3-(tert-Butyl­imino­meth­yl)-1,1′-bi­naph­thol ethanol solvate

The 1,1′-bi-2,2′-naphthol (BINOL) backbone of the title compound, C₂₅H₂₃NO₂·C₂H₆O, indicates that it has potential in asymmetric catalysis, with the two hydr­oxy and the imino groups providing sites for coordination with metal ions as an O/N heterotridentate ligand. There is an intra­molecular O—H...N hydrogen bond which forms a ring, and inter­molecular O—H...O hydrogen bonds to the ethanol solvent mol­ecule, which link two ethanol mol­ecules and two naphthol mol­ecules around a centre of symmetry.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.060
• wR factor = 0.128
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         37 Perc.
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N      -   C11     ..       7.46 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C12    -   C13     ..       8.44 su

Alert level C
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)        200 Ang.
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.55 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     -   C1      ..       5.66 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C2      ..       5.67 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C26

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

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

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S1. Comment

BINOL and its derivatives have been extensively used in chiral recognition and asymmetric catalysis (Pu, 1998). Herein we present the structure of the title compound, as a continuation of our previous studies.

As shown in Fig. 1, an intramolecular O—H···N hydrogen bond between the hydroxy and the imino groups forms a ring.

The molecules are connected by O—H···O hydrogen bonds to the ethanol, Fig. 2.

Related literature

For background on the application of salen complexes to asymmetric catalysis, see: Pu (1998). For details of the synthesis, see: Chin et al. (2004).

S2. Experimental

The salen ligand, 3-((p-tolylimino)methyl)-di-1,1'-binaphthol was prepared by condensation of 3-carboxaldehyde-1,1'-binaphthol with tert-butylamine, which was prepared by reported methods (Chin et al., 2004). Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol–methylene chloride (1:5) solution of the compound.

S3. Refinement

All the H atoms were placed in calculated positions and refined using the riding-model approximation.

Computing details

Data collection: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC (Gabe & White, 1993); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2005); software used to prepare material for publication: SHELXTL (Bruker, 2005).

Figures

	Fig. 1. A perspective view of the title compound. Ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view down the b axis showing intermolecular hydrogen bonding in the crystal structure.

3-(tert-Butyliminomethyl)-1,1'-binaphthol ethanol solvate

Crystal data

C25H23NO2·C2H6O	Z = 2
Mr = 415.51	F(000) = 444
Triclinic, P1	Dx = 1.205 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.538 (2) Å	Cell parameters from 17 reflections
b = 10.883 (2) Å	θ = 4.6–7.4°
c = 11.628 (2) Å	µ = 0.08 mm^−1
α = 74.27 (3)°	T = 294 K
β = 63.15 (3)°	Block, red
γ = 81.66 (3)°	0.38 × 0.32 × 0.23 mm
V = 1144.8 (5) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.007
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 1.9°
Graphite monochromator	h = −12→12
ω/2θ scans	k = −5→13
4249 measured reflections	l = −13→14
4243 independent reflections	3 standard reflections every 300 reflections
1591 reflections with I > 2σ(I)	intensity decay: 0.9%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.060	H-atom parameters constrained
wR(F^2) = 0.128	w = 1/[σ^2(Fo^2) + (0.04P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
4243 reflections	Δρmax = 0.18 e Å^−3
285 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0106 (18)

Special details

Experimental. The data are rather weak, as indicated by the poor fraction of observed reflections. This could be caused by a combination of factors, including an old X-ray tube and a crystal consisting of C, H, O, N atoms only. Nevertheless, the structure is complete and the refinement was stable.

