2-(3-Hydroxy­prop­yl)isoindoline-1,3-dione: competition among hydrogen-bond acceptors

The title compound, C₁₁H₁₁NO₃, has two mol­ecules in the asymmetric unit, which differ in the orientation of their side-chain OH groups, allowing them to form inter­molecular O—H...O hydrogen bonds to different acceptors. In one case, the acceptor is the OH group of the other mol­ecule, and in the other case it is an imide O=C group. This is the first example in the N-substituted phthalimide series in which independent mol­ecules have different types of acceptor. Mol­ecular-orbital calculations place the greatest negative charge on the OH group.

S1. Comment

N-substituted phthalimides, (I), are of interest for biological activity in their own right (Lima et al., 2002) and as precursors for synthesis (Couture et al., 1998). Crystallographic studies have appeared recently in which the imide N atom bears a nonpolar substituent such as ethyl, (Ia) (Liang & Li, 2006c), or allyl, (Ib) (Warzecha et al., 2006). Other studies have investigated the situation when an N-alkyl substituent terminates with a hydrogen-bond donor, including hydroxymethyl, (Ic) (Liang & Li, 2006a), hydroxyethyl, (Id) (Liang & Li, 2006b), and a series of alkanoic acids, (Ie)–(Ii) (Feeder & Jones, 1996). The title compound, (Ij), corresponds to (If) with its carboxyl C═O group replaced by CH₂.

The two independent molecules of (Ij) are illustrated in Fig. 1. Their isoindoline ring systems are planar, with r.m.s. deviations of 0.01 Å, and the angle between these ring planes is only 1.65 (8)°. The bond distances and angles have values similar to those in related compounds. While the short-chain members of the series, (Ia)–(If), have Z' = 1, two of the longer-chain compounds, (Ig) and (Ii), have Z' = 2, the independent molecules differing in their conformation. As in (Ib) and (If)–(Ii), the alkyl chains of (Ij) lie out of the ring planes.

In the series of molecules (Ic)–(Ij), there is a single strong hydrogen-bond donor, the OH group of the hydroxyl or carboxyl group. A variety of O atoms compete to accept the hydrogen bond, viz. the OH group itself, the carboxyl O═C group if present and the two imide O atoms, which are aided by electron donation from the imide N atom. In both (Ic) and (Id), one of the imide O atoms is the acceptor. Such an O atom is even able to capture a hydrogen bond from the carboxyl group in (Ie) and (If), although the other members of this series, (Ig)–(Ii), form the familiar carboxyl dimers (Feeder & Jones, 1996).

In (Ij), the hydrogen bonding is more complex. Torsion angles along the independent hydroxyalkyl chains of (Ij) (Table 1) start with fairly typical values, but a drastic change at the end affects the orientation of the terminal OH groups. Fig. 2 shows a superposition made with Mercury (Macrae et al., 2006) of atoms C1 and C21, N2 and N22, C3 and C23, which gives an r.m.s. deviation 0.007 Å. This superposition leaves a distance of 0.680 Å between atoms O11 and O31, 1.017 Å between H11 and H31, and only 0.210 Å between H31 and O11. Alternative locations for H11 and H31 can be discounted in view of their successful rotating-group refinement and the small size of the maximum difference electron density, just 0.148 e Å^-3. Both OH groups donate hydrogen bonds (Fig. 3 and Table 2), but for O11/H11 the acceptor is imide atom O32, while for O31/H31 it is the hydroxyl atom O11 of the other independent molecule. C(10) chains (Bernstein et al., 1995) (highlighted in Fig. 3) are thereby created. Both hydrogen bonds show excellent linearity (O—H···O > 170°) and nearly identical distances. Unable to accept an O—H···O hydrogen bond, atom O31 accepts a reasonably strong C—H···O hydrogen bond. Other weak C—H···O interactions with H···O greater than 2.50 Å involving H25, H26 and H27 are not shown, but may make a small contribution to the stability of the crystal structure.

