1-[4-({4-[(E)-(2-Hy-droxy-naphthalen-1-yl)methyl-idene-amino]-phen-yl}sulfan-yl)phen-yl]ethanone.

The title Schiff base compound, C25H19NO2S, crystallizes in a statistically disordered structure comprising keto and enol tautomeric forms. In the enol form, the benzenoid arrangment is promoted by a strong intra-molecular O-H⋯N hydrogen bond and adopts an E conformation about the imine bond. In the keto form there is an intramolecular N-H⋯O hydrogen bond. In the crystal, an extended network of C-H⋯O hydrogen bonds stabilizes columns parallel to the c axis, forming large voids (there are four cavities of 108 Å(3) per unit cell) with highly disordered residual electron density. The SQUEEZE procedure in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148-155] was used to eliminate the contribution of this electron density from the intensity data, and the solvent-free model was employed for the final refinement. The contribution of this undetermined solvent was ignored in the calculation of the unit-cell characteristics.

Related literature

For related structures, see: Blagus & Kaitner (2011 ▶); Farag et al. (2010 ▶); Venkatachalam et al. (2011 ▶). For background to Schiff bases and their applications, see: Li et al. (2003 ▶); Villar et al. (2004 ▶); Kagkelari et al. (2009 ▶); Ourari et al. (2008 ▶); Zidane et al. (2011 ▶).

Experimental

Crystal data

C25H19NO2S

M = 397.47

Monoclinic,

a = 10.695 (3) Å

b = 44.458 (14) Å

c = 4.4437 (11) Å

β = 99.004 (9)°

V = 2086.8 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 150 K

0.58 × 0.17 × 0.06 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.898, T max = 0.990

8026 measured reflections

3680 independent reflections

2952 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.125

S = 0.98

3680 reflections

263 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 1291 Friedel pairs

Flack parameter: −0.06 (10)

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812049835/tk5178sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049835/tk5178Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049835/tk5178Isup3.cml

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

C25H19NO2S	F(000) = 832
Mr = 397.47	Dx = 1.265 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1817 reflections
a = 10.695 (3) Å	θ = 2.4–26.0°
b = 44.458 (14) Å	µ = 0.18 mm−1
c = 4.4437 (11) Å	T = 150 K
β = 99.004 (9)°	Stick, orange
V = 2086.8 (10) Å3	0.58 × 0.17 × 0.06 mm
Z = 4

Bruker APEXII diffractometer	2952 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS, Sheldrick, 2002)	h = −12→13
Tmin = 0.898, Tmax = 0.990	k = −57→57
8026 measured reflections	l = −4→5
3680 independent reflections

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.0718P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max = 0.005
3680 reflections	Δρmax = 0.24 e Å−3
263 parameters	Δρmin = −0.22 e Å−3
2 restraints	Absolute structure: Flack (1983), 1291 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.06 (10)

