Crystal structure of 2-chloro-3-(di-meth-oxy-meth-yl)-6-meth-oxy-quinoline.

The title compound, C13H14ClNO3, crystallizes with Z' = 2 in the space group Pca21, but a search for possible additional crystallographic symmetry found none. However, the crystal structure exhibits pseudosymmetry as the two independent mol-ecules are related by an approximate but non-crystallographic inversion located close to (0.38, 0.26, 1/2) in the selected asymmetric unit, and the structure exhibits partial inversion twinning. The approximate inversion relationship between the two mol-ecules in the selected asymmetric unit is clearly shown by comparison of the relevant torsion angle in the two mol-ecules; the corresponding torsion angles have similar, although not identical magnitudes but with opposite signs. The mean planes of the quinoline rings in the two independent mol-ecules are almost parallel, with a dihedral angle of only 0.16 (3)° between them, and the mutual orientation of these rings permits significant π-π stacking inter-actions between them [centroid-centroid distances = 3.7579 (15) and 3.7923 (15) Å]. In addition, the bimolecular aggregates which are related by translation along [010] are linked by a further π-π stacking inter-action [centroid-centroid distance = 3.7898 (15) Å], so forming a π-stacked chain running parallel to [010]. However, there are no C-H⋯N hydrogen bonds in the structure nor, despite the number of independent aromatic rings, are there any C-H⋯π hydrogen bonds; hence there are no direction-specific inter-actions between adjacent π-stacked chains.

Related literature

For structures of substituted 2-chloro­quinolines, see Insuasty et al. (2006 ▸); Hathwar et al. (2010 ▸); Anuradha et al. (2013a ▸,b ▸).

Experimental

Crystal data

C13H14ClNO3

M = 267.70

Orthorhombic,

a = 27.1156 (9) Å

b = 7.1401 (3) Å

c = 13.0804 (5) Å

V = 2532.47 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.30 mm−1

T = 173 K

0.48 × 0.32 × 0.22 mm

Data collection

Agilent Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012 ▸) T min = 0.808, T max = 0.936

29727 measured reflections

5975 independent reflections

5204 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.097

S = 1.08

5975 reflections

331 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▸) x determined using 1610 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▸)

Absolute structure parameter: 0.43 (3)

Data collection: CrysAlis PRO (Agilent, 2012 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▸); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXL2014 and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S205698901500804X/hg5440sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901500804X/hg5440Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S205698901500804X/hg5440Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S205698901500804X/hg5440fig1.tif

The two independent mol­ecules in the title compound showing the atom-labelling scheme. Displacement ellipsoids are shown at the 30% probability level.

Click here for additional data file.

. DOI: 10.1107/S205698901500804X/hg5440fig2.tif

The two mol­ecules in the selected asymmetric unit, viewed normal to the planes of the quinolone units, showing the ring overlap which leads to a π..π sktacking inter­action. For the sake of clarity, the H atoms have been omitted.

Click here for additional data file.

. DOI: 10.1107/S205698901500804X/hg5440fig3.tif

A stereoview of part of the crystal structure of the title compound showing the formation of a π-stacked chain parallel to [010]. For the sake of clarity, the H atoms have been omitted.

CCDC reference: 1061227

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

C13H14ClNO3	Dx = 1.404 Mg m−3
Mr = 267.70	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 7046 reflections
a = 27.1156 (9) Å	θ = 3.0–32.9°
b = 7.1401 (3) Å	µ = 0.30 mm−1
c = 13.0804 (5) Å	T = 173 K
V = 2532.47 (17) Å3	Block, colourless
Z = 8	0.48 × 0.32 × 0.22 mm
F(000) = 1120

Agilent Eos Gemini diffractometer	5204 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.037
ω scans	θmax = 30.0°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012)	h = −38→38
Tmin = 0.808, Tmax = 0.936	k = −10→10
29727 measured reflections	l = −18→11
5975 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040	w = 1/[σ2(Fo2) + (0.040P)2 + 0.6971P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.097	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.25 e Å−3
5975 reflections	Δρmin = −0.22 e Å−3
331 parameters	Absolute structure: Flack (1983) x determined using 1610 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.43 (3)

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.

