6,6′-Dimeth­oxy-2,2′-[4,5-dimethyl-o-phenyl­enebis(nitrilo­methyl­idyne)]diphenol monohydrate

Kargar, H.; Kia, R.; Ullah Khan, I.; Sahraei, A.

doi:10.1107/S1600536810002916

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o539

doi:10.1107/S1600536810002916

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6,6′-Dimethoxy-2,2′-[4,5-dimethyl-o-phenylenebis(nitrilomethylidyne)]diphenol monohydrate

Hadi Kargar,^a Reza Kia,^b ‡ Islam Ullah Khan ^c ^* and Atefeh Sahraei ^a

^aDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran, ^bDepartment of Chemistry, Science and Research Campus, Islamic Azad University, Poonak, Tehran, Iran, and ^cMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan
^*Correspondence e-mail: iuklodhi@yahoo.com

(Received 17 January 2010; accepted 23 January 2010; online 6 February 2010)

In the title compound, C₂₄H₂₄N₂O₄·H₂O, the dihedral angles between the central benzene ring and the two outer benzene rings of the Schiff base are 65.06 (9) and 3.02 (9)°. Strong intramolecular O—H⋯N hydrogen bonds generate S(6) ring motifs. The H atoms of the water molecule act as donors in the formation of bifurcated O—H⋯(O,O) intermolecular hydrogen bonds with the O atoms of the hydroxy and methoxy groups with R₁²(5) ring motifs; these may influence the molecular conformation.

Related literature

For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For related structures, see: Cakir et al. (2002 ); Eltayeb & Ahmed (2005 ); Eltayeb et al. (2007 ); Kargar et al. (2009 ). For background to the applications of Schiff base ligands as thermochromic and photochromic materials, see: Hajioudis et al. (1987 ).

Experimental

Crystal data

C₂₄H₂₄N₂O₄·H₂O
M_r = 422.47
Triclinic, $[P \overline 1]$
a = 8.7431 (5) Å
b = 10.3049 (6) Å
c = 13.6614 (7) Å
α = 69.556 (3)°
β = 83.846 (3)°
γ = 70.280 (3)°
V = 1085.6 (1) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.973, T_max = 0.987
23270 measured reflections
5369 independent reflections
2912 reflections with I > 2I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.141
S = 1.01
5369 reflections
284 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.96	1.72	2.5929 (18)	150
O2—H2⋯N2	0.96	1.66	2.5704 (18)	156
O1W—H1W⋯O1	0.97	2.21	3.050 (2)	144
O1W—H1W⋯O3	0.97	2.50	3.366 (2)	148
O1W—H2W⋯O2	0.97	2.15	3.079 (2)	160
O1W—H2W⋯O4	0.97	2.55	3.271 (2)	131

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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/S1600536810002916/lh2982sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810002916/lh2982Isup2.hkl

checkCIF report

Comment top

Schiff base ligands are one of the most prevalent systems in coordination chemistry. They can show thermochromic and photochromic properties (Hajioudis et al. (1987). As part of a general study of tetradenate Schiff bases (Kargar et al. 2009), we have determined the crystal structure of the title compound.

The asymmetric unit of the title compound, Fig. 1, comprises a Schiff base ligand and a water molecule of crystallization. The bond lengths (Allen et al., 1987) and angles are within the normal ranges and comparable to previously reported structures (Eltayeb & Ahmed, 2005; Eltayeb et al., 2007; Cakir et al. 2002; Kargar et al., 2009 ). The dihedral angles between the central benzene ring and the two outer benzene rings of the Schiff base are 65.06 (9) and 3.02 (9)°. Strong intramolecular O—H···N hydrogen bonds generate S(6) ring motifs (Bernstein et al., 1995). The hydrogen atoms of the water molecule form bifurcated intermolecular hydrogen bonds with the oxygen atoms of the hydroxy and methoxy groups with R²₁(5) ring motifs (Bernstein et al., 1995), which may, in part, influence the molecular configuration (Table 1). A view of part of the crystal structure is shown in Fig .2.

Related literature top

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see: Cakir et al. (2002); Eltayeb & Ahmed (2005); Eltayeb et al. (2007); Kargar et al. (2009). For background to the applications of Schiff base ligands as thermochromic and photochromic materials, see: Hajioudis et al. (1987).

