Crystal structure of 1,1'-{(dodecane-1,12-di-yl)bis-[(aza-niumylyl-idene)methanylyl-idene]}bis-(naphthalen-2-olate).

The title compound, C34H40N2O2, exists in an extended conformation and has crystallographically imposed centrosymmetry. The crystal packing can be described as being composed of parallel layers stacked along [010]. The zwitterionic structure is stabilized by an intra-molecular N-H⋯O hydrogen-bond inter-action.

Related literature

The compound is synthesized using two procedures, the ultrasound and the conventional methods. We found that the ultrasound irradiation method is more convenient and efficient. For conventional synthesis of similar compounds, see: Ouari et al. (2015a ▸); Mohammadi & Rastegari (2012 ▸); Bhowmik et al. (2011 ▸). For ultrasonic synthesis of similar compounds, see: Rayati & Abdolalian (2013 ▸); Khan et al. (2014 ▸); Kanagarajan et al. (2011 ▸). For related crystal structures, see: Ouari et al. (2010 ▸, 2015b ▸); Popović et al. (2001 ▸); Friscic et al. (1998 ▸); Bi et al. (2012 ▸); Temel et al. (2010 ▸). For their applications, see: Köse et al. (2015 ▸); Grivani et al. (2013 ▸); Amin et al. (2010 ▸); Panneerselvam et al. (2009 ▸); Nasr et al. (2009 ▸); Nejo et al. (2009 ▸); Taha et al. (2012 ▸).

Experimental

Crystal data

C34H40N2O2

M = 508.68

Monoclinic,

a = 54.400 (5) Å

b = 4.7465 (4) Å

c = 10.7022 (9) Å

β = 96.318 (2)°

V = 2746.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.50 × 0.14 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▸) T min = 0.682, T max = 0.746

17506 measured reflections

3271 independent reflections

2313 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.125

S = 1.04

3271 reflections

176 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2008 ▸); cell refinement: SAIn class="Chemical">NT (Bruker, 2008 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: SHELXTL (Sheldrick, 2008 ▸); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015007938/mw2131sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015007938/mw2131Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S2056989015007938/mw2131fig1.tif

The title compound with atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radius.

Click here for additional data file.

c . DOI: 10.1107/S2056989015007938/mw2131fig2.tif

Crystal packing of the title compound viewed along the c axis.

CCDC reference: 1032833

Additional supporting information: crystallographic information; 3D view; checkCIF report

C34H40N2O2	F(000) = 1096
Mr = 508.68	Dx = 1.230 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 54.400 (5) Å	Cell parameters from 3931 reflections
b = 4.7465 (4) Å	θ = 3.0–27.8°
c = 10.7022 (9) Å	µ = 0.08 mm−1
β = 96.318 (2)°	T = 173 K
V = 2746.6 (4) Å3	Prism, yellow
Z = 4	0.50 × 0.14 × 0.06 mm

Bruker APEXII CCD diffractometer	3271 independent reflections
Radiation source: sealed tube	2313 reflections with I > 2σ(I)
Triumph monochromator	Rint = 0.036
φ and ω scans	θmax = 27.9°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −70→70
Tmin = 0.682, Tmax = 0.746	k = −6→5
17506 measured reflections	l = −14→14

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)] = 0.048	Hydrogen site location: mixed
wR(F2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0503P)2 + 2.2119P] where P = (Fo2 + 2Fc2)/3
3271 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.24 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.

	x	y	z	Uiso*/Ueq
C1	0.11107 (3)	−0.3639 (3)	1.08101 (14)	0.0273 (3)
C2	0.09446 (3)	−0.5389 (3)	1.14296 (15)	0.0345 (4)
H2	0.1011	−0.6682	1.2056	0.041*
C3	0.06975 (3)	−0.5229 (4)	1.11383 (17)	0.0386 (4)
H3	0.0594	−0.6413	1.1570	0.046*
C4	0.05853 (3)	−0.3340 (4)	1.02027 (16)	0.0329 (4)
C5	0.03264 (3)	−0.3230 (4)	0.99173 (19)	0.0448 (5)
H5	0.0225	−0.4413	1.0362	0.054*
C6	0.02183 (3)	−0.1460 (5)	0.90169 (19)	0.0478 (5)
H6	0.0043	−0.1410	0.8833	0.057*
C7	0.03675 (3)	0.0275 (4)	0.83679 (19)	0.0434 (4)
H7	0.0293	0.1510	0.7737	0.052*
C8	0.06204 (3)	0.0223 (4)	0.86294 (16)	0.0357 (4)
H8	0.0718	0.1428	0.8175	0.043*
C9	0.07384 (3)	−0.1580 (3)	0.95574 (14)	0.0267 (3)
C10	0.10041 (3)	−0.1712 (3)	0.98713 (13)	0.0248 (3)
C11	0.11636 (3)	0.0138 (3)	0.93099 (14)	0.0261 (3)
H11	0.1092	0.1468	0.8714	0.031*
C12	0.15676 (3)	0.2039 (3)	0.90007 (15)	0.0287 (3)
H12A	0.1668	0.3092	0.9673	0.034*
H12B	0.1468	0.3419	0.8467	0.034*
C13	0.17384 (3)	0.0464 (3)	0.82076 (15)	0.0280 (3)
H13A	0.1638	−0.0594	0.7537	0.034*
H13B	0.1838	−0.0912	0.8743	0.034*
C14	0.19108 (3)	0.2470 (3)	0.76130 (15)	0.0284 (3)
H14A	0.2013	0.3492	0.8288	0.034*
H14B	0.1810	0.3879	0.7102	0.034*
C15	0.20806 (3)	0.0982 (3)	0.67812 (14)	0.0282 (3)
H15A	0.2186	−0.0370	0.7301	0.034*
H15B	0.1978	−0.0108	0.6129	0.034*
C16	0.22456 (3)	0.2977 (3)	0.61412 (14)	0.0289 (3)
H16A	0.2346	0.4090	0.6793	0.035*
H16B	0.2140	0.4308	0.5611	0.035*
C17	0.24187 (3)	0.1500 (3)	0.53257 (14)	0.0292 (3)
H17A	0.2526	0.0186	0.5858	0.035*
H17B	0.2319	0.0369	0.4680	0.035*
N1	0.14027 (2)	0.0119 (3)	0.95644 (12)	0.0288 (3)
O1	0.13443 (2)	−0.3838 (3)	1.11158 (11)	0.0359 (3)
H1N	0.1458 (4)	−0.130 (5)	1.014 (2)	0.065 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0341 (8)	0.0276 (7)	0.0212 (7)	−0.0011 (6)	0.0076 (6)	−0.0064 (6)
C2	0.0435 (10)	0.0325 (8)	0.0281 (8)	−0.0035 (7)	0.0066 (7)	0.0023 (7)
C3	0.0423 (10)	0.0389 (9)	0.0367 (9)	−0.0129 (8)	0.0131 (8)	0.0029 (8)
C4	0.0314 (8)	0.0353 (9)	0.0335 (9)	−0.0074 (7)	0.0105 (7)	−0.0075 (7)
C5	0.0312 (9)	0.0536 (11)	0.0510 (12)	−0.0139 (8)	0.0115 (8)	−0.0061 (9)
C6	0.0245 (9)	0.0620 (13)	0.0568 (12)	−0.0024 (8)	0.0033 (8)	−0.0112 (10)
C7	0.0336 (9)	0.0506 (11)	0.0449 (11)	0.0052 (8)	−0.0008 (8)	−0.0043 (9)
C8	0.0300 (9)	0.0396 (9)	0.0377 (9)	−0.0007 (7)	0.0048 (7)	0.0002 (7)
C9	0.0273 (8)	0.0277 (8)	0.0262 (7)	−0.0021 (6)	0.0075 (6)	−0.0076 (6)
C10	0.0271 (8)	0.0262 (7)	0.0221 (7)	−0.0016 (6)	0.0077 (6)	−0.0050 (6)
C11	0.0281 (8)	0.0282 (7)	0.0231 (7)	0.0020 (6)	0.0073 (6)	−0.0030 (6)
C12	0.0267 (8)	0.0326 (8)	0.0286 (8)	−0.0028 (6)	0.0107 (6)	−0.0011 (6)
C13	0.0259 (8)	0.0324 (8)	0.0271 (8)	0.0001 (6)	0.0097 (6)	−0.0008 (6)
C14	0.0233 (7)	0.0346 (8)	0.0286 (8)	0.0003 (6)	0.0087 (6)	−0.0003 (6)
C15	0.0265 (7)	0.0341 (8)	0.0253 (8)	0.0002 (6)	0.0092 (6)	−0.0001 (6)
C16	0.0256 (8)	0.0366 (8)	0.0259 (8)	0.0003 (6)	0.0093 (6)	−0.0023 (6)
C17	0.0270 (8)	0.0354 (8)	0.0267 (8)	0.0002 (6)	0.0096 (6)	−0.0008 (6)
N1	0.0259 (7)	0.0345 (7)	0.0275 (7)	−0.0004 (6)	0.0096 (5)	0.0016 (6)
O1	0.0323 (6)	0.0435 (7)	0.0317 (6)	0.0024 (5)	0.0026 (5)	0.0042 (5)

C1—O1	1.2802 (19)	C12—N1	1.4553 (19)
C1—C10	1.433 (2)	C12—C13	1.522 (2)
C1—C2	1.442 (2)	C12—H12A	0.9900
C2—C3	1.348 (2)	C12—H12B	0.9900
C2—H2	0.9500	C13—C14	1.524 (2)
C3—C4	1.430 (2)	C13—H13A	0.9900
C3—H3	0.9500	C13—H13B	0.9900
C4—C5	1.409 (2)	C14—C15	1.525 (2)
C4—C9	1.413 (2)	C14—H14A	0.9900
C5—C6	1.362 (3)	C14—H14B	0.9900
C5—H5	0.9500	C15—C16	1.518 (2)
C6—C7	1.394 (3)	C15—H15A	0.9900
C6—H6	0.9500	C15—H15B	0.9900
C7—C8	1.374 (2)	C16—C17	1.5232 (19)
C7—H7	0.9500	C16—H16A	0.9900
C8—C9	1.411 (2)	C16—H16B	0.9900
C8—H8	0.9500	C17—C17i	1.518 (3)
C9—C10	1.449 (2)	C17—H17A	0.9900
C10—C11	1.414 (2)	C17—H17B	0.9900
C11—N1	1.2994 (19)	N1—H1N	0.94 (2)
C11—H11	0.9500
O1—C1—C10	122.68 (14)	N1—C12—H12B	109.3
O1—C1—C2	119.65 (15)	C13—C12—H12B	109.3
C10—C1—C2	117.67 (14)	H12A—C12—H12B	108.0
C3—C2—C1	121.38 (16)	C12—C13—C14	111.58 (13)
C3—C2—H2	119.3	C12—C13—H13A	109.3
C1—C2—H2	119.3	C14—C13—H13A	109.3
C2—C3—C4	122.38 (15)	C12—C13—H13B	109.3
C2—C3—H3	118.8	C14—C13—H13B	109.3
C4—C3—H3	118.8	H13A—C13—H13B	108.0
C5—C4—C9	120.10 (17)	C13—C14—C15	113.24 (13)
C5—C4—C3	120.99 (16)	C13—C14—H14A	108.9
C9—C4—C3	118.92 (15)	C15—C14—H14A	108.9
C6—C5—C4	121.31 (17)	C13—C14—H14B	108.9
C6—C5—H5	119.3	C15—C14—H14B	108.9
C4—C5—H5	119.3	H14A—C14—H14B	107.7
C5—C6—C7	119.16 (17)	C16—C15—C14	113.62 (13)
C5—C6—H6	120.4	C16—C15—H15A	108.8
C7—C6—H6	120.4	C14—C15—H15A	108.8
C8—C7—C6	120.85 (18)	C16—C15—H15B	108.8
C8—C7—H7	119.6	C14—C15—H15B	108.8
C6—C7—H7	119.6	H15A—C15—H15B	107.7
C7—C8—C9	121.47 (17)	C15—C16—C17	113.89 (13)
C7—C8—H8	119.3	C15—C16—H16A	108.8
C9—C8—H8	119.3	C17—C16—H16A	108.8
C8—C9—C4	117.11 (14)	C15—C16—H16B	108.8
C8—C9—C10	123.66 (14)	C17—C16—H16B	108.8
C4—C9—C10	119.23 (14)	H16A—C16—H16B	107.7
C11—C10—C1	118.31 (14)	C17i—C17—C16	113.82 (17)
C11—C10—C9	121.19 (14)	C17i—C17—H17A	108.8
C1—C10—C9	120.43 (13)	C16—C17—H17A	108.8
N1—C11—C10	123.61 (15)	C17i—C17—H17B	108.8
N1—C11—H11	118.2	C16—C17—H17B	108.8
C10—C11—H11	118.2	H17A—C17—H17B	107.7
N1—C12—C13	111.46 (13)	C11—N1—C12	123.87 (14)
N1—C12—H12A	109.3	C11—N1—H1N	112.7 (13)
C13—C12—H12A	109.3	C12—N1—H1N	123.4 (13)
O1—C1—C2—C3	179.64 (16)	C2—C1—C10—C11	176.23 (13)
C10—C1—C2—C3	0.1 (2)	O1—C1—C10—C9	179.73 (14)
C1—C2—C3—C4	0.2 (3)	C2—C1—C10—C9	−0.7 (2)
C2—C3—C4—C5	179.79 (17)	C8—C9—C10—C11	4.3 (2)
C2—C3—C4—C9	0.1 (2)	C4—C9—C10—C11	−175.79 (13)
C9—C4—C5—C6	0.5 (3)	C8—C9—C10—C1	−178.81 (14)
C3—C4—C5—C6	−179.20 (17)	C4—C9—C10—C1	1.1 (2)
C4—C5—C6—C7	−0.1 (3)	C1—C10—C11—N1	2.6 (2)
C5—C6—C7—C8	−0.2 (3)	C9—C10—C11—N1	179.54 (14)
C6—C7—C8—C9	0.1 (3)	N1—C12—C13—C14	179.84 (13)
C7—C8—C9—C4	0.3 (2)	C12—C13—C14—C15	−178.46 (13)
C7—C8—C9—C10	−179.84 (16)	C13—C14—C15—C16	177.58 (14)
C5—C4—C9—C8	−0.5 (2)	C14—C15—C16—C17	179.05 (13)
C3—C4—C9—C8	179.13 (15)	C15—C16—C17—C17i	179.32 (17)
C5—C4—C9—C10	179.57 (15)	C10—C11—N1—C12	−179.25 (14)
C3—C4—C9—C10	−0.8 (2)	C13—C12—N1—C11	−116.21 (16)
O1—C1—C10—C11	−3.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.94 (2)	1.75 (2)	2.5498 (18)	140.6 (19)

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1NO1	0.94(2)	1.75(2)	2.5498(18)	140.6(19)