6,6′-Di-tert-butyl-4,4′-dimeth­oxy-2,2′-[1,3-diazinane-1,3-diylbis(methyl­ene)]diphenol 0.19-hydrate

Rivera, A.; González, D.M.; Ríos-Motta, J.; Fejfarová, K.; Dušek, M.

doi:10.1107/S1600536811053542

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Pages o191-o192

doi:10.1107/S1600536811053542

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6,6′-Di-tert-butyl-4,4′-dimethoxy-2,2′-[1,3-diazinane-1,3-diylbis(methylene)]diphenol 0.19-hydrate

Augusto Rivera,^a ^* Derly Marcela González,^a Jaime Ríos-Motta,^a Karla Fejfarová ^b and Michal Dušek ^b

^aDepartamento de Química, Universidad Nacional de Colombia, Ciudad Universitaria, Bogotá, Colombia, and ^bInstitute of Physics ASCR, v.v.i., Na Slovance 2, 182 21 Praha 8, Czech Republic
^*Correspondence e-mail: ariverau@unal.edu.co

(Received 7 December 2011; accepted 12 December 2011; online 21 December 2011)

In the title hexahydropyrimidine derivative, C₂₈H₄₂N₂O₄·0.19H₂O, the 1,3-diazinane ring has a chair conformation with a diequatorial substitution. The asymmetric unit contains one half-organic molecule and a solvent water molecule with occupany 0.095. The molecule 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 molecule is also located on this mirror plane. The dihedral angle between the planes of the aromatic rings is 17.71 (3)°. Two intramolecular O—H⋯N hydrogen bonds with graph-set motif S(6) are present. No remarkable intermolecular 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_r = 473.5
Orthorhombic, P n m a
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[F² > 2σ(F²)] = 0.035
wR(F²) = 0.122
S = 2.64
2456 reflections
164 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811053542/go2039sup1.cif

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

checkCIF report

Comment top

The asymmetric unit (Fig. 1), contains a one symmetry independent half molecule of 2,2'-(dihydropyrimidine-1,3(2H,4H)-diyldimethanediyl)bis(6-tertbutyl-4-methoxyphenol) and a solvent water molecule with occupany 0.095. The molecule lies on a mirror plane perpendicular to [0,1,0] which passes through the central C atom of the heterocyclic system. In Fig. 1 primed atoms were positioned on the other half of the molecules and had symmetry codes (x, 1/2 - y, z). The hexahydropyrimidine ring of the title compound adopts a chair conformation with a diequatorial substitution (Cremer & Pople, 1975) with puckering parameters Q, θ and ϕ of 0.5891 (10) Å, 3.01 (11)°, 60.0 (18)°. In the molecule of the title compound (Fig. 1), bond lengths (Allen et al., 1987) and angles are normal and comparable to the related structure namely 2,2'-(dihydropyrimidine-1,3(2H,4H)-diyldimethanediyl)bis (6-methylphenol) whose crystallographic data have been deposited at the Cambridge Crystallographic Data Center. The CCDC deposition number is 854735 (Rivera et al.,2012a). However a careful comparison with the values of the corresponding angles and bond distances in the related structure (Rivera, et al. 2012a), indicated that the O1—C6—C7 angle increase by 1.82°. The crystal structure of the title confirms the presence of two O—H···N(1,3-diazinane) hydrogen bond with graph-set motif S(6) (Bernstein et al. 1995) (Table 1). The N···O distance [N1···O1, 2.6735 (10) Å] is shorter in comparison with the values observed in related structure (Rivera, et al. 2012a), showing a slightly increase in hydrogen-bonding strength.

The most obvious difference between the title compound and the related structure (Rivera, et al. 2012a) is the presence of mirror symmetry in the solid state with molecules bisected by mirror planes (the C1 and C2 atoms of the 1,3-diazinane ring lie on the mirror plane). The partially occupied water molecule also is located on this mirror plane. Another important difference is observed in the dihedral angle between the phenyl rings, which is -17.711 (30)° for the title compound and 58.431 (38)° for related structure (Rivera, et al. 2012a). The deviation of the dihedral angle in (I) is probably due to repulsive interactions between the tert-butyl groups.

Fig 2. shows the crystal packing with channels extended along the [1,0,1] axis and accommodating the water molecules. Each channel is composed of two symmetry equivalent positions of the organic molecule. No remarkable intermolecular contacts exist in the presented structure.

