4-Methyl-phenyl quinoline-2-carboxyl-ate.

In the title compound, C(17)H(13)NO(2), two mol-ecules crystallize in the asymmetric unit. The dihedral angle between the mean planes of the quinoline and benzene rings are 78.3 (4) and 88.2 (3)°. The carboxyl-ate group is twisted slightly from the quinoline ring by 7.1 (2) and 13.3 (4)°, respectively. In the crystal, weak C-H⋯O inter-actions are observed. Further stabilization is provided by weak π-π stacking inter-actions, with centroid-centroid distances of 3.564 (9)/3.689 (2) and 3.830 (1)/3.896 (5)Å, respectively.

Related literature

For heterocycles in natural products, see: Morimoto et al. (1991 ▶); Michael (1997 ▶). For heterocycles in fragrances and dyes, see: Padwa et al. (1999 ▶). For heterocycles in biologically active compounds, see: Markees et al. (1970 ▶); Campbell et al. (1988 ▶). For quinoline alkaloids used as efficient drugs for the treatment of malaria, see: Robert & Meunier, (1998 ▶). For quinoline as a privileged scaffold in cancer drug discovery, see: Solomon & Lee (2011 ▶). For related structures, see: Dobrzyńska & Jerzykiewicz, (2004 ▶); Butcher et al. (2007 ▶); Jing & Qin (2008 ▶); Jasinski et al. (2010 ▶). For bond lengths, see Allen et al. (1987 ▶).

Experimental

Crystal data

C17H13NO2

M = 263.28

Orthorhombic,

a = 11.5421 (2) Å

b = 17.3191 (3) Å

c = 26.6667 (5) Å

V = 5330.65 (16) Å3

Z = 16

Cu Kα radiation

μ = 0.70 mm−1

T = 173 K

0.22 × 0.14 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.726, T max = 1.000

34626 measured reflections

5265 independent reflections

4303 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.124

S = 1.02

5265 reflections

363 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Bruker, 2000 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812044030/bq2377sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044030/bq2377Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812044030/bq2377Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H13NO2	F(000) = 2208
Mr = 263.28	Dx = 1.312 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 10490 reflections
a = 11.5421 (2) Å	θ = 3.8–72.7°
b = 17.3191 (3) Å	µ = 0.70 mm−1
c = 26.6667 (5) Å	T = 173 K
V = 5330.65 (16) Å3	Chunk, colorless
Z = 16	0.22 × 0.14 × 0.12 mm

