6,6'-Dieth-oxy-2,2'-[4,5-dimethyl-o-phenyl-enebis(nitrilo-methyl-idyne)]diphenol-ethanol-water (1/1/1).

The title bis-Schiff base compound, C(26)H(28)N(2)O(4)·C(2)H(6)O·H(2)O, crystallizes as an ethanol and water solvate. Strong intra-molecular O-H⋯N hydrogen bonds generate S(6) ring motifs. The water H atoms form bifurcated O-H⋯(O,O) inter-molecular hydrogen bonds with the O atoms of the hydroxyl and eth-oxy groups with R(1) (2)(5) ring motifs, which may, in part, influence the mol-ecular configuration. The dihedral angles between the central benzene ring and the two outer benzene rings of the Schiff base mol-ecule are 5.64 (8) and 44.78 (9)°. The crystal structure is further stabilized by inter-molecular C-H⋯O and π-π inter-actions [centroid-centroid distances = 3.6139 (11)-3.7993 (11) Å].

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see, for example: Cakir et al. (2002 ▶); Eltayeb et al. (2007a ▶,b ▶); Karabıyık et al. (2007 ▶); Fun & Kia (2008 ▶); Fun, Kargar & Kia (2008 ▶); Fun, Kia & Kargar (2008 ▶). For applications of Schiff base ligands, see, for example: Hajioudis et al. (1987 ▶); Granovski et al. (1993 ▶); Dao et al. (2000 ▶); Shahrokhian et al. (2000 ▶); Eltayeb & Ahmed (2005 ▶); Fakhari et al. (2005 ▶); Karthikeyan et al. (2006 ▶); Sriram et al. (2006 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C26H28N2O4·C2H6O·H2O

M = 496.59

Monoclinic,

a = 9.5095 (5) Å

b = 25.6633 (12) Å

c = 10.7766 (5) Å

β = 99.177 (2)°

V = 2596.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.45 × 0.12 × 0.02 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.961, T max = 0.999

32813 measured reflections

7595 independent reflections

4303 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.160

S = 1.03

7595 reflections

341 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.51 e Å−3

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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008903/lh2786sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008903/lh2786Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H28N2O4·C2H6O·H2O	F(000) = 1064
Mr = 496.59	Dx = 1.270 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4281 reflections
a = 9.5095 (5) Å	θ = 2.3–27.2°
b = 25.6633 (12) Å	µ = 0.09 mm−1
c = 10.7766 (5) Å	T = 100 K
β = 99.177 (2)°	Plate, orange
V = 2596.3 (2) Å3	0.45 × 0.12 × 0.02 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	7595 independent reflections
Radiation source: fine-focus sealed tube	4303 reflections with I > 2σ(I)
graphite	Rint = 0.068
φ and ω scans	θmax = 30.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
Tmin = 0.961, Tmax = 0.999	k = −36→32
32813 measured reflections	l = −14→15

