1,3-Bis(3-tert-butyl-2-hy­droxy-5-meth­oxy­benz­yl)hexa­hydro­pyrimidin-5-ol monohydrate

Rivera, A.; Miranda-Carvajal, I.; Osorio, H.J.; Ríos-Motta, J.; Bolte, M.

doi:10.1107/S1600536814010769

organic compounds

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Pages o687-o688

doi:10.1107/S1600536814010769

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1,3-Bis(3-tert-butyl-2-hydroxy-5-methoxybenzyl)hexahydropyrimidin-5-ol monohydrate

Augusto Rivera,^a ^* Ingrid Miranda-Carvajal,^a Héctor Jairo Osorio,^b Jaime Ríos-Motta ^a and Michael Bolte ^c

^aUniversidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Cra 30 No. 45-03, Bogotá, Código Postal 111321, Colombia, ^bUniversidad Nacional de Colombia, Sede Manizales, Colombia, and ^cInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Str. 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: ariverau@unal.edu.co

Edited by J. Simpson, University of Otago, New Zealand (Received 8 May 2014; accepted 10 May 2014; online 21 May 2014)

The asymmetric unit of the title compound, C₂₈H₄₂N₂O₅·H₂O, consists of one half of the organic molecule and one half-molecule 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-hydroxybenzyl 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 molecular structure features two intramolecular phenolic O—H⋯N hydrogen bonds with graph-set motif S(6). In the crystal, molecules are connected via O—H⋯O hydrogen bonds into zigzag chains running along the a-axis direction.

CCDC reference: 1002201

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_r = 504.65
Orthorhombic, P n m a
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[F² > 2σ(F²)] = 0.075
wR(F²) = 0.140
S = 1.17
2464 reflections
179 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.31 e Å⁻³

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) $[x-1, -y+{\script{1\over 2}}, z]$ .

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.

Supporting information

CCDC reference: 1002201

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814010769/sj5401sup1.cif

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

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

checkCIF report

Comment top

Recently our group reported a protocol for the synthesis of a series of 2,2'-(dihydropyrimidine-1,3(2H,4H)-diyldimethanediyl)diphenols via a Mannich-type reaction (Rivera et al., 2013). As an extension of these studies, in this paper we describe the synthesis and crystal structure of the title compound, 1,3-bis(3-tert-butyl-2-hydroxy-5-methoxybenzyl)hexahydropyrimidin-5-ol, C₂₈H₄₂N₂O₅, as a monohydrate. The molecular structure and atom-numbering scheme for the title compound are shown in Fig. 1. The asymmetric unit contains one half-organic molecule and one half water molecule, which are both located on a mirror plane which passes through the central C atoms and the hydroxyl group of the heterocyclic system. In Fig. 1, atoms without labels were generated by the symmetry operator x, 1/2 - y, z. The 1,3-diazinane ring of the title compound adopts a chair conformation with a diequatorial substitution with puckering parameters Q, θ and ϕ of 0.594 (2) Å, 2.23 (19)°, 60 (4)° (Cremer & Pople, 1975). The aromatic rings make dihedral angles of 75.57 (9)° with the mean plane of the heterocyclic ring. The benzyl groups are located in a 1,3-diequatorial syn arrangement in the heterocyclic ring with a dihedral angle between the planes containing the aromatic rings of 19.18 (10)°. In the molecule of the title compound (Fig. 1), bond lengths (Allen et al., 1987) and angles are normal and comparable to those observed in related structures namely 4,4',6,6'-tetra-tert-butyl-2,2'- [1,3-diazinane-1,3-diylbis(methylene)]diphenol 0.25-hydrate (Zhang et al., 2012) and 6,6'-di-tert-butyl-4,4'-dimethoxy-2,2'- [1,3-diazinane-1,3-diylbis(methylene)]- diphenol 0.19-hydrate (Rivera et al., 2012). The crystal structure shows two intramolecular O—H···N(1,3-diazinane) hydrogen bonds with graph-set motif S(6) (Bernstein et al., 1995) (Table 1), where the N···O distance [N1···O1, 2.671 (2) Å] is shorter in comparison with the values observed in the related structure (Zhang et al. 2012). In contrast to the 4',6'-di-tert-butyl analog, the title compound was found to be more similar to the other related structure (Rivera et al., 2012), indicating that the methoxy substituent slightly influences the strength of the intermolecular hydrogen bonds in these compounds. In the crystal, hydroxyl groups of the 1,3-diazinane ring are linked to water molecules via O—H···O hydrogen bonds, leading to a two-molecule aggregate where the water-O accepts these interactions. These are linked into a zigzag chain along the a axis via O—H···O interactions between the water molecules and the phenolic-O atoms. (Fig. 2 and Table 1).

