10,21-Dimethyl-2,7,13,18-tetraphenyl-3,6,14,17-tetraazatricyclo[17.3.1.1]tetracosa-1(23),2,6,8(24),9,11,13,17,19,21-decaene-23,24-diol cyclohexane 0.33-solvate.

The title compound, C(46)H(40)N(4)O(2)·0.33C(6)H(12), was obtained unintentionally as a product of an attempted synthesis of a cadmium(II) complex of the [2,6-{PhSe(CH(2))(2)N=CPh}(2)C(6)H(2)(4-Me)(OH)] ligand. The full tetra-imino-diphenol macrocyclic ligand is generated by the application of an inversion centre. The macrocyclic ligand features strong intra-molecular O-H⋯N hydrogen bonds. The dihedral angles formed between the phenyl ring incorporated within the macrocycle and the peripheral phenyl rings are 82.99 (8) and 88.20 (8)°. The cyclo-hexane solvent mol-ecule lies about a site of [Formula: see text] symmetry. Other solvent within the lattice was disordered and was treated with the SQUEEZE routine [Spek (2009). Acta Cryst. D65, 148-155].

Related literature

For information on phenol-based Schiff base ligands, complexes and their applications, see: Vigato et al. (2007 ▶); Fenton et al. (2010 ▶); Avaji et al. (2009 ▶); Na et al. (2006 ▶); Dutta et al. (2004 ▶); Mandal et al. (1989 ▶); Gupta et al. (2002 ▶, 2010 ▶).

Experimental

Crystal data

3C46H40N4O2·C6H12

M = 2126.62

Rhombohedral,

a = 28.0966 (2) Å

c = 16.0265 (2) Å

α = 90°

γ = 120°

V = 10956.6 (2) Å3

Z = 3

Mo Kα radiation

μ = 0.06 mm−1

T = 295 K

0.44 × 0.41 × 0.32 mm

Data collection

Oxford Diffraction Gemini R diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.173, T max = 1.000

10270 measured reflections

5016 independent reflections

3022 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.222

S = 0.93

5016 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.85 e Å−3

Δρmin = −0.27 e Å−3

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

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811036622/tk2788sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036622/tk2788Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036622/tk2788Isup3.cml

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

3C46H40N4O2·C6H12	F(000) = 3384
Mr = 2126.62	Dx = 0.967 Mg m−3
Rhombohedral, R3	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -R 3	Cell parameters from 3689 reflections
a = 28.0966 (2) Å	θ = 4.2–77.4°
c = 16.0265 (2) Å	µ = 0.06 mm−1
α = 90°	T = 295 K
γ = 120°	Block, yellow
V = 10956.6 (2) Å3	0.44 × 0.41 × 0.32 mm
Z = 3

Oxford Diffraction Gemini R diffractometer	5016 independent reflections
Radiation source: fine-focus sealed tube	3022 reflections with I > 2σ(I)
graphite	Rint = 0.020
Detector resolution: 10.5081 pixels mm-1	θmax = 26.8°, θmin = 2.1°
φ and ω scans	h = −34→33
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −35→31
Tmin = 0.173, Tmax = 1.000	l = −17→19
10270 measured reflections

