(2E,2'E)-Dimethyl 2,2'-[(phenyl-aza-nedi-yl)bis-(methyl-ene)]bis-(3-phenyl-acrylate).

The C=C double bonds in the title compound, C(28)H(27)NO(4), adopt an E conformation. In the crystal, pairs of C-H⋯O hydrogen bonds link the mol-ecules into inversion dimers.

Related literature

For applications of acrylate derivatives, see: De Fraine & Martin (1991 ▶). For resonance effects of the acrylate moiety, see: Merlino (1971 ▶); Varghese et al. (1986 ▶).

Experimental

Crystal data

C28H27NO4

M = 441.51

Triclinic,

a = 9.9099 (2) Å

b = 11.7327 (2) Å

c = 12.4079 (4) Å

α = 101.131 (2)°

β = 106.039 (2)°

γ = 114.817 (1)°

V = 1176.86 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.32 × 0.20 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.972, T max = 0.992

15565 measured reflections

5710 independent reflections

3683 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.127

S = 1.03

5710 reflections

300 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812029042/bt5946sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029042/bt5946Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029042/bt5946Isup3.cml

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

C28H27NO4	Z = 2
Mr = 441.51	F(000) = 468
Triclinic, P1	Dx = 1.246 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9099 (2) Å	Cell parameters from 5710 reflections
b = 11.7327 (2) Å	θ = 1.8–28.5°
c = 12.4079 (4) Å	µ = 0.08 mm−1
α = 101.131 (2)°	T = 298 K
β = 106.039 (2)°	Triclinic, colourless
γ = 114.817 (1)°	0.32 × 0.20 × 0.10 mm
V = 1176.86 (5) Å3

Bruker APEXII CCD area-detector diffractometer	5710 independent reflections
Radiation source: fine-focus sealed tube	3683 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω and φ scans	θmax = 28.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→13
Tmin = 0.972, Tmax = 0.992	k = −15→15
15565 measured reflections	l = −16→16

