6,6'-Di-tert-butyl-4,4'-dimeth-oxy-2,2'-[1,3-diazinane-1,3-diylbis(methyl-ene)]diphenol 0.19-hydrate.

In the title hexa-hydro-pyrimidine derivative, C(28)H(42)N(2)O(4)·0.19H(2)O, the 1,3-diazinane ring has a chair conformation with a diequatorial substitution. The asymmetric unit contains one half-organic mol-ecule and a solvent water mol-ecule with occupany 0.095. The mol-ecule lies on a mirror plane perpendicular to [010] which passes through the C atoms at the 2- and 5-positions of the heterocyclic system. The partially occupied water mol-ecule is also located on this mirror plane. The dihedral angle between the planes of the aromatic rings is 17.71 (3)°. Two intra-molecular O-H⋯N hydrogen bonds with graph-set motif S(6) are present. No remarkable inter-molecular contacts exist in the crystal structure.

Related literature

For a related structure, see: Rivera et al. (2012a ▶). For the synthesis of the precursor, see: Rivera et al. (2010 ▶). For the preparation of the title compound, see: Rivera et al. (2012b ▶). For bond-length data, see: Allen et al. (1987 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For hydrogen-bond graph-set nomenclature, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C28H42N2O4·0.19H2O

M = 473.5

Orthorhombic,

a = 8.2265 (1) Å

b = 33.0103 (2) Å

c = 10.0322 (5) Å

V = 2724.34 (14) Å3

Z = 4

Cu Kα radiation

μ = 0.61 mm−1

T = 120 K

0.42 × 0.36 × 0.30 mm

Data collection

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.073, T max = 1

54017 measured reflections

2456 independent reflections

2353 reflections with I > 3σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.122

S = 2.64

2456 reflections

164 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811053542/go2039sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053542/go2039Isup2.hkl

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

C28H42N2O4·0.19H2O	F(000) = 1029.6
Mr = 473.5	Dx = 1.154 Mg m−3
Orthorhombic, Pnma	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ac 2n	Cell parameters from 37659 reflections
a = 8.2265 (1) Å	θ = 4.0–67.0°
b = 33.0103 (2) Å	µ = 0.61 mm−1
c = 10.0322 (5) Å	T = 120 K
V = 2724.34 (14) Å3	Block, colourless
Z = 4	0.42 × 0.36 × 0.30 mm

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	2456 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2353 reflections with I > 3σ(I)
mirror	Rint = 0.027
Detector resolution: 10.3784 pixels mm-1	θmax = 67.1°, θmin = 4.6°
Rotation method data acquisition using ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −39→39
Tmin = 0.073, Tmax = 1	l = −11→11
54017 measured reflections

Refinement on F2	85 constraints
R[F2 > 2σ(F2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.122	Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2)
S = 2.64	(Δ/σ)max = 0.005
2456 reflections	Δρmax = 0.17 e Å−3
164 parameters	Δρmin = −0.14 e Å−3
0 restraints

