1,5-Dichloro-3(2,7),7(2,7)-dinaphthal-ena-2,4,6,8-tetra-oxa-1(2,6),5(2,6)-di(1,3,5-triazina)octa-phane.

In the macrocyclic title compound, C(26)H(12)Cl(2)N(6)O(4), an O-atom-bridged calix[2]naphthalene-[2]triazine synthesized using a one-pot approach from naphthalene-2,7-diol and cyanuric chloride, the two isolated naphthalene planes and the two triazine-2,6-di-oxy planes adopt a 1,3-alternate configuration, with a dihedral angle of 84.10 (8)° between the naphthalene rings and a dihedral angle of 39.02 (14)° between the triazine rings. In the crystal, weak inter-molecular π-π stacking inter-actions are found between face-to-face naphthalene rings [centroid-centroid distance = 3.662 (7) Å].

Related literature

For general background and applications of oxocalixarenes, see König & Fonseca (2000 ▶). For background on compounds similar to the title compound and other derivatives from cyanuric chloride reactions, see: Wang & Yang (2004 ▶); Hou et al. (2007 ▶); Chen et al. (2010 ▶); Zhu et al. (2010 ▶); Katz et al. (2009 ▶); Katz & Tschaen (2010 ▶); Hu & Chen (2011 ▶).

Experimental

Crystal data

C26H12Cl2N6O4

M = 543.32

Monoclinic,

a = 15.514 (3) Å

b = 7.967 (3) Å

c = 18.527 (5) Å

β = 90.60 (2)°

V = 2289.8 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 295 K

0.5 × 0.4 × 0.3 mm

Data collection

Bruker P4 diffractometer

5492 measured reflections

4266 independent reflections

2582 reflections with I > 2σ(I)

R int = 0.034

3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.123

S = 1.03

4266 reflections

343 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.39 e Å−3

Data collection: XSCANS (Bruker, 1997 ▶); cell refinement: XSCANS; data reduction: XSCANS; 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681103460X/zs2134sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103460X/zs2134Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681103460X/zs2134Isup3.cml

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

C26H12Cl2N6O4	F(000) = 1104
Mr = 543.32	Dx = 1.576 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 49 reflections
a = 15.514 (3) Å	θ = 4.9–12.5°
b = 7.967 (3) Å	µ = 0.33 mm−1
c = 18.527 (5) Å	T = 295 K
β = 90.60 (2)°	Prism, colorless
V = 2289.8 (11) Å3	0.5 × 0.4 × 0.3 mm
Z = 4

