4,4',6,6'-Tetra-tert-butyl-2,2'-[1,3-diazinane-1,3-diylbis(methyl-ene)]diphenol 0.25-hydrate.

The title compound, C(34)H(54)N(2)O(2)·0.25H(2)O, the organic mol-ecule, a potential tetra-dentate ligand with a bulky phenolic donor, has overall mirror symmetry. A partially occupied water mol-ecule of solvation is present in the lattice. The six-membered 1,3-diazinane ring displays a chair conformation. An intra-molecular O-H⋯N hydrogen bond ocurs. In the crystal, mol-ecules are linked by O-H⋯O inter-actions.

Related literature

For amino­bis­phenolato ligands in coordination chemistry, see: Wichmann et al. (2012 ▶). For applications of their metal complexes, see: Barroso et al. (2010 ▶); Wong et al. (2010 ▶); Kannan et al. (2008 ▶); Pang et al. (2008 ▶); Tshuva et al. (2001 ▶). For background to the synthetic procedure and related structures, see: Hancock et al. (2011 ▶); Manna et al. (2008 ▶); Mohanty et al. (2008 ▶); Guo et al. (2003 ▶).

Experimental

Crystal data

C34H54N2O2·0.25H2O

M = 527.30

Orthorhombic,

a = 8.7292 (8) Å

b = 37.428 (3) Å

c = 10.1806 (9) Å

V = 3326.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.33 × 0.24 × 0.16 mm

Data collection

Bruker SMART APEXII CCD diffractometer

29196 measured reflections

3908 independent reflections

3411 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.130

S = 1.05

3908 reflections

180 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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: publCIF (Westrip, 2010 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812026505/fj2558sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026505/fj2558Isup2.hkl

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

C34H54N2O2·0.25H2O	F(000) = 1162
Mr = 527.30	Dx = 1.053 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 9920 reflections
a = 8.7292 (8) Å	θ = 2.6–27.6°
b = 37.428 (3) Å	µ = 0.07 mm−1
c = 10.1806 (9) Å	T = 296 K
V = 3326.1 (5) Å3	Prism, colorless
Z = 4	0.33 × 0.24 × 0.16 mm

Bruker SMART APEXII CCD diffractometer	3411 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 27.6°, θmin = 1.6°
phi and ω scans	h = −11→11
29196 measured reflections	k = −48→48
3908 independent reflections	l = −13→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H-atom parameters constrained
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.0634P)2 + 1.2767P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.038
3908 reflections	Δρmax = 0.38 e Å−3
180 parameters	Δρmin = −0.31 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0034 (7)

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	Occ. (<1)
N1	0.24037 (12)	0.78185 (2)	0.40084 (10)	0.0226 (2)
O1	0.50878 (10)	0.81077 (2)	0.47464 (9)	0.0290 (2)
H1	0.4572	0.7956	0.4369	0.044*
O2	0.7322 (8)	0.7500	0.5233 (7)	0.0500 (15)*	0.25
H2	0.6880	0.7299	0.5133	0.075*	0.25
C1	0.44073 (13)	0.84373 (3)	0.46035 (11)	0.0218 (2)
C2	0.30352 (13)	0.84657 (3)	0.38874 (11)	0.0224 (2)
C3	0.23273 (13)	0.87966 (3)	0.37546 (12)	0.0228 (2)
H3A	0.1408	0.8812	0.3297	0.027*
C4	0.29645 (13)	0.91060 (3)	0.42917 (11)	0.0215 (2)
C5	0.43413 (13)	0.90681 (3)	0.49783 (11)	0.0220 (2)
H5A	0.4783	0.9272	0.5335	0.026*
C6	0.50974 (13)	0.87414 (3)	0.51622 (11)	0.0211 (2)
C7	0.21487 (13)	0.94668 (3)	0.41266 (12)	0.0248 (3)
C8	0.05775 (16)	0.94463 (4)	0.47962 (16)	0.0397 (3)
H8A	0.0056	0.9671	0.4697	0.060*
H8B	0.0712	0.9395	0.5713	0.060*
H8C	−0.0019	0.9260	0.4397	0.060*
C9	0.19124 (19)	0.95464 (4)	0.26617 (16)	0.0429 (4)
H9A	0.2890	0.9560	0.2232	0.064*
H9B	0.1386	0.9770	0.2565	0.064*
H9C	0.1314	0.9359	0.2272	0.064*
C10	0.30511 (17)	0.97759 (4)	0.4729 (2)	0.0484 (4)
H10A	0.4038	0.9792	0.4317	0.073*
H10B	0.3180	0.9735	0.5654	0.073*
H10C	0.2503	0.9995	0.4596	0.073*
C11	0.66220 (13)	0.87198 (3)	0.59218 (11)	0.0240 (3)
C12	0.71429 (15)	0.90887 (4)	0.64144 (14)	0.0334 (3)
H12A	0.6375	0.9187	0.6985	0.050*
H12B	0.7290	0.9245	0.5678	0.050*
H12C	0.8089	0.9065	0.6887	0.050*
C13	0.64494 (16)	0.84776 (4)	0.71373 (13)	0.0365 (3)
H13A	0.5661	0.8571	0.7698	0.055*
H13B	0.7401	0.8470	0.7609	0.055*
H13C	0.6178	0.8241	0.6862	0.055*
C14	0.78871 (14)	0.85726 (4)	0.50186 (12)	0.0299 (3)
H14A	0.7992	0.8725	0.4265	0.045*
H14B	0.7619	0.8336	0.4738	0.045*
H14C	0.8840	0.8565	0.5489	0.045*
C15	0.23842 (15)	0.81429 (3)	0.31813 (12)	0.0261 (3)
H15A	0.1338	0.8193	0.2919	0.031*
H15B	0.2976	0.8099	0.2391	0.031*
C16	0.2173 (2)	0.7500	0.32086 (16)	0.0228 (3)
H16A	0.2891	0.7500	0.2481	0.027*
H16B	0.1143	0.7500	0.2851	0.027*
C17	0.12559 (16)	0.78340 (3)	0.50660 (13)	0.0310 (3)
H17A	0.0237	0.7850	0.4690	0.037*
H17B	0.1426	0.8045	0.5601	0.037*
C18	0.1380 (3)	0.7500	0.59142 (19)	0.0369 (4)
H18A	0.2354	0.7500	0.6373	0.044*
H18B	0.0569	0.7500	0.6565	0.044*

