A new polymorph of 1-({[1,3-dihy-droxy-2-(hy-droxy-meth-yl)propan-2-yl]iminio}meth-yl)naphthalen-2-olate.

The title compound, C15H17NO4, containing two mol-ecules in the asymmetric unit is a polymorph of the crystal structure published by Martínez et al. [(2011). Eur. J. Org. Chem. pp. 3137-3145] which at 120 K is monoclinic with one mol-ecule in the asymmetric unit. Both mol-ecules in the title compound are in the trans form. In the crystal, N-H⋯O and O-H⋯O hydrogen bonds connect mol-ecules, forming a two-dimensional network parallel to (001).

Related literature

For applications of Schiff bases, see: Weber et al. (2007 ▸); Chen et al. (2008 ▸); May et al.(2004 ▸). For background to the potential use of the title compound, see: Dong et al. (2014 ▸); Liu et al. (2014 ▸). For the structures of related Schiff bases derived from 2-hy­droxy­napthaldehyde, see: Wang et al. (2011 ▸); Kennedy et al. (2013 ▸); Abu-Dief et al. (2015 ▸). For the first polymorph, see: Martínez et al. (2011 ▸).

Experimental

Crystal data

C15H17NO4

M = 275.30

Monoclinic,

a = 9.3540 (8) Å

b = 10.0280 (9) Å

c = 29.036 (3) Å

β = 91.559 (1)°

V = 2722.6 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.49 × 0.45 × 0.44 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▸) T min = 0.954, T max = 0.958

13224 measured reflections

4775 independent reflections

2778 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.137

S = 1.05

4775 reflections

368 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2002 ▸); cell refinement: SAINT (Bruker, 2002 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: SHELXTL (Sheldrick, 2008 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S205698901501539X/lh5776sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901501539X/lh5776Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S205698901501539X/lh5776fig1.tif

The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.

Click here for additional data file.

. DOI: 10.1107/S205698901501539X/lh5776fig2.tif

Part of the crystal structure with the hydrogen bonds drawn as dashed lines.

CCDC reference: 1419383

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

C15H17NO4	F(000) = 1168
Mr = 275.30	Dx = 1.343 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3152 reflections
a = 9.3540 (8) Å	θ = 2.5–25.6°
b = 10.0280 (9) Å	µ = 0.10 mm−1
c = 29.036 (3) Å	T = 293 K
β = 91.559 (1)°	Block, colorless
V = 2722.6 (4) Å3	0.49 × 0.45 × 0.44 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	4775 independent reflections
Radiation source: fine-focus sealed tube	2778 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −11→11
Tmin = 0.954, Tmax = 0.958	k = −10→11
13224 measured reflections	l = −34→24

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)] = 0.052	H-atom parameters constrained
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.0453P)2 + 1.3323P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
4775 reflections	Δρmax = 0.37 e Å−3
368 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0078 (7)

