5,5'-Dimeth-oxy-2,2'-[4,5-dimethyl-o-phenyl-enebis(nitrilo-methyl-idyne)]diphenol.

In the crystal structure of the title compound, C(24)H(24)N(2)O(4), the dihedral angles between the central and the two outer benzene rings are 48.12 (8) and 21.44 (8)°. Intra-molecular O-H⋯N hydrogen bonding generates S(6) rings.

Related literature

For graph-set notation see: Bernstein et al. (1995 ▶). For a related structure see: Kargar et al. (2010 ▶).

Experimental

Crystal data

C24H24N2O4

M = 404.45

Monoclinic,

a = 6.6720 (3) Å

b = 14.3192 (6) Å

c = 21.7396 (9) Å

β = 95.177 (2)°

V = 2068.48 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.42 × 0.32 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.964, T max = 0.984

23605 measured reflections

5123 independent reflections

3112 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.125

S = 1.01

5123 reflections

274 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810007282/nc2177sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007282/nc2177Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C24H24N2O4	F(000) = 856
Mr = 404.45	Dx = 1.299 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5431 reflections
a = 6.6720 (3) Å	θ = 2.4–26.4°
b = 14.3192 (6) Å	µ = 0.09 mm−1
c = 21.7396 (9) Å	T = 296 K
β = 95.177 (2)°	Block, yellow
V = 2068.48 (15) Å3	0.42 × 0.32 × 0.18 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	5123 independent reflections
Radiation source: fine-focus sealed tube	3112 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→6
Tmin = 0.964, Tmax = 0.984	k = −19→13
23605 measured reflections	l = −28→28

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0473P)2 + 0.4824P] where P = (Fo2 + 2Fc2)/3
5123 reflections	(Δ/σ)max = 0.001
274 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
O1	0.80563 (17)	1.05843 (9)	0.32895 (6)	0.0605 (4)
H1	0.8156	1.0315	0.2894	0.091*
O2	0.61776 (18)	0.82964 (9)	0.31447 (5)	0.0601 (4)
H2	0.6865	0.8448	0.2791	0.090*
O3	1.2169 (2)	1.11971 (10)	0.51656 (6)	0.0720 (4)
O4	0.03885 (19)	0.66990 (9)	0.35951 (6)	0.0634 (4)
N1	0.9786 (2)	0.97538 (9)	0.24052 (6)	0.0424 (3)
N2	0.6943 (2)	0.84762 (9)	0.20089 (6)	0.0437 (3)
C1	0.9858 (2)	1.05519 (11)	0.36245 (7)	0.0423 (4)
C2	1.0013 (3)	1.09115 (12)	0.42227 (8)	0.0500 (4)
H2A	0.8890	1.1163	0.4386	0.060*
C3	1.1851 (3)	1.08903 (12)	0.45710 (8)	0.0517 (4)
C4	1.3543 (3)	1.05316 (14)	0.43257 (8)	0.0579 (5)
H4A	1.4783	1.0535	0.4558	0.070*
C5	1.3372 (3)	1.01751 (13)	0.37431 (8)	0.0516 (4)
H5A	1.4507	0.9926	0.3585	0.062*
C6	1.1544 (2)	1.01719 (11)	0.33750 (7)	0.0406 (4)
C7	1.1429 (2)	0.98008 (11)	0.27563 (7)	0.0423 (4)
H7A	1.2605	0.9585	0.2605	0.051*
C8	0.9810 (2)	0.93897 (11)	0.18012 (7)	0.0405 (4)
C9	1.1249 (2)	0.96510 (12)	0.14096 (7)	0.0469 (4)
H9A	1.2213	1.0091	0.1546	0.056*
C10	1.1297 (3)	0.92783 (13)	0.08221 (7)	0.0500 (4)
C11	0.9840 (3)	0.86310 (13)	0.06121 (8)	0.0513 (4)
C12	0.8381 (3)	0.83831 (12)	0.09976 (8)	0.0499 (4)
H12A	0.7403	0.7952	0.0856	0.060*
C13	0.8323 (2)	0.87538 (11)	0.15879 (7)	0.0411 (4)
C14	0.5294 (2)	0.80505 (11)	0.18428 (7)	0.0437 (4)
H14A	0.4933	0.7952	0.1425	0.052*
C15	0.3988 (2)	0.77214 (11)	0.22869 (7)	0.0396 (4)
C16	0.2190 (2)	0.72666 (12)	0.20999 (8)	0.0468 (4)
H16A	0.1827	0.7193	0.1680	0.056*
C17	0.0929 (3)	0.69218 (12)	0.25145 (8)	0.0498 (4)
H17A	−0.0263	0.6620	0.2377	0.060*
C18	0.1477 (3)	0.70345 (11)	0.31392 (8)	0.0468 (4)
C19	0.3228 (3)	0.75016 (12)	0.33444 (8)	0.0491 (4)
H19A	0.3560	0.7585	0.3766	0.059*
C20	0.4481 (2)	0.78427 (11)	0.29270 (7)	0.0430 (4)
C21	1.0541 (4)	1.15847 (16)	0.54511 (10)	0.0783 (7)
H21A	1.0992	1.1773	0.5864	0.117*
H21B	0.9495	1.1127	0.5463	0.117*
H21C	1.0031	1.2118	0.5220	0.117*
C22	−0.1404 (3)	0.61818 (16)	0.34162 (11)	0.0744 (6)
H22A	−0.2026	0.5996	0.3778	0.112*
H22B	−0.1069	0.5637	0.3189	0.112*
H22C	−0.2319	0.6565	0.3161	0.112*
C23	1.2948 (3)	0.95713 (16)	0.04274 (9)	0.0708 (6)
H23A	1.2358	0.9807	0.0039	0.106*
H23B	1.3781	0.9042	0.0356	0.106*
H23C	1.3753	1.0050	0.0637	0.106*
C24	0.9800 (3)	0.81878 (17)	−0.00213 (9)	0.0763 (6)
H24A	0.8676	0.7769	−0.0081	0.114*
H24B	1.1026	0.7847	−0.0053	0.114*
H24C	0.9673	0.8666	−0.0332	0.114*

