A comparison of the supramolecular structures of 1-(6-amino-1,3-benzodioxol-5-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one and 1-(6-amino-1,3-benzodioxol-5-yl)-3-[4-(N,N-dimethylamino)phenyl]prop-2-en-1-one

1-(6-Amino-1,3-benzodioxol-5-yl)-3-(3,4,5-tri­methoxy­phenyl)­prop-2-en-1-one, C₁₉H₁₉NO₆, (I), contains an intramolecular N-H...O hydrogen bond and a weak C-H...O hydrogen bond, which forms a C(10) chain motif running parallel to the c axis. The 6-amino-1,3-benzo­dioxol-5-yl moieties are involved in [pi]-[pi] stacking. 1-(6-Amino-1,3-benzo­dioxol-5-yl)-3-[4-(N,N-di­methyl­amino)­phenyl]­prop-2-en-1-one, C₁₈H₁₈N₂O₃, (II), crystallizes with two mol­ecules in the asymmetric unit. The main feature of the supramolecular structure of (II) is the formation of a centrosymmetric hydrogen-bonded tetramer with an R₈⁴(16) motif.

S1. Comment

Many synthetic or naturally occurring compounds containing the 1,3-dioxolyl group in their structures are very important because of their pharmacological properties (Ma et al., 1987; Ohta & Kimoto, 1976; Schlunke & Egli, 1972; Krause & Goeber, 1972; Gabrielsen et al., 1992). Chalcones (1,3-diarylpropenones) have been widely used as starting materials in numerous synthetic reactions (Awad et al., 1960; Coudert et al., 1988; Carrie & Rochard, 1963), including the preparation of fused-ring heterocyclic compounds (Insuasty et al., 1992, 1997; Kolos et al., 1996). We have prepared the title compounds, (I) and (II), as intermediates in the synthesis of novel dihydroquinolinones. This is a class of compounds with interesting pharmaceutical properties (Pfizer, 1980; Jordis et al., 1991; Baker et al., 1990), since the 1,3-dioxolyl residue in their frameworks enhances their practical applications. \sch

The molecular structures of (I) and of the two independent molecules of (II) are shown in Figs. 1 and 2, respectively. The dioxol-5-yl groups in all three molecules have C2 envelope puckers. In (I), a strong intramolecular hydrogen bond is observed with an S(6) motif via N5—H5A···O8 (Bernstein et al., 1995) (Fig. 1, Table 1), and likewise in (II) via N15—H15A···O18 and N25—H25A···O28 (Fig. 2, Table 2).

The supramolecular structures of (I) and (II) are completely different. In (I), a C(10) motif is formed via C16—H16···O1(x, -1/2 - y, z - 1/2), creating a chain which runs parallel to the c axis. Two such anti-parallel chains are shown in Fig. 3. Atom H5B is not involved in any hydrogen bonding. In (II), however, the equivalent H atoms H15B and H25B are involved in strong hydrogen bonds via N15—N15B···O28(1 - x, 1 - y, 1 - z) and N25—H25B···O18, linking molecules 1 and 2 to form a tetramer with an R₈⁴(16) motif (Fig. 4). Such motifs occur centred at (l + 1/2, m + 1/2, n + 1/2), where l, m and n are integer or zero. The weak C14—H14···O28(1 - x, 1 - y, 1 - z) and C24—H24···O18 hydrogen bonds help to reinforce this tetramer structure. The tetramers are linked to each other by weak hydrogen bonds via C212—H212···O13(x, y, z - 1) and C212(1 - x, 1 - y, z)-H212(1 - x, 1 - y, z)···O13(1 - x, 1 - y, 1 - z), which form bridging R₄⁴(26) rings along with the N15—H15···O28 hydrogen bonds of the tetramer (Fig. 5).

In (I), there is π···π stacking between the benzo-1,3-dioxol-5-yl groups, where the rings defined by O1—C2—O3—C3a—C7a and C3a—C4—C5—C6—C7—C7a are stacked such that the distance between the centres of gravity of the rings is 3.7276 (9) Å, the dihedral angle is 3.50°, the perpendicular distance from the centre of gravity of the former ring at (x, y, z) to the latter at (x, 1 + y, z) is 3.368 Å and the perpendicular distance from the centre of gravity of the latter ring at (x, y, z) to the former at (x, y - 1, z) is 3.445 Å (Fig. 6). It is worth noting that the dihedral angle between these planes, 3.50°, is in fact the dihedral angle between the two components of the benzo-1,3-dioxol-5-yl group, which is not in itself planar. There is no π–π stacking in (II).

S2. Experimental

For (I), a mixture of 6'-amino-3',4'-(methylenedioxy)acetophenone (0.50 g, 2.79 mmol), 3,4,5-trimethoxybenzaldehyde (2.79 mmol), ethanol (10 ml) and NaOH (0.5 ml, 20% aq.) was heated to 333–343 K for 10–15 min and the reaction monitored by thin-layer chromatography. After cooling, the solid formed was filtered and washed with ethanol to yield pure (I) as orange crystals (93% yield; m.p. 464 K). For (II), a mixture of 6'-amino-3',4'-(methylenedioxy)acetophenone (0.50 g, 2.79 mmol), 4-(N,N-dimethylamino)benzaldehyde (2.79 mmol), ethanol (10 ml) and NaOH (0.5 ml, 20% aq.) was heated to 333–343 K for 10–15 min and the reaction monitored by thin-layer chromatography. After cooling, the solid formed was filtered and washed with ethanol to yield pure (II) as purple crystals (46% yield; m.p. 435 K). For both (I) and (II), crystals suitable for single-crystal X-ray diffraction were selected directly from the prepared samples.

S3. Refinement

For both compounds, H atoms were treated as riding, with C—H = 0.95 to 0.99 Å. In the case of the N—H bonds, the H atoms were initially located on a difference Fourier map. The bond lengths were then DFIXed (SHELXL97; Sheldrick, 1997) to 0.880 Å with an e.s.d. of 0.005 until a value close to 0.88 Å was obtained, at which stage they were AFIXed (SHELXL97) and allowed to ride on their parent atoms.