Related literature top

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 top

The title compound was obtained according to our recently reported methodology (Rivera et al., 2012b), that is, to a stirred solution of 2-tert-butyl-4-methoxy-phenol (2.0 mmol) in 96% ethanol (5 ml) heated under reflux, was added slowly a solution of 1,3,7,9,13,15,19,21-octaazapentacyclo[19.3.1.^13,7.1^9,13.1^15,19]octacosane prepared according to a previous report (Rivera et al., 2010) (200 mg, 0.54 mmol) in 96% ethanol (5 ml). Upon completion of the addition, the reaction mixture was stirred under reflux for 60 h. Then the reflux was stopped, the solvent was removed on a rotary evaporator under vacuum and the residue obtained was chromatographed on silica gel eluting with benzene/AcOEt (gradient elution with 5% to 20% AcOEt) to afford a solid which was recrystallized in 96% ethanol to provide high quality crystals of the title compound (I), (Yield 27.0%, m.p. 403–404 K).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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 (Petříček et al., 2006).

Figures top

	Fig. 1. A view of (I) with the numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The packing of (I), viewed along the [1,0,1] axis.

6,6'-Di-tert-butyl-4,4'-dimethoxy-2,2'-[1,3-diazinane-1,3- diylbis(methylene)]diphenol 0.19-hydrate top

Crystal data top

C₂₈H₄₂N₂O₄·0.19H₂O	F(000) = 1029.6
M_r = 473.5	D_x = 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

Data collection top

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 monochromator	R_int = 0.027
Detector resolution: 10.3784 pixels mm^-1	θ_max = 67.1°, θ_min = 4.6°
Rotation method data acquisition using ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −39→39
T_min = 0.073, T_max = 1	l = −11→11
54017 measured reflections

Refinement top

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	Δρ_max = 0.17 e Å⁻³
164 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints

Crystal data top

C₂₈H₄₂N₂O₄·0.19H₂O	V = 2724.34 (14) Å³
M_r = 473.5	Z = 4
Orthorhombic, Pnma	Cu Kα radiation
a = 8.2265 (1) Å	µ = 0.61 mm⁻¹
b = 33.0103 (2) Å	T = 120 K
c = 10.0322 (5) Å	0.42 × 0.36 × 0.30 mm

Data collection top

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	2456 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2353 reflections with I > 3σ(I)
T_min = 0.073, T_max = 1	R_int = 0.027
54017 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 2.64	Δρ_max = 0.17 e Å⁻³
2456 reflections	Δρ_min = −0.14 e Å⁻³
164 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

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	0.890 (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

Experimental details

Crystal data
Chemical formula	C₂₈H₄₂N₂O₄·0.19H₂O
M_r	473.5
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	120
a, b, c (Å)	8.2265 (1), 33.0103 (2), 10.0322 (5)
V (Å³)	2724.34 (14)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.61
Crystal size (mm)	0.42 × 0.36 × 0.30

Data collection
Diffractometer	Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.073, 1
No. of measured, independent and observed [I > 3σ(I)] reflections	54017, 2456, 2353
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.122, 2.64
No. of reflections	2456
No. of parameters	164
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.14

Computer programs: CrysAlis PRO (Agilent, 2010), SIR2002 (Burla et al., 2003), JANA2006 (Petříček et al., 2006), DIAMOND (Brandenburg & Putz, 2005).

Hydrogen-bond geometry (Å, º) top

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)

Acknowledgements

We acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB) de la Universidad Nacional de Colombia, for financial support of this work, as well as the Institutional research plan No. AVOZ10100521 of the Institute of Physics and the project Praemium Academiae of the Academy of Sciences of the Czech Republic. DMG acknowledges the Vicerrectoría Académica de la Universidad Nacional de Colombia for a fellowship.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
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
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact, Bonn, Germany. Google Scholar
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103. CrossRef IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Petříček, V., Dušek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Prague, Czech Republic. Google Scholar
Rivera, A., Gonzalez, D. M., Ríos-Motta, J., Fejfarova, K. & Dušek, M. (2012a). J. Chem. Crystallogr. In preparation. Google Scholar
Rivera, A., Ríos-Motta, J., Dušek, M. & Jarošová, M. (2010). Acta Cryst. C66, o222–o224. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rivera, A., Ríos-Motta, J., Trujillo, G. P., González, D. M. & Alcázar, D. (2012b). Synth. Commun. Accepted. (Reference code: ID LSYC-2011-6173). Google Scholar

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Volume 68| Part 1| January 2012| Pages o191-o192

doi:10.1107/S1600536811053542

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

6,6′-Di-tert-butyl-4,4′-dimeth­­oxy-2,2′-[1,3-diazinane-1,3-diylbis(methyl­ene)]diphenol 0.19-hydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

6,6′-Di-tert-butyl-4,4′-dimethoxy-2,2′-[1,3-diazinane-1,3-diylbis(methylene)]diphenol 0.19-hydrate