	U11	U22	U33	U12	U13	U23
N1	0.0289 (5)	0.0148 (4)	0.0242 (5)	−0.0005 (3)	−0.0016 (4)	−0.0007 (3)
O1	0.0287 (4)	0.0196 (4)	0.0387 (5)	0.0034 (3)	−0.0068 (4)	0.0017 (3)
C1	0.0231 (5)	0.0188 (5)	0.0234 (5)	0.0019 (4)	0.0001 (4)	0.0021 (4)
C2	0.0261 (6)	0.0176 (5)	0.0235 (5)	−0.0020 (4)	−0.0028 (4)	0.0005 (4)
C3	0.0220 (5)	0.0199 (5)	0.0265 (6)	−0.0006 (4)	−0.0044 (4)	0.0013 (4)
C4	0.0203 (5)	0.0189 (5)	0.0252 (6)	−0.0002 (4)	0.0010 (4)	−0.0002 (4)
C5	0.0211 (5)	0.0205 (5)	0.0242 (5)	−0.0030 (4)	0.0009 (4)	−0.0028 (4)
C6	0.0195 (5)	0.0244 (5)	0.0195 (5)	−0.0009 (4)	0.0000 (4)	0.0006 (4)
C7	0.0225 (5)	0.0167 (5)	0.0352 (6)	0.0008 (4)	−0.0001 (5)	−0.0008 (4)
C8	0.0311 (7)	0.0340 (7)	0.0540 (9)	0.0073 (5)	0.0090 (6)	0.0041 (6)
C9	0.0556 (9)	0.0304 (6)	0.0429 (8)	0.0106 (6)	0.0013 (7)	0.0108 (6)
C10	0.0369 (8)	0.0217 (6)	0.0866 (13)	0.0031 (5)	−0.0134 (8)	−0.0140 (7)
C11	0.0202 (5)	0.0308 (6)	0.0210 (5)	0.0006 (4)	−0.0017 (4)	0.0005 (4)
C12	0.0252 (6)	0.0406 (7)	0.0345 (7)	−0.0015 (5)	−0.0065 (5)	−0.0092 (6)
C13	0.0314 (7)	0.0525 (8)	0.0257 (6)	−0.0013 (6)	−0.0032 (5)	0.0105 (6)
C14	0.0218 (6)	0.0394 (7)	0.0285 (6)	0.0023 (5)	−0.0008 (5)	−0.0026 (5)
C15	0.0343 (6)	0.0166 (5)	0.0274 (6)	−0.0020 (4)	−0.0081 (5)	0.0016 (4)
C16	0.0291 (8)	0.0159 (7)	0.0233 (8)	0.000	−0.0030 (6)	0.000
C17	0.0370 (7)	0.0227 (6)	0.0333 (7)	0.0019 (5)	0.0059 (5)	−0.0046 (5)
C18	0.0523 (12)	0.0298 (9)	0.0286 (9)	0.000	0.0117 (9)	0.000