	U11	U22	U33	U12	U13	U23
O1	0.0412 (7)	0.0832 (9)	0.0572 (8)	0.0083 (6)	0.0045 (6)	−0.0120 (6)
O2	0.0573 (8)	0.0784 (9)	0.0436 (7)	−0.0228 (7)	−0.0005 (6)	−0.0057 (6)
O3	0.0826 (10)	0.0852 (10)	0.0475 (7)	−0.0034 (8)	0.0031 (7)	−0.0143 (7)
O4	0.0621 (8)	0.0663 (8)	0.0646 (8)	−0.0111 (7)	0.0203 (7)	0.0011 (6)
N1	0.0423 (8)	0.0461 (8)	0.0390 (7)	−0.0018 (6)	0.0049 (6)	−0.0045 (6)
N2	0.0458 (8)	0.0452 (8)	0.0405 (7)	−0.0030 (6)	0.0063 (6)	−0.0035 (6)
C1	0.0393 (9)	0.0436 (9)	0.0439 (9)	−0.0004 (7)	0.0037 (7)	0.0004 (7)
C2	0.0556 (11)	0.0462 (9)	0.0501 (10)	0.0032 (8)	0.0155 (8)	−0.0041 (8)
C3	0.0633 (12)	0.0514 (10)	0.0398 (9)	−0.0063 (9)	0.0019 (8)	−0.0017 (8)
C4	0.0498 (11)	0.0734 (13)	0.0491 (10)	−0.0007 (9)	−0.0045 (8)	0.0008 (9)
C5	0.0442 (10)	0.0628 (11)	0.0480 (10)	0.0038 (8)	0.0046 (8)	0.0017 (8)
C6	0.0402 (9)	0.0414 (8)	0.0402 (8)	−0.0005 (7)	0.0049 (7)	0.0012 (7)
C7	0.0444 (10)	0.0406 (8)	0.0430 (9)	0.0029 (7)	0.0099 (7)	0.0004 (7)
C8	0.0436 (9)	0.0404 (8)	0.0377 (8)	0.0042 (7)	0.0053 (7)	−0.0011 (7)
C9	0.0463 (10)	0.0485 (10)	0.0463 (9)	−0.0020 (8)	0.0059 (7)	0.0018 (7)
C10	0.0526 (11)	0.0570 (11)	0.0417 (9)	0.0081 (8)	0.0122 (8)	0.0058 (8)
C11	0.0570 (11)	0.0579 (11)	0.0398 (9)	0.0073 (9)	0.0076 (8)	−0.0031 (8)
C12	0.0525 (11)	0.0515 (10)	0.0456 (10)	−0.0012 (8)	0.0044 (8)	−0.0080 (8)
C13	0.0436 (9)	0.0419 (8)	0.0381 (8)	0.0035 (7)	0.0055 (7)	−0.0005 (7)
C14	0.0485 (10)	0.0447 (9)	0.0374 (8)	0.0026 (8)	0.0016 (7)	−0.0030 (7)
C15	0.0411 (9)	0.0371 (8)	0.0402 (8)	0.0034 (7)	0.0003 (7)	−0.0027 (6)
C16	0.0473 (10)	0.0490 (9)	0.0431 (9)	0.0009 (8)	−0.0026 (8)	−0.0052 (7)
C17	0.0414 (10)	0.0482 (10)	0.0590 (11)	−0.0040 (8)	0.0007 (8)	−0.0057 (8)
C18	0.0480 (10)	0.0397 (9)	0.0541 (10)	0.0028 (7)	0.0120 (8)	0.0009 (7)
C19	0.0559 (11)	0.0537 (10)	0.0375 (9)	−0.0031 (8)	0.0017 (8)	−0.0001 (7)
C20	0.0429 (9)	0.0421 (9)	0.0432 (9)	−0.0017 (7)	−0.0009 (7)	−0.0033 (7)
C21	0.1081 (18)	0.0731 (14)	0.0560 (12)	0.0039 (13)	0.0201 (12)	−0.0142 (10)
C22	0.0542 (12)	0.0735 (14)	0.0982 (17)	−0.0124 (10)	0.0209 (11)	0.0092 (12)
C23	0.0717 (14)	0.0888 (15)	0.0553 (11)	−0.0013 (12)	0.0244 (10)	0.0064 (10)
C24	0.0886 (16)	0.0914 (16)	0.0512 (11)	0.0007 (13)	0.0195 (11)	−0.0204 (11)