Related literature top

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 top

The title compound was prepared as follows: In a 50 ml round bottom flask equipped with a magnetic stir bar, 1 equiv. of 1,3-diamino-2-propanol, 3 equiv. of paraformaldehyde, and 2 equiv. of 2-tert-butyl-4-methoxyphenol were combined with 15 ml of methanol. Upon completion of the addition, the reaction mixture was stirred under reflux for 36 h. Then the reflux was stopped, the solvent was removed on a rotary evaporator under vacuum and the residue obtained (Anal. calcd. for C₂₈H₄₂N₂O₅: C 69.14%; H 8.64%; N 5.76%, O 16.46% found C 69.50%; H 8.66%; N 5.77%) was recrystallized from methanol to provide high quality crystals of the title compound (Yield 30.6%. M.p. = 393 K).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are drawn as dashed lines. Only one of the two sites of the disordered hydroxyl group is shown. Symmetry operator for generating equivalent atoms. x, 1/2 - y, z.
	Fig. 2. Partial packing diagram of the title compound. The bonds of the second hydroxyl group site (on the left) are drawn with open bonds. Hydrogen bonds involving the two different sites of the disordered hydroxy groups are drawn with full (right hand side) or open dashed (left hand side) bonds.

1,3-Bis(3-tert-butyl-2-hydroxy-5-methoxybenzyl)hexahydropyrimidin-5-ol monohydrate top

Crystal data top

C₂₈H₄₂N₂O₅·H₂O	D_x = 1.215 Mg m⁻³
M_r = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0336P)² + 2.7349P] where P = (F_o² + 2F_c²)/3
S = 1.17	(Δ/σ)_max = 0.009
2464 reflections	Δρ_max = 0.26 e Å⁻³
179 parameters	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₈H₄₂N₂O₅·H₂O	V = 2758.4 (3) Å³
M_r = 504.65	Z = 4
Orthorhombic, Pnma	Mo Kα radiation
a = 8.2629 (5) Å	µ = 0.09 mm⁻¹
b = 33.093 (3) Å	T = 173 K
c = 10.0877 (6) Å	0.25 × 0.23 × 0.16 mm

Data collection top

STOE IPDS II two-circle- diffractometer	2464 independent reflections
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	2228 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.982	R_int = 0.109
22328 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	0 restraints
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	Δρ_max = 0.26 e Å⁻³
2464 reflections	Δρ_min = −0.31 e Å⁻³
179 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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

Geometric parameters (Å, º) top

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)

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (ii) x−1, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

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)	172.6

Symmetry code: (i) x−1, −y+1/2, z.

Acknowledgements

We acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB) de la Universidad Nacional de Colombia, for financial support of this work.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Rivera, A., González, D. M., Ríos-Motta, J., Fejfarová, K. & Dušek, M. (2012). Acta Cryst. E68, o191–o192. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Rivera, A., Ríos-Motta, J., Trujillo, G. P., González, D. M. & Alcázar, D. (2013). Synth. Commun. 43, 791–799. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar
Zhang, M., Li, L., Yuan, F. & Qian, H. (2012). Acta Cryst. E68, o2123. CSD CrossRef IUCr Journals Google Scholar

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Volume 70| Part 6| June 2014| Pages o687-o688

doi:10.1107/S1600536814010769

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1,3-Bis(3-tert-butyl-2-hy­dr­oxy-5-meth­­oxy­benz­yl)hexa­hydro­pyrimidin-5-ol monohydrate

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organic compounds

1,3-Bis(3-tert-butyl-2-hydroxy-5-methoxybenzyl)hexahydropyrimidin-5-ol monohydrate