1,3,5-Tri(iodoethynyl)-2,4,6-trifluorobenzene: halogen-bonded frameworks and NMR spectroscopic analysis

Szell, P.M.J.; Gabidullin, B.; Bryce, D.L.

doi:10.1107/S2052520617000944

1,3,5-Tri(iodoethynyl)-2,4,6-trifluorobenzene: halogen-bonded frameworks and NMR spectroscopic analysis

P. M. J. Szell, B. Gabidullin and D. L. Bryce

Halogen bonding is the non-covalent interaction between the region of positive electrostatic potential associated with a covalently bonded halogen atom, named the σ-hole, and a Lewis base. Single-crystal X-ray diffraction structures are reported for a series of seven halogen-bonded cocrystals featuring 1,3,5-tris(iodoethynyl)-2,4,6-trifluorobenzene (1) as the halogen-bond donor, and bromide ions (as ammonium or phosphonium salts) as the halogen-bond acceptors: (1)·MePh₃PBr, (1)·EtPh₃PBr, (1)·acetonyl-Ph₃PBr, (1)·Ph₄PBr, (1)·[bis(4-fluorophenyl)methyl]triphenylphosphonium bromide, and two new polymorphs of (1)·Et₃BuNBr. The cocrystals all feature moderately strong iodine–bromide halogen bonds. The crystal structure of pure [bis(4-fluorophenyl)methyl]triphenylphosphonium bromide is also reported. The results of a crystal engineering strategy of varying the size of the counter-cation are explored, and the features of the resulting framework materials are discussed. Given the potential utility of (1) in future crystal engineering applications, detailed NMR analyses (in solution and in the solid state) of this halogen-bond donor are also presented. In solution, complex ¹³C and ¹⁹F multiplets are explained by considering the delicate interplay between various J couplings and subtle isotope shifts. In the solid state, the formation of (1)·Et₃BuNBr is shown through significant ¹³C chemical shift changes relative to pure solid 1,3,5-tris(iodoethynyl)-2,4,6-trifluorobenzene.

Keywords: NMR spectroscopy; halogen bond; crystal engineering; iodine; X-ray diffraction; isotope shift.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520617000944/xm5005sup1.cif Contains datablocks 1a, 1b, 1c, 1d, 1e, 1f, 1g, g, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520617000944/xm50051asup2.hkl Contains datablock 1a
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520617000944/xm50051bsup3.hkl Contains datablock 1b
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520617000944/xm50051csup4.hkl Contains datablock 1c
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520617000944/xm50051dsup5.hkl Contains datablock 1d
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520617000944/xm50051esup6.hkl Contains datablock 1e
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520617000944/xm50051fsup7.hkl Contains datablock 1f
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520617000944/xm50051gsup8.hkl Contains datablock 1g
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520617000944/xm5005gsup9.hkl Contains datablock g
	Portable Document Format (PDF) file https://doi.org/10.1107/S2052520617000944/xm5005sup10.pdf Additional spectral simulations, experimental details, and ORTEP plots

CCDC references: 1528339; 1528340; 1528341; 1528342; 1528343; 1528344; 1528345; 1528346

Computing details top

Data collection: APEX II (Bruker, 2009) for (1a), (1c), (1g); APEX II, Bruker (2009) for (1b), (1d), (1e), (1f), g. Cell refinement: APEX II (Bruker, 2009) for (1a), (1c), (1g); APEX II, Bruker (2009) for (1b), (1d), (1e), (1f), g. Data reduction: SAINT (Bruker) for (1a), (1c), (1g); XPREP, Bruker (2009) for (1b), (1d), (1e), (1f), g. Program(s) used to solve structure: XT (Sheldrick, 2014) for (1a), (1c), (1g); SHELXS03 (Sheldrick, 2003) for (1b), (1d), (1e), (1f), g. Program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014) for (1a), (1b), (1c), (1g); SHELXL2013 (Sheldrick, 2013) for (1d), (1e), (1f), g. Molecular graphics: Mercury (Macrae et al., 2008) for (1a), (1b), (1c), (1g); SHELXTL, Bruker (2004) for (1d), (1e), (1f), g. Software used to prepare material for publication: CIFTAB (Sheldrick, 1997) for (1a), (1b), (1c), (1g); SHELXTL, Bruker (2004) for (1d), (1e), (1f), g.

(1a) top

Crystal data top

C₁₂F₃I₃·C₁₀H₂₄N·Br	D_x = 1.995 Mg m⁻³
M_r = 820.03	Melting point: 451 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 15.7522 (5) Å	Cell parameters from 9890 reflections
b = 22.3326 (7) Å	θ = 2.3–27.9°
c = 15.5213 (5) Å	µ = 4.93 mm⁻¹
V = 5460.2 (3) Å³	T = 200 K
Z = 8	Block, colourless
F(000) = 3072	0.15 × 0.12 × 0.09 mm

Data collection top

Bruker APEX-II CCD diffractometer	5501 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.042
Absorption correction: multi-scan SADABS, Bruker (2003)	θ_max = 28.3°, θ_min = 1.8°
T_min = 0.556, T_max = 0.746	h = −21→21
77024 measured reflections	k = −29→29
6773 independent reflections	l = −20→19

Refinement top

Refinement on F²	524 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.083	H-atom parameters constrained
wR(F²) = 0.183	w = 1/[σ²(F_o²) + 174.478P] where P = (F_o² + 2F_c²)/3
S = 1.22	(Δ/σ)_max = 0.001
6773 reflections	Δρ_max = 1.56 e Å⁻³
379 parameters	Δρ_min = −1.62 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
I1	0.18273 (6)	0.41030 (4)	0.90800 (6)	0.0484 (2)
I2	−0.13024 (6)	0.73272 (4)	0.50125 (6)	0.0475 (2)
I3	0.20906 (7)	0.39536 (4)	0.23730 (7)	0.0594 (3)
Br1	0.73588 (11)	0.82985 (6)	0.44165 (10)	0.0555 (4)
F1	0.0386 (6)	0.5775 (4)	0.7026 (6)	0.060 (2)
F2	0.0715 (6)	0.5679 (4)	0.4039 (6)	0.059 (2)
F3	0.1920 (6)	0.4203 (4)	0.5802 (6)	0.066 (2)
C1	0.1170 (7)	0.4983 (6)	0.6459 (10)	0.044 (3)
C2	0.0702 (8)	0.5503 (6)	0.6343 (9)	0.043 (3)
C3	0.0543 (8)	0.5755 (6)	0.5548 (10)	0.047 (3)
C4	0.0865 (8)	0.5443 (6)	0.4829 (9)	0.045 (3)
C5	0.1337 (8)	0.4919 (6)	0.4895 (9)	0.043 (3)
C6	0.1467 (8)	0.4710 (6)	0.5707 (10)	0.048 (3)
C7	0.1323 (9)	0.4733 (6)	0.7300 (10)	0.050 (3)
C8	0.1489 (9)	0.4517 (6)	0.7982 (10)	0.053 (4)
C9	0.0031 (9)	0.6281 (6)	0.5436 (10)	0.049 (3)
C10	−0.0459 (10)	0.6685 (6)	0.5275 (11)	0.055 (4)
C11	0.1620 (9)	0.4627 (7)	0.4159 (12)	0.058 (4)
C12	0.1810 (10)	0.4379 (7)	0.3493 (12)	0.059 (4)
N1	0.0777 (10)	0.7142 (7)	0.2478 (12)	0.079 (5)	0.536 (10)
C13	0.074 (2)	0.6965 (10)	0.1551 (14)	0.088 (6)	0.536 (10)
H13A	0.1177	0.7191	0.1234	0.105*	0.536 (10)
H13B	0.0178	0.7091	0.1319	0.105*	0.536 (10)
C14	0.085 (3)	0.6305 (10)	0.1363 (17)	0.097 (7)	0.536 (10)
H14A	0.0405	0.6072	0.1658	0.117*	0.536 (10)
H14B	0.1410	0.6171	0.1587	0.117*	0.536 (10)
C15	0.081 (3)	0.6187 (13)	0.0390 (17)	0.111 (9)	0.536 (10)
H15A	0.0263	0.6338	0.0161	0.133*	0.536 (10)
H15B	0.1274	0.6405	0.0097	0.133*	0.536 (10)
C16	0.089 (3)	0.5519 (14)	0.021 (3)	0.129 (13)	0.536 (10)
H16A	0.0698	0.5437	−0.0383	0.194*	0.536 (10)
H16B	0.0533	0.5295	0.0613	0.194*	0.536 (10)
H16C	0.1481	0.5395	0.0272	0.194*	0.536 (10)
C17	0.1571 (13)	0.6908 (12)	0.2859 (17)	0.081 (6)	0.536 (10)
H17A	0.1579	0.6468	0.2783	0.098*	0.536 (10)
H17B	0.1560	0.6989	0.3486	0.098*	0.536 (10)
C18	0.2389 (14)	0.7159 (18)	0.250 (3)	0.092 (11)	0.536 (10)
H18A	0.2557	0.6927	0.1989	0.138*	0.536 (10)
H18B	0.2837	0.7133	0.2934	0.138*	0.536 (10)
H18C	0.2304	0.7578	0.2334	0.138*	0.536 (10)
C19	0.075 (2)	0.7808 (9)	0.2539 (16)	0.088 (7)	0.536 (10)
H19A	0.0223	0.7950	0.2251	0.106*	0.536 (10)
H19B	0.1236	0.7974	0.2219	0.106*	0.536 (10)
C20	0.076 (4)	0.8056 (15)	0.346 (2)	0.124 (15)	0.536 (10)
H20A	0.0248	0.8292	0.3560	0.186*	0.536 (10)
H20B	0.1263	0.8312	0.3531	0.186*	0.536 (10)
H20C	0.0787	0.7724	0.3869	0.186*	0.536 (10)
C21	0.0029 (14)	0.6887 (13)	0.2947 (18)	0.088 (7)	0.536 (10)
H21A	0.0069	0.7002	0.3562	0.106*	0.536 (10)
H21B	0.0057	0.6445	0.2916	0.106*	0.536 (10)
C22	−0.0829 (14)	0.7090 (16)	0.260 (2)	0.082 (9)	0.536 (10)
H22A	−0.0895	0.7521	0.2694	0.122*	0.536 (10)
H22B	−0.1283	0.6875	0.2902	0.122*	0.536 (10)
H22C	−0.0861	0.7003	0.1983	0.122*	0.536 (10)
N2	0.0970 (14)	0.6686 (9)	0.1950 (14)	0.088 (5)	0.464 (10)
C23	0.0674 (19)	0.6656 (16)	0.1036 (16)	0.103 (7)	0.464 (10)
H23A	0.0384	0.7037	0.0895	0.123*	0.464 (10)
H23B	0.0248	0.6331	0.0989	0.123*	0.464 (10)
C24	0.136 (2)	0.655 (2)	0.0375 (18)	0.119 (9)	0.464 (10)
H24A	0.1567	0.6133	0.0438	0.143*	0.464 (10)
H24B	0.1835	0.6823	0.0490	0.143*	0.464 (10)
C25	0.106 (3)	0.664 (2)	−0.0543 (18)	0.126 (11)	0.464 (10)
H25A	0.1554	0.6728	−0.0911	0.151*	0.464 (10)
H25B	0.0674	0.6990	−0.0562	0.151*	0.464 (10)
C26	0.059 (4)	0.610 (3)	−0.091 (4)	0.17 (2)	0.464 (10)
H26A	0.0904	0.5735	−0.0763	0.257*	0.464 (10)
H26B	0.0557	0.6140	−0.1537	0.257*	0.464 (10)
H26C	0.0021	0.6082	−0.0666	0.257*	0.464 (10)
C27	0.154 (2)	0.7221 (12)	0.204 (2)	0.095 (7)	0.464 (10)
H27A	0.1209	0.7585	0.1898	0.114*	0.464 (10)
H27B	0.2004	0.7187	0.1615	0.114*	0.464 (10)
C28	0.192 (3)	0.730 (2)	0.292 (3)	0.111 (12)	0.464 (10)
H28A	0.2133	0.7710	0.2982	0.167*	0.464 (10)
H28B	0.2393	0.7017	0.2993	0.167*	0.464 (10)
H28C	0.1490	0.7222	0.3361	0.167*	0.464 (10)
C29	0.0220 (19)	0.6763 (13)	0.253 (2)	0.099 (7)	0.464 (10)
H29A	0.0399	0.6698	0.3131	0.119*	0.464 (10)
H29B	−0.0210	0.6456	0.2383	0.119*	0.464 (10)
C30	−0.018 (2)	0.7386 (16)	0.245 (3)	0.103 (10)	0.464 (10)
H30A	0.0084	0.7603	0.1968	0.154*	0.464 (10)
H30B	−0.0094	0.7608	0.2983	0.154*	0.464 (10)
H30C	−0.0791	0.7345	0.2336	0.154*	0.464 (10)
C31	0.1438 (18)	0.6137 (11)	0.219 (2)	0.096 (8)	0.464 (10)
H31A	0.1567	0.6152	0.2810	0.115*	0.464 (10)
H31B	0.1986	0.6135	0.1874	0.115*	0.464 (10)
C32	0.098 (3)	0.5554 (11)	0.200 (3)	0.094 (12)	0.464 (10)
H32A	0.0379	0.5593	0.2155	0.141*	0.464 (10)
H32B	0.1237	0.5229	0.2333	0.141*	0.464 (10)
H32C	0.1024	0.5462	0.1382	0.141*	0.464 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0535 (5)	0.0431 (4)	0.0488 (5)	−0.0088 (4)	−0.0068 (4)	0.0060 (4)
I2	0.0475 (5)	0.0398 (4)	0.0553 (5)	0.0071 (4)	−0.0005 (4)	0.0033 (4)
I3	0.0614 (6)	0.0493 (5)	0.0676 (7)	−0.0103 (5)	0.0074 (5)	−0.0086 (5)
Br1	0.0688 (10)	0.0461 (7)	0.0515 (8)	0.0169 (7)	−0.0134 (7)	−0.0046 (6)
F1	0.058 (5)	0.063 (5)	0.057 (5)	0.006 (4)	0.003 (4)	−0.004 (4)
F2	0.063 (5)	0.057 (5)	0.057 (5)	0.002 (4)	−0.003 (4)	0.017 (4)
F3	0.068 (6)	0.052 (5)	0.080 (6)	0.017 (4)	−0.015 (5)	0.009 (5)
C1	0.027 (6)	0.036 (6)	0.070 (9)	−0.004 (5)	−0.014 (6)	0.009 (6)
C2	0.035 (6)	0.041 (7)	0.052 (8)	0.002 (5)	−0.002 (6)	0.006 (6)
C3	0.038 (7)	0.037 (6)	0.065 (9)	−0.004 (5)	−0.002 (6)	0.015 (6)
C4	0.038 (7)	0.042 (7)	0.054 (8)	−0.009 (5)	−0.006 (6)	0.013 (6)
C5	0.037 (6)	0.039 (6)	0.054 (8)	−0.007 (5)	0.006 (6)	−0.002 (6)
C6	0.031 (6)	0.042 (7)	0.072 (10)	−0.003 (5)	−0.008 (6)	0.008 (7)
C7	0.043 (7)	0.050 (8)	0.055 (9)	−0.008 (6)	0.002 (7)	0.010 (7)
C8	0.049 (8)	0.043 (7)	0.065 (10)	−0.004 (6)	−0.014 (7)	0.012 (7)
C9	0.047 (8)	0.039 (7)	0.061 (9)	−0.006 (6)	−0.002 (7)	0.008 (6)
C10	0.050 (8)	0.048 (8)	0.069 (10)	−0.001 (7)	0.012 (7)	0.007 (7)
C11	0.045 (8)	0.045 (8)	0.085 (12)	−0.003 (6)	0.006 (8)	−0.005 (8)
C12	0.049 (8)	0.043 (7)	0.086 (12)	−0.001 (7)	0.009 (8)	−0.008 (8)
N1	0.077 (9)	0.067 (9)	0.091 (11)	−0.009 (7)	−0.002 (8)	0.008 (8)
C13	0.082 (13)	0.084 (11)	0.097 (11)	0.002 (10)	−0.007 (9)	0.001 (8)
C14	0.088 (15)	0.085 (11)	0.118 (13)	0.010 (10)	−0.011 (12)	−0.007 (9)
C15	0.094 (19)	0.120 (15)	0.119 (14)	−0.006 (14)	−0.004 (13)	−0.022 (11)
C16	0.10 (3)	0.121 (17)	0.17 (3)	−0.014 (17)	0.02 (2)	−0.037 (15)
C17	0.077 (10)	0.075 (13)	0.092 (14)	−0.009 (9)	−0.004 (9)	0.009 (10)
C18	0.078 (12)	0.10 (2)	0.10 (2)	−0.010 (12)	−0.009 (12)	0.03 (2)
C19	0.096 (15)	0.071 (9)	0.098 (14)	−0.005 (9)	0.004 (12)	0.006 (9)
C20	0.17 (4)	0.10 (2)	0.107 (17)	−0.02 (2)	0.009 (18)	−0.012 (14)
C21	0.084 (10)	0.084 (14)	0.096 (14)	−0.012 (9)	−0.003 (9)	0.005 (11)
C22	0.081 (11)	0.081 (19)	0.08 (2)	−0.012 (11)	−0.003 (11)	0.004 (17)
N2	0.081 (10)	0.075 (10)	0.107 (12)	0.003 (8)	−0.005 (9)	0.011 (9)
C23	0.100 (13)	0.097 (15)	0.112 (12)	0.009 (12)	−0.007 (10)	0.007 (10)
C24	0.118 (17)	0.12 (2)	0.124 (13)	0.011 (15)	0.007 (12)	0.007 (12)
C25	0.12 (2)	0.14 (2)	0.118 (14)	0.02 (2)	0.005 (13)	0.005 (13)
C26	0.18 (5)	0.17 (3)	0.16 (3)	0.00 (3)	−0.01 (3)	−0.02 (2)
C27	0.088 (12)	0.083 (11)	0.114 (14)	0.001 (10)	−0.002 (11)	0.009 (10)
C28	0.12 (3)	0.09 (2)	0.124 (17)	0.00 (2)	−0.019 (17)	0.008 (15)
C29	0.089 (12)	0.096 (13)	0.112 (14)	0.003 (10)	−0.004 (11)	0.004 (11)
C30	0.100 (19)	0.095 (15)	0.11 (2)	0.011 (14)	−0.041 (18)	−0.014 (15)
C31	0.092 (14)	0.082 (11)	0.114 (17)	0.004 (10)	−0.004 (12)	0.014 (11)
C32	0.10 (2)	0.076 (12)	0.11 (3)	0.003 (12)	−0.01 (2)	0.021 (13)