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 > 2σ(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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.23813 (14)	0.25295 (15)	0.00754 (14)	0.0714 (5)
H1	0.2308	0.2413	−0.0560	0.107*
O2	0.29138 (15)	0.51814 (14)	0.13021 (16)	0.0765 (5)
H2	0.3533	0.5671	0.1126	0.115*
N	0.11745 (18)	0.22122 (17)	−0.12695 (17)	0.0622 (6)
C1	0.1127 (2)	0.3002 (2)	0.0889 (2)	0.0531 (7)
C2	0.1015 (2)	0.32673 (19)	0.2017 (2)	0.0465 (6)
C3	−0.0321 (2)	0.36873 (19)	0.2912 (2)	0.0476 (6)
C4	−0.0533 (2)	0.38853 (19)	0.4145 (2)	0.0553 (7)
H4A	0.0235	0.3789	0.4355	0.066*
C5	−0.1833 (2)	0.4212 (2)	0.5020 (2)	0.0662 (7)
H5A	−0.1951	0.4316	0.5831	0.079*
C6	−0.3004 (2)	0.4397 (2)	0.4716 (2)	0.0749 (8)
H6A	−0.3892	0.4622	0.5323	0.090*
C7	−0.2834 (2)	0.4246 (2)	0.3531 (2)	0.0711 (8)
H7A	−0.3610	0.4389	0.3328	0.085*
C8	−0.1503 (2)	0.38757 (19)	0.2599 (2)	0.0517 (6)
C9	−0.1306 (2)	0.3642 (2)	0.1395 (2)	0.0584 (7)
H9A	−0.2062	0.3807	0.1164	0.070*
C10	−0.0050 (2)	0.3184 (2)	0.0554 (2)	0.0517 (6)
C11	0.0085 (2)	0.2836 (2)	−0.0631 (2)	0.0584 (7)
H11A	−0.0631	0.3073	−0.0914	0.070*
C12	0.1377 (3)	0.1757 (2)	−0.2426 (2)	0.0725 (8)
C13	0.2872 (3)	0.2117 (3)	−0.3442 (3)	0.1122 (12)
H13A	0.3527	0.1765	−0.3063	0.168*
H13B	0.2935	0.3030	−0.3707	0.168*
H13C	0.3106	0.1784	−0.4201	0.168*
C14	0.1281 (3)	0.0320 (2)	−0.1994 (3)	0.1163 (11)
H14A	0.0319	0.0092	−0.1381	0.175*
H14B	0.1900	−0.0020	−0.1573	0.175*
H14C	0.1563	−0.0025	−0.2755	0.175*
C15	0.0337 (3)	0.2332 (3)	−0.3008 (3)	0.1185 (11)
H15A	−0.0605	0.2055	−0.2381	0.178*
H15B	0.0600	0.2059	−0.3807	0.178*
H15C	0.0357	0.3247	−0.3205	0.178*
C16	0.2282 (2)	0.3038 (2)	0.2312 (2)	0.0469 (6)
C17	0.3201 (2)	0.3998 (2)	0.1930 (2)	0.0540 (6)
C18	0.4422 (2)	0.3778 (2)	0.2172 (2)	0.0638 (7)
H18A	0.5024	0.4444	0.1923	0.077*
C19	0.4707 (2)	0.2594 (2)	0.2766 (2)	0.0671 (7)
H19A	0.5528	0.2450	0.2900	0.080*
C20	0.3808 (2)	0.1575 (2)	0.3187 (2)	0.0552 (7)
C21	0.4097 (3)	0.0347 (2)	0.3816 (2)	0.0747 (8)
H21A	0.4917	0.0199	0.3950	0.090*
C22	0.3207 (3)	−0.0630 (3)	0.4234 (3)	0.0834 (9)
H22A	0.3411	−0.1437	0.4656	0.100*
C23	0.1980 (3)	−0.0410 (2)	0.4022 (2)	0.0796 (9)
H23A	0.1365	−0.1075	0.4311	0.096*
C24	0.1670 (2)	0.0769 (2)	0.3398 (2)	0.0613 (7)
H24A	0.0853	0.0893	0.3261	0.074*
C25	0.2570 (2)	0.1797 (2)	0.2961 (2)	0.0513 (6)
O3	0.47214 (17)	0.68639 (16)	0.10162 (18)	0.0984 (7)
H3	0.5567	0.6966	0.0511	0.148*
C26	0.4083 (3)	0.8033 (3)	0.1328 (3)	0.1012 (11)
H26A	0.4742	0.8488	0.1426	0.121*
H26B	0.3242	0.7867	0.2168	0.121*
C27	0.3677 (4)	0.8845 (3)	0.0288 (3)	0.1396 (15)
