Methyl (3S,10b'S)-5-chloro-9'-fluoro-1-methyl-2-oxo-5'-phenyl-10b'H-spiro-[indoline-3,1'-pyrazolo-[3,2-a]iso-quinoline]-2'-carboxyl-ate.

In the title compound, C27H19ClFN3O3, the pyrazole ring has a twist conformation and the six-membered ring to which it is fused has a screw-boat conformation. The mean plane of the pyrazole ring is inclined to the 2-methyl-indoline ring by 85.03 (9) and by 28.17 (8)° to the mean plane of the iso-quinoline ring system. In the crystal, mol-ecules are linked by pairs of C-H⋯F hydrogen bonds, forming inversion dimers. These dimers are linked via C-H⋯O hydrogen bonds, forming a two-dimensional network lying parallel to (10-1).

Related literature

For the biological activity of pyrazoles, see: Huang et al. (1996 ▶); Li et al. (2005 ▶); Patel et al. (1990 ▶); Zhao et al. (2001 ▶). For the crystal structures of pyrazoles, see: Manivel et al. (2009 ▶); Khan et al. (2010a ▶,b ▶,c ▶). For the crystal structure of an isoquinazole, see: Hathwar et al. (2008 ▶). For the biological activity of fused iso­quinoline compounds, see: Aubry et al. (2004 ▶); Marco et al. (2005 ▶); Reddy et al. (1999 ▶). For related structures, see: Chen & Wu (2010 ▶); Ye et al. (2010 ▶); Yu et al. (2011a ▶,b ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C27H19ClFN3O3

M = 487.90

Monoclinic,

a = 15.1203 (3) Å

b = 21.1088 (5) Å

c = 15.6334 (3) Å

β = 112.977 (1)°

V = 4593.85 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.21 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.940, T max = 0.959

22581 measured reflections

5703 independent reflections

4241 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.123

S = 1.03

5703 reflections

318 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813011549/su2581sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011549/su2581Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813011549/su2581Isup3.cml

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

C27H19ClFN3O3	F(000) = 2016
Mr = 487.90	Dx = 1.411 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5703 reflections
a = 15.1203 (3) Å	θ = 1.8–28.3°
b = 21.1088 (5) Å	µ = 0.21 mm−1
c = 15.6334 (3) Å	T = 293 K
β = 112.977 (1)°	Block, colourless
V = 4593.85 (17) Å3	0.30 × 0.25 × 0.20 mm
Z = 8

Bruker SMART APEXII area-detector diffractometer	5703 independent reflections
Radiation source: fine-focus sealed tube	4241 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scans	θmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −19→20
Tmin = 0.940, Tmax = 0.959	k = −26→28
22581 measured reflections	l = −20→20

