Crystal structure of 5-di-ethyl-amino-2-({[4-(di-ethyl-amino)-phen-yl]imino}-meth-yl)phenol.

In the title compound, C21H29N3O, the dihedral angle between the planes of the aromatic rings is 8.1 (2)°. The ethyl groups at one terminal site of the compound are disordered over two sets of sites with occupancies of 0.775 (9) and 0.225 (9). The mol-ecule has an E conformation about the N=C bond. The mol-ecular structure features an intra-molecular O-H⋯N hydrogen bond, which closes an S(6) loop. In the crystal, weak C-H⋯π inter-actions leads to the formation of a three-dimensional network.

Related literature

For biological and pharmacological activities of Schiff base compounds and their derivatives, see: Khandar et al. (2005 ▸); Chen et al. (2006 ▸); Kidwai et al. (2000 ▸). For similar structures, see: Manvizhi et al. (2011 ▸); Thirugnanasundar et al. (2011 ▸); Rani et al. (2015 ▸).

Experimental

Crystal data

C21H29N3O

M = 339.47

Orthorhombic,

a = 8.1986 (4) Å

b = 9.7128 (4) Å

c = 24.4172 (12) Å

V = 1944.38 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 295 K

0.28 × 0.26 × 0.24 mm

Data collection

Bruker Kappa APEX II CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▸) T min = 0.980, T max = 0.983

29557 measured reflections

3556 independent reflections

2130 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.205

S = 1.07

3556 reflections

272 parameters

10 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: SAINT (Bruker, 2004 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S205698901501645X/rk2432sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901501645X/rk2432Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S205698901501645X/rk2432Isup3.cml

Click here for additional data file.

2 5 2 . DOI: 10.1107/S205698901501645X/rk2432fig1.tif

The mol­ecular structure of title compaund, with the atom–numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius. The intra­molecular hydrogen bond is depicted by a dashed line. Only the major occupancy component of the disordered di­ethyl­amino–group [—N1(C2H5)2] is shown.

CCDC reference: 1422036

Additional supporting information: crystallographic information; 3D view; checkCIF report

C21H29N3O	F(000) = 736
Mr = 339.47	Dx = 1.160 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7089 reflections
a = 8.1986 (4) Å	θ = 2.5–25.3°
b = 9.7128 (4) Å	µ = 0.07 mm−1
c = 24.4172 (12) Å	T = 295 K
V = 1944.38 (16) Å3	Block, colourless
Z = 4	0.28 × 0.26 × 0.24 mm

Bruker Kappa APEX II CCD diffractometer	3556 independent reflections
Radiation source: fine–focus sealed tube	2130 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
ω and φ scans	θmax = 25.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.980, Tmax = 0.983	k = −11→11
29557 measured reflections	l = −29→29

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)] = 0.064	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.205	w = 1/[σ2(Fo2) + (0.0727P)2 + 1.5032P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3556 reflections	Δρmax = 0.44 e Å−3
272 parameters	Δρmin = −0.20 e Å−3
10 restraints	Absolute structure: Flack (1983), 1466 Friedel pairs
Primary atom site location: structure-invariant direct methods

