(Z)-6-{2-[(E)-2,4-Dihydroxy-benzyl-ideneamino]phenyl-amino-methyl-ene}-3-hydroxy-cyclo-hexa-2,4-dienone toluene solvate.

The bis-Schiff base title compound, C(20)H(16)N(2)O(4)·C(7)H(8), crystallized as a toluene solvate. In the solid state, it is present as its prototropic tautomer formed by transfer of one of the ortho-hydroxyl H atoms. The proton transfer is accompanied by a shift of electron pairs, as is evident from the observed C-O and C-N bond distances of 1.305 (2) and 1.315 (2) Å, which are largely consistent with C=O and C-N distances. The actual mol-ecule present in the solid state is thus the charge-neutral β-keto amine, with a small contribution of its zwitterionic valence tautomer via partial delocalization of electron pairs along the N-C-C-C-O atom chain. The dihedral angles between the central benzene ring and the two outer benzene rings of the Schiff base are 51.99 (8) and 12.95 (9)°. Intra-molecular O-H⋯N and N-H⋯O hydrogen bonds generate S(6) ring motifs, whereas intra-molecular N-H⋯N hydrogen bonds generate S(5) ring motifs. In the crystal structure, O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions link the mol-ecules into one-dimensional zigzag chains along the b axis; these chains are further stacked by O-H⋯O and weak C-H⋯O inter-actions along the c axis, forming two-dimensional extended networks parallel to the bc plane. In addition, the crystal structure is further stabilized by weak C-H⋯π and π-π inter-actions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see, for example: Cakir et al. (2002 ▶); Eltayeb et al. (2007a ▶,b ▶); Karabiyik et al. (2007 ▶); Fun, Kargar & Kia (2008 ▶); Fun, Kia & Kargar (2008 ▶); Fun, Mirkhani et al. (2008 ▶). For background on 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 related literature, see: Fun & Kia (2008 ▶).

Experimental

Crystal data

C20H16N2O4·C7H8

M = 440.48

Monoclinic,

a = 11.9753 (3) Å

b = 18.8539 (5) Å

c = 9.9240 (2) Å

β = 108.819 (1)°

V = 2120.87 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100.0 (1) K

0.25 × 0.13 × 0.02 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.954, T max = 0.994

24830 measured reflections

6233 independent reflections

4023 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.163

S = 1.11

6233 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.76 e Å−3

Δρmin = −0.32 e Å−3

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, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026305/zl2135sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026305/zl2135Isup2.hkl