Bruker P4 diffractometer	Rint = 0.034
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 2.2°
graphite	h = −1→18
ω scans	k = −9→1
5492 measured reflections	l = −22→22
4266 independent reflections	3 standard reflections every 97 reflections
2582 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.001P)2 + 2.80P] where P = (Fo2 + 2Fc2)/3
4266 reflections	(Δ/σ)max = 0.001
343 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.39 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
Cl1	0.65337 (5)	0.52005 (17)	−0.13220 (4)	0.1212 (4)
Cl2	0.65653 (5)	0.52943 (15)	0.69093 (4)	0.1076 (3)
O1	0.82098 (10)	0.4316 (3)	0.08191 (8)	0.0752 (6)
O2	0.53757 (10)	0.2524 (3)	0.07781 (8)	0.0778 (6)
O3	0.53255 (10)	0.2821 (3)	0.47773 (8)	0.0755 (6)
O4	0.81654 (11)	0.4587 (3)	0.47411 (8)	0.0830 (7)
N1	0.68020 (12)	0.3369 (3)	0.08891 (9)	0.0595 (6)
N2	0.59479 (13)	0.3744 (4)	−0.01723 (10)	0.0766 (8)
N3	0.73930 (13)	0.4742 (3)	−0.01449 (10)	0.0691 (7)
N4	0.67511 (12)	0.3658 (3)	0.46679 (9)	0.0602 (6)
N5	0.73800 (13)	0.4956 (3)	0.57144 (10)	0.0689 (7)
N6	0.59290 (13)	0.3986 (3)	0.57365 (10)	0.0742 (8)
C1	0.74257 (15)	0.4122 (4)	0.05242 (11)	0.0617 (8)
C2	0.60781 (15)	0.3243 (4)	0.05096 (12)	0.0633 (8)
C3	0.66290 (17)	0.4477 (4)	−0.04477 (12)	0.0747 (10)
C4	0.52151 (14)	0.1967 (4)	0.14883 (12)	0.0627 (8)
C5	0.55811 (14)	0.2556 (4)	0.21090 (11)	0.0591 (8)
H5	0.6042	0.3301	0.2092	0.071*
C6	0.52496 (13)	0.2016 (3)	0.27861 (11)	0.0538 (7)
C7	0.55644 (14)	0.2663 (4)	0.34550 (11)	0.0585 (7)
H7	0.6025	0.3410	0.3467	0.070*
C8	0.51762 (14)	0.2166 (4)	0.40796 (12)	0.0593 (7)
C9	0.44956 (16)	0.1016 (4)	0.40900 (13)	0.0718 (9)
H9	0.4251	0.0699	0.4525	0.086*
C10	0.41959 (17)	0.0367 (4)	0.34581 (14)	0.0742 (9)
H10	0.3747	−0.0407	0.3464	0.089*
C11	0.45556 (15)	0.0848 (4)	0.27896 (13)	0.0596 (7)
C12	0.42190 (16)	0.0250 (4)	0.21229 (13)	0.0707 (9)
H12	0.3773	−0.0531	0.2122	0.085*
C13	0.45381 (16)	0.0801 (4)	0.14867 (13)	0.0680 (8)
H13	0.4309	0.0409	0.1052	0.082*
C14	0.60391 (15)	0.3501 (4)	0.50520 (12)	0.0617 (8)
C15	0.73893 (15)	0.4367 (4)	0.50414 (12)	0.0628 (8)
C16	0.66226 (16)	0.4676 (4)	0.60166 (12)	0.0711 (9)
C17	0.83673 (14)	0.3801 (4)	0.40794 (12)	0.0649 (8)
C18	0.80149 (14)	0.4335 (4)	0.34460 (12)	0.0619 (8)
H18	0.7573	0.5124	0.3442	0.074*
C19	0.83321 (13)	0.3669 (3)	0.27905 (11)	0.0526 (7)
C20	0.80400 (14)	0.4258 (4)	0.21136 (11)	0.0600 (8)
H20	0.7604	0.5056	0.2083	0.072*
C21	0.84044 (14)	0.3642 (4)	0.15079 (11)	0.0598 (8)
C22	0.90542 (15)	0.2455 (4)	0.15168 (12)	0.0688 (9)
H22	0.9289	0.2073	0.1087	0.083*
C23	0.93466 (15)	0.1852 (4)	0.21650 (13)	0.0694 (9)
H23	0.9776	0.1038	0.2176	0.083*
C24	0.89995 (14)	0.2457 (4)	0.28203 (12)	0.0568 (7)
C25	0.93288 (16)	0.1943 (4)	0.35013 (13)	0.0692 (8)
H25	0.9760	0.1133	0.3524	0.083*
C26	0.90224 (15)	0.2621 (4)	0.41220 (13)	0.0709 (9)
H26	0.9249	0.2298	0.4567	0.085*