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.222	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.1584P)2] where P = (Fo2 + 2Fc2)/3
5016 reflections	(Δ/σ)max < 0.001
246 parameters	Δρmax = 0.85 e Å−3
0 restraints	Δρmin = −0.27 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
O1	0.00757 (6)	0.45286 (6)	0.94763 (8)	0.0730 (4)
H1O	−0.0035	0.4423	0.9952	0.088*
N1A	0.01498 (8)	0.43270 (7)	1.09956 (10)	0.0711 (4)
N1B	0.04471 (7)	0.53952 (7)	0.76712 (10)	0.0743 (5)
C1	0.06233 (8)	0.48575 (8)	0.94867 (12)	0.0624 (4)
C2	0.09343 (8)	0.49450 (8)	1.02149 (12)	0.0645 (5)
C3	0.15063 (9)	0.52866 (9)	1.01686 (13)	0.0724 (5)
H3A	0.1714	0.5343	1.0648	0.087*
C4	0.17723 (9)	0.55424 (9)	0.94371 (14)	0.0757 (5)
C5	0.14523 (9)	0.54553 (9)	0.87394 (13)	0.0752 (5)
H5A	0.1624	0.5629	0.8244	0.090*
C6	0.08866 (8)	0.51206 (8)	0.87453 (12)	0.0669 (5)
C7	0.23917 (11)	0.59108 (13)	0.9403 (2)	0.1046 (9)
H7A	0.2548	0.5740	0.9068	0.157*
H7B	0.2539	0.5968	0.9958	0.157*
H7C	0.2480	0.6258	0.9161	0.157*
C1A	−0.01466 (10)	0.40063 (10)	1.17263 (14)	0.0781 (6)
H1AA	0.0100	0.4121	1.2202	0.094*
H1AB	−0.0275	0.3620	1.1624	0.094*
C2A	0.06650 (9)	0.46672 (8)	1.10066 (12)	0.0663 (5)
C3A	0.10126 (9)	0.48103 (9)	1.17789 (12)	0.0694 (5)
C4A	0.11904 (9)	0.44689 (10)	1.20864 (14)	0.0775 (6)
H4AA	0.1107	0.4147	1.1806	0.093*
C5A	0.14966 (11)	0.46100 (12)	1.28222 (16)	0.0909 (7)
H5AA	0.1621	0.4382	1.3030	0.109*
C6A	0.16148 (12)	0.50778 (13)	1.32378 (18)	0.0991 (8)
H6AA	0.1817	0.5168	1.3730	0.119*
C7A	0.14353 (14)	0.54175 (13)	1.29287 (19)	0.1052 (9)
H7AA	0.1517	0.5738	1.3214	0.126*
C8A	0.11359 (12)	0.52882 (11)	1.22012 (15)	0.0878 (7)
H8AA	0.1017	0.5521	1.1995	0.105*
C1B	0.06337 (9)	0.59170 (9)	0.80786 (13)	0.0762 (6)
H1BA	0.0890	0.6212	0.7719	0.091*
H1BB	0.0824	0.5931	0.8591	0.091*
C2B	0.05487 (8)	0.50364 (8)	0.79799 (12)	0.0689 (5)
C3B	0.03317 (10)	0.45037 (9)	0.75241 (13)	0.0770 (6)
C4B	−0.00983 (11)	0.43386 (12)	0.69686 (16)	0.0958 (8)
H4BA	−0.0262	0.4553	0.6892	0.115*
C5B	−0.02877 (14)	0.38494 (14)	0.6522 (2)	0.1131 (10)
H5BA	−0.0584	0.3736	0.6161	0.136*
C6B	−0.00516 (16)	0.35455 (13)	0.6604 (2)	0.1179 (12)
H6BA	−0.0172	0.3230	0.6283	0.141*
C7B	0.03724 (17)	0.36951 (12)	0.7163 (2)	0.1160 (11)
H7BA	0.0533	0.3477	0.7229	0.139*
C8B	0.05599 (13)	0.41755 (11)	0.76307 (17)	0.0957 (8)
H8BA	0.0841	0.4274	0.8016	0.115*
C1S	0.2722 (4)	0.6162 (8)	1.1813 (4)	0.244 (6)
H1SA	0.2686	0.6132	1.2416	0.293*
H1SB	0.2379	0.5879	1.1573	0.293*