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.Since hydrogen is not very well localized between N13 and O1, the structure is described as the presence of two tautomers. Hydrogen is bonded to O1 in the first one (part A) and to N13 in the second (part B). This disorder was modeled by refining part A (except H on N13) and part B (except H on O1) with equivalence of N13 and central phenyl ring (C14 to C19) atoms.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	0.9261 (2)	0.89274 (5)	0.2227 (5)	0.0432 (6)	0.5
H1A	0.8804	0.8781	0.2548	0.065*	0.5
O1B	0.9261 (2)	0.89274 (5)	0.2227 (5)	0.0432 (6)	0.5
C2	0.8665 (3)	0.90927 (7)	0.0128 (7)	0.0343 (7)
C3	0.9267 (3)	0.93567 (7)	−0.0798 (8)	0.0404 (8)
H3	1.0096	0.9405	0.0187	0.048*
C4	0.8695 (3)	0.95396 (7)	−0.3033 (8)	0.0404 (8)
H4	0.9135	0.9711	−0.3594	0.048*
C5	0.7436 (3)	0.94802 (7)	−0.4576 (7)	0.0339 (7)
C6	0.6843 (4)	0.96779 (7)	−0.6875 (8)	0.0402 (8)
H6	0.7291	0.9849	−0.7408	0.048*
C7	0.5643 (3)	0.96264 (7)	−0.8334 (7)	0.0423 (9)
H7	0.5253	0.9761	−0.9862	0.051*
C8	0.4992 (4)	0.93702 (8)	−0.7531 (7)	0.0408 (8)
H8	0.4155	0.9332	−0.853	0.049*
C9	0.5551 (3)	0.91739 (7)	−0.5316 (8)	0.0357 (7)
H9	0.5092	0.9003	−0.4825	0.043*
C10	0.6785 (3)	0.92219 (6)	−0.3773 (7)	0.0317 (7)
C11	0.7411 (3)	0.90245 (6)	−0.1401 (7)	0.0306 (7)
C12	0.6792 (3)	0.87685 (7)	−0.0513 (7)	0.0321 (7)
H12	0.5963	0.8725	−0.153	0.039*
N13A	0.7319 (3)	0.85845 (5)	0.1698 (6)	0.0320 (6)	0.5
C14A	0.6753 (3)	0.83248 (6)	0.2696 (7)	0.0285 (6)	0.5
C15A	0.7471 (3)	0.81538 (7)	0.4960 (7)	0.0325 (7)	0.5
H15A	0.8306	0.8216	0.5776	0.039*	0.5
C16A	0.6980 (3)	0.78934 (7)	0.6035 (7)	0.0343 (7)	0.5
H16A	0.7467	0.7782	0.7626	0.041*	0.5
C17A	0.5781 (3)	0.77958 (6)	0.4798 (7)	0.0296 (7)	0.5
C18A	0.5070 (3)	0.79663 (7)	0.2544 (7)	0.0324 (7)	0.5
H18A	0.4242	0.7901	0.1706	0.039*	0.5
C19A	0.5541 (3)	0.82303 (7)	0.1483 (7)	0.0345 (7)	0.5
H19A	0.504	0.8345	−0.0058	0.041*	0.5
N13B	0.7319 (3)	0.85845 (5)	0.1698 (6)	0.0320 (6)	0.5
H13B	0.8087	0.8629	0.2611	0.038*	0.5
C14B	0.6753 (3)	0.83248 (6)	0.2696 (7)	0.0285 (6)	0.5
C15B	0.7471 (3)	0.81538 (7)	0.4960 (7)	0.0325 (7)	0.5
H15B	0.8306	0.8216	0.5776	0.039*	0.5
C16B	0.6980 (3)	0.78934 (7)	0.6035 (7)	0.0343 (7)	0.5
H16B	0.7467	0.7782	0.7626	0.041*	0.5
C17B	0.5781 (3)	0.77958 (6)	0.4798 (7)	0.0296 (7)	0.5
C18B	0.5070 (3)	0.79663 (7)	0.2544 (7)	0.0324 (7)	0.5
H18B	0.4242	0.7901	0.1706	0.039*	0.5
C19B	0.5541 (3)	0.82303 (7)	0.1483 (7)	0.0345 (7)	0.5
H19B	0.504	0.8345	−0.0058	0.041*	0.5
S1	0.50675 (10)	0.747532 (16)	0.62296 (19)	0.0362 (2)
C20	0.5814 (3)	0.71639 (6)	0.4809 (7)	0.0288 (7)
C21	0.5376 (3)	0.68797 (7)	0.5525 (7)	0.0342 (7)
H21	0.47	0.6864	0.6674	0.041*
C22	0.5921 (3)	0.66202 (7)	0.4567 (7)	0.0344 (7)
H22	0.5608	0.6429	0.5051	0.041*
C23	0.6915 (3)	0.66362 (7)	0.2916 (7)	0.0309 (7)
C24	0.7347 (3)	0.69227 (7)	0.2182 (7)	0.0317 (7)
H24	0.8024	0.6938	0.1038	0.038*
C25	0.6800 (3)	0.71807 (7)	0.3103 (7)	0.0305 (7)
H25	0.7098	0.7372	0.257	0.037*
C26	0.7554 (3)	0.63638 (7)	0.1932 (8)	0.0367 (8)
C27	0.7015 (4)	0.60589 (7)	0.2401 (9)	0.0474 (9)
H27A	0.7546	0.5904	0.1671	0.071*
H27B	0.6154	0.6046	0.1264	0.071*
H27C	0.6992	0.6028	0.4576	0.071*
O28	0.8519 (3)	0.63891 (6)	0.0759 (6)	0.0530 (7)

