[3-({(E)-2-[(4-Fluorophenyl)carbamo-thioyl]hydrazinylidene}methyl)-4-hy-droxy-benzyl]methyl-triphenyl-phos-phonium chloride.

The cation in the title salt, C(33)H(28)FN(3)OPS(+)·Cl(-), is highly twisted with the phospho-nium group occupying a position almost normal to the central hydroxyl-benzene ring [P-C-C-C tosrsion angle = -100.9 (3)°], and with the hydrazone substituent twisted out of the plane [C-C-C-N torsion angle = 13.1 (4)°]. The fluoro-benzene ring is twisted out of the plane of the adjacent thio-urea residue, forming a dihedral angle of 51.69 (10)°. The configuration about the C=N bond [1.281 (4) Å] is E, the O-H and N-H hydrogen atoms are syn, and in the thio-urea residue, the N-H hydrogen atoms are anti, allowing for the formation of an intra-molecular N-H⋯N hydrogen bond. In the crystal, dimeric aggregates mediated by N-H⋯S bonds are formed, which are linked to the Cl(-) anions by O-H⋯Cl hydrogen bonds. The four-component aggregates are linked into a three-dimensional structure by C-H⋯Cl inter-actions.

Related literature

For the crystal structure of the related compound salicyl­aldehyde 4-phenyl­thio­semicarbazone, see: Rubčić et al. (2008 ▶). For the anti-tumour, anti-viral and anti-fungal activity of thio­semicarbazones, see: Kalinowski et al. (2009 ▶); Beraldo & Gambino (2004 ▶). For the biological properties of triphenyl­phospho­nium-containing Schiff bases, see: Shahabadi et al. (2010 ▶).

Experimental

Crystal data

C33H28FN3OPS+·Cl−

M = 600.06

Monoclinic,

a = 17.5495 (6) Å

b = 9.4617 (3) Å

c = 19.0569 (6) Å

β = 107.298 (4)°

V = 3021.24 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 100 K

0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.919, T max = 0.945

12024 measured reflections

6178 independent reflections

4374 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.154

S = 1.04

6178 reflections

382 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.62 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) general, I. DOI: 10.1107/S1600536811047945/hg5137sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047945/hg5137Isup2.hkl

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

C33H28FN3OPS+·Cl−	F(000) = 1248
Mr = 600.06	Dx = 1.319 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3679 reflections
a = 17.5495 (6) Å	θ = 2.4–29.2°
b = 9.4617 (3) Å	µ = 0.29 mm−1
c = 19.0569 (6) Å	T = 100 K
β = 107.298 (4)°	Prism, yellow
V = 3021.24 (17) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Agilent SuperNova Dual diffractometer with Atlas detector	6178 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4374 reflections with I > 2σ(I)
Mirror	Rint = 0.040
Detector resolution: 10.4041 pixels mm-1	θmax = 26.5°, θmin = 2.4°
ω scan	h = −17→22
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→9
Tmin = 0.919, Tmax = 0.945	l = −23→16
12024 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0639P)2 + 2.4147P] where P = (Fo2 + 2Fc2)/3
6178 reflections	(Δ/σ)max = 0.001
382 parameters	Δρmax = 0.62 e Å−3
3 restraints	Δρmin = −0.38 e Å−3