Oxford Diffraction Xcalibur (Eos, Gemini) diffractometer	5265 independent reflections
Radiation source: Enhance (Cu) X-ray Source	4303 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
Detector resolution: 16.0416 pixels mm-1	θmax = 72.8°, θmin = 4.9°
ω scans	h = −14→10
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Oxford Diffraction, 2010)	k = −20→21
Tmin = 0.726, Tmax = 1.000	l = −32→31
34626 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0604P)2 + 1.783P] where P = (Fo2 + 2Fc2)/3
5265 reflections	(Δ/σ)max = 0.001
363 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1A	0.12216 (11)	0.67251 (7)	0.39057 (4)	0.0511 (3)
O2A	0.13223 (13)	0.56857 (9)	0.34041 (5)	0.0657 (4)
N1A	−0.03742 (11)	0.60902 (8)	0.44686 (5)	0.0390 (3)
C1A	−0.11347 (13)	0.57558 (9)	0.47931 (6)	0.0396 (4)
C2A	−0.14961 (14)	0.61816 (10)	0.52172 (6)	0.0450 (4)
H2A	−0.1244	0.6688	0.5259	0.054*
C3A	−0.22121 (15)	0.58568 (11)	0.55662 (7)	0.0525 (4)
H3A	−0.2437	0.6142	0.5845	0.063*
C4A	−0.26120 (16)	0.50963 (12)	0.55081 (8)	0.0578 (5)
H4A	−0.3097	0.4880	0.5749	0.069*
C5A	−0.22915 (15)	0.46757 (11)	0.51017 (8)	0.0569 (5)
H5A	−0.2561	0.4172	0.5067	0.068*
C6A	−0.15524 (14)	0.49894 (9)	0.47282 (7)	0.0464 (4)
C7A	−0.11881 (16)	0.45862 (10)	0.43001 (8)	0.0537 (5)
H7A	−0.1462	0.4090	0.4238	0.064*
C8A	−0.04317 (17)	0.49246 (10)	0.39768 (7)	0.0526 (5)
H8A	−0.0185	0.4664	0.3691	0.063*
C9A	−0.00251 (14)	0.56800 (9)	0.40816 (6)	0.0422 (4)
C10A	0.08924 (16)	0.60161 (10)	0.37521 (6)	0.0455 (4)
C11A	0.21459 (15)	0.70870 (10)	0.36529 (6)	0.0447 (4)
C12A	0.32213 (17)	0.70819 (12)	0.38707 (7)	0.0555 (5)
H12A	0.3348	0.6815	0.4168	0.067*
C13A	0.41123 (16)	0.74779 (11)	0.36423 (7)	0.0534 (4)
H13A	0.4842	0.7475	0.3790	0.064*
C14A	0.39551 (15)	0.78789 (10)	0.32009 (6)	0.0452 (4)
C15A	0.28520 (17)	0.78769 (12)	0.29953 (7)	0.0553 (5)
H15A	0.2719	0.8147	0.2699	0.066*
C16A	0.19469 (16)	0.74867 (12)	0.32171 (7)	0.0535 (5)
H16A	0.1212	0.7494	0.3074	0.064*
C17A	0.49506 (18)	0.82914 (13)	0.29514 (7)	0.0600 (5)
H17D	0.5132	0.8040	0.2640	0.090*
H17E	0.5616	0.8278	0.3167	0.090*
H17F	0.4738	0.8818	0.2888	0.090*
O1B	0.66824 (11)	0.35457 (6)	0.36695 (4)	0.0466 (3)
O2B	0.60648 (11)	0.25607 (7)	0.31907 (5)	0.0540 (3)
N1B	0.78323 (10)	0.26045 (7)	0.42615 (4)	0.0322 (3)
C1B	0.85486 (12)	0.21554 (8)	0.45442 (5)	0.0309 (3)
C2B	0.90207 (13)	0.24698 (9)	0.49877 (6)	0.0365 (3)
H2B	0.8820	0.2968	0.5085	0.044*
C3B	0.97676 (14)	0.20498 (9)	0.52742 (6)	0.0396 (3)
H3B	1.0079	0.2265	0.5564	0.048*
C4B	1.00717 (14)	0.12907 (9)	0.51339 (6)	0.0409 (4)
H4B	1.0576	0.1007	0.5334	0.049*
C5B	0.96322 (14)	0.09699 (9)	0.47076 (6)	0.0392 (4)
H5B	0.9842	0.0470	0.4618	0.047*
C6B	0.88617 (13)	0.13903 (8)	0.44012 (5)	0.0330 (3)
C7B	0.83864 (14)	0.11000 (9)	0.39521 (6)	0.0385 (3)
H7B	0.8567	0.0603	0.3846	0.046*
C8B	0.76635 (14)	0.15486 (9)	0.36753 (6)	0.0385 (3)
H8B	0.7338	0.1363	0.3380	0.046*
C9B	0.74165 (12)	0.23042 (8)	0.38463 (5)	0.0332 (3)
C10B	0.66380 (13)	0.27980 (9)	0.35296 (5)	0.0362 (3)
C11B	0.60426 (15)	0.40810 (9)	0.33826 (6)	0.0396 (4)
C12B	0.48842 (16)	0.41864 (10)	0.34708 (6)	0.0481 (4)
H12B	0.4496	0.3877	0.3701	0.058*
C13B	0.42981 (16)	0.47621 (11)	0.32107 (6)	0.0488 (4)
H13B	0.3511	0.4835	0.3269	0.059*
C14B	0.48616 (15)	0.52276 (9)	0.28679 (6)	0.0428 (4)
C15B	0.60316 (15)	0.51005 (10)	0.27840 (6)	0.0428 (4)
H15B	0.6422	0.5403	0.2551	0.051*
C16B	0.66314 (15)	0.45307 (9)	0.30413 (6)	0.0416 (4)
H16B	0.7418	0.4454	0.2984	0.050*
C17B	0.42202 (19)	0.58559 (11)	0.25908 (8)	0.0597 (5)
H17A	0.4712	0.6300	0.2558	0.089*
H17B	0.3536	0.5994	0.2775	0.089*
H17C	0.4005	0.5673	0.2264	0.089*

