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

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

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

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.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810002916/lh2982sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810002916/lh2982Isup2.hkl Contains datablock I

CCDC reference: 769947

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R factor = 0.046
wR factor = 0.141
Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     --  C7      ..       5.97 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C11    --  C12     ..       5.89 su
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         16
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         30

Alert level G
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)        300 Deg.
PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C23

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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).