Experimental. CrysAlisPro, Agilent (2010), Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.48228 (8)	0.17951 (2)	0.02311 (7)	0.0238 (2)
O2	0.18527 (9)	0.03041 (2)	0.08155 (9)	0.0348 (3)
O3	0.2004 (8)	0.25	0.5283 (7)	0.040 (3)*	0.185 (6)
N1	0.20147 (9)	0.21389 (2)	0.09520 (8)	0.0196 (3)
C1	0.17203 (15)	0.25	0.17490 (13)	0.0188 (4)
C2	0.1074 (2)	0.25	−0.10270 (15)	0.0302 (4)
C3	0.08755 (13)	0.21221 (2)	−0.01750 (10)	0.0253 (3)
C4	0.19236 (11)	0.17724 (3)	0.17868 (10)	0.0219 (3)
C5	0.26169 (12)	0.14026 (3)	0.11072 (10)	0.0196 (3)
C6	0.40731 (11)	0.14256 (3)	0.03904 (9)	0.0189 (3)
C7	0.47830 (11)	0.10754 (3)	−0.01656 (9)	0.0197 (3)
C8	0.39696 (12)	0.07106 (3)	0.00193 (10)	0.0226 (3)
C9	0.25098 (12)	0.06858 (3)	0.07237 (10)	0.0235 (3)
C10	0.18330 (11)	0.10307 (3)	0.12733 (10)	0.0211 (3)
C11	0.64179 (11)	0.10927 (3)	−0.09068 (10)	0.0214 (3)
C12	0.63025 (13)	0.13705 (3)	−0.21310 (10)	0.0273 (3)
C13	0.77305 (12)	0.12524 (3)	0.00455 (10)	0.0271 (3)
C14	0.69608 (13)	0.06750 (3)	−0.13975 (12)	0.0323 (3)
C15	0.04374 (13)	0.02586 (3)	0.16101 (14)	0.0390 (4)
H1	0.4062 (18)	0.1977 (5)	0.0432 (14)	0.0357*
H1a	0.243304	0.25	0.250666	0.0225*
H1b	0.061463	0.25	0.205494	0.0225*
H2a	0.213383	0.25	−0.142824	0.0362*
H2b	0.027077	0.25	−0.17208	0.0362*
H3a	−0.021813	0.210856	0.015603	0.0304*
H3b	0.11002	0.188634	−0.070414	0.0304*
H4a	0.081224	0.172204	0.202722	0.0263*
H4b	0.248999	0.181858	0.260948	0.0263*
H8	0.442701	0.046769	−0.034967	0.0271*
H10	0.083356	0.101481	0.176454	0.0253*
H12a	0.59744	0.16367	−0.185502	0.041*
H12b	0.734431	0.138538	−0.255938	0.041*
H12c	0.551668	0.126314	−0.274392	0.041*
H13a	0.751922	0.153186	0.024643	0.0407*
H13b	0.771525	0.109711	0.085441	0.0407*
H13c	0.877797	0.122826	−0.036879	0.0407*
H14a	0.796577	0.070049	−0.187653	0.0484*
H14b	0.711271	0.04983	−0.064775	0.0484*
H14c	0.614427	0.056424	−0.197596	0.0484*
H15a	0.010043	−0.001985	0.160156	0.0585*
H15b	0.067158	0.033969	0.25087	0.0585*
H15c	−0.041734	0.042506	0.125745	0.0585*

	U11	U22	U33	U12	U13	U23
O1	0.0244 (4)	0.0180 (4)	0.0289 (5)	−0.0026 (3)	0.0051 (3)	−0.0005 (3)
O2	0.0366 (5)	0.0176 (4)	0.0502 (6)	−0.0053 (3)	0.0152 (3)	−0.0021 (3)
N1	0.0249 (4)	0.0159 (4)	0.0180 (5)	0.0012 (3)	0.0013 (3)	0.0002 (3)
C1	0.0219 (6)	0.0169 (6)	0.0175 (7)	0	0.0009 (5)	0
C2	0.0451 (9)	0.0234 (7)	0.0220 (8)	0	−0.0092 (6)	0
C3	0.0336 (6)	0.0185 (5)	0.0239 (5)	−0.0007 (4)	−0.0056 (4)	−0.0031 (4)
C4	0.0271 (5)	0.0174 (5)	0.0213 (5)	0.0011 (3)	0.0042 (4)	0.0025 (4)
C5	0.0220 (5)	0.0188 (5)	0.0180 (5)	0.0020 (3)	−0.0016 (3)	0.0024 (3)
C6	0.0207 (5)	0.0183 (5)	0.0176 (5)	−0.0007 (3)	−0.0023 (4)	0.0018 (3)
C7	0.0203 (5)	0.0220 (5)	0.0167 (5)	0.0022 (3)	−0.0025 (3)	0.0004 (3)
C8	0.0254 (5)	0.0188 (5)	0.0236 (5)	0.0035 (4)	0.0001 (4)	−0.0011 (4)
C9	0.0263 (5)	0.0181 (5)	0.0263 (6)	−0.0020 (4)	−0.0001 (4)	0.0022 (4)
C10	0.0205 (5)	0.0208 (5)	0.0221 (5)	0.0007 (3)	0.0008 (4)	0.0034 (3)
C11	0.0210 (5)	0.0239 (5)	0.0195 (5)	0.0012 (4)	0.0011 (4)	−0.0010 (4)
C12	0.0244 (5)	0.0374 (5)	0.0202 (5)	0.0025 (4)	0.0024 (4)	0.0034 (4)
C13	0.0199 (5)	0.0395 (6)	0.0220 (5)	0.0003 (4)	0.0005 (4)	−0.0012 (4)
C14	0.0290 (5)	0.0293 (5)	0.0386 (7)	0.0041 (4)	0.0097 (5)	−0.0059 (4)
C15	0.0367 (6)	0.0233 (5)	0.0570 (8)	−0.0070 (4)	0.0153 (5)	0.0034 (5)

