N-{3-[2-(4-Fluoro-phen-oxy)eth-yl]-2,4-dioxo-1,3-diaza-spiro-[4.5]decan-7-yl}-4-meth-oxy-benzene-sulfonamide.

In the title compound, C(23)H(26)FN(3)O(6)S, the two terminal aromatic rings form a dihedral angle of 49.26 (12)°. The cyclo-hexane ring adopts a chair conformation and the five-membered ring is essentially planar, with a maximum deviation from planarity of 0.0456 (19) Å. The dihedral angles between the five-membered ring and the meth-oxy-benzene and fluoro-benzene rings are 33.56 (11) and 81.94 (12)°, respectively. The crystal structure displays N-H⋯O hydrogen bonds as well as weak inter-molecular C-H⋯O inter-actions.

Related literature

For the biological activity of related compounds, see: Cartwright et al. (2007 ▶); Collins (2000 ▶); Warshakoon et al. (2006 ▶) and for their pharmaceutical activity, see: Kiselyov et al. (2006 ▶); Sakthivel & Cook (2005 ▶); Eldrup et al. (2004 ▶); Bamford et al. (2005 ▶); Puerstinger et al. (2006 ▶).

Experimental

Crystal data

C23H26FN3O6S

M = 491.53

Monoclinic,

a = 11.926 (5) Å

b = 11.025 (5) Å

c = 18.508 (5) Å

β = 97.271 (5)°

V = 2413.9 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 293 K

0.20 × 0.15 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010 ▶) T min = 0.771, T max = 1.000

21931 measured reflections

4240 independent reflections

3435 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.121

S = 1.04

4240 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.50 e Å−3

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811053980/pk2365sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053980/pk2365Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811053980/pk2365Isup3.cml

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

C23H26FN3O6S	F(000) = 1032
Mr = 491.53	Dx = 1.352 Mg m−3
Monoclinic, P21/c	Melting point: 454 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.926 (5) Å	Cell parameters from 4240 reflections
b = 11.025 (5) Å	θ = 2.2–25.0°
c = 18.508 (5) Å	µ = 0.19 mm−1
β = 97.271 (5)°	T = 293 K
V = 2413.9 (16) Å3	Prism, colourless
Z = 4	0.20 × 0.15 × 0.12 mm

Oxford Diffraction Xcalibur diffractometer	4240 independent reflections
Radiation source: fine-focus sealed tube	3435 reflections with I > 2σ(I)
graphite	Rint = 0.035
Detector resolution: 15.9821 pixels mm-1	θmax = 25.0°, θmin = 2.2°
ω scans	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010)	k = −13→10
Tmin = 0.771, Tmax = 1.000	l = −20→22
21931 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0687P)2 + 0.7995P] where P = (Fo2 + 2Fc2)/3
4240 reflections	(Δ/σ)max < 0.001
307 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.50 e Å−3

Experimental. CrysAlis PRO, Oxford Diffraction Ltd. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.Colourless solid: Yield: 103 mg, 67%); mp: 454k; IR cm-1 (KBr) 3359 (N—H), 1340 (S=O); Anal. Calcd For C23H26FN3O6S: C, 56.20; H, 5.33; N, 8.55%, Found, C, 55.09; H, 5.35; N, 8.45%.