Experimental top

The title compound was synthesized by adding 3-methoxy-salicylaldehyde (4 mmol) to a solution of 4,5-dimethyl-o-phenylenediamine (2 mmol) in ethanol (20 ml). The mixture was refluxed with stirring for half an hour. The resultant yellow solution was filtered. Yellow single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (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 asymmetric unit of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering. Intra- and intermolecular hydrogen bonds are drawn as dashed lines.
	Fig. 2. The crystal packing of the title compound wieved along the a-axis. Hydrogen bonds are shown as dashed lines.

6,6'-Dimethoxy-2,2'-[4,5-dimethyl-o- phenylenebis(nitrilomethylidyne)]diphenol monohydrate top

Crystal data top

C₂₄H₂₄N₂O₄·H₂O	Z = 2
M_r = 422.47	F(000) = 448
Triclinic, P1	D_x = 1.292 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7431 (5) Å	Cell parameters from 5124 reflections
b = 10.3049 (6) Å	θ = 2.2–25.0°
c = 13.6614 (7) Å	µ = 0.09 mm⁻¹
α = 69.556 (3)°	T = 296 K
β = 83.846 (3)°	Block, yellow
γ = 70.280 (3)°	0.30 × 0.20 × 0.15 mm
V = 1085.6 (1) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5369 independent reflections
Radiation source: fine-focus sealed tube	2912 reflections with I > 2˘I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
T_min = 0.973, T_max = 0.987	k = −12→13
23270 measured reflections	l = −18→18

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0622P)² + 0.1326P] where P = (F_o² + 2F_c²)/3
5369 reflections	(Δ/σ)_max < 0.001
284 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₄H₂₄N₂O₄·H₂O	γ = 70.280 (3)°
M_r = 422.47	V = 1085.6 (1) Å³
Triclinic, P1	Z = 2
a = 8.7431 (5) Å	Mo Kα radiation
b = 10.3049 (6) Å	µ = 0.09 mm⁻¹
c = 13.6614 (7) Å	T = 296 K
α = 69.556 (3)°	0.30 × 0.20 × 0.15 mm
β = 83.846 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5369 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2912 reflections with I > 2˘I)
T_min = 0.973, T_max = 0.987	R_int = 0.031
23270 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.01	Δρ_max = 0.20 e Å⁻³
5369 reflections	Δρ_min = −0.18 e Å⁻³
284 parameters