A derivative of (Ij) with complete 4,5,7-trichloro-6-(2,4-dimethylthiazol-5-yl) substitution on the phenyl ring (Fun et al., 2007) has successive torsion angles along the alkyl chain that are similar in magnitude within 18° to those for the C8–C10/O11 unit of (Ij), but C8—C9—C10—O11 is opposite in sign. The hydrogen bonding is entirely different, a thiazole N atom acting as acceptor for the OH group. The similar structure (If) is constructed from just one type of independent molecule and has a stronger intermolecular O—H···O hydrogen bond to an imide O atom, forming chains; its H···O and O···O distances are 1.82 and 2.689 Å (Feeder & Jones, 1996). Its carboxyl O(=C) atom only accepts C—H···O hydrogen bonds, and C—H···O hydrogen bonds link the chains into sheets.

To provide some insight into hydrogen-bond acceptor strength, Löwdin charges were calculated for the O atoms of (Ij) after optimization of geometry with GAMESS (Schmidt et al., 1993) in the 6–31G* basis set. The charge of -0.519 on the hydroxy O atom is considerably greater than those of -0.311 and -0.308 on the imide O atoms, suggesting that the former should be a more attractive hydrogen-bond acceptor. Taken together, the molecular orbital results for (Ij) and crystallographic results for (Ic), (Id) and (Ij) suggest that once the linkage between the phthalimide ring and the hydroxyl group becomes sufficiently long and flexible to position it properly, the latter group can assert its acceptor strength and receive an O—H···O or C—H···O hydrogen bond.

Related literature

For related literature, see: Bernstein et al. (1995); Couture et al. (1998); Feeder & Jones (1996); Fun et al. (2007); Liang & Li (2006a, 2006b, 2006c); Lima et al. (2002); Macrae et al. (2006); Schmidt et al. (1993); Warzecha et al. (2006).

S2. Experimental

Crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution in dichloromethane/hexane (8:1).

S3. Refinement

H atoms attached to C atom were positioned geometrically at C—H distances 0.93 or 0.97 Å and refined using a riding model with U_iso(H) values of 1.2U_eq(C). H atoms in the OH groups were refined as rotating groups with an O—H distance of 0.82 Å and U_iso(H) values of 1.5U_eq(O).

Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: CADABS (Gould & Smith, 1986); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures

	Fig. 1. The molecular structure and the atom-numbering scheme for (Ij). Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Superposition with Mercury (Macrae et al., 2006) of the phthalimide N atoms and the carbonyl C atoms in the two independent molecules of (Ij).
	Fig. 3. The unit-cell contents of (Ij). Heteroatoms are shown as ellipsoids, C atoms as spheres; H atoms have been omitted except for those involved in hydrogen bonds, which are shown as dashed lines. The C(10) motif is traced in solid lines. Other covalent bonds are shown as open bonds.

2-(3-Hydroxypropyl)isoindoline-1,3-dione

Crystal data

C11H11NO3	F(000) = 864
Mr = 205.21	Dx = 1.363 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 12.2439 (17) Å	θ = 8.0–12.1°
b = 7.4543 (8) Å	µ = 0.10 mm^−1
c = 21.973 (2) Å	T = 294 K
β = 94.282 (10)°	Block, colourless
V = 1999.9 (4) Å^3	0.43 × 0.42 × 0.40 mm
Z = 8