Computing details

For both compounds, data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures

	Fig. 1. A molecular view of (I) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Views of the two independent molecules of (II) with the atom-numbering schemes. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 3. A view of the crystal structure of (I) looking down the b axis, showing two anti-parallel C(10) chains [symmetry code: (i) x, -1/2 - y, z - 1/2].
	Fig. 4. A view of the tetramer formed by the molecules of (II) at (x, y, z) and (1 - x, 1 - y, 1 - z). For the sake of clarity, H atoms bonded to C have been omitted [symmetry code: (ii) 1 - x, 1 - y, 1 - z].
	Fig. 5. A view of the R4^4(26) rings which link the tetramers in (II) [symmetry codes: (ii) 1 - x, 1 - y, 1 - z; (iii) x, y, z - 1; (iv) 1 - x, 1 - y, -z]. For the sake of clarity, H atoms bonded to C or N and not involved in this motif are omitted, as is the unit-cell box.
	Fig. 6. A view of the π···π stacking in (I). For the sake of clarity the unit-cell box has been omitted.

(I) 1-(6-amino-1,3-benzodioxol-5-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

Crystal data

C19H19NO6	Dx = 1.451 Mg m^−3
Mr = 357.35	Melting point: 464 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 23.5477 (4) Å	Cell parameters from 3622 reflections
b = 4.9605 (1) Å	θ = 3.1–27.5°
c = 14.2556 (8) Å	µ = 0.11 mm^−1
β = 100.702 (1)°	T = 150 K
V = 1636.21 (10) Å^3	Block, orange
Z = 4	0.4 × 0.1 × 0.1 mm
F(000) = 752

Data collection

Nonius KappaCCD diffractometer	3622 independent reflections
Radiation source: fine-focus sealed X-ray tube	2832 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
ϕ and ω scans with κ offsets	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −30→30
Tmin = 0.958, Tmax = 0.989	k = −6→6
11152 measured reflections	l = −18→18

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0675P)^2 + 0.3552P] where P = (Fo^2 + 2Fc^2)/3
3622 reflections	(Δ/σ)max < 0.001
238 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

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

	x	y	z	Uiso*/Ueq
O1	0.16792 (4)	0.9086 (2)	0.04794 (8)	0.0228 (3)
C2	0.12417 (6)	1.0264 (3)	−0.02328 (11)	0.0216 (3)
O3	0.06873 (4)	0.9492 (2)	−0.00242 (8)	0.0228 (3)
C3a	0.07999 (6)	0.7506 (3)	0.06504 (10)	0.0180 (3)
C4	0.04112 (6)	0.5963 (3)	0.10051 (10)	0.0180 (3)
C5	0.06256 (6)	0.3950 (3)	0.16848 (10)	0.0163 (3)
N5	0.02326 (5)	0.2365 (2)	0.20091 (9)	0.0203 (3)
C6	0.12324 (6)	0.3693 (3)	0.20219 (10)	0.0160 (3)
C7	0.16178 (6)	0.5382 (3)	0.16234 (10)	0.0183 (3)
C7a	0.13948 (6)	0.7212 (3)	0.09496 (11)	0.0171 (3)
C8	0.14568 (6)	0.1787 (3)	0.27912 (10)	0.0169 (3)
O8	0.11443 (4)	0.0101 (2)	0.30938 (7)	0.0210 (3)
C9	0.20706 (6)	0.2028 (3)	0.32790 (11)	0.0195 (3)
C10	0.22878 (6)	0.0449 (3)	0.40162 (11)	0.0188 (3)
C11	0.28618 (6)	0.0587 (3)	0.46207 (10)	0.0179 (3)
C12	0.32891 (6)	0.2392 (3)	0.44517 (10)	0.0180 (3)
C13	0.38233 (6)	0.2436 (3)	0.50627 (11)	0.0180 (3)