Geometric parameters (Å, º) top

I1—C8	2.011 (15)	C20—H20A	0.9800
I2—C10	1.997 (15)	C20—H20B	0.9800
I3—C12	2.030 (17)	C20—H20C	0.9800
F1—C2	1.319 (16)	C21—C22	1.522 (15)
F2—C4	1.356 (15)	C21—H21A	0.9900
F3—C6	1.347 (15)	C21—H21B	0.9900
C1—C2	1.388 (17)	C22—H22A	0.9800
C1—C6	1.40 (2)	C22—H22B	0.9800
C1—C7	1.440 (19)	C22—H22C	0.9800
C2—C3	1.379 (19)	N2—C31	1.479 (18)
C3—C4	1.41 (2)	N2—C29	1.491 (18)
C3—C9	1.435 (18)	N2—C23	1.494 (17)
C4—C5	1.390 (18)	N2—C27	1.500 (18)
C5—C6	1.36 (2)	C23—C24	1.504 (16)
C5—C11	1.39 (2)	C23—H23A	0.9900
C7—C8	1.19 (2)	C23—H23B	0.9900
C9—C10	1.213 (19)	C24—C25	1.514 (16)
C11—C12	1.21 (2)	C24—H24A	0.9900
N1—C17	1.481 (17)	C24—H24B	0.9900
N1—C19	1.489 (17)	C25—C26	1.514 (16)
N1—C13	1.493 (17)	C25—H25A	0.9900
N1—C21	1.498 (17)	C25—H25B	0.9900
C13—C14	1.516 (15)	C26—H26A	0.9800
C13—H13A	0.9900	C26—H26B	0.9800
C13—H13B	0.9900	C26—H26C	0.9800
C14—C15	1.533 (16)	C27—C28	1.503 (15)
C14—H14A	0.9900	C27—H27A	0.9900
C14—H14B	0.9900	C27—H27B	0.9900
C15—C16	1.525 (16)	C28—H28A	0.9800
C15—H15A	0.9900	C28—H28B	0.9800
C15—H15B	0.9900	C28—H28C	0.9800
C16—H16A	0.9800	C29—C30	1.532 (16)
C16—H16B	0.9800	C29—H29A	0.9900
C16—H16C	0.9800	C29—H29B	0.9900
C17—C18	1.513 (15)	C30—H30A	0.9800
C17—H17A	0.9900	C30—H30B	0.9800
C17—H17B	0.9900	C30—H30C	0.9800
C18—H18A	0.9800	C31—C32	1.519 (15)
C18—H18B	0.9800	C31—H31A	0.9900
C18—H18C	0.9800	C31—H31B	0.9900
C19—C20	1.530 (15)	C32—H32A	0.9800
C19—H19A	0.9900	C32—H32B	0.9800
C19—H19B	0.9900	C32—H32C	0.9800

C2—C1—C6	115.7 (13)	N1—C21—C22	114.4 (15)
C2—C1—C7	122.1 (14)	N1—C21—H21A	108.7
C6—C1—C7	122.1 (12)	C22—C21—H21A	108.7
F1—C2—C3	117.6 (12)	N1—C21—H21B	108.7
F1—C2—C1	118.7 (13)	C22—C21—H21B	108.7
C3—C2—C1	123.7 (14)	H21A—C21—H21B	107.6
C2—C3—C4	116.1 (12)	C21—C22—H22A	109.5
C2—C3—C9	123.0 (14)	C21—C22—H22B	109.5
C4—C3—C9	120.7 (13)	H22A—C22—H22B	109.5
F2—C4—C5	119.1 (13)	C21—C22—H22C	109.5
F2—C4—C3	117.5 (12)	H22A—C22—H22C	109.5
C5—C4—C3	123.4 (13)	H22B—C22—H22C	109.5
C6—C5—C4	116.0 (13)	C31—N2—C29	110.0 (11)
C6—C5—C11	123.5 (13)	C31—N2—C23	110.7 (10)
C4—C5—C11	120.4 (14)	C29—N2—C23	109.2 (11)
F3—C6—C5	118.0 (14)	C31—N2—C27	109.8 (11)
F3—C6—C1	117.0 (13)	C29—N2—C27	108.9 (10)
C5—C6—C1	125.0 (12)	C23—N2—C27	108.2 (10)
C8—C7—C1	176.6 (16)	N2—C23—C24	115.6 (17)
C7—C8—I1	175.3 (15)	N2—C23—H23A	108.4
C10—C9—C3	172.3 (16)	C24—C23—H23A	108.4
C9—C10—I2	177.8 (13)	N2—C23—H23B	108.4
C12—C11—C5	175.3 (18)	C24—C23—H23B	108.4
C11—C12—I3	178.2 (14)	H23A—C23—H23B	107.4
C17—N1—C19	110.8 (10)	C23—C24—C25	113.5 (17)
C17—N1—C13	109.2 (10)	C23—C24—H24A	108.9
C19—N1—C13	108.9 (10)	C25—C24—H24A	108.9
C17—N1—C21	109.6 (10)	C23—C24—H24B	108.9
C19—N1—C21	108.9 (10)	C25—C24—H24B	108.9
C13—N1—C21	109.5 (10)	H24A—C24—H24B	107.7
N1—C13—C14	116.0 (14)	C24—C25—C26	113.4 (18)
N1—C13—H13A	108.3	C24—C25—H25A	108.9
C14—C13—H13A	108.3	C26—C25—H25A	108.9
N1—C13—H13B	108.3	C24—C25—H25B	108.9
C14—C13—H13B	108.3	C26—C25—H25B	108.9
H13A—C13—H13B	107.4	H25A—C25—H25B	107.7
C13—C14—C15	110.6 (15)	C25—C26—H26A	109.5
C13—C14—H14A	109.5	C25—C26—H26B	109.5
C15—C14—H14A	109.5	H26A—C26—H26B	109.5
C13—C14—H14B	109.5	C25—C26—H26C	109.5
C15—C14—H14B	109.5	H26A—C26—H26C	109.5
H14A—C14—H14B	108.1	H26B—C26—H26C	109.5
C16—C15—C14	110.4 (16)	N2—C27—C28	114.7 (18)
C16—C15—H15A	109.6	N2—C27—H27A	108.6
C14—C15—H15A	109.6	C28—C27—H27A	108.6
C16—C15—H15B	109.6	N2—C27—H27B	108.6
C14—C15—H15B	109.6	C28—C27—H27B	108.6
H15A—C15—H15B	108.1	H27A—C27—H27B	107.6
C15—C16—H16A	109.5	C27—C28—H28A	109.5
C15—C16—H16B	109.5	C27—C28—H28B	109.5
H16A—C16—H16B	109.5	H28A—C28—H28B	109.5
C15—C16—H16C	109.5	C27—C28—H28C	109.5
H16A—C16—H16C	109.5	H28A—C28—H28C	109.5
H16B—C16—H16C	109.5	H28B—C28—H28C	109.5
N1—C17—C18	116.1 (15)	N2—C29—C30	112.5 (17)
N1—C17—H17A	108.3	N2—C29—H29A	109.1
C18—C17—H17A	108.3	C30—C29—H29A	109.1
N1—C17—H17B	108.3	N2—C29—H29B	109.1
C18—C17—H17B	108.3	C30—C29—H29B	109.1
H17A—C17—H17B	107.4	H29A—C29—H29B	107.8
C17—C18—H18A	109.5	C29—C30—H30A	109.5
C17—C18—H18B	109.5	C29—C30—H30B	109.5
H18A—C18—H18B	109.5	H30A—C30—H30B	109.5
C17—C18—H18C	109.5	C29—C30—H30C	109.5
H18A—C18—H18C	109.5	H30A—C30—H30C	109.5
H18B—C18—H18C	109.5	H30B—C30—H30C	109.5
N1—C19—C20	114.9 (15)	N2—C31—C32	115.2 (17)
N1—C19—H19A	108.5	N2—C31—H31A	108.5
C20—C19—H19A	108.5	C32—C31—H31A	108.5
N1—C19—H19B	108.5	N2—C31—H31B	108.5
C20—C19—H19B	108.5	C32—C31—H31B	108.5
H19A—C19—H19B	107.5	H31A—C31—H31B	107.5
C19—C20—H20A	109.5	C31—C32—H32A	109.5
C19—C20—H20B	109.5	C31—C32—H32B	109.5
H20A—C20—H20B	109.5	H32A—C32—H32B	109.5
C19—C20—H20C	109.5	C31—C32—H32C	109.5
H20A—C20—H20C	109.5	H32A—C32—H32C	109.5
H20B—C20—H20C	109.5	H32B—C32—H32C	109.5

C6—C1—C2—F1	178.4 (11)	C21—N1—C13—C14	−67 (3)
C7—C1—C2—F1	−0.2 (19)	N1—C13—C14—C15	−179 (3)
C6—C1—C2—C3	−1.4 (19)	C13—C14—C15—C16	−177 (4)
C7—C1—C2—C3	−179.9 (13)	C19—N1—C17—C18	−56 (3)
F1—C2—C3—C4	−178.0 (11)	C13—N1—C17—C18	64 (3)
C1—C2—C3—C4	2 (2)	C21—N1—C17—C18	−176 (3)
F1—C2—C3—C9	−2 (2)	C17—N1—C19—C20	−61 (3)
C1—C2—C3—C9	177.6 (12)	C13—N1—C19—C20	179 (3)
C2—C3—C4—F2	179.7 (11)	C21—N1—C19—C20	59 (3)
C9—C3—C4—F2	3.9 (18)	C17—N1—C21—C22	−179 (3)
C2—C3—C4—C5	−1.6 (19)	C19—N1—C21—C22	60 (3)
C9—C3—C4—C5	−177.5 (12)	C13—N1—C21—C22	−59 (3)
F2—C4—C5—C6	179.6 (11)	C31—N2—C23—C24	−56 (4)
C3—C4—C5—C6	1.0 (19)	C29—N2—C23—C24	−177 (3)
F2—C4—C5—C11	−2.8 (19)	C27—N2—C23—C24	64 (4)
C3—C4—C5—C11	178.6 (13)	N2—C23—C24—C25	−169 (3)
C4—C5—C6—F3	179.9 (11)	C23—C24—C25—C26	−82 (5)
C11—C5—C6—F3	2 (2)	C31—N2—C27—C28	−57 (4)
C4—C5—C6—C1	0 (2)	C29—N2—C27—C28	64 (4)
C11—C5—C6—C1	−178.0 (13)	C23—N2—C27—C28	−177 (3)
C2—C1—C6—F3	−179.7 (11)	C31—N2—C29—C30	168 (3)
C7—C1—C6—F3	−1.2 (18)	C23—N2—C29—C30	−71 (3)
C2—C1—C6—C5	0.7 (19)	C27—N2—C29—C30	47 (3)
C7—C1—C6—C5	179.2 (13)	C29—N2—C31—C32	69 (3)
C17—N1—C13—C14	53 (3)	C23—N2—C31—C32	−52 (3)
C19—N1—C13—C14	174 (3)	C27—N2—C31—C32	−171 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···I1ⁱ	0.98	3.33	3.94 (3)	122
C18—H18C···I3ⁱⁱ	0.98	3.22	4.10 (4)	150
C21—H21A···I2	0.99	3.20	3.95 (3)	134
C23—H23A···I2ⁱⁱⁱ	0.99	3.31	4.17 (3)	146
C24—H24A···F3ⁱ	0.99	2.56	3.26 (4)	128
C24—H24B···I2^iv	0.99	3.24	4.12 (4)	150
C27—H27B···Br1^v	0.99	3.01	3.55 (3)	116
C28—H28A···I3ⁱⁱ	0.98	3.18	4.10 (4)	157
C28—H28B···I1ⁱ	0.98	3.26	4.11 (5)	147
C31—H31A···I1ⁱ	0.99	3.26	4.05 (3)	138
C31—H31A···F2	0.99	2.56	3.26 (4)	127
C31—H31B···F3ⁱ	0.99	2.51	3.45 (4)	158
C32—H32B···I3	0.98	3.15	4.02 (3)	149

Symmetry codes: (i) −x+1/2, −y+1, z−1/2; (ii) −x+1/2, y+1/2, z; (iii) x, −y+3/2, z−1/2; (iv) x+1/2, y, −z+1/2; (v) x−1/2, y, −z+1/2.

(1b) top

Crystal data top

C₁₂F₃I₃·C₁₀H₂₄N·Br	D_x = 1.947 Mg m⁻³
M_r = 820.03	Melting point: 453 K
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 31.434 (4) Å	Cell parameters from 9963 reflections
b = 14.8275 (19) Å	θ = 2.4–22.2°
c = 26.724 (4) Å	µ = 4.81 mm⁻¹
β = 116.034 (7)°	T = 200 K
V = 11192 (3) Å³	Plate, colourless
Z = 16	0.11 × 0.06 × 0.01 mm
F(000) = 6144

Data collection top

Bruker APEX-II CCD diffractometer	5235 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.082
Absorption correction: multi-scan SADABS, Bruker (2003)	θ_max = 25.3°, θ_min = 1.4°
T_min = 0.578, T_max = 0.746	h = −37→37
65445 measured reflections	k = −17→17
10111 independent reflections	l = −32→32