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
Cl1	0.91349 (4)	0.62474 (8)	0.85886 (4)	0.02368 (19)
P1	0.83503 (5)	1.15927 (8)	0.50731 (4)	0.0200 (2)
S1	0.48397 (5)	0.43111 (9)	0.38203 (4)	0.0283 (2)
F1	0.58227 (13)	0.3645 (3)	0.08217 (11)	0.0512 (6)
O1	0.78340 (13)	0.6681 (2)	0.71688 (12)	0.0280 (5)
N1	0.67395 (15)	0.6310 (3)	0.49955 (14)	0.0253 (6)
N2	0.60362 (15)	0.5553 (3)	0.47947 (14)	0.0262 (6)
N3	0.61878 (16)	0.5438 (3)	0.36568 (14)	0.0276 (6)
C1	0.74010 (17)	1.1072 (3)	0.44749 (15)	0.0212 (6)
C2	0.66882 (19)	1.1318 (4)	0.46326 (18)	0.0316 (8)
H2A	0.6687	1.1812	0.5066	0.038*
C3	0.5978 (2)	1.0833 (4)	0.41479 (19)	0.0386 (9)
H3A	0.5487	1.0983	0.4253	0.046*
C4	0.5985 (2)	1.0125 (4)	0.35068 (19)	0.0368 (8)
H4	0.5501	0.9769	0.3185	0.044*
C5	0.66894 (19)	0.9939 (3)	0.33374 (18)	0.0301 (7)
H5	0.6688	0.9491	0.2891	0.036*
C6	0.73978 (19)	1.0410 (3)	0.38218 (17)	0.0266 (7)
H6	0.7885	1.0280	0.3708	0.032*
C7	0.87455 (18)	1.2911 (3)	0.46083 (16)	0.0245 (7)
C8	0.8314 (2)	1.4157 (4)	0.4393 (3)	0.0535 (12)
H8	0.7814	1.4273	0.4482	0.064*
C9	0.8606 (2)	1.5209 (4)	0.4055 (3)	0.0553 (12)
H9	0.8313	1.6061	0.3919	0.066*
C10	0.9327 (2)	1.5034 (4)	0.39112 (18)	0.0351 (8)
H10	0.9522	1.5757	0.3664	0.042*
C11	0.9762 (2)	1.3819 (4)	0.4124 (2)	0.0373 (9)
H11	1.0258	1.3699	0.4025	0.045*
C12	0.9474 (2)	1.2765 (3)	0.4485 (2)	0.0352 (8)
H12	0.9782	1.1937	0.4649	0.042*
C13	0.82929 (18)	1.2290 (3)	0.59315 (17)	0.0247 (7)
C14	0.8756 (2)	1.3467 (4)	0.62295 (19)	0.0340 (8)
H14	0.9023	1.3982	0.5945	0.041*
C15	0.8824 (2)	1.3879 (4)	0.6947 (2)	0.0420 (9)
H15	0.9143	1.4672	0.7153	0.050*
C16	0.8437 (2)	1.3158 (4)	0.7353 (2)	0.0427 (9)
H16	0.8484	1.3460	0.7839	0.051*
C17	0.7978 (2)	1.1993 (4)	0.70702 (19)	0.0372 (9)
H17	0.7711	1.1495	0.7362	0.045*
C18	0.7904 (2)	1.1543 (4)	0.63557 (18)	0.0311 (8)
H18	0.7591	1.0736	0.6159	0.037*
C19	0.89916 (17)	1.0055 (3)	0.52567 (15)	0.0187 (6)
H19A	0.8972	0.9582	0.4788	0.022*
H19B	0.9549	1.0350	0.5499	0.022*
C20	0.87243 (17)	0.9036 (3)	0.57481 (15)	0.0202 (6)
C21	0.91367 (18)	0.8996 (3)	0.64994 (16)	0.0229 (7)
H21	0.9612	0.9532	0.6684	0.027*
C22	0.88599 (18)	0.8185 (3)	0.69762 (16)	0.0241 (7)
H22	0.9151	0.8154	0.7483	0.029*
C23	0.81585 (18)	0.7415 (3)	0.67172 (16)	0.0213 (6)
C24	0.77585 (17)	0.7385 (3)	0.59589 (16)	0.0207 (6)
C25	0.80530 (17)	0.8198 (3)	0.54838 (16)	0.0205 (6)
H25	0.7788	0.8175	0.4971	0.025*
C26	0.70392 (18)	0.6542 (3)	0.56854 (17)	0.0242 (7)
H26	0.6788	0.6159	0.6021	0.029*
C27	0.57265 (18)	0.5127 (3)	0.40903 (16)	0.0244 (7)
C28	0.60814 (18)	0.4968 (4)	0.29226 (16)	0.0272 (7)
C29	0.6181 (2)	0.5918 (4)	0.24096 (19)	0.0366 (8)
H29	0.6300	0.6879	0.2542	0.044*
C30	0.6108 (2)	0.5470 (4)	0.1695 (2)	0.0392 (9)
H30	0.6181	0.6110	0.1337	0.047*
C31	0.59293 (19)	0.4090 (4)	0.15287 (18)	0.0344 (8)
C32	0.5849 (2)	0.3102 (4)	0.20287 (19)	0.0355 (8)
H32	0.5738	0.2140	0.1894	0.043*
C33	0.59363 (19)	0.3568 (3)	0.27397 (17)	0.0292 (7)
H33	0.5895	0.2911	0.3104	0.035*
H1	0.8166 (17)	0.658 (4)	0.7584 (10)	0.044 (11)*
H2	0.576 (2)	0.541 (4)	0.5103 (18)	0.055 (12)*