O13	0.42754 (4)	0.4040 (2)	0.49442 (8)	0.0219 (3)
C131	0.42037 (7)	0.5680 (3)	0.41009 (12)	0.0243 (4)
C14	0.39292 (6)	0.0760 (3)	0.58688 (11)	0.0185 (3)
O14	0.44395 (4)	0.1016 (2)	0.65090 (7)	0.0227 (3)
C141	0.48413 (7)	−0.1152 (3)	0.64751 (12)	0.0252 (4)
C15	0.35021 (7)	−0.1042 (3)	0.60318 (10)	0.0192 (3)
O15	0.36428 (5)	−0.2597 (2)	0.68360 (8)	0.0255 (3)
C151	0.32121 (7)	−0.4413 (3)	0.70400 (12)	0.0270 (4)
C16	0.29745 (6)	−0.1155 (3)	0.54069 (10)	0.0187 (3)
H2A	0.1280	0.9611	−0.0874	0.026*
H2B	0.1280	1.2252	−0.0222	0.026*
H4	0.0007	0.6227	0.0803	0.022*
H5A	0.0356	0.0908	0.2337	0.024*
H5B	−0.0121	0.2377	0.1673	0.024*
H7	0.2024	0.5225	0.1828	0.022*
H9	0.2312	0.3330	0.3062	0.023*
H10	0.2040	−0.0932	0.4167	0.023*
H12	0.3214	0.3582	0.3921	0.022*
H13A	0.4094	0.4538	0.3535	0.036*
H13B	0.4568	0.6602	0.4071	0.036*
H13C	0.3900	0.7020	0.4121	0.036*
H14A	0.4655	−0.2873	0.6568	0.038*
H14B	0.5181	−0.0905	0.6981	0.038*
H14C	0.4962	−0.1154	0.5853	0.038*
H15A	0.2877	−0.3387	0.7159	0.041*
H15B	0.3370	−0.5480	0.7607	0.041*
H15C	0.3093	−0.5620	0.6495	0.041*
H16	0.2689	−0.2416	0.5513	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0178 (5)	0.0245 (6)	0.0260 (6)	0.0017 (4)	0.0043 (5)	0.0090 (4)
C2	0.0208 (8)	0.0234 (8)	0.0200 (8)	0.0017 (6)	0.0028 (6)	0.0049 (6)
O3	0.0191 (6)	0.0259 (6)	0.0228 (6)	0.0044 (4)	0.0026 (4)	0.0079 (4)
C3a	0.0196 (8)	0.0185 (7)	0.0150 (7)	0.0039 (6)	0.0009 (6)	−0.0007 (5)
C4	0.0136 (7)	0.0203 (7)	0.0188 (8)	0.0026 (5)	−0.0002 (6)	−0.0022 (6)
C5	0.0148 (7)	0.0174 (7)	0.0166 (7)	−0.0004 (5)	0.0023 (6)	−0.0035 (5)
N5	0.0147 (6)	0.0198 (6)	0.0258 (7)	−0.0010 (5)	0.0019 (5)	0.0019 (5)
C6	0.0165 (7)	0.0142 (7)	0.0168 (7)	0.0018 (5)	0.0018 (6)	−0.0018 (5)
C7	0.0129 (7)	0.0218 (7)	0.0195 (8)	0.0019 (6)	0.0012 (6)	−0.0013 (6)
C7a	0.0164 (7)	0.0175 (7)	0.0180 (8)	−0.0007 (5)	0.0048 (6)	−0.0005 (5)
C8	0.0172 (7)	0.0168 (7)	0.0168 (7)	0.0012 (5)	0.0036 (6)	−0.0029 (5)
O8	0.0198 (5)	0.0194 (5)	0.0230 (6)	−0.0021 (4)	0.0021 (4)	0.0026 (4)
C9	0.0162 (7)	0.0220 (7)	0.0202 (8)	−0.0009 (6)	0.0028 (6)	0.0022 (6)
C10	0.0170 (7)	0.0193 (7)	0.0199 (8)	−0.0003 (6)	0.0026 (6)	−0.0007 (6)
C11	0.0163 (7)	0.0209 (7)	0.0164 (8)	0.0031 (6)	0.0026 (6)	−0.0012 (6)
C12	0.0180 (7)	0.0190 (7)	0.0163 (8)	0.0028 (6)	0.0016 (6)	0.0004 (6)
C13	0.0179 (7)	0.0159 (7)	0.0203 (8)	0.0004 (5)	0.0035 (6)	−0.0027 (6)
O13	0.0187 (6)	0.0223 (6)	0.0233 (6)	−0.0044 (4)	−0.0001 (4)	0.0025 (4)
C131	0.0238 (8)	0.0217 (8)	0.0272 (9)	−0.0038 (6)	0.0043 (7)	0.0048 (6)
C14	0.0159 (7)	0.0203 (7)	0.0176 (8)	0.0019 (6)	−0.0013 (6)	−0.0034 (6)
O14	0.0197 (6)	0.0223 (6)	0.0223 (6)	0.0027 (4)	−0.0059 (4)	−0.0029 (4)
C141	0.0187 (8)	0.0256 (8)	0.0284 (9)	0.0033 (6)	−0.0026 (7)	0.0016 (6)
C15	0.0217 (8)	0.0188 (7)	0.0167 (8)	0.0040 (6)	0.0027 (6)	0.0009 (6)
O15	0.0245 (6)	0.0297 (6)	0.0207 (6)	−0.0004 (5)	−0.0005 (5)	0.0095 (4)
C151	0.0289 (9)	0.0262 (8)	0.0267 (9)	0.0020 (7)	0.0070 (7)	0.0085 (6)
C16	0.0180 (7)	0.0171 (7)	0.0210 (8)	−0.0001 (5)	0.0036 (6)	0.0003 (6)

