4-{[3-(4-Hydroxy­benzyl­ideneamino)-2,2-dimethyl­propyl]iminiomethyl}phenolate dihydrate

Kia, R.; Fun, H.-K.; Kargar, H.

doi:10.1107/S1600536809013804

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Pages o1071-o1072

doi:10.1107/S1600536809013804

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4-{[3-(4-Hydroxybenzylideneamino)-2,2-dimethylpropyl]iminiomethyl}phenolate dihydrate

Reza Kia,^a ‡ Hoong-Kun Fun ^a ^*§ and Hadi Kargar ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran
^*Correspondence e-mail: hkfun@usm.my

(Received 10 April 2009; accepted 13 April 2009; online 18 April 2009)

The asymmetric unit of the title compound, C₁₉H₂₂N₂O₂·2H₂O, comprises a zwitterionic form of the Schiff base compound and two water molecules of crystallization. Intermolecular N—H⋯O, C—H⋯O and O—H⋯N hydrogen bonds involving one of the water molecules in the asymmetric unit generate seven- and eight-membered rings, with R₂¹(7) and R₂²(8) ring motifs, respectively. The dihedral angle beween the two aromatic rings is 86.5 (2)°. The imino and iminium groups are coplanar with the benzene rings to which they are attached, making dihedral angles (N—C—C—C) of −179.3 (5) and −179.2 (4)°, respectively. Validation software indicates the higher symmetry space group Pnma for this structure. However, this process ignores H atoms and the zwitterionic configuration of the main molecule breaks the higher symmetry. Solution in Pna2₁ provides a chemically sensible zwitterionic compound with improved residuals. In the crystal structure, molecules are linked together through intermolecular O—H⋯O, O—H⋯N, N—H⋯O and C—H⋯O interactions, forming a three-dimensional network. The crystal structure is further stabilized by intermolecular C—H⋯π interactions.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For information on Schiff base ligands and their complexes and applications, see: Calligaris & Randaccio (1987 ); Li et al. (2005 ); Bomfim et al. (2005 ); Glidewell et al. (2005 , 2006 ); Sun et al. (2004 ). For details of the synthesis, see: Fun et al. (2008 ). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₉H₂₂N₂O₂·2H₂O
M_r = 346.42
Orthorhombic, P n a 2₁
a = 13.0336 (4) Å
b = 11.5242 (3) Å
c = 12.4132 (4) Å
V = 1864.49 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.34 × 0.21 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.971, T_max = 0.991
10183 measured reflections
2237 independent reflections
1753 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.116
S = 1.05
2237 reflections
235 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C12–C17 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O1ⁱ	0.93	1.91	2.830 (5)	171
O1W—H2W1⋯O2ⁱⁱ	0.86	1.90	2.751 (4)	168
O2W—H1W2⋯O1Wⁱⁱⁱ	0.84	2.00	2.774 (3)	153
O2W—H2W2⋯N1	0.86	2.22	2.826 (4)	127
N2—H1N2⋯O2W	0.95 (4)	1.90 (4)	2.832 (4)	170 (3)
O1—H1O1⋯O2ⁱⁱ	0.83 (4)	1.74 (5)	2.565 (5)	174 (5)
C17—H17A⋯O2W	0.93	2.52	3.408 (6)	161
C10—H10B⋯Cg1^iv	0.97	2.69	3.422 (5)	133
C8—H8A⋯Cg2^v	0.97	2.74	3.497 (5)	136
Symmetry codes: (i) $[-x, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[-x, -y+1, z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (iv) $[-x+1, -y+1, z-{\script{1\over 2}}]$ ; (v) $[-x+1, -y+1, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013804/sj2615sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809013804/sj2615Isup2.hkl

checkCIF report

Comment top

In the field of coordination chemistry, Schiff base compounds are among the most prevalent and versatile ligands. They have received much attention due to their important roles in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism, and supramolecular architectures. In comparison to the Schiff base metal complexes, only a relatively small number of free Schiff base ligands have been structurally characterized (Calligaris & Randaccio, 1987). Structures of Schiff bases derived from substituted benzaldehydes have been reported (Li et al., 2005; Bomfim et al., 2005; Glidewell et al., 2005, 2006; Sun et al., 2004).

The asymmetric unit of the title compound, Fig. 1, comprises a zwitterionic Schiff base compound and two water molecules of crystallization. The zwitterion results from protonation of the imine N2 atom with the O2 hydroxy group deprotonated resulting in the formation of iminium and phenolate groups. Intermolecular N—H···O and C—H···O hydrogen bonds involving the O2W O atom as a bifurcated acceptor generate an R₂¹(7) ring motif (Bernstein et al., 1995). Intermolecular N—H···O and O—H···N hydrogen bonds, again involving O2W, generate an R₂²(8) ring motif. The dihedral angle beween the two phenyl rings is 86.5 (2)°. The imino and iminium groups are coplanar with the benzene rings to which they are attached making dihedral angles of -179.3 (5) and -179.2 (4)° for N1—C7—C6—C5 and N2—C11—C12—C13, respectively. This structure requires differentiating between the Pna21 and Pnma space groups to achieve a correct solution. The solution based on the higher symmetry space group (Pnma) gives a chemically nonsensible polymeric chain as the program PLATON/ADDSYM has not taken into account H atoms in determining the symmetry elements. The solution in Pna21 gives a chemically sensible zwitterionic compound with lower R values. In the crystal structure, the molecules are linked together through intermolecular O—H···O, O—H···N, N—H···O and C—H···O interactions, forming a three-dimensional network (Fig. 2). The crystal structure is further stabilized by intermolecular C—H···π interactions [Cg1 and Cg2 are the centroids of the C1–C6 and C12–C17 benzene rings] (Table 1).

Related literature top

For hydrogen-bond motifs, see: Bernstein et al. (1995). For information on Schiff base ligands and their complexes and applications, see: Calligaris & Randaccio (1987); Li et al. (2005); Bomfim et al. (2005); Glidewell et al. (2005, 2006); Sun et al. (2004). For details of the synthesis, see: Fun et al. (2008). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986).

Experimental top

The synthetic method has been described earlier (Fun et al., 2008), except that 4-hydroxybenzaldehyde (2 mmol, 244 mg) and 2,2-dimethylpropane diamine (1 mmol, 102 mg) were used. Single crystals suitable for X-ray diffraction were obtained by evaporation of an ethanol solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with atom labels and 50% probability ellipsoids for non-H atoms. Intermolecular interactions involving the O2W water molecule are shown as dashed lines.
	Fig. 2. The crystal packing of the title compound, viewed down the a axis showing three-dimensional network formation through intermolecular interactions, shown as dashed lines.

4-{[3-(4-Hydroxybenzylideneamino)-2,2-dimethylpropyl]iminiomethyl}phenolate dihydrate top

Crystal data top

C₁₉H₂₂N₂O₂·2H₂O	F(000) = 744
M_r = 346.42	D_x = 1.234 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1477 reflections
a = 13.0336 (4) Å	θ = 2.4–29.9°
b = 11.5242 (3) Å	µ = 0.09 mm⁻¹
c = 12.4132 (4) Å	T = 100 K
V = 1864.49 (10) Å³	Block, orange
Z = 4	0.34 × 0.21 × 0.11 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2237 independent reflections
Radiation source: fine-focus sealed tube	1753 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −15→16
T_min = 0.971, T_max = 0.991	k = −14→14
10183 measured reflections	l = −16→7

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0526P)² + 0.5548P] where P = (F_o² + 2F_c²)/3
2237 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.27 e Å⁻³
3 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₉H₂₂N₂O₂·2H₂O	V = 1864.49 (10) Å³
M_r = 346.42	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 13.0336 (4) Å	µ = 0.09 mm⁻¹
b = 11.5242 (3) Å	T = 100 K
c = 12.4132 (4) Å	0.34 × 0.21 × 0.11 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2237 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1753 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.991	R_int = 0.056
10183 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	3 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.27 e Å⁻³
2237 reflections	Δρ_min = −0.20 e Å⁻³
235 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