H3	0.6576 (14)	0.604 (3)	0.3836 (17)	0.033 (10)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0248 (4)	0.0288 (4)	0.0148 (3)	−0.0007 (3)	0.0017 (3)	0.0035 (3)
P1	0.0206 (4)	0.0245 (4)	0.0136 (4)	−0.0001 (3)	0.0030 (3)	0.0014 (3)
S1	0.0221 (4)	0.0395 (5)	0.0211 (4)	−0.0075 (4)	0.0031 (3)	−0.0067 (3)
F1	0.0479 (13)	0.0864 (17)	0.0230 (11)	−0.0020 (12)	0.0162 (10)	−0.0122 (11)
O1	0.0261 (12)	0.0405 (13)	0.0144 (11)	−0.0072 (10)	0.0014 (10)	0.0073 (10)
N1	0.0207 (13)	0.0324 (15)	0.0190 (13)	−0.0064 (12)	0.0002 (11)	−0.0023 (11)
N2	0.0196 (13)	0.0397 (16)	0.0166 (14)	−0.0095 (12)	0.0011 (11)	−0.0033 (11)
N3	0.0259 (15)	0.0371 (16)	0.0173 (14)	−0.0111 (13)	0.0024 (12)	−0.0043 (12)
C1	0.0221 (15)	0.0267 (16)	0.0127 (14)	0.0000 (13)	0.0021 (12)	0.0062 (12)
C2	0.0315 (18)	0.044 (2)	0.0186 (16)	−0.0004 (16)	0.0064 (14)	0.0002 (14)
C3	0.0254 (18)	0.060 (2)	0.0289 (19)	−0.0069 (17)	0.0061 (15)	−0.0011 (17)
C4	0.0273 (18)	0.054 (2)	0.0244 (18)	−0.0106 (17)	0.0003 (15)	0.0022 (16)
C5	0.0314 (18)	0.0347 (18)	0.0204 (16)	0.0019 (15)	0.0017 (14)	−0.0030 (14)
C6	0.0241 (16)	0.0345 (18)	0.0205 (16)	−0.0005 (14)	0.0055 (14)	−0.0009 (13)
C7	0.0245 (16)	0.0286 (17)	0.0188 (16)	−0.0016 (14)	0.0037 (13)	0.0038 (13)
C8	0.032 (2)	0.053 (2)	0.079 (3)	0.0109 (19)	0.022 (2)	0.032 (2)
C9	0.039 (2)	0.049 (2)	0.078 (3)	0.013 (2)	0.018 (2)	0.037 (2)
C10	0.040 (2)	0.037 (2)	0.0269 (18)	−0.0071 (17)	0.0080 (16)	0.0106 (15)
C11	0.047 (2)	0.0324 (19)	0.043 (2)	0.0008 (17)	0.0297 (19)	0.0060 (16)
C12	0.045 (2)	0.0244 (17)	0.043 (2)	0.0091 (16)	0.0237 (18)	0.0107 (15)
C13	0.0281 (17)	0.0258 (16)	0.0199 (16)	0.0023 (14)	0.0067 (14)	−0.0028 (13)
C14	0.0306 (18)	0.0364 (19)	0.036 (2)	−0.0020 (16)	0.0113 (16)	−0.0081 (15)
C15	0.0318 (19)	0.049 (2)	0.042 (2)	0.0003 (18)	0.0047 (17)	−0.0235 (18)
C16	0.044 (2)	0.052 (2)	0.029 (2)	0.0047 (19)	0.0053 (18)	−0.0166 (17)
C17	0.035 (2)	0.052 (2)	0.0255 (19)	0.0059 (18)	0.0097 (16)	−0.0017 (16)
C18	0.0321 (18)	0.0364 (19)	0.0235 (17)	0.0009 (15)	0.0063 (15)	−0.0031 (14)
C19	0.0172 (14)	0.0256 (15)	0.0120 (14)	−0.0004 (12)	0.0023 (12)	−0.0010 (12)
C20	0.0233 (15)	0.0217 (15)	0.0139 (14)	0.0032 (13)	0.0030 (12)	0.0010 (12)
C21	0.0200 (15)	0.0272 (16)	0.0160 (15)	−0.0027 (13)	−0.0033 (12)	−0.0003 (12)
C22	0.0264 (16)	0.0315 (17)	0.0103 (14)	−0.0028 (14)	−0.0010 (13)	0.0006 (12)
C23	0.0216 (15)	0.0254 (16)	0.0163 (15)	−0.0026 (13)	0.0048 (12)	0.0032 (12)
C24	0.0198 (15)	0.0254 (16)	0.0152 (14)	0.0010 (13)	0.0025 (12)	0.0010 (12)
C25	0.0220 (15)	0.0251 (16)	0.0121 (14)	0.0015 (13)	0.0015 (12)	−0.0019 (12)
C26	0.0222 (16)	0.0312 (17)	0.0184 (16)	−0.0036 (13)	0.0046 (13)	−0.0001 (13)
C27	0.0243 (16)	0.0271 (17)	0.0186 (15)	0.0005 (14)	0.0016 (13)	−0.0009 (13)
C28	0.0229 (16)	0.0398 (19)	0.0176 (16)	−0.0025 (15)	0.0037 (13)	−0.0017 (14)
C29	0.041 (2)	0.039 (2)	0.0296 (19)	−0.0111 (17)	0.0116 (16)	−0.0011 (15)
C30	0.041 (2)	0.051 (2)	0.0283 (19)	−0.0029 (18)	0.0139 (17)	0.0076 (17)
C31	0.0265 (17)	0.062 (2)	0.0174 (16)	0.0049 (17)	0.0099 (14)	−0.0044 (16)
C32	0.036 (2)	0.044 (2)	0.0276 (19)	0.0017 (17)	0.0125 (16)	−0.0088 (16)
C33	0.0315 (18)	0.0339 (19)	0.0219 (17)	0.0078 (15)	0.0076 (14)	0.0035 (14)