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	0.4266 (2)	0.5340 (2)	0.65750 (7)	0.0368 (5)
H1	0.3778	0.4957	0.6784	0.044*
N2	0.9319 (2)	0.9508 (2)	0.67169 (7)	0.0368 (5)
H2	0.8792	0.9830	0.6928	0.044*
O1	0.80392 (19)	0.5859 (2)	0.68816 (8)	0.0621 (6)
H1C	0.8582	0.5347	0.7020	0.093*
O2	0.49270 (19)	0.54635 (19)	0.74996 (6)	0.0468 (5)
H2C	0.4247	0.5638	0.7662	0.070*
O3	0.4541 (2)	0.8049 (2)	0.63099 (6)	0.0501 (5)
H3	0.4281	0.8446	0.6540	0.075*
O4	0.20984 (19)	0.3874 (2)	0.67796 (6)	0.0510 (5)
O5	0.9988 (2)	0.93735 (19)	0.76456 (6)	0.0470 (5)
H5	0.9340	0.9140	0.7812	0.071*
O6	1.31332 (18)	0.91941 (18)	0.70090 (7)	0.0493 (5)
H6	1.3611	0.9706	0.7171	0.074*
O7	1.1405 (2)	0.7931 (2)	0.61213 (6)	0.0560 (6)
H7	1.2275	0.7836	0.6111	0.084*
O8	0.71162 (19)	1.0887 (2)	0.69349 (7)	0.0553 (6)
C1	0.6809 (3)	0.5160 (3)	0.67280 (9)	0.0414 (7)
H1A	0.6645	0.4406	0.6929	0.050*
H1B	0.6943	0.4826	0.6419	0.050*
C2	0.5234 (3)	0.6581 (3)	0.72181 (8)	0.0409 (7)
H2A	0.6065	0.7050	0.7343	0.049*
H2B	0.4430	0.7193	0.7212	0.049*
C3	0.5793 (3)	0.7303 (3)	0.64202 (9)	0.0401 (7)
H3A	0.6485	0.7884	0.6573	0.048*
H3B	0.6206	0.6993	0.6137	0.048*
C4	0.5521 (2)	0.6100 (3)	0.67308 (8)	0.0327 (6)
C5	0.3813 (3)	0.5185 (3)	0.61482 (9)	0.0352 (6)
H5A	0.4329	0.5604	0.5920	0.042*
C6	0.2609 (2)	0.4436 (2)	0.60076 (9)	0.0341 (6)
C7	0.1775 (3)	0.3805 (3)	0.63474 (10)	0.0403 (7)
C8	0.0531 (3)	0.3070 (3)	0.61916 (11)	0.0558 (8)
H8A	−0.0056	0.2676	0.6406	0.067*
C9	0.0206 (3)	0.2948 (3)	0.57391 (12)	0.0593 (9)
H9	−0.0601	0.2458	0.5652	0.071*
C10	0.1033 (3)	0.3528 (3)	0.53867 (10)	0.0465 (7)
C11	0.2235 (3)	0.4311 (3)	0.55185 (9)	0.0386 (6)
C12	0.2988 (3)	0.4917 (3)	0.51637 (9)	0.0521 (8)
H12	0.3777	0.5446	0.5239	0.063*
C13	0.2595 (3)	0.4752 (4)	0.47095 (11)	0.0626 (9)
H13	0.3120	0.5169	0.4483	0.075*
C14	0.1425 (4)	0.3972 (3)	0.45827 (12)	0.0653 (9)
H14	0.1170	0.3856	0.4274	0.078*
C15	0.0658 (3)	0.3381 (3)	0.49156 (12)	0.0584 (9)
H15	−0.0134	0.2867	0.4831	0.070*
C16	1.0373 (3)	0.8292 (3)	0.73559 (9)	0.0427 (7)
H16A	0.9611	0.7635	0.7346	0.051*
H16B	1.1231	0.7866	0.7480	0.051*
C17	1.1832 (2)	0.9830 (3)	0.68673 (9)	0.0389 (7)
H17A	1.1919	1.0195	0.6560	0.047*
H17B	1.1621	1.0556	0.7076	0.047*
C18	1.0944 (3)	0.7591 (3)	0.65660 (9)	0.0421 (7)
H18A	1.1673	0.7048	0.6718	0.051*
H18B	1.0083	0.7056	0.6535	0.051*
C19	1.0635 (2)	0.8799 (3)	0.68711 (8)	0.0340 (6)
C20	0.8883 (3)	0.9693 (3)	0.62907 (8)	0.0343 (6)
H20	0.9424	0.9323	0.6059	0.041*
C21	0.7644 (2)	1.0416 (2)	0.61581 (8)	0.0332 (6)
C22	0.6788 (3)	1.0992 (3)	0.65039 (10)	0.0399 (7)
C23	0.5528 (3)	1.1703 (3)	0.63563 (11)	0.0544 (8)
H23	0.4930	1.2061	0.6575	0.065*
C24	0.5195 (3)	1.1862 (3)	0.59069 (12)	0.0601 (9)
H24	0.4369	1.2330	0.5825	0.072*
C25	0.6046 (3)	1.1347 (3)	0.55519 (10)	0.0468 (7)
C26	0.7267 (3)	1.0578 (3)	0.56717 (9)	0.0379 (6)
C27	0.8045 (3)	1.0038 (3)	0.53105 (9)	0.0499 (8)
H27	0.8845	0.9517	0.5379	0.060*
C28	0.7657 (4)	1.0257 (4)	0.48594 (10)	0.0666 (10)
H28	0.8193	0.9881	0.4627	0.080*
C29	0.6471 (4)	1.1036 (4)	0.47439 (12)	0.0718 (11)
H29	0.6221	1.1195	0.4437	0.086*
C30	0.5683 (4)	1.1560 (3)	0.50842 (12)	0.0660 (10)
H30	0.4883	1.2072	0.5007	0.079*