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0637P)2 + 0.5228P] where P = (Fo2 + 2Fc2)/3
7595 reflections	(Δ/σ)max < 0.001
341 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	−0.06040 (14)	0.16561 (5)	0.35336 (13)	0.0257 (3)
H1	0.0253	0.1707	0.3841	0.039*
O2	0.13555 (14)	0.07045 (5)	0.28857 (12)	0.0261 (3)
H2	0.1782	0.0973	0.3193	0.039*
O3	−0.33019 (13)	0.16242 (5)	0.25794 (12)	0.0250 (3)
O4	−0.00004 (14)	−0.01584 (5)	0.22724 (12)	0.0276 (3)
O5	0.1829 (2)	0.38301 (7)	0.43926 (18)	0.0696 (7)
H5	0.2336	0.3938	0.5052	0.104*
N1	0.16852 (16)	0.21898 (6)	0.42494 (13)	0.0202 (3)
N2	0.30447 (16)	0.12535 (6)	0.45335 (14)	0.0221 (4)
C1	−0.12615 (19)	0.21183 (7)	0.32673 (16)	0.0195 (4)
C2	−0.2720 (2)	0.21128 (7)	0.27477 (17)	0.0212 (4)
C3	−0.3428 (2)	0.25763 (8)	0.24528 (17)	0.0239 (4)
H3A	−0.4410	0.2573	0.2103	0.029*
C4	−0.2710 (2)	0.30517 (8)	0.26650 (18)	0.0271 (5)
H4A	−0.3207	0.3369	0.2456	0.032*
C5	−0.1292 (2)	0.30622 (8)	0.31737 (17)	0.0241 (4)
H5A	−0.0812	0.3387	0.3319	0.029*
C6	−0.0546 (2)	0.25953 (7)	0.34807 (16)	0.0197 (4)
C7	0.0960 (2)	0.26133 (8)	0.39833 (16)	0.0216 (4)
H7A	0.1422	0.2941	0.4120	0.026*
C8	0.31619 (19)	0.21948 (7)	0.47186 (16)	0.0195 (4)
C9	0.3962 (2)	0.26478 (8)	0.50515 (17)	0.0222 (4)
H9A	0.3501	0.2977	0.4944	0.027*
C10	0.5406 (2)	0.26294 (7)	0.55340 (16)	0.0212 (4)
C11	0.6084 (2)	0.21406 (8)	0.56871 (17)	0.0216 (4)
C12	0.5301 (2)	0.16936 (8)	0.53558 (16)	0.0222 (4)
H12A	0.5768	0.1365	0.5447	0.027*
C13	0.3845 (2)	0.17112 (7)	0.48914 (16)	0.0207 (4)
C14	0.3273 (2)	0.08414 (7)	0.52055 (17)	0.0236 (4)
H14A	0.3939	0.0857	0.5962	0.028*
C15	0.2554 (2)	0.03506 (8)	0.48551 (17)	0.0229 (4)
C16	0.2757 (2)	−0.00817 (8)	0.56692 (18)	0.0279 (5)
H16A	0.3398	−0.0056	0.6439	0.033*
C17	0.2041 (2)	−0.05394 (8)	0.53627 (19)	0.0287 (5)
H17A	0.2191	−0.0829	0.5917	0.034*
C18	0.1087 (2)	−0.05798 (8)	0.42326 (19)	0.0270 (4)
H18A	0.0579	−0.0895	0.4029	0.032*
C19	0.0884 (2)	−0.01644 (7)	0.34162 (17)	0.0232 (4)
C20	0.16074 (19)	0.03062 (7)	0.37184 (17)	0.0208 (4)
C21	−0.47745 (19)	0.15886 (8)	0.20175 (18)	0.0262 (4)
H21A	−0.4913	0.1729	0.1151	0.031*
H21B	−0.5377	0.1790	0.2515	0.031*
C22	−0.5166 (2)	0.10202 (8)	0.20022 (19)	0.0310 (5)
H22A	−0.6166	0.0978	0.1622	0.047*
H22B	−0.5027	0.0887	0.2865	0.047*
H22C	−0.4559	0.0826	0.1510	0.047*
C23	−0.0850 (2)	−0.06146 (8)	0.1942 (2)	0.0305 (5)
H23A	−0.1449	−0.0689	0.2592	0.037*
H23B	−0.0231	−0.0920	0.1869	0.037*
C24	−0.1771 (3)	−0.05042 (9)	0.0699 (2)	0.0410 (6)
H24A	−0.2390	−0.0804	0.0451	0.061*
H24B	−0.1166	−0.0441	0.0059	0.061*
H24C	−0.2358	−0.0196	0.0778	0.061*
C25	0.6220 (2)	0.31263 (8)	0.58803 (19)	0.0276 (5)
H25A	0.5559	0.3422	0.5782	0.041*
H25B	0.6935	0.3174	0.5328	0.041*
H25C	0.6694	0.3106	0.6756	0.041*
C26	0.7651 (2)	0.21015 (8)	0.62075 (18)	0.0279 (5)
H26A	0.7960	0.1738	0.6173	0.042*
H26B	0.7816	0.2222	0.7082	0.042*
H26C	0.8195	0.2319	0.5705	0.042*
C27	0.0836 (4)	0.45876 (12)	0.3369 (3)	0.0799 (11)
H27A	0.0918	0.4816	0.2655	0.120*
H27B	0.0995	0.4791	0.4148	0.120*
H27C	−0.0118	0.4433	0.3258	0.120*
C28	0.1892 (3)	0.41771 (13)	0.3437 (2)	0.0575 (8)
H28A	0.1756	0.3986	0.2629	0.069*
H28B	0.2852	0.4337	0.3553	0.069*
O1W	0.84548 (19)	0.08448 (7)	0.14875 (16)	0.0412 (4)
H1W1	0.920 (3)	0.0656 (11)	0.169 (3)	0.064 (9)*
H2W1	0.855 (3)	0.1065 (13)	0.199 (3)	0.076 (11)*

	U11	U22	U33	U12	U13	U23
O1	0.0167 (6)	0.0236 (7)	0.0347 (8)	0.0002 (6)	−0.0026 (6)	0.0009 (6)
O2	0.0295 (8)	0.0200 (7)	0.0262 (7)	−0.0036 (6)	−0.0031 (6)	0.0021 (6)
O3	0.0155 (6)	0.0262 (8)	0.0318 (7)	0.0000 (6)	−0.0008 (5)	−0.0009 (6)
O4	0.0285 (7)	0.0219 (7)	0.0291 (7)	−0.0042 (6)	−0.0058 (6)	−0.0017 (6)
O5	0.0928 (16)	0.0370 (11)	0.0628 (13)	−0.0105 (10)	−0.0368 (11)	0.0001 (9)
N1	0.0185 (8)	0.0257 (9)	0.0163 (7)	−0.0007 (7)	0.0022 (6)	−0.0002 (6)
N2	0.0210 (8)	0.0214 (9)	0.0230 (8)	−0.0016 (7)	0.0012 (7)	−0.0028 (6)
C1	0.0194 (9)	0.0234 (10)	0.0158 (8)	0.0027 (8)	0.0030 (7)	−0.0003 (7)
C2	0.0195 (9)	0.0257 (11)	0.0185 (9)	0.0005 (8)	0.0035 (7)	−0.0015 (7)
C3	0.0197 (9)	0.0326 (11)	0.0191 (9)	0.0035 (8)	0.0027 (7)	0.0008 (8)
C4	0.0274 (11)	0.0256 (11)	0.0283 (10)	0.0083 (9)	0.0048 (8)	0.0031 (8)
C5	0.0267 (10)	0.0220 (10)	0.0240 (9)	0.0011 (8)	0.0054 (8)	−0.0004 (8)
C6	0.0208 (9)	0.0255 (10)	0.0136 (8)	0.0018 (8)	0.0046 (7)	−0.0007 (7)
C7	0.0229 (10)	0.0238 (10)	0.0182 (9)	−0.0029 (8)	0.0036 (7)	−0.0008 (7)
C8	0.0196 (9)	0.0248 (10)	0.0141 (8)	−0.0014 (8)	0.0030 (7)	−0.0007 (7)
C9	0.0248 (10)	0.0229 (10)	0.0192 (9)	−0.0010 (8)	0.0042 (8)	−0.0009 (7)
C10	0.0234 (9)	0.0262 (10)	0.0146 (8)	−0.0059 (8)	0.0050 (7)	−0.0012 (7)
C11	0.0190 (9)	0.0297 (11)	0.0172 (8)	−0.0036 (8)	0.0056 (7)	−0.0021 (8)
C12	0.0210 (9)	0.0255 (10)	0.0198 (9)	0.0018 (8)	0.0022 (7)	−0.0006 (8)
C13	0.0229 (9)	0.0233 (10)	0.0162 (8)	−0.0014 (8)	0.0039 (7)	−0.0020 (7)
C14	0.0196 (9)	0.0291 (11)	0.0211 (9)	−0.0006 (8)	−0.0005 (8)	−0.0018 (8)
C15	0.0198 (9)	0.0241 (10)	0.0243 (9)	−0.0004 (8)	0.0018 (8)	−0.0009 (8)
C16	0.0274 (10)	0.0277 (11)	0.0269 (10)	0.0032 (9)	−0.0005 (8)	0.0040 (8)
C17	0.0295 (11)	0.0252 (11)	0.0302 (10)	0.0032 (9)	0.0015 (9)	0.0052 (8)
C18	0.0255 (10)	0.0203 (10)	0.0348 (11)	−0.0004 (8)	0.0038 (9)	−0.0005 (8)
C19	0.0199 (9)	0.0239 (10)	0.0253 (9)	0.0014 (8)	0.0015 (8)	−0.0026 (8)
C20	0.0196 (9)	0.0191 (10)	0.0238 (9)	0.0010 (8)	0.0039 (8)	−0.0007 (7)
C21	0.0162 (9)	0.0386 (12)	0.0226 (9)	−0.0009 (9)	−0.0009 (7)	−0.0001 (8)
C22	0.0208 (10)	0.0402 (13)	0.0317 (11)	−0.0052 (9)	0.0030 (9)	−0.0031 (9)
C23	0.0278 (11)	0.0227 (11)	0.0389 (11)	−0.0052 (9)	−0.0009 (9)	−0.0054 (9)
C24	0.0407 (13)	0.0367 (13)	0.0400 (12)	−0.0085 (11)	−0.0106 (11)	−0.0076 (10)
C25	0.0259 (10)	0.0299 (11)	0.0268 (10)	−0.0085 (9)	0.0033 (8)	−0.0021 (8)
C26	0.0209 (10)	0.0366 (12)	0.0256 (10)	−0.0027 (9)	0.0024 (8)	−0.0043 (9)
C27	0.081 (2)	0.0466 (18)	0.093 (2)	−0.0021 (17)	−0.044 (2)	−0.0018 (16)
C28	0.0434 (15)	0.096 (2)	0.0340 (13)	−0.0122 (16)	0.0109 (12)	−0.0044 (14)
O1W	0.0394 (10)	0.0386 (10)	0.0406 (9)	0.0105 (8)	−0.0088 (8)	−0.0115 (8)