	U11	U22	U33	U12	U13	U23
O1	0.0741 (8)	0.0811 (9)	0.0525 (7)	0.0303 (7)	0.0009 (6)	0.0076 (6)
N1A	0.0838 (11)	0.0741 (10)	0.0554 (9)	0.0395 (9)	0.0047 (8)	0.0089 (7)
N1B	0.0852 (11)	0.0795 (10)	0.0536 (9)	0.0378 (9)	0.0032 (8)	0.0041 (7)
C1	0.0697 (11)	0.0624 (9)	0.0551 (10)	0.0330 (9)	0.0014 (8)	0.0006 (7)
C2	0.0766 (11)	0.0649 (10)	0.0563 (10)	0.0387 (9)	0.0002 (8)	0.0008 (8)
C3	0.0747 (12)	0.0779 (12)	0.0679 (12)	0.0407 (10)	−0.0049 (9)	−0.0011 (9)
C4	0.0710 (12)	0.0788 (12)	0.0751 (13)	0.0358 (10)	0.0028 (10)	0.0010 (10)
C5	0.0795 (13)	0.0786 (12)	0.0645 (12)	0.0372 (10)	0.0110 (9)	0.0067 (10)
C6	0.0750 (11)	0.0684 (10)	0.0557 (10)	0.0347 (9)	0.0045 (8)	0.0023 (8)
C7	0.0771 (15)	0.119 (2)	0.1015 (19)	0.0369 (14)	0.0056 (13)	0.0134 (16)
C1A	0.0922 (14)	0.0802 (13)	0.0623 (12)	0.0433 (11)	0.0065 (10)	0.0161 (9)
C2A	0.0833 (13)	0.0694 (11)	0.0554 (10)	0.0452 (10)	−0.0006 (8)	0.0010 (8)
C3A	0.0833 (12)	0.0795 (12)	0.0524 (9)	0.0460 (10)	0.0008 (8)	0.0044 (8)
C4A	0.0883 (14)	0.0843 (13)	0.0722 (13)	0.0523 (12)	−0.0018 (10)	0.0034 (10)
C5A	0.0928 (15)	0.1126 (19)	0.0818 (15)	0.0622 (14)	−0.0079 (12)	0.0121 (14)
C6A	0.1021 (18)	0.120 (2)	0.0752 (15)	0.0557 (17)	−0.0221 (13)	−0.0040 (14)
C7A	0.133 (2)	0.1024 (18)	0.0819 (16)	0.0597 (18)	−0.0228 (16)	−0.0222 (14)
C8A	0.1165 (18)	0.0890 (15)	0.0726 (13)	0.0622 (14)	−0.0160 (13)	−0.0088 (11)
C1B	0.0842 (13)	0.0747 (12)	0.0632 (11)	0.0349 (10)	0.0047 (10)	0.0084 (9)
C2B	0.0748 (11)	0.0757 (11)	0.0480 (9)	0.0315 (9)	0.0094 (8)	0.0048 (8)
C3B	0.0891 (14)	0.0745 (12)	0.0540 (10)	0.0309 (11)	0.0141 (9)	0.0006 (9)
C4B	0.0947 (16)	0.1020 (17)	0.0703 (14)	0.0340 (14)	0.0022 (12)	−0.0152 (12)
C5B	0.107 (2)	0.109 (2)	0.0857 (18)	0.0260 (17)	0.0073 (15)	−0.0288 (16)
C6B	0.124 (2)	0.0865 (18)	0.098 (2)	0.0187 (17)	0.0379 (19)	−0.0227 (15)
C7B	0.156 (3)	0.0860 (17)	0.099 (2)	0.0557 (19)	0.036 (2)	0.0008 (15)
C8B	0.125 (2)	0.0843 (15)	0.0737 (15)	0.0490 (15)	0.0074 (14)	−0.0013 (12)
C1S	0.195 (7)	0.318 (16)	0.099 (4)	0.037 (6)	−0.012 (4)	−0.054 (8)