	U11	U22	U33	U12	U13	U23
N1	0.0296 (11)	0.0475 (14)	0.0333 (13)	−0.0042 (10)	0.0018 (9)	0.0056 (10)
N2	0.0278 (11)	0.0511 (14)	0.0316 (12)	0.0033 (10)	0.0016 (9)	−0.0024 (10)
O1	0.0331 (11)	0.0564 (14)	0.0959 (18)	−0.0041 (10)	−0.0162 (11)	0.0145 (12)
O2	0.0380 (11)	0.0629 (13)	0.0397 (11)	0.0065 (9)	0.0037 (8)	0.0169 (10)
O3	0.0546 (12)	0.0534 (13)	0.0419 (11)	0.0079 (10)	−0.0087 (9)	0.0062 (10)
O4	0.0441 (11)	0.0665 (14)	0.0426 (12)	−0.0097 (10)	0.0063 (9)	0.0055 (10)
O5	0.0437 (11)	0.0620 (13)	0.0356 (11)	−0.0067 (10)	0.0048 (8)	−0.0086 (10)
O6	0.0334 (10)	0.0512 (13)	0.0626 (14)	0.0027 (9)	−0.0113 (9)	−0.0158 (10)
O7	0.0493 (12)	0.0768 (15)	0.0420 (12)	0.0052 (12)	0.0060 (9)	−0.0067 (11)
O8	0.0439 (12)	0.0816 (16)	0.0407 (12)	0.0112 (11)	0.0049 (9)	−0.0078 (11)
C1	0.0322 (15)	0.0486 (18)	0.0434 (16)	−0.0010 (13)	0.0009 (12)	0.0029 (13)
C2	0.0423 (15)	0.0474 (17)	0.0329 (15)	0.0007 (13)	−0.0015 (12)	0.0015 (13)
C3	0.0341 (14)	0.0450 (17)	0.0411 (16)	−0.0004 (13)	−0.0006 (12)	0.0030 (13)
C4	0.0270 (13)	0.0352 (15)	0.0357 (15)	−0.0040 (11)	−0.0013 (11)	0.0055 (12)
C5	0.0322 (14)	0.0388 (16)	0.0346 (15)	0.0034 (12)	0.0036 (11)	0.0015 (12)
C6	0.0280 (13)	0.0326 (15)	0.0415 (16)	0.0011 (11)	−0.0002 (11)	−0.0022 (12)
C7	0.0343 (15)	0.0380 (16)	0.0486 (18)	0.0026 (12)	0.0038 (13)	0.0031 (13)
C8	0.0478 (18)	0.055 (2)	0.064 (2)	−0.0175 (15)	0.0032 (16)	0.0070 (17)
C9	0.0485 (18)	0.051 (2)	0.078 (3)	−0.0189 (15)	−0.0109 (17)	−0.0016 (18)
C10	0.0438 (17)	0.0383 (17)	0.057 (2)	0.0016 (14)	−0.0068 (14)	−0.0080 (14)
C11	0.0339 (14)	0.0388 (16)	0.0429 (16)	0.0079 (13)	−0.0013 (12)	−0.0037 (13)
C12	0.0437 (17)	0.070 (2)	0.0425 (18)	−0.0051 (15)	−0.0020 (14)	−0.0053 (16)
C13	0.061 (2)	0.083 (3)	0.0440 (19)	0.0016 (19)	−0.0021 (16)	−0.0041 (18)
C14	0.073 (2)	0.074 (2)	0.047 (2)	0.013 (2)	−0.0115 (18)	−0.0167 (18)
C15	0.059 (2)	0.050 (2)	0.065 (2)	0.0017 (16)	−0.0177 (17)	−0.0164 (17)
C16	0.0406 (15)	0.0502 (18)	0.0372 (16)	−0.0016 (14)	0.0004 (12)	0.0007 (14)
C17	0.0316 (14)	0.0442 (17)	0.0409 (16)	0.0006 (12)	−0.0007 (12)	−0.0027 (13)
C18	0.0390 (15)	0.0477 (18)	0.0397 (17)	0.0002 (13)	0.0001 (12)	−0.0054 (13)
C19	0.0274 (13)	0.0444 (16)	0.0299 (14)	0.0012 (12)	−0.0031 (11)	−0.0012 (12)
C20	0.0313 (14)	0.0426 (16)	0.0291 (14)	−0.0034 (12)	0.0022 (11)	−0.0030 (12)
C21	0.0271 (13)	0.0342 (15)	0.0381 (15)	−0.0039 (11)	−0.0024 (11)	0.0023 (12)
C22	0.0313 (14)	0.0414 (17)	0.0470 (18)	−0.0006 (12)	0.0020 (12)	−0.0042 (13)
C23	0.0475 (18)	0.0482 (19)	0.067 (2)	0.0123 (15)	0.0002 (16)	−0.0088 (16)
C24	0.0533 (19)	0.0450 (19)	0.081 (3)	0.0147 (15)	−0.0151 (18)	0.0043 (17)
C25	0.0475 (17)	0.0376 (17)	0.0546 (19)	−0.0048 (14)	−0.0116 (14)	0.0112 (14)
C26	0.0382 (15)	0.0371 (16)	0.0380 (16)	−0.0084 (13)	−0.0059 (12)	0.0049 (13)
C27	0.0432 (17)	0.066 (2)	0.0402 (17)	−0.0057 (15)	−0.0022 (14)	0.0035 (15)
C28	0.068 (2)	0.094 (3)	0.0384 (18)	−0.017 (2)	−0.0031 (16)	0.0068 (18)
C29	0.080 (3)	0.089 (3)	0.046 (2)	−0.026 (2)	−0.0203 (19)	0.028 (2)
C30	0.065 (2)	0.061 (2)	0.070 (2)	−0.0049 (18)	−0.0240 (19)	0.0281 (19)

