(E,E)-6,6′-Dimeth­oxy-2,2′-[o-phenyl­enebis(nitrilo­methyl­idyne)]diphenol

The title compound, C₂₂H₂₀N₂O₄, consists of two o-vanillin groups connected to a benzene ring via two azomethine linkages. The mol­ecule structure is stabilized by inter­molecular C—H...O and C—H...N inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.063
• wR factor = 0.233
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         47 Perc.
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.65 mm
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9     ..  O2      ..       2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8A    ..  O1      ..       2.69 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6     ..  N2      ..       2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A    ..  O4      ..       2.70 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 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
   3 ALERT type 3 Indicator that the structure quality may be low
   4 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: SMART; data reduction: SAINT (Siemens, 1996); 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.

(E,E)-6,6'-Dimethoxy-2,2'-[o-phenylenebis(nitrilomethylidyne)]diphenol

Crystal data

C22H20N2O4	F(000) = 792
Mr = 376.40	Dx = 1.318 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1361 reflections
a = 6.638 (2) Å	θ = 2.4–25.2°
b = 16.838 (3) Å	µ = 0.09 mm^−1
c = 17.137 (3) Å	T = 298 K
β = 97.861 (3)°	Block, red
V = 1897.3 (7) Å^3	0.65 × 0.13 × 0.09 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3339 independent reflections
Radiation source: fine-focus sealed tube	1566 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.943, Tmax = 0.992	k = −20→19
9506 measured reflections	l = −18→20