	U11	U22	U33	U12	U13	U23
O1A	0.0630 (8)	0.0459 (7)	0.0443 (6)	−0.0036 (6)	0.0113 (6)	−0.0089 (5)
O2A	0.0815 (10)	0.0666 (9)	0.0489 (7)	0.0005 (8)	0.0093 (7)	−0.0219 (6)
N1A	0.0399 (7)	0.0362 (7)	0.0408 (7)	0.0000 (5)	−0.0069 (6)	−0.0042 (5)
C1A	0.0340 (8)	0.0357 (8)	0.0491 (9)	0.0000 (6)	−0.0108 (7)	0.0032 (7)
C2A	0.0400 (9)	0.0456 (9)	0.0493 (9)	−0.0030 (7)	−0.0047 (7)	−0.0009 (7)
C3A	0.0397 (9)	0.0626 (12)	0.0552 (10)	0.0000 (8)	−0.0009 (8)	0.0061 (9)
C4A	0.0396 (9)	0.0603 (12)	0.0735 (13)	0.0004 (8)	−0.0007 (9)	0.0205 (10)
C5A	0.0391 (9)	0.0409 (9)	0.0908 (15)	−0.0038 (7)	−0.0120 (9)	0.0193 (10)
C6A	0.0384 (8)	0.0339 (8)	0.0670 (11)	0.0023 (7)	−0.0151 (8)	0.0030 (8)
C7A	0.0485 (10)	0.0333 (8)	0.0793 (13)	−0.0010 (7)	−0.0175 (9)	−0.0060 (8)
C8A	0.0572 (11)	0.0427 (9)	0.0580 (11)	0.0080 (8)	−0.0130 (9)	−0.0156 (8)
C9A	0.0438 (9)	0.0388 (8)	0.0439 (8)	0.0053 (7)	−0.0119 (7)	−0.0067 (7)
C10A	0.0544 (10)	0.0463 (9)	0.0357 (8)	0.0079 (8)	−0.0076 (7)	−0.0088 (7)
C11A	0.0535 (10)	0.0437 (9)	0.0368 (8)	0.0051 (8)	0.0066 (7)	−0.0038 (7)
C12A	0.0650 (12)	0.0597 (11)	0.0418 (9)	0.0046 (9)	−0.0070 (9)	0.0130 (8)
C13A	0.0509 (10)	0.0619 (11)	0.0475 (10)	0.0043 (9)	−0.0101 (8)	0.0077 (8)
C14A	0.0526 (10)	0.0464 (9)	0.0366 (8)	0.0057 (8)	0.0002 (7)	−0.0019 (7)
C15A	0.0584 (11)	0.0684 (12)	0.0390 (9)	0.0069 (9)	−0.0039 (8)	0.0129 (8)
C16A	0.0452 (9)	0.0704 (12)	0.0447 (9)	0.0062 (9)	−0.0045 (8)	0.0059 (9)
C17A	0.0640 (12)	0.0682 (13)	0.0477 (10)	−0.0078 (10)	0.0010 (9)	0.0003 (9)
O1B	0.0612 (7)	0.0323 (6)	0.0463 (6)	0.0021 (5)	−0.0194 (5)	−0.0004 (5)
O2B	0.0662 (8)	0.0464 (7)	0.0494 (7)	0.0073 (6)	−0.0224 (6)	−0.0120 (5)
N1B	0.0362 (6)	0.0270 (6)	0.0333 (6)	−0.0016 (5)	0.0012 (5)	−0.0006 (5)
C1B	0.0337 (7)	0.0259 (7)	0.0330 (7)	−0.0026 (6)	0.0037 (6)	0.0012 (5)
C2B	0.0435 (8)	0.0283 (7)	0.0378 (8)	−0.0004 (6)	−0.0009 (6)	−0.0010 (6)
C3B	0.0460 (9)	0.0366 (8)	0.0363 (8)	−0.0016 (7)	−0.0036 (7)	0.0017 (6)
C4B	0.0433 (9)	0.0379 (8)	0.0417 (8)	0.0057 (7)	−0.0005 (7)	0.0083 (7)
C5B	0.0466 (9)	0.0270 (7)	0.0441 (8)	0.0049 (6)	0.0069 (7)	0.0036 (6)
C6B	0.0371 (8)	0.0267 (7)	0.0351 (7)	−0.0019 (6)	0.0083 (6)	0.0007 (5)
C7B	0.0488 (9)	0.0265 (7)	0.0400 (8)	0.0000 (6)	0.0061 (7)	−0.0051 (6)
C8B	0.0467 (9)	0.0343 (8)	0.0343 (7)	−0.0045 (7)	0.0007 (6)	−0.0068 (6)
C9B	0.0346 (7)	0.0318 (7)	0.0332 (7)	−0.0036 (6)	0.0020 (6)	−0.0009 (6)
C10B	0.0385 (8)	0.0367 (8)	0.0335 (7)	−0.0013 (6)	0.0014 (6)	−0.0026 (6)
C11B	0.0514 (9)	0.0332 (8)	0.0341 (8)	0.0026 (7)	−0.0108 (7)	−0.0023 (6)
C12B	0.0519 (10)	0.0484 (10)	0.0440 (9)	−0.0026 (8)	0.0000 (8)	0.0086 (7)
C13B	0.0458 (9)	0.0545 (10)	0.0462 (9)	0.0072 (8)	−0.0011 (8)	0.0022 (8)
C14B	0.0528 (10)	0.0387 (8)	0.0369 (8)	0.0061 (7)	−0.0073 (7)	−0.0029 (6)
C15B	0.0533 (10)	0.0414 (9)	0.0337 (8)	−0.0005 (7)	−0.0022 (7)	0.0030 (6)
C16B	0.0444 (9)	0.0426 (9)	0.0378 (8)	0.0034 (7)	−0.0022 (7)	−0.0044 (7)
C17B	0.0685 (12)	0.0532 (11)	0.0573 (11)	0.0158 (9)	−0.0089 (10)	0.0076 (9)