N1—C5	1.308 (3)	C10—C15	1.411 (4)
N1—C4	1.461 (3)	C10—C11	1.415 (4)
N1—H1	0.8600	C11—C12	1.402 (4)
N2—C20	1.306 (3)	C12—C13	1.369 (4)
N2—C19	1.480 (3)	C12—H12	0.9300
N2—H2	0.8600	C13—C14	1.387 (4)
O1—C1	1.409 (3)	C13—H13	0.9300
O1—H1C	0.8200	C14—C15	1.356 (4)
O2—C2	1.421 (3)	C14—H14	0.9300
O2—H2C	0.8200	C15—H15	0.9300
O3—C3	1.419 (3)	C16—C19	1.523 (3)
O3—H3	0.8200	C16—H16A	0.9700
O4—C7	1.285 (3)	C16—H16B	0.9700
O5—C16	1.425 (3)	C17—C19	1.525 (3)
O5—H5	0.8200	C17—H17A	0.9700
O6—C17	1.425 (3)	C17—H17B	0.9700
O6—H6	0.8200	C18—C19	1.532 (3)
O7—C18	1.414 (3)	C18—H18A	0.9700
O7—H7	0.8200	C18—H18B	0.9700
O8—C22	1.285 (3)	C20—C21	1.412 (3)
C1—C4	1.530 (3)	C20—H20	0.9300
C1—H1A	0.9700	C21—C22	1.423 (3)
C1—H1B	0.9700	C21—C26	1.455 (3)
C2—C4	1.526 (3)	C22—C23	1.433 (4)
C2—H2A	0.9700	C23—C24	1.343 (4)
C2—H2B	0.9700	C23—H23	0.9300
C3—C4	1.532 (3)	C24—C25	1.417 (4)
C3—H3A	0.9700	C24—H24	0.9300
C3—H3B	0.9700	C25—C30	1.407 (4)
C5—C6	1.405 (3)	C25—C26	1.414 (4)
C5—H5A	0.9300	C26—C27	1.401 (4)
C6—C7	1.423 (3)	C27—C28	1.367 (4)
C6—C11	1.459 (3)	C27—H27	0.9300
C7—C8	1.440 (4)	C28—C29	1.391 (5)
C8—C9	1.346 (4)	C28—H28	0.9300
C8—H8A	0.9300	C29—C30	1.355 (5)
C9—C10	1.424 (4)	C29—H29	0.9300
C9—H9	0.9300	C30—H30	0.9300
C5—N1—C4	126.3 (2)	C15—C14—C13	119.1 (3)
C5—N1—H1	116.9	C15—C14—H14	120.4
C4—N1—H1	116.9	C13—C14—H14	120.4
C20—N2—C19	126.2 (2)	C14—C15—C10	121.5 (3)
C20—N2—H2	116.9	C14—C15—H15	119.2
C19—N2—H2	116.9	C10—C15—H15	119.2
C1—O1—H1C	109.5	O5—C16—C19	110.0 (2)
C2—O2—H2C	109.5	O5—C16—H16A	109.7
C3—O3—H3	109.5	C19—C16—H16A	109.7
C16—O5—H5	109.5	O5—C16—H16B	109.7
C17—O6—H6	109.5	C19—C16—H16B	109.7
C18—O7—H7	109.5	H16A—C16—H16B	108.2
O1—C1—C4	109.2 (2)	O6—C17—C19	108.4 (2)
O1—C1—H1A	109.8	O6—C17—H17A	110.0
C4—C1—H1A	109.8	C19—C17—H17A	110.0
O1—C1—H1B	109.8	O6—C17—H17B	110.0
C4—C1—H1B	109.8	C19—C17—H17B	110.0
H1A—C1—H1B	108.3	H17A—C17—H17B	108.4
O2—C2—C4	109.1 (2)	O7—C18—C19	113.9 (2)
O2—C2—H2A	109.9	O7—C18—H18A	108.8
C4—C2—H2A	109.9	C19—C18—H18A	108.8
O2—C2—H2B	109.9	O7—C18—H18B	108.8
C4—C2—H2B	109.9	C19—C18—H18B	108.8