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.052
Radiation source: fine-focus sealed tube	θmax = 25.3°, θmin = 2.4°
Graphite monochromator	h = −14→14
w/2θ scans	k = −8→2
4424 measured reflections	l = −26→0
3583 independent reflections	3 standard reflections every 120 min
1805 reflections with I > 2σ(I)	intensity decay: 6%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0531P)^2 + 0.2706P] where P = (Fo^2 + 2Fc^2)/3
3583 reflections	(Δ/σ)max < 0.001
273 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.0857 (2)	1.0403 (4)	0.18923 (12)	0.0501 (7)
N2	−0.03687 (16)	1.0749 (3)	0.13558 (10)	0.0515 (6)
C3	−0.1115 (2)	1.1357 (4)	0.09001 (13)	0.0530 (7)
C3A	−0.2188 (2)	1.1443 (3)	0.11742 (12)	0.0473 (7)
C4	−0.3210 (2)	1.1925 (4)	0.09265 (14)	0.0620 (8)
H4	−0.3318	1.2292	0.0522	0.074*
C5	−0.4064 (2)	1.1847 (4)	0.12939 (17)	0.0717 (9)
H5	−0.4764	1.2155	0.1134	0.086*
C6	−0.3910 (2)	1.1324 (5)	0.18949 (17)	0.0735 (10)
H6	−0.4503	1.1309	0.2136	0.088*
C7	−0.2885 (2)	1.0822 (4)	0.21461 (13)	0.0631 (8)
H7	−0.2779	1.0451	0.2550	0.076*
C7A	−0.2027 (2)	1.0891 (4)	0.17735 (11)	0.0476 (7)
C8	0.0787 (2)	1.0381 (4)	0.12831 (14)	0.0603 (8)
H8A	0.0887	1.0180	0.0855	0.072*
H8B	0.0999	0.9293	0.1503	0.072*
C9	0.1525 (2)	1.1912 (4)	0.15169 (13)	0.0575 (8)
H9A	0.1367	1.2965	0.1266	0.069*
H9B	0.1364	1.2202	0.1931	0.069*
C10	0.2723 (2)	1.1459 (4)	0.15085 (13)	0.0622 (8)
H10A	0.2893	1.1239	0.1091	0.075*
H10B	0.3155	1.2478	0.1660	0.075*
O11	0.30206 (16)	0.9926 (3)	0.18694 (9)	0.0680 (6)
H11	0.3201	1.0241	0.2220	0.102*
O12	−0.03913 (15)	0.9773 (3)	0.23486 (9)	0.0700 (6)
O13	−0.09064 (17)	1.1723 (3)	0.03867 (9)	0.0769 (6)
C21	0.6527 (2)	0.6600 (4)	0.14759 (12)	0.0454 (6)
N22	0.58970 (15)	0.7259 (3)	0.09773 (9)	0.0457 (5)
C23	0.6517 (2)	0.7526 (4)	0.04758 (12)	0.0479 (7)
C23A	0.76489 (19)	0.6991 (3)	0.06836 (11)	0.0434 (6)
C24	0.8595 (2)	0.7014 (4)	0.03807 (12)	0.0545 (7)
H24	0.8593	0.7385	−0.0024	0.065*
C25	0.9551 (2)	0.6459 (4)	0.07051 (13)	0.0609 (8)
H25	1.0205	0.6470	0.0515	0.073*
C26	0.9555 (2)	0.5897 (4)	0.12984 (13)	0.0564 (8)
H26	1.0211	0.5533	0.1502	0.068*
C27	0.8603 (2)	0.5859 (4)	0.16019 (12)	0.0501 (7)
H27	0.8604	0.5470	0.2004	0.060*
C27A	0.76569 (18)	0.6419 (3)	0.12834 (11)	0.0409 (6)
C28	0.47280 (19)	0.7655 (4)	0.09744 (12)	0.0506 (7)
H28A	0.4559	0.8681	0.0713	0.061*
H28B	0.4555	0.7971	0.1384	0.061*
C29	0.4024 (2)	0.6092 (4)	0.07535 (13)	0.0571 (7)
H29A	0.4222	0.5047	0.1001	0.068*
H29B	0.4169	0.5817	0.0336	0.068*
C30	0.2817 (2)	0.6459 (5)	0.07820 (13)	0.0626 (8)
H30A	0.2644	0.7606	0.0590	0.075*