	x	y	z	Uiso*/Ueq
N11	0.39039 (8)	0.0376 (3)	0.29016 (19)	0.0292 (5)
C12	0.43758 (10)	0.0736 (4)	0.2853 (2)	0.0288 (6)
Cl12	0.46105 (3)	0.09675 (13)	0.16196 (6)	0.0454 (2)
C13	0.46977 (9)	0.0934 (3)	0.3699 (2)	0.0251 (5)
C14	0.44942 (9)	0.0669 (3)	0.4645 (2)	0.0231 (5)
H14	0.4696	0.0759	0.5237	0.028*
C14A	0.39862 (9)	0.0263 (3)	0.4750 (2)	0.0219 (5)
C15	0.37608 (9)	0.0021 (3)	0.5722 (2)	0.0233 (5)
H15	0.3953	0.0050	0.6330	0.028*
C16	0.32597 (9)	−0.0257 (4)	0.5764 (2)	0.0258 (5)
C17	0.29751 (9)	−0.0318 (4)	0.4865 (3)	0.0319 (6)
H17	0.2629	−0.0496	0.4913	0.038*
C18	0.31884 (10)	−0.0127 (4)	0.3927 (3)	0.0305 (6)
H18	0.2992	−0.0191	0.3326	0.037*
C18A	0.37043 (9)	0.0167 (4)	0.3853 (2)	0.0249 (5)
C13A	0.52323 (9)	0.1523 (4)	0.3548 (2)	0.0281 (5)
H13A	0.5234	0.2665	0.3106	0.034*
O131	0.55262 (7)	0.0153 (3)	0.30701 (18)	0.0321 (5)
C131	0.55388 (11)	−0.1605 (4)	0.3590 (3)	0.0429 (8)
H13B	0.5794	−0.2402	0.3284	0.064*
H13C	0.5217	−0.2221	0.3527	0.064*
H13D	0.5614	−0.1400	0.4314	0.064*
O132	0.54123 (7)	0.2034 (3)	0.45089 (17)	0.0352 (5)
C132	0.58878 (11)	0.2904 (6)	0.4464 (3)	0.0505 (9)
H13E	0.5886	0.3884	0.3939	0.076*
H13F	0.6137	0.1963	0.4292	0.076*
H13G	0.5966	0.3462	0.5129	0.076*
O161	0.29952 (6)	−0.0473 (3)	0.66505 (19)	0.0350 (5)
C161	0.32646 (11)	−0.0603 (4)	0.7579 (2)	0.0359 (6)
H16A	0.3514	−0.1591	0.7520	0.054*
H16B	0.3039	−0.0902	0.8140	0.054*
H16C	0.3427	0.0596	0.7718	0.054*
N21	0.36627 (8)	0.4764 (3)	0.7052 (2)	0.0283 (5)
C22	0.31896 (9)	0.4430 (4)	0.7132 (2)	0.0266 (5)
Cl22	0.29765 (3)	0.42155 (12)	0.83834 (6)	0.04137 (18)
C23	0.28587 (9)	0.4207 (3)	0.6311 (2)	0.0244 (5)
C24	0.30472 (9)	0.4451 (4)	0.5349 (2)	0.0232 (5)
H24	0.2836	0.4347	0.4772	0.028*
C24A	0.35540 (9)	0.4858 (3)	0.5202 (2)	0.0210 (5)
C25	0.37671 (9)	0.5086 (3)	0.4222 (2)	0.0230 (5)
H25	0.3567	0.5039	0.3626	0.028*
C26	0.42667 (9)	0.5376 (4)	0.4143 (2)	0.0248 (5)
C27	0.45641 (9)	0.5448 (4)	0.5036 (3)	0.0284 (6)
H27	0.4910	0.5632	0.4970	0.034*
C28	0.43643 (9)	0.5259 (4)	0.5976 (2)	0.0293 (6)
H28	0.4569	0.5329	0.6564	0.035*
C28A	0.38520 (9)	0.4957 (3)	0.6092 (2)	0.0235 (5)
C23A	0.23260 (9)	0.3619 (4)	0.6500 (2)	0.0272 (5)
H23A	0.2329	0.2542	0.6989	0.033*
O231	0.20304 (7)	0.5042 (3)	0.6925 (2)	0.0374 (5)
C231	0.20056 (11)	0.6697 (4)	0.6326 (3)	0.0458 (9)
H23B	0.1889	0.6385	0.5638	0.069*
H23C	0.2334	0.7264	0.6282	0.069*
H23D	0.1777	0.7584	0.6645	0.069*
O232	0.21399 (6)	0.2972 (3)	0.55662 (16)	0.0311 (4)
C232	0.16713 (11)	0.2090 (5)	0.5660 (3)	0.0424 (8)
H23E	0.1599	0.1387	0.5034	0.064*
H23F	0.1417	0.3044	0.5767	0.064*
H23G	0.1676	0.1231	0.6244	0.064*
O261	0.45217 (6)	0.5572 (3)	0.32579 (18)	0.0332 (4)
C261	0.42426 (10)	0.5695 (4)	0.2333 (3)	0.0359 (7)
H26A	0.4468	0.5846	0.1752	0.054*
H26B	0.4020	0.6775	0.2368	0.054*
H26C	0.4049	0.4548	0.2243	0.054*