O1—C1	1.350 (2)	C14—H14A	0.9500
O1—H1	0.8400	C15—C20	1.404 (2)
O2—C20	1.356 (2)	C15—C16	1.409 (3)
O2—H2	0.8400	C16—C17	1.372 (3)
O3—C2	1.371 (2)	C16—H16A	0.9500
O3—C21	1.437 (2)	C17—C18	1.401 (3)
O4—C19	1.377 (2)	C17—H17A	0.9500
O4—C23	1.435 (2)	C18—C19	1.376 (3)
O5—C28	1.370 (3)	C18—H18A	0.9500
O5—H5	0.8400	C19—C20	1.403 (3)
N1—C7	1.295 (2)	C21—C22	1.505 (3)
N1—C8	1.415 (2)	C21—H21A	0.9900
N2—C14	1.281 (2)	C21—H21B	0.9900
N2—C13	1.419 (2)	C22—H22A	0.9800
C1—C6	1.402 (3)	C22—H22B	0.9800
C1—C2	1.411 (2)	C22—H22C	0.9800
C2—C3	1.379 (3)	C23—C24	1.506 (3)
C3—C4	1.399 (3)	C23—H23A	0.9900
C3—H3A	0.9500	C23—H23B	0.9900
C4—C5	1.373 (3)	C24—H24A	0.9800
C4—H4A	0.9500	C24—H24B	0.9800
C5—C6	1.405 (3)	C24—H24C	0.9800
C5—H5A	0.9500	C25—H25A	0.9800
C6—C7	1.448 (3)	C25—H25B	0.9800
C7—H7A	0.9500	C25—H25C	0.9800
C8—C13	1.399 (3)	C26—H26A	0.9800
C8—C9	1.404 (3)	C26—H26B	0.9800
C9—C10	1.390 (3)	C26—H26C	0.9800
C9—H9A	0.9500	C27—C28	1.449 (4)
C10—C11	1.408 (3)	C27—H27A	0.9800
C10—C25	1.507 (3)	C27—H27B	0.9800
C11—C12	1.383 (3)	C27—H27C	0.9800
C11—C26	1.510 (3)	C28—H28A	0.9900
C12—C13	1.396 (3)	C28—H28B	0.9900
C12—H12A	0.9500	O1W—H1W1	0.86 (3)
C14—C15	1.454 (3)	O1W—H2W1	0.78 (3)
C1—O1—H1	109.5	C19—C18—C17	120.25 (18)
C20—O2—H2	109.5	C19—C18—H18A	119.9
C2—O3—C21	117.35 (14)	C17—C18—H18A	119.9
C19—O4—C23	116.90 (15)	C18—C19—O4	125.77 (17)
C28—O5—H5	109.5	C18—C19—C20	120.33 (17)
C7—N1—C8	122.35 (16)	O4—C19—C20	113.90 (16)
C14—N2—C13	119.64 (15)	O2—C20—C19	117.85 (16)
O1—C1—C6	122.41 (16)	O2—C20—C15	122.49 (17)
O1—C1—C2	117.93 (16)	C19—C20—C15	119.67 (17)
C6—C1—C2	119.66 (17)	O3—C21—C22	106.80 (16)
O3—C2—C3	125.94 (17)	O3—C21—H21A	110.4
O3—C2—C1	114.33 (16)	C22—C21—H21A	110.4
C3—C2—C1	119.73 (18)	O3—C21—H21B	110.4
C2—C3—C4	120.48 (17)	C22—C21—H21B	110.4
C2—C3—H3A	119.8	H21A—C21—H21B	108.6
C4—C3—H3A	119.8	C21—C22—H22A	109.5
C5—C4—C3	120.33 (18)	C21—C22—H22B	109.5
C5—C4—H4A	119.8	H22A—C22—H22B	109.5
C3—C4—H4A	119.8	C21—C22—H22C	109.5
C4—C5—C6	120.30 (18)	H22A—C22—H22C	109.5
C4—C5—H5A	119.9	H22B—C22—H22C	109.5
C6—C5—H5A	119.9	O4—C23—C24	107.00 (17)
C1—C6—C5	119.50 (17)	O4—C23—H23A	110.3
C1—C6—C7	120.96 (17)	C24—C23—H23A	110.3
C5—C6—C7	119.52 (17)	O4—C23—H23B	110.3
N1—C7—C6	121.07 (17)	C24—C23—H23B	110.3
N1—C7—H7A	119.5	H23A—C23—H23B	108.6
C6—C7—H7A	119.5	C23—C24—H24A	109.5
C13—C8—C9	118.63 (17)	C23—C24—H24B	109.5
C13—C8—N1	116.93 (16)	H24A—C24—H24B	109.5
C9—C8—N1	124.41 (17)	C23—C24—H24C	109.5
C10—C9—C8	122.02 (18)	H24A—C24—H24C	109.5
C10—C9—H9A	119.0	H24B—C24—H24C	109.5
C8—C9—H9A	119.0	C10—C25—H25A	109.5
C9—C10—C11	118.72 (17)	C10—C25—H25B	109.5
C9—C10—C25	120.09 (18)	H25A—C25—H25B	109.5
C11—C10—C25	121.19 (17)	C10—C25—H25C	109.5
C12—C11—C10	119.47 (17)	H25A—C25—H25C	109.5
C12—C11—C26	119.94 (18)	H25B—C25—H25C	109.5
C10—C11—C26	120.59 (17)	C11—C26—H26A	109.5
C11—C12—C13	121.84 (18)	C11—C26—H26B	109.5
C11—C12—H12A	119.1	H26A—C26—H26B	109.5
C13—C12—H12A	119.1	C11—C26—H26C	109.5
C12—C13—C8	119.30 (17)	H26A—C26—H26C	109.5
C12—C13—N2	121.93 (17)	H26B—C26—H26C	109.5
C8—C13—N2	118.71 (16)	C28—C27—H27A	109.5
N2—C14—C15	122.55 (17)	C28—C27—H27B	109.5
N2—C14—H14A	118.7	H27A—C27—H27B	109.5
C15—C14—H14A	118.7	C28—C27—H27C	109.5
C20—C15—C16	118.99 (17)	H27A—C27—H27C	109.5
C20—C15—C14	120.42 (17)	H27B—C27—H27C	109.5
C16—C15—C14	120.55 (17)	O5—C28—C27	113.5 (3)
C17—C16—C15	120.73 (18)	O5—C28—H28A	108.9
C17—C16—H16A	119.6	C27—C28—H28A	108.9
C15—C16—H16A	119.6	O5—C28—H28B	108.9
C16—C17—C18	120.03 (18)	C27—C28—H28B	108.9
C16—C17—H17A	120.0	H28A—C28—H28B	107.7
C18—C17—H17A	120.0	H1W1—O1W—H2W1	103 (3)
C21—O3—C2—C3	1.6 (3)	C26—C11—C12—C13	178.89 (17)
C21—O3—C2—C1	−178.13 (16)	C11—C12—C13—C8	2.0 (3)
O1—C1—C2—O3	0.3 (2)	C11—C12—C13—N2	179.06 (17)
C6—C1—C2—O3	179.82 (16)	C9—C8—C13—C12	−1.7 (3)
O1—C1—C2—C3	−179.47 (16)	N1—C8—C13—C12	−179.82 (16)
C6—C1—C2—C3	0.1 (3)	C9—C8—C13—N2	−178.84 (16)
O3—C2—C3—C4	−179.69 (17)	N1—C8—C13—N2	3.0 (2)
C1—C2—C3—C4	0.0 (3)	C14—N2—C13—C12	40.6 (3)
C2—C3—C4—C5	−0.2 (3)	C14—N2—C13—C8	−142.33 (18)
C3—C4—C5—C6	0.3 (3)	C13—N2—C14—C15	−176.25 (17)
O1—C1—C6—C5	179.54 (16)	N2—C14—C15—C20	2.6 (3)
C2—C1—C6—C5	0.0 (3)	N2—C14—C15—C16	−175.16 (19)
O1—C1—C6—C7	1.1 (3)	C20—C15—C16—C17	−0.2 (3)
C2—C1—C6—C7	−178.44 (17)	C14—C15—C16—C17	177.60 (19)
C4—C5—C6—C1	−0.2 (3)	C15—C16—C17—C18	−0.4 (3)
C4—C5—C6—C7	178.27 (18)	C16—C17—C18—C19	1.1 (3)
C8—N1—C7—C6	178.76 (16)	C17—C18—C19—O4	178.80 (19)
C1—C6—C7—N1	0.0 (3)	C17—C18—C19—C20	−1.2 (3)
C5—C6—C7—N1	−178.43 (17)	C23—O4—C19—C18	4.2 (3)
C7—N1—C8—C13	−175.89 (16)	C23—O4—C19—C20	−175.79 (17)
C7—N1—C8—C9	6.1 (3)	C18—C19—C20—O2	−179.31 (18)
C13—C8—C9—C10	0.6 (3)	O4—C19—C20—O2	0.6 (2)
N1—C8—C9—C10	178.60 (17)	C18—C19—C20—C15	0.6 (3)
C8—C9—C10—C11	0.2 (3)	O4—C19—C20—C15	−179.42 (17)
C8—C9—C10—C25	−179.88 (17)	C16—C15—C20—O2	−179.95 (18)
C9—C10—C11—C12	0.0 (3)	C14—C15—C20—O2	2.2 (3)
C25—C10—C11—C12	−179.86 (17)	C16—C15—C20—C19	0.1 (3)
C9—C10—C11—C26	179.99 (17)	C14—C15—C20—C19	−177.71 (18)
C25—C10—C11—C26	0.1 (3)	C2—O3—C21—C22	−177.08 (16)
C10—C11—C12—C13	−1.2 (3)	C19—O4—C23—C24	177.06 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.84	2.584 (2)	146
O1W—H1W1···O2i	0.86 (3)	2.24 (3)	2.947 (2)	139 (3)
O1W—H1W1···O4i	0.86 (3)	2.28 (3)	3.018 (2)	145 (3)
O2—H2···N2	0.84	1.87	2.609 (2)	146
O1W—H2W1···O1i	0.78 (3)	2.30 (3)	3.061 (2)	166 (3)
O1W—H2W1···O3i	0.78 (3)	2.43 (3)	2.967 (2)	127 (3)
O5—H5···O1Wii	0.84	1.82	2.659 (3)	179
C7—H7A···O5	0.95	2.33	3.242 (3)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.84	1.84	2.584 (2)	146
O2—H2⋯N2	0.84	1.87	2.609 (2)	146
O1W—H1W1⋯O2i	0.86 (3)	2.24 (3)	2.947 (2)	139 (3)
O1W—H1W1⋯O4i	0.86 (3)	2.28 (3)	3.018 (2)	145 (3)
O1W—H2W1⋯O1i	0.78 (3)	2.30 (3)	3.061 (2)	166 (3)
O1W—H2W1⋯O3i	0.78 (3)	2.43 (3)	2.967 (2)	127 (3)
O5—H5⋯O1Wii	0.84	1.82	2.659 (3)	179
C7—H7A⋯O5	0.95	2.33	3.242 (3)	162

Symmetry codes: (i) ; (ii) .