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.233	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.058P)^2 + 0.8316P] where P = (Fo^2 + 2Fc^2)/3
3339 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.22 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	0.4698 (5)	0.23511 (18)	0.4737 (2)	0.0524 (9)
N2	0.6943 (5)	0.2879 (2)	0.60674 (18)	0.0516 (9)
O1	0.2192 (4)	0.34248 (16)	0.50485 (15)	0.0599 (8)
H1	0.3243	0.3162	0.5110	0.090*
O2	−0.1181 (5)	0.41871 (18)	0.46705 (16)	0.0635 (9)
O3	0.4395 (5)	0.34123 (17)	0.69958 (17)	0.0670 (9)
H3	0.4850	0.3097	0.6700	0.100*
O4	0.3416 (5)	0.45259 (19)	0.79339 (19)	0.0800 (10)
C1	0.3575 (7)	0.2217 (2)	0.4083 (2)	0.0568 (12)
H1A	0.4000	0.1854	0.3731	0.068*
C2	0.1668 (6)	0.2617 (2)	0.3885 (2)	0.0489 (10)
C3	0.1054 (6)	0.3210 (2)	0.4371 (2)	0.0465 (10)
C4	−0.0792 (6)	0.3598 (2)	0.4167 (2)	0.0474 (10)
C5	−0.2052 (7)	0.3379 (3)	0.3496 (2)	0.0580 (12)
H5	−0.3306	0.3627	0.3366	0.070*
C6	−0.1448 (8)	0.2787 (3)	0.3011 (3)	0.0667 (13)
H6	−0.2296	0.2646	0.2555	0.080*
C7	0.0371 (8)	0.2413 (3)	0.3198 (2)	0.0639 (13)
H7	0.0757	0.2018	0.2869	0.077*
C8	−0.3024 (7)	0.4619 (3)	0.4494 (3)	0.0779 (15)
H8A	−0.3098	0.5017	0.4890	0.117*
H8B	−0.4156	0.4262	0.4485	0.117*
H8C	−0.3065	0.4869	0.3989	0.117*
C9	0.8024 (7)	0.3500 (3)	0.6252 (2)	0.0532 (11)
H9	0.9279	0.3546	0.6072	0.064*
C10	0.7357 (6)	0.4132 (2)	0.6729 (2)	0.0514 (11)
C11	0.5622 (6)	0.4056 (2)	0.7099 (2)	0.0479 (10)
C12	0.5108 (7)	0.4665 (3)	0.7586 (2)	0.0550 (11)
C13	0.6252 (8)	0.5343 (3)	0.7676 (3)	0.0687 (13)
H13	0.5888	0.5748	0.7998	0.082*
C14	0.7933 (9)	0.5432 (3)	0.7297 (3)	0.0822 (15)
H14	0.8679	0.5901	0.7350	0.099*
C15	0.8504 (8)	0.4827 (3)	0.6840 (3)	0.0737 (14)
H15	0.9673	0.4880	0.6601	0.088*
C16	0.2831 (10)	0.5119 (3)	0.8450 (3)	0.111 (2)
H16A	0.1625	0.4951	0.8656	0.166*
H16B	0.2565	0.5608	0.8167	0.166*
H16C	0.3909	0.5198	0.8877	0.166*
C17	0.6584 (7)	0.1979 (2)	0.4961 (2)	0.0506 (11)
C18	0.7774 (7)	0.2271 (2)	0.5633 (2)	0.0512 (11)
C19	0.9654 (7)	0.1943 (3)	0.5877 (3)	0.0664 (13)
H19	1.0447	0.2139	0.6325	0.080*
C20	1.0365 (9)	0.1333 (3)	0.5466 (3)	0.0778 (16)