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0521P)2 + 0.1829P] where P = (Fo2 + 2Fc2)/3
5710 reflections	(Δ/σ)max < 0.001
300 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.41831 (18)	−0.27590 (16)	0.18680 (14)	0.0505 (4)
H1	0.3986	−0.2081	0.1731	0.061*
C2	0.3444 (2)	−0.34918 (18)	0.24884 (16)	0.0624 (5)
H2	0.2763	−0.3297	0.2775	0.075*
C3	0.3709 (2)	−0.4505 (2)	0.26837 (17)	0.0694 (5)
H3	0.3219	−0.4987	0.3111	0.083*
C4	0.4697 (2)	−0.48088 (19)	0.22485 (17)	0.0664 (5)
H4	0.4866	−0.5503	0.2373	0.080*
C5	0.54353 (19)	−0.40857 (16)	0.16293 (15)	0.0525 (4)
H5	0.6089	−0.4307	0.1327	0.063*
C6	0.52232 (17)	−0.30277 (14)	0.14460 (13)	0.0418 (3)
C7	0.60328 (17)	−0.23200 (14)	0.07556 (12)	0.0427 (3)
H7	0.6177	−0.2840	0.0180	0.051*
C8	0.65925 (17)	−0.10413 (14)	0.08314 (12)	0.0402 (3)
C9	0.65417 (17)	0.00032 (14)	0.17295 (13)	0.0427 (3)
H9A	0.5591	0.0062	0.1343	0.051*
H9B	0.6412	−0.0304	0.2385	0.051*
C10	0.93968 (17)	0.16227 (14)	0.30881 (12)	0.0365 (3)
C11	0.9588 (2)	0.06137 (16)	0.34304 (13)	0.0476 (4)
H11	0.8730	−0.0267	0.3075	0.057*
C12	1.1034 (2)	0.09086 (19)	0.42885 (14)	0.0598 (5)
H12	1.1132	0.0222	0.4504	0.072*
C13	1.2329 (2)	0.21927 (19)	0.48300 (15)	0.0627 (5)
H13	1.3297	0.2382	0.5409	0.075*
C14	1.2162 (2)	0.31928 (17)	0.44981 (15)	0.0557 (4)
H14	1.3035	0.4067	0.4855	0.067*
C15	1.07327 (17)	0.29301 (14)	0.36500 (13)	0.0435 (3)
H15	1.0652	0.3629	0.3447	0.052*
C16	0.77545 (19)	0.24172 (14)	0.19443 (13)	0.0424 (3)
H16A	0.6728	0.2021	0.1264	0.051*
H16B	0.8608	0.2908	0.1699	0.051*
C17	0.77845 (18)	0.34132 (15)	0.29512 (13)	0.0426 (3)
C18	0.83568 (18)	0.47221 (15)	0.31417 (13)	0.0460 (4)
H18	0.8367	0.5199	0.3839	0.055*
C19	0.89688 (18)	0.55354 (15)	0.24480 (13)	0.0440 (3)
C20	0.8597 (2)	0.50340 (16)	0.12296 (14)	0.0512 (4)
H20	0.7963	0.4112	0.0815	0.061*
C21	0.9149 (2)	0.58743 (18)	0.06251 (16)	0.0619 (5)
H21	0.8882	0.5517	−0.0191	0.074*
C22	1.0091 (3)	0.72337 (19)	0.12183 (18)	0.0707 (5)
H22	1.0481	0.7799	0.0812	0.085*
C23	1.0455 (3)	0.77566 (18)	0.24174 (19)	0.0718 (5)
H23	1.1089	0.8680	0.2822	0.086*
C24	0.9889 (2)	0.69226 (16)	0.30240 (16)	0.0582 (4)
H24	1.0124	0.7292	0.3832	0.070*
C25	0.72072 (18)	−0.06039 (16)	−0.00643 (14)	0.0468 (4)
C26	0.8187 (3)	−0.1112 (2)	−0.15181 (19)	0.0900 (7)
H26A	0.7303	−0.1187	−0.2152	0.135*
H26B	0.8486	−0.1746	−0.1821	0.135*
H26C	0.9099	−0.0219	−0.1217	0.135*
C27	0.7138 (2)	0.29464 (17)	0.38288 (15)	0.0530 (4)
C28	0.5352 (3)	0.1088 (2)	0.4154 (2)	0.0999 (8)
H28A	0.6222	0.1220	0.4839	0.150*
H28B	0.4601	0.0144	0.3739	0.150*
H28C	0.4801	0.1518	0.4414	0.150*
N1	0.79578 (14)	0.13407 (11)	0.22255 (10)	0.0407 (3)
O1	0.72348 (16)	0.03324 (13)	−0.03387 (11)	0.0649 (3)
O2	0.76968 (17)	−0.13876 (12)	−0.05645 (11)	0.0697 (4)
O3	0.7549 (2)	0.36236 (14)	0.48407 (12)	0.0899 (5)
O4	0.59991 (17)	0.16605 (12)	0.33627 (12)	0.0769 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0439 (8)	0.0400 (9)	0.0580 (10)	0.0154 (7)	0.0226 (8)	0.0087 (7)
C2	0.0484 (10)	0.0593 (12)	0.0636 (11)	0.0140 (9)	0.0287 (9)	0.0121 (9)
C3	0.0591 (11)	0.0653 (13)	0.0618 (11)	0.0110 (10)	0.0231 (10)	0.0281 (10)
C4	0.0644 (11)	0.0522 (11)	0.0699 (12)	0.0216 (10)	0.0174 (10)	0.0285 (10)
C5	0.0503 (9)	0.0434 (9)	0.0567 (10)	0.0222 (8)	0.0173 (8)	0.0130 (8)
C6	0.0388 (7)	0.0313 (8)	0.0409 (8)	0.0108 (6)	0.0131 (6)	0.0043 (6)
C7	0.0441 (8)	0.0353 (8)	0.0431 (8)	0.0181 (7)	0.0189 (7)	0.0046 (6)
C8	0.0384 (7)	0.0345 (8)	0.0407 (8)	0.0155 (7)	0.0157 (6)	0.0059 (6)
C9	0.0419 (8)	0.0320 (8)	0.0491 (8)	0.0155 (7)	0.0210 (7)	0.0076 (6)
C10	0.0439 (8)	0.0350 (8)	0.0350 (7)	0.0203 (7)	0.0225 (6)	0.0104 (6)
C11	0.0599 (10)	0.0387 (9)	0.0416 (8)	0.0237 (8)	0.0199 (8)	0.0123 (7)
C12	0.0810 (13)	0.0633 (12)	0.0442 (9)	0.0476 (11)	0.0199 (9)	0.0178 (9)
C13	0.0589 (11)	0.0724 (13)	0.0460 (9)	0.0387 (11)	0.0090 (8)	0.0040 (9)
C14	0.0464 (9)	0.0506 (10)	0.0548 (10)	0.0209 (8)	0.0175 (8)	0.0002 (8)
C15	0.0447 (8)	0.0366 (8)	0.0483 (8)	0.0190 (7)	0.0235 (7)	0.0097 (7)
C16	0.0516 (9)	0.0354 (8)	0.0420 (8)	0.0242 (7)	0.0194 (7)	0.0110 (6)
C17	0.0477 (8)	0.0388 (8)	0.0447 (8)	0.0252 (7)	0.0198 (7)	0.0110 (7)
C18	0.0547 (9)	0.0427 (9)	0.0458 (8)	0.0298 (8)	0.0226 (7)	0.0099 (7)
C19	0.0500 (8)	0.0371 (8)	0.0503 (9)	0.0279 (7)	0.0197 (7)	0.0124 (7)
C20	0.0635 (10)	0.0406 (9)	0.0483 (9)	0.0297 (8)	0.0166 (8)	0.0136 (7)
C21	0.0878 (13)	0.0560 (11)	0.0545 (10)	0.0443 (11)	0.0290 (10)	0.0243 (9)
C22	0.0986 (15)	0.0569 (12)	0.0821 (14)	0.0463 (12)	0.0493 (12)	0.0386 (11)
C23	0.0914 (14)	0.0364 (10)	0.0839 (14)	0.0281 (10)	0.0388 (12)	0.0177 (10)
C24	0.0734 (12)	0.0406 (9)	0.0602 (10)	0.0299 (9)	0.0293 (9)	0.0104 (8)
C25	0.0473 (9)	0.0390 (9)	0.0464 (8)	0.0175 (7)	0.0198 (7)	0.0081 (7)
C26	0.1282 (19)	0.0856 (16)	0.0804 (14)	0.0509 (15)	0.0781 (15)	0.0305 (12)
C27	0.0664 (11)	0.0444 (10)	0.0567 (10)	0.0303 (9)	0.0339 (9)	0.0156 (8)
C28	0.1206 (19)	0.0731 (15)	0.1195 (19)	0.0308 (14)	0.0928 (17)	0.0376 (14)
N1	0.0428 (7)	0.0290 (6)	0.0458 (7)	0.0167 (6)	0.0161 (6)	0.0100 (5)
O1	0.0853 (9)	0.0595 (8)	0.0673 (8)	0.0399 (7)	0.0417 (7)	0.0318 (7)
O2	0.1020 (10)	0.0596 (8)	0.0761 (8)	0.0452 (8)	0.0650 (8)	0.0272 (7)
O3	0.1303 (13)	0.0634 (9)	0.0627 (8)	0.0304 (9)	0.0559 (9)	0.0136 (7)
O4	0.0862 (9)	0.0504 (8)	0.0820 (9)	0.0144 (7)	0.0586 (8)	0.0099 (7)

C1—C2	1.381 (2)	C16—N1	1.4499 (17)
C1—C6	1.394 (2)	C16—C17	1.5211 (19)
C1—H1	0.9300	C16—H16A	0.9700
C2—C3	1.370 (3)	C16—H16B	0.9700
C2—H2	0.9300	C17—C18	1.338 (2)
C3—C4	1.375 (3)	C17—C27	1.489 (2)
C3—H3	0.9300	C18—C19	1.462 (2)
C4—C5	1.373 (2)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.391 (2)
C5—C6	1.392 (2)	C19—C24	1.391 (2)
C5—H5	0.9300	C20—C21	1.376 (2)
C6—C7	1.4704 (19)	C20—H20	0.9300
C7—C8	1.3362 (19)	C21—C22	1.369 (3)
C7—H7	0.9300	C21—H21	0.9300
C8—C25	1.484 (2)	C22—C23	1.373 (3)
C8—C9	1.5172 (19)	C22—H22	0.9300
C9—N1	1.4533 (18)	C23—C24	1.377 (2)
C9—H9A	0.9700	C23—H23	0.9300
C9—H9B	0.9700	C24—H24	0.9300
C10—N1	1.3830 (18)	C25—O1	1.2032 (18)
C10—C11	1.3985 (19)	C25—O2	1.3367 (18)
C10—C15	1.401 (2)	C26—O2	1.440 (2)
C11—C12	1.380 (2)	C26—H26A	0.9600
C11—H11	0.9300	C26—H26B	0.9600
C12—C13	1.370 (3)	C26—H26C	0.9600
C12—H12	0.9300	C27—O3	1.1976 (19)
C13—C14	1.373 (2)	C27—O4	1.326 (2)
C13—H13	0.9300	C28—O4	1.438 (2)
C14—C15	1.376 (2)	C28—H28A	0.9600
C14—H14	0.9300	C28—H28B	0.9600
C15—H15	0.9300	C28—H28C	0.9600
C2—C1—C6	120.52 (15)	N1—C16—H16B	108.3
C2—C1—H1	119.7	C17—C16—H16B	108.3
C6—C1—H1	119.7	H16A—C16—H16B	107.4
C3—C2—C1	120.32 (16)	C18—C17—C27	114.62 (13)
C3—C2—H2	119.8	C18—C17—C16	125.71 (13)
C1—C2—H2	119.8	C27—C17—C16	119.67 (13)
C2—C3—C4	120.09 (16)	C17—C18—C19	131.42 (13)
C2—C3—H3	120.0	C17—C18—H18	114.3
C4—C3—H3	120.0	C19—C18—H18	114.3
C5—C4—C3	119.93 (17)	C20—C19—C24	117.28 (15)
C5—C4—H4	120.0	C20—C19—C18	124.78 (14)
C3—C4—H4	120.0	C24—C19—C18	117.74 (14)
C4—C5—C6	121.21 (16)	C21—C20—C19	121.32 (15)
C4—C5—H5	119.4	C21—C20—H20	119.3
C6—C5—H5	119.4	C19—C20—H20	119.3
C5—C6—C1	117.88 (14)	C22—C21—C20	120.34 (16)
C5—C6—C7	117.79 (13)	C22—C21—H21	119.8
C1—C6—C7	124.22 (13)	C20—C21—H21	119.8
C8—C7—C6	129.70 (12)	C21—C22—C23	119.52 (17)
C8—C7—H7	115.1	C21—C22—H22	120.2
C6—C7—H7	115.1	C23—C22—H22	120.2
C7—C8—C25	119.20 (12)	C22—C23—C24	120.42 (17)
C7—C8—C9	124.47 (12)	C22—C23—H23	119.8
C25—C8—C9	116.18 (12)	C24—C23—H23	119.8
N1—C9—C8	115.32 (11)	C23—C24—C19	121.07 (16)
N1—C9—H9A	108.4	C23—C24—H24	119.5
C8—C9—H9A	108.4	C19—C24—H24	119.5
N1—C9—H9B	108.4	O1—C25—O2	123.05 (14)
C8—C9—H9B	108.4	O1—C25—C8	124.34 (13)
H9A—C9—H9B	107.5	O2—C25—C8	112.58 (13)
N1—C10—C11	121.47 (13)	O2—C26—H26A	109.5
N1—C10—C15	121.47 (12)	O2—C26—H26B	109.5
C11—C10—C15	117.06 (13)	H26A—C26—H26B	109.5
C12—C11—C10	120.84 (15)	O2—C26—H26C	109.5
C12—C11—H11	119.6	H26A—C26—H26C	109.5
C10—C11—H11	119.6	H26B—C26—H26C	109.5
C13—C12—C11	121.37 (16)	O3—C27—O4	121.91 (15)
C13—C12—H12	119.3	O3—C27—C17	125.83 (16)
C11—C12—H12	119.3	O4—C27—C17	112.25 (13)
C12—C13—C14	118.45 (16)	O4—C28—H28A	109.5
C12—C13—H13	120.8	O4—C28—H28B	109.5
C14—C13—H13	120.8	H28A—C28—H28B	109.5
C13—C14—C15	121.48 (16)	O4—C28—H28C	109.5
C13—C14—H14	119.3	H28A—C28—H28C	109.5
C15—C14—H14	119.3	H28B—C28—H28C	109.5
C14—C15—C10	120.80 (14)	C10—N1—C16	120.33 (11)
C14—C15—H15	119.6	C10—N1—C9	120.62 (11)
C10—C15—H15	119.6	C16—N1—C9	118.29 (11)
N1—C16—C17	115.91 (11)	C25—O2—C26	116.69 (14)
N1—C16—H16A	108.3	C27—O4—C28	116.80 (15)
C17—C16—H16A	108.3
C6—C1—C2—C3	−0.8 (3)	C24—C19—C20—C21	1.5 (2)
C1—C2—C3—C4	−0.8 (3)	C18—C19—C20—C21	176.33 (15)
C2—C3—C4—C5	0.8 (3)	C19—C20—C21—C22	0.3 (3)
C3—C4—C5—C6	1.0 (3)	C20—C21—C22—C23	−1.3 (3)
C4—C5—C6—C1	−2.6 (2)	C21—C22—C23—C24	0.4 (3)
C4—C5—C6—C7	−178.95 (15)	C22—C23—C24—C19	1.5 (3)
C2—C1—C6—C5	2.5 (2)	C20—C19—C24—C23	−2.3 (2)
C2—C1—C6—C7	178.59 (15)	C18—C19—C24—C23	−177.57 (16)
C5—C6—C7—C8	−150.06 (16)	C7—C8—C25—O1	154.50 (16)
C1—C6—C7—C8	33.8 (2)	C9—C8—C25—O1	−21.3 (2)
C6—C7—C8—C25	−173.35 (14)	C7—C8—C25—O2	−23.9 (2)
C6—C7—C8—C9	2.1 (2)	C9—C8—C25—O2	160.27 (13)
C7—C8—C9—N1	141.60 (14)	C18—C17—C27—O3	−26.7 (2)
C25—C8—C9—N1	−42.83 (18)	C16—C17—C27—O3	153.25 (18)
N1—C10—C11—C12	179.68 (13)	C18—C17—C27—O4	152.40 (14)
C15—C10—C11—C12	0.3 (2)	C16—C17—C27—O4	−27.7 (2)
C10—C11—C12—C13	−0.2 (2)	C11—C10—N1—C16	175.89 (12)
C11—C12—C13—C14	−0.2 (2)	C15—C10—N1—C16	−4.70 (18)
C12—C13—C14—C15	0.5 (2)	C11—C10—N1—C9	6.04 (18)
C13—C14—C15—C10	−0.5 (2)	C15—C10—N1—C9	−174.56 (12)
N1—C10—C15—C14	−179.34 (12)	C17—C16—N1—C10	−64.45 (17)
C11—C10—C15—C14	0.09 (19)	C17—C16—N1—C9	105.64 (15)
N1—C16—C17—C18	147.18 (15)	C8—C9—N1—C10	−75.60 (16)
N1—C16—C17—C27	−32.7 (2)	C8—C9—N1—C16	114.34 (14)
C27—C17—C18—C19	−174.80 (15)	O1—C25—O2—C26	−3.5 (3)
C16—C17—C18—C19	5.3 (3)	C8—C25—O2—C26	174.95 (16)
C17—C18—C19—C20	22.5 (3)	O3—C27—O4—C28	−4.1 (3)
C17—C18—C19—C24	−162.63 (16)	C17—C27—O4—C28	176.82 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1i	0.97	2.52	3.474 (2)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1i	0.97	2.52	3.474 (2)	167

Symmetry code: (i) .