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0562P)2 + 2.5788P] where P = (Fo2 + 2Fc2)/3
5703 reflections	(Δ/σ)max < 0.001
318 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.30 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 > 2sigma(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
C1	−0.17222 (12)	0.36693 (8)	0.05994 (11)	0.0504 (4)
C2	−0.13286 (15)	0.42416 (9)	0.09683 (14)	0.0633 (5)
H2	−0.1682	0.4526	0.1162	0.076*
C3	−0.04086 (15)	0.44005 (9)	0.10548 (14)	0.0640 (5)
H3	−0.0137	0.4788	0.1306	0.077*
C4	0.00932 (12)	0.39673 (7)	0.07581 (11)	0.0472 (4)
C5	−0.03056 (11)	0.33864 (7)	0.03903 (9)	0.0391 (3)
C6	−0.12155 (11)	0.32268 (7)	0.03097 (10)	0.0428 (3)
H6	−0.1483	0.2837	0.0070	0.051*
C7	0.04406 (10)	0.30004 (7)	0.02057 (9)	0.0374 (3)
C8	0.13007 (11)	0.34625 (7)	0.04972 (10)	0.0432 (3)
C9	0.02260 (11)	0.27304 (7)	−0.07765 (10)	0.0380 (3)
H9	0.0821	0.2753	−0.0885	0.046*
C10	−0.05599 (11)	0.30133 (7)	−0.16069 (10)	0.0390 (3)
C11	−0.06588 (13)	0.36633 (8)	−0.17251 (11)	0.0499 (4)
H11	−0.0280	0.3938	−0.1261	0.060*
C12	−0.13297 (14)	0.38943 (8)	−0.25436 (12)	0.0560 (4)
C13	−0.19128 (13)	0.35141 (9)	−0.32462 (12)	0.0539 (4)
H13	−0.2365	0.3687	−0.3787	0.065*
C14	−0.18089 (11)	0.28690 (8)	−0.31272 (11)	0.0465 (4)
H14	−0.2198	0.2603	−0.3598	0.056*
C15	−0.11317 (10)	0.26033 (7)	−0.23147 (10)	0.0389 (3)
C16	−0.09822 (11)	0.19251 (7)	−0.22125 (10)	0.0419 (3)
H16	−0.1288	0.1667	−0.2726	0.050*
C17	−0.04200 (11)	0.16548 (7)	−0.14060 (10)	0.0396 (3)
C18	−0.02320 (12)	0.09669 (7)	−0.12735 (11)	0.0444 (3)
C19	0.06896 (14)	0.07361 (8)	−0.08048 (13)	0.0564 (4)
H19	0.1201	0.1015	−0.0544	0.068*
C20	0.08479 (18)	0.00873 (10)	−0.07247 (16)	0.0731 (6)
H20	0.1468	−0.0066	−0.0413	0.088*
C21	0.0103 (2)	−0.03290 (10)	−0.10988 (17)	0.0782 (7)
H21	0.0215	−0.0763	−0.1035	0.094*
C22	−0.0807 (2)	−0.01051 (10)	−0.15659 (17)	0.0778 (6)
H22	−0.1313	−0.0389	−0.1824	0.093*
C23	−0.09844 (15)	0.05428 (9)	−0.16584 (13)	0.0605 (5)
H23	−0.1606	0.0691	−0.1978	0.073*
C24	0.06465 (10)	0.23823 (7)	0.07479 (10)	0.0381 (3)
C25	0.10235 (11)	0.23704 (8)	0.17662 (10)	0.0438 (3)
C26	0.14650 (18)	0.17390 (11)	0.31036 (13)	0.0757 (6)
H26A	0.2121	0.1879	0.3336	0.114*
H26B	0.1442	0.1306	0.3281	0.114*
H26C	0.1107	0.1998	0.3359	0.114*
C27	0.16737 (16)	0.45421 (10)	0.11482 (18)	0.0786 (6)
H27A	0.2259	0.4468	0.1060	0.118*
H27B	0.1814	0.4588	0.1799	0.118*
H27C	0.1375	0.4922	0.0828	0.118*
N1	0.00398 (10)	0.20592 (6)	−0.06590 (8)	0.0428 (3)
N2	0.03649 (9)	0.18827 (6)	0.02346 (8)	0.0406 (3)
N3	0.10284 (10)	0.40106 (6)	0.07812 (10)	0.0519 (3)
O1	0.20707 (8)	0.33595 (6)	0.04558 (8)	0.0542 (3)
O2	0.12795 (11)	0.28419 (6)	0.22236 (8)	0.0679 (4)
O3	0.10528 (9)	0.17891 (6)	0.21056 (8)	0.0561 (3)