	U11	U22	U33	U12	U13	U23
O1A	0.0444 (14)	0.0349 (12)	0.0494 (16)	0.0022 (10)	0.0045 (11)	−0.0044 (10)
O1B	0.0444 (14)	0.0349 (12)	0.0494 (16)	0.0022 (10)	0.0045 (11)	−0.0044 (10)
C2	0.044 (2)	0.0286 (16)	0.032 (2)	0.0051 (14)	0.0121 (14)	−0.0093 (13)
C3	0.0406 (19)	0.0355 (17)	0.047 (2)	−0.0029 (15)	0.0120 (16)	−0.0151 (15)
C4	0.048 (2)	0.0319 (16)	0.046 (2)	−0.0078 (15)	0.0241 (17)	−0.0102 (15)
C5	0.048 (2)	0.0278 (15)	0.0299 (19)	−0.0021 (14)	0.0177 (14)	−0.0072 (12)
C6	0.064 (2)	0.0293 (16)	0.0320 (19)	−0.0051 (15)	0.0218 (16)	−0.0041 (13)
C7	0.061 (2)	0.0339 (17)	0.033 (2)	−0.0001 (16)	0.0109 (17)	0.0036 (14)
C8	0.049 (2)	0.0396 (18)	0.034 (2)	0.0013 (15)	0.0062 (16)	−0.0023 (14)
C9	0.048 (2)	0.0294 (15)	0.0310 (18)	−0.0037 (14)	0.0092 (14)	−0.0008 (13)
C10	0.0457 (19)	0.0240 (13)	0.0287 (18)	−0.0010 (13)	0.0159 (14)	−0.0066 (12)
C11	0.0410 (18)	0.0249 (14)	0.0279 (17)	−0.0011 (13)	0.0112 (13)	−0.0068 (12)
C12	0.0397 (18)	0.0296 (15)	0.0279 (18)	0.0039 (13)	0.0082 (13)	−0.0055 (12)
N13A	0.0375 (14)	0.0286 (13)	0.0308 (15)	0.0022 (11)	0.0082 (11)	−0.0019 (11)
C14A	0.0362 (17)	0.0263 (14)	0.0248 (17)	0.0041 (12)	0.0101 (12)	−0.0052 (12)
C15A	0.0359 (18)	0.0332 (16)	0.0278 (19)	0.0001 (13)	0.0034 (13)	−0.0021 (12)
C16A	0.0368 (18)	0.0370 (17)	0.0284 (19)	0.0042 (14)	0.0029 (14)	0.0051 (13)
C17A	0.0358 (18)	0.0267 (14)	0.0270 (18)	0.0034 (12)	0.0069 (13)	0.0017 (12)
C18A	0.0342 (17)	0.0327 (16)	0.0312 (19)	0.0045 (13)	0.0078 (13)	−0.0033 (12)
C19A	0.0403 (18)	0.0311 (16)	0.0311 (19)	0.0048 (13)	0.0030 (14)	0.0036 (13)
N13B	0.0375 (14)	0.0286 (13)	0.0308 (15)	0.0022 (11)	0.0082 (11)	−0.0019 (11)
C14B	0.0362 (17)	0.0263 (14)	0.0248 (17)	0.0041 (12)	0.0101 (12)	−0.0052 (12)
C15B	0.0359 (18)	0.0332 (16)	0.0278 (19)	0.0001 (13)	0.0034 (13)	−0.0021 (12)
C16B	0.0368 (18)	0.0370 (17)	0.0284 (19)	0.0042 (14)	0.0029 (14)	0.0051 (13)
C17B	0.0358 (18)	0.0267 (14)	0.0270 (18)	0.0034 (12)	0.0069 (13)	0.0017 (12)
C18B	0.0342 (17)	0.0327 (16)	0.0312 (19)	0.0045 (13)	0.0078 (13)	−0.0033 (12)
C19B	0.0403 (18)	0.0311 (16)	0.0311 (19)	0.0048 (13)	0.0030 (14)	0.0036 (13)
S1	0.0411 (4)	0.0342 (4)	0.0357 (5)	0.0028 (4)	0.0138 (3)	0.0048 (4)
C20	0.0311 (16)	0.0305 (15)	0.0233 (18)	0.0001 (12)	−0.0005 (12)	0.0028 (12)
C21	0.0350 (18)	0.0354 (17)	0.033 (2)	−0.0023 (13)	0.0092 (13)	0.0063 (13)
C22	0.0394 (18)	0.0310 (16)	0.0326 (19)	−0.0070 (13)	0.0047 (14)	0.0037 (13)
C23	0.0325 (17)	0.0294 (15)	0.0297 (18)	−0.0039 (12)	0.0018 (13)	0.0025 (12)
C24	0.0325 (17)	0.0331 (16)	0.0296 (19)	−0.0035 (13)	0.0049 (13)	0.0028 (13)
C25	0.0337 (17)	0.0284 (15)	0.0297 (18)	−0.0010 (12)	0.0062 (13)	0.0047 (12)
C26	0.0362 (19)	0.0362 (17)	0.035 (2)	0.0004 (14)	−0.0013 (14)	0.0015 (14)
C27	0.052 (2)	0.0334 (17)	0.057 (3)	0.0055 (16)	0.0088 (17)	0.0002 (16)
O28	0.0506 (16)	0.0421 (14)	0.0705 (18)	0.0027 (12)	0.0222 (13)	−0.0073 (13)