O1—C1	1.342 (2)	C4A—H4AA	0.9300
O1—H1O	0.8200	C5A—C6A	1.358 (4)
N1A—C2A	1.275 (3)	C5A—H5AA	0.9300
N1A—C1A	1.458 (2)	C6A—C7A	1.375 (4)
N1B—C2B	1.277 (3)	C6A—H6AA	0.9300
N1B—C1B	1.443 (3)	C7A—C8A	1.376 (4)
C1—C6	1.400 (3)	C7A—H7AA	0.9300
C1—C2	1.404 (3)	C8A—H8AA	0.9300
C2—C3	1.402 (3)	C1B—C1Ai	1.521 (3)
C2—C2A	1.484 (3)	C1B—H1BA	0.9700
C3—C4	1.383 (3)	C1B—H1BB	0.9700
C3—H3A	0.9300	C2B—C3B	1.494 (3)
C4—C5	1.378 (3)	C3B—C8B	1.372 (4)
C4—C7	1.517 (3)	C3B—C4B	1.381 (4)
C5—C6	1.384 (3)	C4B—C5B	1.398 (4)
C5—H5A	0.9300	C4B—H4BA	0.9300
C6—C2B	1.496 (3)	C5B—C6B	1.324 (5)
C7—H7A	0.9600	C5B—H5BA	0.9300
C7—H7B	0.9600	C6B—C7B	1.378 (5)
C7—H7C	0.9600	C6B—H6BA	0.9300
C1A—C1Bi	1.520 (3)	C7B—C8B	1.396 (4)
C1A—H1AA	0.9700	C7B—H7BA	0.9300
C1A—H1AB	0.9700	C8B—H8BA	0.9300
C2A—C3A	1.502 (3)	C1S—C1Sii	1.657 (7)
C3A—C4A	1.375 (3)	C1S—C1Siii	1.658 (7)
C3A—C8A	1.384 (3)	C1S—H1SA	0.9700
C4A—C5A	1.395 (3)	C1S—H1SB	0.9700
C1—O1—H1O	109.5	C4A—C5A—H5AA	119.8
C2A—N1A—C1A	122.38 (18)	C5A—C6A—C7A	119.9 (2)
C2B—N1B—C1B	121.06 (18)	C5A—C6A—H6AA	120.1
O1—C1—C6	118.32 (17)	C7A—C6A—H6AA	120.1
O1—C1—C2	122.01 (17)	C6A—C7A—C8A	120.7 (3)
C6—C1—C2	119.67 (18)	C6A—C7A—H7AA	119.7
C3—C2—C1	118.41 (18)	C8A—C7A—H7AA	119.7
C3—C2—C2A	120.92 (18)	C7A—C8A—C3A	119.6 (2)
C1—C2—C2A	120.65 (18)	C7A—C8A—H8AA	120.2
C4—C3—C2	122.5 (2)	C3A—C8A—H8AA	120.2
C4—C3—H3A	118.8	N1B—C1B—C1Ai	109.98 (19)
C2—C3—H3A	118.8	N1B—C1B—H1BA	109.7
C5—C4—C3	117.41 (19)	C1Ai—C1B—H1BA	109.7
C5—C4—C7	121.1 (2)	N1B—C1B—H1BB	109.7
C3—C4—C7	121.5 (2)	C1Ai—C1B—H1BB	109.7
C4—C5—C6	122.7 (2)	H1BA—C1B—H1BB	108.2
C4—C5—H5A	118.6	N1B—C2B—C3B	117.44 (19)
C6—C5—H5A	118.6	N1B—C2B—C6	124.58 (19)
C5—C6—C1	119.25 (19)	C3B—C2B—C6	117.94 (19)
C5—C6—C2B	121.62 (18)	C8B—C3B—C4B	118.6 (2)
C1—C6—C2B	119.13 (17)	C8B—C3B—C2B	121.2 (2)
C4—C7—H7A	109.5	C4B—C3B—C2B	120.1 (2)
C4—C7—H7B	109.5	C3B—C4B—C5B	120.0 (3)
H7A—C7—H7B	109.5	C3B—C4B—H4BA	120.0
C4—C7—H7C	109.5	C5B—C4B—H4BA	120.0
H7A—C7—H7C	109.5	C6B—C5B—C4B	121.1 (3)
H7B—C7—H7C	109.5	C6B—C5B—H5BA	119.5
N1A—C1A—C1Bi	110.73 (17)	C4B—C5B—H5BA	119.5
N1A—C1A—H1AA	109.5	C5B—C6B—C7B	120.2 (3)