O1—C6	1.3762 (11)	C7—C8	1.3899 (13)
O1—H1	0.890 (15)	C7—C11	1.5379 (13)
O2—C9	1.3743 (12)	C8—C9	1.3958 (14)
O2—C15	1.4190 (14)	C8—H8	0.96
N1—C1	1.4555 (10)	C9—C10	1.3821 (13)
N1—C3	1.4696 (13)	C10—H10	0.96
N1—C4	1.4736 (11)	C11—C12	1.5358 (14)
C1—H1a	0.96	C11—C13	1.5353 (14)
C1—H1b	0.96	C11—C14	1.5306 (14)
C2—C3	1.5211 (12)	C12—H12a	0.96
C2—C3i	1.5211 (12)	C12—H12b	0.96
C2—H2a	0.96	C12—H12c	0.96
C2—H2b	0.96	C13—H13a	0.96
C3—H3a	0.96	C13—H13b	0.96
C3—H3b	0.96	C13—H13c	0.96
C4—C5	1.5100 (12)	C14—H14a	0.96
C4—H4a	0.96	C14—H14b	0.96
C4—H4b	0.96	C14—H14c	0.96
C5—C6	1.3993 (13)	C15—H15a	0.96
C5—C10	1.3966 (12)	C15—H15b	0.96
C6—C7	1.4103 (13)	C15—H15c	0.96
C6—O1—H1	104.8 (10)	C7—C8—H8	118.9115
C9—O2—C15	117.23 (8)	C9—C8—H8	118.9125
C1—N1—C3	110.33 (7)	O2—C9—C8	115.22 (8)
C1—N1—C4	110.60 (8)	O2—C9—C10	124.76 (9)
C3—N1—C4	111.94 (7)	C8—C9—C10	120.02 (8)
N1—C1—N1i	109.94 (10)	C5—C10—C9	119.37 (9)
N1—C1—H1a	109.4711	C5—C10—H10	120.3163
N1—C1—H1b	109.4713	C9—C10—H10	120.3168
N1i—C1—H1a	109.4711	C7—C11—C12	110.78 (8)
N1i—C1—H1b	109.4713	C7—C11—C13	109.09 (8)
H1a—C1—H1b	108.995	C7—C11—C14	112.16 (8)
C3—C2—C3i	110.20 (11)	C12—C11—C13	109.63 (8)
C3—C2—H2a	109.4711	C12—C11—C14	107.38 (8)
C3—C2—H2b	109.4714	C13—C11—C14	107.72 (8)
C3i—C2—H2a	109.4711	C11—C12—H12a	109.4717
C3i—C2—H2b	109.4714	C11—C12—H12b	109.472
H2a—C2—H2b	108.7329	C11—C12—H12c	109.4713
N1—C3—C2	109.43 (9)	H12a—C12—H12b	109.4696
N1—C3—H3a	109.4709	H12a—C12—H12c	109.4713
N1—C3—H3b	109.4712	H12b—C12—H12c	109.4714
C2—C3—H3a	109.4713	C11—C13—H13a	109.4718
C2—C3—H3b	109.4714	C11—C13—H13b	109.4714
H3a—C3—H3b	109.5159	C11—C13—H13c	109.4712
N1—C4—C5	112.83 (8)	H13a—C13—H13b	109.4709
N1—C4—H4a	109.4712	H13a—C13—H13c	109.4705