H20	1.1637	0.1115	0.5635	0.093*
C21	0.9214 (9)	0.1042 (3)	0.4806 (3)	0.0765 (15)
H21	0.9707	0.0628	0.4528	0.092*
C22	0.7348 (8)	0.1357 (3)	0.4553 (3)	0.0697 (14)
H22	0.6577	0.1154	0.4103	0.084*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.053 (2)	0.050 (2)	0.053 (2)	0.0040 (17)	0.0043 (18)	−0.0062 (16)
N2	0.052 (2)	0.059 (2)	0.0426 (19)	0.0083 (18)	0.0034 (16)	0.0036 (16)
O1	0.0552 (19)	0.0673 (19)	0.0525 (17)	0.0129 (15)	−0.0089 (14)	−0.0154 (14)
O2	0.060 (2)	0.076 (2)	0.0523 (17)	0.0197 (16)	0.0010 (15)	−0.0046 (15)
O3	0.065 (2)	0.0631 (19)	0.076 (2)	−0.0020 (16)	0.0219 (17)	−0.0035 (15)
O4	0.091 (3)	0.077 (2)	0.079 (2)	0.0146 (19)	0.037 (2)	0.0025 (17)
C1	0.074 (3)	0.050 (3)	0.046 (3)	0.002 (2)	0.010 (2)	−0.009 (2)
C2	0.053 (3)	0.051 (2)	0.042 (2)	−0.002 (2)	0.001 (2)	−0.0026 (19)
C3	0.048 (3)	0.053 (2)	0.037 (2)	−0.002 (2)	−0.0013 (19)	−0.0016 (19)
C4	0.050 (3)	0.054 (2)	0.038 (2)	0.001 (2)	0.0033 (19)	−0.0021 (18)
C5	0.045 (3)	0.076 (3)	0.050 (3)	−0.002 (2)	−0.004 (2)	0.007 (2)
C6	0.071 (4)	0.076 (3)	0.047 (3)	−0.004 (3)	−0.012 (2)	−0.010 (2)
C7	0.077 (4)	0.065 (3)	0.046 (3)	−0.001 (3)	−0.002 (2)	−0.012 (2)
C8	0.062 (3)	0.083 (3)	0.086 (4)	0.027 (3)	0.004 (3)	−0.003 (3)
C9	0.050 (3)	0.069 (3)	0.040 (2)	0.007 (2)	0.007 (2)	0.009 (2)
C10	0.050 (3)	0.063 (3)	0.041 (2)	0.002 (2)	0.003 (2)	0.004 (2)
C11	0.051 (3)	0.054 (2)	0.038 (2)	0.004 (2)	0.0022 (19)	0.0083 (19)
C12	0.060 (3)	0.067 (3)	0.039 (2)	0.013 (2)	0.010 (2)	0.009 (2)
C13	0.082 (4)	0.068 (3)	0.053 (3)	0.004 (3)	0.002 (3)	−0.008 (2)
C14	0.091 (4)	0.073 (3)	0.083 (4)	−0.017 (3)	0.013 (3)	−0.019 (3)
C15	0.067 (3)	0.082 (3)	0.074 (3)	−0.018 (3)	0.015 (3)	−0.006 (3)
C16	0.144 (6)	0.101 (4)	0.100 (4)	0.026 (4)	0.062 (4)	−0.013 (4)
C17	0.054 (3)	0.048 (2)	0.053 (3)	0.007 (2)	0.016 (2)	0.006 (2)
C18	0.054 (3)	0.055 (3)	0.047 (2)	0.012 (2)	0.013 (2)	0.010 (2)
C19	0.060 (3)	0.079 (3)	0.061 (3)	0.015 (3)	0.010 (2)	0.016 (2)
C20	0.074 (4)	0.082 (4)	0.081 (4)	0.037 (3)	0.023 (3)	0.028 (3)
C21	0.086 (4)	0.070 (3)	0.078 (4)	0.031 (3)	0.028 (3)	0.011 (3)
C22	0.077 (4)	0.062 (3)	0.073 (3)	0.016 (3)	0.019 (3)	−0.006 (2)

Geometric parameters (Å, º)

N1—C1	1.278 (5)	C8—H8C	0.9600
N1—C17	1.406 (5)	C9—C10	1.448 (6)
N2—C9	1.283 (5)	C9—H9	0.9300
N2—C18	1.421 (5)	C10—C15	1.394 (6)
O1—C3	1.345 (4)	C10—C11	1.394 (6)
O1—H1	0.8200	C11—C12	1.394 (5)
O2—C4	1.361 (4)	C12—C13	1.368 (6)
O2—C8	1.420 (5)	C13—C14	1.374 (7)
O3—C11	1.353 (5)	C13—H13	0.9300
O3—H3	0.8200	C14—C15	1.370 (6)
O4—C12	1.362 (5)	C14—H14	0.9300
O4—C16	1.423 (5)	C15—H15	0.9300
C1—C2	1.433 (6)	C16—H16A	0.9600
C1—H1A	0.9300	C16—H16B	0.9600
C2—C3	1.396 (5)	C16—H16C	0.9600
C2—C7	1.403 (5)	C17—C18	1.393 (6)
C3—C4	1.390 (6)	C17—C22	1.394 (6)
C4—C5	1.377 (5)	C18—C19	1.377 (6)
C5—C6	1.391 (6)	C19—C20	1.366 (6)
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.361 (6)	C20—C21	1.366 (7)
C6—H6	0.9300	C20—H20	0.9300
C7—H7	0.9300	C21—C22	1.362 (7)
C8—H8A	0.9600	C21—H21	0.9300
C8—H8B	0.9600	C22—H22	0.9300
C1—N1—C17	123.5 (4)	O3—C11—C12	118.3 (4)
C9—N2—C18	118.2 (4)	O3—C11—C10	122.3 (4)
C3—O1—H1	109.5	C12—C11—C10	119.3 (4)
C4—O2—C8	118.1 (3)	O4—C12—C13	124.9 (4)
C11—O3—H3	109.5	O4—C12—C11	114.9 (4)
C12—O4—C16	117.6 (4)	C13—C12—C11	120.2 (4)
N1—C1—C2	121.0 (4)	C12—C13—C14	120.8 (5)
N1—C1—H1A	119.5	C12—C13—H13	119.6
C2—C1—H1A	119.5	C14—C13—H13	119.6
C3—C2—C7	118.7 (4)	C15—C14—C13	119.7 (5)
C3—C2—C1	121.1 (4)	C15—C14—H14	120.2
C7—C2—C1	120.2 (4)	C13—C14—H14	120.2
O1—C3—C4	117.5 (4)	C14—C15—C10	120.9 (5)
O1—C3—C2	122.1 (4)	C14—C15—H15	119.6
C4—C3—C2	120.4 (4)	C10—C15—H15	119.6
O2—C4—C5	125.3 (4)	O4—C16—H16A	109.5
O2—C4—C3	114.8 (3)	O4—C16—H16B	109.5
C5—C4—C3	119.8 (4)	H16A—C16—H16B	109.5
C4—C5—C6	119.9 (4)	O4—C16—H16C	109.5
C4—C5—H5	120.0	H16A—C16—H16C	109.5
C6—C5—H5	120.0	H16B—C16—H16C	109.5
C7—C6—C5	120.7 (4)	C18—C17—C22	118.5 (4)
C7—C6—H6	119.6	C18—C17—N1	116.8 (4)
C5—C6—H6	119.6	C22—C17—N1	124.7 (4)
C6—C7—C2	120.4 (4)	C19—C18—C17	119.8 (4)
C6—C7—H7	119.8	C19—C18—N2	122.0 (4)
C2—C7—H7	119.8	C17—C18—N2	118.1 (4)
O2—C8—H8A	109.5	C20—C19—C18	120.5 (5)
O2—C8—H8B	109.5	C20—C19—H19	119.7
H8A—C8—H8B	109.5	C18—C19—H19	119.7
O2—C8—H8C	109.5	C21—C20—C19	120.2 (5)
H8A—C8—H8C	109.5	C21—C20—H20	119.9
H8B—C8—H8C	109.5	C19—C20—H20	119.9
N2—C9—C10	122.3 (4)	C22—C21—C20	120.4 (5)
N2—C9—H9	118.8	C22—C21—H21	119.8
C10—C9—H9	118.8	C20—C21—H21	119.8
C15—C10—C11	119.0 (4)	C21—C22—C17	120.6 (5)
C15—C10—C9	119.4 (4)	C21—C22—H22	119.7
C11—C10—C9	121.6 (4)	C17—C22—H22	119.7
C17—N1—C1—C2	−179.8 (4)	C16—O4—C12—C11	178.9 (4)
N1—C1—C2—C3	5.1 (6)	O3—C11—C12—O4	2.1 (5)
N1—C1—C2—C7	−174.4 (4)	C10—C11—C12—O4	−178.5 (3)
C7—C2—C3—O1	178.3 (4)	O3—C11—C12—C13	−176.8 (4)
C1—C2—C3—O1	−1.1 (6)	C10—C11—C12—C13	2.5 (6)
C7—C2—C3—C4	−1.1 (6)	O4—C12—C13—C14	−179.6 (4)
C1—C2—C3—C4	179.4 (4)	C11—C12—C13—C14	−0.7 (7)
C8—O2—C4—C5	−0.4 (6)	C12—C13—C14—C15	−1.8 (8)
C8—O2—C4—C3	179.0 (4)	C13—C14—C15—C10	2.6 (8)
O1—C3—C4—O2	3.1 (5)	C11—C10—C15—C14	−0.8 (7)
C2—C3—C4—O2	−177.4 (3)	C9—C10—C15—C14	−179.1 (4)
O1—C3—C4—C5	−177.4 (3)	C1—N1—C17—C18	170.5 (4)
C2—C3—C4—C5	2.1 (6)	C1—N1—C17—C22	−8.0 (6)
O2—C4—C5—C6	177.5 (4)	C22—C17—C18—C19	−0.1 (6)
C3—C4—C5—C6	−1.9 (6)	N1—C17—C18—C19	−178.8 (4)
C4—C5—C6—C7	0.8 (7)	C22—C17—C18—N2	−177.0 (4)
C5—C6—C7—C2	0.1 (7)	N1—C17—C18—N2	4.3 (5)
C3—C2—C7—C6	0.1 (6)	C9—N2—C18—C19	52.8 (5)
C1—C2—C7—C6	179.5 (4)	C9—N2—C18—C17	−130.4 (4)
C18—N2—C9—C10	−176.6 (3)	C17—C18—C19—C20	0.0 (6)
N2—C9—C10—C15	−173.4 (4)	N2—C18—C19—C20	176.8 (4)
N2—C9—C10—C11	8.3 (6)	C18—C19—C20—C21	0.1 (7)
C15—C10—C11—O3	177.6 (4)	C19—C20—C21—C22	−0.1 (8)
C9—C10—C11—O3	−4.1 (6)	C20—C21—C22—C17	0.0 (7)
C15—C10—C11—C12	−1.8 (6)	C18—C17—C22—C21	0.1 (7)
C9—C10—C11—C12	176.5 (4)	N1—C17—C22—C21	178.7 (4)
C16—O4—C12—C13	−2.2 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2^i	0.93	2.61	3.058 (5)	110
C8—H8A···O1^ii	0.96	2.69	3.413 (6)	133
C6—H6···N2^iii	0.93	2.68	3.540 (5)	154
C1—H1A···O4^iv	0.93	2.70	3.528 (5)	149

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