(E)-1-[2-(4-Fluoro-2-nitro­styr­yl)-1-phenyl­sulfonyl-1H-indol-3-yl]propan-1-one

Umadevi, M.; Saravanan, V.; Yamuna, R.; Mohanakrishnan, A.K.; Chakkaravarthi, G.

doi:10.1107/S1600536813030961

(E)-1-[2-(4-Fluoro-2-nitrostyryl)-1-phenylsulfonyl-1H-indol-3-yl]propan-1-one

M. Umadevi, V. Saravanan, R. Yamuna, A. K. Mohanakrishnan and G. Chakkaravarthi

In the title compound, C₂₅H₁₉FN₂O₅S, the substituted phenyl ring makes a dihedral angle of 12.26 (9)° with the indole ring system. The nitro group is twisted at an angle of 26.92 (8)° out of the plane of the ring to which it is attached. The molecular structure is stabilized by weak C—H

O hydrogen bonds. In the crystal, weak C—H

O, C—H

F and π–π [centroid–centroid distance = 3.6645 (11) Å] interactions link the molecules, forming a three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536813030961/bt6945sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536813030961/bt6945Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536813030961/bt6945Isup3.cml Supplementary material

CCDC reference: 971357

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.003 Å
R factor = 0.055
wR factor = 0.176
Data-to-parameter ratio = 26.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....         N2 Check
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -1.521
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          2
PLAT918_ALERT_3_C Reflection(s) # with I(obs) much smaller I(calc)          1 Check

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600       1275

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Indole derivatives are known to exhibit antimicrobial, antibiotic, analgesic, anticancer and anti-HIV (Pomarnacka & Kozlarska-Kedra, 2003; Srivastava et al., 2011) activities. In continuation of our studies on indole derivatives, we determined the crystal structure of the title compound (I). The geometric parameters of (I) (Fig. 1) are agree well with the reported structures (Chakkaravarthi et al., 2008; 2010).

Due to Thorpe-Ignold effect (Bassindale, 1984), bond angles around atom S1 show significant deviation from ideal tetrahedral value, with significant deviations in angles O1—S1—O2 [120.42 (8)°] and N1—S1—C1 [104.66 (7)°]. The phenyl ring (C1—C6) makes the dihedral angle of 85.05 (8)° with the indole ring system. The phenyl ring (C1—C6) and the benzene ring (C20—C25) are inclined at an angle of 12.26 (9)°. The nitro group is twisted at an angle of 26.92 (8)° with the attached benzene ring (C20—C25). The sum of the bond angles around N1 (358.26°) indicates the sp² hybridization of N1 atom (Beddoes et al., 1986).

The molecular structure is stabilized by weak intramolecular C—H···O hydrogen bonds (Table 1). The crystal structure exhibit weak intermolecular C—H···O, C—H···F (Table 1 & Fig. 2) and π···π [Cg4···Cg4ⁱ = 3.6645 (11) Å; (i) 1 - x, -1 - y, 2 - z; Cg4 is the centroid of the ring (C20—C25)] interactions.

Related literature top

For the biological activity of indole derivatives, see: Pomarnacka & Kozlarska-Kedra (2003); Srivastava et al. (2011). For related structures, see: Chakkaravarthi et al. (2008, 2010). For details of the configuration at the S atom, see: Bassindale (1984). For details of N-atom hybridization, see: Beddoes et al. (1986).

Experimental top

A solution of 1-(2-(bromomethyl)-1-(phenylsulfonyl)-1H-indol-3-yl) propan-1-one (5 g, 12.31 mmol) and triphenylphosphine (3.5 g, 13.54 mmol) in dry THF (100 ml) was refluxed for 6 h. After consumption of the starting material, the solvent was removed under vacuo and the solid was washed with diethyl ether to give the phosphonium salt. Then, the mixture of phosphonium salt (8 g, 11.97 mmol), 4-fluoro-2-nitrobenzaldehyde (2.24 g, 13.17 mmol) and K₂CO₃ (3.30 g, 23.95 mmol) in DCM (70 ml) was stirred at room temperature for 22 h. After completion of the reaction (monitored by TLC), it was diluted using DCM (30 ml), washed with water (2 x 100 ml) and dried (Na₂SO₄). Removal of solvent in vacuo followed by trituration of the crude product with MeOH (20 ml) afforded the title compound suitable for X-ray diffraction quality.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of the title compound, view onto the ac plane. Intermolecular hydrogen bonds are shown as dashed lines. H atoms not involving hydrogen bonding have been omitted.