H30B	0.2403	0.5543	0.0552	0.075*
O31	0.24918 (17)	0.6489 (3)	0.13834 (9)	0.0682 (6)
H31	0.2683	0.7438	0.1547	0.102*
O32	0.61797 (14)	0.6272 (3)	0.19668 (8)	0.0591 (5)
O33	0.61543 (15)	0.8093 (3)	−0.00116 (8)	0.0668 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0541 (16)	0.0475 (17)	0.0478 (16)	−0.0066 (14)	−0.0020 (13)	−0.0021 (14)
N2	0.0443 (12)	0.0569 (15)	0.0540 (14)	0.0033 (11)	0.0068 (11)	0.0009 (12)
C3	0.0578 (17)	0.0473 (18)	0.0542 (17)	−0.0028 (14)	0.0062 (13)	0.0030 (14)
C3A	0.0502 (16)	0.0362 (16)	0.0553 (16)	−0.0014 (13)	0.0021 (12)	−0.0052 (14)
C4	0.0611 (18)	0.0515 (19)	0.0718 (19)	0.0090 (15)	−0.0059 (15)	0.0052 (16)
C5	0.0521 (18)	0.058 (2)	0.104 (3)	0.0035 (16)	−0.0008 (18)	−0.008 (2)
C6	0.0517 (18)	0.074 (2)	0.098 (3)	−0.0048 (17)	0.0234 (17)	−0.022 (2)
C7	0.0636 (18)	0.069 (2)	0.0584 (17)	−0.0113 (17)	0.0138 (14)	−0.0109 (17)
C7A	0.0520 (16)	0.0428 (16)	0.0480 (15)	−0.0056 (13)	0.0031 (12)	−0.0078 (13)
C8	0.0475 (16)	0.061 (2)	0.0724 (19)	0.0003 (15)	0.0074 (14)	−0.0078 (16)
C9	0.0553 (17)	0.0489 (18)	0.0694 (18)	0.0000 (14)	0.0131 (13)	0.0000 (15)
C10	0.0584 (18)	0.064 (2)	0.0659 (19)	−0.0061 (16)	0.0126 (14)	−0.0015 (17)
O11	0.0720 (13)	0.0697 (15)	0.0607 (12)	0.0117 (12)	−0.0064 (10)	−0.0127 (12)
O12	0.0674 (12)	0.0833 (17)	0.0570 (12)	−0.0044 (12)	−0.0098 (10)	0.0074 (12)
O13	0.0828 (14)	0.0903 (17)	0.0594 (13)	0.0039 (12)	0.0163 (10)	0.0184 (12)
C21	0.0470 (15)	0.0421 (17)	0.0470 (16)	−0.0019 (13)	0.0027 (12)	−0.0048 (13)
N22	0.0389 (11)	0.0510 (14)	0.0467 (12)	0.0046 (10)	0.0001 (9)	0.0024 (11)
C23	0.0537 (16)	0.0469 (17)	0.0430 (15)	0.0019 (13)	0.0030 (13)	−0.0045 (14)
C23A	0.0427 (14)	0.0415 (16)	0.0456 (15)	0.0028 (12)	0.0013 (11)	−0.0056 (13)
C24	0.0559 (17)	0.062 (2)	0.0462 (15)	−0.0042 (15)	0.0103 (13)	−0.0090 (14)
C25	0.0460 (16)	0.068 (2)	0.069 (2)	−0.0013 (15)	0.0098 (14)	−0.0155 (17)
C26	0.0437 (15)	0.057 (2)	0.0677 (19)	0.0063 (14)	−0.0027 (13)	−0.0102 (16)
C27	0.0506 (16)	0.0458 (17)	0.0531 (16)	0.0020 (13)	−0.0012 (13)	−0.0044 (14)
C27A	0.0394 (14)	0.0391 (16)	0.0439 (14)	0.0005 (12)	0.0016 (11)	−0.0038 (12)
C28	0.0386 (14)	0.0510 (18)	0.0619 (16)	0.0074 (13)	0.0018 (12)	−0.0034 (15)
C29	0.0476 (16)	0.060 (2)	0.0635 (17)	0.0020 (14)	0.0022 (13)	−0.0126 (16)
C30	0.0469 (16)	0.079 (2)	0.0617 (18)	−0.0073 (16)	0.0019 (13)	−0.0145 (17)
O31	0.0661 (12)	0.0731 (16)	0.0671 (13)	−0.0081 (12)	0.0175 (10)	−0.0021 (11)
O32	0.0562 (11)	0.0716 (14)	0.0507 (11)	0.0025 (10)	0.0109 (9)	0.0094 (10)
O33	0.0674 (12)	0.0840 (16)	0.0476 (11)	0.0090 (11)	−0.0048 (9)	0.0050 (11)

Geometric parameters (Å, º)

C1—O12	1.211 (3)	C21—O32	1.214 (3)
C1—N2	1.385 (3)	C21—N22	1.382 (3)
C1—C7A	1.481 (4)	C21—C27A	1.483 (3)
N2—C3	1.381 (3)	N22—C23	1.398 (3)
N2—C8	1.462 (3)	N22—C28	1.461 (3)
C3—O13	1.206 (3)	C23—O33	1.205 (3)
C3—C3A	1.487 (4)	C23—C23A	1.481 (3)
C3A—C4	1.374 (4)	C23A—C24	1.379 (3)
C3A—C7A	1.380 (3)	C23A—C27A	1.384 (3)
C4—C5	1.369 (4)	C24—C25	1.387 (4)
C4—H4	0.9300	C24—H24	0.9300
C5—C6	1.376 (4)	C25—C26	1.369 (4)
C5—H5	0.9300	C25—H25	0.9300
C6—C7	1.385 (4)	C26—C27	1.386 (4)
C6—H6	0.9300	C26—H26	0.9300
C7—C7A	1.380 (4)	C27—C27A	1.373 (3)
C7—H7	0.9300	C27—H27	0.9300
C8—C9	1.521 (4)	C28—C29	1.508 (4)
C8—H8A	0.9700	C28—H28A	0.9700
C8—H8B	0.9700	C28—H28B	0.9700
C9—C10	1.507 (4)	C29—C30	1.508 (3)
C9—H9A	0.9700	C29—H29A	0.9700
C9—H9B	0.9700	C29—H29B	0.9700
C10—O11	1.423 (3)	C30—O31	1.409 (3)
C10—H10A	0.9700	C30—H30A	0.9700
C10—H10B	0.9700	C30—H30B	0.9700
O11—H11	0.8200	O31—H31	0.8200
O12—C1—N2	124.8 (2)	O32—C21—N22	124.3 (2)
O12—C1—C7A	129.1 (3)	O32—C21—C27A	129.2 (2)
N2—C1—C7A	106.1 (2)	N22—C21—C27A	106.5 (2)
C3—N2—C1	111.9 (2)	C21—N22—C23	111.8 (2)
C3—N2—C8	125.2 (2)	C21—N22—C28	124.3 (2)
C1—N2—C8	122.8 (2)	C23—N22—C28	123.9 (2)
O13—C3—N2	125.3 (2)	O33—C23—N22	124.4 (2)
O13—C3—C3A	128.6 (3)	O33—C23—C23A	130.0 (2)
N2—C3—C3A	106.1 (2)	N22—C23—C23A	105.6 (2)
C4—C3A—C7A	121.1 (3)	C24—C23A—C27A	121.1 (2)
C4—C3A—C3	131.0 (3)	C24—C23A—C23	130.4 (2)
C7A—C3A—C3	107.8 (2)	C27A—C23A—C23	108.5 (2)
C5—C4—C3A	117.9 (3)	C23A—C24—C25	117.1 (3)
C5—C4—H4	121.0	C23A—C24—H24	121.4
C3A—C4—H4	121.0	C25—C24—H24	121.4
C4—C5—C6	121.4 (3)	C26—C25—C24	121.5 (3)
C4—C5—H5	119.3	C26—C25—H25	119.2
C6—C5—H5	119.3	C24—C25—H25	119.2
C5—C6—C7	121.0 (3)	C25—C26—C27	121.4 (3)
C5—C6—H6	119.5	C25—C26—H26	119.3
C7—C6—H6	119.5	C27—C26—H26	119.3
C7A—C7—C6	117.5 (3)	C27A—C27—C26	117.2 (3)
C7A—C7—H7	121.3	C27A—C27—H27	121.4
C6—C7—H7	121.3	C26—C27—H27	121.4
C3A—C7A—C7	121.1 (3)	C27—C27A—C23A	121.7 (2)
C3A—C7A—C1	108.0 (2)	C27—C27A—C21	130.7 (2)
C7—C7A—C1	130.9 (3)	C23A—C27A—C21	107.6 (2)
N2—C8—C9	112.2 (2)	N22—C28—C29	112.4 (2)
N2—C8—H8A	109.2	N22—C28—H28A	109.1
C9—C8—H8A	109.2	C29—C28—H28A	109.1
N2—C8—H8B	109.2	N22—C28—H28B	109.1
C9—C8—H8B	109.2	C29—C28—H28B	109.1
H8A—C8—H8B	107.9	H28A—C28—H28B	107.9
C10—C9—C8	112.5 (2)	C28—C29—C30	112.6 (2)
C10—C9—H9A	109.1	C28—C29—H29A	109.1
C8—C9—H9A	109.1	C30—C29—H29A	109.1
C10—C9—H9B	109.1	C28—C29—H29B	109.1
C8—C9—H9B	109.1	C30—C29—H29B	109.1
H9A—C9—H9B	107.8	H29A—C29—H29B	107.8
O11—C10—C9	112.5 (2)	O31—C30—C29	112.9 (2)
O11—C10—H10A	109.1	O31—C30—H30A	109.0
C9—C10—H10A	109.1	C29—C30—H30A	109.0
O11—C10—H10B	109.1	O31—C30—H30B	109.0
C9—C10—H10B	109.1	C29—C30—H30B	109.0
H10A—C10—H10B	107.8	H30A—C30—H30B	107.8
C10—O11—H11	109.5	C30—O31—H31	109.5
O12—C1—N2—C3	176.1 (3)	O32—C21—N22—C23	179.4 (3)
C7A—C1—N2—C3	−1.8 (3)	C27A—C21—N22—C23	−0.1 (3)
O12—C1—N2—C8	0.0 (4)	O32—C21—N22—C28	0.2 (4)
C7A—C1—N2—C8	−177.9 (2)	C27A—C21—N22—C28	−179.2 (2)
C1—N2—C3—O13	−178.5 (3)	C21—N22—C23—O33	−179.9 (3)
C8—N2—C3—O13	−2.6 (5)	C28—N22—C23—O33	−0.8 (4)
C1—N2—C3—C3A	1.1 (3)	C21—N22—C23—C23A	−0.4 (3)
C8—N2—C3—C3A	177.0 (2)	C28—N22—C23—C23A	178.8 (2)
O13—C3—C3A—C4	0.9 (5)	O33—C23—C23A—C24	0.9 (5)
N2—C3—C3A—C4	−178.8 (3)	N22—C23—C23A—C24	−178.6 (3)
O13—C3—C3A—C7A	179.8 (3)	O33—C23—C23A—C27A	−179.8 (3)
N2—C3—C3A—C7A	0.1 (3)	N22—C23—C23A—C27A	0.7 (3)
C7A—C3A—C4—C5	0.3 (4)	C27A—C23A—C24—C25	−0.7 (4)
C3—C3A—C4—C5	179.0 (3)	C23—C23A—C24—C25	178.5 (3)
C3A—C4—C5—C6	0.7 (5)	C23A—C24—C25—C26	0.6 (4)
C4—C5—C6—C7	−1.3 (5)	C24—C25—C26—C27	−0.1 (5)
C5—C6—C7—C7A	0.9 (5)	C25—C26—C27—C27A	−0.4 (4)
C4—C3A—C7A—C7	−0.7 (4)	C26—C27—C27A—C23A	0.3 (4)
C3—C3A—C7A—C7	−179.7 (3)	C26—C27—C27A—C21	−177.7 (3)
C4—C3A—C7A—C1	177.8 (2)	C24—C23A—C27A—C27	0.3 (4)
C3—C3A—C7A—C1	−1.2 (3)	C23—C23A—C27A—C27	−179.1 (2)
C6—C7—C7A—C3A	0.1 (4)	C24—C23A—C27A—C21	178.7 (2)
C6—C7—C7A—C1	−178.0 (3)	C23—C23A—C27A—C21	−0.7 (3)
O12—C1—C7A—C3A	−175.9 (3)	O32—C21—C27A—C27	−0.7 (5)
N2—C1—C7A—C3A	1.9 (3)	N22—C21—C27A—C27	178.7 (3)
O12—C1—C7A—C7	2.4 (5)	O32—C21—C27A—C23A	−178.9 (3)
N2—C1—C7A—C7	−179.8 (3)	N22—C21—C27A—C23A	0.5 (3)
C1—N2—C8—C9	−85.0 (3)	C21—N22—C28—C29	−92.8 (3)
C3—N2—C8—C9	99.5 (3)	C23—N22—C28—C29	88.1 (3)
N2—C8—C9—C10	173.6 (2)	N22—C28—C29—C30	176.9 (2)
C8—C9—C10—O11	−59.0 (3)	C28—C29—C30—O31	−71.6 (3)
C9—C10—O11—H11	−89	C29—C30—O31—H31	76

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O31—H31···O11	0.82	2.02	2.832 (3)	173
O11—H11···O32^i	0.82	2.04	2.851 (3)	171
C7—H7···O31^ii	0.93	2.47	3.269 (3)	144
C25—H25···O13^iii	0.93	2.59	3.307 (4)	134
C26—H26···O12^iv	0.93	2.58	3.183 (4)	123
C27—H27···O12^iv	0.93	2.57	3.165 (3)	122

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, −y+2, −z; (iv) −x+1, y−1/2, −z+1/2.