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

	x	y	z	U_iso*/U_eq
O1	0.0498 (3)	0.5696 (3)	1.0250 (3)	0.0254 (8)
O2	0.0475 (3)	0.5792 (3)	0.4102 (2)	0.0217 (7)
N1	0.5104 (3)	0.5803 (3)	0.8323 (3)	0.0192 (8)
N2	0.5136 (3)	0.5842 (3)	0.5796 (3)	0.0186 (8)
C1	0.2946 (4)	0.5328 (4)	0.8831 (4)	0.0181 (10)
H1A	0.3225	0.4895	0.8270	0.022*
C2	0.1925 (4)	0.5165 (4)	0.9112 (4)	0.0178 (10)
H2A	0.1528	0.4627	0.8741	0.021*
C3	0.1496 (4)	0.5802 (4)	0.9947 (4)	0.0184 (10)
C4	0.2104 (4)	0.6615 (4)	1.0498 (4)	0.0221 (10)
H4A	0.1828	0.7050	1.1059	0.026*
C5	0.3115 (4)	0.6764 (4)	1.0197 (4)	0.0211 (10)
H5A	0.3510	0.7310	1.0560	0.025*
C6	0.3563 (4)	0.6130 (4)	0.9374 (4)	0.0181 (10)
C7	0.4645 (4)	0.6339 (4)	0.9073 (4)	0.0186 (10)
H7A	0.5010	0.6896	0.9457	0.022*
C8	0.6178 (4)	0.6143 (4)	0.8131 (4)	0.0172 (9)
H8A	0.6594	0.5447	0.8092	0.021*
H8B	0.6416	0.6593	0.8742	0.021*
C9	0.63477 (18)	0.6854 (2)	0.7101 (5)	0.0166 (5)
C10	0.6196 (4)	0.6143 (4)	0.6059 (4)	0.0207 (10)
H10A	0.6481	0.6580	0.5463	0.025*
H10B	0.6588	0.5431	0.6122	0.025*
C11	0.4577 (4)	0.6396 (3)	0.5096 (3)	0.0173 (9)
H11A	0.4891	0.7009	0.4737	0.021*
C12	0.3548 (4)	0.6168 (4)	0.4823 (4)	0.0160 (9)
C13	0.3087 (4)	0.6874 (4)	0.4023 (4)	0.0186 (10)
H13A	0.3476	0.7432	0.3668	0.022*
C14	0.2061 (4)	0.6736 (4)	0.3767 (4)	0.0183 (9)
H14A	0.1768	0.7206	0.3241	0.022*
C15	0.1448 (4)	0.5894 (4)	0.4291 (4)	0.0172 (9)
C16	0.1949 (4)	0.5154 (3)	0.5056 (4)	0.0182 (10)
H16A	0.1574	0.4564	0.5382	0.022*
C17	0.2949 (4)	0.5287 (3)	0.5318 (4)	0.0181 (10)
H17A	0.3246	0.4798	0.5826	0.022*
C18	0.56782 (19)	0.7944 (2)	0.7087 (5)	0.0209 (6)
H18A	0.5770	0.8364	0.7748	0.031*
H18B	0.4971	0.7725	0.7014	0.031*
H18C	0.5873	0.8426	0.6491	0.031*
C19	0.74958 (18)	0.7180 (2)	0.7099 (6)	0.0230 (6)
H19A	0.7659	0.7590	0.7750	0.034*
H19B	0.7640	0.7666	0.6490	0.034*
H19C	0.7903	0.6487	0.7057	0.034*
O1W	0.02979 (14)	0.33777 (16)	0.7189 (3)	0.0223 (5)
H1W1	0.0021	0.3754	0.6592	0.033*
H2W1	0.0012	0.3713	0.7731	0.033*
O2W	0.45692 (15)	0.38775 (16)	0.7030 (3)	0.0247 (5)
H1W2	0.4922	0.3279	0.6916	0.037*
H2W2	0.4735	0.4056	0.7681	0.037*
H1N2	0.487 (3)	0.520 (3)	0.618 (3)	0.020 (9)*
H1O1	0.020 (3)	0.524 (4)	0.984 (4)	0.040 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0152 (16)	0.0329 (16)	0.0281 (17)	−0.0051 (14)	0.0031 (13)	−0.0086 (14)
O2	0.0171 (16)	0.0261 (15)	0.0219 (16)	−0.0001 (13)	−0.0042 (13)	0.0062 (12)
N1	0.020 (2)	0.0172 (18)	0.0207 (18)	−0.0025 (17)	0.0044 (15)	0.0045 (16)
N2	0.0145 (19)	0.0181 (18)	0.0231 (19)	−0.0025 (16)	0.0018 (15)	−0.0003 (15)
C1	0.019 (2)	0.019 (2)	0.016 (2)	0.001 (2)	0.0061 (19)	0.0063 (18)
C2	0.018 (3)	0.020 (2)	0.015 (2)	−0.0032 (19)	−0.0010 (19)	0.0004 (17)
C3	0.012 (2)	0.0189 (19)	0.025 (2)	−0.0004 (17)	0.0006 (17)	0.0025 (18)
C4	0.022 (2)	0.0227 (19)	0.022 (2)	0.0024 (19)	0.0011 (19)	−0.0022 (18)
C5	0.026 (3)	0.0182 (18)	0.019 (2)	−0.0060 (19)	−0.004 (2)	0.0028 (18)
C6	0.021 (2)	0.0139 (18)	0.019 (2)	0.0006 (19)	0.0014 (18)	0.0042 (19)
C7	0.0090 (19)	0.024 (2)	0.023 (2)	−0.0051 (17)	−0.0087 (18)	0.0076 (18)
C8	0.010 (2)	0.017 (2)	0.025 (2)	0.0022 (19)	−0.0017 (18)	0.004 (2)
C9	0.0150 (11)	0.0190 (11)	0.0157 (13)	−0.0035 (10)	0.002 (2)	−0.004 (2)
C10	0.021 (2)	0.025 (2)	0.016 (2)	−0.004 (2)	−0.0033 (19)	0.000 (2)
C11	0.029 (2)	0.0100 (16)	0.013 (2)	0.0029 (18)	−0.0015 (18)	−0.0009 (15)
C12	0.012 (2)	0.0166 (18)	0.020 (2)	0.0025 (18)	0.0026 (17)	−0.0080 (19)
C13	0.018 (2)	0.0142 (17)	0.024 (2)	−0.0012 (17)	0.0025 (19)	0.0039 (17)
C14	0.023 (2)	0.0161 (18)	0.016 (2)	0.0023 (18)	0.0008 (19)	0.0027 (17)
C15	0.021 (2)	0.0144 (16)	0.017 (2)	0.0029 (18)	−0.0014 (18)	−0.0027 (17)
C16	0.018 (3)	0.0117 (18)	0.025 (3)	0.0003 (18)	0.0044 (19)	0.0002 (18)
C17	0.021 (2)	0.0116 (17)	0.022 (2)	0.0041 (18)	0.0054 (19)	0.0051 (18)
C18	0.0220 (12)	0.0170 (12)	0.0238 (15)	−0.0011 (10)	−0.001 (3)	−0.006 (2)
C19	0.0181 (12)	0.0244 (13)	0.0265 (16)	−0.0061 (11)	0.002 (3)	0.001 (3)
O1W	0.0244 (10)	0.0209 (9)	0.0216 (13)	0.0046 (8)	−0.0003 (16)	−0.0010 (13)
O2W	0.0286 (11)	0.0201 (9)	0.0255 (14)	0.0002 (8)	−0.0010 (18)	−0.0041 (16)

Geometric parameters (Å, º) top

O1—C3	1.359 (6)	C9—C10	1.543 (7)
O1—H1O1	0.83 (4)	C10—H10A	0.9700
O2—C15	1.295 (6)	C10—H10B	0.9700
N1—C7	1.267 (6)	C11—C12	1.407 (7)
N1—C8	1.473 (6)	C11—H11A	0.9300
N2—C11	1.302 (6)	C12—C13	1.418 (6)
N2—C10	1.461 (6)	C12—C17	1.421 (6)
N2—H1N2	0.95 (4)	C13—C14	1.384 (8)
C1—C2	1.388 (7)	C13—H13A	0.9300
C1—C6	1.398 (7)	C14—C15	1.415 (7)
C1—H1A	0.9300	C14—H14A	0.9300
C2—C3	1.387 (6)	C15—C16	1.434 (6)
C2—H2A	0.9300	C16—C17	1.352 (7)
C3—C4	1.405 (7)	C16—H16A	0.9300
C4—C5	1.380 (8)	C17—H17A	0.9300
C4—H4A	0.9300	C18—H18A	0.9600
C5—C6	1.385 (7)	C18—H18B	0.9600
C5—H5A	0.9300	C18—H18C	0.9600
C6—C7	1.480 (6)	C19—H19A	0.9600
C7—H7A	0.9300	C19—H19B	0.9600
C8—C9	1.535 (7)	C19—H19C	0.9600
C8—H8A	0.9700	O1W—H1W1	0.9309
C8—H8B	0.9700	O1W—H2W1	0.8614
C9—C18	1.529 (3)	O2W—H1W2	0.8404
C9—C19	1.543 (3)	O2W—H2W2	0.8612

C3—O1—H1O1	110 (4)	C9—C10—H10A	108.3
C7—N1—C8	115.9 (4)	N2—C10—H10B	108.3
C11—N2—C10	124.2 (4)	C9—C10—H10B	108.3
C11—N2—H1N2	121 (2)	H10A—C10—H10B	107.4
C10—N2—H1N2	115 (2)	N2—C11—C12	127.0 (4)
C2—C1—C6	121.3 (4)	N2—C11—H11A	116.5
C2—C1—H1A	119.4	C12—C11—H11A	116.5
C6—C1—H1A	119.4	C11—C12—C13	117.7 (4)
C3—C2—C1	120.2 (4)	C11—C12—C17	123.6 (4)
C3—C2—H2A	119.9	C13—C12—C17	118.7 (4)
C1—C2—H2A	119.9	C14—C13—C12	120.3 (4)
O1—C3—C2	123.0 (4)	C14—C13—H13A	119.8
O1—C3—C4	117.7 (4)	C12—C13—H13A	119.8
C2—C3—C4	119.3 (4)	C13—C14—C15	121.3 (4)
C5—C4—C3	119.3 (5)	C13—C14—H14A	119.4
C5—C4—H4A	120.3	C15—C14—H14A	119.4
C3—C4—H4A	120.3	O2—C15—C14	122.1 (4)
C4—C5—C6	122.4 (4)	O2—C15—C16	120.8 (4)
C4—C5—H5A	118.8	C14—C15—C16	117.1 (4)
C6—C5—H5A	118.8	C17—C16—C15	122.0 (4)
C5—C6—C1	117.5 (4)	C17—C16—H16A	119.0
C5—C6—C7	120.1 (4)	C15—C16—H16A	119.0
C1—C6—C7	122.3 (4)	C16—C17—C12	120.5 (4)
N1—C7—C6	123.8 (4)	C16—C17—H17A	119.8
N1—C7—H7A	118.1	C12—C17—H17A	119.8
C6—C7—H7A	118.1	C9—C18—H18A	109.5
N1—C8—C9	114.5 (3)	C9—C18—H18B	109.5
N1—C8—H8A	108.6	H18A—C18—H18B	109.5
C9—C8—H8A	108.6	C9—C18—H18C	109.5
N1—C8—H8B	108.6	H18A—C18—H18C	109.5
C9—C8—H8B	108.6	H18B—C18—H18C	109.5
H8A—C8—H8B	107.6	C9—C19—H19A	109.5
C18—C9—C8	111.4 (4)	C9—C19—H19B	109.5
C18—C9—C19	110.7 (2)	H19A—C19—H19B	109.5
C8—C9—C19	105.7 (4)	C9—C19—H19C	109.5
C18—C9—C10	110.7 (4)	H19A—C19—H19C	109.5
C8—C9—C10	113.3 (2)	H19B—C19—H19C	109.5
C19—C9—C10	104.6 (4)	H1W1—O1W—H2W1	104.2
N2—C10—C9	115.8 (4)	H1W2—O2W—H2W2	102.5
N2—C10—H10A	108.3

C6—C1—C2—C3	−0.1 (7)	C11—N2—C10—C9	99.7 (5)
C1—C2—C3—O1	178.9 (4)	C18—C9—C10—N2	−53.5 (5)
C1—C2—C3—C4	0.4 (7)	C8—C9—C10—N2	72.5 (4)
O1—C3—C4—C5	−178.6 (4)	C19—C9—C10—N2	−172.8 (4)
C2—C3—C4—C5	0.0 (7)	C10—N2—C11—C12	−178.4 (4)
C3—C4—C5—C6	−0.7 (7)	N2—C11—C12—C13	−179.2 (4)
C4—C5—C6—C1	0.9 (7)	N2—C11—C12—C17	1.9 (7)
C4—C5—C6—C7	179.0 (4)	C11—C12—C13—C14	−176.2 (4)
C2—C1—C6—C5	−0.6 (7)	C17—C12—C13—C14	2.8 (7)
C2—C1—C6—C7	−178.6 (4)	C12—C13—C14—C15	−0.1 (7)
C8—N1—C7—C6	179.1 (4)	C13—C14—C15—O2	176.4 (4)
C5—C6—C7—N1	−179.3 (4)	C13—C14—C15—C16	−3.1 (7)
C1—C6—C7—N1	−1.3 (7)	O2—C15—C16—C17	−175.9 (5)
C7—N1—C8—C9	−106.9 (4)	C14—C15—C16—C17	3.6 (7)
N1—C8—C9—C18	56.0 (4)	C15—C16—C17—C12	−1.0 (7)
N1—C8—C9—C19	176.4 (4)	C11—C12—C17—C16	176.6 (4)
N1—C8—C9—C10	−69.6 (4)	C13—C12—C17—C16	−2.3 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O1ⁱ	0.93	1.91	2.830 (5)	171
O1W—H2W1···O2ⁱⁱ	0.86	1.90	2.751 (4)	168
O2W—H1W2···O1Wⁱⁱⁱ	0.84	2.00	2.774 (3)	153
O2W—H2W2···N1	0.86	2.22	2.826 (4)	127
N2—H1N2···O2W	0.95 (4)	1.90 (4)	2.832 (4)	170 (3)
O1—H1O1···O2ⁱⁱ	0.83 (4)	1.74 (5)	2.565 (5)	174 (5)
C17—H17A···O2W	0.93	2.52	3.408 (6)	161
C10—H10B···Cg1^iv	0.97	2.69	3.422 (5)	133
C8—H8A···Cg2^v	0.97	2.74	3.497 (5)	136

Symmetry codes: (i) −x, −y+1, z−1/2; (ii) −x, −y+1, z+1/2; (iii) x+1/2, −y+1/2, z; (iv) −x+1, −y+1, z−1/2; (v) −x+1, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₂N₂O₂·2H₂O
M_r	346.42
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	100
a, b, c (Å)	13.0336 (4), 11.5242 (3), 12.4132 (4)
V (Å³)	1864.49 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.34 × 0.21 × 0.11

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.971, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	10183, 2237, 1753
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.116, 1.05
No. of reflections	2237
No. of parameters	235
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.20

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O1ⁱ	0.9300	1.9100	2.830 (5)	171.00
O1W—H2W1···O2ⁱⁱ	0.8600	1.9000	2.751 (4)	168.00
O2W—H1W2···O1Wⁱⁱⁱ	0.8400	2.0000	2.774 (3)	153.00
O2W—H2W2···N1	0.8600	2.2200	2.826 (4)	127.00
N2—H1N2···O2W	0.95 (4)	1.90 (4)	2.832 (4)	170 (3)
O1—H1O1···O2ⁱⁱ	0.83 (4)	1.74 (5)	2.565 (5)	174 (5)
C17—H17A···O2W	0.9300	2.5200	3.408 (6)	161.00
C10—H10B···Cg1^iv	0.97	2.69	3.422 (5)	133
C8—H8A···Cg2^v	0.97	2.74	3.497 (5)	136

Symmetry codes: (i) −x, −y+1, z−1/2; (ii) −x, −y+1, z+1/2; (iii) x+1/2, −y+1/2, z; (iv) −x+1, −y+1, z−1/2; (v) −x+1, −y+1, z+1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-5471-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund (grant No. 305/PFIZIK/613312). RK thanks Universiti Sains Malaysia for the award of a postdoctoral research fellowship. HK thanks PNU for financial support. HKF also thanks Universiti Sains Malaysia for Research University Golden Goose Grant No. 1001/PFIZIK/811012.

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