	U11	U22	U33	U12	U13	U23
Cl1	0.0746 (4)	0.2384 (12)	0.0506 (3)	0.0012 (6)	−0.0046 (3)	0.0454 (5)
Cl2	0.0756 (4)	0.2001 (10)	0.0471 (3)	0.0050 (6)	0.0059 (3)	−0.0316 (5)
O1	0.0544 (9)	0.1312 (17)	0.0398 (8)	−0.0206 (11)	−0.0037 (7)	0.0095 (10)
O2	0.0486 (8)	0.1420 (18)	0.0427 (8)	−0.0147 (11)	−0.0059 (7)	0.0066 (11)
O3	0.0551 (9)	0.1297 (17)	0.0419 (8)	−0.0138 (11)	0.0075 (7)	−0.0027 (10)
O4	0.0607 (10)	0.1476 (19)	0.0408 (8)	−0.0245 (12)	0.0062 (7)	−0.0147 (11)
N1	0.0488 (10)	0.0919 (17)	0.0378 (9)	−0.0054 (11)	−0.0024 (8)	0.0008 (11)
N2	0.0522 (11)	0.140 (2)	0.0375 (10)	0.0013 (14)	−0.0029 (8)	0.0050 (13)
N3	0.0570 (11)	0.1115 (19)	0.0390 (9)	0.0026 (13)	0.0015 (9)	0.0053 (12)
N4	0.0500 (10)	0.0920 (17)	0.0386 (9)	−0.0036 (11)	0.0027 (8)	0.0032 (11)
N5	0.0604 (11)	0.1070 (18)	0.0392 (9)	0.0003 (13)	0.0023 (9)	−0.0046 (12)
N6	0.0567 (11)	0.125 (2)	0.0406 (10)	0.0021 (14)	0.0079 (9)	−0.0046 (13)
C1	0.0560 (13)	0.093 (2)	0.0364 (11)	−0.0030 (14)	0.0004 (10)	−0.0035 (13)
C2	0.0502 (12)	0.098 (2)	0.0416 (12)	0.0017 (14)	0.0008 (10)	−0.0032 (14)
C3	0.0634 (14)	0.124 (3)	0.0367 (11)	0.0123 (17)	0.0017 (11)	0.0055 (15)
C4	0.0411 (11)	0.102 (2)	0.0450 (12)	0.0043 (14)	0.0000 (10)	0.0044 (14)
C5	0.0420 (11)	0.089 (2)	0.0466 (12)	−0.0048 (13)	−0.0003 (10)	0.0008 (13)
C6	0.0417 (11)	0.0732 (18)	0.0465 (12)	0.0027 (12)	0.0019 (9)	0.0015 (12)
C7	0.0444 (11)	0.085 (2)	0.0456 (12)	−0.0032 (13)	0.0034 (10)	0.0006 (13)
C8	0.0500 (12)	0.0840 (19)	0.0439 (12)	0.0008 (14)	0.0034 (10)	0.0007 (13)
C9	0.0640 (15)	0.100 (2)	0.0515 (13)	−0.0133 (16)	0.0095 (12)	0.0104 (15)
C10	0.0652 (15)	0.094 (2)	0.0636 (15)	−0.0169 (16)	0.0032 (13)	0.0072 (16)
C11	0.0544 (13)	0.0697 (18)	0.0548 (13)	−0.0017 (14)	0.0010 (11)	0.0009 (13)
C12	0.0581 (14)	0.088 (2)	0.0662 (15)	−0.0133 (15)	−0.0057 (12)	0.0018 (16)
C13	0.0553 (13)	0.096 (2)	0.0526 (13)	0.0009 (15)	−0.0088 (11)	−0.0085 (15)
C14	0.0547 (13)	0.089 (2)	0.0414 (12)	0.0026 (14)	0.0035 (10)	0.0065 (13)
C15	0.0557 (13)	0.093 (2)	0.0398 (12)	−0.0008 (15)	0.0043 (10)	0.0062 (13)
C16	0.0646 (15)	0.111 (2)	0.0381 (12)	0.0114 (17)	0.0021 (11)	−0.0040 (14)
C17	0.0473 (12)	0.108 (2)	0.0394 (11)	−0.0155 (15)	0.0051 (10)	−0.0034 (14)
C18	0.0441 (12)	0.094 (2)	0.0478 (12)	−0.0017 (14)	0.0026 (10)	−0.0023 (14)
C19	0.0395 (10)	0.0774 (18)	0.0410 (11)	−0.0060 (12)	0.0017 (9)	0.0009 (12)
C20	0.0449 (12)	0.090 (2)	0.0449 (12)	−0.0001 (13)	−0.0035 (10)	0.0028 (13)
C21	0.0462 (12)	0.095 (2)	0.0385 (11)	−0.0101 (14)	−0.0035 (9)	0.0041 (13)
C22	0.0496 (12)	0.109 (2)	0.0479 (13)	−0.0041 (15)	0.0072 (10)	−0.0134 (15)
C23	0.0493 (13)	0.092 (2)	0.0670 (15)	0.0088 (15)	0.0016 (12)	−0.0102 (16)
C24	0.0423 (11)	0.0809 (19)	0.0471 (12)	−0.0031 (13)	0.0003 (10)	0.0034 (13)
C25	0.0530 (13)	0.094 (2)	0.0600 (14)	0.0030 (15)	−0.0077 (11)	0.0080 (15)
C26	0.0535 (13)	0.111 (2)	0.0477 (13)	−0.0140 (16)	−0.0073 (11)	0.0144 (15)

Cl1—C3	1.724 (2)	C7—C8	1.369 (3)
Cl2—C16	1.729 (2)	C7—H7	0.9300
O1—C1	1.337 (3)	C8—C9	1.398 (4)
O1—C21	1.414 (3)	C9—C10	1.357 (4)
O2—C2	1.332 (3)	C9—H9	0.9300
O2—C4	1.413 (3)	C10—C11	1.417 (3)
O3—C14	1.329 (3)	C10—H10	0.9300
O3—C8	1.411 (3)	C11—C12	1.418 (3)
O4—C15	1.343 (3)	C12—C13	1.356 (4)
O4—C17	1.414 (3)	C12—H12	0.9300
N1—C2	1.323 (3)	C13—H13	0.9300
N1—C1	1.329 (3)	C17—C18	1.358 (3)
N2—C3	1.315 (3)	C17—C26	1.386 (4)
N2—C2	1.338 (3)	C18—C19	1.418 (3)
N3—C3	1.323 (3)	C18—H18	0.9300
N3—C1	1.335 (3)	C19—C20	1.409 (3)
N4—C14	1.326 (3)	C19—C24	1.416 (3)
N4—C15	1.328 (3)	C20—C21	1.354 (3)
N5—C16	1.326 (3)	C20—H20	0.9300
N5—C15	1.333 (3)	C21—C22	1.382 (4)
N6—C16	1.311 (3)	C22—C23	1.367 (3)
N6—C14	1.338 (3)	C22—H22	0.9300
C4—C5	1.361 (3)	C23—C24	1.418 (3)
C4—C13	1.402 (4)	C23—H23	0.9300
C5—C6	1.427 (3)	C24—C25	1.417 (3)
C5—H5	0.9300	C25—C26	1.361 (4)
C6—C11	1.424 (3)	C25—H25	0.9300
C6—C7	1.424 (3)	C26—H26	0.9300
C1—O1—C21	120.63 (19)	C13—C12—H12	119.6
C2—O2—C4	129.45 (18)	C11—C12—H12	119.6
C14—O3—C8	129.02 (18)	C12—C13—C4	119.5 (2)
C15—O4—C17	120.6 (2)	C12—C13—H13	120.2
C2—N1—C1	112.49 (19)	C4—C13—H13	120.2
C3—N2—C2	112.6 (2)	N4—C14—O3	121.9 (2)
C3—N3—C1	111.1 (2)	N4—C14—N6	126.6 (2)
C14—N4—C15	112.40 (19)	O3—C14—N6	111.5 (2)
C16—N5—C15	110.8 (2)	N4—C15—N5	128.5 (2)
C16—N6—C14	112.6 (2)	N4—C15—O4	120.4 (2)
N1—C1—N3	128.2 (2)	N5—C15—O4	111.1 (2)
N1—C1—O1	120.5 (2)	N6—C16—N5	129.1 (2)
N3—C1—O1	111.2 (2)	N6—C16—Cl2	116.61 (18)
N1—C2—O2	121.8 (2)	N5—C16—Cl2	114.27 (19)
N1—C2—N2	126.7 (2)	C18—C17—C26	123.4 (2)
O2—C2—N2	111.4 (2)	C18—C17—O4	121.3 (3)
N2—C3—N3	128.8 (2)	C26—C17—O4	114.8 (2)
N2—C3—Cl1	116.84 (19)	C17—C18—C19	118.9 (2)
N3—C3—Cl1	114.4 (2)	C17—C18—H18	120.6
C5—C4—C13	122.4 (2)	C19—C18—H18	120.6
C5—C4—O2	127.1 (2)	C20—C19—C24	119.3 (2)
C13—C4—O2	110.2 (2)	C20—C19—C18	121.8 (2)
C4—C5—C6	119.2 (2)	C24—C19—C18	118.8 (2)
C4—C5—H5	120.4	C21—C20—C19	118.9 (2)
C6—C5—H5	120.4	C21—C20—H20	120.5
C11—C6—C7	119.0 (2)	C19—C20—H20	120.5
C11—C6—C5	118.7 (2)	C20—C21—C22	123.3 (2)
C7—C6—C5	122.2 (2)	C20—C21—O1	121.6 (2)
C8—C7—C6	118.8 (2)	C22—C21—O1	114.8 (2)
C8—C7—H7	120.6	C23—C22—C21	119.1 (2)
C6—C7—H7	120.6	C23—C22—H22	120.4
C7—C8—C9	122.7 (2)	C21—C22—H22	120.4
C7—C8—O3	126.7 (2)	C22—C23—C24	120.5 (3)
C9—C8—O3	110.3 (2)	C22—C23—H23	119.8
C10—C9—C8	119.3 (2)	C24—C23—H23	119.8
C10—C9—H9	120.3	C19—C24—C25	119.2 (2)
C8—C9—H9	120.3	C19—C24—C23	118.9 (2)
C9—C10—C11	121.1 (3)	C25—C24—C23	121.8 (2)
C9—C10—H10	119.5	C26—C25—C24	120.8 (3)
C11—C10—H10	119.5	C26—C25—H25	119.6
C10—C11—C12	121.7 (2)	C24—C25—H25	119.6
C10—C11—C6	119.1 (2)	C25—C26—C17	118.9 (2)
C12—C11—C6	119.2 (2)	C25—C26—H26	120.5
C13—C12—C11	120.9 (3)	C17—C26—H26	120.5