O1A—C10A	1.349 (2)	O1B—C10B	1.3486 (18)
O1A—C11A	1.409 (2)	O1B—C11B	1.4108 (18)
O2A—C10A	1.198 (2)	O2B—C10B	1.1930 (18)
N1A—C9A	1.316 (2)	N1B—C9B	1.3139 (18)
N1A—C1A	1.362 (2)	N1B—C1B	1.3626 (18)
C1A—C2A	1.413 (2)	C1B—C2B	1.412 (2)
C1A—C6A	1.423 (2)	C1B—C6B	1.4254 (19)
C2A—C3A	1.366 (2)	C2B—C3B	1.362 (2)
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—C4A	1.404 (3)	C3B—C4B	1.411 (2)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.357 (3)	C4B—C5B	1.363 (2)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—C6A	1.419 (3)	C5B—C6B	1.410 (2)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C7A	1.403 (3)	C6B—C7B	1.410 (2)
C7A—C8A	1.360 (3)	C7B—C8B	1.358 (2)
C7A—H7A	0.9300	C7B—H7B	0.9300
C8A—C9A	1.418 (2)	C8B—C9B	1.415 (2)
C8A—H8A	0.9300	C8B—H8B	0.9300
C9A—C10A	1.494 (3)	C9B—C10B	1.501 (2)
C11A—C12A	1.370 (2)	C11B—C12B	1.370 (2)
C11A—C16A	1.372 (2)	C11B—C16B	1.377 (2)
C12A—C13A	1.378 (3)	C12B—C13B	1.390 (2)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.379 (2)	C13B—C14B	1.382 (2)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—C15A	1.386 (2)	C14B—C15B	1.386 (2)
C14A—C17A	1.508 (3)	C14B—C17B	1.509 (2)
C15A—C16A	1.378 (3)	C15B—C16B	1.387 (2)
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—H16A	0.9300	C16B—H16B	0.9300
C17A—H17D	0.9600	C17B—H17A	0.9600
C17A—H17E	0.9600	C17B—H17B	0.9600
C17A—H17F	0.9600	C17B—H17C	0.9600
C10A—O1A—C11A	118.21 (13)	C10B—O1B—C11B	117.46 (12)
C9A—N1A—C1A	117.78 (14)	C9B—N1B—C1B	117.50 (12)
N1A—C1A—C2A	118.48 (14)	N1B—C1B—C2B	118.52 (12)
N1A—C1A—C6A	122.53 (16)	N1B—C1B—C6B	122.45 (13)
C2A—C1A—C6A	118.96 (16)	C2B—C1B—C6B	119.01 (13)
C3A—C2A—C1A	120.60 (17)	C3B—C2B—C1B	120.54 (14)
C3A—C2A—H2A	119.7	C3B—C2B—H2B	119.7
C1A—C2A—H2A	119.7	C1B—C2B—H2B	119.7
C2A—C3A—C4A	120.66 (19)	C2B—C3B—C4B	120.41 (15)
C2A—C3A—H3A	119.7	C2B—C3B—H3B	119.8
C4A—C3A—H3A	119.7	C4B—C3B—H3B	119.8
C5A—C4A—C3A	120.14 (18)	C5B—C4B—C3B	120.54 (15)
C5A—C4A—H4A	119.9	C5B—C4B—H4B	119.7
C3A—C4A—H4A	119.9	C3B—C4B—H4B	119.7
C4A—C5A—C6A	121.24 (17)	C4B—C5B—C6B	120.49 (14)
C4A—C5A—H5A	119.4	C4B—C5B—H5B	119.8
C6A—C5A—H5A	119.4	C6B—C5B—H5B	119.8
C7A—C6A—C5A	124.10 (17)	C7B—C6B—C5B	123.60 (14)
C7A—C6A—C1A	117.51 (17)	C7B—C6B—C1B	117.39 (14)
C5A—C6A—C1A	118.38 (17)	C5B—C6B—C1B	119.00 (14)
C8A—C7A—C6A	119.59 (16)	C8B—C7B—C6B	119.78 (14)
C8A—C7A—H7A	120.2	C8B—C7B—H7B	120.1
C6A—C7A—H7A	120.2	C6B—C7B—H7B	120.1
C7A—C8A—C9A	119.04 (17)	C7B—C8B—C9B	118.53 (14)
C7A—C8A—H8A	120.5	C7B—C8B—H8B	120.7
C9A—C8A—H8A	120.5	C9B—C8B—H8B	120.7
N1A—C9A—C8A	123.46 (17)	N1B—C9B—C8B	124.34 (14)
N1A—C9A—C10A	117.90 (14)	N1B—C9B—C10B	117.87 (13)
C8A—C9A—C10A	118.56 (15)	C8B—C9B—C10B	117.79 (13)
O2A—C10A—O1A	123.60 (18)	O2B—C10B—O1B	124.15 (14)
O2A—C10A—C9A	124.28 (17)	O2B—C10B—C9B	124.21 (14)
O1A—C10A—C9A	112.06 (14)	O1B—C10B—C9B	111.63 (12)
C12A—C11A—C16A	120.93 (17)	C12B—C11B—C16B	121.32 (15)
C12A—C11A—O1A	118.69 (15)	C12B—C11B—O1B	120.35 (15)
C16A—C11A—O1A	120.19 (16)	C16B—C11B—O1B	118.14 (15)
C11A—C12A—C13A	119.03 (16)	C11B—C12B—C13B	119.00 (16)
C11A—C12A—H12A	120.5	C11B—C12B—H12B	120.5
C13A—C12A—H12A	120.5	C13B—C12B—H12B	120.5
C12A—C13A—C14A	122.00 (17)	C14B—C13B—C12B	121.30 (17)
C12A—C13A—H13A	119.0	C14B—C13B—H13B	119.4
C14A—C13A—H13A	119.0	C12B—C13B—H13B	119.4
C13A—C14A—C15A	117.20 (17)	C13B—C14B—C15B	118.22 (15)
C13A—C14A—C17A	121.00 (16)	C13B—C14B—C17B	120.91 (17)
C15A—C14A—C17A	121.79 (16)	C15B—C14B—C17B	120.87 (16)
C16A—C15A—C14A	121.88 (16)	C14B—C15B—C16B	121.28 (16)
C16A—C15A—H15A	119.1	C14B—C15B—H15B	119.4
C14A—C15A—H15A	119.1	C16B—C15B—H15B	119.4
C11A—C16A—C15A	118.95 (17)	C11B—C16B—C15B	118.88 (16)
C11A—C16A—H16A	120.5	C11B—C16B—H16B	120.6
C15A—C16A—H16A	120.5	C15B—C16B—H16B	120.6
C14A—C17A—H17D	109.5	C14B—C17B—H17A	109.5
C14A—C17A—H17E	109.5	C14B—C17B—H17B	109.5
H17D—C17A—H17E	109.5	H17A—C17B—H17B	109.5
C14A—C17A—H17F	109.5	C14B—C17B—H17C	109.5
H17D—C17A—H17F	109.5	H17A—C17B—H17C	109.5
H17E—C17A—H17F	109.5	H17B—C17B—H17C	109.5
C9A—N1A—C1A—C2A	178.47 (14)	C9B—N1B—C1B—C2B	179.00 (13)
C9A—N1A—C1A—C6A	0.2 (2)	C9B—N1B—C1B—C6B	0.8 (2)
N1A—C1A—C2A—C3A	−176.71 (15)	N1B—C1B—C2B—C3B	−178.08 (13)
C6A—C1A—C2A—C3A	1.6 (2)	C6B—C1B—C2B—C3B	0.2 (2)
C1A—C2A—C3A—C4A	−0.6 (3)	C1B—C2B—C3B—C4B	−0.6 (2)
C2A—C3A—C4A—C5A	−0.2 (3)	C2B—C3B—C4B—C5B	0.7 (2)
C3A—C4A—C5A—C6A	0.0 (3)	C3B—C4B—C5B—C6B	−0.3 (2)
C4A—C5A—C6A—C7A	179.93 (17)	C4B—C5B—C6B—C7B	179.09 (15)
C4A—C5A—C6A—C1A	1.1 (3)	C4B—C5B—C6B—C1B	−0.1 (2)
N1A—C1A—C6A—C7A	−2.5 (2)	N1B—C1B—C6B—C7B	−0.9 (2)
C2A—C1A—C6A—C7A	179.24 (15)	C2B—C1B—C6B—C7B	−179.09 (13)
N1A—C1A—C6A—C5A	176.45 (14)	N1B—C1B—C6B—C5B	178.34 (13)
C2A—C1A—C6A—C5A	−1.8 (2)	C2B—C1B—C6B—C5B	0.1 (2)
C5A—C6A—C7A—C8A	−176.68 (17)	C5B—C6B—C7B—C8B	−179.01 (14)
C1A—C6A—C7A—C8A	2.2 (2)	C1B—C6B—C7B—C8B	0.2 (2)
C6A—C7A—C8A—C9A	0.2 (3)	C6B—C7B—C8B—C9B	0.6 (2)
C1A—N1A—C9A—C8A	2.4 (2)	C1B—N1B—C9B—C8B	0.0 (2)
C1A—N1A—C9A—C10A	−174.34 (13)	C1B—N1B—C9B—C10B	−179.30 (12)
C7A—C8A—C9A—N1A	−2.7 (3)	C7B—C8B—C9B—N1B	−0.7 (2)
C7A—C8A—C9A—C10A	174.08 (16)	C7B—C8B—C9B—C10B	178.62 (14)
C11A—O1A—C10A—O2A	−2.1 (3)	C11B—O1B—C10B—O2B	−2.6 (2)
C11A—O1A—C10A—C9A	175.13 (14)	C11B—O1B—C10B—C9B	176.32 (13)
N1A—C9A—C10A—O2A	176.18 (17)	N1B—C9B—C10B—O2B	−167.71 (15)
C8A—C9A—C10A—O2A	−0.7 (3)	C8B—C9B—C10B—O2B	12.9 (2)
N1A—C9A—C10A—O1A	−1.0 (2)	N1B—C9B—C10B—O1B	13.42 (19)
C8A—C9A—C10A—O1A	−177.91 (15)	C8B—C9B—C10B—O1B	−165.96 (13)
C10A—O1A—C11A—C12A	−101.26 (19)	C10B—O1B—C11B—C12B	82.90 (19)
C10A—O1A—C11A—C16A	83.7 (2)	C10B—O1B—C11B—C16B	−101.91 (17)
C16A—C11A—C12A—C13A	−0.8 (3)	C16B—C11B—C12B—C13B	−0.3 (3)
O1A—C11A—C12A—C13A	−175.76 (16)	O1B—C11B—C12B—C13B	174.77 (15)
C11A—C12A—C13A—C14A	0.0 (3)	C11B—C12B—C13B—C14B	−0.1 (3)
C12A—C13A—C14A—C15A	0.7 (3)	C12B—C13B—C14B—C15B	0.8 (3)
C12A—C13A—C14A—C17A	−178.47 (18)	C12B—C13B—C14B—C17B	−179.43 (17)
C13A—C14A—C15A—C16A	−0.6 (3)	C13B—C14B—C15B—C16B	−1.0 (2)
C17A—C14A—C15A—C16A	178.60 (19)	C17B—C14B—C15B—C16B	179.21 (16)
C12A—C11A—C16A—C15A	0.9 (3)	C12B—C11B—C16B—C15B	0.1 (2)
O1A—C11A—C16A—C15A	175.81 (17)	O1B—C11B—C16B—C15B	−175.10 (13)
C14A—C15A—C16A—C11A	−0.2 (3)	C14B—C15B—C16B—C11B	0.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C15B—H15B···O2Ai	0.93	2.59	3.343 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15B—H15B⋯O2A i	0.93	2.59	3.343 (2)	138

Symmetry code: (i) .