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

C20H16N2O4·C7H8	F000 = 928
Mr = 440.48	Dx = 1.380 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5653 reflections
a = 11.9753 (3) Å	θ = 2.4–29.6º
b = 18.8539 (5) Å	µ = 0.09 mm−1
c = 9.9240 (2) Å	T = 100.0 (1) K
β = 108.819 (1)º	Plate, yellow
V = 2120.87 (9) Å3	0.25 × 0.13 × 0.02 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	6233 independent reflections
Radiation source: fine-focus sealed tube	4023 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.039
T = 100.0(1) K	θmax = 30.2º
φ and ω scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −14→16
Tmin = 0.954, Tmax = 0.994	k = −20→26
24830 measured reflections	l = −13→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058	H-atom parameters constrained
wR(F2) = 0.163	w = 1/[σ2(Fo2) + (0.0708P)2 + 0.4015P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
6233 reflections	Δρmax = 0.76 e Å−3
299 parameters	Δρmin = −0.32 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
N1	0.18268 (12)	0.42566 (7)	0.14400 (14)	0.0168 (3)
O3	0.50774 (11)	0.63459 (6)	0.61784 (12)	0.0214 (3)
H1O3	0.5724	0.6608	0.6044	0.032*
O1	0.23309 (11)	0.45373 (6)	0.41957 (12)	0.0225 (3)
H1O1	0.2053	0.4270	0.3349	0.034*
O4	0.48126 (11)	0.07727 (6)	0.62444 (12)	0.0217 (3)
H1O4	0.4999	0.0995	0.7096	0.033*
O2	0.31282 (10)	0.29118 (6)	0.39178 (12)	0.0187 (3)
N2	0.17826 (12)	0.28136 (7)	0.12862 (14)	0.0170 (3)
H1N2	0.2152	0.3043	0.2079	0.025*
C8	0.11363 (14)	0.39346 (9)	0.01527 (17)	0.0165 (3)
C6	0.31241 (14)	0.51993 (9)	0.26313 (17)	0.0161 (3)
C15	0.27803 (14)	0.18211 (9)	0.26242 (17)	0.0165 (3)
C13	0.10818 (14)	0.31889 (9)	0.00863 (17)	0.0164 (3)
C16	0.30131 (15)	0.10819 (9)	0.26262 (18)	0.0194 (4)
H16A	0.2684	0.0818	0.1775	0.023*
C7	0.24537 (14)	0.48061 (9)	0.13868 (17)	0.0165 (3)
H7A	0.2475	0.4959	0.0483	0.020*
C9	0.04597 (15)	0.43207 (9)	−0.10182 (17)	0.0193 (4)
H9A	0.0487	0.4824	−0.0988	0.023*
C19	0.39752 (15)	0.18616 (9)	0.51268 (17)	0.0177 (3)
H19A	0.4305	0.2113	0.5994	0.021*
C5	0.38949 (15)	0.57342 (8)	0.25065 (17)	0.0176 (4)
H5A	0.3961	0.5834	0.1597	0.021*
C1	0.30495 (14)	0.50578 (8)	0.39969 (17)	0.0163 (3)
C17	0.36973 (15)	0.07431 (9)	0.38208 (18)	0.0198 (4)
H17A	0.3853	0.0250	0.3804	0.024*
C18	0.41709 (15)	0.11407 (9)	0.50847 (17)	0.0176 (3)
C2	0.36978 (14)	0.54490 (9)	0.51645 (17)	0.0175 (4)
H2A	0.3627	0.5358	0.6075	0.021*
C12	0.03656 (15)	0.28533 (9)	−0.11326 (17)	0.0204 (4)
H12A	0.0333	0.2350	−0.1173	0.024*
C20	0.32949 (14)	0.22283 (9)	0.39033 (17)	0.0164 (3)
C4	0.45602 (15)	0.61205 (9)	0.36648 (17)	0.0185 (4)
H4A	0.5083	0.6479	0.3559	0.022*
C14	0.20597 (15)	0.21362 (9)	0.13726 (17)	0.0176 (4)
H14A	0.1756	0.1849	0.0548	0.021*
C10	−0.02551 (15)	0.39818 (10)	−0.22315 (18)	0.0225 (4)
H10A	−0.0714	0.4253	−0.3024	0.027*
C3	0.44526 (14)	0.59760 (9)	0.49988 (17)	0.0168 (3)
C11	−0.02984 (15)	0.32460 (10)	−0.22838 (18)	0.0231 (4)
H11A	−0.0786	0.3013	−0.3114	0.028*
C23	0.30310 (18)	0.71109 (11)	0.7808 (2)	0.0329 (5)
H23A	0.3583	0.7384	0.7523	0.040*
C25	0.2145 (2)	0.67854 (11)	0.9559 (2)	0.0352 (5)
H25A	0.2093	0.6830	1.0490	0.042*
C26	0.13983 (19)	0.63297 (10)	0.8595 (2)	0.0314 (5)
H26A	0.0822	0.6073	0.8867	0.038*
C22	0.22868 (18)	0.66449 (10)	0.6864 (2)	0.0293 (4)
H22A	0.2339	0.6604	0.5932	0.035*
C21	0.14696 (17)	0.62366 (10)	0.7224 (2)	0.0292 (4)
C24	0.29687 (18)	0.71778 (11)	0.9173 (2)	0.0350 (5)
H24A	0.3487	0.7490	0.9837	0.042*
C27	0.0688 (2)	0.57353 (12)	0.6196 (2)	0.0402 (5)
H27A	0.1166	0.5365	0.5954	0.060*
H27B	0.0242	0.5992	0.5331	0.060*
H27C	0.0139	0.5517	0.6622	0.060*