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
S1	0.47387 (4)	0.20854 (4)	−0.01227 (2)	0.03209 (16)
F2	1.00980 (18)	−0.1496 (2)	0.04785 (12)	0.1244 (9)
O3	0.80071 (13)	0.03367 (15)	0.26846 (9)	0.0512 (4)
O4	0.70270 (13)	0.38222 (13)	0.31425 (10)	0.0552 (5)
O5	0.56248 (13)	0.00010 (12)	0.32549 (8)	0.0412 (4)
O6	0.48854 (13)	0.12205 (13)	−0.06840 (7)	0.0426 (4)
O7	0.40333 (13)	0.31161 (13)	−0.02950 (8)	0.0434 (4)
O8	0.91812 (15)	0.39441 (16)	0.11131 (11)	0.0691 (6)
N9	0.65657 (14)	0.18207 (14)	0.33157 (9)	0.0351 (4)
N10	0.53633 (14)	0.29687 (14)	0.26198 (9)	0.0354 (4)
H10	0.5036	0.3604	0.2423	0.042*
N11	0.42293 (14)	0.13132 (14)	0.04977 (8)	0.0327 (4)
H11	0.4017	0.0575	0.0414	0.039*
C12	1.0152 (2)	0.3203 (3)	0.1158 (2)	0.0834 (10)
H12A	1.0800	0.3661	0.1363	0.125*
H12B	1.0261	0.2930	0.0679	0.125*
H12C	1.0056	0.2516	0.1462	0.125*
C13	0.81799 (19)	0.3448 (2)	0.08321 (13)	0.0463 (5)
C14	0.7260 (2)	0.4222 (2)	0.07640 (15)	0.0580 (7)
H14	0.7353	0.5024	0.0916	0.070*
C15	0.6212 (2)	0.3816 (2)	0.04736 (13)	0.0473 (6)
H15	0.5595	0.4339	0.0431	0.057*
C16	0.60774 (17)	0.26262 (18)	0.02452 (10)	0.0338 (4)
C17	0.69896 (18)	0.18514 (18)	0.03223 (12)	0.0399 (5)
H17	0.6894	0.1048	0.0174	0.048*
C18	0.80392 (19)	0.22515 (19)	0.06158 (12)	0.0442 (5)
H18	0.8651	0.1722	0.0669	0.053*
C19	0.41262 (16)	0.18727 (16)	0.12110 (10)	0.0287 (4)
H19	0.4333	0.2731	0.1192	0.034*
C20	0.29275 (16)	0.17830 (19)	0.13882 (11)	0.0362 (5)
H20A	0.2691	0.0941	0.1369	0.043*
H20B	0.2427	0.2230	0.1029	0.043*
C21	0.28410 (17)	0.2295 (2)	0.21439 (11)	0.0395 (5)
H21A	0.2994	0.3159	0.2144	0.047*
H21B	0.2077	0.2182	0.2260	0.047*
C22	0.36675 (17)	0.16844 (19)	0.27258 (11)	0.0361 (5)
H22A	0.3624	0.2074	0.3191	0.043*
H22B	0.3456	0.0840	0.2769	0.043*
C23	0.48732 (16)	0.17553 (16)	0.25459 (10)	0.0289 (4)
C24	0.49523 (16)	0.12453 (17)	0.17834 (10)	0.0286 (4)
H24A	0.5716	0.1353	0.1665	0.034*
H24B	0.4792	0.0383	0.1780	0.034*
C25	0.57017 (17)	0.10571 (17)	0.30816 (10)	0.0311 (4)
C26	0.63708 (18)	0.29892 (17)	0.30243 (11)	0.0367 (5)
C27	0.76450 (18)	0.1454 (2)	0.37032 (12)	0.0441 (5)
H27A	0.7544	0.0724	0.3981	0.053*
H27B	0.7926	0.2087	0.4043	0.053*
C28	0.84957 (19)	0.1217 (2)	0.31867 (13)	0.0458 (6)
H28A	0.8655	0.1957	0.2935	0.055*
H28B	0.9196	0.0916	0.3449	0.055*
C29	0.85919 (18)	−0.00587 (18)	0.21384 (12)	0.0396 (5)
C30	0.97395 (19)	0.0047 (2)	0.21463 (14)	0.0531 (6)
H30	1.0172	0.0442	0.2529	0.064*
C31	1.0247 (2)	−0.0442 (3)	0.15802 (17)	0.0681 (8)
H31	1.1024	−0.0383	0.1576	0.082*
C32	0.9586 (3)	−0.1007 (3)	0.10314 (16)	0.0697 (8)
C33	0.8452 (2)	−0.1123 (3)	0.10093 (14)	0.0603 (7)
H33	0.8026	−0.1520	0.0625	0.072*
C34	0.79498 (19)	−0.0639 (2)	0.15697 (12)	0.0445 (5)
H34	0.7171	−0.0701	0.1566	0.053*