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	Occ. (<1)
C1	0.7266 (10)	0.9101 (7)	−0.0244 (3)	0.084 (2)	0.775 (9)
H1A	0.7411	0.8690	0.0111	0.125*	0.775 (9)
H1B	0.6538	0.9871	−0.0214	0.125*	0.775 (9)
H1C	0.8302	0.9409	−0.0380	0.125*	0.775 (9)
C2	0.6555 (11)	0.8049 (8)	−0.0633 (4)	0.067 (3)	0.775 (9)
H2A	0.5577	0.7651	−0.0475	0.080*	0.775 (9)
H2B	0.6260	0.8492	−0.0975	0.080*	0.775 (9)
C3	0.9082 (10)	0.7205 (8)	−0.1156 (3)	0.073 (2)	0.775 (9)
H3A	0.9375	0.8172	−0.1161	0.088*	0.775 (9)
H3B	1.0047	0.6674	−0.1065	0.088*	0.775 (9)
C4	0.8438 (10)	0.6778 (8)	−0.1703 (3)	0.093 (3)	0.775 (9)
H4A	0.8211	0.5809	−0.1699	0.140*	0.775 (9)
H4B	0.9237	0.6975	−0.1979	0.140*	0.775 (9)
H4C	0.7454	0.7277	−0.1780	0.140*	0.775 (9)
C1A	0.586 (4)	0.847 (5)	−0.0615 (19)	0.122 (16)	0.225 (9)
H1A1	0.5521	0.9397	−0.0545	0.183*	0.225 (9)
H1A2	0.5193	0.7847	−0.0405	0.183*	0.225 (9)
H1A3	0.5730	0.8267	−0.0998	0.183*	0.225 (9)
C2A	0.764 (4)	0.8291 (15)	−0.0453 (9)	0.085 (9)	0.225 (9)
H2A1	0.8345	0.8993	−0.0607	0.102*	0.225 (9)
H2A2	0.7798	0.8221	−0.0061	0.102*	0.225 (9)
C3A	0.787 (3)	0.6858 (16)	−0.1341 (4)	0.061 (7)	0.225 (9)
H3A1	0.7019	0.7390	−0.1519	0.073*	0.225 (9)
H3A2	0.7824	0.5911	−0.1467	0.073*	0.225 (9)
C4A	0.955 (3)	0.749 (3)	−0.1425 (13)	0.080 (9)	0.225 (9)
H4A1	0.9478	0.8474	−0.1389	0.120*	0.225 (9)
H4A2	0.9944	0.7263	−0.1783	0.120*	0.225 (9)
H4A3	1.0288	0.7136	−0.1154	0.120*	0.225 (9)
C5	0.7811 (6)	0.5793 (4)	−0.04177 (17)	0.0666 (12)
C6	0.8764 (6)	0.4644 (5)	−0.05697 (19)	0.0725 (13)
H6	0.9326	0.4651	−0.0901	0.087*
C7	0.8865 (6)	0.3522 (5)	−0.02341 (19)	0.0680 (12)
H7	0.9509	0.2782	−0.0342	0.082*
C8	0.8054 (5)	0.3444 (4)	0.02559 (16)	0.0541 (10)
C9	0.7068 (6)	0.4550 (5)	0.03971 (16)	0.0613 (11)
C10	0.6941 (6)	0.5712 (4)	0.00699 (17)	0.0662 (12)
H10	0.6274	0.6438	0.0177	0.079*
C11	0.8246 (6)	0.2245 (5)	0.06113 (19)	0.0643 (12)
H11	0.8909	0.1522	0.0499	0.077*
C12	0.7727 (5)	0.1017 (4)	0.14256 (17)	0.0574 (11)
C13	0.8522 (6)	−0.0207 (5)	0.12960 (18)	0.0706 (13)
H13	0.9012	−0.0306	0.0955	0.085*
C14	0.8591 (6)	−0.1287 (5)	0.16721 (18)	0.0679 (12)
H14	0.9130	−0.2094	0.1577	0.082*
C15	0.7872 (5)	−0.1183 (4)	0.21878 (16)	0.0515 (10)
C16	0.7109 (5)	0.0078 (4)	0.23007 (17)	0.0616 (11)
H16	0.6638	0.0210	0.2643	0.074*
C17	0.7033 (5)	0.1122 (5)	0.19253 (18)	0.0622 (11)
H17	0.6487	0.1929	0.2017	0.075*
C18	0.8789 (6)	−0.3514 (5)	0.2453 (2)	0.0726 (13)
H18A	0.9128	−0.3912	0.2799	0.087*
H18B	0.9765	−0.3306	0.2244	0.087*
C19	0.7787 (9)	−0.4567 (6)	0.2141 (2)	0.109 (2)
H19A	0.6855	−0.4825	0.2356	0.164*
H19B	0.8443	−0.5366	0.2070	0.164*
H19C	0.7429	−0.4176	0.1801	0.164*
C20	0.7125 (6)	−0.2143 (5)	0.3091 (2)	0.0764 (14)
H20A	0.6822	−0.3058	0.3213	0.092*
H20B	0.6132	−0.1607	0.3054	0.092*
C21	0.8191 (9)	−0.1487 (7)	0.3515 (2)	0.113 (2)
H21A	0.9208	−0.1975	0.3535	0.170*
H21B	0.7657	−0.1521	0.3864	0.170*
H21C	0.8393	−0.0546	0.3417	0.170*
N1	0.7767 (7)	0.6954 (4)	−0.07378 (16)	0.1047 (19)
N2	0.7542 (4)	0.2174 (4)	0.10594 (14)	0.0626 (10)
N3	0.7918 (5)	−0.2243 (4)	0.25593 (14)	0.0654 (10)
O1	0.6208 (5)	0.4508 (4)	0.08624 (14)	0.0858 (11)
H1	0.643 (8)	0.379 (4)	0.105 (2)	0.129*