Special details top

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	0.48196 (13)	0.46281 (13)	0.27727 (9)	0.0574 (3)
H1	0.5531	0.4027	0.3362	0.086*
O2	0.58907 (14)	0.10375 (12)	0.31399 (9)	0.0563 (3)
H2	0.6463	0.1102	0.3678	0.084*
O3	0.34071 (17)	0.62867 (15)	0.09838 (10)	0.0749 (4)
O4	0.45471 (16)	0.01221 (14)	0.20011 (10)	0.0692 (4)
N1	0.74540 (15)	0.32782 (13)	0.39027 (10)	0.0436 (3)
N2	0.74691 (15)	0.04912 (14)	0.47979 (10)	0.0438 (3)
C1	0.5789 (2)	0.51020 (17)	0.19880 (12)	0.0465 (4)
C2	0.5055 (2)	0.59934 (18)	0.10105 (13)	0.0549 (5)
C3	0.5987 (3)	0.6496 (2)	0.01908 (14)	0.0687 (6)
H3A	0.5502	0.7081	−0.0459	0.082*
C4	0.7642 (3)	0.6143 (2)	0.03171 (15)	0.0733 (6)
H4A	0.8262	0.6484	−0.0249	0.088*
C5	0.8378 (2)	0.5294 (2)	0.12719 (14)	0.0630 (5)
H5A	0.9489	0.5076	0.1354	0.076*
C6	0.7458 (2)	0.47583 (17)	0.21197 (12)	0.0469 (4)
C7	0.8237 (2)	0.38539 (17)	0.31301 (13)	0.0466 (4)
H7A	0.9335	0.3692	0.3214	0.056*
C8	0.82177 (17)	0.24595 (16)	0.48957 (11)	0.0401 (4)
C9	0.88484 (19)	0.30867 (18)	0.54329 (13)	0.0475 (4)
H9A	0.8844	0.4046	0.5110	0.057*
C10	0.94858 (19)	0.2329 (2)	0.64369 (13)	0.0496 (4)
C11	0.95310 (19)	0.0878 (2)	0.69018 (12)	0.0507 (4)
C12	0.88856 (19)	0.02546 (18)	0.63693 (12)	0.0493 (4)
H12A	0.8914	−0.0712	0.6685	0.059*
C13	0.81949 (17)	0.10333 (17)	0.53748 (12)	0.0410 (4)
C14	0.74023 (18)	−0.08139 (17)	0.51154 (13)	0.0467 (4)
H14A	0.7864	−0.1459	0.5759	0.056*
C15	0.66348 (18)	−0.13050 (17)	0.45037 (13)	0.0455 (4)
C16	0.6581 (2)	−0.27411 (18)	0.48757 (15)	0.0563 (5)
H16A	0.7039	−0.3370	0.5524	0.068*
C17	0.5870 (2)	−0.32238 (19)	0.43002 (16)	0.0605 (5)
H17A	0.5842	−0.4179	0.4556	0.073*
C18	0.5181 (2)	−0.2296 (2)	0.33301 (16)	0.0589 (5)
H18A	0.4699	−0.2637	0.2940	0.071*
C19	0.5206 (2)	−0.08833 (19)	0.29418 (14)	0.0517 (4)
C20	0.59181 (18)	−0.03598 (17)	0.35303 (13)	0.0458 (4)
C21	0.2574 (3)	0.7227 (2)	0.00270 (16)	0.0918 (8)
H21A	0.1438	0.7335	0.0106	0.138*
H21B	0.3006	0.6814	−0.0514	0.138*
H21C	0.2715	0.8168	−0.0157	0.138*
C22	0.4007 (3)	−0.0392 (3)	0.13155 (17)	0.0840 (7)
H22A	0.3546	0.0412	0.0697	0.126*
H22B	0.3198	−0.0834	0.1654	0.126*
H22C	0.4908	−0.1104	0.1129	0.126*
C23	1.0072 (2)	0.3092 (2)	0.70012 (15)	0.0693 (6)
H23A	0.9946	0.4077	0.6554	0.104*
H23B	1.1198	0.2580	0.7188	0.104*
H23C	0.9447	0.3106	0.7622	0.104*
C24	1.0284 (2)	−0.0036 (3)	0.79731 (14)	0.0789 (7)
H24A	0.9768	0.0447	0.8466	0.118*
H24B	1.1423	−0.0157	0.7950	0.118*
H24C	1.0137	−0.0977	0.8183	0.118*
O1W	0.25045 (16)	0.32247 (16)	0.23580 (10)	0.0795 (4)
H1W	0.2953	0.4012	0.2238	0.119*
H2W	0.3547	0.2463	0.2467	0.119*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0557 (7)	0.0600 (8)	0.0444 (7)	−0.0177 (6)	−0.0123 (6)	−0.0001 (6)
O2	0.0718 (8)	0.0398 (7)	0.0541 (7)	−0.0176 (6)	−0.0099 (6)	−0.0094 (5)
O3	0.0744 (9)	0.0733 (9)	0.0556 (8)	−0.0061 (7)	−0.0298 (7)	−0.0043 (7)
O4	0.0853 (9)	0.0595 (8)	0.0662 (9)	−0.0225 (7)	−0.0143 (7)	−0.0214 (7)
N1	0.0496 (8)	0.0390 (7)	0.0354 (7)	−0.0115 (6)	−0.0089 (6)	−0.0044 (6)
N2	0.0436 (7)	0.0394 (8)	0.0416 (8)	−0.0102 (6)	0.0013 (6)	−0.0088 (6)
C1	0.0625 (10)	0.0373 (9)	0.0362 (9)	−0.0140 (8)	−0.0068 (8)	−0.0078 (7)
C2	0.0712 (12)	0.0433 (10)	0.0424 (10)	−0.0082 (9)	−0.0148 (9)	−0.0104 (8)
C3	0.1010 (17)	0.0537 (12)	0.0371 (10)	−0.0130 (11)	−0.0127 (10)	−0.0058 (9)
C4	0.0947 (17)	0.0735 (14)	0.0409 (11)	−0.0281 (12)	0.0079 (10)	−0.0076 (10)
C5	0.0733 (12)	0.0650 (12)	0.0466 (11)	−0.0248 (10)	0.0049 (9)	−0.0125 (9)
C6	0.0592 (10)	0.0412 (9)	0.0377 (9)	−0.0143 (8)	−0.0039 (8)	−0.0108 (7)
C7	0.0499 (9)	0.0434 (9)	0.0439 (10)	−0.0111 (8)	−0.0065 (8)	−0.0130 (8)
C8	0.0354 (8)	0.0404 (9)	0.0347 (8)	−0.0052 (6)	−0.0040 (6)	−0.0064 (7)
C9	0.0458 (9)	0.0467 (10)	0.0458 (10)	−0.0111 (7)	−0.0050 (7)	−0.0125 (8)
C10	0.0394 (9)	0.0627 (11)	0.0426 (9)	−0.0089 (8)	−0.0027 (7)	−0.0192 (9)
C11	0.0405 (9)	0.0648 (12)	0.0348 (9)	−0.0055 (8)	−0.0033 (7)	−0.0123 (8)
C12	0.0457 (9)	0.0437 (9)	0.0400 (9)	−0.0032 (7)	−0.0007 (7)	−0.0026 (7)
C13	0.0352 (8)	0.0433 (9)	0.0363 (8)	−0.0057 (7)	−0.0001 (6)	−0.0099 (7)
C14	0.0420 (9)	0.0428 (10)	0.0437 (9)	−0.0084 (7)	0.0034 (7)	−0.0064 (8)
C15	0.0383 (8)	0.0391 (9)	0.0527 (10)	−0.0088 (7)	0.0081 (7)	−0.0132 (8)
C16	0.0506 (10)	0.0421 (10)	0.0660 (12)	−0.0133 (8)	0.0086 (9)	−0.0099 (9)
C17	0.0549 (11)	0.0407 (10)	0.0834 (14)	−0.0200 (8)	0.0131 (10)	−0.0169 (10)
C18	0.0511 (10)	0.0542 (11)	0.0801 (14)	−0.0199 (9)	0.0106 (10)	−0.0329 (11)
C19	0.0472 (9)	0.0464 (10)	0.0590 (11)	−0.0115 (8)	0.0041 (8)	−0.0190 (9)
C20	0.0415 (9)	0.0387 (9)	0.0554 (10)	−0.0116 (7)	0.0079 (8)	−0.0171 (8)
C21	0.1047 (17)	0.0766 (15)	0.0687 (14)	0.0037 (13)	−0.0514 (13)	−0.0104 (12)
C22	0.1109 (18)	0.0963 (17)	0.0642 (14)	−0.0490 (14)	0.0015 (12)	−0.0350 (13)
C23	0.0644 (12)	0.0936 (16)	0.0568 (12)	−0.0233 (11)	−0.0064 (9)	−0.0333 (11)
C24	0.0728 (13)	0.0990 (17)	0.0419 (11)	−0.0162 (12)	−0.0161 (9)	−0.0021 (11)
O1W	0.0693 (9)	0.0887 (11)	0.0677 (9)	−0.0254 (8)	−0.0075 (7)	−0.0086 (8)

