1,3-Bis(3-tert-butyl-2-hy-droxy-5-meth-oxy-benz-yl)hexa-hydro-pyrimidin-5-ol monohydrate.

The asymmetric unit of the title compound, C28H42N2O5·H2O, consists of one half of the organic mol-ecule and one half-mol-ecule of water, both of which are located on a mirror plane which passes through the central C atoms and the hydroxyl group of the heterocyclic system. The hydroxyl group at the central ring is disordered over two equally occupied positions. The six-membered ring adopts a chair conformation, and the 2-hy-droxy-benzyl substituents occupy the sterically preferred equatorial positions. The aromatic rings make dihedral angles of 75.57 (9)° with the mean plane of the heterocyclic ring. The dihedral angle between the two aromatic rings is 19.18 (10)°. The mol-ecular structure features two intra-molecular phenolic O-H⋯N hydrogen bonds with graph-set motif S(6). In the crystal, mol-ecules are connected via O-H⋯O hydrogen bonds into zigzag chains running along the a-axis direction.

Related literature

For related structures, see: Rivera et al. (2012 ▶), Zhang et al. (2012 ▶). For the synthesis, see: Rivera et al. (2013 ▶). 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

C28H42N2O5·H2O

M = 504.65

Orthorhombic,

a = 8.2629 (5) Å

b = 33.093 (3) Å

c = 10.0877 (6) Å

V = 2758.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.25 × 0.23 × 0.16 mm

Data collection

STOE IPDS II two-circle-diffractometer

Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001 ▶) T min = 0.975, T max = 0.982

22328 measured reflections

2464 independent reflections

2228 reflections with I > 2σ(I)

R int = 0.109

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.140

S = 1.17

2464 reflections

179 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.31 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA (Stoe & Cie, 2001 ▶); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL2013.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814010769/sj5401sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010769/sj5401Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814010769/sj5401Isup3.cml

CCDC reference: 1002201

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

C28H42N2O5·H2O	Dx = 1.215 Mg m−3
Mr = 504.65	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 25046 reflections
a = 8.2629 (5) Å	θ = 1.9–26.5°
b = 33.093 (3) Å	µ = 0.09 mm−1
c = 10.0877 (6) Å	T = 173 K
V = 2758.4 (3) Å3	Block, colourless
Z = 4	0.25 × 0.23 × 0.16 mm
F(000) = 1096

STOE IPDS II two-circle-diffractometer	2228 reflections with I > 2σ(I)
ω scans	Rint = 0.109
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	θmax = 25.0°, θmin = 2.1°
Tmin = 0.975, Tmax = 0.982	h = −9→9
22328 measured reflections	k = −38→39
2464 independent reflections	l = −11→12