	U11	U22	U33	U12	U13	U23
C1	0.091 (5)	0.071 (5)	0.089 (5)	0.010 (4)	0.006 (4)	−0.013 (4)
C2	0.084 (8)	0.057 (5)	0.059 (4)	0.014 (5)	−0.005 (5)	0.004 (3)
C3	0.081 (6)	0.061 (4)	0.078 (6)	−0.007 (4)	0.005 (4)	0.004 (4)
C4	0.099 (6)	0.105 (6)	0.075 (5)	0.017 (5)	0.000 (4)	−0.008 (4)
C1A	0.11 (3)	0.11 (3)	0.15 (3)	−0.01 (2)	0.04 (3)	0.01 (3)
C2A	0.12 (3)	0.08 (2)	0.058 (16)	−0.004 (18)	−0.006 (17)	0.015 (14)
C3A	0.13 (2)	0.021 (8)	0.036 (11)	0.008 (11)	0.021 (12)	0.000 (7)
C4A	0.076 (17)	0.080 (19)	0.09 (2)	−0.020 (14)	0.023 (15)	−0.010 (16)
C5	0.091 (3)	0.054 (3)	0.055 (2)	0.012 (3)	0.019 (3)	0.003 (2)
C6	0.090 (4)	0.061 (3)	0.067 (3)	0.008 (3)	0.018 (3)	−0.006 (2)
C7	0.075 (3)	0.054 (3)	0.075 (3)	0.010 (2)	0.004 (3)	−0.005 (2)
C8	0.050 (2)	0.048 (2)	0.064 (3)	0.000 (2)	−0.010 (2)	0.0036 (19)
C9	0.059 (2)	0.071 (3)	0.054 (2)	−0.004 (2)	0.0005 (17)	0.001 (2)
C10	0.081 (3)	0.059 (3)	0.059 (2)	0.017 (3)	0.015 (2)	0.005 (2)
C11	0.056 (3)	0.071 (3)	0.065 (3)	−0.002 (2)	−0.012 (2)	−0.003 (2)
C12	0.052 (2)	0.049 (2)	0.071 (3)	0.000 (2)	−0.017 (2)	0.010 (2)
C13	0.081 (3)	0.080 (3)	0.050 (2)	−0.005 (3)	−0.002 (2)	0.002 (2)
C14	0.078 (3)	0.061 (3)	0.065 (3)	0.013 (2)	−0.007 (2)	0.006 (2)
C15	0.051 (2)	0.046 (2)	0.058 (2)	−0.002 (2)	−0.011 (2)	0.0053 (19)
C16	0.056 (2)	0.062 (3)	0.067 (3)	0.001 (2)	−0.003 (2)	0.004 (2)
C17	0.056 (3)	0.064 (3)	0.067 (3)	0.001 (2)	−0.006 (2)	0.002 (2)
C18	0.077 (3)	0.063 (3)	0.077 (3)	0.015 (3)	−0.004 (3)	0.014 (3)
C19	0.144 (6)	0.066 (3)	0.116 (4)	0.001 (4)	−0.014 (5)	−0.014 (3)
C20	0.073 (3)	0.063 (3)	0.093 (3)	−0.001 (3)	0.001 (3)	0.018 (3)
C21	0.145 (6)	0.123 (5)	0.072 (3)	−0.005 (5)	−0.001 (4)	−0.008 (3)
N1	0.176 (5)	0.065 (3)	0.072 (3)	0.038 (3)	0.061 (3)	0.020 (2)
N2	0.061 (2)	0.065 (2)	0.061 (2)	0.0032 (19)	−0.0139 (19)	−0.0030 (18)
N3	0.081 (2)	0.054 (2)	0.062 (2)	0.011 (2)	0.000 (2)	0.0053 (17)
O1	0.105 (3)	0.084 (2)	0.068 (2)	0.028 (2)	0.0249 (18)	0.0131 (18)