	U11	U22	U33	U12	U13	U23
N1	0.0194 (7)	0.0153 (7)	0.0144 (7)	0.0009 (6)	0.0036 (6)	−0.0015 (5)
O3	0.0251 (7)	0.0191 (6)	0.0189 (6)	−0.0058 (5)	0.0056 (5)	−0.0025 (5)
O1	0.0294 (7)	0.0215 (7)	0.0167 (6)	−0.0103 (5)	0.0076 (5)	−0.0025 (5)
O4	0.0273 (7)	0.0183 (6)	0.0174 (6)	0.0051 (5)	0.0043 (5)	0.0029 (5)
O2	0.0224 (6)	0.0131 (6)	0.0187 (6)	−0.0011 (5)	0.0039 (5)	−0.0009 (5)
N2	0.0183 (7)	0.0169 (7)	0.0137 (7)	−0.0029 (6)	0.0025 (6)	−0.0007 (5)
C8	0.0163 (8)	0.0201 (9)	0.0131 (8)	−0.0010 (7)	0.0048 (6)	−0.0024 (6)
C6	0.0180 (8)	0.0144 (8)	0.0150 (8)	0.0017 (6)	0.0040 (6)	−0.0004 (6)
C15	0.0189 (8)	0.0162 (8)	0.0163 (8)	−0.0011 (7)	0.0082 (7)	−0.0006 (6)
C13	0.0152 (8)	0.0170 (8)	0.0172 (8)	0.0002 (6)	0.0053 (7)	0.0015 (6)
C16	0.0261 (9)	0.0173 (9)	0.0168 (8)	−0.0008 (7)	0.0099 (7)	−0.0025 (7)
C7	0.0188 (8)	0.0165 (8)	0.0139 (8)	0.0033 (7)	0.0047 (7)	0.0005 (6)
C9	0.0218 (9)	0.0181 (9)	0.0169 (8)	0.0033 (7)	0.0047 (7)	0.0013 (7)
C19	0.0196 (8)	0.0176 (9)	0.0151 (8)	−0.0014 (7)	0.0044 (7)	−0.0009 (6)
C5	0.0212 (9)	0.0157 (8)	0.0168 (8)	0.0027 (7)	0.0073 (7)	0.0031 (6)
C1	0.0180 (8)	0.0133 (8)	0.0174 (8)	0.0012 (6)	0.0055 (7)	0.0008 (6)
C17	0.0259 (9)	0.0148 (8)	0.0214 (9)	0.0022 (7)	0.0115 (7)	0.0005 (7)
C18	0.0179 (8)	0.0186 (9)	0.0177 (8)	0.0022 (7)	0.0077 (7)	0.0034 (7)
C2	0.0206 (9)	0.0162 (8)	0.0156 (8)	0.0005 (7)	0.0059 (7)	−0.0002 (6)
C12	0.0195 (9)	0.0194 (9)	0.0205 (9)	−0.0045 (7)	0.0041 (7)	−0.0035 (7)
C20	0.0163 (8)	0.0161 (8)	0.0182 (8)	−0.0010 (6)	0.0074 (7)	0.0003 (6)
C4	0.0202 (9)	0.0143 (8)	0.0207 (9)	−0.0003 (7)	0.0062 (7)	0.0011 (7)
C14	0.0214 (9)	0.0156 (8)	0.0167 (8)	−0.0025 (7)	0.0074 (7)	−0.0007 (6)
C10	0.0197 (9)	0.0285 (10)	0.0159 (8)	0.0037 (7)	0.0012 (7)	0.0014 (7)
C3	0.0179 (8)	0.0142 (8)	0.0164 (8)	0.0008 (6)	0.0028 (7)	−0.0034 (6)
C11	0.0197 (9)	0.0291 (10)	0.0168 (9)	−0.0014 (8)	0.0009 (7)	−0.0037 (7)
C23	0.0296 (11)	0.0343 (12)	0.0362 (12)	0.0008 (9)	0.0124 (9)	0.0017 (9)
C25	0.0458 (13)	0.0309 (11)	0.0313 (11)	0.0098 (10)	0.0158 (10)	0.0044 (9)
C26	0.0341 (11)	0.0258 (11)	0.0402 (12)	0.0053 (9)	0.0201 (10)	0.0106 (9)
C22	0.0307 (11)	0.0280 (10)	0.0316 (11)	0.0033 (9)	0.0134 (9)	0.0029 (8)
C21	0.0292 (10)	0.0275 (10)	0.0311 (11)	0.0057 (8)	0.0101 (9)	0.0055 (8)
C24	0.0330 (11)	0.0363 (12)	0.0336 (11)	0.0063 (9)	0.0076 (9)	−0.0001 (9)
C27	0.0429 (13)	0.0380 (13)	0.0415 (13)	−0.0042 (10)	0.0161 (11)	0.0008 (10)