H27A	0.3169	0.9596	0.0569	0.209*
H27B	0.3081	0.8374	0.0143	0.209*
H27C	0.4519	0.9089	−0.0521	0.209*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0537 (8)	0.1142 (12)	0.0639 (9)	0.0069 (9)	−0.0302 (7)	−0.0440 (9)
O2	0.0724 (9)	0.0695 (11)	0.1014 (11)	−0.0121 (9)	−0.0543 (9)	−0.0057 (9)
N	0.0721 (11)	0.0697 (13)	0.0620 (11)	0.0085 (10)	−0.0401 (10)	−0.0271 (10)
C1	0.0419 (12)	0.0615 (15)	0.0629 (14)	0.0039 (11)	−0.0250 (11)	−0.0238 (12)
C2	0.0440 (11)	0.0521 (13)	0.0491 (13)	−0.0024 (11)	−0.0232 (10)	−0.0146 (11)
C3	0.0488 (12)	0.0479 (13)	0.0532 (13)	−0.0003 (11)	−0.0262 (10)	−0.0159 (11)
C4	0.0499 (12)	0.0612 (15)	0.0614 (14)	−0.0012 (12)	−0.0266 (11)	−0.0201 (12)
C5	0.0610 (14)	0.0778 (16)	0.0662 (15)	0.0030 (13)	−0.0247 (12)	−0.0344 (13)
C6	0.0507 (14)	0.0947 (18)	0.0915 (17)	0.0131 (13)	−0.0292 (13)	−0.0511 (15)
C7	0.0539 (13)	0.0862 (17)	0.0958 (17)	0.0199 (13)	−0.0435 (13)	−0.0474 (14)
C8	0.0480 (12)	0.0494 (14)	0.0668 (14)	0.0016 (11)	−0.0285 (11)	−0.0226 (11)
C9	0.0525 (12)	0.0641 (15)	0.0822 (15)	0.0089 (12)	−0.0454 (11)	−0.0295 (12)
C10	0.0479 (12)	0.0601 (15)	0.0580 (14)	0.0013 (11)	−0.0314 (11)	−0.0165 (11)
C11	0.0685 (13)	0.0624 (15)	0.0639 (14)	−0.0033 (12)	−0.0455 (12)	−0.0136 (12)
C12	0.0925 (17)	0.0819 (18)	0.0570 (14)	0.0030 (15)	−0.0403 (13)	−0.0261 (13)
C13	0.129 (2)	0.122 (2)	0.075 (2)	0.000 (2)	−0.0265 (19)	−0.0417 (18)
C14	0.192 (3)	0.077 (2)	0.103 (2)	−0.002 (2)	−0.082 (2)	−0.0257 (17)
C15	0.156 (2)	0.149 (3)	0.1035 (19)	0.034 (2)	−0.1005 (17)	−0.0517 (18)
C16	0.0381 (11)	0.0618 (14)	0.0489 (13)	0.0007 (11)	−0.0224 (10)	−0.0202 (11)
C17	0.0510 (12)	0.0637 (15)	0.0585 (14)	−0.0015 (12)	−0.0319 (11)	−0.0167 (12)
C18	0.0552 (13)	0.0801 (18)	0.0756 (15)	−0.0063 (13)	−0.0418 (12)	−0.0218 (13)
C19	0.0515 (13)	0.0961 (19)	0.0725 (15)	0.0053 (14)	−0.0393 (12)	−0.0301 (14)
C20	0.0502 (12)	0.0728 (16)	0.0509 (13)	0.0081 (12)	−0.0264 (11)	−0.0243 (12)
C21	0.0834 (16)	0.0813 (18)	0.0788 (16)	0.0238 (15)	−0.0507 (13)	−0.0339 (14)
C22	0.1048 (19)	0.0683 (18)	0.0862 (18)	0.0195 (16)	−0.0547 (16)	−0.0196 (15)
C23	0.0879 (18)	0.0596 (17)	0.0850 (19)	−0.0023 (15)	−0.0317 (16)	−0.0170 (15)
C24	0.0583 (13)	0.0584 (16)	0.0728 (16)	0.0023 (13)	−0.0336 (12)	−0.0164 (13)
C25	0.0471 (12)	0.0638 (15)	0.0496 (13)	0.0021 (12)	−0.0208 (11)	−0.0254 (12)
O3	0.0676 (11)	0.0905 (12)	0.1351 (15)	−0.0118 (10)	−0.0260 (11)	−0.0503 (11)
C26	0.0854 (19)	0.107 (2)	0.113 (2)	−0.0059 (18)	−0.0273 (18)	−0.0545 (19)
C27	0.171 (3)	0.126 (3)	0.111 (3)	0.006 (3)	−0.057 (2)	−0.022 (2)