Geometric parameters (Å, º)

O1—C7a	1.3887 (17)	C11—C12	1.401 (2)
O1—C2	1.4301 (19)	C11—C16	1.401 (2)
C2—O3	1.4436 (18)	C12—C13	1.391 (2)
C2—H2A	0.9900	C12—H12	0.9500
C2—H2B	0.9900	C13—O13	1.3646 (17)
O3—C3a	1.3677 (17)	C13—C14	1.403 (2)
C3a—C4	1.361 (2)	O13—C131	1.4352 (18)
C3a—C7a	1.394 (2)	C131—H13A	0.9800
C4—C5	1.417 (2)	C131—H13B	0.9800
C4—H4	0.9500	C131—H13C	0.9800
C5—N5	1.3594 (18)	C14—O14	1.3732 (18)
C5—C6	1.426 (2)	C14—C15	1.397 (2)
N5—H5A	0.8801	O14—C141	1.4392 (18)
N5—H5B	0.8800	C141—H14A	0.9800
C6—C7	1.428 (2)	C141—H14B	0.9800
C6—C8	1.470 (2)	C141—H14C	0.9800
C7—C7a	1.355 (2)	C15—O15	1.3704 (18)
C7—H7	0.9500	C15—C16	1.389 (2)
C8—O8	1.2431 (17)	O15—C151	1.4262 (19)
C8—C9	1.488 (2)	C151—H15A	0.9800
C9—C10	1.334 (2)	C151—H15B	0.9800
C9—H9	0.9500	C151—H15C	0.9800
C10—C11	1.463 (2)	C16—H16	0.9500
C10—H10	0.9500
C7a—O1—C2	105.54 (11)	C12—C11—C10	122.89 (13)
O1—C2—O3	107.76 (11)	C16—C11—C10	117.35 (13)
O1—C2—H2A	110.2	C13—C12—C11	119.83 (13)
O3—C2—H2A	110.2	C13—C12—H12	120.1
O1—C2—H2B	110.2	C11—C12—H12	120.1
O3—C2—H2B	110.2	O13—C13—C12	124.57 (13)
H2A—C2—H2B	108.5	O13—C13—C14	115.02 (13)
C3a—O3—C2	105.75 (11)	C12—C13—C14	120.41 (13)
C4—C3a—O3	127.62 (13)	C13—O13—C131	117.45 (11)
C4—C3a—C7a	122.31 (13)	O13—C131—H13A	109.5
O3—C3a—C7a	110.06 (12)	O13—C131—H13B	109.5
C3a—C4—C5	118.13 (13)	H13A—C131—H13B	109.5
C3a—C4—H4	120.9	O13—C131—H13C	109.5
C5—C4—H4	120.9	H13A—C131—H13C	109.5
N5—C5—C4	117.48 (13)	H13B—C131—H13C	109.5
N5—C5—C6	122.44 (13)	O14—C14—C15	121.12 (13)
C4—C5—C6	120.06 (13)	O14—C14—C13	119.35 (13)
C5—N5—H5A	118.5	C15—C14—C13	119.44 (13)
C5—N5—H5B	116.5	C14—O14—C141	114.08 (11)
H5A—N5—H5B	118.7	O14—C141—H14A	109.5
C5—C6—C7	118.96 (13)	O14—C141—H14B	109.5
C5—C6—C8	120.53 (13)	H14A—C141—H14B	109.5
C7—C6—C8	120.47 (13)	O14—C141—H14C	109.5
C7a—C7—C6	118.94 (13)	H14A—C141—H14C	109.5
C7a—C7—H7	120.5	H14B—C141—H14C	109.5
C6—C7—H7	120.5	O15—C15—C16	124.23 (13)
C7—C7a—O1	129.24 (13)	O15—C15—C14	115.44 (13)
C7—C7a—C3a	121.48 (13)	C16—C15—C14	120.32 (13)
O1—C7a—C3a	109.24 (12)	C15—O15—C151	117.08 (12)
O8—C8—C6	122.52 (13)	O15—C151—H15A	109.5
O8—C8—C9	118.57 (13)	O15—C151—H15B	109.5
C6—C8—C9	118.71 (12)	H15A—C151—H15B	109.5
C10—C9—C8	121.19 (13)	O15—C151—H15C	109.5
C10—C9—H9	119.4	H15A—C151—H15C	109.5
C8—C9—H9	119.4	H15B—C151—H15C	109.5
C9—C10—C11	127.83 (14)	C15—C16—C11	120.16 (13)
C9—C10—H10	116.1	C15—C16—H16	119.9
C11—C10—H10	116.1	C11—C16—H16	119.9
C12—C11—C16	119.75 (13)
C7a—O1—C2—O3	12.88 (15)	C6—C8—C9—C10	176.25 (13)
O1—C2—O3—C3a	−12.08 (15)	C8—C9—C10—C11	−174.20 (13)
C2—O3—C3a—C4	−173.10 (14)	C9—C10—C11—C12	−4.3 (2)
C2—O3—C3a—C7a	6.61 (15)	C9—C10—C11—C16	174.68 (15)
O3—C3a—C4—C5	178.10 (13)	C16—C11—C12—C13	0.3 (2)
C7a—C3a—C4—C5	−1.6 (2)	C10—C11—C12—C13	179.21 (13)
C3a—C4—C5—N5	−177.85 (12)	C11—C12—C13—O13	177.52 (13)
C3a—C4—C5—C6	3.8 (2)	C11—C12—C13—C14	−2.5 (2)
N5—C5—C6—C7	178.10 (13)	C12—C13—O13—C131	−3.7 (2)
C4—C5—C6—C7	−3.6 (2)	C14—C13—O13—C131	176.36 (12)
N5—C5—C6—C8	−4.0 (2)	O13—C13—C14—O14	5.97 (19)
C4—C5—C6—C8	174.26 (13)	C12—C13—C14—O14	−173.98 (13)
C5—C6—C7—C7a	1.2 (2)	O13—C13—C14—C15	−177.30 (12)
C8—C6—C7—C7a	−176.67 (13)	C12—C13—C14—C15	2.7 (2)
C6—C7—C7a—O1	178.55 (13)	C15—C14—O14—C141	76.27 (17)
C6—C7—C7a—C3a	1.0 (2)	C13—C14—O14—C141	−107.06 (15)
C2—O1—C7a—C7	173.31 (15)	O14—C14—C15—O15	−3.3 (2)
C2—O1—C7a—C3a	−8.92 (15)	C13—C14—C15—O15	−179.96 (12)
C4—C3a—C7a—C7	−0.8 (2)	O14—C14—C15—C16	175.99 (13)
O3—C3a—C7a—C7	179.42 (13)	C13—C14—C15—C16	−0.7 (2)
C4—C3a—C7a—O1	−178.82 (13)	C16—C15—O15—C151	−0.8 (2)
O3—C3a—C7a—O1	1.45 (16)	C14—C15—O15—C151	178.41 (12)
C5—C6—C8—O8	9.4 (2)	O15—C15—C16—C11	177.63 (13)
C7—C6—C8—O8	−172.82 (13)	C14—C15—C16—C11	−1.6 (2)
C5—C6—C8—C9	−165.62 (13)	C12—C11—C16—C15	1.8 (2)
C7—C6—C8—C9	12.2 (2)	C10—C11—C16—C15	−177.21 (13)
O8—C8—C9—C10	1.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···O8	0.88	2.01	2.651 (2)	129
C16—H16···O1^i	0.95	2.51	3.398 (2)	155

Symmetry code: (i) x, −y+1/2, z+1/2.

(II) 1-(6-amino-1,3-benzodioxol-5-yl)-3-[4-(N,N-dimethylamino)phenyl]prop-2-en-1-one

Crystal data

C18H18N2O3	F(000) = 656
Mr = 310.34	Dx = 1.339 Mg m^−3
Triclinic, P1	Melting point: 435 K
a = 9.5849 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.3218 (4) Å	Cell parameters from 6884 reflections
c = 13.3304 (4) Å	θ = 3.1–27.5°
α = 83.4617 (14)°	µ = 0.09 mm^−1
β = 80.2411 (17)°	T = 150 K
γ = 85.7271 (16)°	Block, orange
V = 1539.04 (8) Å^3	0.22 × 0.14 × 0.12 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	6884 independent reflections
Radiation source: fine-focus sealed X-ray tube	4873 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.085
ϕ and ω scans with κ offsets	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −12→12
Tmin = 0.980, Tmax = 0.989	k = −15→15
23078 measured reflections	l = −17→17

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.154	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0927P)^2] where P = (Fo^2 + 2Fc^2)/3
6884 reflections	(Δ/σ)max = 0.006
419 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.34 e Å^−3