N1—C7	1.290 (2)	C5—H5A	0.9500
N1—C8	1.415 (2)	C1—C2	1.382 (2)
O3—C3	1.3608 (19)	C17—C18	1.413 (2)
O3—H1O3	0.9628	C17—H17A	0.9500
O1—C1	1.3608 (19)	C2—C3	1.388 (2)
O1—H1O1	0.9431	C2—H2A	0.9500
O4—C18	1.3513 (19)	C12—C11	1.378 (2)
O4—H1O4	0.9048	C12—H12A	0.9500
O2—C20	1.3048 (19)	C4—C3	1.398 (2)
N2—C14	1.315 (2)	C4—H4A	0.9500
N2—C13	1.406 (2)	C14—H14A	0.9500
N2—H1N2	0.8816	C10—C11	1.389 (3)
C8—C9	1.389 (2)	C10—H10A	0.9500
C8—C13	1.408 (2)	C11—H11A	0.9500
C6—C5	1.399 (2)	C23—C22	1.380 (3)
C6—C1	1.412 (2)	C23—C24	1.387 (3)
C6—C7	1.442 (2)	C23—H23A	0.9500
C15—C14	1.396 (2)	C25—C26	1.379 (3)
C15—C16	1.421 (2)	C25—C24	1.382 (3)
C15—C20	1.441 (2)	C25—H25A	0.9500
C13—C12	1.389 (2)	C26—C21	1.402 (3)
C16—C17	1.363 (2)	C26—H26A	0.9500
C16—H16A	0.9500	C22—C21	1.380 (3)
C7—H7A	0.9500	C22—H22A	0.9500
C9—C10	1.388 (2)	C21—C27	1.482 (3)
C9—H9A	0.9500	C24—H24A	0.9500
C19—C18	1.382 (2)	C27—H27A	0.9800
C19—C20	1.406 (2)	C27—H27B	0.9800
C19—H19A	0.9500	C27—H27C	0.9800
C5—C4	1.377 (2)
Cg1···Cg1i	3.7867 (1)	Cg2···Cg3ii	4.5626 (3)
C7—N1—C8	119.05 (14)	C11—C12—C13	120.40 (16)
C3—O3—H1O3	112.8	C11—C12—H12A	119.8
C1—O1—H1O1	108.3	C13—C12—H12A	119.8
C18—O4—H1O4	117.3	O2—C20—C19	121.60 (15)
C14—N2—C13	127.78 (14)	O2—C20—C15	120.84 (15)
C14—N2—H1N2	112.0	C19—C20—C15	117.56 (15)
C13—N2—H1N2	120.0	C5—C4—C3	118.85 (15)
C9—C8—C13	118.59 (15)	C5—C4—H4A	120.6
C9—C8—N1	122.94 (15)	C3—C4—H4A	120.6
C13—C8—N1	118.38 (14)	N2—C14—C15	122.80 (15)
C5—C6—C1	117.97 (15)	N2—C14—H14A	118.6
C5—C6—C7	119.71 (14)	C15—C14—H14A	118.6
C1—C6—C7	122.32 (15)	C9—C10—C11	119.84 (16)
C14—C15—C16	118.90 (15)	C9—C10—H10A	120.1
C14—C15—C20	121.53 (15)	C11—C10—H10A	120.1
C16—C15—C20	119.57 (15)	O3—C3—C2	117.60 (14)
C12—C13—N2	122.70 (15)	O3—C3—C4	121.45 (15)
C12—C13—C8	120.12 (15)	C2—C3—C4	120.95 (15)