P1—C1	1.786 (3)	C12—H12	0.9500
P1—C7	1.785 (3)	C13—C18	1.396 (4)
P1—C13	1.794 (3)	C13—C14	1.395 (4)
P1—C19	1.808 (3)	C14—C15	1.392 (5)
S1—C27	1.675 (3)	C14—H14	0.9500
F1—C31	1.370 (4)	C15—C16	1.355 (5)
O1—C23	1.356 (3)	C15—H15	0.9500
O1—H1	0.837 (10)	C16—C17	1.378 (5)
N1—C26	1.281 (4)	C16—H16	0.9500
N1—N2	1.379 (3)	C17—C18	1.395 (4)
N2—C27	1.351 (4)	C17—H17	0.9500
N2—H2	0.881 (10)	C18—H18	0.9500
N3—C27	1.350 (4)	C19—C20	1.513 (4)
N3—C28	1.427 (4)	C19—H19A	0.9900
N3—H3	0.874 (10)	C19—H19B	0.9900
C1—C2	1.390 (4)	C20—C25	1.385 (4)
C1—C6	1.392 (4)	C20—C21	1.400 (4)
C2—C3	1.391 (5)	C21—C22	1.383 (4)
C2—H2A	0.9500	C21—H21	0.9500
C3—C4	1.397 (5)	C22—C23	1.388 (4)
C3—H3A	0.9500	C22—H22	0.9500
C4—C5	1.379 (5)	C23—C24	1.407 (4)
C4—H4	0.9500	C24—C25	1.399 (4)
C5—C6	1.383 (4)	C24—C26	1.453 (4)
C5—H5	0.9500	C25—H25	0.9500
C6—H6	0.9500	C26—H26	0.9500
C7—C12	1.373 (4)	C28—C33	1.374 (5)
C7—C8	1.394 (5)	C28—C29	1.377 (4)
C8—C9	1.365 (5)	C29—C30	1.394 (5)
C8—H8	0.9500	C29—H29	0.9500
C9—C10	1.383 (5)	C30—C31	1.358 (5)
C9—H9	0.9500	C30—H30	0.9500
C10—C11	1.373 (5)	C31—C32	1.372 (5)
C10—H10	0.9500	C32—C33	1.389 (4)
C11—C12	1.390 (4)	C32—H32	0.9500
C11—H11	0.9500	C33—H33	0.9500
C1—P1—C7	107.60 (14)	C14—C15—H15	119.7
C1—P1—C13	112.88 (14)	C15—C16—C17	120.9 (3)
C7—P1—C13	109.30 (15)	C15—C16—H16	119.6
C1—P1—C19	108.09 (14)	C17—C16—H16	119.6
C7—P1—C19	110.30 (14)	C16—C17—C18	120.0 (3)
C13—P1—C19	108.65 (14)	C16—C17—H17	120.0
C23—O1—H1	111 (3)	C18—C17—H17	120.0
C26—N1—N2	115.7 (2)	C13—C18—C17	119.4 (3)
C27—N2—N1	119.5 (2)	C13—C18—H18	120.3
C27—N2—H2	119 (3)	C17—C18—H18	120.3
N1—N2—H2	122 (3)	C20—C19—P1	110.05 (19)
C27—N3—C28	127.2 (3)	C20—C19—H19A	109.7
C27—N3—H3	116 (2)	P1—C19—H19A	109.7
C28—N3—H3	116 (2)	C20—C19—H19B	109.7
C2—C1—C6	120.3 (3)	P1—C19—H19B	109.7
C2—C1—P1	123.0 (2)	H19A—C19—H19B	108.2
C6—C1—P1	116.7 (2)	C25—C20—C21	118.8 (3)
C3—C2—C1	119.2 (3)	C25—C20—C19	121.8 (3)
C3—C2—H2A	120.4	C21—C20—C19	119.3 (3)
C1—C2—H2A	120.4	C22—C21—C20	120.7 (3)
C2—C3—C4	120.0 (3)	C22—C21—H21	119.6