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

	x	y	z	Uiso*/Ueq
O11	−0.02777 (11)	0.75297 (9)	0.87894 (8)	0.0362 (3)
C12	−0.01144 (17)	0.65439 (14)	0.94317 (13)	0.0349 (4)
O13	0.13044 (11)	0.60803 (9)	0.91563 (8)	0.0324 (3)
C13a	0.18474 (15)	0.66717 (12)	0.82576 (11)	0.0257 (3)
C14	0.30993 (15)	0.64707 (12)	0.76417 (11)	0.0276 (3)
C15	0.34538 (15)	0.72053 (12)	0.67488 (11)	0.0259 (3)
N15	0.47153 (13)	0.69853 (11)	0.61323 (10)	0.0333 (3)
C16	0.25060 (15)	0.81109 (11)	0.65143 (11)	0.0237 (3)
C17	0.12044 (16)	0.82630 (12)	0.71898 (11)	0.0270 (3)
C17a	0.09087 (15)	0.75469 (12)	0.80356 (12)	0.0266 (3)
C18	0.28570 (16)	0.88751 (12)	0.55863 (11)	0.0261 (3)
O18	0.39602 (11)	0.87251 (9)	0.49523 (8)	0.0306 (3)
C19	0.19130 (16)	0.98540 (12)	0.54110 (12)	0.0274 (3)
C110	0.22813 (16)	1.06686 (12)	0.46786 (12)	0.0281 (3)
C111	0.14871 (16)	1.17030 (12)	0.44964 (12)	0.0267 (3)
C112	0.02860 (16)	1.20526 (12)	0.51632 (12)	0.0283 (3)
C113	−0.04435 (16)	1.30398 (12)	0.49728 (12)	0.0281 (3)
C114	−0.00003 (15)	1.37594 (12)	0.40891 (12)	0.0269 (3)
N141	−0.07035 (14)	1.47595 (11)	0.39143 (10)	0.0320 (3)
C142	−0.20735 (17)	1.50204 (14)	0.45120 (14)	0.0376 (4)
C143	−0.02794 (18)	1.54618 (13)	0.29822 (13)	0.0373 (4)
C115	0.11977 (16)	1.34160 (13)	0.34170 (12)	0.0291 (4)
C116	0.19116 (16)	1.24217 (12)	0.36211 (12)	0.0290 (4)
O21	0.13133 (15)	0.90490 (9)	0.04973 (10)	0.0502 (4)
C22	0.0878 (2)	1.00143 (14)	0.09912 (14)	0.0450 (5)
O23	0.16077 (14)	0.99874 (9)	0.18490 (9)	0.0467 (3)
C23a	0.21602 (17)	0.89328 (12)	0.19967 (12)	0.0320 (4)
C24	0.28336 (17)	0.84841 (13)	0.27696 (12)	0.0304 (4)
C25	0.33276 (15)	0.73703 (12)	0.27643 (11)	0.0253 (3)
N25	0.39928 (14)	0.69207 (11)	0.35479 (10)	0.0324 (3)
C26	0.31367 (15)	0.67600 (12)	0.19510 (11)	0.0239 (3)
C27	0.24427 (16)	0.72964 (12)	0.11530 (11)	0.0284 (3)
C27a	0.19712 (17)	0.83555 (13)	0.11942 (12)	0.0312 (4)
C28	0.35989 (14)	0.56004 (12)	0.19606 (11)	0.0237 (3)
O28	0.40653 (11)	0.50868 (8)	0.27099 (8)	0.0285 (3)
C29	0.35032 (15)	0.50120 (12)	0.10696 (11)	0.0258 (3)
C210	0.37997 (15)	0.39319 (12)	0.10832 (11)	0.0250 (3)
C211	0.37359 (15)	0.32496 (12)	0.02711 (11)	0.0255 (3)
C212	0.33357 (15)	0.36544 (12)	−0.06698 (12)	0.0268 (3)
C213	0.32193 (16)	0.29851 (13)	−0.14029 (12)	0.0309 (4)
C214	0.35218 (17)	0.18441 (13)	−0.12406 (14)	0.0365 (4)
N241	0.34161 (19)	0.11719 (13)	−0.19717 (14)	0.0573 (5)
C242	0.2858 (2)	0.15843 (17)	−0.28887 (16)	0.0574 (6)
C243	0.3883 (2)	0.00276 (15)	−0.18392 (17)	0.0534 (5)
C215	0.39294 (19)	0.14362 (13)	−0.03017 (14)	0.0405 (4)
C216	0.40253 (18)	0.21184 (13)	0.04283 (13)	0.0342 (4)
H12A	−0.0812	0.6023	0.9344	0.042*
H12B	−0.0279	0.6695	1.0157	0.042*
H14	0.3716	0.5860	0.7803	0.033*
H15A	0.5067	0.7448	0.5614	0.040*
H15B	0.5298	0.6475	0.6375	0.040*
H17	0.0553	0.8858	0.7049	0.032*
H19	0.1011	0.9910	0.5832	0.033*
H110	0.3152	1.0558	0.4232	0.034*
H112	−0.0035	1.1592	0.5767	0.034*
H113	−0.1257	1.3241	0.5442	0.034*
H14A	−0.2763	1.4519	0.4395	0.056*
H14B	−0.2390	1.5775	0.4305	0.056*
H14C	−0.1993	1.4944	0.5240	0.056*
H14D	0.0754	1.5502	0.2858	0.056*
H14E	−0.0728	1.6196	0.3051	0.056*
H14F	−0.0577	1.5162	0.2406	0.056*
H115	0.1523	1.3874	0.2813	0.035*
H116	0.2722	1.2216	0.3151	0.035*
H22A	−0.0159	1.0043	0.1225	0.054*
H22B	0.1114	1.0672	0.0509	0.054*
H24	0.2971	0.8901	0.3299	0.036*
H25A	0.4253	0.6219	0.3574	0.039*
H25B	0.4054	0.7343	0.4026	0.039*
H27	0.2312	0.6915	0.0598	0.034*
H29	0.3225	0.5409	0.0475	0.031*
H210	0.4083	0.3570	0.1691	0.030*
H212	0.3138	0.4419	−0.0805	0.032*
H213	0.2932	0.3292	−0.2027	0.037*
H24A	0.1870	0.1855	−0.2706	0.086*
H24B	0.2903	0.0995	−0.3331	0.086*
H24C	0.3422	0.2183	−0.3253	0.086*