	U11	U22	U33	U12	U13	U23
S1	0.0411 (3)	0.0306 (3)	0.0236 (3)	0.0057 (2)	0.0004 (2)	0.00054 (19)
F2	0.0994 (16)	0.175 (2)	0.1085 (16)	0.0153 (15)	0.0523 (13)	−0.0535 (16)
O3	0.0437 (9)	0.0566 (10)	0.0553 (10)	−0.0118 (7)	0.0141 (8)	−0.0204 (8)
O4	0.0466 (10)	0.0331 (8)	0.0815 (12)	−0.0075 (7)	−0.0092 (8)	−0.0083 (8)
O5	0.0548 (9)	0.0280 (8)	0.0388 (8)	−0.0002 (6)	−0.0021 (7)	0.0041 (6)
O6	0.0604 (10)	0.0421 (8)	0.0248 (7)	0.0048 (7)	0.0039 (7)	−0.0062 (6)
O7	0.0495 (9)	0.0380 (8)	0.0398 (8)	0.0113 (7)	−0.0049 (7)	0.0062 (6)
O8	0.0452 (10)	0.0561 (11)	0.1003 (15)	0.0045 (8)	−0.0131 (10)	−0.0252 (10)
N9	0.0392 (10)	0.0283 (8)	0.0354 (9)	0.0025 (7)	−0.0046 (8)	−0.0064 (7)
N10	0.0425 (10)	0.0230 (8)	0.0383 (10)	0.0022 (7)	−0.0043 (8)	−0.0016 (7)
N11	0.0451 (10)	0.0271 (8)	0.0256 (8)	−0.0028 (7)	0.0033 (7)	−0.0059 (6)
C12	0.0443 (16)	0.0728 (19)	0.126 (3)	0.0066 (14)	−0.0180 (17)	−0.0291 (19)
C13	0.0416 (13)	0.0453 (12)	0.0501 (14)	0.0021 (10)	−0.0018 (10)	−0.0093 (11)
C14	0.0518 (15)	0.0392 (12)	0.0798 (18)	0.0044 (11)	−0.0039 (13)	−0.0195 (12)
C15	0.0448 (13)	0.0353 (12)	0.0599 (15)	0.0106 (10)	−0.0008 (11)	−0.0076 (10)
C16	0.0409 (11)	0.0325 (10)	0.0283 (10)	0.0043 (9)	0.0065 (9)	0.0020 (8)
C17	0.0442 (12)	0.0285 (10)	0.0469 (13)	0.0041 (9)	0.0056 (10)	−0.0014 (9)
C18	0.0410 (12)	0.0382 (12)	0.0526 (14)	0.0107 (10)	0.0034 (10)	0.0002 (10)
C19	0.0367 (11)	0.0249 (9)	0.0242 (9)	−0.0002 (8)	0.0022 (8)	−0.0033 (7)
C20	0.0321 (11)	0.0398 (11)	0.0356 (11)	0.0041 (9)	−0.0001 (9)	0.0002 (9)
C21	0.0332 (11)	0.0441 (12)	0.0424 (12)	0.0063 (9)	0.0088 (9)	−0.0015 (10)
C22	0.0404 (12)	0.0389 (11)	0.0304 (10)	0.0021 (9)	0.0093 (9)	−0.0013 (9)
C23	0.0355 (11)	0.0234 (9)	0.0273 (10)	0.0003 (8)	0.0023 (8)	−0.0019 (7)
C24	0.0305 (10)	0.0274 (9)	0.0276 (10)	0.0017 (8)	0.0028 (8)	−0.0023 (7)
C25	0.0402 (11)	0.0288 (10)	0.0242 (10)	0.0021 (8)	0.0034 (8)	−0.0042 (8)
C26	0.0397 (12)	0.0286 (10)	0.0408 (12)	0.0019 (9)	0.0013 (9)	−0.0073 (8)
C27	0.0452 (13)	0.0442 (12)	0.0389 (12)	0.0065 (10)	−0.0103 (10)	−0.0079 (10)
C28	0.0397 (12)	0.0417 (12)	0.0533 (14)	−0.0008 (10)	−0.0052 (10)	−0.0076 (10)
C29	0.0412 (12)	0.0351 (11)	0.0434 (12)	0.0014 (9)	0.0086 (10)	0.0045 (9)
C30	0.0383 (13)	0.0600 (15)	0.0608 (15)	−0.0006 (11)	0.0054 (11)	0.0004 (12)
C31	0.0419 (14)	0.082 (2)	0.084 (2)	0.0089 (14)	0.0229 (14)	0.0029 (17)
C32	0.0637 (18)	0.086 (2)	0.0642 (18)	0.0148 (15)	0.0266 (15)	−0.0129 (15)
C33	0.0612 (17)	0.0694 (17)	0.0505 (15)	0.0038 (13)	0.0083 (13)	−0.0111 (13)
C34	0.0404 (12)	0.0468 (13)	0.0464 (13)	0.0008 (10)	0.0065 (10)	0.0011 (10)

S1—O7	1.4258 (15)	C19—C20	1.510 (3)
S1—O6	1.4370 (15)	C19—C24	1.519 (3)
S1—N11	1.6092 (17)	C19—H19	0.9800
S1—C16	1.759 (2)	C20—C21	1.524 (3)
F2—C32	1.367 (3)	C20—H20A	0.9700
O3—C29	1.370 (3)	C20—H20B	0.9700
O3—C28	1.417 (3)	C21—C22	1.522 (3)
O4—C26	1.209 (2)	C21—H21A	0.9700
O5—C25	1.214 (2)	C21—H21B	0.9700
O8—C13	1.356 (3)	C22—C23	1.518 (3)
O8—C12	1.411 (3)	C22—H22A	0.9700
N9—C25	1.358 (3)	C22—H22B	0.9700
N9—C26	1.405 (3)	C23—C25	1.518 (3)
N9—C27	1.449 (3)	C23—C24	1.533 (3)
N10—C26	1.333 (3)	C24—H24A	0.9700
N10—C23	1.459 (2)	C24—H24B	0.9700
N10—H10	0.8600	C27—C28	1.502 (3)
N11—C19	1.476 (2)	C27—H27A	0.9700
N11—H11	0.8600	C27—H27B	0.9700
C12—H12A	0.9600	C28—H28A	0.9700
C12—H12B	0.9600	C28—H28B	0.9700
C12—H12C	0.9600	C29—C30	1.372 (3)
C13—C18	1.383 (3)	C29—C34	1.378 (3)
C13—C14	1.383 (3)	C30—C31	1.384 (4)
C14—C15	1.372 (3)	C30—H30	0.9300
C14—H14	0.9300	C31—C32	1.356 (4)
C15—C16	1.382 (3)	C31—H31	0.9300
C15—H15	0.9300	C32—C33	1.354 (4)
C16—C17	1.376 (3)	C33—C34	1.370 (3)
C17—C18	1.373 (3)	C33—H33	0.9300
C17—H17	0.9300	C34—H34	0.9300
C18—H18	0.9300
O7—S1—O6	119.32 (9)	C20—C21—H21B	109.2
O7—S1—N11	108.41 (9)	H21A—C21—H21B	107.9
O6—S1—N11	104.85 (9)	C23—C22—C21	111.63 (16)
O7—S1—C16	107.30 (10)	C23—C22—H22A	109.3
O6—S1—C16	108.50 (10)	C21—C22—H22A	109.3
N11—S1—C16	108.01 (9)	C23—C22—H22B	109.3
C29—O3—C28	119.76 (17)	C21—C22—H22B	109.3
C13—O8—C12	117.8 (2)	H22A—C22—H22B	108.0
C25—N9—C26	111.34 (16)	N10—C23—C25	100.59 (15)
C25—N9—C27	125.11 (17)	N10—C23—C22	113.94 (16)
C26—N9—C27	122.64 (18)	C25—C23—C22	112.77 (16)
C26—N10—C23	112.96 (15)	N10—C23—C24	110.60 (15)
C26—N10—H10	123.5	C25—C23—C24	107.72 (15)
C23—N10—H10	123.5	C22—C23—C24	110.69 (16)
C19—N11—S1	119.92 (13)	C19—C24—C23	111.41 (15)
C19—N11—H11	120.0	C19—C24—H24A	109.3
S1—N11—H11	120.0	C23—C24—H24A	109.3
O8—C12—H12A	109.5	C19—C24—H24B	109.3
O8—C12—H12B	109.5	C23—C24—H24B	109.3
H12A—C12—H12B	109.5	H24A—C24—H24B	108.0
O8—C12—H12C	109.5	O5—C25—N9	126.13 (18)
H12A—C12—H12C	109.5	O5—C25—C23	126.45 (18)
H12B—C12—H12C	109.5	N9—C25—C23	107.39 (16)
O8—C13—C18	124.4 (2)	O4—C26—N10	129.17 (19)
O8—C13—C14	115.9 (2)	O4—C26—N9	123.75 (19)
C18—C13—C14	119.8 (2)	N10—C26—N9	107.08 (17)
C15—C14—C13	120.5 (2)	N9—C27—C28	111.25 (18)
C15—C14—H14	119.7	N9—C27—H27A	109.4
C13—C14—H14	119.7	C28—C27—H27A	109.4
C14—C15—C16	119.6 (2)	N9—C27—H27B	109.4
C14—C15—H15	120.2	C28—C27—H27B	109.4
C16—C15—H15	120.2	H27A—C27—H27B	108.0
C17—C16—C15	119.9 (2)	O3—C28—C27	106.35 (18)
C17—C16—S1	119.78 (16)	O3—C28—H28A	110.5
C15—C16—S1	120.32 (16)	C27—C28—H28A	110.5
C18—C17—C16	120.7 (2)	O3—C28—H28B	110.5
C18—C17—H17	119.6	C27—C28—H28B	110.5
C16—C17—H17	119.6	H28A—C28—H28B	108.7
C17—C18—C13	119.5 (2)	O3—C29—C30	124.4 (2)
C17—C18—H18	120.3	O3—C29—C34	115.19 (19)
C13—C18—H18	120.3	C30—C29—C34	120.3 (2)
N11—C19—C20	110.81 (15)	C29—C30—C31	119.4 (2)
N11—C19—C24	108.26 (15)	C29—C30—H30	120.3
C20—C19—C24	111.53 (16)	C31—C30—H30	120.3
N11—C19—H19	108.7	C32—C31—C30	118.5 (2)
C20—C19—H19	108.7	C32—C31—H31	120.7
C24—C19—H19	108.7	C30—C31—H31	120.7
C19—C20—C21	110.55 (16)	C33—C32—C31	123.3 (2)
C19—C20—H20A	109.5	C33—C32—F2	118.6 (3)
C21—C20—H20A	109.5	C31—C32—F2	118.0 (3)
C19—C20—H20B	109.5	C32—C33—C34	118.1 (3)
C21—C20—H20B	109.5	C32—C33—H33	121.0
H20A—C20—H20B	108.1	C34—C33—H33	121.0
C22—C21—C20	111.87 (17)	C33—C34—C29	120.3 (2)
C22—C21—H21A	109.2	C33—C34—H34	119.8
C20—C21—H21A	109.2	C29—C34—H34	119.8
C22—C21—H21B	109.2
O7—S1—N11—C19	−60.56 (16)	N10—C23—C24—C19	−72.4 (2)
O6—S1—N11—C19	170.97 (14)	C25—C23—C24—C19	178.57 (15)
C16—S1—N11—C19	55.41 (16)	C22—C23—C24—C19	54.9 (2)
C12—O8—C13—C18	2.9 (4)	C26—N9—C25—O5	−178.3 (2)
C12—O8—C13—C14	−176.9 (3)	C27—N9—C25—O5	12.4 (3)
O8—C13—C14—C15	178.8 (2)	C26—N9—C25—C23	3.5 (2)
C18—C13—C14—C15	−1.0 (4)	C27—N9—C25—C23	−165.77 (18)
C13—C14—C15—C16	−0.3 (4)	N10—C23—C25—O5	175.12 (19)
C14—C15—C16—C17	1.2 (3)	C22—C23—C25—O5	53.4 (3)
C14—C15—C16—S1	179.56 (19)	C24—C23—C25—O5	−69.1 (2)
O7—S1—C16—C17	−166.69 (16)	N10—C23—C25—N9	−6.72 (19)
O6—S1—C16—C17	−36.52 (19)	C22—C23—C25—N9	−128.47 (17)
N11—S1—C16—C17	76.62 (18)	C24—C23—C25—N9	109.10 (17)
O7—S1—C16—C15	14.9 (2)	C23—N10—C26—O4	173.8 (2)
O6—S1—C16—C15	145.07 (18)	C23—N10—C26—N9	−6.5 (2)
N11—S1—C16—C15	−101.79 (19)	C25—N9—C26—O4	−178.7 (2)
C15—C16—C17—C18	−0.9 (3)	C27—N9—C26—O4	−9.1 (3)
S1—C16—C17—C18	−179.27 (17)	C25—N9—C26—N10	1.6 (2)
C16—C17—C18—C13	−0.4 (3)	C27—N9—C26—N10	171.25 (17)
O8—C13—C18—C17	−178.5 (2)	C25—N9—C27—C28	92.0 (2)
C14—C13—C18—C17	1.3 (4)	C26—N9—C27—C28	−76.1 (2)
S1—N11—C19—C20	125.10 (15)	C29—O3—C28—C27	179.60 (18)
S1—N11—C19—C24	−112.29 (16)	N9—C27—C28—O3	−55.9 (2)
N11—C19—C20—C21	176.69 (16)	C28—O3—C29—C30	20.0 (3)
C24—C19—C20—C21	56.0 (2)	C28—O3—C29—C34	−162.7 (2)
C19—C20—C21—C22	−55.3 (2)	O3—C29—C30—C31	176.7 (2)
C20—C21—C22—C23	54.9 (2)	C34—C29—C30—C31	−0.4 (4)
C26—N10—C23—C25	8.2 (2)	C29—C30—C31—C32	0.3 (4)
C26—N10—C23—C22	129.10 (19)	C30—C31—C32—C33	−0.2 (5)
C26—N10—C23—C24	−105.47 (19)	C30—C31—C32—F2	−179.4 (3)
C21—C22—C23—N10	71.3 (2)	C31—C32—C33—C34	0.3 (5)
C21—C22—C23—C25	−174.89 (16)	F2—C32—C33—C34	179.4 (3)
C21—C22—C23—C24	−54.1 (2)	C32—C33—C34—C29	−0.4 (4)
N11—C19—C24—C23	−178.48 (15)	O3—C29—C34—C33	−176.9 (2)
C20—C19—C24—C23	−56.3 (2)	C30—C29—C34—C33	0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10···O5i	0.86	2.08	2.924 (2)	168.
N11—H11···O6ii	0.86	2.39	2.991 (3)	127.
C20—H20A···O4iii	0.97	2.51	3.377 (3)	148.
C31—H31···O4iv	0.93	2.48	3.327 (3)	152.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H10⋯O5i	0.86	2.08	2.924 (2)	168
N11—H11⋯O6ii	0.86	2.39	2.991 (3)	127
C20—H20A⋯O4iii	0.97	2.51	3.377 (3)	148
C31—H31⋯O4iv	0.93	2.48	3.327 (3)	152

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .