H24N2O4	F(000) = 712
Mr = 332.39	Dx = 1.279 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2582 reflections
a = 9.431 (3) Å	θ = 2.3–25.4°
b = 10.512 (4) Å	µ = 0.09 mm^−1
c = 17.414 (6) Å	T = 298 K
V = 1726.4 (10) Å^3	Block, white
Z = 4	0.56 × 0.54 × 0.32 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	1525 independent reflections
Radiation source: fine-focus sealed tube	1104 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.951, Tmax = 0.972	k = −11→12
8220 measured reflections	l = −20→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)] = 0.041	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) + (0.0429P)^2 + 0.7829P] where P = (Fo^2 + 2Fc^2)/3
1525 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.20 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	0.63143 (16)	0.55569 (15)	0.57277 (9)	0.0394 (4)
H1A	0.6755	0.6116	0.5418	0.047*
O1	0.71232 (13)	0.83924 (13)	0.58727 (9)	0.0499 (4)
H1	0.7295	0.9097	0.5694	0.075*
O2	0.55557 (15)	1.05383 (14)	0.58690 (10)	0.0602 (5)
C1	0.6227 (2)	0.6106 (2)	0.65036 (12)	0.0475 (6)
H1C	0.7180	0.6290	0.6681	0.057*
H1D	0.5827	0.5473	0.6846	0.057*
C2	0.5357 (2)	0.7299 (2)	0.65631 (11)	0.0411 (5)
C3	0.58358 (19)	0.84133 (19)	0.62237 (11)	0.0385 (5)
C4	0.4991 (2)	0.9510 (2)	0.62340 (12)	0.0439 (5)
C5	0.3691 (2)	0.9488 (2)	0.65951 (14)	0.0565 (7)
H5	0.3124	1.0212	0.6598	0.068*
C6	0.3230 (3)	0.8392 (3)	0.69528 (15)	0.0666 (7)
H6	0.2363	0.8385	0.7207	0.080*
C7	0.4044 (2)	0.7316 (2)	0.69347 (13)	0.0563 (6)
H7	0.3718	0.6582	0.7174	0.068*
C8	0.4771 (3)	1.1690 (2)	0.58660 (18)	0.0708 (8)
H8A	0.5280	1.2324	0.5581	0.106*
H8B	0.4638	1.1978	0.6384	0.106*
H8C	0.3864	1.1548	0.5631	0.106*
C9	0.4924 (2)	0.52592 (19)	0.54006 (11)	0.0390 (5)
H9A	0.4346	0.6023	0.5389	0.047*
H9B	0.4448	0.4637	0.5721	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0392 (9)	0.0349 (9)	0.0440 (10)	−0.0037 (7)	−0.0117 (7)	−0.0008 (7)
O1	0.0400 (8)	0.0376 (8)	0.0720 (10)	0.0005 (6)	0.0138 (7)	0.0029 (7)
O2	0.0485 (9)	0.0435 (9)	0.0884 (13)	0.0071 (7)	0.0131 (8)	0.0058 (8)
C1	0.0547 (13)	0.0445 (13)	0.0434 (12)	−0.0096 (10)	−0.0148 (10)	0.0031 (10)
C2	0.0456 (11)	0.0451 (12)	0.0326 (11)	−0.0110 (10)	−0.0046 (9)	−0.0065 (9)
C3	0.0338 (10)	0.0427 (12)	0.0390 (11)	−0.0043 (9)	0.0010 (9)	−0.0065 (9)
C4	0.0398 (11)	0.0438 (12)	0.0481 (12)	−0.0027 (10)	0.0005 (9)	−0.0080 (10)
C5	0.0415 (12)	0.0620 (16)	0.0659 (16)	−0.0007 (11)	0.0079 (11)	−0.0221 (13)
C6	0.0507 (13)	0.0824 (19)	0.0668 (17)	−0.0162 (14)	0.0229 (12)	−0.0234 (14)
C7	0.0621 (14)	0.0605 (15)	0.0462 (13)	−0.0262 (13)	0.0110 (11)	−0.0082 (12)
C8	0.0644 (15)	0.0546 (16)	0.093 (2)	0.0182 (13)	−0.0021 (15)	0.0059 (14)
C9	0.0376 (10)	0.0340 (11)	0.0454 (11)	−0.0005 (9)	−0.0084 (9)	−0.0026 (9)