Geometric parameters (Å, º)

O1—C1	1.358 (2)	C14—H14A	0.9600
O1—H1	0.8200	C14—H14B	0.9600
O2—C17	1.364 (3)	C14—H14C	0.9600
O2—H2	0.8200	C15—H15A	0.9600
N—C11	1.268 (3)	C15—H15B	0.9600
N—C12	1.473 (3)	C15—H15C	0.9600
C1—C2	1.368 (3)	C16—C17	1.371 (3)
C1—C10	1.433 (3)	C16—C25	1.421 (3)
C2—C3	1.422 (3)	C17—C18	1.411 (3)
C2—C16	1.494 (3)	C18—C19	1.350 (3)
C3—C4	1.419 (3)	C18—H18A	0.9300
C3—C8	1.422 (3)	C19—C20	1.400 (3)
C4—C5	1.354 (3)	C19—H19A	0.9300
C4—H4A	0.9300	C20—C21	1.402 (3)
C5—C6	1.404 (3)	C20—C25	1.419 (3)
C5—H5A	0.9300	C21—C22	1.358 (3)
C6—C7	1.361 (3)	C21—H21A	0.9300
C6—H6A	0.9300	C22—C23	1.398 (3)
C7—C8	1.416 (3)	C22—H22A	0.9300
C7—H7A	0.9300	C23—C24	1.366 (3)
C8—C9	1.408 (3)	C23—H23A	0.9300
C9—C10	1.364 (3)	C24—C25	1.404 (3)
C9—H9A	0.9300	C24—H24A	0.9300
C10—C11	1.468 (3)	O3—C26	1.409 (3)
C11—H11A	0.9300	O3—H3	0.8200
C12—C13	1.510 (3)	C26—C27	1.485 (4)
C12—C14	1.511 (3)	C26—H26A	0.9700
C12—C15	1.514 (3)	C26—H26B	0.9700
C13—H13A	0.9600	C27—H27A	0.9600
C13—H13B	0.9600	C27—H27B	0.9600
C13—H13C	0.9600	C27—H27C	0.9600
C1—O1—H1	109.5	H14A—C14—H14C	109.5
C17—O2—H2	109.5	H14B—C14—H14C	109.5
C11—N—C12	124.3 (2)	C12—C15—H15A	109.5
O1—C1—C2	119.2 (2)	C12—C15—H15B	109.5
O1—C1—C10	118.9 (2)	H15A—C15—H15B	109.5
C2—C1—C10	121.89 (19)	C12—C15—H15C	109.5
C1—C2—C3	119.3 (2)	H15A—C15—H15C	109.5
C1—C2—C16	118.98 (18)	H15B—C15—H15C	109.5
C3—C2—C16	121.6 (2)	C17—C16—C25	119.2 (2)
C4—C3—C8	118.28 (19)	C17—C16—C2	121.1 (2)
C4—C3—C2	122.0 (2)	C25—C16—C2	119.73 (19)
C8—C3—C2	119.7 (2)	O2—C17—C16	118.4 (2)
C5—C4—C3	121.1 (2)	O2—C17—C18	120.2 (2)
C5—C4—H4A	119.4	C16—C17—C18	121.3 (2)
C3—C4—H4A	119.4	C19—C18—C17	119.4 (2)
C4—C5—C6	120.8 (2)	C19—C18—H18A	120.3
C4—C5—H5A	119.6	C17—C18—H18A	120.3
C6—C5—H5A	119.6	C18—C19—C20	122.1 (2)
C7—C6—C5	119.8 (2)	C18—C19—H19A	119.0
C7—C6—H6A	120.1	C20—C19—H19A	119.0
C5—C6—H6A	120.1	C19—C20—C21	122.1 (2)
C6—C7—C8	121.4 (2)	C19—C20—C25	118.6 (2)
C6—C7—H7A	119.3	C21—C20—C25	119.3 (2)
C8—C7—H7A	119.3	C22—C21—C20	121.5 (3)
C9—C8—C7	122.9 (2)	C22—C21—H21A	119.2
C9—C8—C3	118.41 (19)	C20—C21—H21A	119.2
C7—C8—C3	118.6 (2)	C21—C22—C23	119.3 (3)
C10—C9—C8	122.6 (2)	C21—C22—H22A	120.4
C10—C9—H9A	118.7	C23—C22—H22A	120.4
C8—C9—H9A	118.7	C24—C23—C22	121.0 (3)
C9—C10—C1	118.0 (2)	C24—C23—H23A	119.5
C9—C10—C11	121.3 (2)	C22—C23—H23A	119.5
C1—C10—C11	120.62 (19)	C23—C24—C25	120.9 (2)