C2—C3—H3A	120.0	C20—C21—H21	119.6
C4—C3—H3A	120.0	C21—C22—C23	120.3 (3)
C5—C4—C3	120.5 (3)	C21—C22—H22	119.8
C5—C4—H4	119.7	C23—C22—H22	119.8
C3—C4—H4	119.7	O1—C23—C22	122.6 (3)
C4—C5—C6	119.5 (3)	O1—C23—C24	117.8 (3)
C4—C5—H5	120.2	C22—C23—C24	119.6 (3)
C6—C5—H5	120.2	C25—C24—C23	119.1 (3)
C5—C6—C1	120.4 (3)	C25—C24—C26	121.2 (3)
C5—C6—H6	119.8	C23—C24—C26	119.6 (3)
C1—C6—H6	119.8	C20—C25—C24	121.2 (3)
C12—C7—C8	119.1 (3)	C20—C25—H25	119.4
C12—C7—P1	122.2 (2)	C24—C25—H25	119.4
C8—C7—P1	118.6 (2)	N1—C26—C24	120.7 (3)
C9—C8—C7	120.6 (3)	N1—C26—H26	119.7
C9—C8—H8	119.7	C24—C26—H26	119.7
C7—C8—H8	119.7	N3—C27—N2	113.9 (3)
C8—C9—C10	120.0 (4)	N3—C27—S1	125.7 (2)
C8—C9—H9	120.0	N2—C27—S1	120.3 (2)
C10—C9—H9	120.0	C33—C28—C29	120.2 (3)
C11—C10—C9	120.2 (3)	C33—C28—N3	120.7 (3)
C11—C10—H10	119.9	C29—C28—N3	119.0 (3)
C9—C10—H10	119.9	C28—C29—C30	120.0 (3)
C10—C11—C12	119.6 (3)	C28—C29—H29	120.0
C10—C11—H11	120.2	C30—C29—H29	120.0
C12—C11—H11	120.2	C31—C30—C29	117.9 (3)
C7—C12—C11	120.4 (3)	C31—C30—H30	121.0
C7—C12—H12	119.8	C29—C30—H30	121.0
C11—C12—H12	119.8	C30—C31—F1	118.7 (3)
C18—C13—C14	119.6 (3)	C30—C31—C32	123.8 (3)
C18—C13—P1	120.8 (2)	F1—C31—C32	117.5 (3)
C14—C13—P1	118.7 (2)	C31—C32—C33	117.2 (3)
C15—C14—C13	119.5 (3)	C31—C32—H32	121.4
C15—C14—H14	120.2	C33—C32—H32	121.4
C13—C14—H14	120.2	C28—C33—C32	120.8 (3)
C16—C15—C14	120.6 (3)	C28—C33—H33	119.6
C16—C15—H15	119.7	C32—C33—H33	119.6
C26—N1—N2—C27	−172.7 (3)	C14—C13—C18—C17	0.6 (5)
C7—P1—C1—C2	−114.6 (3)	P1—C13—C18—C17	169.7 (3)
C13—P1—C1—C2	6.1 (3)	C16—C17—C18—C13	−0.5 (5)
C19—P1—C1—C2	126.3 (3)	C1—P1—C19—C20	−71.1 (2)
C7—P1—C1—C6	64.5 (3)	C7—P1—C19—C20	171.5 (2)
C13—P1—C1—C6	−174.8 (2)	C13—P1—C19—C20	51.7 (2)
C19—P1—C1—C6	−54.6 (3)	P1—C19—C20—C25	75.2 (3)
C6—C1—C2—C3	3.2 (5)	P1—C19—C20—C21	−100.9 (3)
P1—C1—C2—C3	−177.8 (3)	C25—C20—C21—C22	−2.9 (4)
C1—C2—C3—C4	−0.9 (5)	C19—C20—C21—C22	173.3 (3)
C2—C3—C4—C5	−2.0 (6)	C20—C21—C22—C23	−1.1 (5)
C3—C4—C5—C6	2.6 (5)	C21—C22—C23—O1	−175.4 (3)
C4—C5—C6—C1	−0.3 (5)	C21—C22—C23—C24	4.4 (4)
C2—C1—C6—C5	−2.6 (5)	O1—C23—C24—C25	176.3 (3)
P1—C1—C6—C5	178.2 (2)	C22—C23—C24—C25	−3.5 (4)
C1—P1—C7—C12	−123.2 (3)	O1—C23—C24—C26	−2.2 (4)
C13—P1—C7—C12	113.9 (3)	C22—C23—C24—C26	178.0 (3)
C19—P1—C7—C12	−5.5 (3)	C21—C20—C25—C24	3.8 (4)
C1—P1—C7—C8	59.7 (3)	C19—C20—C25—C24	−172.4 (3)
C13—P1—C7—C8	−63.2 (3)	C23—C24—C25—C20	−0.6 (4)
C19—P1—C7—C8	177.4 (3)	C26—C24—C25—C20	177.9 (3)
C12—C7—C8—C9	0.9 (6)	N2—N1—C26—C24	−177.1 (3)
P1—C7—C8—C9	178.1 (4)	C25—C24—C26—N1	13.1 (4)
C7—C8—C9—C10	1.2 (7)	C23—C24—C26—N1	−168.4 (3)
C8—C9—C10—C11	−1.6 (7)	C28—N3—C27—N2	170.9 (3)
C9—C10—C11—C12	−0.1 (6)	C28—N3—C27—S1	−9.9 (5)
C8—C7—C12—C11	−2.6 (6)	N1—N2—C27—N3	3.7 (4)
P1—C7—C12—C11	−179.7 (3)	N1—N2—C27—S1	−175.5 (2)
C10—C11—C12—C7	2.2 (6)	C27—N3—C28—C33	−47.5 (5)
C1—P1—C13—C18	51.5 (3)	C27—N3—C28—C29	137.0 (3)
C7—P1—C13—C18	171.2 (3)	C33—C28—C29—C30	2.2 (5)
C19—P1—C13—C18	−68.4 (3)	N3—C28—C29—C30	177.7 (3)
C1—P1—C13—C14	−139.3 (3)	C28—C29—C30—C31	0.7 (5)
C7—P1—C13—C14	−19.6 (3)	C29—C30—C31—F1	177.3 (3)
C19—P1—C13—C14	100.8 (3)	C29—C30—C31—C32	−2.8 (6)
C18—C13—C14—C15	0.0 (5)	C30—C31—C32—C33	1.8 (5)
P1—C13—C14—C15	−169.3 (3)	F1—C31—C32—C33	−178.3 (3)
C13—C14—C15—C16	−0.8 (5)	C29—C28—C33—C32	−3.2 (5)
C14—C15—C16—C17	0.8 (6)	N3—C28—C33—C32	−178.6 (3)
C15—C16—C17—C18	−0.2 (6)	C31—C32—C33—C28	1.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N1	0.87 (1)	2.16 (3)	2.580 (4)	109 (3)
O1—H1···Cl1	0.84 (1)	2.17 (1)	3.005 (2)	173 (4)
N2—H2···S1i	0.88 (1)	2.58 (2)	3.429 (3)	162 (3)
C6—H6···Cl1ii	0.95	2.69	3.572 (3)	154
C19—H19a···Cl1ii	0.99	2.51	3.488 (3)	168
C19—H19b···Cl1iii	0.99	2.59	3.553 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N1	0.87 (1)	2.16 (3)	2.580 (4)	109 (3)
O1—H1⋯Cl1	0.84 (1)	2.17 (1)	3.005 (2)	173 (4)
N2—H2⋯S1i	0.88 (1)	2.58 (2)	3.429 (3)	162 (3)
C6—H6⋯Cl1ii	0.95	2.69	3.572 (3)	154
C19—H19a⋯Cl1ii	0.99	2.51	3.488 (3)	168
C19—H19b⋯Cl1iii	0.99	2.59	3.553 (3)	165

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