Geometric parameters (Å, º)

N1—C9	1.464 (2)	C4—C5	1.378 (3)
N1—C1	1.472 (3)	C5—C6	1.380 (3)
N1—H1A	0.9000	C5—H5	0.9300
O1—C3	1.359 (2)	C6—C7	1.367 (3)
O1—H1	0.8200	C6—H6	0.9300
O2—C4	1.362 (3)	C7—H7	0.9300
O2—C8	1.419 (3)	C8—H8A	0.9600
C1—C2	1.502 (3)	C8—H8B	0.9600
C1—H1C	0.9700	C8—H8C	0.9600
C1—H1D	0.9700	C9—C9^i	1.505 (4)
C2—C3	1.387 (3)	C9—H9A	0.9700
C2—C7	1.397 (3)	C9—H9B	0.9700
C3—C4	1.402 (3)
C9—N1—C1	113.01 (16)	C4—C5—H5	120.0
C9—N1—H1A	108.6	C6—C5—H5	120.0
C1—N1—H1A	108.7	C7—C6—C5	120.2 (2)
C3—O1—H1	109.5	C7—C6—H6	119.9
C4—O2—C8	118.34 (18)	C5—C6—H6	119.9
N1—C1—C2	114.94 (16)	C6—C7—C2	121.2 (2)
N1—C1—H1C	108.5	C6—C7—H7	119.4
C2—C1—H1C	108.5	C2—C7—H7	119.4
N1—C1—H1D	108.5	O2—C8—H8A	109.5
C2—C1—H1D	108.5	O2—C8—H8B	109.4
H1C—C1—H1D	107.5	H8A—C8—H8B	109.5
C3—C2—C7	118.3 (2)	O2—C8—H8C	109.5
C3—C2—C1	119.87 (18)	H8A—C8—H8C	109.5
C7—C2—C1	121.8 (2)	H8B—C8—H8C	109.5
O1—C3—C2	117.93 (18)	N1—C9—C9^i	110.6 (2)
O1—C3—C4	121.78 (18)	N1—C9—H9A	109.5
C2—C3—C4	120.28 (18)	C9^i—C9—H9A	109.5
O2—C4—C5	125.1 (2)	N1—C9—H9B	109.5
O2—C4—C3	115.13 (17)	C9^i—C9—H9B	109.5
C5—C4—C3	119.8 (2)	H9A—C9—H9B	108.1
C4—C5—C6	120.1 (2)
C9—N1—C1—C2	−57.5 (2)	C2—C3—C4—O2	−178.62 (18)
N1—C1—C2—C3	−68.5 (2)	O1—C3—C4—C5	179.84 (19)
N1—C1—C2—C7	109.5 (2)	C2—C3—C4—C5	1.2 (3)
C7—C2—C3—O1	179.12 (18)	O2—C4—C5—C6	−179.5 (2)
C1—C2—C3—O1	−2.8 (3)	C3—C4—C5—C6	0.7 (3)
C7—C2—C3—C4	−2.2 (3)	C4—C5—C6—C7	−1.6 (4)
C1—C2—C3—C4	175.94 (18)	C5—C6—C7—C2	0.5 (4)
C8—O2—C4—C5	1.2 (3)	C3—C2—C7—C6	1.3 (3)
C8—O2—C4—C3	−179.0 (2)	C1—C2—C7—C6	−176.7 (2)
O1—C3—C4—O2	0.0 (3)	C1—N1—C9—C9^i	178.2 (2)

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
C1—H1C···O2^ii	0.97	2.68	3.284 (3)	121
O1—H1···N1^iii	0.82	2.02	2.723 (2)	144

Symmetry codes: (ii) −x+3/2, y−1/2, z; (iii) −x+3/2, y+1/2, z.