Cl1	−0.28762 (4)	0.34823 (3)	0.05025 (4)	0.07239 (17)
F1	−0.13982 (11)	0.45332 (5)	−0.26685 (8)	0.0889 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0494 (9)	0.0546 (9)	0.0479 (8)	0.0061 (7)	0.0196 (7)	−0.0052 (7)
C2	0.0652 (12)	0.0565 (11)	0.0661 (11)	0.0122 (9)	0.0234 (9)	−0.0172 (9)
C3	0.0694 (13)	0.0430 (9)	0.0703 (12)	0.0002 (8)	0.0171 (10)	−0.0204 (8)
C4	0.0492 (9)	0.0393 (8)	0.0441 (8)	−0.0023 (7)	0.0085 (7)	−0.0063 (6)
C5	0.0443 (8)	0.0356 (7)	0.0335 (7)	0.0010 (6)	0.0111 (6)	−0.0034 (5)
C6	0.0457 (8)	0.0400 (7)	0.0421 (8)	0.0000 (6)	0.0164 (6)	−0.0041 (6)
C7	0.0373 (7)	0.0363 (7)	0.0356 (7)	−0.0032 (6)	0.0108 (6)	−0.0029 (5)
C8	0.0424 (8)	0.0425 (8)	0.0378 (7)	−0.0061 (6)	0.0080 (6)	0.0005 (6)
C9	0.0397 (7)	0.0380 (7)	0.0359 (7)	−0.0041 (6)	0.0144 (6)	−0.0034 (5)
C10	0.0412 (8)	0.0420 (7)	0.0356 (7)	−0.0016 (6)	0.0170 (6)	−0.0004 (6)
C11	0.0630 (10)	0.0433 (8)	0.0394 (8)	−0.0029 (7)	0.0157 (7)	−0.0006 (6)
C12	0.0731 (12)	0.0450 (9)	0.0482 (9)	0.0071 (8)	0.0220 (9)	0.0073 (7)
C13	0.0524 (10)	0.0635 (11)	0.0414 (8)	0.0107 (8)	0.0134 (7)	0.0082 (7)
C14	0.0382 (8)	0.0600 (10)	0.0391 (7)	−0.0022 (7)	0.0127 (6)	−0.0030 (7)
C15	0.0366 (7)	0.0461 (8)	0.0363 (7)	−0.0014 (6)	0.0167 (6)	−0.0021 (6)
C16	0.0413 (8)	0.0462 (8)	0.0387 (7)	−0.0068 (6)	0.0160 (6)	−0.0104 (6)
C17	0.0424 (8)	0.0391 (7)	0.0399 (7)	−0.0038 (6)	0.0189 (6)	−0.0083 (6)
C18	0.0566 (9)	0.0383 (7)	0.0425 (8)	−0.0018 (7)	0.0238 (7)	−0.0074 (6)
C19	0.0611 (11)	0.0460 (9)	0.0634 (11)	0.0044 (8)	0.0256 (9)	−0.0029 (8)
C20	0.0887 (15)	0.0547 (11)	0.0832 (14)	0.0205 (11)	0.0415 (13)	0.0057 (10)
C21	0.118 (2)	0.0417 (10)	0.0919 (16)	0.0034 (12)	0.0594 (15)	−0.0057 (10)
C22	0.1026 (18)	0.0479 (11)	0.0902 (16)	−0.0224 (11)	0.0456 (14)	−0.0230 (10)
C23	0.0689 (12)	0.0498 (10)	0.0619 (11)	−0.0118 (9)	0.0247 (9)	−0.0152 (8)
C24	0.0382 (7)	0.0378 (7)	0.0375 (7)	0.0009 (6)	0.0141 (6)	−0.0009 (5)
C25	0.0419 (8)	0.0494 (9)	0.0379 (7)	0.0009 (7)	0.0133 (6)	−0.0012 (6)
C26	0.0905 (16)	0.0884 (15)	0.0405 (9)	0.0013 (12)	0.0171 (10)	0.0156 (9)
C27	0.0661 (13)	0.0526 (11)	0.0986 (17)	−0.0201 (10)	0.0120 (12)	−0.0203 (11)
N1	0.0552 (8)	0.0337 (6)	0.0348 (6)	−0.0014 (5)	0.0122 (5)	−0.0025 (5)
N2	0.0437 (7)	0.0397 (6)	0.0371 (6)	0.0010 (5)	0.0144 (5)	−0.0013 (5)
N3	0.0491 (8)	0.0403 (7)	0.0564 (8)	−0.0105 (6)	0.0097 (6)	−0.0086 (6)
O1	0.0412 (6)	0.0587 (7)	0.0583 (7)	−0.0084 (5)	0.0147 (5)	−0.0007 (5)
O2	0.0896 (10)	0.0578 (8)	0.0428 (6)	−0.0015 (7)	0.0112 (6)	−0.0112 (6)
O3	0.0682 (8)	0.0573 (7)	0.0379 (6)	−0.0059 (6)	0.0154 (5)	0.0073 (5)
Cl1	0.0575 (3)	0.0824 (4)	0.0885 (4)	0.0046 (2)	0.0407 (3)	−0.0143 (3)
F1	0.1338 (12)	0.0469 (6)	0.0633 (7)	0.0117 (7)	0.0138 (7)	0.0139 (5)

C1—C2	1.370 (3)	C15—C16	1.448 (2)
C1—C6	1.391 (2)	C16—C17	1.342 (2)
C1—Cl1	1.7369 (18)	C16—H16	0.9300
C2—C3	1.385 (3)	C17—N1	1.3935 (18)
C2—H2	0.9300	C17—C18	1.478 (2)
C3—C4	1.379 (2)	C18—C19	1.385 (2)
C3—H3	0.9300	C18—C23	1.387 (2)
C4—C5	1.388 (2)	C19—C20	1.388 (3)
C4—N3	1.403 (2)	C19—H19	0.9300
C5—C6	1.374 (2)	C20—C21	1.367 (3)
C5—C7	1.508 (2)	C20—H20	0.9300
C6—H6	0.9300	C21—C22	1.366 (4)
C7—C24	1.521 (2)	C21—H21	0.9300
C7—C8	1.545 (2)	C22—C23	1.390 (3)
C7—C9	1.5489 (19)	C22—H22	0.9300
C8—O1	1.2107 (19)	C23—H23	0.9300
C8—N3	1.359 (2)	C24—N2	1.2926 (18)
C9—N1	1.4701 (18)	C24—C25	1.467 (2)
C9—C10	1.500 (2)	C25—O2	1.1981 (19)
C9—H9	0.9800	C25—O3	1.3308 (19)
C10—C11	1.385 (2)	C26—O3	1.440 (2)
C10—C15	1.405 (2)	C26—H26A	0.9600
C11—C12	1.375 (2)	C26—H26B	0.9600
C11—H11	0.9300	C26—H26C	0.9600
C12—F1	1.361 (2)	C27—N3	1.450 (2)
C12—C13	1.368 (3)	C27—H27A	0.9600
C13—C14	1.375 (2)	C27—H27B	0.9600
C13—H13	0.9300	C27—H27C	0.9600
C14—C15	1.400 (2)	N1—N2	1.3401 (17)
C14—H14	0.9300
C2—C1—C6	121.66 (17)	C17—C16—C15	122.56 (13)
C2—C1—Cl1	119.58 (13)	C17—C16—H16	118.7
C6—C1—Cl1	118.76 (13)	C15—C16—H16	118.7
C1—C2—C3	120.61 (16)	C16—C17—N1	116.91 (13)
C1—C2—H2	119.7	C16—C17—C18	124.46 (13)
C3—C2—H2	119.7	N1—C17—C18	118.58 (13)
C4—C3—C2	118.03 (16)	C19—C18—C23	119.20 (16)
C4—C3—H3	121.0	C19—C18—C17	121.21 (15)
C2—C3—H3	121.0	C23—C18—C17	119.53 (16)
C3—C4—C5	121.20 (16)	C18—C19—C20	119.83 (19)
C3—C4—N3	129.00 (15)	C18—C19—H19	120.1
C5—C4—N3	109.79 (14)	C20—C19—H19	120.1
C6—C5—C4	120.81 (14)	C21—C20—C19	120.8 (2)
C6—C5—C7	130.34 (13)	C21—C20—H20	119.6
C4—C5—C7	108.66 (13)	C19—C20—H20	119.6
C5—C6—C1	117.69 (14)	C22—C21—C20	119.7 (2)
C5—C6—H6	121.2	C22—C21—H21	120.1
C1—C6—H6	121.2	C20—C21—H21	120.1
C5—C7—C24	111.26 (11)	C21—C22—C23	120.6 (2)
C5—C7—C8	102.06 (12)	C21—C22—H22	119.7
C24—C7—C8	114.32 (12)	C23—C22—H22	119.7
C5—C7—C9	120.38 (12)	C18—C23—C22	119.9 (2)
C24—C7—C9	98.91 (11)	C18—C23—H23	120.1
C8—C7—C9	110.56 (12)	C22—C23—H23	120.1
O1—C8—N3	126.20 (15)	N2—C24—C25	123.66 (13)
O1—C8—C7	125.94 (14)	N2—C24—C7	114.07 (12)
N3—C8—C7	107.83 (13)	C25—C24—C7	121.86 (12)
N1—C9—C10	111.48 (12)	O2—C25—O3	125.12 (15)
N1—C9—C7	101.95 (11)	O2—C25—C24	122.13 (15)
C10—C9—C7	120.01 (12)	O3—C25—C24	112.75 (13)
N1—C9—H9	107.6	O3—C26—H26A	109.5
C10—C9—H9	107.6	O3—C26—H26B	109.5
C7—C9—H9	107.6	H26A—C26—H26B	109.5
C11—C10—C15	120.27 (14)	O3—C26—H26C	109.5
C11—C10—C9	121.18 (13)	H26A—C26—H26C	109.5
C15—C10—C9	118.20 (13)	H26B—C26—H26C	109.5
C12—C11—C10	118.52 (15)	N3—C27—H27A	109.5
C12—C11—H11	120.7	N3—C27—H27B	109.5
C10—C11—H11	120.7	H27A—C27—H27B	109.5
F1—C12—C13	118.49 (16)	N3—C27—H27C	109.5
F1—C12—C11	118.17 (16)	H27A—C27—H27C	109.5
C13—C12—C11	123.32 (16)	H27B—C27—H27C	109.5
C12—C13—C14	117.94 (15)	N2—N1—C17	124.28 (12)
C12—C13—H13	121.0	N2—N1—C9	112.83 (11)
C14—C13—H13	121.0	C17—N1—C9	122.89 (12)
C13—C14—C15	121.58 (15)	C24—N2—N1	108.56 (12)
C13—C14—H14	119.2	C8—N3—C4	111.52 (13)
C15—C14—H14	119.2	C8—N3—C27	123.02 (16)
C14—C15—C10	118.36 (14)	C4—N3—C27	125.18 (16)
C14—C15—C16	121.55 (14)	C25—O3—C26	115.63 (14)
C10—C15—C16	120.02 (13)
C6—C1—C2—C3	0.7 (3)	C14—C15—C16—C17	−172.17 (14)
Cl1—C1—C2—C3	179.82 (16)	C10—C15—C16—C17	10.8 (2)
C1—C2—C3—C4	0.1 (3)	C15—C16—C17—N1	−1.3 (2)
C2—C3—C4—C5	−0.5 (3)	C15—C16—C17—C18	−178.81 (14)
C2—C3—C4—N3	−179.09 (18)	C16—C17—C18—C19	134.10 (17)
C3—C4—C5—C6	0.1 (2)	N1—C17—C18—C19	−43.4 (2)
N3—C4—C5—C6	178.94 (14)	C16—C17—C18—C23	−43.1 (2)
C3—C4—C5—C7	−175.39 (16)	N1—C17—C18—C23	139.34 (16)
N3—C4—C5—C7	3.42 (17)	C23—C18—C19—C20	−0.1 (3)
C4—C5—C6—C1	0.7 (2)	C17—C18—C19—C20	−177.38 (16)
C7—C5—C6—C1	175.11 (15)	C18—C19—C20—C21	−0.4 (3)
C2—C1—C6—C5	−1.1 (2)	C19—C20—C21—C22	0.7 (3)
Cl1—C1—C6—C5	179.79 (12)	C20—C21—C22—C23	−0.5 (4)
C6—C5—C7—C24	−54.3 (2)	C19—C18—C23—C22	0.3 (3)
C4—C5—C7—C24	120.63 (13)	C17—C18—C23—C22	177.63 (17)
C6—C5—C7—C8	−176.67 (15)	C21—C22—C23—C18	0.0 (3)
C4—C5—C7—C8	−1.71 (15)	C5—C7—C24—N2	112.23 (14)
C6—C5—C7—C9	60.6 (2)	C8—C7—C24—N2	−132.82 (14)
C4—C5—C7—C9	−124.49 (14)	C9—C7—C24—N2	−15.38 (15)
C5—C7—C8—O1	−178.81 (15)	C5—C7—C24—C25	−60.72 (17)
C24—C7—C8—O1	60.97 (19)	C8—C7—C24—C25	54.23 (18)
C9—C7—C8—O1	−49.6 (2)	C9—C7—C24—C25	171.67 (13)
C5—C7—C8—N3	−0.59 (15)	N2—C24—C25—O2	179.97 (16)
C24—C7—C8—N3	−120.82 (14)	C7—C24—C25—O2	−7.8 (2)
C9—C7—C8—N3	128.63 (13)	N2—C24—C25—O3	0.6 (2)
C5—C7—C9—N1	−103.57 (14)	C7—C24—C25—O3	172.85 (13)
C24—C7—C9—N1	17.58 (13)	C16—C17—N1—N2	157.90 (14)
C8—C7—C9—N1	137.85 (12)	C18—C17—N1—N2	−24.4 (2)
C5—C7—C9—C10	20.10 (19)	C16—C17—N1—C9	−22.7 (2)
C24—C7—C9—C10	141.26 (13)	C18—C17—N1—C9	155.05 (14)
C8—C7—C9—C10	−98.48 (15)	C10—C9—N1—N2	−146.49 (12)
N1—C9—C10—C11	164.24 (13)	C7—C9—N1—N2	−17.24 (16)
C7—C9—C10—C11	45.3 (2)	C10—C9—N1—C17	34.01 (19)
N1—C9—C10—C15	−22.57 (18)	C7—C9—N1—C17	163.25 (13)
C7—C9—C10—C15	−141.53 (13)	C25—C24—N2—N1	178.35 (13)
C15—C10—C11—C12	0.4 (2)	C7—C24—N2—N1	5.55 (17)
C9—C10—C11—C12	173.48 (15)	C17—N1—N2—C24	−172.44 (14)
C10—C11—C12—F1	−177.63 (15)	C9—N1—N2—C24	8.07 (17)
C10—C11—C12—C13	0.6 (3)	O1—C8—N3—C4	−179.07 (15)
F1—C12—C13—C14	177.34 (16)	C7—C8—N3—C4	2.72 (18)
C11—C12—C13—C14	−0.9 (3)	O1—C8—N3—C27	−4.9 (3)
C12—C13—C14—C15	0.1 (2)	C7—C8—N3—C27	176.88 (16)
C13—C14—C15—C10	0.9 (2)	C3—C4—N3—C8	174.74 (18)
C13—C14—C15—C16	−176.19 (15)	C5—C4—N3—C8	−3.95 (19)
C11—C10—C15—C14	−1.1 (2)	C3—C4—N3—C27	0.7 (3)
C9—C10—C15—C14	−174.39 (13)	C5—C4—N3—C27	−177.97 (17)
C11—C10—C15—C16	175.96 (14)	O2—C25—O3—C26	−2.6 (3)
C9—C10—C15—C16	2.7 (2)	C24—C25—O3—C26	176.75 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27B···F1i	0.96	2.52	3.226 (3)	130
C14—H14···O1ii	0.93	2.50	3.402 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C27—H27B⋯F1i	0.96	2.52	3.226 (3)	130
C14—H14⋯O1ii	0.93	2.50	3.402 (2)	163

Symmetry codes: (i) ; (ii) .