H24D	0.4863	−0.0037	−0.1708	0.080*
H24E	0.3833	−0.0312	−0.2461	0.080*
H24F	0.3269	−0.0344	−0.1258	0.080*
H215	0.4143	0.0674	−0.0167	0.049*
H216	0.4296	0.1813	0.1059	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O11	0.0333 (6)	0.0315 (6)	0.0379 (6)	0.0076 (5)	0.0028 (5)	0.0022 (5)
C12	0.0290 (8)	0.0343 (9)	0.0386 (9)	0.0051 (7)	−0.0045 (7)	0.0024 (7)
O13	0.0296 (6)	0.0312 (6)	0.0332 (6)	0.0042 (5)	−0.0019 (5)	0.0026 (5)
C13a	0.0273 (8)	0.0238 (8)	0.0272 (8)	−0.0015 (6)	−0.0089 (7)	−0.0014 (6)
C14	0.0255 (8)	0.0251 (8)	0.0332 (8)	0.0025 (6)	−0.0099 (7)	−0.0019 (7)
C15	0.0247 (7)	0.0261 (8)	0.0295 (8)	−0.0021 (6)	−0.0090 (7)	−0.0061 (6)
N15	0.0269 (7)	0.0334 (8)	0.0369 (8)	0.0041 (6)	−0.0038 (6)	0.0019 (6)
C16	0.0252 (7)	0.0210 (7)	0.0273 (8)	−0.0011 (6)	−0.0092 (6)	−0.0057 (6)
C17	0.0280 (8)	0.0213 (8)	0.0332 (8)	0.0030 (6)	−0.0095 (7)	−0.0054 (6)
C17a	0.0239 (7)	0.0257 (8)	0.0307 (8)	0.0013 (6)	−0.0052 (7)	−0.0059 (6)
C18	0.0306 (8)	0.0234 (8)	0.0275 (8)	−0.0022 (6)	−0.0107 (7)	−0.0064 (6)
O18	0.0347 (6)	0.0284 (6)	0.0286 (6)	0.0007 (5)	−0.0045 (5)	−0.0046 (5)
C19	0.0288 (8)	0.0257 (8)	0.0297 (8)	−0.0017 (6)	−0.0091 (7)	−0.0042 (6)
C110	0.0310 (8)	0.0273 (8)	0.0281 (8)	−0.0008 (6)	−0.0095 (7)	−0.0059 (6)
C111	0.0298 (8)	0.0225 (8)	0.0300 (8)	−0.0040 (6)	−0.0090 (7)	−0.0040 (6)
C112	0.0326 (8)	0.0252 (8)	0.0279 (8)	−0.0052 (6)	−0.0068 (7)	−0.0003 (6)
C113	0.0283 (8)	0.0279 (8)	0.0290 (8)	−0.0031 (6)	−0.0054 (7)	−0.0048 (6)
C114	0.0276 (8)	0.0232 (8)	0.0318 (8)	−0.0041 (6)	−0.0097 (7)	−0.0020 (6)
N141	0.0322 (7)	0.0243 (7)	0.0382 (8)	0.0003 (5)	−0.0055 (6)	0.0010 (6)
C142	0.0339 (9)	0.0298 (9)	0.0488 (10)	0.0021 (7)	−0.0082 (8)	−0.0032 (8)
C143	0.0408 (10)	0.0281 (9)	0.0426 (10)	−0.0016 (7)	−0.0104 (8)	0.0035 (7)
C115	0.0318 (8)	0.0252 (8)	0.0304 (8)	−0.0067 (6)	−0.0063 (7)	0.0010 (6)
C116	0.0308 (8)	0.0273 (8)	0.0297 (8)	−0.0043 (6)	−0.0063 (7)	−0.0027 (7)
O21	0.0801 (10)	0.0292 (7)	0.0479 (7)	0.0240 (6)	−0.0353 (7)	−0.0126 (6)
C22	0.0637 (12)	0.0303 (10)	0.0448 (10)	0.0160 (8)	−0.0234 (10)	−0.0106 (8)
O23	0.0724 (9)	0.0268 (6)	0.0466 (7)	0.0196 (6)	−0.0289 (7)	−0.0133 (5)
C23a	0.0386 (9)	0.0224 (8)	0.0350 (9)	0.0075 (7)	−0.0083 (8)	−0.0063 (7)
C24	0.0377 (9)	0.0261 (8)	0.0286 (8)	0.0019 (7)	−0.0066 (7)	−0.0090 (6)
C25	0.0247 (7)	0.0254 (8)	0.0247 (8)	0.0015 (6)	−0.0030 (6)	−0.0023 (6)
N25	0.0431 (8)	0.0278 (7)	0.0285 (7)	0.0072 (6)	−0.0121 (6)	−0.0081 (6)
C26	0.0235 (7)	0.0232 (8)	0.0247 (7)	0.0010 (6)	−0.0035 (6)	−0.0036 (6)
C27	0.0346 (8)	0.0250 (8)	0.0269 (8)	0.0025 (6)	−0.0084 (7)	−0.0060 (6)
C27a	0.0383 (9)	0.0255 (8)	0.0307 (8)	0.0067 (7)	−0.0117 (7)	−0.0039 (7)
C28	0.0203 (7)	0.0239 (8)	0.0254 (8)	0.0007 (6)	0.0000 (6)	−0.0024 (6)
O28	0.0322 (6)	0.0256 (6)	0.0279 (6)	0.0041 (4)	−0.0085 (5)	−0.0015 (4)
C29	0.0262 (8)	0.0240 (8)	0.0267 (8)	0.0004 (6)	−0.0040 (6)	−0.0020 (6)
C210	0.0249 (7)	0.0228 (8)	0.0269 (8)	0.0002 (6)	−0.0043 (6)	−0.0015 (6)
C211	0.0235 (7)	0.0221 (8)	0.0305 (8)	0.0011 (6)	−0.0034 (6)	−0.0035 (6)
C212	0.0257 (8)	0.0227 (8)	0.0316 (8)	0.0015 (6)	−0.0039 (7)	−0.0037 (6)
C213	0.0307 (8)	0.0307 (9)	0.0325 (8)	0.0065 (6)	−0.0098 (7)	−0.0070 (7)
C214	0.0358 (9)	0.0301 (9)	0.0490 (10)	0.0060 (7)	−0.0177 (8)	−0.0164 (8)
N241	0.0762 (12)	0.0387 (9)	0.0716 (11)	0.0214 (8)	−0.0473 (10)	−0.0315 (8)
C242	0.0737 (14)	0.0504 (12)	0.0606 (13)	0.0082 (10)	−0.0370 (12)	−0.0275 (10)
C243	0.0627 (13)	0.0340 (10)	0.0730 (14)	0.0085 (9)	−0.0273 (11)	−0.0280 (10)
C215	0.0496 (11)	0.0219 (8)	0.0540 (11)	0.0061 (7)	−0.0203 (9)	−0.0092 (8)
C216	0.0428 (9)	0.0230 (8)	0.0382 (9)	0.0042 (7)	−0.0134 (8)	−0.0030 (7)

Geometric parameters (Å, º)

O11—C17a	1.3838 (18)	O21—C27a	1.3888 (18)
O11—C12	1.4189 (19)	O21—C22	1.426 (2)
C12—O13	1.4399 (18)	C22—O23	1.434 (2)
C12—H12A	0.9900	C22—H22A	0.9900
C12—H12B	0.9900	C22—H22B	0.9900
O13—C13a	1.3723 (18)	O23—C23a	1.3721 (18)
C13a—C14	1.358 (2)	C23a—C24	1.351 (2)
C13a—C17a	1.390 (2)	C23a—C27a	1.393 (2)
C14—C15	1.419 (2)	C24—C25	1.418 (2)
C14—H14	0.9500	C24—H24	0.9500
C15—N15	1.3696 (19)	C25—N25	1.3587 (18)
C15—C16	1.426 (2)	C25—C26	1.431 (2)
N15—H15A	0.8805	N25—H25A	0.8799
N15—H15B	0.8805	N25—H25B	0.8799
C16—C17	1.423 (2)	C26—C27	1.423 (2)
C16—C18	1.473 (2)	C26—C28	1.463 (2)
C17—C17a	1.354 (2)	C27—C27a	1.353 (2)
C17—H17	0.9500	C27—H27	0.9500
C18—O18	1.2529 (18)	C28—O28	1.2503 (16)
C18—C19	1.474 (2)	C28—C29	1.479 (2)
C19—C110	1.341 (2)	C29—C210	1.339 (2)
C19—H19	0.9500	C29—H29	0.9500
C110—C111	1.453 (2)	C210—C211	1.456 (2)
C110—H110	0.9500	C210—H210	0.9500
C111—C112	1.403 (2)	C211—C216	1.400 (2)
C111—C116	1.403 (2)	C211—C212	1.400 (2)
C112—C113	1.377 (2)	C212—C213	1.372 (2)
C112—H112	0.9500	C212—H212	0.9500
C113—C114	1.415 (2)	C213—C214	1.414 (2)
C113—H113	0.9500	C213—H213	0.9500
C114—N141	1.375 (2)	C214—N241	1.370 (2)
C114—C115	1.402 (2)	C214—C215	1.402 (2)
N141—C143	1.447 (2)	N241—C242	1.442 (2)
N141—C142	1.450 (2)	N241—C243	1.448 (2)
C142—H14A	0.9800	C242—H24A	0.9800
C142—H14B	0.9800	C242—H24B	0.9800
C142—H14C	0.9800	C242—H24C	0.9800
C143—H14D	0.9800	C243—H24D	0.9800
C143—H14E	0.9800	C243—H24E	0.9800
C143—H14F	0.9800	C243—H24F	0.9800
C115—C116	1.380 (2)	C215—C216	1.375 (2)
C115—H115	0.9500	C215—H215	0.9500
C116—H116	0.9500	C216—H216	0.9500
C17a—O11—C12	105.70 (12)	C27a—O21—C22	105.18 (12)
O11—C12—O13	108.42 (12)	O21—C22—O23	108.08 (13)
O11—C12—H12A	110.0	O21—C22—H22A	110.1
O13—C12—H12A	110.0	O23—C22—H22A	110.1
O11—C12—H12B	110.0	O21—C22—H22B	110.1
O13—C12—H12B	110.0	O23—C22—H22B	110.1
H12A—C12—H12B	108.4	H22A—C22—H22B	108.4
C13a—O13—C12	105.32 (11)	C23a—O23—C22	105.49 (12)
C14—C13a—O13	127.44 (13)	C24—C23a—O23	127.47 (14)
C14—C13a—C17a	122.64 (14)	C24—C23a—C27a	122.70 (14)
O13—C13a—C17a	109.92 (13)	O23—C23a—C27a	109.80 (13)
C13a—C14—C15	117.67 (13)	C23a—C24—C25	117.76 (14)
C13a—C14—H14	121.2	C23a—C24—H24	121.1
C15—C14—H14	121.2	C25—C24—H24	121.1
N15—C15—C14	116.89 (13)	N25—C25—C24	117.51 (13)
N15—C15—C16	122.78 (13)	N25—C25—C26	122.04 (13)
C14—C15—C16	120.33 (14)	C24—C25—C26	120.45 (13)
C15—N15—H15A	122.3	C25—N25—H25A	118.2
C15—N15—H15B	117.1	C25—N25—H25B	116.8
H15A—N15—H15B	117.9	H25A—N25—H25B	124.7
C15—C16—C17	118.87 (13)	C27—C26—C25	118.47 (13)
C15—C16—C18	120.86 (14)	C27—C26—C28	120.83 (13)
C17—C16—C18	120.27 (13)	C25—C26—C28	120.65 (12)
C17a—C17—C16	118.98 (13)	C27a—C27—C26	119.19 (14)
C17a—C17—H17	120.5	C27a—C27—H27	120.4
C16—C17—H17	120.5	C26—C27—H27	120.4
C17—C17a—O11	129.04 (14)	C27—C27a—O21	129.36 (14)
C17—C17a—C13a	121.50 (14)	C27—C27a—C23a	121.40 (14)
O11—C17a—C13a	109.46 (13)	O21—C27a—C23a	109.20 (13)
O18—C18—C16	121.41 (13)	O28—C28—C26	121.61 (13)
O18—C18—C19	119.10 (13)	O28—C28—C29	118.80 (13)
C16—C18—C19	119.47 (14)	C26—C28—C29	119.59 (12)
C110—C19—C18	122.37 (15)	C210—C29—C28	121.41 (13)
C110—C19—H19	118.8	C210—C29—H29	119.3
C18—C19—H19	118.8	C28—C29—H29	119.3
C19—C110—C111	126.78 (15)	C29—C210—C211	127.26 (13)
C19—C110—H110	116.6	C29—C210—H210	116.4
C111—C110—H110	116.6	C211—C210—H210	116.4
C112—C111—C116	116.10 (14)	C216—C211—C212	116.54 (14)
C112—C111—C110	123.52 (14)	C216—C211—C210	119.89 (13)
C116—C111—C110	120.38 (14)	C212—C211—C210	123.51 (13)
C113—C112—C111	122.27 (14)	C213—C212—C211	122.29 (14)
C113—C112—H112	118.9	C213—C212—H212	118.9
C111—C112—H112	118.9	C211—C212—H212	118.9
C112—C113—C114	121.06 (15)	C212—C213—C214	120.81 (14)
C112—C113—H113	119.5	C212—C213—H213	119.6
C114—C113—H113	119.5	C214—C213—H213	119.6
N141—C114—C115	121.85 (14)	N241—C214—C215	121.80 (15)
N141—C114—C113	121.07 (14)	N241—C214—C213	121.12 (15)
C115—C114—C113	117.07 (14)	C215—C214—C213	117.08 (14)