Geometric parameters (Å, º) top

O1—C1	1.3511 (19)	C11—C12	1.385 (2)
O1—H1	0.9574	C11—C24	1.512 (2)
O2—C20	1.3422 (18)	C12—C13	1.394 (2)
O2—H2	0.9642	C12—H12A	0.9300
O3—C2	1.371 (2)	C14—C15	1.432 (2)
O3—C21	1.422 (2)	C14—H14A	0.9300
O4—C19	1.372 (2)	C15—C16	1.402 (2)
O4—C22	1.411 (2)	C15—C20	1.404 (2)
N1—C7	1.271 (2)	C16—C17	1.356 (3)
N1—C8	1.4186 (18)	C16—H16A	0.9300
N2—C14	1.281 (2)	C17—C18	1.389 (3)
N2—C13	1.411 (2)	C17—H17A	0.9300
C1—C6	1.396 (2)	C18—C19	1.372 (2)
C1—C2	1.403 (2)	C18—H18A	0.9300
C2—C3	1.367 (3)	C19—C20	1.401 (2)
C3—C4	1.382 (3)	C21—H21A	0.9600
C3—H3A	0.9300	C21—H21B	0.9600
C4—C5	1.373 (3)	C21—H21C	0.9600
C4—H4A	0.9300	C22—H22A	0.9600
C5—C6	1.395 (2)	C22—H22B	0.9600
C5—H5A	0.9300	C22—H22C	0.9600
C6—C7	1.453 (2)	C23—H23A	0.9600
C7—H7A	0.9300	C23—H23B	0.9600
C8—C9	1.385 (2)	C23—H23C	0.9600
C8—C13	1.391 (2)	C24—H24A	0.9600
C9—C10	1.387 (2)	C24—H24B	0.9600
C9—H9A	0.9300	C24—H24C	0.9600
C10—C11	1.394 (2)	O1W—H1W	0.9731
C10—C23	1.502 (2)	O1W—H2W	0.9664