C1Bi—C1A—H1AA	109.5	C5B—C6B—H6BA	119.9
N1A—C1A—H1AB	109.5	C7B—C6B—H6BA	119.9
C1Bi—C1A—H1AB	109.5	C6B—C7B—C8B	119.6 (3)
H1AA—C1A—H1AB	108.1	C6B—C7B—H7BA	120.2
N1A—C2A—C2	118.15 (18)	C8B—C7B—H7BA	120.2
N1A—C2A—C3A	123.70 (18)	C3B—C8B—C7B	120.4 (3)
C2—C2A—C3A	118.15 (18)	C3B—C8B—H8BA	119.8
C4A—C3A—C8A	119.9 (2)	C7B—C8B—H8BA	119.8
C4A—C3A—C2A	121.5 (2)	C1Sii—C1S—C1Siii	112.3 (4)
C8A—C3A—C2A	118.47 (18)	C1Sii—C1S—H1SA	109.1
C3A—C4A—C5A	119.5 (2)	C1Siii—C1S—H1SA	109.1
C3A—C4A—H4AA	120.3	C1Sii—C1S—H1SB	109.1
C5A—C4A—H4AA	120.3	C1Siii—C1S—H1SB	109.1
C6A—C5A—C4A	120.5 (2)	H1SA—C1S—H1SB	107.9
C6A—C5A—H5AA	119.8
O1—C1—C2—C3	178.78 (18)	C8A—C3A—C4A—C5A	−0.3 (4)
C6—C1—C2—C3	−1.5 (3)	C2A—C3A—C4A—C5A	−177.8 (2)
O1—C1—C2—C2A	0.8 (3)	C3A—C4A—C5A—C6A	0.6 (4)
C6—C1—C2—C2A	−179.53 (17)	C4A—C5A—C6A—C7A	−0.5 (4)
C1—C2—C3—C4	0.6 (3)	C5A—C6A—C7A—C8A	0.1 (5)
C2A—C2—C3—C4	178.54 (19)	C6A—C7A—C8A—C3A	0.3 (5)
C2—C3—C4—C5	0.7 (3)	C4A—C3A—C8A—C7A	−0.2 (4)
C2—C3—C4—C7	179.9 (2)	C2A—C3A—C8A—C7A	177.4 (2)
C3—C4—C5—C6	−1.0 (3)	C2B—N1B—C1B—C1Ai	−122.1 (2)
C7—C4—C5—C6	179.8 (2)	C1B—N1B—C2B—C3B	178.98 (18)
C4—C5—C6—C1	0.0 (3)	C1B—N1B—C2B—C6	−3.4 (3)
C4—C5—C6—C2B	179.6 (2)	C5—C6—C2B—N1B	−73.2 (3)
O1—C1—C6—C5	−179.04 (18)	C1—C6—C2B—N1B	106.3 (2)
C2—C1—C6—C5	1.3 (3)	C5—C6—C2B—C3B	104.3 (2)
O1—C1—C6—C2B	1.4 (3)	C1—C6—C2B—C3B	−76.1 (2)
C2—C1—C6—C2B	−178.29 (18)	N1B—C2B—C3B—C8B	158.1 (2)
C2A—N1A—C1A—C1Bi	126.2 (2)	C6—C2B—C3B—C8B	−19.6 (3)
C1A—N1A—C2A—C2	175.90 (17)	N1B—C2B—C3B—C4B	−20.4 (3)
C1A—N1A—C2A—C3A	−5.3 (3)	C6—C2B—C3B—C4B	161.9 (2)
C3—C2—C2A—N1A	−174.41 (18)	C8B—C3B—C4B—C5B	−0.8 (4)
C1—C2—C2A—N1A	3.5 (3)	C2B—C3B—C4B—C5B	177.8 (2)
C3—C2—C2A—C3A	6.7 (3)	C3B—C4B—C5B—C6B	−1.9 (4)
C1—C2—C2A—C3A	−175.39 (17)	C4B—C5B—C6B—C7B	2.9 (5)
N1A—C2A—C3A—C4A	78.9 (3)	C5B—C6B—C7B—C8B	−1.4 (5)
C2—C2A—C3A—C4A	−102.2 (2)	C4B—C3B—C8B—C7B	2.3 (4)
N1A—C2A—C3A—C8A	−98.6 (3)	C2B—C3B—C8B—C7B	−176.3 (2)
C2—C2A—C3A—C8A	80.2 (3)	C6B—C7B—C8B—C3B	−1.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1A	0.82	1.81	2.532 (2)	146.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N1A	0.82	1.81	2.532 (2)	146