O1A—C2	1.277 (4)	C15A—H15A	0.95
O1A—H1A	0.84	C16A—C17A	1.383 (5)
C2—C3	1.429 (4)	C16A—H16A	0.95
C2—C11	1.438 (5)	C17A—C18A	1.385 (4)
C3—C4	1.354 (5)	C17A—S1	1.780 (3)
C3—H3	0.95	C18A—C19A	1.389 (4)
C4—C5	1.437 (5)	C18A—H18A	0.95
C4—H4	0.95	C19A—H19A	0.95
C5—C10	1.417 (4)	S1—C20	1.764 (3)
C5—C6	1.420 (5)	C20—C25	1.394 (4)
C6—C7	1.363 (5)	C20—C21	1.401 (4)
C6—H6	0.95	C21—C22	1.389 (4)
C7—C8	1.410 (5)	C21—H21	0.95
C7—H7	0.95	C22—C23	1.385 (5)
C8—C9	1.380 (5)	C22—H22	0.95
C8—H8	0.95	C23—C24	1.410 (4)
C9—C10	1.404 (5)	C23—C26	1.489 (4)
C9—H9	0.95	C24—C25	1.378 (4)
C10—C11	1.453 (4)	C24—H24	0.95
C11—C12	1.404 (4)	C25—H25	0.95
C12—N13A	1.334 (4)	C26—O28	1.232 (4)
C12—H12	0.95	C26—C27	1.500 (4)
N13A—C14A	1.407 (4)	C27—H27A	0.98
C14A—C19A	1.388 (4)	C27—H27B	0.98
C14A—C15A	1.393 (5)	C27—H27C	0.98
C15A—C16A	1.387 (4)
C2—O1A—H1A	109.5	C17A—C16A—C15A	120.2 (3)
O1A—C2—C3	119.1 (3)	C17A—C16A—H16A	119.9
O1A—C2—C11	123.1 (3)	C15A—C16A—H16A	119.9
C3—C2—C11	117.8 (3)	C16A—C17A—C18A	119.1 (3)
C4—C3—C2	122.1 (3)	C16A—C17A—S1	122.1 (2)
C4—C3—H3	118.9	C18A—C17A—S1	118.6 (2)
C2—C3—H3	118.9	C17A—C18A—C19A	121.3 (3)
C3—C4—C5	121.5 (3)	C17A—C18A—H18A	119.3
C3—C4—H4	119.3	C19A—C18A—H18A	119.3
C5—C4—H4	119.3	C18A—C19A—C14A	119.4 (3)
C10—C5—C6	120.1 (3)	C18A—C19A—H19A	120.3
C10—C5—C4	119.3 (3)	C14A—C19A—H19A	120.3
C6—C5—C4	120.6 (3)	C20—S1—C17A	104.88 (15)
C7—C6—C5	121.3 (3)	C25—C20—C21	118.7 (3)
C7—C6—H6	119.4	C25—C20—S1	125.2 (2)
C5—C6—H6	119.4	C21—C20—S1	116.1 (2)
C6—C7—C8	118.7 (3)	C22—C21—C20	120.5 (3)
C6—C7—H7	120.6	C22—C21—H21	119.8
C8—C7—H7	120.6	C20—C21—H21	119.8
C9—C8—C7	121.0 (3)	C23—C22—C21	120.9 (3)
C9—C8—H8	119.5	C23—C22—H22	119.5
C7—C8—H8	119.5	C21—C22—H22	119.5
C8—C9—C10	121.4 (3)	C22—C23—C24	118.3 (3)
C8—C9—H9	119.3	C22—C23—C26	122.6 (3)
C10—C9—H9	119.3	C24—C23—C26	119.0 (3)
C9—C10—C5	117.5 (3)	C25—C24—C23	120.9 (3)
C9—C10—C11	123.6 (3)	C25—C24—H24	119.5
C5—C10—C11	118.9 (3)	C23—C24—H24	119.5
C12—C11—C2	119.0 (3)	C24—C25—C20	120.6 (3)
C12—C11—C10	120.6 (3)	C24—C25—H25	119.7
C2—C11—C10	120.4 (3)	C20—C25—H25	119.7
N13A—C12—C11	122.7 (3)	O28—C26—C23	120.2 (3)
N13A—C12—H12	118.7	O28—C26—C27	120.4 (3)
C11—C12—H12	118.7	C23—C26—C27	119.3 (3)
C12—N13A—C14A	125.6 (3)	C26—C27—H27A	109.5
C19A—C14A—C15A	119.4 (3)	C26—C27—H27B	109.5