N2—C13—C8	117.18 (14)	C12—C11—C10	120.08 (16)
C17—C16—C15	121.56 (15)	C12—C11—H11A	120.0
C17—C16—H16A	119.2	C10—C11—H11A	120.0
C15—C16—H16A	119.2	C22—C23—C24	119.6 (2)
N1—C7—C6	123.24 (15)	C22—C23—H23A	120.2
N1—C7—H7A	118.4	C24—C23—H23A	120.2
C6—C7—H7A	118.4	C26—C25—C24	120.16 (19)
C10—C9—C8	120.97 (16)	C26—C25—H25A	119.9
C10—C9—H9A	119.5	C24—C25—H25A	119.9
C8—C9—H9A	119.5	C25—C26—C21	121.50 (19)
C18—C19—C20	120.93 (15)	C25—C26—H26A	119.3
C18—C19—H19A	119.5	C21—C26—H26A	119.3
C20—C19—H19A	119.5	C21—C22—C23	122.41 (19)
C4—C5—C6	121.86 (15)	C21—C22—H22A	118.8
C4—C5—H5A	119.1	C23—C22—H22A	118.8
C6—C5—H5A	119.1	C22—C21—C26	116.88 (19)
O1—C1—C2	118.28 (14)	C22—C21—C27	121.39 (18)
O1—C1—C6	120.95 (14)	C26—C21—C27	121.72 (19)
C2—C1—C6	120.77 (15)	C25—C24—C23	119.4 (2)
C16—C17—C18	118.67 (16)	C25—C24—H24A	120.3
C16—C17—H17A	120.7	C23—C24—H24A	120.3
C18—C17—H17A	120.7	C21—C27—H27A	109.5
O4—C18—C19	122.31 (15)	C21—C27—H27B	109.5
O4—C18—C17	116.02 (15)	H27A—C27—H27B	109.5
C19—C18—C17	121.66 (15)	C21—C27—H27C	109.5
C1—C2—C3	119.59 (15)	H27A—C27—H27C	109.5
C1—C2—H2A	120.2	H27B—C27—H27C	109.5
C3—C2—H2A	120.2
C7—N1—C8—C9	−43.9 (2)	N2—C13—C12—C11	−179.57 (15)
C7—N1—C8—C13	139.83 (16)	C8—C13—C12—C11	−0.2 (2)
C14—N2—C13—C12	14.2 (3)	C18—C19—C20—O2	−178.20 (15)
C14—N2—C13—C8	−165.19 (16)	C18—C19—C20—C15	2.0 (2)
C9—C8—C13—C12	0.2 (2)	C14—C15—C20—O2	−2.0 (2)
N1—C8—C13—C12	176.67 (14)	C16—C15—C20—O2	177.67 (15)
C9—C8—C13—N2	179.64 (14)	C14—C15—C20—C19	177.82 (15)
N1—C8—C13—N2	−3.9 (2)	C16—C15—C20—C19	−2.5 (2)
C14—C15—C16—C17	−179.13 (15)	C6—C5—C4—C3	−0.5 (2)
C20—C15—C16—C17	1.2 (2)	C13—N2—C14—C15	179.10 (15)
C8—N1—C7—C6	175.76 (15)	C16—C15—C14—N2	178.73 (15)
C5—C6—C7—N1	172.13 (15)	C20—C15—C14—N2	−1.6 (2)
C1—C6—C7—N1	−6.8 (3)	C8—C9—C10—C11	−0.1 (3)
C13—C8—C9—C10	−0.1 (2)	C1—C2—C3—O3	−179.73 (14)
N1—C8—C9—C10	−176.39 (15)	C1—C2—C3—C4	0.5 (2)
C1—C6—C5—C4	−0.5 (2)	C5—C4—C3—O3	−179.24 (15)
C7—C6—C5—C4	−179.50 (15)	C5—C4—C3—C2	0.5 (2)
C5—C6—C1—O1	−178.99 (14)	C13—C12—C11—C10	0.0 (3)
C7—C6—C1—O1	0.0 (2)	C9—C10—C11—C12	0.1 (3)
C5—C6—C1—C2	1.6 (2)	C24—C25—C26—C21	1.7 (3)
C7—C6—C1—C2	−179.48 (15)	C24—C23—C22—C21	0.1 (3)
C15—C16—C17—C18	0.7 (2)	C23—C22—C21—C26	1.9 (3)
C20—C19—C18—O4	−179.47 (15)	C23—C22—C21—C27	−179.43 (19)
C20—C19—C18—C17	−0.1 (2)	C25—C26—C21—C22	−2.7 (3)
C16—C17—C18—O4	178.10 (14)	C25—C26—C21—C27	178.57 (19)
C16—C17—C18—C19	−1.3 (2)	C26—C25—C24—C23	0.4 (3)
O1—C1—C2—C3	178.99 (15)	C22—C23—C24—C25	−1.2 (3)
C6—C1—C2—C3	−1.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.94	1.83	2.6568 (17)	145
O3—H1O3···O2i	0.96	1.64	2.5919 (18)	171
O4—H1O4···O3iii	0.90	1.87	2.7403 (16)	162
N2—H1N2···O2	0.88	1.84	2.5954 (18)	143
N2—H1N2···N1	0.88	2.37	2.7245 (19)	104
C16—H16A···O1iv	0.95	2.55	3.439 (2)	157
C17—H17A···O4v	0.95	2.51	3.381 (2)	152
C11—H11A···Cg4vi	0.95	2.97	3.619 (2)	126

Table 1

Selected centroid⋯centroid distances (Å)

Cg1⋯Cg1i	3.7867 (1)
Cg2⋯Cg3ii	4.5626 (3)

Symmetry codes: (i) ; (ii) . Cg1, Cg2, and Cg3 are the centroids of the C1–C6, C8–C13 and C15–C20 benzene rings, respectively.

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1	0.94	1.83	2.6568 (17)	145
O3—H1O3⋯O2i	0.96	1.64	2.5919 (18)	171
O4—H1O4⋯O3iii	0.90	1.87	2.7403 (16)	162
N2—H1N2⋯O2	0.88	1.84	2.5954 (18)	143
N2—H1N2⋯N1	0.88	2.37	2.7245 (19)	104
C16—H16A⋯O1iv	0.95	2.55	3.439 (2)	157
C17—H17A⋯O4v	0.95	2.51	3.381 (2)	152
C11—H11A⋯Cg4vi	0.95	2.97	3.619 (2)	126

Symmetry codes: (i) ; (iii) ; (iv) ; (v) ; (vi) . Cg4 is the centroid of the C21–C26 benzene ring.