H2A—C2—H2B	108.3	H18A—C18—H18B	107.7
O3—C3—C4	113.5 (2)	N2—C19—C16	106.65 (19)
O3—C3—H3A	108.9	N2—C19—C17	106.0 (2)
C4—C3—H3A	108.9	C16—C19—C17	111.7 (2)
O3—C3—H3B	108.9	N2—C19—C18	111.9 (2)
C4—C3—H3B	108.9	C16—C19—C18	107.9 (2)
H3A—C3—H3B	107.7	C17—C19—C18	112.5 (2)
N1—C4—C2	106.98 (19)	N2—C20—C21	124.3 (2)
N1—C4—C1	107.7 (2)	N2—C20—H20	117.8
C2—C4—C1	111.0 (2)	C21—C20—H20	117.8
N1—C4—C3	111.9 (2)	C20—C21—C22	119.3 (2)
C2—C4—C3	109.5 (2)	C20—C21—C26	119.8 (2)
C1—C4—C3	109.8 (2)	C22—C21—C26	120.9 (2)
N1—C5—C6	125.1 (2)	O8—C22—C21	122.0 (2)
N1—C5—H5A	117.5	O8—C22—C23	120.3 (2)
C6—C5—H5A	117.5	C21—C22—C23	117.7 (3)
C5—C6—C7	119.1 (2)	C24—C23—C22	121.1 (3)
C5—C6—C11	119.9 (2)	C24—C23—H23	119.5
C7—C6—C11	121.0 (2)	C22—C23—H23	119.5
O4—C7—C6	122.3 (2)	C23—C24—C25	123.0 (3)
O4—C7—C8	120.1 (2)	C23—C24—H24	118.5
C6—C7—C8	117.6 (3)	C25—C24—H24	118.5
C9—C8—C7	120.8 (3)	C30—C25—C26	119.5 (3)
C9—C8—H8A	119.6	C30—C25—C24	121.4 (3)
C7—C8—H8A	119.6	C26—C25—C24	119.1 (3)
C8—C9—C10	123.5 (3)	C27—C26—C25	117.3 (3)
C8—C9—H9	118.2	C27—C26—C21	124.5 (2)
C10—C9—H9	118.2	C25—C26—C21	118.2 (2)
C15—C10—C11	119.7 (3)	C28—C27—C26	121.7 (3)
C15—C10—C9	121.9 (3)	C28—C27—H27	119.2
C11—C10—C9	118.4 (3)	C26—C27—H27	119.2
C12—C11—C10	116.9 (3)	C27—C28—C29	120.7 (3)
C12—C11—C6	124.4 (2)	C27—C28—H28	119.7
C10—C11—C6	118.6 (2)	C29—C28—H28	119.7
C13—C12—C11	121.9 (3)	C30—C29—C28	119.2 (3)
C13—C12—H12	119.1	C30—C29—H29	120.4
C11—C12—H12	119.1	C28—C29—H29	120.4
C12—C13—C14	120.8 (3)	C29—C30—C25	121.6 (3)
C12—C13—H13	119.6	C29—C30—H30	119.2
C14—C13—H13	119.6	C25—C30—H30	119.2
C5—N1—C4—C2	152.3 (2)	C20—N2—C19—C16	−154.9 (2)
C5—N1—C4—C1	−88.3 (3)	C20—N2—C19—C17	85.9 (3)
C5—N1—C4—C3	32.4 (3)	C20—N2—C19—C18	−37.1 (3)
O2—C2—C4—N1	56.2 (3)	O5—C16—C19—N2	−55.8 (3)
O2—C2—C4—C1	−60.9 (3)	O5—C16—C19—C17	59.7 (3)
O2—C2—C4—C3	177.73 (19)	O5—C16—C19—C18	−176.2 (2)
O1—C1—C4—N1	−179.4 (2)	O6—C17—C19—N2	−179.39 (19)
O1—C1—C4—C2	−62.6 (3)	O6—C17—C19—C16	64.8 (3)
O1—C1—C4—C3	58.5 (3)	O6—C17—C19—C18	−56.8 (3)
O3—C3—C4—N1	45.6 (3)	O7—C18—C19—N2	71.4 (3)
O3—C3—C4—C2	−72.8 (3)	O7—C18—C19—C16	−171.6 (2)