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.075	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.0336P)2 + 2.7349P] where P = (Fo2 + 2Fc2)/3
S = 1.17	(Δ/σ)max = 0.009
2464 reflections	Δρmax = 0.26 e Å−3
179 parameters	Δρmin = −0.31 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	Occ. (<1)
O1	0.4835 (2)	0.17942 (5)	0.52432 (17)	0.0322 (4)
H1	0.405 (4)	0.1990 (10)	0.546 (3)	0.064 (10)*
O2	0.1840 (2)	0.03093 (5)	0.5809 (2)	0.0503 (6)
O3	−0.0101 (4)	0.2500	0.3032 (3)	0.0390 (10)	0.836 (8)
H3	−0.109 (8)	0.2500	0.338 (6)	0.059*	0.836 (8)
O3'	0.253 (2)	0.2500	0.3421 (19)	0.058 (6)*	0.164 (8)
H3'	0.2334	0.2500	0.2606	0.087*	0.164 (8)
N1	0.2068 (2)	0.21393 (5)	0.60143 (18)	0.0261 (4)
C1	0.1795 (4)	0.2500	0.6823 (3)	0.0264 (7)
H1A	0.2544	0.2500	0.7589	0.032*
H1B	0.0672	0.2500	0.7165	0.032*
C2	0.1058 (4)	0.2500	0.4066 (3)	0.0310 (7)
H2	0.2162	0.2500	0.3659	0.037*	0.836 (8)
H2'	0.0174	0.2500	0.3389	0.037*	0.164 (8)
C3	0.0894 (3)	0.21229 (6)	0.4924 (2)	0.0302 (5)
H3A	−0.0217	0.2106	0.5287	0.036*
H3B	0.1090	0.1879	0.4379	0.036*
C4	0.2008 (3)	0.17720 (6)	0.6846 (2)	0.0301 (5)
H4A	0.0874	0.1721	0.7114	0.036*
H4B	0.2649	0.1818	0.7662	0.036*
C5	0.2659 (3)	0.14019 (6)	0.6138 (2)	0.0267 (5)
C6	0.4081 (3)	0.14241 (6)	0.5402 (2)	0.0269 (5)
C7	0.4776 (3)	0.10750 (6)	0.4830 (2)	0.0272 (5)
C8	0.3949 (3)	0.07128 (7)	0.5020 (2)	0.0322 (5)
H8	0.4383	0.0472	0.4648	0.039*
C9	0.2515 (3)	0.06899 (7)	0.5731 (3)	0.0339 (6)
C10	0.1861 (3)	0.10328 (7)	0.6299 (2)	0.0301 (5)
H10	0.0884	0.1018	0.6793	0.036*
C11	0.6395 (3)	0.10903 (7)	0.4079 (2)	0.0302 (5)
C12	0.6259 (3)	0.13624 (8)	0.2851 (2)	0.0386 (6)
H12A	0.7300	0.1368	0.2385	0.058*
H12B	0.5970	0.1637	0.3126	0.058*
H12C	0.5422	0.1256	0.2258	0.058*
C13	0.7719 (3)	0.12506 (8)	0.5006 (2)	0.0375 (6)
H13A	0.8751	0.1261	0.4530	0.056*
H13B	0.7822	0.1071	0.5774	0.056*
H13C	0.7429	0.1523	0.5309	0.056*
C14	0.6927 (3)	0.06718 (8)	0.3597 (3)	0.0463 (7)
H14A	0.7957	0.0695	0.3122	0.070*
H14B	0.6102	0.0561	0.3001	0.070*
H14C	0.7062	0.0492	0.4360	0.070*
C15	0.0445 (4)	0.02625 (8)	0.6617 (4)	0.0574 (9)
H15A	0.0090	−0.0020	0.6594	0.086*
H15B	−0.0423	0.0437	0.6284	0.086*
H15C	0.0707	0.0339	0.7531	0.086*
O1W	−0.3119 (4)	0.2500	0.4322 (3)	0.0694 (9)
H1W	−0.3666	0.2706	0.4510	0.104*

	U11	U22	U33	U12	U13	U23
O1	0.0300 (9)	0.0264 (8)	0.0403 (9)	−0.0030 (7)	0.0049 (8)	0.0005 (7)
O2	0.0512 (12)	0.0248 (9)	0.0750 (14)	−0.0087 (8)	0.0206 (11)	−0.0029 (9)
O3	0.0355 (19)	0.0515 (19)	0.0301 (17)	0.000	−0.0060 (14)	0.000
N1	0.0302 (10)	0.0222 (9)	0.0261 (10)	0.0024 (7)	0.0019 (8)	−0.0003 (7)
C1	0.0272 (17)	0.0238 (15)	0.0281 (17)	0.000	0.0024 (14)	0.000
C2	0.0301 (18)	0.0344 (17)	0.0287 (17)	0.000	−0.0030 (15)	0.000
C3	0.0318 (13)	0.0288 (12)	0.0300 (12)	−0.0011 (9)	−0.0027 (10)	−0.0029 (9)
C4	0.0338 (13)	0.0271 (12)	0.0294 (12)	0.0022 (9)	0.0058 (10)	0.0028 (9)
C5	0.0265 (12)	0.0273 (11)	0.0261 (11)	0.0029 (9)	−0.0001 (9)	0.0029 (9)
C6	0.0253 (11)	0.0270 (11)	0.0283 (12)	−0.0008 (9)	−0.0029 (10)	0.0025 (9)
C7	0.0253 (12)	0.0298 (11)	0.0263 (11)	0.0029 (9)	−0.0035 (10)	0.0002 (9)
C8	0.0352 (13)	0.0258 (11)	0.0356 (13)	0.0035 (9)	0.0011 (11)	−0.0018 (9)
C9	0.0360 (13)	0.0234 (11)	0.0421 (14)	−0.0026 (10)	−0.0004 (12)	0.0026 (10)
C10	0.0265 (12)	0.0300 (12)	0.0337 (13)	0.0000 (9)	0.0027 (10)	0.0044 (9)
C11	0.0269 (12)	0.0349 (12)	0.0290 (12)	0.0031 (10)	0.0010 (10)	−0.0020 (10)
C12	0.0331 (14)	0.0535 (15)	0.0292 (13)	0.0014 (11)	0.0031 (11)	0.0023 (11)
C13	0.0243 (12)	0.0557 (15)	0.0324 (13)	0.0027 (11)	−0.0006 (10)	−0.0006 (11)
C14	0.0408 (16)	0.0419 (14)	0.0563 (17)	0.0058 (12)	0.0137 (14)	−0.0075 (13)
C15	0.0542 (18)	0.0335 (14)	0.085 (2)	−0.0102 (13)	0.0229 (17)	0.0044 (14)
O1W	0.0420 (18)	0.096 (3)	0.070 (2)	0.000	0.0107 (17)	0.000

O1—C6	1.383 (3)	C5—C10	1.397 (3)
O1—H1	0.94 (3)	C6—C7	1.413 (3)
O2—C9	1.380 (3)	C7—C8	1.393 (3)
O2—C15	1.420 (3)	C7—C11	1.538 (3)
O3—C2	1.417 (4)	C8—C9	1.388 (3)
O3—H3	0.89 (6)	C8—H8	0.9500
O3'—C2	1.378 (19)	C9—C10	1.381 (3)
O3'—H3'	0.8375	C10—H10	0.9500
N1—C1	1.463 (2)	C11—C14	1.532 (3)
N1—C3	1.468 (3)	C11—C13	1.534 (3)
N1—C4	1.478 (3)	C11—C12	1.536 (3)
C1—N1i	1.463 (2)	C12—H12A	0.9800
C1—H1A	0.9900	C12—H12B	0.9800
C1—H1B	0.9900	C12—H12C	0.9800
C2—C3i	1.525 (3)	C13—H13A	0.9800
C2—C3	1.525 (3)	C13—H13B	0.9800
C2—H2	1.0000	C13—H13C	0.9800
C2—H2'	1.0000	C14—H14A	0.9800
C3—H3A	0.9900	C14—H14B	0.9800
C3—H3B	0.9900	C14—H14C	0.9800
C4—C5	1.516 (3)	C15—H15A	0.9800
C4—H4A	0.9900	C15—H15B	0.9800
C4—H4B	0.9900	C15—H15C	0.9800
C5—C6	1.392 (3)	O1W—H1W	0.8401
C6—O1—H1	106 (2)	C8—C7—C6	116.6 (2)
C9—O2—C15	117.4 (2)	C8—C7—C11	121.5 (2)
C2—O3—H3	109 (4)	C6—C7—C11	121.83 (19)
C2—O3'—H3'	107.1	C9—C8—C7	122.5 (2)
C1—N1—C3	110.24 (19)	C9—C8—H8	118.8
C1—N1—C4	110.44 (18)	C7—C8—H8	118.8
C3—N1—C4	111.89 (17)	O2—C9—C10	124.6 (2)
N1—C1—N1i	109.3 (2)	O2—C9—C8	115.1 (2)
N1—C1—H1A	109.8	C10—C9—C8	120.2 (2)
N1i—C1—H1A	109.8	C9—C10—C5	119.0 (2)
N1—C1—H1B	109.8	C9—C10—H10	120.5
N1i—C1—H1B	109.8	C5—C10—H10	120.5
H1A—C1—H1B	108.3	C14—C11—C13	107.6 (2)
O3'—C2—C3i	110.3 (4)	C14—C11—C12	107.2 (2)
O3—C2—C3i	110.95 (19)	C13—C11—C12	110.0 (2)
O3'—C2—C3	110.3 (4)	C14—C11—C7	112.09 (19)
O3—C2—C3	110.95 (19)	C13—C11—C7	109.33 (19)
C3i—C2—C3	109.9 (3)	C12—C11—C7	110.68 (19)
O3—C2—H2	108.3	C11—C12—H12A	109.5
C3i—C2—H2	108.3	C11—C12—H12B	109.5
C3—C2—H2	108.3	H12A—C12—H12B	109.5
O3'—C2—H2'	108.8	C11—C12—H12C	109.5
C3i—C2—H2'	108.8	H12A—C12—H12C	109.5
C3—C2—H2'	108.8	H12B—C12—H12C	109.5
N1—C3—C2	109.6 (2)	C11—C13—H13A	109.5
N1—C3—H3A	109.7	C11—C13—H13B	109.5
C2—C3—H3A	109.7	H13A—C13—H13B	109.5
N1—C3—H3B	109.7	C11—C13—H13C	109.5
C2—C3—H3B	109.7	H13A—C13—H13C	109.5
H3A—C3—H3B	108.2	H13B—C13—H13C	109.5
N1—C4—C5	112.64 (18)	C11—C14—H14A	109.5
N1—C4—H4A	109.1	C11—C14—H14B	109.5
C5—C4—H4A	109.1	H14A—C14—H14B	109.5
N1—C4—H4B	109.1	C11—C14—H14C	109.5
C5—C4—H4B	109.1	H14A—C14—H14C	109.5
H4A—C4—H4B	107.8	H14B—C14—H14C	109.5
C6—C5—C10	120.4 (2)	O2—C15—H15A	109.5
C6—C5—C4	120.53 (19)	O2—C15—H15B	109.5
C10—C5—C4	118.9 (2)	H15A—C15—H15B	109.5
O1—C6—C5	119.23 (19)	O2—C15—H15C	109.5
O1—C6—C7	119.6 (2)	H15A—C15—H15C	109.5
C5—C6—C7	121.2 (2)	H15B—C15—H15C	109.5
C3—N1—C1—N1i	−63.1 (3)	C5—C6—C7—C11	−176.6 (2)
C4—N1—C1—N1i	172.70 (17)	C6—C7—C8—C9	0.0 (3)
C1—N1—C3—C2	59.1 (3)	C11—C7—C8—C9	177.8 (2)
C4—N1—C3—C2	−177.6 (2)	C15—O2—C9—C10	−5.2 (4)
O3'—C2—C3—N1	67.0 (8)	C15—O2—C9—C8	174.9 (2)
O3—C2—C3—N1	−177.8 (2)	C7—C8—C9—O2	179.1 (2)
C3i—C2—C3—N1	−54.8 (3)	C7—C8—C9—C10	−0.9 (4)
C1—N1—C4—C5	−166.7 (2)	O2—C9—C10—C5	−179.5 (2)
C3—N1—C4—C5	70.1 (2)	C8—C9—C10—C5	0.5 (4)
N1—C4—C5—C6	44.2 (3)	C6—C5—C10—C9	0.7 (3)
N1—C4—C5—C10	−139.5 (2)	C4—C5—C10—C9	−175.5 (2)
C10—C5—C6—O1	179.2 (2)	C8—C7—C11—C14	0.1 (3)
C4—C5—C6—O1	−4.6 (3)	C6—C7—C11—C14	177.9 (2)
C10—C5—C6—C7	−1.7 (3)	C8—C7—C11—C13	−119.1 (2)
C4—C5—C6—C7	174.6 (2)	C6—C7—C11—C13	58.7 (3)
O1—C6—C7—C8	−179.5 (2)	C8—C7—C11—C12	119.7 (2)
C5—C6—C7—C8	1.3 (3)	C6—C7—C11—C12	−62.6 (3)
O1—C6—C7—C11	2.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.94 (3)	1.80 (3)	2.671 (2)	153 (3)
O3—H3···O1W	0.89 (6)	1.93 (6)	2.813 (4)	174 (5)
O1W—H1W···O1ii	0.84	2.19	3.029 (2)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.94 (3)	1.80 (3)	2.671 (2)	153 (3)
O3—H3⋯O1W	0.89 (6)	1.93 (6)	2.813 (4)	174 (5)
O1W—H1W⋯O1i	0.84	2.19	3.029 (2)	173

Symmetry code: (i) .