C19A—C14A—N13A	123.2 (3)	H27A—C27—H27B	109.5
C15A—C14A—N13A	117.4 (3)	C26—C27—H27C	109.5
C16A—C15A—C14A	120.6 (3)	H27A—C27—H27C	109.5
C16A—C15A—H15A	119.7	H27B—C27—H27C	109.5
C14A—C15A—H15A	119.7
O1A—C2—C3—C4	179.2 (3)	C19A—C14A—C15A—C16A	−0.9 (5)
C11—C2—C3—C4	0.0 (4)	N13A—C14A—C15A—C16A	−179.4 (3)
C2—C3—C4—C5	0.9 (5)	C14A—C15A—C16A—C17A	2.0 (5)
C3—C4—C5—C10	−0.9 (5)	C15A—C16A—C17A—C18A	−1.9 (5)
C3—C4—C5—C6	178.8 (3)	C15A—C16A—C17A—S1	−176.4 (2)
C10—C5—C6—C7	0.6 (5)	C16A—C17A—C18A—C19A	0.8 (5)
C4—C5—C6—C7	−179.2 (3)	S1—C17A—C18A—C19A	175.5 (2)
C5—C6—C7—C8	−0.3 (5)	C17A—C18A—C19A—C14A	0.3 (5)
C6—C7—C8—C9	−0.1 (5)	C15A—C14A—C19A—C18A	−0.2 (5)
C7—C8—C9—C10	0.2 (5)	N13A—C14A—C19A—C18A	178.1 (3)
C8—C9—C10—C5	0.0 (5)	C16A—C17A—S1—C20	−76.5 (3)
C8—C9—C10—C11	179.2 (3)	C18A—C17A—S1—C20	109.0 (3)
C6—C5—C10—C9	−0.4 (4)	C17A—S1—C20—C25	3.5 (3)
C4—C5—C10—C9	179.4 (3)	C17A—S1—C20—C21	−177.5 (2)
C6—C5—C10—C11	−179.7 (3)	C25—C20—C21—C22	0.4 (4)
C4—C5—C10—C11	0.1 (4)	S1—C20—C21—C22	−178.6 (3)
O1A—C2—C11—C12	1.6 (4)	C20—C21—C22—C23	0.7 (5)
C3—C2—C11—C12	−179.3 (3)	C21—C22—C23—C24	−1.1 (4)
O1A—C2—C11—C10	−180.0 (3)	C21—C22—C23—C26	178.0 (3)
C3—C2—C11—C10	−0.8 (4)	C22—C23—C24—C25	0.5 (4)
C9—C10—C11—C12	0.0 (5)	C26—C23—C24—C25	−178.7 (3)
C5—C10—C11—C12	179.2 (3)	C23—C24—C25—C20	0.6 (4)
C9—C10—C11—C2	−178.5 (3)	C21—C20—C25—C24	−1.1 (4)
C5—C10—C11—C2	0.8 (4)	S1—C20—C25—C24	177.9 (2)
C2—C11—C12—N13A	−0.1 (4)	C22—C23—C26—O28	−172.1 (3)
C10—C11—C12—N13A	−178.5 (3)	C24—C23—C26—O28	7.0 (4)
C11—C12—N13A—C14A	−180.0 (3)	C22—C23—C26—C27	7.5 (5)
C12—N13A—C14A—C19A	−0.8 (5)	C24—C23—C26—C27	−173.4 (3)
C12—N13A—C14A—C15A	177.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···N13A	0.84	1.80	2.558 (4)	149
N13B—H13B···O1B	0.88	1.85	2.558 (4)	136
C9—H9···O28i	0.95	2.46 (1)	3.398 (4)	168
C19A—H19A···O28i	0.95	2.56 (1)	3.506 (4)	174
C22—H22···O1Aii	0.95	2.44 (1)	3.337 (4)	157
C27—H27B···O1Ai	0.98	2.49 (1)	3.442 (4)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1A⋯N13A	0.84	1.80	2.558 (4)	149
N13B—H13B⋯O1B	0.88	1.85	2.558 (4)	136
C9—H9⋯O28i	0.95	2.46 (1)	3.398 (4)	168
C19A—H19A⋯O28i	0.95	2.56 (1)	3.506 (4)	174
C22—H22⋯O1A ii	0.95	2.44 (1)	3.337 (4)	157
C27—H27B⋯O1A i	0.98	2.49 (1)	3.442 (4)	164

Symmetry codes: (i) ; (ii) .