Refinement top

Refinement on F²	228 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.138	w = 1/[σ²(F_o²) + (0.0634P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.005
10111 reflections	Δρ_max = 0.76 e Å⁻³
595 parameters	Δρ_min = −0.72 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
I1	0.09444 (2)	0.81500 (4)	0.09230 (3)	0.0694 (2)
I2	−0.22682 (3)	0.43739 (5)	−0.08810 (4)	0.0863 (3)
I3	0.09942 (3)	0.13397 (4)	0.10578 (3)	0.0789 (2)
I4	0.27017 (3)	0.97795 (5)	0.61143 (4)	0.0856 (3)
I5	0.58621 (3)	0.58085 (4)	0.74227 (3)	0.0737 (2)
I6	0.59759 (2)	1.25846 (5)	0.75626 (3)	0.0717 (2)
Br7	0.66719 (4)	0.43307 (7)	0.80659 (5)	0.0732 (3)
Br8	0.16989 (4)	0.97643 (7)	0.11318 (6)	0.0815 (4)
F1	−0.0685 (2)	0.6241 (3)	0.0221 (2)	0.0780 (16)
F2	−0.0615 (2)	0.3116 (3)	0.0356 (2)	0.0765 (16)
F3	0.0771 (2)	0.4802 (4)	0.1044 (3)	0.0828 (17)
F4	0.4228 (2)	0.7759 (4)	0.6487 (3)	0.0876 (18)
F5	0.5711 (2)	0.9138 (4)	0.7212 (3)	0.0829 (17)
F6	0.43459 (19)	1.0894 (3)	0.6546 (2)	0.0728 (15)
C1	0.0052 (4)	0.5560 (6)	0.0642 (4)	0.052 (2)
C2	−0.0440 (4)	0.5500 (6)	0.0377 (4)	0.058 (2)
C3	−0.0673 (3)	0.4671 (6)	0.0273 (4)	0.054 (2)
C4	−0.0394 (4)	0.3911 (6)	0.0451 (4)	0.057 (3)
C5	0.0095 (4)	0.3910 (6)	0.0707 (4)	0.055 (2)
C6	0.0302 (3)	0.4775 (6)	0.0797 (4)	0.055 (2)
C7	0.0299 (3)	0.6404 (6)	0.0741 (4)	0.057 (2)
C8	0.0527 (4)	0.7056 (7)	0.0803 (4)	0.069 (3)
C9	−0.1166 (5)	0.4623 (6)	−0.0036 (5)	0.070 (3)
C10	−0.1594 (4)	0.4525 (7)	−0.0339 (5)	0.081 (3)
C11	0.0365 (4)	0.3097 (7)	0.0843 (4)	0.067 (3)
C12	0.0585 (4)	0.2430 (7)	0.0930 (5)	0.074 (3)
C13	0.4265 (3)	0.9334 (7)	0.6515 (4)	0.058 (2)
C14	0.4495 (4)	0.8510 (6)	0.6618 (4)	0.060 (2)
C15	0.4985 (4)	0.8416 (6)	0.6853 (4)	0.060 (3)
C16	0.5235 (3)	0.9205 (7)	0.6975 (4)	0.059 (3)
C17	0.5046 (4)	1.0059 (6)	0.6892 (4)	0.057 (2)
C18	0.4548 (4)	1.0081 (6)	0.6652 (4)	0.062 (3)
C19	0.3762 (4)	0.9417 (7)	0.6320 (5)	0.073 (3)
C20	0.3368 (4)	0.9520 (7)	0.6215 (5)	0.079 (3)
C21	0.5216 (4)	0.7561 (7)	0.6975 (4)	0.068 (3)
C22	0.5427 (4)	0.6889 (7)	0.7113 (4)	0.072 (3)
C23	0.5334 (4)	1.0847 (7)	0.7070 (4)	0.063 (3)
C24	0.5564 (4)	1.1494 (7)	0.7244 (4)	0.066 (3)
N1	0.2529 (3)	0.7997 (5)	0.2753 (4)	0.081 (3)
C25	0.2001 (4)	0.7964 (8)	0.2506 (5)	0.101 (4)
H25A	0.1870	0.8267	0.2138	0.121*
H25B	0.1895	0.8305	0.2749	0.121*
C26	0.1805 (5)	0.7016 (11)	0.2432 (8)	0.172 (7)
H26A	0.1910	0.6673	0.2193	0.257*
H26B	0.1458	0.7040	0.2259	0.257*
H26C	0.1920	0.6722	0.2796	0.257*
C27	0.2716 (4)	0.7483 (7)	0.2406 (6)	0.100 (4)
H27A	0.2624	0.6842	0.2395	0.120*
H27B	0.3066	0.7510	0.2593	0.120*
C28	0.2547 (5)	0.7815 (8)	0.1809 (6)	0.121 (5)
H28A	0.2282	0.7441	0.1559	0.182*
H28B	0.2807	0.7774	0.1702	0.182*
H28C	0.2443	0.8443	0.1783	0.182*
C29	0.2640 (5)	0.9016 (7)	0.2748 (6)	0.109 (4)
H29A	0.2479	0.9240	0.2360	0.131*
H29B	0.2507	0.9346	0.2969	0.131*
C30	0.3159 (6)	0.9224 (10)	0.2977 (8)	0.169 (7)
H30A	0.3301	0.9217	0.3385	0.253*
H30B	0.3201	0.9822	0.2849	0.253*
H30C	0.3313	0.8770	0.2847	0.253*
C31	0.2763 (5)	0.7618 (7)	0.3335 (6)	0.103 (4)
H31A	0.3107	0.7728	0.3485	0.123*
H31B	0.2715	0.6956	0.3309	0.123*
C32	0.2599 (5)	0.7974 (9)	0.3751 (6)	0.128 (4)
H32A	0.2307	0.7660	0.3707	0.153*
H32B	0.2531	0.8628	0.3692	0.153*
C33	0.3012 (9)	0.7800 (17)	0.4356 (8)	0.173 (8)	0.83 (3)
H33A	0.3067	0.7141	0.4405	0.208*	0.83 (3)
H33B	0.3306	0.8077	0.4376	0.208*	0.83 (3)
C34	0.2938 (12)	0.8127 (14)	0.4810 (9)	0.218 (13)	0.83 (3)
H34A	0.3066	0.8740	0.4903	0.327*	0.83 (3)
H34B	0.3100	0.7733	0.5133	0.327*	0.83 (3)
H34C	0.2598	0.8135	0.4708	0.327*	0.83 (3)
C33'	0.295 (2)	0.762 (5)	0.4352 (13)	0.145 (14)	0.17 (3)
H33C	0.2771	0.7579	0.4580	0.174*	0.17 (3)
H33D	0.3050	0.7001	0.4315	0.174*	0.17 (3)
C34'	0.335 (2)	0.816 (5)	0.464 (3)	0.13 (2)	0.17 (3)
H34D	0.3418	0.8515	0.4370	0.192*	0.17 (3)
H34E	0.3627	0.7770	0.4850	0.192*	0.17 (3)
H34F	0.3301	0.8564	0.4895	0.192*	0.17 (3)
N2	0.4110 (3)	0.4757 (5)	0.5792 (3)	0.081 (2)
C35	0.4481 (4)	0.4495 (9)	0.6384 (5)	0.113 (4)
H35A	0.4703	0.5004	0.6546	0.135*	0.57 (3)
H35B	0.4317	0.4390	0.6622	0.135*	0.57 (3)
H35C	0.4572	0.5037	0.6624	0.135*	0.43 (3)
H35D	0.4340	0.4054	0.6547	0.135*	0.43 (3)
C36	0.4762 (10)	0.365 (2)	0.6392 (11)	0.155 (13)	0.57 (3)
H36A	0.4927	0.3752	0.6159	0.232*	0.57 (3)
H36B	0.4546	0.3139	0.6247	0.232*	0.57 (3)
H36C	0.4994	0.3526	0.6775	0.232*	0.57 (3)
C36'	0.4923 (9)	0.408 (3)	0.6367 (12)	0.159 (16)	0.43 (3)
H36D	0.4965	0.3462	0.6508	0.239*	0.43 (3)
H36E	0.5202	0.4441	0.6601	0.239*	0.43 (3)
H36F	0.4884	0.4080	0.5983	0.239*	0.43 (3)
C37	0.4419 (11)	0.502 (2)	0.5505 (12)	0.099 (6)	0.57 (3)
H37A	0.4215	0.5082	0.5100	0.119*	0.57 (3)
H37B	0.4648	0.4534	0.5558	0.119*	0.57 (3)
C38	0.4691 (13)	0.591 (2)	0.5717 (17)	0.133 (11)	0.57 (3)
H38A	0.4480	0.6363	0.5749	0.199*	0.57 (3)
H38B	0.4811	0.6115	0.5454	0.199*	0.57 (3)
H38C	0.4958	0.5805	0.6082	0.199*	0.57 (3)
C37'	0.4223 (15)	0.536 (2)	0.5388 (13)	0.099 (6)	0.43 (3)
H37C	0.4437	0.5020	0.5271	0.119*	0.43 (3)
H37D	0.3926	0.5478	0.5050	0.119*	0.43 (3)
C38'	0.4455 (18)	0.625 (2)	0.564 (2)	0.133 (11)	0.43 (3)
H38D	0.4234	0.6619	0.5724	0.199*	0.43 (3)
H38E	0.4538	0.6578	0.5376	0.199*	0.43 (3)
H38F	0.4742	0.6143	0.5985	0.199*	0.43 (3)
C39	0.3763 (12)	0.544 (3)	0.5847 (10)	0.087 (4)	0.57 (3)
H39A	0.3615	0.5162	0.6069	0.104*	0.57 (3)
H39B	0.3942	0.5975	0.6051	0.104*	0.57 (3)
C40	0.3376 (10)	0.573 (2)	0.5284 (13)	0.130 (11)	0.57 (3)
H40A	0.3511	0.5796	0.5017	0.195*	0.57 (3)
H40B	0.3245	0.6310	0.5325	0.195*	0.57 (3)
H40C	0.3125	0.5276	0.5148	0.195*	0.57 (3)
C39'	0.3857 (17)	0.540 (4)	0.6029 (14)	0.087 (4)	0.43 (3)
H39C	0.4085	0.5865	0.6260	0.104*	0.43 (3)
H39D	0.3757	0.5052	0.6276	0.104*	0.43 (3)
C40'	0.3425 (14)	0.587 (3)	0.558 (2)	0.159 (17)	0.43 (3)
H40D	0.3528	0.6318	0.5393	0.238*	0.43 (3)
H40E	0.3246	0.6163	0.5759	0.238*	0.43 (3)
H40F	0.3224	0.5419	0.5315	0.238*	0.43 (3)
C41	0.3823 (4)	0.3962 (7)	0.5453 (5)	0.088 (3)
H41A	0.3567	0.4194	0.5103	0.105*
H41B	0.4031	0.3579	0.5351	0.105*
C42	0.3611 (5)	0.3397 (8)	0.5739 (5)	0.102 (4)
H42A	0.3419	0.3779	0.5867	0.123*
H42B	0.3864	0.3110	0.6070	0.123*
C43	0.3300 (5)	0.2675 (8)	0.5347 (6)	0.112 (5)
H43A	0.3036	0.2969	0.5030	0.134*
H43B	0.3488	0.2331	0.5197	0.134*
C44	0.3101 (5)	0.2037 (8)	0.5622 (6)	0.122 (5)
H44A	0.3266	0.2118	0.6027	0.183*
H44B	0.3145	0.1416	0.5528	0.183*
H44C	0.2763	0.2158	0.5493	0.183*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0741 (5)	0.0646 (4)	0.0704 (5)	−0.0203 (3)	0.0326 (4)	−0.0097 (3)
I2	0.0673 (5)	0.0726 (5)	0.1012 (7)	−0.0117 (4)	0.0204 (5)	0.0080 (4)
I3	0.0823 (5)	0.0632 (4)	0.0946 (6)	0.0013 (4)	0.0421 (5)	−0.0104 (4)
I4	0.0594 (5)	0.0744 (5)	0.1172 (7)	0.0061 (4)	0.0336 (5)	0.0112 (4)
I5	0.0730 (5)	0.0654 (4)	0.0820 (6)	0.0110 (4)	0.0335 (4)	0.0205 (4)
I6	0.0680 (5)	0.0786 (4)	0.0659 (5)	−0.0052 (4)	0.0270 (4)	−0.0058 (4)
Br7	0.0617 (7)	0.0634 (6)	0.0824 (9)	0.0083 (5)	0.0206 (6)	0.0068 (5)
Br8	0.0595 (7)	0.0677 (6)	0.1173 (11)	−0.0028 (5)	0.0388 (7)	−0.0034 (6)
F1	0.080 (4)	0.060 (3)	0.092 (5)	0.007 (3)	0.036 (4)	0.015 (3)
F2	0.092 (4)	0.057 (3)	0.087 (4)	−0.017 (3)	0.045 (4)	−0.006 (3)
F3	0.070 (4)	0.088 (4)	0.088 (5)	−0.008 (3)	0.033 (4)	0.000 (3)
F4	0.080 (4)	0.075 (4)	0.102 (5)	−0.005 (3)	0.035 (4)	0.004 (3)
F5	0.060 (4)	0.105 (4)	0.085 (5)	0.005 (3)	0.033 (4)	0.002 (3)
F6	0.078 (4)	0.073 (4)	0.065 (4)	0.016 (3)	0.029 (3)	−0.003 (3)
C1	0.076 (7)	0.051 (5)	0.036 (6)	−0.007 (5)	0.031 (6)	0.000 (4)
C2	0.067 (7)	0.062 (6)	0.048 (7)	0.004 (5)	0.028 (6)	0.010 (5)
C3	0.057 (6)	0.063 (6)	0.040 (6)	−0.024 (5)	0.019 (5)	−0.007 (5)
C4	0.090 (8)	0.042 (5)	0.051 (7)	−0.019 (5)	0.041 (6)	−0.012 (5)
C5	0.061 (7)	0.064 (6)	0.044 (6)	−0.010 (5)	0.027 (6)	0.001 (5)
C6	0.051 (6)	0.067 (6)	0.053 (7)	−0.008 (5)	0.027 (6)	−0.001 (5)
C7	0.064 (7)	0.065 (6)	0.042 (6)	0.000 (5)	0.023 (5)	0.005 (5)
C8	0.088 (8)	0.062 (6)	0.071 (8)	−0.018 (6)	0.047 (7)	−0.008 (5)
C9	0.084 (9)	0.067 (6)	0.066 (8)	−0.008 (6)	0.038 (8)	0.008 (5)
C10	0.067 (8)	0.073 (7)	0.100 (10)	−0.005 (6)	0.032 (8)	0.009 (6)
C11	0.087 (8)	0.065 (6)	0.056 (7)	0.003 (6)	0.037 (6)	−0.005 (5)
C12	0.091 (8)	0.063 (6)	0.079 (8)	0.008 (6)	0.048 (7)	−0.001 (6)
C13	0.056 (7)	0.068 (6)	0.048 (6)	0.002 (5)	0.022 (6)	−0.003 (5)
C14	0.065 (7)	0.066 (6)	0.050 (7)	−0.002 (6)	0.028 (6)	0.000 (5)
C15	0.067 (7)	0.071 (6)	0.050 (7)	0.007 (6)	0.034 (6)	0.008 (5)
C16	0.047 (6)	0.090 (8)	0.044 (6)	−0.002 (6)	0.023 (5)	0.007 (5)
C17	0.065 (7)	0.073 (7)	0.040 (6)	−0.001 (6)	0.031 (6)	0.002 (5)
C18	0.083 (8)	0.064 (6)	0.051 (7)	0.015 (6)	0.040 (6)	0.003 (5)
C19	0.060 (8)	0.072 (7)	0.078 (8)	0.001 (6)	0.024 (7)	0.004 (6)
C20	0.047 (7)	0.081 (7)	0.088 (9)	0.003 (6)	0.010 (7)	0.002 (6)
C21	0.080 (8)	0.060 (6)	0.070 (8)	0.012 (6)	0.038 (7)	0.008 (5)
C22	0.070 (7)	0.083 (7)	0.070 (8)	0.007 (6)	0.038 (7)	0.015 (6)
C23	0.069 (7)	0.080 (7)	0.044 (7)	0.003 (6)	0.029 (6)	−0.005 (5)
C24	0.058 (7)	0.079 (7)	0.057 (7)	−0.001 (6)	0.022 (6)	−0.006 (6)
N1	0.071 (6)	0.058 (4)	0.109 (8)	0.016 (4)	0.035 (6)	−0.008 (5)
C25	0.064 (8)	0.107 (10)	0.120 (12)	−0.002 (7)	0.031 (8)	0.006 (8)
C26	0.110 (12)	0.159 (15)	0.22 (2)	−0.042 (12)	0.049 (13)	0.039 (14)
C27	0.088 (9)	0.074 (7)	0.122 (12)	0.025 (7)	0.033 (9)	−0.013 (8)
C28	0.151 (14)	0.109 (10)	0.107 (13)	0.034 (10)	0.061 (11)	−0.005 (9)
C29	0.143 (10)	0.069 (6)	0.119 (11)	−0.006 (6)	0.060 (10)	−0.013 (6)
C30	0.137 (11)	0.128 (12)	0.23 (2)	−0.046 (9)	0.069 (11)	−0.026 (12)
C31	0.109 (10)	0.071 (7)	0.108 (9)	0.018 (7)	0.030 (8)	0.013 (6)
C32	0.175 (12)	0.091 (8)	0.121 (9)	0.028 (8)	0.068 (9)	0.019 (7)
C33	0.251 (18)	0.120 (15)	0.116 (10)	0.033 (14)	0.051 (10)	0.012 (9)
C34	0.39 (3)	0.120 (16)	0.149 (14)	0.030 (19)	0.124 (16)	0.019 (11)
C33'	0.20 (2)	0.10 (3)	0.117 (13)	0.04 (2)	0.057 (12)	0.016 (12)
C34'	0.17 (3)	0.08 (3)	0.13 (3)	0.07 (2)	0.067 (19)	−0.01 (2)
N2	0.076 (5)	0.090 (5)	0.077 (5)	−0.010 (4)	0.035 (4)	−0.017 (4)
C35	0.093 (8)	0.118 (9)	0.086 (8)	0.024 (7)	0.001 (6)	−0.018 (6)
C36	0.094 (19)	0.145 (17)	0.16 (2)	0.030 (16)	0.000 (16)	−0.017 (14)
C36'	0.093 (13)	0.16 (3)	0.16 (2)	0.016 (17)	0.001 (13)	−0.07 (2)
C37	0.083 (14)	0.127 (13)	0.097 (10)	−0.023 (9)	0.047 (11)	−0.008 (8)
C38	0.13 (3)	0.141 (14)	0.138 (17)	−0.054 (15)	0.07 (2)	−0.026 (14)
C37'	0.083 (14)	0.127 (13)	0.097 (10)	−0.023 (9)	0.047 (11)	−0.008 (8)
C38'	0.13 (3)	0.141 (14)	0.138 (17)	−0.054 (15)	0.07 (2)	−0.026 (14)
C39	0.079 (11)	0.085 (7)	0.091 (12)	−0.001 (7)	0.032 (10)	−0.017 (11)
C40	0.145 (17)	0.090 (16)	0.104 (16)	0.029 (14)	0.007 (14)	−0.025 (15)
C39'	0.079 (11)	0.085 (7)	0.091 (12)	−0.001 (7)	0.032 (10)	−0.017 (11)
C40'	0.13 (2)	0.14 (3)	0.14 (2)	0.05 (2)	0.004 (19)	−0.02 (2)
C41	0.079 (8)	0.089 (8)	0.087 (9)	−0.006 (7)	0.030 (7)	−0.013 (7)
C42	0.141 (12)	0.085 (8)	0.091 (10)	−0.013 (8)	0.059 (10)	−0.007 (7)
C43	0.121 (11)	0.092 (9)	0.137 (13)	−0.018 (8)	0.070 (11)	−0.029 (9)
C44	0.141 (13)	0.101 (9)	0.126 (13)	−0.019 (9)	0.061 (11)	0.002 (9)

Geometric parameters (Å, º) top

I1—C8	2.020 (10)	C33—H33A	0.9900
I2—C10	1.986 (13)	C33—H33B	0.9900
I3—C12	2.000 (10)	C34—H34A	0.9800
I4—C20	2.028 (11)	C34—H34B	0.9800
I5—C22	2.032 (11)	C34—H34C	0.9800
I6—C24	2.012 (11)	C33'—C34'	1.42 (3)
F1—C2	1.301 (10)	C33'—H33C	0.9900
F2—C4	1.336 (9)	C33'—H33D	0.9900
F3—C6	1.326 (10)	C34'—H34D	0.9800
F4—C14	1.344 (10)	C34'—H34E	0.9800
F5—C16	1.347 (10)	C34'—H34F	0.9800
F6—C18	1.333 (10)	N2—C41	1.518 (13)
C1—C6	1.364 (12)	N2—C37	1.532 (13)
C1—C2	1.393 (13)	N2—C39	1.538 (13)
C1—C7	1.435 (12)	N2—C35	1.547 (11)
C2—C3	1.394 (12)	N2—C39'	1.544 (15)
C3—C4	1.378 (12)	N2—C37'	1.558 (15)
C3—C9	1.403 (15)	C35—C36	1.525 (16)
C4—C5	1.380 (13)	C35—C36'	1.537 (17)
C5—C6	1.409 (12)	C35—H35A	0.9900
C5—C11	1.427 (13)	C35—H35B	0.9900
C7—C8	1.172 (11)	C35—H35C	0.9900
C9—C10	1.236 (15)	C35—H35D	0.9900
C11—C12	1.169 (12)	C36—H36A	0.9800
C13—C18	1.366 (13)	C36—H36B	0.9800
C13—C14	1.384 (12)	C36—H36C	0.9800
C13—C19	1.436 (14)	C36'—H36D	0.9800
C14—C15	1.391 (13)	C36'—H36E	0.9800
C15—C16	1.367 (12)	C36'—H36F	0.9800
C15—C21	1.427 (13)	C37—C38	1.529 (16)
C16—C17	1.375 (13)	C37—H37A	0.9900
C17—C18	1.408 (14)	C37—H37B	0.9900
C17—C23	1.426 (14)	C38—H38A	0.9800
C19—C20	1.153 (13)	C38—H38B	0.9800
C21—C22	1.163 (12)	C38—H38C	0.9800
C23—C24	1.168 (12)	C37'—C38'	1.525 (17)
N1—C25	1.493 (12)	C37'—H37C	0.9900
N1—C27	1.504 (13)	C37'—H37D	0.9900
N1—C31	1.507 (14)	C38'—H38D	0.9800
N1—C29	1.552 (13)	C38'—H38E	0.9800
C25—C26	1.513 (17)	C38'—H38F	0.9800
C25—H25A	0.9900	C39—C40	1.525 (16)
C25—H25B	0.9900	C39—H39A	0.9900
C26—H26A	0.9800	C39—H39B	0.9900
C26—H26B	0.9800	C40—H40A	0.9800
C26—H26C	0.9800	C40—H40B	0.9800
C27—C28	1.525 (16)	C40—H40C	0.9800
C27—H27A	0.9900	C39'—C40'	1.523 (17)
C27—H27B	0.9900	C39'—H39C	0.9900
C28—H28A	0.9800	C39'—H39D	0.9900
C28—H28B	0.9800	C40'—H40D	0.9800
C28—H28C	0.9800	C40'—H40E	0.9800
C29—C30	1.503 (18)	C40'—H40F	0.9800
C29—H29A	0.9900	C41—C42	1.477 (14)
C29—H29B	0.9900	C41—H41A	0.9900
C30—H30A	0.9800	C41—H41B	0.9900
C30—H30B	0.9800	C42—C43	1.516 (15)
C30—H30C	0.9800	C42—H42A	0.9900
C31—C32	1.510 (16)	C42—H42B	0.9900
C31—H31A	0.9900	C43—C44	1.493 (15)
C31—H31B	0.9900	C43—H43A	0.9900
C32—C33'	1.58 (3)	C43—H43B	0.9900
C32—C33	1.59 (2)	C44—H44A	0.9800
C32—H32A	0.9900	C44—H44B	0.9800
C32—H32B	0.9900	C44—H44C	0.9800
C33—C34	1.42 (3)