N1—C16	1.4575 (13)	C10—H10A	0.9600
N1—C17	1.4719 (16)	C10—H10B	0.9600
N1—C15	1.4777 (14)	C10—H10C	0.9600
O1—C1	1.3770 (13)	C11—C14	1.5390 (17)
O1—H1	0.8200	C11—C12	1.5379 (17)
O2—H2	0.8500	C11—C13	1.5414 (17)
C1—C2	1.4062 (16)	C12—H12A	0.9600
C1—C6	1.4078 (15)	C12—H12B	0.9600
C2—C3	1.3909 (15)	C12—H12C	0.9600
C2—C15	1.5162 (15)	C13—H13A	0.9600
C3—C4	1.3962 (15)	C13—H13B	0.9600
C3—H3A	0.9300	C13—H13C	0.9600
C4—C5	1.3975 (16)	C14—H14A	0.9600
C4—C7	1.5359 (15)	C14—H14B	0.9600
C5—C6	1.4023 (16)	C14—H14C	0.9600
C5—H5A	0.9300	C15—H15A	0.9700
C6—C11	1.5414 (15)	C15—H15B	0.9700
C7—C10	1.5283 (17)	C16—N1i	1.4575 (13)
C7—C9	1.535 (2)	C16—H16A	0.9700
C7—C8	1.5335 (18)	C16—H16B	0.9700
C8—H8A	0.9600	C17—C18	1.5231 (16)
C8—H8B	0.9600	C17—H17A	0.9700
C8—H8C	0.9600	C17—H17B	0.9700
C9—H9A	0.9600	C18—C17i	1.5231 (16)
C9—H9B	0.9600	C18—H18A	0.9700
C9—H9C	0.9600	C18—H18B	0.9700
C16—N1—C17	110.29 (10)	C14—C11—C13	109.83 (10)
C16—N1—C15	110.62 (9)	C12—C11—C13	107.17 (10)
C17—N1—C15	112.13 (9)	C14—C11—C6	109.79 (9)
C1—O1—H1	109.5	C12—C11—C6	111.83 (10)
O1—C1—C2	119.33 (10)	C13—C11—C6	110.44 (10)
O1—C1—C6	119.81 (10)	C11—C12—H12A	109.5
C2—C1—C6	120.85 (10)	C11—C12—H12B	109.5
C3—C2—C1	119.74 (10)	H12A—C12—H12B	109.5
C3—C2—C15	119.80 (10)	C11—C12—H12C	109.5
C1—C2—C15	120.32 (10)	H12A—C12—H12C	109.5
C2—C3—C4	121.57 (10)	H12B—C12—H12C	109.5
C2—C3—H3A	119.2	C11—C13—H13A	109.5
C4—C3—H3A	119.2	C11—C13—H13B	109.5
C3—C4—C5	117.02 (10)	H13A—C13—H13B	109.5
C3—C4—C7	120.11 (10)	C11—C13—H13C	109.5
C5—C4—C7	122.87 (10)	H13A—C13—H13C	109.5
C4—C5—C6	124.06 (10)	H13B—C13—H13C	109.5
C4—C5—H5A	118.0	C11—C14—H14A	109.5
C6—C5—H5A	118.0	C11—C14—H14B	109.5
C5—C6—C1	116.73 (10)	H14A—C14—H14B	109.5
C5—C6—C11	121.28 (10)	C11—C14—H14C	109.5
C1—C6—C11	121.99 (10)	H14A—C14—H14C	109.5
C10—C7—C9	108.21 (12)	H14B—C14—H14C	109.5
C10—C7—C8	108.69 (11)	N1—C15—C2	112.34 (9)
C9—C7—C8	108.76 (11)	N1—C15—H15A	109.1
C10—C7—C4	112.50 (10)	C2—C15—H15A	109.1
C9—C7—C4	109.83 (10)	N1—C15—H15B	109.1
C8—C7—C4	108.78 (10)	C2—C15—H15B	109.1
C7—C8—H8A	109.5	H15A—C15—H15B	107.9
C7—C8—H8B	109.5	N1—C16—N1i	109.75 (13)
H8A—C8—H8B	109.5	N1—C16—H16A	109.7
C7—C8—H8C	109.5	N1i—C16—H16A	109.7
H8A—C8—H8C	109.5	N1—C16—H16B	109.7
H8B—C8—H8C	109.5	N1i—C16—H16B	109.7
C7—C9—H9A	109.5	H16A—C16—H16B	108.2
C7—C9—H9B	109.5	N1—C17—C18	109.51 (11)
H9A—C9—H9B	109.5	N1—C17—H17A	109.8
C7—C9—H9C	109.5	C18—C17—H17A	109.8
H9A—C9—H9C	109.5	N1—C17—H17B	109.8
H9B—C9—H9C	109.5	C18—C17—H17B	109.8
C7—C10—H10A	109.5	H17A—C17—H17B	108.2
C7—C10—H10B	109.5	C17i—C18—C17	110.30 (15)
H10A—C10—H10B	109.5	C17i—C18—H18A	109.6
C7—C10—H10C	109.5	C17—C18—H18A	109.6
H10A—C10—H10C	109.5	C17i—C18—H18B	109.6
H10B—C10—H10C	109.5	C17—C18—H18B	109.6
C14—C11—C12	107.71 (10)	H18A—C18—H18B	108.1

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	2.00	2.6880 (13)	142
O2—H2···O1i	0.85	2.22	3.036 (5)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	2.00	2.6880 (13)	142
O2—H2⋯O1i	0.85	2.22	3.036 (5)	161

Symmetry code: (i) .