(E)-1-[2-(4-Fluoro-2-nitrostyryl)-1-phenylsulfonyl-1H-indol-3-yl]propan-1-one top

Crystal data top

C₂₅H₁₉FN₂O₅S	Z = 2
M_r = 478.48	F(000) = 496
Triclinic, P1	D_x = 1.477 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2615 (3) Å	Cell parameters from 5619 reflections
b = 10.7624 (5) Å	θ = 2.1–31.1°
c = 13.2432 (6) Å	µ = 0.20 mm⁻¹
α = 68.606 (2)°	T = 295 K
β = 80.554 (3)°	Block, colourless
γ = 81.012 (2)°	0.30 × 0.24 × 0.20 mm
V = 1075.53 (8) Å³

Data collection top

Bruker APEXII diffractometer	8185 independent reflections
Radiation source: fine-focus sealed tube	5506 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω and ϕ scan	θ_max = 35.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.942, T_max = 0.961	k = −16→17
27388 measured reflections	l = −20→21

Refinement top

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.176	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.089P)² + 0.2703P] where P = (F_o² + 2F_c²)/3
8185 reflections	(Δ/σ)_max < 0.001
308 parameters	Δρ_max = 0.96 e Å⁻³
0 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

C₂₅H₁₉FN₂O₅S	γ = 81.012 (2)°
M_r = 478.48	V = 1075.53 (8) Å³
Triclinic, P1	Z = 2
a = 8.2615 (3) Å	Mo Kα radiation
b = 10.7624 (5) Å	µ = 0.20 mm⁻¹
c = 13.2432 (6) Å	T = 295 K
α = 68.606 (2)°	0.30 × 0.24 × 0.20 mm
β = 80.554 (3)°

Data collection top

Bruker APEXII diffractometer	8185 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5506 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.961	R_int = 0.028
27388 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.176	H-atom parameters constrained
S = 1.03	Δρ_max = 0.96 e Å⁻³
8185 reflections	Δρ_min = −0.61 e Å⁻³
308 parameters