C1—O1—H1	105.3	N2—C14—H14A	119.2
C20—O2—H2	101.6	C15—C14—H14A	119.2
C2—O3—C21	117.48 (16)	C16—C15—C20	119.09 (16)
C19—O4—C22	117.25 (15)	C16—C15—C14	120.16 (16)
C7—N1—C8	120.70 (13)	C20—C15—C14	120.75 (15)
C14—N2—C13	123.85 (14)	C17—C16—C15	120.75 (17)
O1—C1—C6	122.82 (14)	C17—C16—H16A	119.6
O1—C1—C2	117.44 (16)	C15—C16—H16A	119.6
C6—C1—C2	119.74 (16)	C16—C17—C18	120.21 (17)
C3—C2—O3	125.95 (16)	C16—C17—H17A	119.9
C3—C2—C1	119.61 (18)	C18—C17—H17A	119.9
O3—C2—C1	114.44 (16)	C19—C18—C17	120.71 (18)
C2—C3—C4	120.71 (17)	C19—C18—H18A	119.6
C2—C3—H3A	119.6	C17—C18—H18A	119.6
C4—C3—H3A	119.6	C18—C19—O4	125.26 (17)
C5—C4—C3	120.52 (19)	C18—C19—C20	119.90 (17)
C5—C4—H4A	119.7	O4—C19—C20	114.83 (15)
C3—C4—H4A	119.7	O2—C20—C19	118.51 (15)
C4—C5—C6	119.97 (19)	O2—C20—C15	122.17 (15)
C4—C5—H5A	120.0	C19—C20—C15	119.32 (15)
C6—C5—H5A	120.0	O3—C21—H21A	109.5
C5—C6—C1	119.44 (15)	O3—C21—H21B	109.5
C5—C6—C7	120.03 (16)	H21A—C21—H21B	109.5
C1—C6—C7	120.54 (15)	O3—C21—H21C	109.5
N1—C7—C6	121.65 (15)	H21A—C21—H21C	109.5
N1—C7—H7A	119.2	H21B—C21—H21C	109.5
C6—C7—H7A	119.2	O4—C22—H22A	109.5
C9—C8—C13	119.56 (14)	O4—C22—H22B	109.5
C9—C8—N1	121.60 (14)	H22A—C22—H22B	109.5
C13—C8—N1	118.58 (14)	O4—C22—H22C	109.5
C8—C9—C10	122.06 (16)	H22A—C22—H22C	109.5
C8—C9—H9A	119.0	H22B—C22—H22C	109.5
C10—C9—H9A	119.0	C10—C23—H23A	109.5
C9—C10—C11	118.54 (16)	C10—C23—H23B	109.5
C9—C10—C23	119.63 (17)	H23A—C23—H23B	109.5
C11—C10—C23	121.82 (15)	C10—C23—H23C	109.5
C12—C11—C10	119.41 (14)	H23A—C23—H23C	109.5
C12—C11—C24	119.24 (17)	H23B—C23—H23C	109.5
C10—C11—C24	121.35 (17)	C11—C24—H24A	109.5
C11—C12—C13	121.97 (16)	C11—C24—H24B	109.5
C11—C12—H12A	119.0	H24A—C24—H24B	109.5
C13—C12—H12A	119.0	C11—C24—H24C	109.5
C8—C13—C12	118.37 (15)	H24A—C24—H24C	109.5
C8—C13—N2	116.34 (13)	H24B—C24—H24C	109.5
C12—C13—N2	125.28 (15)	H1W—O1W—H2W	95.0
N2—C14—C15	121.63 (15)