	U11	U22	U33	U12	U13	U23
N11	0.0278 (10)	0.0365 (11)	0.0233 (13)	0.0061 (9)	−0.0032 (9)	−0.0022 (10)
C12	0.0317 (12)	0.0341 (14)	0.0206 (14)	0.0088 (10)	0.0021 (11)	0.0011 (11)
Cl12	0.0410 (4)	0.0734 (5)	0.0217 (3)	0.0135 (4)	0.0051 (3)	0.0014 (4)
C13	0.0240 (11)	0.0266 (12)	0.0248 (13)	0.0051 (9)	0.0023 (10)	0.0012 (10)
C14	0.0211 (11)	0.0261 (12)	0.0221 (13)	0.0026 (9)	−0.0004 (9)	0.0015 (10)
C14A	0.0218 (11)	0.0192 (9)	0.0248 (14)	0.0031 (8)	−0.0001 (10)	0.0008 (10)
C15	0.0225 (10)	0.0247 (12)	0.0226 (14)	−0.0012 (9)	−0.0012 (9)	0.0029 (9)
C16	0.0256 (11)	0.0237 (11)	0.0281 (15)	0.0001 (9)	0.0020 (10)	0.0027 (10)
C17	0.0213 (11)	0.0358 (13)	0.0387 (19)	−0.0008 (10)	−0.0035 (11)	0.0006 (13)
C18	0.0251 (11)	0.0368 (14)	0.0295 (16)	0.0033 (10)	−0.0060 (11)	−0.0002 (12)
C18A	0.0240 (11)	0.0254 (12)	0.0255 (15)	0.0050 (9)	−0.0024 (10)	−0.0008 (10)
C13A	0.0265 (11)	0.0343 (12)	0.0235 (14)	0.0002 (10)	0.0065 (10)	0.0029 (11)
O131	0.0277 (8)	0.0383 (11)	0.0302 (13)	0.0026 (7)	0.0101 (8)	−0.0003 (8)
C131	0.0310 (14)	0.0372 (15)	0.061 (2)	0.0050 (12)	0.0101 (14)	0.0021 (15)
O132	0.0266 (9)	0.0515 (12)	0.0276 (11)	−0.0055 (8)	0.0059 (8)	−0.0048 (9)
C132	0.0339 (15)	0.072 (2)	0.046 (2)	−0.0184 (15)	0.0083 (14)	−0.0148 (18)
O161	0.0236 (8)	0.0496 (11)	0.0318 (13)	−0.0054 (8)	0.0028 (8)	0.0062 (11)
C161	0.0329 (14)	0.0461 (16)	0.0286 (16)	−0.0009 (12)	0.0025 (12)	0.0056 (13)
N21	0.0260 (10)	0.0350 (12)	0.0237 (12)	0.0051 (9)	−0.0022 (9)	−0.0026 (10)
C22	0.0287 (12)	0.0329 (13)	0.0181 (13)	0.0054 (10)	0.0008 (10)	0.0005 (10)
Cl22	0.0379 (3)	0.0660 (5)	0.0201 (3)	0.0034 (3)	0.0030 (3)	0.0008 (4)
C23	0.0248 (11)	0.0255 (11)	0.0227 (13)	0.0003 (9)	0.0008 (10)	−0.0002 (9)
C24	0.0216 (10)	0.0261 (11)	0.0219 (13)	0.0007 (9)	−0.0029 (10)	0.0014 (10)
C24A	0.0224 (10)	0.0175 (10)	0.0231 (13)	0.0016 (8)	−0.0003 (10)	−0.0010 (9)
C25	0.0227 (11)	0.0233 (12)	0.0230 (14)	−0.0014 (8)	−0.0013 (10)	0.0017 (9)
C26	0.0236 (11)	0.0232 (11)	0.0277 (15)	−0.0008 (9)	0.0007 (10)	0.0017 (11)
C27	0.0204 (10)	0.0311 (12)	0.0337 (16)	−0.0019 (9)	−0.0024 (10)	−0.0015 (12)
C28	0.0220 (11)	0.0349 (13)	0.0310 (16)	−0.0011 (10)	−0.0059 (11)	−0.0043 (12)
C28A	0.0238 (11)	0.0237 (11)	0.0231 (14)	0.0037 (9)	−0.0029 (10)	−0.0030 (10)
C23A	0.0261 (11)	0.0340 (12)	0.0214 (13)	−0.0018 (9)	0.0021 (10)	0.0036 (11)
O231	0.0294 (9)	0.0439 (12)	0.0387 (14)	0.0014 (8)	0.0089 (9)	−0.0039 (10)
C231	0.0265 (13)	0.0388 (15)	0.072 (3)	0.0013 (11)	0.0056 (15)	0.0013 (16)
O232	0.0241 (8)	0.0432 (11)	0.0260 (11)	−0.0084 (8)	0.0022 (7)	0.0010 (8)
C232	0.0353 (15)	0.0542 (18)	0.0378 (18)	−0.0194 (13)	0.0039 (13)	−0.0012 (14)
O261	0.0236 (8)	0.0471 (11)	0.0288 (12)	−0.0042 (8)	0.0034 (8)	0.0046 (10)
C261	0.0320 (14)	0.0484 (17)	0.0275 (16)	0.0008 (12)	0.0011 (11)	0.0028 (14)