C1—C2	1.513 (8)	C8—C9	1.388 (6)
C1—H1A	0.9600	C8—C11	1.461 (6)
C1—H1B	0.9600	C9—O1	1.338 (5)
C1—H1C	0.9600	C9—C10	1.387 (6)
C2—N1	1.478 (7)	C10—H10	0.9300
C2—H2A	0.9700	C11—N2	1.239 (5)
C2—H2B	0.9700	C11—H11	0.9300
C3—C4	1.495 (7)	C12—C17	1.350 (6)
C3—N1	1.504 (7)	C12—C13	1.392 (6)
C3—H3A	0.9700	C12—N2	1.444 (5)
C3—H3B	0.9700	C13—C14	1.395 (6)
C4—H4A	0.9600	C13—H13	0.9300
C4—H4B	0.9600	C14—C15	1.394 (6)
C4—H4C	0.9600	C14—H14	0.9300
C1A—C2A	1.523 (10)	C15—N3	1.373 (5)
C1A—H1A1	0.9600	C15—C16	1.403 (6)
C1A—H1A2	0.9600	C16—C17	1.368 (6)
C1A—H1A3	0.9600	C16—H16	0.9300
C2A—N1	1.477 (10)	C17—H17	0.9300
C2A—H2A1	0.9700	C18—N3	1.450 (5)
C2A—H2A2	0.9700	C18—C19	1.516 (7)
C3A—N1	1.478 (9)	C18—H18A	0.9700
C3A—C4A	1.524 (10)	C18—H18B	0.9700
C3A—H3A1	0.9700	C19—H19A	0.9600
C3A—H3A2	0.9700	C19—H19B	0.9600
C4A—H4A1	0.9600	C19—H19C	0.9600
C4A—H4A2	0.9600	C20—N3	1.455 (6)
C4A—H4A3	0.9600	C20—C21	1.497 (7)
C5—N1	1.372 (5)	C20—H20A	0.9700
C5—C10	1.390 (6)	C20—H20B	0.9700
C5—C6	1.412 (6)	C21—H21A	0.9600
C6—C7	1.366 (6)	C21—H21B	0.9600
C6—H6	0.9300	C21—H21C	0.9600
C7—C8	1.371 (6)	O1—H1	0.86 (2)
C7—H7	0.9300
N1—C2—C1	109.6 (7)	C17—C12—C13	117.8 (4)
N1—C2—H2A	109.8	C17—C12—N2	117.2 (4)
C1—C2—H2A	109.8	C13—C12—N2	125.0 (4)
N1—C2—H2B	109.8	C12—C13—C14	120.8 (4)
C1—C2—H2B	109.8	C12—C13—H13	119.6
H2A—C2—H2B	108.2	C14—C13—H13	119.6
C4—C3—N1	107.9 (7)	C15—C14—C13	121.5 (4)
C4—C3—H3A	110.1	C15—C14—H14	119.2
N1—C3—H3A	110.1	C13—C14—H14	119.2
C4—C3—H3B	110.1	N3—C15—C14	122.1 (4)
N1—C3—H3B	110.1	N3—C15—C16	122.5 (4)
H3A—C3—H3B	108.4	C14—C15—C16	115.4 (4)
C2A—C1A—H1A1	109.5	C17—C16—C15	122.4 (4)
C2A—C1A—H1A2	109.5	C17—C16—H16	118.8
H1A1—C1A—H1A2	109.5	C15—C16—H16	118.8
C2A—C1A—H1A3	109.5	C12—C17—C16	122.0 (4)