C6—C1—C2	117.6 (8)	C32—C33'—H33C	108.6
C6—C1—C7	119.7 (9)	C34'—C33'—H33D	108.6
C2—C1—C7	122.7 (9)	C32—C33'—H33D	108.6
F1—C2—C3	119.8 (9)	H33C—C33'—H33D	107.6
F1—C2—C1	118.5 (8)	C33'—C34'—H34D	109.5
C3—C2—C1	121.7 (9)	C33'—C34'—H34E	109.5
C4—C3—C2	117.0 (9)	H34D—C34'—H34E	109.5
C4—C3—C9	122.2 (9)	C33'—C34'—H34F	109.5
C2—C3—C9	120.6 (10)	H34D—C34'—H34F	109.5
F2—C4—C3	117.2 (9)	H34E—C34'—H34F	109.5
F2—C4—C5	117.9 (9)	C41—N2—C37	104.0 (11)
C3—C4—C5	125.0 (8)	C41—N2—C39	107.8 (19)
C4—C5—C6	114.4 (9)	C37—N2—C39	121 (2)
C4—C5—C11	122.4 (9)	C41—N2—C35	113.5 (8)
C6—C5—C11	123.1 (9)	C37—N2—C35	102.7 (15)
F3—C6—C1	119.4 (8)	C39—N2—C35	108.3 (11)
F3—C6—C5	116.2 (9)	C41—N2—C39'	117 (3)
C1—C6—C5	124.3 (9)	C35—N2—C39'	91.6 (14)
C8—C7—C1	173.8 (10)	C41—N2—C37'	106.6 (14)
C7—C8—I1	177.7 (10)	C35—N2—C37'	123.6 (17)
C10—C9—C3	174.3 (12)	C39'—N2—C37'	104 (3)
C9—C10—I2	175.1 (10)	C36—C35—N2	113.1 (11)
C12—C11—C5	176.8 (10)	C36'—C35—N2	110.8 (12)
C11—C12—I3	175.5 (9)	C36—C35—H35A	109.0
C18—C13—C14	116.1 (9)	N2—C35—H35A	109.0
C18—C13—C19	120.7 (9)	C36—C35—H35B	109.0
C14—C13—C19	123.0 (9)	N2—C35—H35B	109.0
F4—C14—C13	117.9 (9)	H35A—C35—H35B	107.8
F4—C14—C15	118.3 (9)	C36'—C35—H35C	109.5
C13—C14—C15	123.8 (9)	N2—C35—H35C	109.5
C16—C15—C14	115.4 (9)	C36'—C35—H35D	109.5
C16—C15—C21	121.6 (10)	N2—C35—H35D	109.5
C14—C15—C21	123.0 (9)	H35C—C35—H35D	108.1
F5—C16—C15	116.9 (9)	C35—C36—H36A	109.5
F5—C16—C17	117.1 (9)	C35—C36—H36B	109.5
C15—C16—C17	126.0 (9)	H36A—C36—H36B	109.5
C16—C17—C18	114.2 (9)	C35—C36—H36C	109.5
C16—C17—C23	122.3 (10)	H36A—C36—H36C	109.5
C18—C17—C23	123.4 (9)	H36B—C36—H36C	109.5
F6—C18—C13	118.9 (10)	C35—C36'—H36D	109.5
F6—C18—C17	116.6 (9)	C35—C36'—H36E	109.5
C13—C18—C17	124.5 (9)	H36D—C36'—H36E	109.5
C20—C19—C13	173.2 (12)	C35—C36'—H36F	109.5
C19—C20—I4	173.4 (11)	H36D—C36'—H36F	109.5
C22—C21—C15	174.9 (13)	H36E—C36'—H36F	109.5
C21—C22—I5	173.0 (11)	N2—C37—C38	114.2 (13)
C24—C23—C17	175.8 (10)	N2—C37—H37A	108.7
C23—C24—I6	178.3 (11)	C38—C37—H37A	108.7
C25—N1—C27	111.7 (10)	N2—C37—H37B	108.7
C25—N1—C31	112.8 (9)	C38—C37—H37B	108.7
C27—N1—C31	107.6 (9)	H37A—C37—H37B	107.6
C25—N1—C29	103.7 (9)	C37—C38—H38A	109.5
C27—N1—C29	109.8 (9)	C37—C38—H38B	109.5
C31—N1—C29	111.3 (9)	H38A—C38—H38B	109.5
N1—C25—C26	113.5 (10)	C37—C38—H38C	109.5
N1—C25—H25A	108.9	H38A—C38—H38C	109.5
C26—C25—H25A	108.9	H38B—C38—H38C	109.5
N1—C25—H25B	108.9	C38'—C37'—N2	113.6 (15)
C26—C25—H25B	108.9	C38'—C37'—H37C	108.8
H25A—C25—H25B	107.7	N2—C37'—H37C	108.8
C25—C26—H26A	109.5	C38'—C37'—H37D	108.8
C25—C26—H26B	109.5	N2—C37'—H37D	108.8
H26A—C26—H26B	109.5	H37C—C37'—H37D	107.7
C25—C26—H26C	109.5	C37'—C38'—H38D	109.5
H26A—C26—H26C	109.5	C37'—C38'—H38E	109.5
H26B—C26—H26C	109.5	H38D—C38'—H38E	109.5
N1—C27—C28	115.5 (9)	C37'—C38'—H38F	109.5
N1—C27—H27A	108.4	H38D—C38'—H38F	109.5
C28—C27—H27A	108.4	H38E—C38'—H38F	109.5
N1—C27—H27B	108.4	C40—C39—N2	112.6 (13)
C28—C27—H27B	108.4	C40—C39—H39A	109.1
H27A—C27—H27B	107.5	N2—C39—H39A	109.1
C27—C28—H28A	109.5	C40—C39—H39B	109.1
C27—C28—H28B	109.5	N2—C39—H39B	109.1
H28A—C28—H28B	109.5	H39A—C39—H39B	107.8
C27—C28—H28C	109.5	C39—C40—H40A	109.5
H28A—C28—H28C	109.5	C39—C40—H40B	109.5
H28B—C28—H28C	109.5	H40A—C40—H40B	109.5
C30—C29—N1	113.8 (11)	C39—C40—H40C	109.5
C30—C29—H29A	108.8	H40A—C40—H40C	109.5
N1—C29—H29A	108.8	H40B—C40—H40C	109.5
C30—C29—H29B	108.8	N2—C39'—C40'	113.7 (15)
N1—C29—H29B	108.8	N2—C39'—H39C	108.8
H29A—C29—H29B	107.7	C40'—C39'—H39C	108.8
C29—C30—H30A	109.5	N2—C39'—H39D	108.8
C29—C30—H30B	109.5	C40'—C39'—H39D	108.8
H30A—C30—H30B	109.5	H39C—C39'—H39D	107.7
C29—C30—H30C	109.5	C39'—C40'—H40D	109.5
H30A—C30—H30C	109.5	C39'—C40'—H40E	109.5
H30B—C30—H30C	109.5	H40D—C40'—H40E	109.5
N1—C31—C32	117.4 (10)	C39'—C40'—H40F	109.5
N1—C31—H31A	107.9	H40D—C40'—H40F	109.5
C32—C31—H31A	107.9	H40E—C40'—H40F	109.5
N1—C31—H31B	107.9	C42—C41—N2	114.6 (10)
C32—C31—H31B	107.9	C42—C41—H41A	108.6
H31A—C31—H31B	107.2	N2—C41—H41A	108.6
C31—C32—C33'	109 (3)	C42—C41—H41B	108.6
C31—C32—C33	107.7 (13)	N2—C41—H41B	108.6
C31—C32—H32A	110.2	H41A—C41—H41B	107.6
C33—C32—H32A	110.2	C41—C42—C43	110.1 (10)
C31—C32—H32B	110.2	C41—C42—H42A	109.6
C33—C32—H32B	110.2	C43—C42—H42A	109.6
H32A—C32—H32B	108.5	C41—C42—H42B	109.6
C34—C33—C32	117 (2)	C43—C42—H42B	109.6
C34—C33—H33A	108.1	H42A—C42—H42B	108.2
C32—C33—H33A	108.1	C44—C43—C42	112.9 (11)
C34—C33—H33B	108.1	C44—C43—H43A	109.0
C32—C33—H33B	108.1	C42—C43—H43A	109.0
H33A—C33—H33B	107.3	C44—C43—H43B	109.0
C33—C34—H34A	109.5	C42—C43—H43B	109.0
C33—C34—H34B	109.5	H43A—C43—H43B	107.8
H34A—C34—H34B	109.5	C43—C44—H44A	109.5
C33—C34—H34C	109.5	C43—C44—H44B	109.5
H34A—C34—H34C	109.5	H44A—C44—H44B	109.5
H34B—C34—H34C	109.5	C43—C44—H44C	109.5
C34'—C33'—C32	115 (4)	H44A—C44—H44C	109.5
C34'—C33'—H33C	108.6	H44B—C44—H44C	109.5

C6—C1—C2—F1	−179.3 (7)	C23—C17—C18—F6	6.1 (13)
C7—C1—C2—F1	−1.1 (13)	C16—C17—C18—C13	1.1 (13)
C6—C1—C2—C3	0.2 (13)	C23—C17—C18—C13	−175.0 (8)
C7—C1—C2—C3	178.4 (8)	C27—N1—C25—C26	58.1 (14)
F1—C2—C3—C4	−179.6 (7)	C31—N1—C25—C26	−63.3 (14)
C1—C2—C3—C4	0.8 (12)	C29—N1—C25—C26	176.2 (12)
F1—C2—C3—C9	5.0 (13)	C25—N1—C27—C28	59.9 (13)
C1—C2—C3—C9	−174.5 (9)	C31—N1—C27—C28	−175.8 (11)
C2—C3—C4—F2	179.6 (7)	C29—N1—C27—C28	−54.6 (14)
C9—C3—C4—F2	−5.1 (12)	C25—N1—C29—C30	−179.5 (12)
C2—C3—C4—C5	−2.1 (13)	C27—N1—C29—C30	−60.1 (15)
C9—C3—C4—C5	173.2 (9)	C31—N1—C29—C30	58.9 (14)
F2—C4—C5—C6	−179.6 (7)	C25—N1—C31—C32	−51.3 (14)
C3—C4—C5—C6	2.2 (13)	C27—N1—C31—C32	−174.9 (11)
F2—C4—C5—C11	3.3 (12)	C29—N1—C31—C32	64.8 (14)
C3—C4—C5—C11	−174.9 (8)	N1—C31—C32—C33'	−170 (3)
C2—C1—C6—F3	179.2 (8)	N1—C31—C32—C33	−157.6 (14)
C7—C1—C6—F3	0.9 (12)	C31—C32—C33—C34	177 (2)
C2—C1—C6—C5	−0.1 (13)	C31—C32—C33'—C34'	86 (6)
C7—C1—C6—C5	−178.4 (8)	C41—N2—C35—C36	45 (2)
C4—C5—C6—F3	179.7 (7)	C37—N2—C35—C36	−66 (2)
C11—C5—C6—F3	−3.3 (12)	C39—N2—C35—C36	165 (3)
C4—C5—C6—C1	−1.0 (12)	C41—N2—C35—C36'	79 (2)
C11—C5—C6—C1	176.1 (8)	C39'—N2—C35—C36'	−161 (4)
C18—C13—C14—F4	−179.7 (8)	C37'—N2—C35—C36'	−52 (3)
C19—C13—C14—F4	5.3 (13)	C41—N2—C37—C38	171 (2)
C18—C13—C14—C15	0.9 (13)	C39—N2—C37—C38	50 (3)
C19—C13—C14—C15	−174.1 (9)	C35—N2—C37—C38	−70 (2)
F4—C14—C15—C16	179.8 (7)	C41—N2—C37'—C38'	172 (2)
C13—C14—C15—C16	−0.8 (13)	C35—N2—C37'—C38'	−53 (3)
F4—C14—C15—C21	−1.8 (13)	C39'—N2—C37'—C38'	48 (3)
C13—C14—C15—C21	177.6 (8)	C41—N2—C39—C40	−56 (3)
C14—C15—C16—F5	178.9 (7)	C37—N2—C39—C40	63 (4)
C21—C15—C16—F5	0.4 (13)	C35—N2—C39—C40	−179 (2)
C14—C15—C16—C17	0.9 (13)	C41—N2—C39'—C40'	−62 (5)
C21—C15—C16—C17	−177.5 (8)	C35—N2—C39'—C40'	−179 (4)
F5—C16—C17—C18	−179.0 (7)	C37'—N2—C39'—C40'	55 (5)
C15—C16—C17—C18	−1.0 (13)	C37—N2—C41—C42	161.4 (17)
F5—C16—C17—C23	−2.8 (12)	C39—N2—C41—C42	−69.4 (19)
C15—C16—C17—C23	175.1 (8)	C35—N2—C41—C42	50.6 (12)
C14—C13—C18—F6	177.9 (7)	C39'—N2—C41—C42	−54 (2)
C19—C13—C18—F6	−7.0 (13)	C37'—N2—C41—C42	−169.9 (19)
C14—C13—C18—C17	−1.0 (13)	N2—C41—C42—C43	175.2 (9)
C19—C13—C18—C17	174.1 (9)	C41—C42—C43—C44	175.8 (11)
C16—C17—C18—F6	−177.8 (7)

(1c) top

Crystal data top

C₁₉H₁₈P·2(C₁₂F₃I₃)·2(C₂H3N)·Br	D_x = 2.019 Mg m⁻³
M_r = 1602.96	Melting point: 363 K
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.6026 (12) Å	Cell parameters from 9864 reflections
b = 16.3599 (19) Å	θ = 2.3–26.4°
c = 30.679 (4) Å	µ = 4.38 mm⁻¹
β = 97.626 (5)°	T = 200 K
V = 5274.5 (11) Å³	Plate, colourless
Z = 4	0.22 × 0.11 × 0.01 mm
F(000) = 2968

Data collection top

Bruker APEX-II CCD diffractometer	4060 reflections with I > 2σ(I)
φ and ω scans	θ_max = 26.6°, θ_min = 1.3°
Absorption correction: multi-scan TWINABS	h = −13→13
T_min = 0.335, T_max = 0.745	k = 0→20
5572 measured reflections	l = 0→38
5572 independent reflections

Refinement top

Refinement on F²	441 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.141	H-atom parameters constrained
wR(F²) = 0.384	w = 1/[σ²(F_o²) + (0.180P)² + 600.5853P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
5572 reflections	Δρ_max = 2.99 e Å⁻³
294 parameters	Δρ_min = −1.62 e Å⁻³

Special details top

Experimental. Data collection is performed with three batch runs at phi = 0.00 deg (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg (650 frames). Frame width = 0.30 deg in omega. Data is merged, corrected for decay (if any), and treated with multi-scan absorption corrections (if required). All symmetry-equivalent reflections are merged for centrosymmetric data. Friedel pairs are not merged for noncentrosymmetric data.