N1—C4—H4b	109.4728	H13b—C13—H13c	109.4715
C5—C4—H4a	109.4707	C11—C14—H14a	109.4717
C5—C4—H4b	109.4701	C11—C14—H14b	109.4711
H4a—C4—H4b	105.8863	C11—C14—H14c	109.4716
C4—C5—C6	120.76 (8)	H14a—C14—H14b	109.4711
C4—C5—C10	118.83 (8)	H14a—C14—H14c	109.4707
C6—C5—C10	120.29 (8)	H14b—C14—H14c	109.4712
O1—C6—C5	119.44 (8)	O2—C15—H15a	109.4715
O1—C6—C7	119.68 (8)	O2—C15—H15b	109.4712
C5—C6—C7	120.88 (8)	O2—C15—H15c	109.4719
C6—C7—C8	117.26 (8)	H15a—C15—H15b	109.4706
C6—C7—C11	121.53 (8)	H15a—C15—H15c	109.4704
C8—C7—C11	121.18 (8)	H15b—C15—H15c	109.4716
C7—C8—C9	122.18 (8)
C15—O2—C9—C8	175.19 (9)	O1—C6—C7—C11	2.32 (13)
C15—O2—C9—C10	−4.54 (15)	C5—C6—C7—C8	0.56 (14)
C3—N1—C1—N1i	−62.71 (10)	C5—C6—C7—C11	−177.47 (9)
C4—N1—C1—N1i	172.88 (8)	C6—C7—C8—C9	−0.03 (15)
C1—N1—C3—C2	58.60 (11)	C11—C7—C8—C9	178.01 (9)
C4—N1—C3—C2	−177.78 (8)	C6—C7—C11—C12	−61.16 (11)
C1—N1—C4—C5	−165.79 (8)	C6—C7—C11—C13	59.62 (11)
C3—N1—C4—C5	70.73 (10)	C6—C7—C11—C14	178.86 (9)
C3i—C2—C3—N1	−54.82 (13)	C8—C7—C11—C12	120.88 (10)
N1—C4—C5—C6	43.06 (12)	C8—C7—C11—C13	−118.34 (10)
N1—C4—C5—C10	−140.83 (9)	C8—C7—C11—C14	0.91 (13)
C4—C5—C6—O1	−4.30 (14)	C7—C8—C9—O2	179.76 (9)
C4—C5—C6—C7	175.48 (9)	C7—C8—C9—C10	−0.50 (15)
C10—C5—C6—O1	179.64 (9)	O2—C9—C10—C5	−179.80 (10)
C10—C5—C6—C7	−0.58 (14)	C8—C9—C10—C5	0.49 (15)
C4—C5—C10—C9	−176.10 (9)	H1—O1—C6—C5	−16.4 (9)
C6—C5—C10—C9	0.03 (15)	H1—O1—C6—C7	163.8 (9)
O1—C6—C7—C8	−179.65 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.890 (15)	1.843 (15)	2.6735 (10)	154.6 (14)
C12—H12a···O1	0.96	2.36	3.0103 (12)	124.92
C13—H13a···O1	0.96	2.38	2.9943 (12)	121.18

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.890 (15)	1.843 (15)	2.6735 (10)	154.6 (14)