N—C11—C10	120.1 (2)	C23—C24—H24A	119.5
N—C11—H11A	120.0	C25—C24—H24A	119.5
C10—C11—H11A	120.0	C24—C25—C20	118.0 (2)
N—C12—C13	105.0 (2)	C24—C25—C16	122.6 (2)
N—C12—C14	107.0 (2)	C20—C25—C16	119.4 (2)
C13—C12—C14	109.5 (2)	C26—O3—H3	109.5
N—C12—C15	114.6 (2)	O3—C26—C27	111.7 (3)
C13—C12—C15	109.7 (2)	O3—C26—H26A	109.3
C14—C12—C15	110.8 (2)	C27—C26—H26A	109.3
C12—C13—H13A	109.5	O3—C26—H26B	109.3
C12—C13—H13B	109.5	C27—C26—H26B	109.3
H13A—C13—H13B	109.5	H26A—C26—H26B	107.9
C12—C13—H13C	109.5	C26—C27—H27A	109.5
H13A—C13—H13C	109.5	C26—C27—H27B	109.5
H13B—C13—H13C	109.5	H27A—C27—H27B	109.5
C12—C14—H14A	109.5	C26—C27—H27C	109.5
C12—C14—H14B	109.5	H27A—C27—H27C	109.5
H14A—C14—H14B	109.5	H27B—C27—H27C	109.5
C12—C14—H14C	109.5
O1—C1—C2—C3	−176.13 (18)	C11—N—C12—C14	−110.2 (3)
C10—C1—C2—C3	2.5 (3)	C11—N—C12—C15	13.0 (3)
O1—C1—C2—C16	0.5 (3)	C1—C2—C16—C17	93.7 (3)
C10—C1—C2—C16	179.18 (19)	C3—C2—C16—C17	−89.7 (3)
C1—C2—C3—C4	175.2 (2)	C1—C2—C16—C25	−84.2 (3)
C16—C2—C3—C4	−1.4 (3)	C3—C2—C16—C25	92.3 (3)
C1—C2—C3—C8	−2.6 (3)	C25—C16—C17—O2	179.68 (19)
C16—C2—C3—C8	−179.11 (19)	C2—C16—C17—O2	1.7 (3)
C8—C3—C4—C5	1.7 (3)	C25—C16—C17—C18	−0.2 (3)
C2—C3—C4—C5	−176.0 (2)	C2—C16—C17—C18	−178.1 (2)
C3—C4—C5—C6	−1.6 (3)	O2—C17—C18—C19	−178.4 (2)
C4—C5—C6—C7	0.0 (4)	C16—C17—C18—C19	1.4 (3)
C5—C6—C7—C8	1.4 (4)	C17—C18—C19—C20	−1.8 (4)
C6—C7—C8—C9	176.4 (2)	C18—C19—C20—C21	−179.4 (2)
C6—C7—C8—C3	−1.3 (3)	C18—C19—C20—C25	1.0 (3)
C4—C3—C8—C9	−178.08 (19)	C19—C20—C21—C22	179.2 (2)
C2—C3—C8—C9	−0.3 (3)	C25—C20—C21—C22	−1.1 (4)
C4—C3—C8—C7	−0.2 (3)	C20—C21—C22—C23	0.5 (4)
C2—C3—C8—C7	177.57 (19)	C21—C22—C23—C24	0.3 (4)
C7—C8—C9—C10	−174.4 (2)	C22—C23—C24—C25	−0.6 (4)
C3—C8—C9—C10	3.3 (3)	C23—C24—C25—C20	0.0 (3)
C8—C9—C10—C1	−3.4 (3)	C23—C24—C25—C16	−179.8 (2)
C8—C9—C10—C11	174.17 (19)	C19—C20—C25—C24	−179.5 (2)
O1—C1—C10—C9	179.05 (19)	C21—C20—C25—C24	0.8 (3)
C2—C1—C10—C9	0.4 (3)	C19—C20—C25—C16	0.3 (3)
O1—C1—C10—C11	1.5 (3)	C21—C20—C25—C16	−179.4 (2)
C2—C1—C10—C11	−177.19 (19)	C17—C16—C25—C24	179.1 (2)
C12—N—C11—C10	176.56 (19)	C2—C16—C25—C24	−2.9 (3)
C9—C10—C11—N	−167.9 (2)	C17—C16—C25—C20	−0.7 (3)
C1—C10—C11—N	9.6 (3)	C2—C16—C25—C20	177.34 (19)
C11—N—C12—C13	133.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N	0.82	1.79	2.530 (3)	148
O2—H2···O3	0.82	1.87	2.684 (2)	170
O3—H3···O1^i	0.82	2.06	2.828 (2)	156

Symmetry code: (i) −x+1, −y+1, −z.