O1—C1	1.3489 (19)	C10—C23	1.515 (2)
O1—H1	0.9496	C11—C12	1.387 (2)
O2—C20	1.3532 (19)	C11—C24	1.514 (2)
O2—H2	0.9553	C12—C13	1.392 (2)
O3—C3	1.364 (2)	C12—H12A	0.9300
O3—C21	1.412 (2)	C14—C15	1.437 (2)
O4—C18	1.3678 (19)	C14—H14A	0.9300
O4—C22	1.430 (2)	C15—C16	1.393 (2)
N1—C7	1.2798 (19)	C15—C20	1.411 (2)
N1—C8	1.4142 (19)	C16—C17	1.379 (2)
N2—C14	1.281 (2)	C16—H16A	0.9300
N2—C13	1.412 (2)	C17—C18	1.384 (2)
C1—C2	1.394 (2)	C17—H17A	0.9300
C1—C6	1.402 (2)	C18—C19	1.385 (2)
C2—C3	1.383 (2)	C19—C20	1.377 (2)
C2—H2A	0.9300	C19—H19A	0.9300
C3—C4	1.389 (3)	C21—H21A	0.9600
C4—C5	1.361 (2)	C21—H21B	0.9600
C4—H4A	0.9300	C21—H21C	0.9600
C5—C6	1.397 (2)	C22—H22A	0.9600
C5—H5A	0.9300	C22—H22B	0.9600
C6—C7	1.442 (2)	C22—H22C	0.9600
C7—H7A	0.9300	C23—H23A	0.9600
C8—C9	1.391 (2)	C23—H23B	0.9600
C8—C13	1.395 (2)	C23—H23C	0.9600
C9—C10	1.387 (2)	C24—H24A	0.9600
C9—H9A	0.9300	C24—H24B	0.9600
C10—C11	1.390 (2)	C24—H24C	0.9600
C1—O1—H1	110.0	N2—C14—C15	121.61 (15)
C20—O2—H2	106.0	N2—C14—H14A	119.2
C3—O3—C21	118.90 (16)	C15—C14—H14A	119.2
C18—O4—C22	118.07 (15)	C16—C15—C20	117.59 (15)
C7—N1—C8	119.49 (13)	C16—C15—C14	121.04 (15)
C14—N2—C13	123.01 (14)	C20—C15—C14	121.37 (15)
O1—C1—C2	118.58 (14)	C17—C16—C15	122.47 (16)
O1—C1—C6	120.76 (14)	C17—C16—H16A	118.8
C2—C1—C6	120.65 (15)	C15—C16—H16A	118.8
C3—C2—C1	119.35 (16)	C16—C17—C18	118.49 (16)
C3—C2—H2A	120.3	C16—C17—H17A	120.8
C1—C2—H2A	120.3	C18—C17—H17A	120.8
O3—C3—C2	124.51 (17)	O4—C18—C17	124.02 (16)
O3—C3—C4	114.88 (17)	O4—C18—C19	115.09 (15)
C2—C3—C4	120.61 (16)	C17—C18—C19	120.88 (15)
C5—C4—C3	119.56 (17)	C20—C19—C18	120.23 (15)
C5—C4—H4A	120.2	C20—C19—H19A	119.9
C3—C4—H4A	120.2	C18—C19—H19A	119.9
C4—C5—C6	121.98 (16)	O2—C20—C19	118.56 (15)
C4—C5—H5A	119.0	O2—C20—C15	121.14 (14)
C6—C5—H5A	119.0	C19—C20—C15	120.31 (15)
C5—C6—C1	117.82 (14)	O3—C21—H21A	109.5
C5—C6—C7	120.37 (15)	O3—C21—H21B	109.5
C1—C6—C7	121.80 (14)	H21A—C21—H21B	109.5
N1—C7—C6	123.11 (14)	O3—C21—H21C	109.5
N1—C7—H7A	118.4	H21A—C21—H21C	109.5
C6—C7—H7A	118.4	H21B—C21—H21C	109.5
C9—C8—C13	118.80 (14)	O4—C22—H22A	109.5
C9—C8—N1	122.38 (15)	O4—C22—H22B	109.5
C13—C8—N1	118.81 (13)	H22A—C22—H22B	109.5
C10—C9—C8	122.33 (16)	O4—C22—H22C	109.5