O3—C3—C4—C1	165.1 (2)	O7—C18—C19—C17	−47.9 (3)
C4—N1—C5—C6	179.3 (2)	C19—N2—C20—C21	−177.7 (2)
N1—C5—C6—C7	1.3 (4)	N2—C20—C21—C22	−0.2 (4)
N1—C5—C6—C11	−178.4 (2)	N2—C20—C21—C26	179.0 (2)
C5—C6—C7—O4	−1.3 (4)	C20—C21—C22—O8	0.8 (4)
C11—C6—C7—O4	178.4 (2)	C26—C21—C22—O8	−178.4 (2)
C5—C6—C7—C8	178.6 (2)	C20—C21—C22—C23	−179.1 (2)
C11—C6—C7—C8	−1.6 (4)	C26—C21—C22—C23	1.6 (4)
O4—C7—C8—C9	−177.6 (3)	O8—C22—C23—C24	177.6 (3)
C6—C7—C8—C9	2.5 (4)	C21—C22—C23—C24	−2.4 (4)
C7—C8—C9—C10	−0.7 (5)	C22—C23—C24—C25	0.1 (5)
C8—C9—C10—C15	−179.8 (3)	C23—C24—C25—C30	−178.5 (3)
C8—C9—C10—C11	−2.0 (5)	C23—C24—C25—C26	3.0 (5)
C15—C10—C11—C12	0.6 (4)	C30—C25—C26—C27	−1.3 (4)
C9—C10—C11—C12	−177.2 (3)	C24—C25—C26—C27	177.2 (3)
C15—C10—C11—C6	−179.4 (2)	C30—C25—C26—C21	177.8 (2)
C9—C10—C11—C6	2.8 (4)	C24—C25—C26—C21	−3.6 (4)
C5—C6—C11—C12	−1.2 (4)	C20—C21—C26—C27	1.2 (4)
C7—C6—C11—C12	179.0 (3)	C22—C21—C26—C27	−179.6 (3)
C5—C6—C11—C10	178.7 (2)	C20—C21—C26—C25	−177.9 (2)
C7—C6—C11—C10	−1.0 (4)	C22—C21—C26—C25	1.4 (4)
C10—C11—C12—C13	−0.7 (4)	C25—C26—C27—C28	0.9 (4)
C6—C11—C12—C13	179.3 (3)	C21—C26—C27—C28	−178.2 (3)
C11—C12—C13—C14	0.0 (5)	C26—C27—C28—C29	0.3 (5)
C12—C13—C14—C15	0.7 (5)	C27—C28—C29—C30	−1.1 (5)
C13—C14—C15—C10	−0.8 (5)	C28—C29—C30—C25	0.7 (5)
C11—C10—C15—C14	0.1 (4)	C26—C25—C30—C29	0.5 (5)
C9—C10—C15—C14	177.9 (3)	C24—C25—C30—C29	−178.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.86	1.91	2.587 (3)	135
N2—H2···O8	0.86	1.89	2.575 (2)	135
O1—H1C···O5i	0.82	1.90	2.715 (3)	172
O2—H2C···O8ii	0.82	1.77	2.589 (3)	173
O3—H3···O6iii	0.82	1.91	2.706 (3)	163
O5—H5···O4iv	0.82	1.84	2.650 (2)	171
O6—H6···O2v	0.82	1.81	2.609 (2)	163
O7—H7···O3vi	0.82	2.19	2.972 (2)	159

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1O4	0.86	1.91	2.587(3)	135
N2H2O8	0.86	1.89	2.575(2)	135
O1H1CO5i	0.82	1.90	2.715(3)	172
O2H2CO8ii	0.82	1.77	2.589(3)	173
O3H3O6iii	0.82	1.91	2.706(3)	163
O5H5O4iv	0.82	1.84	2.650(2)	171
O6H6O2v	0.82	1.81	2.609(2)	163
O7H7O3vi	0.82	2.19	2.972(2)	159

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .