tert-Butyl 2-{[2,8-bis-(trifluoro-meth-yl)quinolin-4-yl](hy-droxy)meth-yl}piperidine-1-carboxyl-ate.

The title mol-ecule, C(22)H(24)F(6)N(2)O(3), adopts a folded conformation whereby the carboxyl-ate residue lies over the quinolinyl residue, with the dihedral angle between the carbamate and quinoline planes being 41.64 (7)°. Helical supra-molecular C(7) chains sustained by O-H⋯O hydrogen bonds propagating along the a-axis direction feature in the crystal packing. The F atoms of one of the CF(3) groups are disordered over two orientations; the major component has a site occupancy of 0.824 (7).

Related literature

For background to the anti-mycobacterial activity of mefloquine, see: Gonçalves et al. (2010 ▶); Mao et al. (2007 ▶); Maguire et al. (2006 ▶). For the synthesis, see: Grellepois et al. (2005 ▶). For related structural studies, see: Gonçalves et al. (2011 ▶); de Souza et al. (2011 ▶); Wardell et al. (2010 ▶, 2011a ▶,b ▶); Pitaluga et al. (2010 ▶).

Experimental

Crystal data

C22H24F6N2O3

M = 478.43

Orthorhombic,

a = 9.888 (3) Å

b = 10.696 (3) Å

c = 21.158 (5) Å

V = 2237.7 (10) Å3

Z = 4

Cu Kα radiation

μ = 1.12 mm−1

T = 100 K

0.12 × 0.11 × 0.10 mm

Data collection

Rigaku Saturn944+ diffractometer

Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011 ▶) T min = 0.863, T max = 1.000

10899 measured reflections

3722 independent reflections

3640 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.130

S = 1.13

3722 reflections

314 parameters

31 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.44 e Å−3

Absolute structure: Flack (1983 ▶), 1532 Friedel pairs

Flack parameter: −0.08 (13)

Data collection: CrystalClear-SM Expert (Rigaku, 2011 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811047726/hb6499sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047726/hb6499Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811047726/hb6499Isup3.cml

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

C22H24F6N2O3	F(000) = 992
Mr = 478.43	Dx = 1.420 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2676 reflections
a = 9.888 (3) Å	θ = 21.7–66.3°
b = 10.696 (3) Å	µ = 1.12 mm−1
c = 21.158 (5) Å	T = 100 K
V = 2237.7 (10) Å3	Chip, colourless
Z = 4	0.12 × 0.11 × 0.10 mm

Rigaku Saturn944+ diffractometer	3722 independent reflections
Radiation source: fine-focus sealed tube	3640 reflections with I > 2σ(I)
confocal	Rint = 0.037
Detector resolution: 22.2222 pixels mm-1	θmax = 66.5°, θmin = 4.9°
profile data from ω–scans	h = −11→11
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011)	k = −11→12
Tmin = 0.863, Tmax = 1.000	l = −25→24
10899 measured reflections

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)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.0998P)2 + 0.2114P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
3722 reflections	Δρmax = 0.37 e Å−3
314 parameters	Δρmin = −0.44 e Å−3
31 restraints	Absolute structure: Flack (1983), 1532 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.08 (13)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
C10	0.2018 (3)	−0.0161 (2)	0.10080 (11)	0.0390 (6)	0.824 (7)
F1	0.1438 (3)	−0.0585 (4)	0.04787 (14)	0.0360 (7)	0.824 (7)
F2	0.0959 (3)	−0.0005 (3)	0.14211 (13)	0.0639 (10)	0.824 (7)
F3	0.2775 (3)	−0.1073 (2)	0.1234 (2)	0.0713 (10)	0.824 (7)
C10'	0.2018 (3)	−0.0161 (2)	0.10080 (11)	0.0390 (6)	0.176 (7)
F1'	0.1146 (16)	−0.050 (2)	0.0558 (8)	0.0360 (7)	0.176 (7)
F2'	0.1618 (18)	−0.0399 (15)	0.1586 (3)	0.0639 (10)	0.176 (7)
F3'	0.3022 (11)	−0.1023 (11)	0.0948 (8)	0.0713 (10)	0.176 (7)
F4	0.36443 (14)	0.19344 (13)	0.26991 (6)	0.0295 (3)
F5	0.55029 (14)	0.10401 (13)	0.24085 (6)	0.0304 (3)
F6	0.55644 (16)	0.27288 (15)	0.29575 (6)	0.0368 (4)
O1	0.31994 (19)	0.27116 (16)	−0.08675 (7)	0.0322 (4)
H1o	0.387 (3)	0.222 (3)	−0.0866 (17)	0.058*
O2	0.05287 (17)	0.37519 (15)	0.07601 (7)	0.0294 (4)
O3	0.11139 (19)	0.56561 (16)	0.11565 (8)	0.0303 (4)
N1	0.3449 (2)	0.14152 (17)	0.14112 (8)	0.0235 (4)
N2	0.1754 (2)	0.51397 (18)	0.01744 (8)	0.0257 (4)
C1	0.2766 (2)	0.1044 (2)	0.09080 (11)	0.0265 (5)
C2	0.2698 (2)	0.1688 (2)	0.03333 (11)	0.0270 (5)
H2	0.2194	0.1357	−0.0011	0.032*
C3	0.3375 (2)	0.2811 (2)	0.02730 (9)	0.0219 (5)
C4	0.4146 (2)	0.3242 (2)	0.07962 (10)	0.0199 (4)
C5	0.4941 (2)	0.4353 (2)	0.07868 (10)	0.0226 (4)
H5	0.4952	0.4858	0.0417	0.027*
C6	0.5686 (2)	0.4702 (2)	0.13000 (11)	0.0273 (5)
H6	0.6216	0.5442	0.1282	0.033*
C7	0.5678 (2)	0.3978 (2)	0.18567 (10)	0.0250 (5)
H7	0.6201	0.4232	0.2211	0.030*
C8	0.4923 (2)	0.2916 (2)	0.18890 (9)	0.0228 (5)
C9	0.4150 (2)	0.2504 (2)	0.13550 (9)	0.0202 (4)
C11	0.4905 (2)	0.2163 (2)	0.24812 (10)	0.0249 (5)
C12	0.3230 (2)	0.3538 (2)	−0.03392 (10)	0.0239 (5)
H12	0.3999	0.4139	−0.0385	0.029*
C13	0.1870 (2)	0.4255 (2)	−0.03579 (10)	0.0251 (5)
H13	0.1130	0.3625	−0.0311	0.030*
C14	0.2429 (3)	0.6364 (2)	0.01233 (11)	0.0313 (5)
H14A	0.3419	0.6247	0.0165	0.038*
H14B	0.2125	0.6908	0.0474	0.038*
C15	0.2123 (3)	0.7003 (2)	−0.05050 (12)	0.0374 (6)
H15A	0.1154	0.7233	−0.0522	0.045*
H15B	0.2663	0.7779	−0.0541	0.045*
C16	0.2459 (3)	0.6138 (2)	−0.10499 (12)	0.0363 (6)
H16A	0.3438	0.5946	−0.1047	0.044*
H16B	0.2239	0.6553	−0.1455	0.044*
C17	0.1649 (3)	0.4927 (2)	−0.09901 (11)	0.0314 (5)
H17A	0.1908	0.4358	−0.1339	0.038*
H17B	0.0675	0.5121	−0.1037	0.038*
C18	0.1084 (2)	0.4769 (2)	0.07035 (10)	0.0257 (5)
C19	0.0610 (2)	0.5418 (2)	0.18031 (10)	0.0281 (5)
C20	0.1404 (3)	0.4359 (3)	0.20999 (12)	0.0363 (6)
H20A	0.2374	0.4523	0.2055	0.054*
H20B	0.1177	0.3572	0.1887	0.054*
H20C	0.1173	0.4296	0.2549	0.054*
C21	−0.0903 (3)	0.5172 (3)	0.17923 (13)	0.0397 (6)
H21A	−0.1256	0.5193	0.2225	0.060*
H21B	−0.1075	0.4348	0.1606	0.060*
H21C	−0.1353	0.5816	0.1539	0.060*
C22	0.0909 (3)	0.6644 (3)	0.21311 (13)	0.0385 (6)
H22A	0.1879	0.6824	0.2103	0.058*
H22B	0.0643	0.6586	0.2576	0.058*
H22C	0.0398	0.7317	0.1926	0.058*

	U11	U22	U33	U12	U13	U23
C10	0.0500 (15)	0.0332 (13)	0.0339 (12)	−0.0136 (12)	−0.0226 (12)	0.0086 (11)
F1	0.0424 (15)	0.0259 (10)	0.0397 (11)	−0.0088 (13)	−0.0189 (12)	0.0016 (9)
F2	0.073 (2)	0.0671 (17)	0.0510 (13)	−0.0439 (16)	0.0102 (13)	−0.0066 (12)
F3	0.0817 (16)	0.0321 (10)	0.100 (2)	−0.0239 (10)	−0.0659 (17)	0.0395 (14)
C10'	0.0500 (15)	0.0332 (13)	0.0339 (12)	−0.0136 (12)	−0.0226 (12)	0.0086 (11)
F1'	0.0424 (15)	0.0259 (10)	0.0397 (11)	−0.0088 (13)	−0.0189 (12)	0.0016 (9)
F2'	0.073 (2)	0.0671 (17)	0.0510 (13)	−0.0439 (16)	0.0102 (13)	−0.0066 (12)
F3'	0.0817 (16)	0.0321 (10)	0.100 (2)	−0.0239 (10)	−0.0659 (17)	0.0395 (14)
F4	0.0283 (7)	0.0378 (8)	0.0224 (6)	0.0013 (6)	0.0021 (5)	0.0022 (5)
F5	0.0321 (7)	0.0321 (7)	0.0269 (6)	0.0082 (6)	−0.0020 (6)	0.0041 (5)
F6	0.0436 (8)	0.0447 (8)	0.0222 (6)	−0.0058 (7)	−0.0129 (6)	−0.0034 (6)
O1	0.0443 (10)	0.0316 (9)	0.0205 (7)	0.0090 (7)	−0.0063 (7)	−0.0056 (7)
O2	0.0323 (8)	0.0267 (8)	0.0292 (8)	−0.0045 (7)	0.0027 (7)	0.0001 (7)
O3	0.0389 (9)	0.0275 (8)	0.0246 (8)	−0.0020 (7)	0.0071 (7)	−0.0027 (6)
N1	0.0260 (9)	0.0208 (9)	0.0237 (8)	−0.0023 (7)	−0.0064 (8)	0.0003 (7)
N2	0.0317 (10)	0.0225 (9)	0.0229 (9)	−0.0001 (8)	0.0029 (8)	0.0004 (8)
C1	0.0306 (11)	0.0230 (11)	0.0259 (10)	−0.0030 (9)	−0.0095 (9)	0.0006 (8)
C2	0.0312 (11)	0.0248 (11)	0.0250 (10)	−0.0013 (9)	−0.0091 (9)	−0.0005 (9)
C3	0.0246 (10)	0.0211 (10)	0.0199 (10)	0.0013 (9)	−0.0028 (8)	−0.0022 (8)
C4	0.0192 (9)	0.0193 (10)	0.0211 (9)	0.0024 (8)	0.0019 (8)	−0.0026 (8)
C5	0.0229 (10)	0.0228 (10)	0.0221 (9)	0.0001 (9)	0.0017 (8)	0.0006 (8)
C6	0.0255 (11)	0.0260 (11)	0.0304 (11)	−0.0058 (9)	0.0017 (9)	−0.0031 (9)
C7	0.0239 (10)	0.0284 (12)	0.0226 (9)	−0.0024 (9)	−0.0037 (8)	−0.0070 (9)
C8	0.0214 (10)	0.0257 (11)	0.0213 (10)	0.0012 (9)	−0.0008 (8)	−0.0035 (8)
C9	0.0184 (9)	0.0215 (10)	0.0207 (9)	0.0014 (8)	−0.0009 (8)	−0.0023 (8)
C11	0.0247 (10)	0.0300 (11)	0.0201 (10)	−0.0012 (9)	−0.0025 (8)	−0.0018 (8)
C12	0.0306 (11)	0.0220 (11)	0.0190 (9)	0.0014 (9)	−0.0022 (9)	−0.0012 (8)
C13	0.0298 (11)	0.0232 (12)	0.0223 (10)	−0.0005 (9)	−0.0036 (9)	−0.0004 (8)
C14	0.0389 (13)	0.0224 (11)	0.0326 (11)	0.0000 (10)	0.0024 (10)	0.0025 (9)
C15	0.0451 (14)	0.0284 (13)	0.0388 (13)	0.0025 (11)	0.0041 (11)	0.0102 (11)
C16	0.0454 (14)	0.0337 (14)	0.0298 (12)	0.0023 (12)	0.0025 (11)	0.0120 (10)
C17	0.0362 (12)	0.0341 (13)	0.0241 (10)	0.0065 (11)	−0.0047 (10)	0.0024 (9)
C18	0.0270 (10)	0.0238 (11)	0.0262 (10)	0.0025 (9)	−0.0001 (9)	−0.0009 (9)
C19	0.0257 (11)	0.0353 (13)	0.0233 (10)	0.0002 (10)	0.0035 (9)	−0.0002 (9)
C20	0.0407 (14)	0.0378 (14)	0.0305 (11)	0.0052 (11)	−0.0030 (11)	0.0020 (10)
C21	0.0269 (12)	0.0556 (17)	0.0365 (13)	0.0004 (12)	0.0037 (10)	−0.0108 (12)
C22	0.0416 (14)	0.0395 (14)	0.0344 (12)	−0.0026 (12)	0.0052 (11)	−0.0119 (11)

C10—F3	1.319 (3)	C7—C8	1.361 (3)
C10—F1	1.338 (3)	C7—H7	0.9500
C10—F2	1.374 (3)	C8—C9	1.433 (3)
C10—C1	1.501 (3)	C8—C11	1.490 (3)
C10'—F1'	1.335 (5)	C12—C13	1.548 (3)
C10'—F2'	1.310 (5)	C12—H12	1.0000
C10'—C1	1.501 (3)	C13—C17	1.534 (3)
C10'—F3'	1.360 (5)	C13—H13	1.0000
F4—C11	1.352 (3)	C14—C15	1.526 (3)
F5—C11	1.347 (3)	C14—H14A	0.9900
F6—C11	1.344 (3)	C14—H14B	0.9900
O1—C12	1.425 (3)	C15—C16	1.515 (4)
O1—H1O	0.843 (11)	C15—H15A	0.9900
O2—C18	1.225 (3)	C15—H15B	0.9900
O3—C18	1.349 (3)	C16—C17	1.527 (4)
O3—C19	1.478 (3)	C16—H16A	0.9900
N1—C1	1.322 (3)	C16—H16B	0.9900
N1—C9	1.361 (3)	C17—H17A	0.9900
N2—C18	1.360 (3)	C17—H17B	0.9900
N2—C14	1.474 (3)	C19—C22	1.513 (4)
N2—C13	1.476 (3)	C19—C20	1.515 (4)
C1—C2	1.399 (3)	C19—C21	1.519 (4)
C2—C3	1.381 (3)	C20—H20A	0.9800
C2—H2	0.9500	C20—H20B	0.9800
C3—C4	1.421 (3)	C20—H20C	0.9800
C3—C12	1.517 (3)	C21—H21A	0.9800
C4—C9	1.422 (3)	C21—H21B	0.9800
C4—C5	1.425 (3)	C21—H21C	0.9800
C5—C6	1.364 (3)	C22—H22A	0.9800
C5—H5	0.9500	C22—H22B	0.9800
C6—C7	1.410 (3)	C22—H22C	0.9800
C6—H6	0.9500
F3—C10—F1	107.2 (3)	C13—C12—H12	109.8
F3—C10—F2	106.9 (3)	N2—C13—C17	110.70 (18)
F1—C10—F2	104.3 (2)	N2—C13—C12	111.47 (18)
F3—C10—C1	114.1 (2)	C17—C13—C12	112.22 (19)
F1—C10—C1	112.6 (3)	N2—C13—H13	107.4
F2—C10—C1	111.2 (2)	C17—C13—H13	107.4
F1'—C10'—F2'	114.7 (11)	C12—C13—H13	107.4
F1'—C10'—C1	116.8 (12)	N2—C14—C15	111.9 (2)
F2'—C10'—C1	116.6 (6)	N2—C14—H14A	109.2
F1'—C10'—F3'	102.8 (10)	C15—C14—H14A	109.2
F2'—C10'—F3'	100.1 (8)	N2—C14—H14B	109.2
C1—C10'—F3'	102.1 (7)	C15—C14—H14B	109.2
C12—O1—H1O	111 (3)	H14A—C14—H14B	107.9
C18—O3—C19	121.93 (18)	C16—C15—C14	110.2 (2)
C1—N1—C9	116.55 (18)	C16—C15—H15A	109.6
C18—N2—C14	122.69 (18)	C14—C15—H15A	109.6
C18—N2—C13	118.66 (19)	C16—C15—H15B	109.6
C14—N2—C13	118.57 (17)	C14—C15—H15B	109.6
N1—C1—C2	125.2 (2)	H15A—C15—H15B	108.1
N1—C1—C10'	113.32 (18)	C15—C16—C17	109.9 (2)
C2—C1—C10'	121.47 (19)	C15—C16—H16A	109.7
N1—C1—C10	113.32 (18)	C17—C16—H16A	109.7
C2—C1—C10	121.47 (19)	C15—C16—H16B	109.7
C3—C2—C1	119.1 (2)	C17—C16—H16B	109.7
C3—C2—H2	120.5	H16A—C16—H16B	108.2
C1—C2—H2	120.5	C16—C17—C13	113.3 (2)
C2—C3—C4	118.04 (19)	C16—C17—H17A	108.9
C2—C3—C12	118.62 (19)	C13—C17—H17A	108.9
C4—C3—C12	123.32 (19)	C16—C17—H17B	108.9
C3—C4—C9	117.99 (19)	C13—C17—H17B	108.9
C3—C4—C5	123.76 (19)	H17A—C17—H17B	107.7
C9—C4—C5	118.23 (18)	O2—C18—O3	124.4 (2)
C6—C5—C4	121.0 (2)	O2—C18—N2	123.9 (2)
C6—C5—H5	119.5	O3—C18—N2	111.7 (2)
C4—C5—H5	119.5	O3—C19—C22	102.08 (19)
C5—C6—C7	120.8 (2)	O3—C19—C20	109.75 (19)
C5—C6—H6	119.6	C22—C19—C20	110.9 (2)
C7—C6—H6	119.6	O3—C19—C21	110.4 (2)
C8—C7—C6	120.2 (2)	C22—C19—C21	110.4 (2)
C8—C7—H7	119.9	C20—C19—C21	112.8 (2)
C6—C7—H7	119.9	C19—C20—H20A	109.5
C7—C8—C9	120.6 (2)	C19—C20—H20B	109.5
C7—C8—C11	119.99 (19)	H20A—C20—H20B	109.5
C9—C8—C11	119.39 (19)	C19—C20—H20C	109.5
N1—C9—C4	123.13 (18)	H20A—C20—H20C	109.5
N1—C9—C8	117.76 (18)	H20B—C20—H20C	109.5
C4—C9—C8	119.12 (19)	C19—C21—H21A	109.5
F6—C11—F5	105.93 (18)	C19—C21—H21B	109.5
F6—C11—F4	105.84 (18)	H21A—C21—H21B	109.5
F5—C11—F4	106.39 (18)	C19—C21—H21C	109.5
F6—C11—C8	112.43 (19)	H21A—C21—H21C	109.5
F5—C11—C8	112.38 (18)	H21B—C21—H21C	109.5
F4—C11—C8	113.30 (18)	C19—C22—H22A	109.5
O1—C12—C3	110.71 (18)	C19—C22—H22B	109.5
O1—C12—C13	105.59 (17)	H22A—C22—H22B	109.5
C3—C12—C13	110.95 (18)	C19—C22—H22C	109.5
O1—C12—H12	109.8	H22A—C22—H22C	109.5
C3—C12—H12	109.8	H22B—C22—H22C	109.5
C9—N1—C1—C2	−0.8 (3)	C3—C4—C9—C8	179.82 (19)
C9—N1—C1—C10'	−179.89 (19)	C5—C4—C9—C8	1.4 (3)
C9—N1—C1—C10	−179.89 (19)	C7—C8—C9—N1	178.1 (2)
F1'—C10'—C1—N1	170.2 (10)	C11—C8—C9—N1	−1.4 (3)
F2'—C10'—C1—N1	29.4 (10)	C7—C8—C9—C4	−2.1 (3)
F3'—C10'—C1—N1	−78.6 (7)	C11—C8—C9—C4	178.51 (19)
F1'—C10'—C1—C2	−8.9 (10)	C7—C8—C11—F6	6.8 (3)
F2'—C10'—C1—C2	−149.7 (10)	C9—C8—C11—F6	−173.75 (19)
F3'—C10'—C1—C2	102.3 (7)	C7—C8—C11—F5	−112.6 (2)
F1'—C10'—C1—C10	0(100)	C9—C8—C11—F5	66.8 (3)
F2'—C10'—C1—C10	0(98)	C7—C8—C11—F4	126.8 (2)
F3'—C10'—C1—C10	0(54)	C9—C8—C11—F4	−53.8 (3)
F3—C10—C1—N1	−51.6 (4)	C2—C3—C12—O1	−38.0 (3)
F1—C10—C1—N1	−174.0 (3)	C4—C3—C12—O1	143.6 (2)
F2—C10—C1—N1	69.4 (3)	C2—C3—C12—C13	78.9 (2)
F3—C10—C1—C2	129.3 (3)	C4—C3—C12—C13	−99.5 (2)
F1—C10—C1—C2	6.9 (4)	C18—N2—C13—C17	138.6 (2)
F2—C10—C1—C2	−109.7 (3)	C14—N2—C13—C17	−44.6 (3)
F3—C10—C1—C10'	0(16)	C18—N2—C13—C12	−95.8 (2)
F1—C10—C1—C10'	0(100)	C14—N2—C13—C12	81.1 (2)
F2—C10—C1—C10'	0(100)	O1—C12—C13—N2	179.09 (17)
N1—C1—C2—C3	−0.8 (4)	C3—C12—C13—N2	59.1 (2)
C10'—C1—C2—C3	178.2 (2)	O1—C12—C13—C17	−56.1 (2)
C10—C1—C2—C3	178.2 (2)	C3—C12—C13—C17	−176.08 (19)
C1—C2—C3—C4	1.9 (3)	C18—N2—C14—C15	−134.8 (2)
C1—C2—C3—C12	−176.6 (2)	C13—N2—C14—C15	48.5 (3)
C2—C3—C4—C9	−1.3 (3)	N2—C14—C15—C16	−53.7 (3)
C12—C3—C4—C9	177.02 (19)	C14—C15—C16—C17	58.2 (3)
C2—C3—C4—C5	177.0 (2)	C15—C16—C17—C13	−56.3 (3)
C12—C3—C4—C5	−4.7 (3)	N2—C13—C17—C16	47.6 (3)
C3—C4—C5—C6	−178.4 (2)	C12—C13—C17—C16	−77.6 (2)
C9—C4—C5—C6	−0.1 (3)	C19—O3—C18—O2	7.6 (3)
C4—C5—C6—C7	−0.6 (3)	C19—O3—C18—N2	−172.07 (19)
C5—C6—C7—C8	0.0 (3)	C14—N2—C18—O2	−179.1 (2)
C6—C7—C8—C9	1.3 (3)	C13—N2—C18—O2	−2.4 (3)
C6—C7—C8—C11	−179.2 (2)	C14—N2—C18—O3	0.6 (3)
C1—N1—C9—C4	1.4 (3)	C13—N2—C18—O3	177.28 (18)
C1—N1—C9—C8	−178.7 (2)	C18—O3—C19—C22	177.8 (2)
C3—C4—C9—N1	−0.3 (3)	C18—O3—C19—C20	60.1 (3)
C5—C4—C9—N1	−178.73 (19)	C18—O3—C19—C21	−64.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2i	0.85 (3)	1.96 (3)	2.794 (3)	171 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O2i	0.85 (3)	1.96 (3)	2.794 (3)	171 (3)

Symmetry code: (i) .