C21—O3—C2—C3	−1.7 (3)	C10—C11—C12—C13	0.3 (2)
C21—O3—C2—C1	177.79 (17)	C24—C11—C12—C13	−179.15 (15)
O1—C1—C2—C3	−179.75 (16)	C9—C8—C13—C12	−3.1 (2)
C6—C1—C2—C3	1.2 (3)	N1—C8—C13—C12	−177.31 (14)
O1—C1—C2—O3	0.7 (2)	C9—C8—C13—N2	177.27 (13)
C6—C1—C2—O3	−178.33 (15)	N1—C8—C13—N2	3.0 (2)
O3—C2—C3—C4	178.97 (18)	C11—C12—C13—C8	2.5 (2)
C1—C2—C3—C4	−0.5 (3)	C11—C12—C13—N2	−177.89 (14)
C2—C3—C4—C5	−0.7 (3)	C14—N2—C13—C8	177.54 (14)
C3—C4—C5—C6	1.1 (3)	C14—N2—C13—C12	−2.1 (2)
C4—C5—C6—C1	−0.4 (3)	C13—N2—C14—C15	179.30 (14)
C4—C5—C6—C7	179.75 (18)	N2—C14—C15—C16	−179.90 (15)
O1—C1—C6—C5	−179.76 (16)	N2—C14—C15—C20	−0.3 (2)
C2—C1—C6—C5	−0.7 (2)	C20—C15—C16—C17	1.0 (2)
O1—C1—C6—C7	0.1 (2)	C14—C15—C16—C17	−179.45 (16)
C2—C1—C6—C7	179.11 (15)	C15—C16—C17—C18	0.0 (3)
C8—N1—C7—C6	−176.84 (14)	C16—C17—C18—C19	−0.2 (3)
C5—C6—C7—N1	−175.85 (16)	C17—C18—C19—O4	−179.23 (16)
C1—C6—C7—N1	4.3 (2)	C17—C18—C19—C20	−0.6 (3)
C7—N1—C8—C9	61.2 (2)	C22—O4—C19—C18	−9.5 (3)
C7—N1—C8—C13	−124.72 (17)	C22—O4—C19—C20	171.84 (16)
C13—C8—C9—C10	0.9 (2)	C18—C19—C20—O2	−178.50 (15)
N1—C8—C9—C10	174.99 (14)	O4—C19—C20—O2	0.3 (2)
C8—C9—C10—C11	1.9 (2)	C18—C19—C20—C15	1.5 (2)
C8—C9—C10—C23	−176.79 (15)	O4—C19—C20—C15	−179.69 (14)
C9—C10—C11—C12	−2.5 (2)	C16—C15—C20—O2	178.33 (14)
C23—C10—C11—C12	176.17 (15)	C14—C15—C20—O2	−1.3 (2)
C9—C10—C11—C24	176.97 (16)	C16—C15—C20—C19	−1.7 (2)
C23—C10—C11—C24	−4.4 (3)	C14—C15—C20—C19	178.70 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.96	1.72	2.5929 (18)	150
O1W—H1W···O1	0.97	2.21	3.050 (2)	144
O1W—H1W···O3	0.97	2.50	3.366 (2)	148
O2—H2···N2	0.96	1.66	2.5704 (18)	156
O1W—H2W···O2	0.97	2.15	3.079 (2)	160
O1W—H2W···O4	0.97	2.55	3.271 (2)	131

Experimental details

Crystal data
Chemical formula	C₂₄H₂₄N₂O₄·H₂O
M_r	422.47
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.7431 (5), 10.3049 (6), 13.6614 (7)
α, β, γ (°)	69.556 (3), 83.846 (3), 70.280 (3)
V (Å³)	1085.6 (1)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.973, 0.987
No. of measured, independent and observed [I > 2˘I)] reflections	23270, 5369, 2912
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.141, 1.01
No. of reflections	5369
No. of parameters	284
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.18

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
O1—H1···N1	0.9600	1.7200	2.5929 (18)	150.00
O1W—H1W···O1	0.9700	2.2100	3.050 (2)	144.00
O1W—H1W···O3	0.9700	2.5000	3.366 (2)	148.00
O2—H2···N2	0.9600	1.6600	2.5704 (18)	156.00
O1W—H2W···O2	0.9700	2.1500	3.079 (2)	160.00
O1W—H2W···O4	0.9700	2.5500	3.271 (2)	131.00

Footnotes

‡Thomson Reuters Researcher ID: A-5471-2009.

Acknowledgements

HK and AJ thank PNU for financial support. IUK thanks GC University of Lahore, Pakistan, for the research facilities.

References

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