N11—C12	1.307 (3)	N21—C22	1.309 (3)
N11—C18A	1.365 (4)	N21—C28A	1.363 (4)
C12—C13	1.417 (4)	C22—C23	1.408 (4)
C12—Cl12	1.742 (3)	C22—Cl22	1.743 (3)
C13—C14	1.368 (4)	C23—C24	1.370 (4)
C13—C13A	1.522 (3)	C23—C23A	1.524 (3)
C14—C14A	1.414 (3)	C24—C24A	1.417 (3)
C14—H14	0.9500	C24—H24	0.9500
C14A—C18A	1.402 (4)	C24A—C25	1.416 (4)
C14A—C15	1.422 (4)	C24A—C28A	1.419 (4)
C15—C16	1.374 (3)	C25—C26	1.374 (3)
C15—H15	0.9500	C25—H25	0.9500
C16—O161	1.372 (4)	C26—O261	1.355 (3)
C16—C17	1.407 (4)	C26—C27	1.420 (4)
C17—C18	1.364 (5)	C27—C28	1.351 (4)
C17—H17	0.9500	C27—H27	0.9500
C18—C18A	1.418 (3)	C28—C28A	1.414 (3)
C18—H18	0.9500	C28—H28	0.9500
C13A—O132	1.396 (3)	C23A—O232	1.400 (3)
C13A—O131	1.408 (3)	C23A—O231	1.408 (3)
C13A—H13A	1.0000	C23A—H23A	1.0000
O131—C131	1.428 (4)	O231—C231	1.419 (4)
C131—H13B	0.9800	C231—H23B	0.9800
C131—H13C	0.9800	C231—H23C	0.9800
C131—H13D	0.9800	C231—H23D	0.9800
O132—C132	1.433 (3)	O232—C232	1.424 (3)
C132—H13E	0.9800	C232—H23E	0.9800
C132—H13F	0.9800	C232—H23F	0.9800
C132—H13G	0.9800	C232—H23G	0.9800
O161—C161	1.420 (4)	O261—C261	1.430 (4)
C161—H16A	0.9800	C261—H26A	0.9800
C161—H16B	0.9800	C261—H26B	0.9800
C161—H16C	0.9800	C261—H26C	0.9800
C12—N11—C18A	117.0 (2)	C22—N21—C28A	117.4 (2)
N11—C12—C13	125.8 (3)	N21—C22—C23	125.7 (3)
N11—C12—Cl12	114.9 (2)	N21—C22—Cl22	114.6 (2)
C13—C12—Cl12	119.3 (2)	C23—C22—Cl22	119.7 (2)
C14—C13—C12	116.4 (2)	C24—C23—C22	116.6 (2)
C14—C13—C13A	122.7 (2)	C24—C23—C23A	122.5 (2)
C12—C13—C13A	120.9 (3)	C22—C23—C23A	120.7 (2)
C13—C14—C14A	120.6 (2)	C23—C24—C24A	120.8 (2)
C13—C14—H14	119.7	C23—C24—H24	119.6
C14A—C14—H14	119.7	C24A—C24—H24	119.6
C18A—C14A—C14	117.4 (3)	C25—C24A—C24	122.8 (2)
C18A—C14A—C15	120.5 (2)	C25—C24A—C28A	120.3 (2)
C14—C14A—C15	122.0 (2)	C24—C24A—C28A	116.8 (3)
C16—C15—C14A	118.6 (3)	C26—C25—C24A	119.2 (3)
C16—C15—H15	120.7	C26—C25—H25	120.4
C14A—C15—H15	120.7	C24A—C25—H25	120.4
O161—C16—C15	124.5 (3)	O261—C26—C25	125.6 (3)