H1A1—C1A—H1A3	109.5	C12—C17—H17	119.0
H1A2—C1A—H1A3	109.5	C16—C17—H17	119.0
N1—C2A—C1A	93 (2)	N3—C18—C19	113.4 (4)
N1—C2A—H2A1	113.2	N3—C18—H18A	108.9
C1A—C2A—H2A1	113.2	C19—C18—H18A	108.9
N1—C2A—H2A2	113.2	N3—C18—H18B	108.9
C1A—C2A—H2A2	113.2	C19—C18—H18B	108.9
H2A1—C2A—H2A2	110.5	H18A—C18—H18B	107.7
N1—C3A—C4A	99.1 (15)	C18—C19—H19A	109.5
N1—C3A—H3A1	111.9	C18—C19—H19B	109.5
C4A—C3A—H3A1	111.9	H19A—C19—H19B	109.5
N1—C3A—H3A2	111.9	C18—C19—H19C	109.5
C4A—C3A—H3A2	111.9	H19A—C19—H19C	109.5
H3A1—C3A—H3A2	109.6	H19B—C19—H19C	109.5
C3A—C4A—H4A1	109.5	N3—C20—C21	112.6 (4)
C3A—C4A—H4A2	109.5	N3—C20—H20A	109.1
H4A1—C4A—H4A2	109.5	C21—C20—H20A	109.1
C3A—C4A—H4A3	109.5	N3—C20—H20B	109.1
H4A1—C4A—H4A3	109.5	C21—C20—H20B	109.1
H4A2—C4A—H4A3	109.5	H20A—C20—H20B	107.8
N1—C5—C10	121.4 (4)	C20—C21—H21A	109.5
N1—C5—C6	120.9 (4)	C20—C21—H21B	109.5
C10—C5—C6	117.7 (4)	H21A—C21—H21B	109.5
C7—C6—C5	120.4 (4)	C20—C21—H21C	109.5
C7—C6—H6	119.8	H21A—C21—H21C	109.5
C5—C6—H6	119.8	H21B—C21—H21C	109.5
C6—C7—C8	122.6 (4)	C5—N1—C2A	117.2 (10)
C6—C7—H7	118.7	C5—N1—C3A	120.9 (7)
C8—C7—H7	118.7	C2A—N1—C3A	121.9 (12)
C7—C8—C9	117.2 (4)	C5—N1—C2	120.7 (5)
C7—C8—C11	120.7 (4)	C2A—N1—C2	40.3 (12)
C9—C8—C11	122.1 (4)	C3A—N1—C2	104.8 (9)
O1—C9—C10	118.3 (4)	C5—N1—C3	120.0 (5)
O1—C9—C8	119.7 (4)	C2A—N1—C3	103.2 (12)
C10—C9—C8	122.0 (4)	C3A—N1—C3	45.1 (8)
C9—C10—C5	120.1 (4)	C2—N1—C3	118.8 (6)
C9—C10—H10	120.0	C11—N2—C12	122.8 (4)
C5—C10—H10	120.0	C15—N3—C18	122.3 (4)
N2—C11—C8	121.3 (4)	C15—N3—C20	121.8 (4)
N2—C11—H11	119.4	C18—N3—C20	115.9 (4)
C8—C11—H11	119.4	C9—O1—H1	112 (4)
N1—C5—C6—C7	176.6 (5)	C6—C5—N1—C2	169.0 (6)
C10—C5—C6—C7	−2.5 (8)	C10—C5—N1—C3	160.6 (5)
C5—C6—C7—C8	0.6 (8)	C6—C5—N1—C3	−18.5 (8)
C6—C7—C8—C9	1.8 (7)	C1A—C2A—N1—C5	−106 (2)
C6—C7—C8—C11	−177.7 (4)	C1A—C2A—N1—C3A	75 (3)
C7—C8—C9—O1	177.9 (4)	C1A—C2A—N1—C2	0 (2)
C11—C8—C9—O1	−2.7 (6)	C1A—C2A—N1—C3	120 (2)
C7—C8—C9—C10	−2.2 (6)	C4A—C3A—N1—C5	−110.9 (14)
C11—C8—C9—C10	177.2 (4)	C4A—C3A—N1—C2A	68 (2)
O1—C9—C10—C5	−179.8 (4)	C4A—C3A—N1—C2	108.3 (15)
C8—C9—C10—C5	0.3 (7)	C4A—C3A—N1—C3	−7.8 (14)
N1—C5—C10—C9	−177.1 (5)	C1—C2—N1—C5	91.1 (9)
C6—C5—C10—C9	2.1 (7)	C1—C2—N1—C2A	−5.8 (16)
C7—C8—C11—N2	178.7 (4)	C1—C2—N1—C3A	−128.1 (9)
C9—C8—C11—N2	−0.8 (6)	C1—C2—N1—C3	−81.6 (8)
C17—C12—C13—C14	0.2 (6)	C4—C3—N1—C5	99.5 (7)
N2—C12—C13—C14	−177.9 (4)	C4—C3—N1—C2A	−127.9 (12)
C12—C13—C14—C15	0.0 (7)	C4—C3—N1—C3A	−5.7 (10)
C13—C14—C15—N3	179.3 (4)	C4—C3—N1—C2	−87.8 (7)
C13—C14—C15—C16	−1.0 (6)	C8—C11—N2—C12	−178.8 (4)
N3—C15—C16—C17	−178.5 (4)	C17—C12—N2—C11	173.3 (4)
C14—C15—C16—C17	1.8 (6)	C13—C12—N2—C11	−8.6 (6)
C13—C12—C17—C16	0.7 (6)	C14—C15—N3—C18	3.3 (7)
N2—C12—C17—C16	178.9 (4)	C16—C15—N3—C18	−176.3 (4)
C15—C16—C17—C12	−1.7 (7)	C14—C15—N3—C20	−178.2 (4)
C10—C5—N1—C2A	34.3 (15)	C16—C15—N3—C20	2.1 (6)
C6—C5—N1—C2A	−144.8 (15)	C19—C18—N3—C15	−86.1 (5)
C10—C5—N1—C3A	−146.5 (10)	C19—C18—N3—C20	95.3 (5)
C6—C5—N1—C3A	34.4 (12)	C21—C20—N3—C15	−86.4 (6)
C10—C5—N1—C2	−11.9 (9)	C21—C20—N3—C18	92.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.86 (2)	1.81 (4)	2.563 (5)	144 (6)
C18—H18A···Cg2i	0.97	2.92	3.660 (5)	134
C1A—H1A1···Cg1ii	0.96	2.80	3.49 (4)	130

Table 1

Hydrogen-bond geometry (, )

Cg1 and Cg2 are the centroids of the C5C10 and C12C17 rings, respectively.

DHA	DH	HA	D A	DHA
O1H1N2	0.86(2)	1.81(4)	2.563(5)	144(6)
C18H18A Cg2i	0.97	2.92	3.660(5)	134
C1AH1A1Cg1ii	0.96	2.80	3.49(4)	130

Symmetry codes: (i) ; (ii) .