C10—C9—H9A	118.8	H22A—C22—H22C	109.5
C8—C9—H9A	118.8	H22B—C22—H22C	109.5
C9—C10—C11	119.02 (15)	C10—C23—H23A	109.5
C9—C10—C23	119.55 (17)	C10—C23—H23B	109.5
C11—C10—C23	121.43 (16)	H23A—C23—H23B	109.5
C12—C11—C10	118.72 (15)	C10—C23—H23C	109.5
C12—C11—C24	119.12 (17)	H23A—C23—H23C	109.5
C10—C11—C24	122.16 (16)	H23B—C23—H23C	109.5
C11—C12—C13	122.60 (16)	C11—C24—H24A	109.5
C11—C12—H12A	118.7	C11—C24—H24B	109.5
C13—C12—H12A	118.7	H24A—C24—H24B	109.5
C12—C13—C8	118.50 (14)	C11—C24—H24C	109.5
C12—C13—N2	124.33 (15)	H24A—C24—H24C	109.5
C8—C13—N2	116.99 (13)	H24B—C24—H24C	109.5
O1—C1—C2—C3	−179.53 (15)	C10—C11—C12—C13	−0.3 (3)
C6—C1—C2—C3	−0.1 (2)	C24—C11—C12—C13	179.54 (17)
C21—O3—C3—C2	−1.4 (3)	C11—C12—C13—C8	−0.9 (3)
C21—O3—C3—C4	179.18 (18)	C11—C12—C13—N2	−175.78 (16)
C1—C2—C3—O3	−178.09 (16)	C9—C8—C13—C12	2.1 (2)
C1—C2—C3—C4	1.3 (3)	N1—C8—C13—C12	−178.65 (15)
O3—C3—C4—C5	177.60 (17)	C9—C8—C13—N2	177.33 (14)
C2—C3—C4—C5	−1.8 (3)	N1—C8—C13—N2	−3.4 (2)
C3—C4—C5—C6	1.2 (3)	C14—N2—C13—C12	−19.3 (2)
C4—C5—C6—C1	0.0 (3)	C14—N2—C13—C8	165.74 (15)
C4—C5—C6—C7	179.05 (17)	C13—N2—C14—C15	175.71 (14)
O1—C1—C6—C5	178.89 (15)	N2—C14—C15—C16	179.45 (15)
C2—C1—C6—C5	−0.6 (2)	N2—C14—C15—C20	−0.8 (2)
O1—C1—C6—C7	−0.1 (2)	C20—C15—C16—C17	−1.4 (2)
C2—C1—C6—C7	−179.59 (15)	C14—C15—C16—C17	178.33 (15)
C8—N1—C7—C6	179.24 (14)	C15—C16—C17—C18	0.0 (3)
C5—C6—C7—N1	177.82 (15)	C22—O4—C18—C17	1.5 (2)
C1—C6—C7—N1	−3.2 (2)	C22—O4—C18—C19	−177.94 (16)
C7—N1—C8—C9	−45.6 (2)	C16—C17—C18—O4	−177.89 (15)
C7—N1—C8—C13	135.15 (16)	C16—C17—C18—C19	1.5 (3)
C13—C8—C9—C10	−2.2 (2)	O4—C18—C19—C20	177.83 (15)
N1—C8—C9—C10	178.57 (15)	C17—C18—C19—C20	−1.6 (3)
C8—C9—C10—C11	1.0 (3)	C18—C19—C20—O2	179.93 (15)
C8—C9—C10—C23	−178.04 (16)	C18—C19—C20—C15	0.2 (2)
C9—C10—C11—C12	0.2 (3)	C16—C15—C20—O2	−178.47 (14)
C23—C10—C11—C12	179.28 (17)	C14—C15—C20—O2	1.8 (2)
C9—C10—C11—C24	−179.56 (18)	C16—C15—C20—C19	1.3 (2)
C23—C10—C11—C24	−0.5 (3)	C14—C15—C20—C19	−178.46 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.95	1.78	2.6158 (18)	145
O2—H2···N2	0.96	1.71	2.5791 (17)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.95	1.78	2.6158 (18)	145
O2—H2⋯N2	0.96	1.71	2.5791 (17)	150