C114—N141—C143	120.31 (14)	C214—N241—C242	121.17 (15)
C114—N141—C142	120.86 (13)	C214—N241—C243	120.16 (15)
C143—N141—C142	117.10 (13)	C242—N241—C243	118.66 (15)
N141—C142—H14A	109.5	N241—C242—H24A	109.5
N141—C142—H14B	109.5	N241—C242—H24B	109.5
H14A—C142—H14B	109.5	H24A—C242—H24B	109.5
N141—C142—H14C	109.5	N241—C242—H24C	109.5
H14A—C142—H14C	109.5	H24A—C242—H24C	109.5
H14B—C142—H14C	109.5	H24B—C242—H24C	109.5
N141—C143—H14D	109.5	N241—C243—H24D	109.5
N141—C143—H14E	109.5	N241—C243—H24E	109.5
H14D—C143—H14E	109.5	H24D—C243—H24E	109.5
N141—C143—H14F	109.5	N241—C243—H24F	109.5
H14D—C143—H14F	109.5	H24D—C243—H24F	109.5
H14E—C143—H14F	109.5	H24E—C243—H24F	109.5
C116—C115—C114	120.93 (14)	C216—C215—C214	121.27 (15)
C116—C115—H115	119.5	C216—C215—H215	119.4
C114—C115—H115	119.5	C214—C215—H215	119.4
C115—C116—C111	122.56 (15)	C215—C216—C211	122.00 (15)
C115—C116—H116	118.7	C215—C216—H216	119.0
C111—C116—H116	118.7	C211—C216—H216	119.0
C17a—O11—C12—O13	10.49 (16)	C27a—O21—C22—O23	15.0 (2)
O11—C12—O13—C13a	−10.87 (16)	O21—C22—O23—C23a	−14.25 (19)
C12—O13—C13a—C14	−172.57 (15)	C22—O23—C23a—C24	−173.88 (18)
C12—O13—C13a—C17a	7.06 (16)	C22—O23—C23a—C27a	7.96 (19)
O13—C13a—C14—C15	−179.27 (13)	O23—C23a—C24—C25	−179.64 (15)
C17a—C13a—C14—C15	1.1 (2)	C27a—C23a—C24—C25	−1.7 (2)
C13a—C14—C15—N15	−179.51 (13)	C23a—C24—C25—N25	−179.44 (14)
C13a—C14—C15—C16	−0.7 (2)	C23a—C24—C25—C26	1.3 (2)
N15—C15—C16—C17	178.75 (13)	N25—C25—C26—C27	−179.29 (14)
C14—C15—C16—C17	0.0 (2)	C24—C25—C26—C27	0.0 (2)
N15—C15—C16—C18	−0.8 (2)	N25—C25—C26—C28	2.9 (2)
C14—C15—C16—C18	−179.59 (12)	C24—C25—C26—C28	−177.80 (13)
C15—C16—C17—C17a	0.3 (2)	C25—C26—C27—C27a	−0.8 (2)
C18—C16—C17—C17a	179.87 (13)	C28—C26—C27—C27a	176.94 (14)
C16—C17—C17a—O11	−179.73 (13)	C26—C27—C27a—O21	177.74 (16)
C16—C17—C17a—C13a	0.1 (2)	C26—C27—C27a—C23a	0.5 (2)
C12—O11—C17a—C17	173.72 (15)	C22—O21—C27a—C27	172.35 (18)
C12—O11—C17a—C13a	−6.16 (17)	C22—O21—C27a—C23a	−10.1 (2)
C14—C13a—C17a—C17	−0.9 (2)	C24—C23a—C27a—C27	0.9 (3)
O13—C13a—C17a—C17	179.46 (13)	O23—C23a—C27a—C27	179.13 (15)
C14—C13a—C17a—O11	179.00 (13)	C24—C23a—C27a—O21	−176.90 (15)
O13—C13a—C17a—O11	−0.65 (17)	O23—C23a—C27a—O21	1.4 (2)
C15—C16—C18—O18	3.5 (2)	C27—C26—C28—O28	−171.91 (13)
C17—C16—C18—O18	−176.13 (12)	C25—C26—C28—O28	5.8 (2)
C15—C16—C18—C19	−174.87 (13)	C27—C26—C28—C29	7.5 (2)
C17—C16—C18—C19	5.5 (2)	C25—C26—C28—C29	−174.76 (13)
O18—C18—C19—C110	−9.5 (2)	O28—C28—C29—C210	5.2 (2)
C16—C18—C19—C110	168.85 (13)	C26—C28—C29—C210	−174.21 (13)
C18—C19—C110—C111	−174.54 (14)	C28—C29—C210—C211	179.30 (13)
C19—C110—C111—C112	8.8 (2)	C29—C210—C211—C216	−177.31 (15)
C19—C110—C111—C116	−171.81 (14)	C29—C210—C211—C212	−0.1 (2)
C116—C111—C112—C113	0.3 (2)	C216—C211—C212—C213	0.5 (2)
C110—C111—C112—C113	179.75 (14)	C210—C211—C212—C213	−176.81 (14)
C111—C112—C113—C114	−0.6 (2)	C211—C212—C213—C214	−0.9 (2)
C112—C113—C114—N141	−178.03 (13)	C212—C213—C214—N241	−179.60 (16)
C112—C113—C114—C115	0.7 (2)	C212—C213—C214—C215	0.5 (2)
C115—C114—N141—C143	4.4 (2)	C215—C214—N241—C242	173.59 (18)
C113—C114—N141—C143	−176.93 (13)	C213—C214—N241—C242	−6.3 (3)
C115—C114—N141—C142	168.98 (14)	C215—C214—N241—C243	−7.1 (3)
C113—C114—N141—C142	−12.4 (2)	C213—C214—N241—C243	173.01 (17)
N141—C114—C115—C116	178.19 (14)	N241—C214—C215—C216	−179.69 (17)
C113—C114—C115—C116	−0.5 (2)	C213—C214—C215—C216	0.2 (3)
C114—C115—C116—C111	0.3 (2)	C214—C215—C216—C211	−0.6 (3)
C112—C111—C116—C115	−0.1 (2)	C212—C211—C216—C215	0.3 (2)
C110—C111—C116—C115	−179.61 (14)	C210—C211—C216—C215	177.64 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N15—H15A···O18	0.88	2.03	2.6433 (14)	125
N15—H15B···O28^i	0.88	2.26	3.0867 (13)	157
N25—H25A···O28	0.88	1.94	2.6237 (17)	133
N25—H25B···O18	0.88	2.20	3.0606 (17)	165
C14—H14···O28^i	0.95	2.38	3.2067 (18)	145
C24—H24···O18	0.95	2.52	3.3212 (19)	142
C212—H212···O13^ii	0.95	2.60	3.4508 (18)	149

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