O161—C16—C17	114.6 (2)	O261—C26—C27	114.1 (2)
C15—C16—C17	120.9 (3)	C25—C26—C27	120.2 (3)
C18—C17—C16	121.1 (2)	C28—C27—C26	121.2 (2)
C18—C17—H17	119.5	C28—C27—H27	119.4
C16—C17—H17	119.5	C26—C27—H27	119.4
C17—C18—C18A	119.7 (3)	C27—C28—C28A	120.4 (3)
C17—C18—H18	120.2	C27—C28—H28	119.8
C18A—C18—H18	120.2	C28A—C28—H28	119.8
N11—C18A—C14A	122.8 (2)	N21—C28A—C28	118.9 (2)
N11—C18A—C18	118.0 (3)	N21—C28A—C24A	122.4 (2)
C14A—C18A—C18	119.2 (3)	C28—C28A—C24A	118.6 (3)
O132—C13A—O131	112.5 (2)	O232—C23A—O231	112.2 (2)
O132—C13A—C13	106.8 (2)	O232—C23A—C23	106.9 (2)
O131—C13A—C13	113.9 (2)	O231—C23A—C23	113.9 (2)
O132—C13A—H13A	107.8	O232—C23A—H23A	107.9
O131—C13A—H13A	107.8	O231—C23A—H23A	107.9
C13—C13A—H13A	107.8	C23—C23A—H23A	107.9
C13A—O131—C131	114.4 (2)	C23A—O231—C231	114.2 (3)
O131—C131—H13B	109.5	O231—C231—H23B	109.5
O131—C131—H13C	109.5	O231—C231—H23C	109.5
H13B—C131—H13C	109.5	H23B—C231—H23C	109.5
O131—C131—H13D	109.5	O231—C231—H23D	109.5
H13B—C131—H13D	109.5	H23B—C231—H23D	109.5
H13C—C131—H13D	109.5	H23C—C231—H23D	109.5
C13A—O132—C132	113.0 (2)	C23A—O232—C232	113.1 (2)
O132—C132—H13E	109.5	O232—C232—H23E	109.5
O132—C132—H13F	109.5	O232—C232—H23F	109.5
H13E—C132—H13F	109.5	H23E—C232—H23F	109.5
O132—C132—H13G	109.5	O232—C232—H23G	109.5
H13E—C132—H13G	109.5	H23E—C232—H23G	109.5
H13F—C132—H13G	109.5	H23F—C232—H23G	109.5
C16—O161—C161	117.47 (19)	C26—O261—C261	117.32 (19)
O161—C161—H16A	109.5	O261—C261—H26A	109.5
O161—C161—H16B	109.5	O261—C261—H26B	109.5
H16A—C161—H16B	109.5	H26A—C261—H26B	109.5
O161—C161—H16C	109.5	O261—C261—H26C	109.5
H16A—C161—H16C	109.5	H26A—C261—H26C	109.5
H16B—C161—H16C	109.5	H26B—C261—H26C	109.5
C18A—N11—C12—C13	−0.3 (4)	C28A—N21—C22—C23	1.6 (4)
C18A—N11—C12—Cl12	179.47 (19)	C28A—N21—C22—Cl22	−179.65 (19)
N11—C12—C13—C14	2.0 (4)	N21—C22—C23—C24	−3.3 (4)
Cl12—C12—C13—C14	−177.72 (19)	Cl22—C22—C23—C24	178.01 (19)
N11—C12—C13—C13A	−174.6 (3)	N21—C22—C23—C23A	173.5 (3)
Cl12—C12—C13—C13A	5.7 (3)	Cl22—C22—C23—C23A	−5.2 (3)
C12—C13—C14—C14A	−1.4 (3)	C22—C23—C24—C24A	1.6 (4)
C13A—C13—C14—C14A	175.1 (2)	C23A—C23—C24—C24A	−175.1 (2)
C13—C14—C14A—C18A	−0.7 (3)	C23—C24—C24A—C25	178.7 (2)
C13—C14—C14A—C15	−178.6 (2)	C23—C24—C24A—C28A	1.3 (4)
C18A—C14A—C15—C16	−1.8 (4)	C24—C24A—C25—C26	−176.4 (2)
C14—C14A—C15—C16	176.1 (2)	C28A—C24A—C25—C26	1.0 (3)
C14A—C15—C16—O161	−178.7 (2)	C24A—C25—C26—O261	178.4 (2)
C14A—C15—C16—C17	0.6 (4)	C24A—C25—C26—C27	−0.1 (4)
O161—C16—C17—C18	−179.9 (3)	O261—C26—C27—C28	−179.5 (3)
C15—C16—C17—C18	0.8 (4)	C25—C26—C27—C28	−0.8 (4)
C16—C17—C18—C18A	−1.0 (4)	C26—C27—C28—C28A	0.9 (4)
C12—N11—C18A—C14A	−2.1 (4)	C22—N21—C28A—C28	−178.0 (2)
C12—N11—C18A—C18	176.8 (2)	C22—N21—C28A—C24A	1.7 (4)
C14—C14A—C18A—N11	2.6 (4)	C27—C28—C28A—N21	179.7 (3)
C15—C14A—C18A—N11	−179.5 (2)	C27—C28—C28A—C24A	0.0 (4)
C14—C14A—C18A—C18	−176.3 (2)	C25—C24A—C28A—N21	179.4 (2)
C15—C14A—C18A—C18	1.6 (4)	C24—C24A—C28A—N21	−3.1 (3)
C17—C18—C18A—N11	−179.2 (3)	C25—C24A—C28A—C28	−0.9 (3)
C17—C18—C18A—C14A	−0.2 (4)	C24—C24A—C28A—C28	176.6 (2)
C14—C13—C13A—O132	−10.6 (3)	C24—C23—C23A—O232	14.3 (3)
C12—C13—C13A—O131	−69.4 (3)	C22—C23—C23A—O231	73.3 (3)
C12—C13—C13A—O132	165.7 (2)	C22—C23—C23A—O232	−162.3 (2)
C14—C13—C13A—O131	114.2 (3)	C24—C23—C23A—O231	−110.1 (3)
O132—C13A—O131—C131	64.3 (3)	O232—C23A—O231—C231	−63.4 (3)
C13—C13A—O131—C131	−57.4 (3)	C23—C23A—O231—C231	58.2 (3)
O131—C13A—O132—C132	63.7 (3)	O231—C23A—O232—C232	−64.2 (3)
C13—C13A—O132—C132	−170.6 (2)	C23—C23A—O232—C232	170.3 (2)
C15—C16—O161—C161	−6.5 (4)	C25—C26—O261—C261	7.3 (4)
C17—C16—O161—C161	174.2 (3)	C27—C26—O261—C261	−174.2 (2)

Table 1

Selected torsion angles ()

C12C13C13AO131	69.4(3)
C12C13C13AO132	165.7(2)
C13C13AO131C131	57.4(3)
C13C13AO132C132	170.6(2)
C22C23C23AO231	73.3(3)
C22C23C23AO232	162.3(2)
C23C23AO231C231	58.2(3)
C23C23AO232C232	170.3(2)