Special details top

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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	−0.05337 (18)	0.17906 (15)	0.76350 (12)	0.0387 (3)
C2	−0.0663 (2)	0.06833 (18)	0.85866 (14)	0.0476 (4)
H2	0.0275	0.0203	0.8901	0.057*
C3	−0.2214 (2)	0.0306 (2)	0.90598 (16)	0.0563 (4)
H3	−0.2324	−0.0430	0.9702	0.068*
C4	−0.3602 (2)	0.1021 (2)	0.85825 (16)	0.0540 (4)
H4	−0.4641	0.0762	0.8907	0.065*
C5	−0.3457 (2)	0.2109 (2)	0.76326 (16)	0.0548 (4)
H5	−0.4397	0.2576	0.7314	0.066*
C6	−0.1920 (2)	0.25156 (19)	0.71465 (14)	0.0489 (4)
H6	−0.1817	0.3257	0.6507	0.059*
C7	0.1475 (2)	0.19323 (17)	0.50807 (12)	0.0439 (3)
C8	0.0691 (3)	0.3166 (2)	0.44803 (15)	0.0596 (5)
H8	0.0385	0.3851	0.4765	0.072*
C9	0.0389 (3)	0.3323 (2)	0.34425 (16)	0.0668 (6)
H9	−0.0130	0.4135	0.3020	0.080*
C10	0.0836 (3)	0.2308 (2)	0.30181 (15)	0.0637 (5)
H10	0.0627	0.2457	0.2312	0.076*
C11	0.1583 (2)	0.1080 (2)	0.36119 (13)	0.0544 (4)
H11	0.1858	0.0397	0.3322	0.065*
C12	0.1919 (2)	0.08841 (17)	0.46722 (12)	0.0429 (3)
C13	0.27195 (19)	−0.02364 (15)	0.54893 (12)	0.0403 (3)
C14	0.27322 (18)	0.01380 (14)	0.63737 (11)	0.0367 (3)
C15	0.3524 (3)	−0.14616 (18)	0.52664 (14)	0.0522 (4)
C16	0.4209 (3)	−0.26746 (18)	0.61156 (15)	0.0563 (4)
H16A	0.3365	−0.2957	0.6730	0.068*
H16B	0.5119	−0.2449	0.6373	0.068*
C17	0.4816 (4)	−0.3835 (2)	0.5708 (2)	0.0767 (7)
H17A	0.3896	−0.4137	0.5537	0.115*
H17B	0.5345	−0.4558	0.6265	0.115*
H17C	0.5589	−0.3542	0.5065	0.115*
C18	0.34816 (19)	−0.05675 (15)	0.73895 (11)	0.0380 (3)
H18	0.4365	−0.0220	0.7510	0.046*
C19	0.29602 (19)	−0.16804 (15)	0.81477 (11)	0.0380 (3)
H19	0.2011	−0.1976	0.8059	0.046*
C20	0.37971 (18)	−0.24690 (14)	0.91153 (11)	0.0360 (3)
C21	0.5492 (2)	−0.24341 (16)	0.90850 (14)	0.0454 (3)
H21	0.6053	−0.1874	0.8457	0.054*
C22	0.6361 (2)	−0.31934 (18)	0.99463 (15)	0.0510 (4)
H22	0.7478	−0.3125	0.9913	0.061*
C23	0.5542 (2)	−0.40558 (17)	1.08570 (15)	0.0511 (4)
C24	0.3899 (2)	−0.41643 (16)	1.09468 (13)	0.0462 (4)
H24	0.3370	−0.4760	1.1569	0.055*
C25	0.30441 (19)	−0.33571 (15)	1.00810 (11)	0.0384 (3)
N1	0.20107 (17)	0.14790 (13)	0.61298 (10)	0.0410 (3)
N2	0.12683 (19)	−0.34714 (16)	1.02366 (11)	0.0489 (3)
O1	0.12824 (18)	0.36656 (12)	0.64011 (11)	0.0580 (3)
O2	0.25410 (15)	0.17470 (13)	0.78405 (10)	0.0492 (3)
O3	0.3708 (3)	−0.1422 (2)	0.43278 (14)	0.1065 (8)
O4	0.03576 (17)	−0.25160 (16)	0.97436 (13)	0.0684 (4)
O5	0.0783 (2)	−0.45267 (19)	1.08539 (15)	0.0913 (6)
S1	0.14288 (5)	0.22764 (4)	0.70332 (3)	0.04104 (11)
F1	0.64046 (18)	−0.48260 (14)	1.16881 (11)	0.0778 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0383 (7)	0.0433 (7)	0.0372 (7)	−0.0005 (5)	−0.0030 (5)	−0.0194 (6)
C2	0.0446 (8)	0.0492 (9)	0.0453 (8)	−0.0023 (6)	−0.0044 (6)	−0.0135 (7)
C3	0.0536 (10)	0.0562 (10)	0.0553 (10)	−0.0114 (8)	0.0045 (8)	−0.0171 (8)
C4	0.0426 (8)	0.0676 (11)	0.0620 (11)	−0.0103 (8)	0.0031 (7)	−0.0366 (9)
C5	0.0401 (8)	0.0756 (12)	0.0585 (10)	0.0042 (8)	−0.0096 (7)	−0.0372 (10)
C6	0.0465 (9)	0.0570 (10)	0.0430 (8)	0.0034 (7)	−0.0073 (6)	−0.0199 (7)
C7	0.0439 (8)	0.0475 (8)	0.0315 (6)	−0.0027 (6)	−0.0015 (6)	−0.0055 (6)
C8	0.0646 (11)	0.0569 (11)	0.0416 (9)	0.0094 (9)	−0.0054 (8)	−0.0053 (8)
C9	0.0628 (12)	0.0732 (13)	0.0416 (9)	0.0056 (10)	−0.0100 (8)	0.0033 (9)
C10	0.0587 (11)	0.0875 (15)	0.0335 (8)	−0.0111 (10)	−0.0098 (7)	−0.0047 (9)
C11	0.0584 (10)	0.0704 (12)	0.0337 (7)	−0.0154 (9)	−0.0069 (7)	−0.0131 (7)
C12	0.0430 (8)	0.0509 (8)	0.0304 (6)	−0.0113 (6)	−0.0013 (5)	−0.0078 (6)
C13	0.0456 (8)	0.0412 (7)	0.0322 (6)	−0.0095 (6)	−0.0010 (5)	−0.0100 (5)
C14	0.0390 (7)	0.0370 (7)	0.0303 (6)	−0.0049 (5)	−0.0004 (5)	−0.0082 (5)
C15	0.0694 (11)	0.0485 (9)	0.0438 (8)	−0.0094 (8)	−0.0045 (8)	−0.0216 (7)
C16	0.0739 (12)	0.0455 (9)	0.0468 (9)	0.0002 (8)	0.0042 (8)	−0.0202 (7)
C17	0.1053 (19)	0.0522 (11)	0.0682 (13)	−0.0006 (11)	0.0154 (13)	−0.0298 (10)
C18	0.0422 (7)	0.0379 (7)	0.0326 (6)	−0.0020 (5)	−0.0038 (5)	−0.0118 (5)
C19	0.0397 (7)	0.0407 (7)	0.0315 (6)	−0.0033 (5)	−0.0026 (5)	−0.0110 (5)
C20	0.0412 (7)	0.0340 (6)	0.0318 (6)	−0.0024 (5)	−0.0033 (5)	−0.0116 (5)
C21	0.0423 (8)	0.0421 (8)	0.0453 (8)	−0.0035 (6)	−0.0041 (6)	−0.0085 (6)
C22	0.0444 (8)	0.0480 (9)	0.0570 (10)	−0.0009 (7)	−0.0135 (7)	−0.0127 (7)
C23	0.0628 (11)	0.0431 (8)	0.0458 (8)	0.0028 (7)	−0.0217 (8)	−0.0105 (7)
C24	0.0606 (10)	0.0419 (8)	0.0334 (7)	−0.0055 (7)	−0.0074 (6)	−0.0089 (6)
C25	0.0460 (8)	0.0367 (7)	0.0322 (6)	−0.0055 (5)	−0.0031 (5)	−0.0119 (5)
N1	0.0473 (7)	0.0399 (6)	0.0302 (5)	0.0019 (5)	−0.0018 (5)	−0.0093 (5)
N2	0.0490 (8)	0.0547 (8)	0.0382 (7)	−0.0129 (6)	0.0003 (6)	−0.0096 (6)
O1	0.0655 (8)	0.0389 (6)	0.0634 (8)	−0.0044 (5)	0.0000 (6)	−0.0142 (6)
O2	0.0431 (6)	0.0580 (7)	0.0523 (7)	−0.0025 (5)	−0.0092 (5)	−0.0258 (6)
O3	0.187 (2)	0.0818 (12)	0.0574 (9)	0.0227 (13)	−0.0319 (12)	−0.0396 (9)
O4	0.0455 (7)	0.0704 (9)	0.0690 (9)	−0.0035 (6)	−0.0025 (6)	−0.0031 (7)
O5	0.0707 (10)	0.0820 (11)	0.0877 (12)	−0.0339 (9)	−0.0065 (9)	0.0192 (9)
S1	0.0421 (2)	0.03958 (19)	0.0412 (2)	−0.00283 (14)	−0.00230 (14)	−0.01553 (15)
F1	0.0838 (9)	0.0747 (8)	0.0621 (7)	−0.0007 (7)	−0.0385 (7)	0.0009 (6)

Geometric parameters (Å, º) top

C1—C2	1.385 (2)	C15—O3	1.213 (2)
C1—C6	1.391 (2)	C15—C16	1.482 (3)
C1—S1	1.7532 (16)	C16—C17	1.520 (3)
C2—C3	1.383 (3)	C16—H16A	0.9700
C2—H2	0.9300	C16—H16B	0.9700
C3—C4	1.383 (3)	C17—H17A	0.9600
C3—H3	0.9300	C17—H17B	0.9600
C4—C5	1.374 (3)	C17—H17C	0.9600
C4—H4	0.9300	C18—C19	1.330 (2)
C5—C6	1.385 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.4678 (19)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.394 (2)	C20—C21	1.401 (2)
C7—C12	1.397 (2)	C20—C25	1.403 (2)
C7—N1	1.4155 (19)	C21—C22	1.375 (2)
C8—C9	1.382 (3)	C21—H21	0.9300
C8—H8	0.9300	C22—C23	1.373 (3)
C9—C10	1.379 (3)	C22—H22	0.9300
C9—H9	0.9300	C23—F1	1.3465 (19)
C10—C11	1.375 (3)	C23—C24	1.363 (3)
C10—H10	0.9300	C24—C25	1.384 (2)
C11—C12	1.410 (2)	C24—H24	0.9300
C11—H11	0.9300	C25—N2	1.466 (2)
C12—C13	1.448 (2)	N1—S1	1.6824 (13)
C13—C14	1.373 (2)	N2—O5	1.215 (2)
C13—C15	1.488 (2)	N2—O4	1.216 (2)
C14—N1	1.4131 (19)	O1—S1	1.4193 (13)
C14—C18	1.467 (2)	O2—S1	1.4235 (13)

C2—C1—C6	121.56 (16)	C17—C16—H16A	109.0
C2—C1—S1	118.92 (12)	C15—C16—H16B	109.0
C6—C1—S1	119.52 (13)	C17—C16—H16B	109.0
C3—C2—C1	118.70 (16)	H16A—C16—H16B	107.8
C3—C2—H2	120.7	C16—C17—H17A	109.5
C1—C2—H2	120.7	C16—C17—H17B	109.5
C2—C3—C4	120.28 (18)	H17A—C17—H17B	109.5
C2—C3—H3	119.9	C16—C17—H17C	109.5
C4—C3—H3	119.9	H17A—C17—H17C	109.5
C5—C4—C3	120.48 (17)	H17B—C17—H17C	109.5
C5—C4—H4	119.8	C19—C18—C14	123.25 (14)
C3—C4—H4	119.8	C19—C18—H18	118.4
C4—C5—C6	120.46 (17)	C14—C18—H18	118.4
C4—C5—H5	119.8	C18—C19—C20	123.78 (14)
C6—C5—H5	119.8	C18—C19—H19	118.1
C5—C6—C1	118.52 (17)	C20—C19—H19	118.1
C5—C6—H6	120.7	C21—C20—C25	115.36 (14)
C1—C6—H6	120.7	C21—C20—C19	119.86 (13)
C8—C7—C12	122.28 (16)	C25—C20—C19	124.64 (14)
C8—C7—N1	130.77 (17)	C22—C21—C20	122.68 (15)
C12—C7—N1	106.93 (13)	C22—C21—H21	118.7
C9—C8—C7	117.0 (2)	C20—C21—H21	118.7
C9—C8—H8	121.5	C23—C22—C21	118.50 (17)
C7—C8—H8	121.5	C23—C22—H22	120.8
C10—C9—C8	121.67 (19)	C21—C22—H22	120.8
C10—C9—H9	119.2	F1—C23—C24	119.04 (17)
C8—C9—H9	119.2	F1—C23—C22	118.45 (17)
C11—C10—C9	121.72 (18)	C24—C23—C22	122.51 (16)
C11—C10—H10	119.1	C23—C24—C25	117.75 (15)
C9—C10—H10	119.1	C23—C24—H24	121.1
C10—C11—C12	118.23 (19)	C25—C24—H24	121.1
C10—C11—H11	120.9	C24—C25—C20	123.15 (15)
C12—C11—H11	120.9	C24—C25—N2	115.60 (14)
C7—C12—C11	119.09 (16)	C20—C25—N2	121.24 (13)
C7—C12—C13	108.19 (13)	C14—N1—C7	108.72 (12)
C11—C12—C13	132.70 (17)	C14—N1—S1	125.70 (10)
C14—C13—C12	107.60 (14)	C7—N1—S1	123.84 (11)
C14—C13—C15	129.90 (15)	O5—N2—O4	123.33 (17)
C12—C13—C15	122.08 (14)	O5—N2—C25	117.83 (16)
C13—C14—N1	108.51 (13)	O4—N2—C25	118.84 (14)
C13—C14—C18	130.55 (14)	O1—S1—O2	120.42 (8)
N1—C14—C18	120.63 (13)	O1—S1—N1	105.64 (7)
O3—C15—C16	119.04 (18)	O2—S1—N1	106.91 (7)
O3—C15—C13	117.57 (18)	O1—S1—C1	109.25 (8)
C16—C15—C13	123.24 (14)	O2—S1—C1	108.80 (7)
C15—C16—C17	113.04 (17)	N1—S1—C1	104.66 (7)
C15—C16—H16A	109.0

C6—C1—C2—C3	−0.6 (3)	C25—C20—C21—C22	−1.3 (2)
S1—C1—C2—C3	179.82 (14)	C19—C20—C21—C22	−177.11 (15)
C1—C2—C3—C4	0.5 (3)	C20—C21—C22—C23	2.4 (3)
C2—C3—C4—C5	0.2 (3)	C21—C22—C23—F1	178.20 (16)
C3—C4—C5—C6	−0.7 (3)	C21—C22—C23—C24	−1.5 (3)
C4—C5—C6—C1	0.6 (3)	F1—C23—C24—C25	179.81 (15)
C2—C1—C6—C5	0.0 (2)	C22—C23—C24—C25	−0.5 (3)
S1—C1—C6—C5	179.63 (13)	C23—C24—C25—C20	1.7 (2)
C12—C7—C8—C9	−1.0 (3)	C23—C24—C25—N2	−177.55 (15)
N1—C7—C8—C9	177.10 (18)	C21—C20—C25—C24	−0.8 (2)
C7—C8—C9—C10	0.2 (3)	C19—C20—C25—C24	174.77 (14)
C8—C9—C10—C11	1.0 (3)	C21—C20—C25—N2	178.40 (14)
C9—C10—C11—C12	−1.3 (3)	C19—C20—C25—N2	−6.0 (2)
C8—C7—C12—C11	0.7 (3)	C13—C14—N1—C7	2.37 (17)
N1—C7—C12—C11	−177.79 (14)	C18—C14—N1—C7	176.59 (13)
C8—C7—C12—C13	179.31 (17)	C13—C14—N1—S1	167.73 (11)
N1—C7—C12—C13	0.79 (17)	C18—C14—N1—S1	−18.1 (2)
C10—C11—C12—C7	0.4 (3)	C8—C7—N1—C14	179.72 (18)
C10—C11—C12—C13	−177.72 (17)	C12—C7—N1—C14	−1.92 (17)
C7—C12—C13—C14	0.66 (17)	C8—C7—N1—S1	14.0 (3)
C11—C12—C13—C14	178.97 (17)	C12—C7—N1—S1	−167.62 (11)
C7—C12—C13—C15	−172.65 (15)	C24—C25—N2—O5	−27.0 (2)
C11—C12—C13—C15	5.7 (3)	C20—C25—N2—O5	153.67 (18)
C12—C13—C14—N1	−1.84 (16)	C24—C25—N2—O4	153.21 (16)
C15—C13—C14—N1	170.76 (16)	C20—C25—N2—O4	−26.1 (2)
C12—C13—C14—C18	−175.29 (15)	C14—N1—S1—O1	161.77 (13)
C15—C13—C14—C18	−2.7 (3)	C7—N1—S1—O1	−34.98 (15)
C14—C13—C15—O3	−161.0 (2)	C14—N1—S1—O2	32.38 (15)
C12—C13—C15—O3	10.7 (3)	C7—N1—S1—O2	−164.37 (13)
C14—C13—C15—C16	14.4 (3)	C14—N1—S1—C1	−82.94 (14)
C12—C13—C15—C16	−173.90 (17)	C7—N1—S1—C1	80.31 (14)
O3—C15—C16—C17	−10.1 (3)	C2—C1—S1—O1	−154.93 (13)
C13—C15—C16—C17	174.49 (19)	C6—C1—S1—O1	25.46 (15)
C13—C14—C18—C19	−67.9 (2)	C2—C1—S1—O2	−21.66 (15)
N1—C14—C18—C19	119.31 (17)	C6—C1—S1—O2	158.73 (12)
C14—C18—C19—C20	173.75 (13)	C2—C1—S1—N1	92.33 (13)
C18—C19—C20—C21	−26.3 (2)	C6—C1—S1—N1	−87.28 (13)
C18—C19—C20—C25	158.25 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1	0.93	2.33	2.913 (3)	120
C11—H11···O3	0.93	2.40	2.905 (3)	114
C16—H16A···F1ⁱ	0.97	2.54	3.192 (2)	124
C22—H22···O4ⁱⁱ	0.93	2.52	3.438 (2)	170

Symmetry codes: (i) −x+1, −y−1, −z+2; (ii) x+1, y, z.