Refinement. Refined as a 2-component twin.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
I1	0.04669 (17)	0.84506 (10)	0.34582 (5)	0.0573 (5)
I2	0.24647 (16)	0.33690 (9)	0.55382 (6)	0.0555 (5)
I3	0.04589 (17)	0.91568 (10)	0.68021 (6)	0.0561 (5)
Br1	1.0000	0.9393 (2)	0.2500	0.0527 (9)
P1	0.5000	0.9028 (7)	0.2500	0.076 (3)
F1	0.1334 (15)	0.6001 (8)	0.4558 (5)	0.058 (3)
F2	0.1208 (14)	0.6254 (9)	0.6070 (4)	0.058 (3)
F3	0.0625 (14)	0.8553 (8)	0.5170 (5)	0.057 (3)
N1	0.706 (4)	0.8390 (19)	0.4222 (12)	0.103 (9)
C1	0.0923 (18)	0.7325 (12)	0.4848 (7)	0.038 (3)
C2	0.119 (2)	0.6443 (13)	0.4915 (8)	0.044 (4)
C3	0.1286 (19)	0.6081 (13)	0.5315 (7)	0.041 (3)
C4	0.113 (2)	0.6582 (14)	0.5673 (8)	0.046 (4)
C5	0.089 (2)	0.7405 (14)	0.5659 (8)	0.048 (4)
C6	0.082 (2)	0.7736 (14)	0.5214 (8)	0.047 (4)
C7	0.077 (2)	0.7640 (13)	0.4413 (8)	0.046 (4)
C8	0.074 (3)	0.7944 (16)	0.4056 (8)	0.060 (6)
C9	0.168 (2)	0.5225 (14)	0.5374 (8)	0.050 (5)
C10	0.196 (2)	0.4543 (13)	0.5431 (7)	0.043 (5)
C11	0.087 (2)	0.7909 (16)	0.6030 (8)	0.055 (5)
C12	0.066 (2)	0.8336 (14)	0.6334 (8)	0.046 (5)
C13	0.4787 (17)	0.9675 (10)	0.2955 (5)	0.055 (4)
C14	0.3605 (13)	0.9883 (11)	0.3070 (6)	0.062 (5)
H14A	0.2856	0.9633	0.2925	0.074*
C15	0.3519 (13)	1.0457 (13)	0.3399 (7)	0.083 (8)
H15A	0.2711	1.0599	0.3479	0.100*
C16	0.4614 (17)	1.0823 (12)	0.3612 (6)	0.071 (6)
H16A	0.4555	1.1215	0.3837	0.086*
C17	0.5796 (14)	1.0614 (12)	0.3496 (6)	0.070 (6)
H17A	0.6545	1.0864	0.3641	0.084*
C18	0.5883 (13)	1.0040 (12)	0.3167 (7)	0.078 (7)
H18A	0.6691	0.9898	0.3088	0.094*
C19	0.605 (3)	0.8301 (18)	0.2607 (11)	0.063 (7)	0.5
C20	0.663 (3)	0.8021 (19)	0.2254 (9)	0.055 (7)	0.5
H20A	0.6370	0.8233	0.1967	0.066*	0.5
C23	0.758 (4)	0.7431 (19)	0.2319 (10)	0.068 (9)	0.5
H23A	0.7969	0.7240	0.2078	0.082*	0.5
C24	0.795 (3)	0.7122 (19)	0.2738 (12)	0.068 (9)	0.5
H24A	0.8601	0.6719	0.2783	0.081*	0.5
C25	0.738 (3)	0.740 (2)	0.3092 (9)	0.066 (9)	0.5
H25A	0.7633	0.7190	0.3378	0.079*	0.5
C26	0.643 (3)	0.799 (2)	0.3026 (10)	0.057 (8)	0.5
H26A	0.6033	0.8182	0.3268	0.069*	0.5
C27	0.344 (7)	0.843 (4)	0.236 (2)	0.081 (13)	0.5
H27A	0.2735	0.8808	0.2290	0.121*	0.5
H27B	0.3508	0.8070	0.2108	0.121*	0.5
H27C	0.3297	0.8091	0.2615	0.121*	0.5
C29	0.776 (4)	0.8917 (19)	0.4272 (12)	0.080 (8)
C30	0.866 (3)	0.9642 (18)	0.4387 (12)	0.083 (9)
H30A	0.9416	0.9580	0.4236	0.125*
H30B	0.8924	0.9657	0.4705	0.125*
H30C	0.8224	1.0152	0.4293	0.125*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0661 (11)	0.0482 (9)	0.0560 (10)	−0.0016 (8)	0.0028 (8)	0.0069 (7)
I2	0.0562 (10)	0.0359 (8)	0.0714 (11)	0.0071 (7)	−0.0022 (8)	0.0013 (7)
I3	0.0654 (11)	0.0433 (9)	0.0575 (10)	−0.0009 (7)	0.0010 (7)	−0.0096 (7)
Br1	0.071 (2)	0.0371 (16)	0.0491 (18)	0.000	0.0047 (16)	0.000
P1	0.109 (8)	0.046 (5)	0.074 (6)	0.000	0.017 (5)	0.000
F1	0.076 (9)	0.041 (6)	0.055 (6)	0.011 (6)	0.000 (6)	−0.001 (5)
F2	0.066 (9)	0.052 (7)	0.049 (6)	0.009 (6)	−0.009 (5)	0.005 (5)
F3	0.066 (9)	0.038 (5)	0.061 (7)	0.001 (5)	−0.010 (6)	−0.004 (4)
N1	0.122 (19)	0.065 (13)	0.12 (2)	0.010 (13)	0.006 (17)	0.016 (15)
C1	0.023 (8)	0.035 (5)	0.052 (5)	−0.003 (5)	−0.010 (5)	−0.002 (4)
C2	0.040 (10)	0.035 (6)	0.053 (6)	0.001 (5)	−0.003 (5)	−0.002 (4)
C3	0.029 (9)	0.039 (5)	0.053 (6)	0.000 (5)	−0.007 (5)	0.000 (4)
C4	0.042 (10)	0.043 (6)	0.049 (6)	0.002 (5)	−0.010 (5)	−0.001 (4)
C5	0.045 (10)	0.043 (6)	0.050 (6)	0.002 (5)	−0.015 (5)	−0.004 (4)
C6	0.046 (11)	0.037 (6)	0.052 (6)	0.003 (5)	−0.011 (5)	−0.003 (4)
C7	0.054 (12)	0.031 (8)	0.051 (6)	−0.003 (8)	−0.009 (6)	−0.006 (5)
C8	0.077 (16)	0.048 (11)	0.051 (6)	−0.016 (11)	−0.012 (7)	0.001 (7)
C9	0.046 (11)	0.038 (5)	0.059 (10)	0.003 (5)	−0.017 (9)	−0.004 (5)
C10	0.043 (11)	0.036 (6)	0.049 (11)	0.004 (6)	0.003 (9)	0.000 (6)
C11	0.055 (12)	0.050 (9)	0.058 (7)	−0.002 (8)	−0.007 (7)	−0.009 (6)
C12	0.042 (11)	0.040 (9)	0.053 (8)	0.006 (8)	−0.011 (7)	−0.001 (7)
C13	0.063 (8)	0.042 (8)	0.057 (8)	0.004 (6)	−0.002 (6)	0.008 (6)
C14	0.062 (9)	0.057 (11)	0.062 (10)	0.007 (7)	−0.007 (7)	0.001 (8)
C15	0.054 (9)	0.094 (15)	0.097 (13)	0.009 (8)	−0.009 (8)	−0.034 (12)
C16	0.057 (9)	0.079 (13)	0.073 (12)	0.009 (8)	−0.011 (8)	−0.012 (11)
C17	0.055 (9)	0.073 (13)	0.078 (12)	0.004 (8)	−0.009 (8)	−0.011 (10)
C18	0.065 (9)	0.079 (13)	0.088 (12)	0.000 (8)	0.001 (8)	−0.019 (11)
C19	0.092 (13)	0.037 (11)	0.063 (11)	−0.009 (9)	0.023 (9)	0.009 (8)
C20	0.079 (15)	0.026 (12)	0.063 (12)	−0.019 (11)	0.020 (10)	0.005 (9)
C23	0.091 (17)	0.042 (15)	0.076 (15)	−0.005 (13)	0.027 (12)	0.013 (11)
C24	0.088 (17)	0.043 (15)	0.076 (15)	−0.009 (14)	0.027 (13)	0.015 (12)
C25	0.082 (17)	0.045 (15)	0.074 (14)	−0.010 (13)	0.023 (11)	0.014 (11)
C26	0.075 (16)	0.039 (14)	0.061 (12)	−0.016 (12)	0.022 (10)	0.009 (9)
C27	0.100 (14)	0.057 (19)	0.09 (3)	−0.004 (11)	0.019 (12)	−0.024 (19)
C29	0.095 (17)	0.046 (11)	0.10 (2)	0.034 (10)	0.008 (15)	0.015 (12)
C30	0.086 (17)	0.049 (11)	0.12 (2)	0.035 (11)	0.035 (15)	−0.011 (14)

Geometric parameters (Å, º) top

I1—C8	2.00 (3)	C14—H14A	0.9500
I2—C10	2.01 (2)	C15—C16	1.3900
I3—C12	2.00 (2)	C15—H15A	0.9500
P1—C19	1.63 (3)	C16—C17	1.3900
P1—C13ⁱ	1.788 (14)	C16—H16A	0.9500
P1—C13	1.789 (14)	C17—C18	1.3900
P1—C27	1.92 (7)	C17—H17A	0.9500
F1—C2	1.34 (3)	C18—H18A	0.9500
F2—C4	1.32 (3)	C19—C20	1.3900
F3—C6	1.36 (3)	C19—C26	1.3900
N1—C29	1.13 (5)	C20—C23	1.3900
C1—C6	1.32 (3)	C20—H20A	0.9500
C1—C7	1.42 (3)	C23—C24	1.3900
C1—C2	1.48 (3)	C23—H23A	0.9500
C2—C3	1.36 (3)	C24—C25	1.3900
C3—C4	1.40 (3)	C24—H24A	0.9500
C3—C9	1.46 (3)	C25—C26	1.3900
C4—C5	1.37 (3)	C25—H25A	0.9500
C5—C11	1.41 (3)	C26—H26A	0.9500
C5—C6	1.46 (3)	C27—H27A	0.9800
C7—C8	1.20 (3)	C27—H27B	0.9800
C9—C10	1.16 (3)	C27—H27C	0.9800
C11—C12	1.21 (3)	C29—C30	1.53 (5)
C13—C14	1.3900	C30—H30A	0.9800
C13—C18	1.3900	C30—H30B	0.9800
C14—C15	1.3900	C30—H30C	0.9800

C19—P1—C13ⁱ	115.8 (13)	C15—C16—H16A	120.0
C19—P1—C13	115.3 (14)	C17—C16—H16A	120.0
C13ⁱ—P1—C13	107.4 (13)	C16—C17—C18	120.0
C19—P1—C27	102 (3)	C16—C17—H17A	120.0
C13ⁱ—P1—C27	109 (2)	C18—C17—H17A	120.0
C13—P1—C27	106 (2)	C17—C18—C13	120.0
C6—C1—C7	127 (2)	C17—C18—H18A	120.0
C6—C1—C2	114 (2)	C13—C18—H18A	120.0
C7—C1—C2	118.7 (19)	C20—C19—C26	120.0
F1—C2—C3	120.2 (19)	C20—C19—P1	116 (2)
F1—C2—C1	117.0 (19)	C26—C19—P1	124 (2)
C3—C2—C1	123 (2)	C23—C20—C19	120.0
C2—C3—C4	117 (2)	C23—C20—H20A	120.0
C2—C3—C9	121 (2)	C19—C20—H20A	120.0
C4—C3—C9	122 (2)	C24—C23—C20	120.0
F2—C4—C5	115 (2)	C24—C23—H23A	120.0
F2—C4—C3	119 (2)	C20—C23—H23A	120.0
C5—C4—C3	127 (2)	C25—C24—C23	120.0
C4—C5—C11	125 (2)	C25—C24—H24A	120.0
C4—C5—C6	112 (2)	C23—C24—H24A	120.0
C11—C5—C6	122 (2)	C24—C25—C26	120.0
C1—C6—F3	116 (2)	C24—C25—H25A	120.0
C1—C6—C5	127 (2)	C26—C25—H25A	120.0
F3—C6—C5	116 (2)	C25—C26—C19	120.0
C8—C7—C1	174 (3)	C25—C26—H26A	120.0
C7—C8—I1	173 (3)	C19—C26—H26A	120.0
C10—C9—C3	178 (3)	P1—C27—H27A	109.5
C9—C10—I2	179 (2)	P1—C27—H27B	109.5
C12—C11—C5	170 (3)	H27A—C27—H27B	109.5
C11—C12—I3	172 (2)	P1—C27—H27C	109.5
C14—C13—C18	120.0	H27A—C27—H27C	109.5
C14—C13—P1	123.8 (10)	H27B—C27—H27C	109.5
C18—C13—P1	115.9 (10)	N1—C29—C30	174 (4)
C13—C14—C15	120.0	C29—C30—H30A	109.5
C13—C14—H14A	120.0	C29—C30—H30B	109.5
C15—C14—H14A	120.0	H30A—C30—H30B	109.5
C16—C15—C14	120.0	C29—C30—H30C	109.5
C16—C15—H15A	120.0	H30A—C30—H30C	109.5
C14—C15—H15A	120.0	H30B—C30—H30C	109.5
C15—C16—C17	120.0

C6—C1—C2—F1	−178.3 (19)	C27—P1—C13—C14	−19 (3)
C7—C1—C2—F1	3 (3)	C19—P1—C13—C18	54.4 (18)
C6—C1—C2—C3	2 (3)	C13ⁱ—P1—C13—C18	−76.3 (10)
C7—C1—C2—C3	−176 (2)	C27—P1—C13—C18	167 (3)
F1—C2—C3—C4	179.9 (19)	C18—C13—C14—C15	0.0
C1—C2—C3—C4	−1 (3)	P1—C13—C14—C15	−173.2 (15)
F1—C2—C3—C9	7 (3)	C13—C14—C15—C16	0.0
C1—C2—C3—C9	−174.0 (19)	C14—C15—C16—C17	0.0
C2—C3—C4—F2	179.8 (19)	C15—C16—C17—C18	0.0
C9—C3—C4—F2	−7 (3)	C16—C17—C18—C13	0.0
C2—C3—C4—C5	0 (4)	C14—C13—C18—C17	0.0
C9—C3—C4—C5	173 (2)	P1—C13—C18—C17	173.7 (14)
F2—C4—C5—C11	7 (4)	C13ⁱ—P1—C19—C20	−27 (2)
C3—C4—C5—C11	−173 (2)	C13—P1—C19—C20	−153.8 (16)
F2—C4—C5—C6	179.5 (19)	C27—P1—C19—C20	91 (3)
C3—C4—C5—C6	−1 (3)	C13ⁱ—P1—C19—C26	149.5 (17)
C7—C1—C6—F3	−4 (3)	C13—P1—C19—C26	23 (3)
C2—C1—C6—F3	177.6 (18)	C27—P1—C19—C26	−92 (3)
C7—C1—C6—C5	175 (2)	C26—C19—C20—C23	0.0
C2—C1—C6—C5	−3 (3)	P1—C19—C20—C23	177 (3)
C4—C5—C6—C1	2 (4)	C19—C20—C23—C24	0.0
C11—C5—C6—C1	175 (2)	C20—C23—C24—C25	0.0
C4—C5—C6—F3	−178 (2)	C23—C24—C25—C26	0.0
C11—C5—C6—F3	−6 (3)	C24—C25—C26—C19	0.0
C19—P1—C13—C14	−132.1 (17)	C20—C19—C26—C25	0.0
C13ⁱ—P1—C13—C14	97.2 (13)	P1—C19—C26—C25	−177 (3)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C30—H30A···I1ⁱⁱ	0.98	3.33	4.13 (3)	140
C30—H30A···I1ⁱⁱ	0.98	3.33	4.13 (3)	140

Symmetry code: (ii) x+1, y, z.

(1d) top

Crystal data top

C₂₀H₂₀P·2(C₁₂F₃I₃)·Br	Melting point: 413 K
M_r = 3069.76	Mo Kα radiation, λ = 0.71073 Å
Cubic, Pa3	Cell parameters from 9918 reflections
a = 22.3941 (15) Å	θ = 2.2–24.6°
V = 11231 (2) Å³	µ = 4.10 mm⁻¹
Z = 4	T = 200 K
F(000) = 5648	Block, colourless
D_x = 1.816 Mg m⁻³ D_m = n/a Mg m⁻³ D_m measured by ?	0.24 × 0.18 × 0.12 mm

Data collection top

Bruker APEX-II CCD diffractometer	3422 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.045
Absorption correction: multi-scan SADABS, Bruker (2003)	θ_max = 28.3°, θ_min = 1.8°
T_min = 0.556, T_max = 0.746	h = −29→29
96410 measured reflections	k = −24→29
4615 independent reflections	l = −29→29

Refinement top

Refinement on F²	12 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.062	H-atom parameters constrained
wR(F²) = 0.191	w = 1/[σ²(F_o²) + (0.1046P)² + 30.8424P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
4615 reflections	Δρ_max = 2.20 e Å⁻³
146 parameters	Δρ_min = −1.08 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
I1	0.37460 (2)	0.81077 (3)	0.21602 (3)	0.0821 (2)
I2	0.10622 (2)	0.73126 (3)	0.29179 (3)	0.0839 (3)
Br1	0.24426 (3)	0.75574 (3)	0.25574 (3)	0.0440 (2)
F1	0.5388 (2)	0.8050 (2)	0.0588 (2)	0.0874 (15)
F2	−0.0831 (2)	0.7245 (2)	0.4279 (2)	0.0790 (13)
C1	0.5686 (3)	0.8529 (3)	0.0790 (3)	0.0613 (17)
C2	0.5473 (3)	0.8821 (4)	0.1278 (3)	0.0643 (18)
C3	0.4936 (3)	0.8628 (4)	0.1586 (4)	0.072 (2)
C4	0.4502 (4)	0.8442 (5)	0.1814 (4)	0.083 (3)
C5	−0.1049 (3)	0.6764 (3)	0.3995 (3)	0.0555 (15)
C6	−0.0754 (3)	0.6563 (3)	0.3501 (3)	0.0571 (15)
C7	−0.0227 (3)	0.6823 (4)	0.3290 (4)	0.070 (2)
C8	0.0235 (4)	0.7035 (5)	0.3158 (4)	0.083 (3)
P1	0.4972 (4)	0.3575 (4)	0.1094 (3)	0.091 (2)	0.3333
C9	0.5224 (15)	0.2827 (8)	0.1157 (15)	0.139 (3)*	0.3333
C10	0.5583 (14)	0.2563 (12)	0.0725 (12)	0.139 (3)*	0.3333
H10	0.5735	0.2796	0.0404	0.166*	0.3333
C11	0.5719 (12)	0.1958 (12)	0.0761 (12)	0.139 (3)*	0.3333
H11	0.5965	0.1778	0.0466	0.166*	0.3333
C12	0.5496 (15)	0.1618 (8)	0.1230 (15)	0.139 (3)*	0.3333
H12	0.5589	0.1205	0.1255	0.166*	0.3333
C13	0.5137 (14)	0.1882 (12)	0.1662 (13)	0.139 (3)*	0.3333
H13	0.4985	0.1649	0.1982	0.166*	0.3333
C14	0.5001 (12)	0.2487 (13)	0.1625 (13)	0.139 (3)*	0.3333
H14	0.4756	0.2667	0.1921	0.166*	0.3333
C15	0.5566 (11)	0.4001 (13)	0.0791 (13)	0.139 (3)*	0.3333
C16	0.6063 (14)	0.4045 (13)	0.1159 (10)	0.139 (3)*	0.3333
H16	0.6069	0.3843	0.1532	0.166*	0.3333
C17	0.6551 (11)	0.4385 (15)	0.0983 (13)	0.139 (3)*	0.3333
H17	0.6891	0.4416	0.1235	0.166*	0.3333
C18	0.6542 (11)	0.4681 (13)	0.0437 (14)	0.139 (3)*	0.3333
H18	0.6876	0.4913	0.0316	0.166*	0.3333
C19	0.6045 (14)	0.4636 (12)	0.0068 (11)	0.139 (3)*	0.3333
H19	0.6039	0.4838	−0.0305	0.166*	0.3333
C20	0.5557 (10)	0.4296 (14)	0.0245 (12)	0.139 (3)*	0.3333
H20	0.5217	0.4266	−0.0007	0.166*	0.3333
C21	0.4328 (11)	0.3592 (15)	0.0646 (11)	0.139 (3)*	0.3333
C22	0.4292 (13)	0.3194 (14)	0.0171 (13)	0.139 (3)*	0.3333
H22	0.4587	0.2892	0.0123	0.166*	0.3333
C23	0.3824 (16)	0.3237 (15)	−0.0235 (11)	0.139 (3)*	0.3333
H23	0.3799	0.2965	−0.0559	0.166*	0.3333
C24	0.3393 (13)	0.3678 (16)	−0.0165 (13)	0.139 (3)*	0.3333
H24	0.3073	0.3707	−0.0443	0.166*	0.3333
C25	0.3429 (13)	0.4075 (14)	0.0310 (14)	0.139 (3)*	0.3333
H25	0.3134	0.4377	0.0357	0.166*	0.3333
C26	0.3897 (14)	0.4032 (13)	0.0715 (12)	0.139 (3)*	0.3333
H26	0.3922	0.4304	0.1040	0.166*	0.3333
C27	0.4797 (12)	0.3847 (14)	0.1818 (11)	0.139 (3)*	0.3333
H27A	0.5098	0.3724	0.2118	0.166*	0.3333
H27B	0.4751	0.4286	0.1824	0.166*	0.3333
C28	0.4207 (12)	0.3529 (14)	0.1907 (16)	0.139 (3)*	0.3333
H28A	0.4052	0.3618	0.2306	0.208*	0.3333
H28B	0.4267	0.3097	0.1866	0.208*	0.3333
H28C	0.3921	0.3666	0.1605	0.208*	0.3333

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0580 (3)	0.0951 (4)	0.0932 (4)	−0.0150 (3)	0.0273 (3)	−0.0025 (3)
I2	0.0566 (3)	0.1071 (5)	0.0878 (4)	−0.0311 (3)	0.0217 (3)	−0.0206 (3)
Br1	0.0440 (2)	0.0440 (2)	0.0440 (2)	−0.0052 (2)	−0.0052 (2)	0.0052 (2)
F1	0.095 (3)	0.077 (3)	0.091 (3)	−0.039 (3)	0.014 (3)	−0.033 (3)
F2	0.077 (3)	0.082 (3)	0.078 (3)	−0.032 (2)	0.012 (2)	−0.035 (2)
C1	0.058 (4)	0.062 (4)	0.065 (4)	−0.022 (3)	0.014 (3)	−0.018 (3)
C2	0.057 (4)	0.075 (4)	0.061 (4)	−0.013 (3)	0.018 (3)	−0.013 (3)
C3	0.059 (4)	0.083 (5)	0.073 (5)	−0.014 (4)	0.017 (4)	−0.011 (4)
C4	0.062 (4)	0.102 (6)	0.085 (6)	−0.022 (4)	0.028 (4)	−0.012 (5)
C5	0.053 (3)	0.057 (4)	0.057 (4)	−0.013 (3)	0.003 (3)	−0.012 (3)
C6	0.051 (3)	0.058 (4)	0.062 (4)	−0.011 (3)	0.008 (3)	−0.011 (3)
C7	0.055 (4)	0.080 (5)	0.074 (5)	−0.012 (4)	0.011 (3)	−0.017 (4)
C8	0.060 (4)	0.098 (6)	0.092 (6)	−0.033 (4)	0.017 (4)	−0.025 (5)
P1	0.108 (6)	0.107 (6)	0.059 (4)	−0.013 (5)	0.030 (4)	−0.024 (4)

Geometric parameters (Å, º) top

I1—C4	2.007 (7)	C9—C14	1.3900
I2—C8	2.027 (8)	C10—C11	1.3900
F1—C1	1.343 (7)	C11—C12	1.3900
F2—C5	1.344 (7)	C12—C13	1.3900
C1—C2	1.360 (10)	C13—C14	1.3900
C1—C2ⁱ	1.381 (10)	C15—C16	1.3900
C2—C1ⁱⁱ	1.381 (10)	C15—C20	1.3900
C2—C3	1.452 (10)	C16—C17	1.3900
C3—C4	1.174 (10)	C17—C18	1.3900
C5—C6	1.367 (9)	C18—C19	1.3900
C5—C6ⁱⁱⁱ	1.410 (9)	C19—C20	1.3900
C6—C7	1.398 (10)	C21—C22	1.3900
C6—C5^iv	1.410 (9)	C21—C26	1.3900
C7—C8	1.176 (11)	C22—C23	1.3900
P1—C21	1.756 (18)	C23—C24	1.3900
P1—C15	1.771 (17)	C24—C25	1.3900
P1—C9	1.775 (17)	C25—C26	1.3900
P1—C27	1.78 (2)	C27—C28	1.514 (19)
C9—C10	1.3900

F1—C1—C2	118.7 (6)	C14—C9—P1	118 (2)
F1—C1—C2ⁱ	118.2 (6)	C11—C10—C9	120.0
C2—C1—C2ⁱ	123.0 (7)	C10—C11—C12	120.0
C1—C2—C1ⁱⁱ	116.9 (7)	C11—C12—C13	120.0
C1—C2—C3	122.0 (7)	C14—C13—C12	120.0
C1ⁱⁱ—C2—C3	121.1 (7)	C13—C14—C9	120.0
C4—C3—C2	176.0 (9)	C16—C15—C20	120.0
C3—C4—I1	176.8 (9)	C16—C15—P1	114.3 (19)
F2—C5—C6	118.1 (6)	C20—C15—P1	126 (2)
F2—C5—C6ⁱⁱⁱ	116.5 (6)	C17—C16—C15	120.0
C6—C5—C6ⁱⁱⁱ	125.4 (6)	C18—C17—C16	120.0
C5—C6—C7	123.1 (6)	C17—C18—C19	120.0
C5—C6—C5^iv	114.6 (6)	C20—C19—C18	120.0
C7—C6—C5^iv	122.2 (6)	C19—C20—C15	120.0
C8—C7—C6	174.5 (10)	C22—C21—C26	120.0
C7—C8—I2	174.1 (9)	C22—C21—P1	118 (2)
C21—P1—C15	112.7 (16)	C26—C21—P1	121 (2)
C21—P1—C9	109.0 (16)	C21—C22—C23	120.0
C15—P1—C9	107.4 (16)	C22—C23—C24	120.0
C21—P1—C27	109.6 (10)	C25—C24—C23	120.0
C15—P1—C27	109.4 (10)	C24—C25—C26	120.0
C9—P1—C27	108.7 (11)	C25—C26—C21	120.0
C10—C9—C14	120.0	C28—C27—P1	98.7 (18)
C10—C9—P1	122.1 (19)

F1—C1—C2—C1ⁱⁱ	−179.7 (5)	C27—P1—C15—C20	−125 (2)
C2ⁱ—C1—C2—C1ⁱⁱ	−3.2 (18)	C20—C15—C16—C17	0.0
F1—C1—C2—C3	0.1 (13)	P1—C15—C16—C17	−178 (2)
C2ⁱ—C1—C2—C3	176.6 (6)	C15—C16—C17—C18	0.0
F2—C5—C6—C7	1.9 (12)	C16—C17—C18—C19	0.0
C6ⁱⁱⁱ—C5—C6—C7	−176.3 (6)	C17—C18—C19—C20	0.0
F2—C5—C6—C5^iv	178.8 (4)	C18—C19—C20—C15	0.0
C6ⁱⁱⁱ—C5—C6—C5^iv	0.6 (15)	C16—C15—C20—C19	0.0
C21—P1—C9—C10	84 (2)	P1—C15—C20—C19	177 (2)
C15—P1—C9—C10	−39 (2)	C15—P1—C21—C22	84 (2)
C27—P1—C9—C10	−156.9 (16)	C9—P1—C21—C22	−35 (2)
C21—P1—C9—C14	−90 (2)	C27—P1—C21—C22	−154.1 (16)
C15—P1—C9—C14	147.8 (17)	C15—P1—C21—C26	−89 (2)
C27—P1—C9—C14	30 (2)	C9—P1—C21—C26	152.2 (19)
C14—C9—C10—C11	0.0	C27—P1—C21—C26	33 (2)
P1—C9—C10—C11	−173 (3)	C26—C21—C22—C23	0.0
C9—C10—C11—C12	0.0	P1—C21—C22—C23	−173 (2)
C10—C11—C12—C13	0.0	C21—C22—C23—C24	0.0
C11—C12—C13—C14	0.0	C22—C23—C24—C25	0.0
C12—C13—C14—C9	0.0	C23—C24—C25—C26	0.0
C10—C9—C14—C13	0.0	C24—C25—C26—C21	0.0
P1—C9—C14—C13	174 (2)	C22—C21—C26—C25	0.0
C21—P1—C15—C16	174.2 (16)	P1—C21—C26—C25	172 (2)
C9—P1—C15—C16	−66 (2)	C21—P1—C27—C28	43 (2)
C27—P1—C15—C16	52.1 (19)	C15—P1—C27—C28	166.9 (18)
C21—P1—C15—C20	−3 (3)	C9—P1—C27—C28	−76 (2)
C9—P1—C15—C20	117 (2)

Symmetry codes: (i) −y+3/2, −z+1, x−1/2; (ii) z+1/2, −x+3/2, −y+1; (iii) −y+1/2, −z+1, x+1/2; (iv) z−1/2, −x+1/2, −y+1.

(1e) top

Crystal data top

C₂₁H₂₀OP·2(C₁₂F₃I₃)·2(C₂H₃N)·Br	D_x = 2.074 Mg m⁻³ D_m = n/a Mg m⁻³ D_m measured by ?
M_r = 1645.00	Melting point: 415 K
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.5098 (5) Å	Cell parameters from 9992 reflections
b = 16.2789 (7) Å	θ = 2.3–28.3°
c = 30.9417 (15) Å	µ = 4.39 mm⁻¹
β = 95.6557 (19)°	T = 200 K
V = 5268.0 (4) Å³	Block, colourless
Z = 4	0.15 × 0.11 × 0.10 mm
F(000) = 3056

Data collection top

Bruker APEX-II CCD diffractometer	6031 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.039
Absorption correction: multi-scan SADABS, Bruker (2003)	θ_max = 28.5°, θ_min = 1.3°
T_min = 0.601, T_max = 0.746	h = −14→13
35395 measured reflections	k = −21→21
6513 independent reflections	l = −41→41

Refinement top

Refinement on F²	135 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.066	H-atom parameters constrained
wR(F²) = 0.155	w = 1/[σ²(F_o²) + (0.0297P)² + 174.9186P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
6513 reflections	Δρ_max = 1.35 e Å⁻³
333 parameters	Δρ_min = −1.78 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
I1	0.03499 (6)	0.91655 (4)	0.17890 (2)	0.04371 (16)
I2	0.04897 (6)	0.84508 (4)	−0.15360 (2)	0.04458 (16)
I3	0.24286 (6)	0.33895 (4)	0.05260 (2)	0.04930 (18)
Br1	0.0000	1.06383 (8)	0.2500	0.0454 (3)
P1	−0.5000	1.0970 (3)	0.2500	0.0789 (16)
F1	0.0599 (6)	0.8584 (3)	0.01623 (18)	0.0460 (13)
F2	0.1342 (6)	0.6019 (3)	−0.04406 (16)	0.0462 (13)
F3	0.1207 (7)	0.6282 (3)	0.10592 (17)	0.0538 (15)
C1	0.0863 (8)	0.7449 (5)	0.0629 (3)	0.0367 (18)
C2	0.0807 (8)	0.7769 (5)	0.0215 (3)	0.0342 (17)
C3	0.0912 (8)	0.7310 (5)	−0.0161 (3)	0.0344 (17)
C4	0.1172 (8)	0.6476 (5)	−0.0092 (3)	0.0349 (17)
C5	0.1286 (9)	0.6106 (6)	0.0315 (3)	0.0390 (18)
C6	0.1115 (8)	0.6616 (6)	0.0665 (3)	0.0374 (18)
C7	0.0759 (9)	0.7952 (6)	0.1006 (3)	0.042 (2)
C8	0.0626 (10)	0.8383 (6)	0.1304 (3)	0.044 (2)
C9	0.0814 (8)	0.7670 (5)	−0.0585 (3)	0.0368 (18)
C10	0.0721 (10)	0.7952 (6)	−0.0937 (3)	0.043 (2)
C11	0.1617 (9)	0.5253 (6)	0.0368 (3)	0.042 (2)
C12	0.1919 (9)	0.4560 (6)	0.0417 (3)	0.0413 (19)
C13	−0.4851 (12)	1.0309 (6)	0.2044 (3)	0.054 (3)
C14	−0.3678 (12)	1.0134 (7)	0.1900 (4)	0.059 (3)
H14A	−0.2927	1.0402	0.2025	0.070*
C15	−0.3614 (12)	0.9563 (8)	0.1573 (4)	0.062 (3)
H15A	−0.2814	0.9451	0.1466	0.075*
C16	−0.4696 (13)	0.9155 (8)	0.1398 (4)	0.063 (3)
H16A	−0.4635	0.8746	0.1183	0.076*
C17	−0.5861 (14)	0.9343 (9)	0.1539 (4)	0.075 (4)
H17A	−0.6608	0.9074	0.1412	0.090*
C18	−0.5963 (15)	0.9922 (10)	0.1864 (5)	0.083 (4)
H18A	−0.6770	1.0050	0.1961	0.099*
C19	−0.4007 (12)	1.1721 (8)	0.2597 (4)	0.045 (3)	0.5
C20	−0.3447 (15)	1.2052 (9)	0.2248 (3)	0.054 (5)	0.5
H20A	−0.3719	1.1877	0.1960	0.065*	0.5
C21	−0.2488 (15)	1.2639 (9)	0.2318 (4)	0.051 (4)	0.5
H21A	−0.2106	1.2865	0.2079	0.061*	0.5
C22	−0.2089 (14)	1.2895 (9)	0.2738 (5)	0.048 (5)	0.5
H22A	−0.1434	1.3296	0.2786	0.058*	0.5
C23	−0.2649 (14)	1.2564 (10)	0.3088 (4)	0.056 (4)	0.5
H23A	−0.2377	1.2739	0.3375	0.067*	0.5
C24	−0.3608 (13)	1.1977 (9)	0.3017 (4)	0.052 (4)	0.5
H24A	−0.3990	1.1751	0.3256	0.062*	0.5
O1	−0.660 (3)	1.2121 (16)	0.2952 (8)	0.103 (8)	0.5
C25	−0.668 (4)	1.1538 (19)	0.2310 (12)	0.097 (7)	0.5
H25A	−0.6631	1.1776	0.2018	0.116*	0.5
H25B	−0.7371	1.1122	0.2286	0.116*	0.5
C26	−0.699 (4)	1.2125 (18)	0.2575 (11)	0.081 (6)	0.5
C27	−0.797 (4)	1.2767 (19)	0.2383 (12)	0.082 (9)	0.5
H27A	−0.8114	1.3177	0.2605	0.124*	0.5
H27B	−0.8782	1.2491	0.2289	0.124*	0.5
H27C	−0.7646	1.3038	0.2134	0.124*	0.5
N1	0.2885 (15)	1.1613 (8)	0.0787 (6)	0.108 (5)
C28	0.2256 (14)	1.1050 (8)	0.0728 (5)	0.073 (3)
C29	0.1431 (14)	1.0364 (8)	0.0630 (5)	0.079 (4)
H29A	0.0638	1.0440	0.0767	0.118*
H29B	0.1857	0.9860	0.0740	0.118*
H29C	0.1231	1.0321	0.0314	0.118*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0576 (4)	0.0391 (3)	0.0345 (3)	0.0027 (3)	0.0049 (2)	−0.0061 (2)
I2	0.0565 (4)	0.0448 (3)	0.0333 (3)	−0.0007 (3)	0.0083 (2)	0.0051 (2)
I3	0.0479 (4)	0.0344 (3)	0.0654 (4)	0.0073 (3)	0.0046 (3)	0.0015 (3)
Br1	0.0741 (9)	0.0373 (6)	0.0254 (5)	0.000	0.0079 (5)	0.000
P1	0.142 (5)	0.035 (2)	0.062 (3)	0.000	0.022 (3)	0.000
F1	0.061 (3)	0.029 (2)	0.048 (3)	0.003 (2)	0.010 (3)	0.002 (2)
F2	0.066 (4)	0.040 (3)	0.032 (2)	0.009 (3)	0.002 (2)	−0.006 (2)
F3	0.086 (4)	0.045 (3)	0.028 (2)	0.012 (3)	−0.002 (3)	0.003 (2)
C1	0.038 (4)	0.039 (4)	0.031 (4)	0.002 (3)	−0.007 (3)	−0.006 (3)
C2	0.034 (4)	0.027 (4)	0.042 (4)	0.003 (3)	0.005 (3)	−0.002 (3)
C3	0.036 (4)	0.036 (4)	0.031 (4)	−0.005 (3)	0.003 (3)	−0.001 (3)
C4	0.036 (4)	0.034 (4)	0.036 (4)	0.003 (3)	0.004 (3)	−0.003 (3)
C5	0.040 (5)	0.039 (4)	0.037 (4)	0.003 (4)	0.001 (3)	−0.002 (3)
C6	0.040 (4)	0.042 (4)	0.030 (4)	0.003 (4)	−0.002 (3)	−0.002 (3)
C7	0.046 (5)	0.040 (5)	0.040 (5)	0.005 (4)	0.000 (4)	−0.003 (4)
C8	0.052 (5)	0.037 (4)	0.040 (5)	0.004 (4)	−0.003 (4)	−0.003 (4)
C9	0.031 (4)	0.039 (4)	0.041 (4)	0.001 (3)	0.004 (3)	0.000 (4)
C10	0.057 (6)	0.037 (4)	0.035 (4)	−0.003 (4)	0.003 (4)	0.002 (4)
C11	0.039 (5)	0.047 (5)	0.040 (5)	0.007 (4)	0.002 (4)	−0.008 (4)
C12	0.040 (5)	0.040 (5)	0.044 (5)	0.007 (4)	0.000 (4)	−0.001 (4)
C13	0.083 (8)	0.044 (5)	0.037 (5)	−0.015 (5)	0.008 (5)	0.005 (4)
C14	0.069 (7)	0.048 (6)	0.055 (6)	0.005 (5)	−0.012 (5)	0.013 (5)
C15	0.062 (7)	0.065 (7)	0.059 (7)	0.013 (6)	0.006 (5)	−0.003 (6)
C16	0.085 (9)	0.065 (7)	0.039 (5)	0.008 (7)	0.006 (5)	−0.007 (5)
C17	0.080 (9)	0.087 (10)	0.059 (7)	−0.030 (8)	0.009 (6)	−0.015 (7)
C18	0.078 (9)	0.097 (11)	0.078 (9)	−0.027 (8)	0.031 (7)	−0.015 (8)
C19	0.042 (7)	0.037 (7)	0.056 (7)	0.017 (6)	0.003 (6)	0.008 (6)
C20	0.059 (10)	0.049 (10)	0.056 (8)	−0.005 (8)	0.008 (7)	−0.003 (7)
C21	0.054 (9)	0.043 (8)	0.057 (8)	−0.006 (7)	0.009 (6)	−0.005 (6)
C22	0.042 (8)	0.042 (9)	0.060 (8)	0.009 (7)	0.004 (6)	−0.011 (6)
C23	0.049 (8)	0.057 (9)	0.062 (8)	0.013 (7)	0.006 (6)	−0.004 (6)
C24	0.042 (8)	0.059 (9)	0.053 (7)	0.009 (7)	0.003 (6)	0.003 (6)
O1	0.131 (18)	0.085 (14)	0.090 (12)	0.021 (13)	0.000 (10)	−0.002 (9)
C25	0.138 (14)	0.056 (11)	0.097 (13)	0.014 (11)	0.012 (10)	0.003 (10)
C26	0.107 (14)	0.048 (10)	0.088 (12)	0.001 (10)	0.006 (10)	0.004 (9)
C27	0.108 (17)	0.041 (11)	0.094 (17)	0.001 (12)	−0.012 (14)	−0.006 (11)
N1	0.106 (9)	0.062 (6)	0.159 (14)	−0.002 (6)	0.030 (9)	0.005 (7)
C28	0.088 (8)	0.048 (5)	0.088 (9)	0.015 (5)	0.038 (7)	0.006 (5)
C29	0.101 (9)	0.050 (6)	0.093 (9)	0.011 (6)	0.048 (7)	−0.001 (6)

Geometric parameters (Å, º) top

I1—C8	2.011 (9)	C9—C10	1.177 (12)
I2—C10	2.016 (9)	C11—C12	1.178 (13)
I3—C12	1.999 (9)	C13—C14	1.381 (17)
P1—C19	1.616 (11)	C13—C18	1.395 (18)
P1—C13ⁱ	1.794 (11)	C14—C15	1.381 (16)
P1—C13	1.795 (11)	C15—C16	1.380 (17)
P1—C25	2.03 (4)	C16—C17	1.374 (18)
F1—C2	1.352 (9)	C17—C18	1.390 (19)
F2—C4	1.337 (9)	C19—C20	1.3900
F3—C6	1.330 (10)	C19—C24	1.3900
C1—C2	1.379 (12)	C20—C21	1.3900
C1—C6	1.384 (12)	C21—C22	1.3900
C1—C7	1.439 (12)	C22—C23	1.3900
C2—C3	1.397 (11)	C23—C24	1.3900
C3—C4	1.397 (12)	O1—C26	1.20 (4)
C3—C9	1.430 (12)	C25—C26	1.32 (4)
C4—C5	1.389 (12)	C26—C27	1.55 (4)
C5—C6	1.390 (12)	N1—C28	1.135 (19)
C5—C11	1.437 (13)	C28—C29	1.429 (19)
C7—C8	1.177 (13)

C19—P1—C13ⁱ	114.3 (6)	C10—C9—C3	178.6 (10)
C19—P1—C13	119.7 (6)	C9—C10—I2	177.7 (9)
C13ⁱ—P1—C13	106.3 (7)	C12—C11—C5	178.2 (11)
C19—P1—C25	103.7 (12)	C11—C12—I3	177.7 (9)
C13ⁱ—P1—C25	111.1 (11)	C14—C13—C18	121.2 (11)
C13—P1—C25	100.8 (11)	C14—C13—P1	121.8 (9)
C2—C1—C6	115.8 (8)	C18—C13—P1	116.8 (10)
C2—C1—C7	122.7 (8)	C13—C14—C15	119.0 (11)
C6—C1—C7	121.4 (8)	C16—C15—C14	120.8 (12)
F1—C2—C1	118.3 (7)	C17—C16—C15	119.7 (11)
F1—C2—C3	116.7 (8)	C16—C17—C18	121.0 (13)
C1—C2—C3	125.0 (8)	C17—C18—C13	118.3 (13)
C2—C3—C4	114.9 (7)	C20—C19—C24	120.0
C2—C3—C9	122.7 (8)	C20—C19—P1	117.6 (9)
C4—C3—C9	122.3 (8)	C24—C19—P1	122.1 (8)
F2—C4—C5	119.0 (7)	C19—C20—C21	120.0
F2—C4—C3	117.1 (7)	C22—C21—C20	120.0
C5—C4—C3	123.9 (8)	C21—C22—C23	120.0
C4—C5—C6	116.2 (8)	C22—C23—C24	120.0
C4—C5—C11	121.4 (8)	C23—C24—C19	120.0
C6—C5—C11	122.4 (8)	C26—C25—P1	114 (3)
F3—C6—C1	118.1 (8)	O1—C26—C25	121 (3)
F3—C6—C5	117.8 (8)	O1—C26—C27	122 (3)
C1—C6—C5	124.1 (8)	C25—C26—C27	116 (3)
C8—C7—C1	176.7 (10)	N1—C28—C29	176.6 (18)
C7—C8—I1	176.8 (9)

C6—C1—C2—F1	−178.2 (8)	C19—P1—C13—C18	−153.4 (11)
C7—C1—C2—F1	−2.4 (13)	C13ⁱ—P1—C13—C18	75.3 (10)
C6—C1—C2—C3	3.8 (13)	C25—P1—C13—C18	−40.7 (15)
C7—C1—C2—C3	179.5 (9)	C18—C13—C14—C15	−0.1 (17)
F1—C2—C3—C4	177.7 (7)	P1—C13—C14—C15	174.2 (9)
C1—C2—C3—C4	−4.1 (13)	C13—C14—C15—C16	−1.8 (17)
F1—C2—C3—C9	0.3 (12)	C14—C15—C16—C17	2.9 (19)
C1—C2—C3—C9	178.4 (8)	C15—C16—C17—C18	−2 (2)
C2—C3—C4—F2	−176.9 (7)	C16—C17—C18—C13	0 (2)
C9—C3—C4—F2	0.6 (13)	C14—C13—C18—C17	1 (2)
C2—C3—C4—C5	1.9 (13)	P1—C13—C18—C17	−173.7 (11)
C9—C3—C4—C5	179.4 (8)	C13ⁱ—P1—C19—C20	154.7 (7)
F2—C4—C5—C6	179.2 (8)	C13—P1—C19—C20	27.0 (10)
C3—C4—C5—C6	0.4 (14)	C25—P1—C19—C20	−84.1 (13)
F2—C4—C5—C11	1.8 (13)	C13ⁱ—P1—C19—C24	−18.4 (11)
C3—C4—C5—C11	−176.9 (9)	C13—P1—C19—C24	−146.1 (8)
C2—C1—C6—F3	178.6 (8)	C25—P1—C19—C24	102.7 (13)
C7—C1—C6—F3	2.7 (13)	C24—C19—C20—C21	0.0
C2—C1—C6—C5	−1.1 (14)	P1—C19—C20—C21	−173.3 (11)
C7—C1—C6—C5	−176.9 (9)	C19—C20—C21—C22	0.0
C4—C5—C6—F3	179.5 (8)	C20—C21—C22—C23	0.0
C11—C5—C6—F3	−3.2 (14)	C21—C22—C23—C24	0.0
C4—C5—C6—C1	−0.9 (14)	C22—C23—C24—C19	0.0
C11—C5—C6—C1	176.4 (9)	C20—C19—C24—C23	0.0
C19—P1—C13—C14	32.0 (12)	P1—C19—C24—C23	173.0 (12)
C13ⁱ—P1—C13—C14	−99.3 (10)	P1—C25—C26—O1	−26 (5)
C25—P1—C13—C14	144.8 (13)	P1—C25—C26—C27	160 (3)

Symmetry code: (i) −x−1, y, −z+1/2.

(1f) top

Crystal data top

C₂₄H₂₀P·2(C₁₂F₃I₃)·2(C₂H₃N)·Br	F(000) = 3096
M_r = 1665.03	D_x = 2.084 Mg m⁻³ D_m = n/a Mg m⁻³ D_m measured by ?
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.5544 (3) Å	Cell parameters from 9989 reflections
b = 16.4031 (4) Å	θ = 2.3–28.3°
c = 30.8221 (8) Å	µ = 4.35 mm⁻¹
β = 96.1095 (12)°	T = 200 K
V = 5305.8 (2) Å³	Block, colourless
Z = 4	0.26 × 0.24 × 0.22 mm

Data collection top

Bruker APEX-II CCD diffractometer	5916 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.022
Absorption correction: multi-scan SADABS, Bruker (2003)	θ_max = 28.3°, θ_min = 2.3°
T_min = 0.633, T_max = 0.746	h = −13→14
24116 measured reflections	k = −21→21
6501 independent reflections	l = −40→41

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.025	H-atom parameters constrained
wR(F²) = 0.065	w = 1/[σ²(F_o²) + (0.0351P)² + 11.4136P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.002
6501 reflections	Δρ_max = 0.90 e Å⁻³
309 parameters	Δρ_min = −1.03 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
I1	0.44671 (2)	0.14616 (2)	0.65143 (2)	0.03741 (6)
I2	0.26141 (2)	0.65835 (2)	0.44640 (2)	0.03483 (6)
I3	0.46543 (2)	0.08589 (2)	0.31933 (2)	0.03593 (6)
Br1	0.5000	0.06053 (2)	0.7500	0.03846 (10)
P1	0.5000	0.38958 (6)	0.2500	0.02527 (18)
F1	0.36519 (18)	0.39499 (11)	0.54407 (6)	0.0403 (4)
F2	0.3866 (2)	0.37352 (11)	0.39377 (6)	0.0464 (5)
F3	0.44052 (18)	0.14197 (10)	0.48199 (6)	0.0398 (4)
N1	0.2173 (4)	−0.1637 (2)	0.42132 (14)	0.0689 (10)
C1	0.4075 (3)	0.26766 (16)	0.51525 (9)	0.0286 (5)
C2	0.3832 (3)	0.35032 (16)	0.50901 (9)	0.0296 (5)
C3	0.3746 (3)	0.38862 (17)	0.46848 (9)	0.0308 (6)
C4	0.3928 (3)	0.33935 (17)	0.43306 (9)	0.0318 (6)
C5	0.4149 (3)	0.25602 (17)	0.43598 (9)	0.0300 (5)
C6	0.4213 (3)	0.22302 (16)	0.47772 (9)	0.0296 (5)
C7	0.4166 (3)	0.23075 (17)	0.55740 (9)	0.0311 (6)
C8	0.4255 (3)	0.19913 (17)	0.59225 (10)	0.0340 (6)
C9	0.3427 (3)	0.47332 (18)	0.46346 (10)	0.0337 (6)
C10	0.3114 (3)	0.54210 (18)	0.45826 (10)	0.0352 (6)
C11	0.4278 (3)	0.20688 (18)	0.39826 (10)	0.0348 (6)
C12	0.4396 (3)	0.16491 (18)	0.36774 (10)	0.0369 (6)
C13	0.3642 (3)	0.32396 (16)	0.24000 (9)	0.0275 (5)
C14	0.3273 (3)	0.29776 (19)	0.19767 (10)	0.0363 (6)
H14A	0.3658	0.3199	0.1738	0.044*
C15	0.2331 (3)	0.2388 (2)	0.19095 (11)	0.0446 (8)
H15A	0.2058	0.2209	0.1621	0.054*
C16	0.1790 (3)	0.20579 (19)	0.22559 (12)	0.0429 (7)
H16A	0.1146	0.1654	0.2205	0.052*
C17	0.2173 (3)	0.23090 (18)	0.26755 (11)	0.0403 (7)
H17A	0.1793	0.2079	0.2913	0.048*
C18	0.3112 (3)	0.28945 (17)	0.27514 (10)	0.0327 (6)
H18A	0.3392	0.3060	0.3041	0.039*
C19	0.4891 (3)	0.45535 (16)	0.29574 (8)	0.0270 (5)
C20	0.3717 (3)	0.47779 (17)	0.30850 (9)	0.0312 (6)
H20A	0.2955	0.4540	0.2949	0.037*
C21	0.3671 (3)	0.53551 (18)	0.34143 (10)	0.0351 (6)
H21A	0.2873	0.5502	0.3508	0.042*
C22	0.4780 (3)	0.57163 (19)	0.36060 (10)	0.0383 (7)
H22A	0.4741	0.6109	0.3831	0.046*
C23	0.5942 (3)	0.5504 (2)	0.34698 (10)	0.0403 (7)
H23A	0.6699	0.5759	0.3598	0.048*
C24	0.6008 (3)	0.49212 (19)	0.31472 (10)	0.0374 (6)
H24A	0.6809	0.4773	0.3056	0.045*
C25	0.2778 (4)	−0.1076 (2)	0.42848 (12)	0.0481 (8)
C26	0.3575 (4)	−0.0365 (2)	0.43878 (15)	0.0590 (10)
H26A	0.3365	−0.0124	0.4662	0.089*
H26B	0.3424	0.0037	0.4153	0.089*
H26C	0.4473	−0.0527	0.4418	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.04376 (12)	0.03922 (11)	0.03088 (10)	0.00009 (8)	0.01154 (8)	0.00507 (7)
I2	0.03525 (11)	0.02862 (9)	0.04119 (11)	0.00603 (7)	0.00679 (8)	0.00145 (7)
I3	0.04147 (11)	0.03232 (10)	0.03413 (10)	0.00437 (7)	0.00467 (8)	−0.00500 (7)
Br1	0.0645 (3)	0.02975 (19)	0.02117 (17)	0.000	0.00470 (18)	0.000
P1	0.0273 (5)	0.0280 (4)	0.0210 (4)	0.000	0.0045 (4)	0.000
F1	0.0500 (11)	0.0399 (9)	0.0311 (9)	0.0059 (8)	0.0047 (8)	−0.0065 (7)
F2	0.0693 (13)	0.0402 (10)	0.0287 (9)	0.0109 (9)	−0.0003 (9)	0.0063 (7)
F3	0.0481 (11)	0.0261 (8)	0.0460 (10)	0.0035 (7)	0.0083 (8)	0.0026 (7)
N1	0.076 (3)	0.052 (2)	0.081 (3)	0.0008 (18)	0.014 (2)	0.0015 (18)
C1	0.0236 (12)	0.0308 (13)	0.0315 (13)	−0.0012 (10)	0.0040 (11)	0.0024 (10)
C2	0.0248 (13)	0.0310 (13)	0.0326 (14)	−0.0001 (10)	0.0007 (11)	−0.0041 (10)
C3	0.0302 (14)	0.0283 (13)	0.0333 (14)	0.0016 (10)	0.0004 (11)	−0.0004 (10)
C4	0.0341 (15)	0.0325 (14)	0.0278 (13)	0.0042 (11)	−0.0018 (11)	0.0017 (10)
C5	0.0280 (13)	0.0318 (13)	0.0294 (13)	0.0038 (10)	−0.0010 (11)	−0.0029 (10)
C6	0.0264 (13)	0.0274 (12)	0.0349 (14)	0.0017 (10)	0.0032 (11)	0.0009 (10)
C7	0.0277 (13)	0.0341 (13)	0.0322 (14)	0.0007 (11)	0.0062 (11)	0.0005 (11)
C8	0.0360 (15)	0.0328 (14)	0.0350 (15)	0.0016 (11)	0.0114 (12)	0.0010 (11)
C9	0.0336 (15)	0.0343 (14)	0.0331 (14)	0.0006 (11)	0.0029 (12)	−0.0028 (11)
C10	0.0376 (16)	0.0319 (14)	0.0364 (15)	0.0026 (12)	0.0053 (13)	0.0002 (11)
C11	0.0339 (15)	0.0359 (14)	0.0342 (15)	0.0043 (12)	0.0021 (12)	−0.0004 (11)
C12	0.0409 (17)	0.0341 (14)	0.0348 (15)	0.0044 (12)	0.0006 (13)	−0.0021 (12)
C13	0.0282 (13)	0.0265 (12)	0.0279 (13)	0.0016 (10)	0.0030 (11)	−0.0011 (10)
C14	0.0363 (16)	0.0417 (16)	0.0310 (14)	−0.0009 (12)	0.0033 (12)	−0.0074 (12)
C15	0.0448 (18)	0.0452 (17)	0.0422 (17)	−0.0013 (14)	−0.0033 (15)	−0.0156 (14)
C16	0.0355 (16)	0.0339 (15)	0.060 (2)	−0.0041 (12)	0.0066 (15)	−0.0128 (14)
C17	0.0413 (17)	0.0303 (14)	0.0519 (19)	−0.0032 (12)	0.0166 (14)	−0.0009 (12)
C18	0.0355 (15)	0.0303 (13)	0.0327 (14)	0.0003 (11)	0.0053 (12)	−0.0012 (11)
C19	0.0321 (14)	0.0282 (12)	0.0212 (11)	−0.0006 (10)	0.0059 (10)	0.0011 (9)
C20	0.0361 (15)	0.0298 (13)	0.0283 (13)	0.0013 (11)	0.0058 (12)	0.0036 (10)
C21	0.0404 (16)	0.0332 (14)	0.0330 (14)	0.0068 (12)	0.0103 (13)	−0.0007 (11)
C22	0.0524 (19)	0.0363 (15)	0.0260 (13)	0.0038 (13)	0.0034 (13)	−0.0039 (11)
C23	0.0390 (16)	0.0451 (17)	0.0356 (16)	−0.0038 (13)	−0.0019 (13)	−0.0100 (13)
C24	0.0326 (15)	0.0447 (16)	0.0353 (15)	−0.0024 (12)	0.0051 (12)	−0.0064 (12)
C25	0.062 (2)	0.0394 (17)	0.0447 (18)	0.0144 (16)	0.0154 (17)	0.0048 (14)
C26	0.070 (3)	0.0391 (18)	0.071 (3)	0.0068 (18)	0.021 (2)	−0.0022 (17)

Geometric parameters (Å, º) top

I1—C8	2.011 (3)	C5—C6	1.391 (4)
I2—C10	2.002 (3)	C5—C11	1.433 (4)
I3—C12	2.017 (3)	C7—C8	1.188 (4)
P1—C19ⁱ	1.789 (3)	C9—C10	1.182 (4)
P1—C19	1.789 (3)	C11—C12	1.183 (4)
P1—C13ⁱ	1.793 (3)	C13—C14	1.389 (4)
P1—C13	1.793 (3)	C13—C18	1.391 (4)
F1—C2	1.336 (3)	C14—C15	1.387 (5)
F2—C4	1.330 (3)	C15—C16	1.374 (5)
F3—C6	1.349 (3)	C16—C17	1.376 (5)
N1—C25	1.128 (5)	C17—C18	1.381 (4)
C1—C2	1.390 (4)	C19—C20	1.389 (4)
C1—C6	1.390 (4)	C19—C24	1.396 (4)
C1—C7	1.427 (4)	C20—C21	1.393 (4)
C2—C3	1.393 (4)	C21—C22	1.387 (5)
C3—C4	1.388 (4)	C22—C23	1.383 (5)
C3—C9	1.434 (4)	C23—C24	1.386 (4)
C4—C5	1.388 (4)	C25—C26	1.454 (6)

C19ⁱ—P1—C19	105.80 (17)	C8—C7—C1	178.9 (3)
C19ⁱ—P1—C13ⁱ	112.36 (12)	C7—C8—I1	178.2 (3)
C19—P1—C13ⁱ	110.12 (12)	C10—C9—C3	177.0 (3)
C19ⁱ—P1—C13	110.11 (12)	C9—C10—I2	177.1 (3)
C19—P1—C13	112.36 (12)	C12—C11—C5	178.5 (3)
C13ⁱ—P1—C13	106.21 (18)	C11—C12—I3	175.1 (3)
C2—C1—C6	115.7 (3)	C14—C13—C18	120.6 (3)
C2—C1—C7	122.2 (3)	C14—C13—P1	119.1 (2)
C6—C1—C7	122.1 (3)	C18—C13—P1	119.4 (2)
F1—C2—C1	117.6 (3)	C15—C14—C13	118.7 (3)
F1—C2—C3	118.5 (2)	C16—C15—C14	120.6 (3)
C1—C2—C3	123.9 (3)	C15—C16—C17	120.5 (3)
C4—C3—C2	116.2 (3)	C16—C17—C18	120.1 (3)
C4—C3—C9	122.0 (3)	C17—C18—C13	119.4 (3)
C2—C3—C9	121.7 (3)	C20—C19—C24	120.4 (3)
F2—C4—C5	117.8 (3)	C20—C19—P1	121.1 (2)
F2—C4—C3	118.3 (2)	C24—C19—P1	117.9 (2)
C5—C4—C3	124.0 (3)	C19—C20—C21	119.2 (3)
C4—C5—C6	115.8 (3)	C22—C21—C20	120.5 (3)
C4—C5—C11	122.1 (3)	C23—C22—C21	119.9 (3)
C6—C5—C11	122.1 (3)	C22—C23—C24	120.4 (3)
F3—C6—C1	117.8 (2)	C23—C24—C19	119.6 (3)
F3—C6—C5	117.8 (2)	N1—C25—C26	178.4 (5)
C1—C6—C5	124.5 (3)

C6—C1—C2—F1	177.9 (2)	C13ⁱ—P1—C13—C14	−88.6 (2)
C7—C1—C2—F1	−1.6 (4)	C19ⁱ—P1—C13—C18	−157.4 (2)
C6—C1—C2—C3	−1.0 (4)	C19—P1—C13—C18	−39.7 (3)
C7—C1—C2—C3	179.5 (3)	C13ⁱ—P1—C13—C18	80.7 (2)
F1—C2—C3—C4	−179.3 (3)	C18—C13—C14—C15	2.4 (4)
C1—C2—C3—C4	−0.4 (4)	P1—C13—C14—C15	171.6 (2)
F1—C2—C3—C9	−2.3 (4)	C13—C14—C15—C16	−1.1 (5)
C1—C2—C3—C9	176.6 (3)	C14—C15—C16—C17	0.0 (5)
C2—C3—C4—F2	−179.4 (3)	C15—C16—C17—C18	−0.2 (5)
C9—C3—C4—F2	3.6 (4)	C16—C17—C18—C13	1.4 (5)
C2—C3—C4—C5	1.7 (5)	C14—C13—C18—C17	−2.6 (4)
C9—C3—C4—C5	−175.3 (3)	P1—C13—C18—C17	−171.7 (2)
F2—C4—C5—C6	179.6 (3)	C19ⁱ—P1—C19—C20	93.9 (2)
C3—C4—C5—C6	−1.5 (4)	C13ⁱ—P1—C19—C20	−144.4 (2)
F2—C4—C5—C11	−1.6 (4)	C13—P1—C19—C20	−26.2 (3)
C3—C4—C5—C11	177.3 (3)	C19ⁱ—P1—C19—C24	−77.8 (2)
C2—C1—C6—F3	−177.7 (2)	C13ⁱ—P1—C19—C24	43.9 (3)
C7—C1—C6—F3	1.8 (4)	C13—P1—C19—C24	162.0 (2)
C2—C1—C6—C5	1.3 (4)	C24—C19—C20—C21	−2.0 (4)
C7—C1—C6—C5	−179.2 (3)	P1—C19—C20—C21	−173.5 (2)
C4—C5—C6—F3	178.9 (3)	C19—C20—C21—C22	1.5 (4)
C11—C5—C6—F3	0.1 (4)	C20—C21—C22—C23	0.1 (5)
C4—C5—C6—C1	−0.1 (4)	C21—C22—C23—C24	−1.1 (5)
C11—C5—C6—C1	−178.9 (3)	C22—C23—C24—C19	0.5 (5)
C19ⁱ—P1—C13—C14	33.3 (3)	C20—C19—C24—C23	1.0 (4)
C19—P1—C13—C14	151.0 (2)	P1—C19—C24—C23	172.8 (2)

Symmetry code: (i) −x+1, y, −z+1/2.

(1g) top

Crystal data top

C₃₁H₂₄F₂P·C₁₂F₃I₃·C₂H₃N·Br	D_x = 1.676 Mg m⁻³
M_r = 1168.25	Melting point: 441 K
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.7807 (5) Å	Cell parameters from 9606 reflections
b = 28.8937 (12) Å	θ = 2.3–28.4°
c = 14.8900 (6) Å	µ = 2.97 mm⁻¹
β = 93.368 (2)°	T = 200 K
V = 4630.1 (3) Å³	Block, colourless
Z = 4	0.18 × 0.16 × 0.15 mm
F(000) = 2232

Data collection top

Bruker APEX-II CCD diffractometer	9926 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.029
Absorption correction: multi-scan SADABS, Bruker (2003)	θ_max = 28.4°, θ_min = 1.5°
T_min = 0.624, T_max = 0.746	h = −14→14
55736 measured reflections	k = −38→37
11400 independent reflections	l = −19→19

Refinement top

Refinement on F²	24 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.0263P)² + 16.7765P] where P = (F_o² + 2F_c²)/3
S = 1.19	(Δ/σ)_max = 0.001
11400 reflections	Δρ_max = 1.23 e Å⁻³
534 parameters	Δρ_min = −0.88 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
I1	0.82257 (3)	0.22612 (2)	0.50544 (2)	0.03482 (8)
I2	0.80283 (3)	−0.09041 (2)	0.87533 (2)	0.03758 (8)
I3	0.82872 (4)	−0.10299 (2)	0.20201 (2)	0.04289 (9)
Br1	0.70518 (5)	0.32967 (2)	0.46737 (3)	0.04099 (12)
P1	0.67009 (9)	0.67423 (4)	0.38892 (6)	0.0226 (2)
F1	0.8421 (3)	0.06933 (10)	0.68509 (19)	0.0497 (8)
F2	0.8423 (3)	−0.07460 (9)	0.54306 (19)	0.0470 (7)
F3	0.8623 (3)	0.06050 (10)	0.37286 (19)	0.0527 (8)
F4	0.6064 (4)	0.90019 (11)	0.4625 (3)	0.0740 (11)
F5	0.9801 (5)	0.65568 (18)	0.7853 (3)	0.1021 (16)
C1	0.8514 (5)	0.06718 (15)	0.5285 (3)	0.0355 (10)
C2	0.8448 (5)	0.04391 (16)	0.6098 (3)	0.0367 (10)
C3	0.8401 (5)	−0.00377 (15)	0.6176 (3)	0.0344 (10)
C4	0.8429 (4)	−0.02835 (15)	0.5379 (3)	0.0337 (10)
C5	0.8477 (4)	−0.00843 (15)	0.4540 (3)	0.0324 (9)
C6	0.8533 (5)	0.03962 (16)	0.4523 (3)	0.0346 (10)
C7	0.8545 (5)	0.11687 (17)	0.5240 (3)	0.0387 (11)
C8	0.8515 (5)	0.15762 (15)	0.5194 (3)	0.0368 (10)
C9	0.8315 (5)	−0.02704 (17)	0.7026 (3)	0.0409 (11)
C10	0.8215 (5)	−0.04865 (16)	0.7687 (3)	0.0406 (11)
C11	0.8466 (5)	−0.03586 (16)	0.3740 (3)	0.0386 (11)
C12	0.8442 (5)	−0.06032 (17)	0.3099 (3)	0.0446 (12)
C13	0.8040 (4)	0.69145 (15)	0.3309 (3)	0.0248 (8)
C14	0.7898 (4)	0.72764 (15)	0.2691 (3)	0.0293 (9)
H14A	0.7106	0.7413	0.2563	0.035*
C15	0.8926 (5)	0.74342 (18)	0.2267 (3)	0.0389 (11)
H15A	0.8841	0.7682	0.1848	0.047*
C16	1.0065 (4)	0.7235 (2)	0.2450 (3)	0.0433 (12)
H16A	1.0766	0.7345	0.2155	0.052*
C17	1.0207 (5)	0.6875 (2)	0.3058 (4)	0.0448 (12)
H17A	1.0999	0.6737	0.3176	0.054*
C18	0.9193 (4)	0.67157 (17)	0.3493 (3)	0.0348 (10)
H18A	0.9288	0.6471	0.3916	0.042*
C19	0.5377 (4)	0.68419 (14)	0.3116 (2)	0.0241 (8)
C20	0.5372 (4)	0.66186 (17)	0.2283 (3)	0.0342 (10)
H20A	0.6059	0.6432	0.2138	0.041*
C21	0.4371 (5)	0.66693 (17)	0.1674 (3)	0.0376 (11)
H21A	0.4366	0.6517	0.1109	0.045*
C22	0.3378 (4)	0.69398 (16)	0.1882 (3)	0.0330 (10)
H22A	0.2684	0.6972	0.1463	0.040*
C23	0.3391 (4)	0.71657 (16)	0.2704 (3)	0.0348 (10)
H23A	0.2710	0.7356	0.2843	0.042*
C24	0.4389 (4)	0.71156 (15)	0.3325 (3)	0.0282 (8)
H24A	0.4393	0.7269	0.3890	0.034*
C25	0.6780 (4)	0.61332 (14)	0.4138 (3)	0.0289 (9)
C26	0.6252 (5)	0.59538 (16)	0.4892 (3)	0.0371 (10)
H26A	0.5887	0.6154	0.5308	0.045*
C27	0.6262 (6)	0.54792 (18)	0.5034 (4)	0.0516 (14)
H27A	0.5923	0.5356	0.5557	0.062*
C28	0.6757 (6)	0.51870 (19)	0.4423 (4)	0.0589 (16)
H28A	0.6757	0.4862	0.4524	0.071*
C29	0.7255 (6)	0.53637 (19)	0.3661 (4)	0.0581 (15)
H29A	0.7582	0.5159	0.3235	0.070*
C30	0.7279 (5)	0.58362 (17)	0.3516 (3)	0.0426 (11)
H30A	0.7634	0.5957	0.2996	0.051*
C31	0.6523 (4)	0.70668 (14)	0.4944 (2)	0.0242 (8)
H31A	0.5690	0.6973	0.5144	0.029*
C32	0.6442 (4)	0.75916 (15)	0.4826 (2)	0.0277 (9)
C33	0.5389 (4)	0.78115 (16)	0.5107 (3)	0.0330 (9)
H33A	0.4747	0.7632	0.5346	0.040*
C34	0.5253 (5)	0.82874 (18)	0.5048 (4)	0.0458 (12)
H34A	0.4525	0.8436	0.5233	0.055*
C35	0.6205 (5)	0.85376 (17)	0.4711 (4)	0.0447 (12)
C36	0.7265 (5)	0.83388 (17)	0.4446 (3)	0.0427 (12)
H36A	0.7906	0.8523	0.4219	0.051*
C37	0.7398 (5)	0.78610 (16)	0.4513 (3)	0.0332 (10)
H37A	0.8143	0.7718	0.4344	0.040*
C38	0.7442 (4)	0.69207 (15)	0.5712 (3)	0.0299 (9)
C39	0.8713 (5)	0.69685 (19)	0.5671 (3)	0.0407 (11)
H39A	0.9043	0.7089	0.5141	0.049*
C40	0.9509 (6)	0.6843 (2)	0.6391 (4)	0.0558 (15)
H40A	1.0382	0.6872	0.6354	0.067*
C41	0.9033 (6)	0.6679 (2)	0.7151 (4)	0.0581 (16)
C42	0.7789 (7)	0.6632 (2)	0.7231 (3)	0.0574 (16)
H42A	0.7479	0.6518	0.7773	0.069*
C43	0.6970 (5)	0.67541 (16)	0.6502 (3)	0.0380 (11)
H43A	0.6099	0.6723	0.6546	0.046*
N1	0.592 (2)	0.0895 (7)	0.3388 (12)	0.130 (7)	0.5
C44	0.5510 (17)	0.0546 (8)	0.3520 (12)	0.110 (7)	0.5
C45	0.5047 (15)	0.0096 (8)	0.3692 (15)	0.128 (8)	0.5
H45A	0.5416	−0.0017	0.4268	0.191*	0.5
H45B	0.5265	−0.0114	0.3209	0.191*	0.5
H45C	0.4141	0.0109	0.3717	0.191*	0.5
N2	0.955 (2)	0.5190 (10)	0.6502 (17)	0.191 (12)	0.5
C47	0.9943 (11)	0.5733 (5)	0.5266 (11)	0.073 (4)	0.5
H47A	0.9269	0.5961	0.5205	0.109*	0.5
H47B	0.9983	0.5560	0.4702	0.109*	0.5
H47C	1.0734	0.5893	0.5400	0.109*	0.5
C46	0.9721 (14)	0.5430 (6)	0.5958 (12)	0.089 (5)	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.04236 (17)	0.02203 (14)	0.04037 (16)	0.00127 (12)	0.00505 (12)	0.00036 (11)
I2	0.05178 (19)	0.03055 (15)	0.03065 (14)	0.00039 (13)	0.00456 (13)	0.00179 (11)
I3	0.0617 (2)	0.03278 (16)	0.03389 (15)	−0.00211 (14)	0.00062 (14)	−0.00589 (12)
Br1	0.0706 (4)	0.0250 (2)	0.0280 (2)	0.0050 (2)	0.0079 (2)	0.00150 (16)
P1	0.0214 (5)	0.0260 (5)	0.0200 (4)	−0.0006 (4)	−0.0010 (4)	0.0013 (4)
F1	0.081 (2)	0.0323 (15)	0.0364 (14)	0.0046 (15)	0.0116 (15)	−0.0062 (11)
F2	0.074 (2)	0.0201 (13)	0.0459 (16)	−0.0037 (13)	−0.0047 (15)	0.0010 (11)
F3	0.090 (2)	0.0355 (16)	0.0327 (14)	0.0032 (16)	0.0078 (15)	0.0086 (12)
F4	0.090 (3)	0.0286 (17)	0.101 (3)	0.0006 (17)	−0.016 (2)	0.0051 (17)
F5	0.115 (4)	0.133 (4)	0.053 (2)	0.026 (3)	−0.047 (2)	0.018 (2)
C1	0.047 (3)	0.023 (2)	0.037 (2)	0.0034 (19)	0.002 (2)	0.0004 (17)
C2	0.047 (3)	0.030 (2)	0.033 (2)	0.001 (2)	0.005 (2)	−0.0050 (18)
C3	0.039 (3)	0.028 (2)	0.036 (2)	0.0025 (19)	0.0032 (19)	0.0048 (17)
C4	0.038 (3)	0.023 (2)	0.039 (2)	−0.0023 (18)	−0.0004 (19)	0.0030 (17)
C5	0.037 (2)	0.029 (2)	0.031 (2)	0.0014 (18)	−0.0024 (18)	−0.0015 (17)
C6	0.043 (3)	0.029 (2)	0.031 (2)	0.0038 (19)	0.0028 (19)	0.0033 (17)
C7	0.046 (3)	0.033 (3)	0.038 (2)	0.005 (2)	0.006 (2)	0.0014 (19)
C8	0.049 (3)	0.021 (2)	0.041 (2)	0.0045 (19)	0.009 (2)	0.0003 (17)
C9	0.049 (3)	0.035 (3)	0.039 (2)	0.001 (2)	0.003 (2)	0.001 (2)
C10	0.059 (3)	0.030 (2)	0.033 (2)	0.002 (2)	0.007 (2)	0.0024 (18)
C11	0.047 (3)	0.030 (2)	0.038 (2)	0.000 (2)	−0.003 (2)	−0.0005 (19)
C12	0.062 (3)	0.033 (3)	0.038 (2)	−0.002 (2)	−0.002 (2)	−0.005 (2)
C13	0.0191 (19)	0.034 (2)	0.0216 (17)	−0.0016 (16)	0.0008 (14)	−0.0003 (15)
C14	0.024 (2)	0.036 (2)	0.0278 (19)	0.0004 (17)	0.0004 (16)	0.0038 (17)
C15	0.041 (3)	0.046 (3)	0.030 (2)	−0.006 (2)	0.0031 (19)	0.0104 (19)
C16	0.025 (2)	0.068 (4)	0.037 (2)	−0.008 (2)	0.0027 (19)	0.008 (2)
C17	0.024 (2)	0.061 (3)	0.049 (3)	0.007 (2)	0.002 (2)	0.011 (2)
C18	0.028 (2)	0.040 (3)	0.036 (2)	0.0028 (19)	0.0006 (18)	0.0084 (19)
C19	0.0224 (19)	0.027 (2)	0.0220 (17)	−0.0045 (15)	−0.0016 (15)	0.0020 (15)
C20	0.031 (2)	0.042 (3)	0.029 (2)	0.0040 (19)	−0.0003 (17)	−0.0075 (18)
C21	0.040 (3)	0.050 (3)	0.0216 (19)	−0.007 (2)	−0.0054 (18)	−0.0066 (18)
C22	0.028 (2)	0.044 (3)	0.0263 (19)	−0.0026 (19)	−0.0071 (17)	0.0052 (18)
C23	0.029 (2)	0.039 (3)	0.036 (2)	0.0037 (19)	−0.0003 (18)	0.0007 (19)
C24	0.028 (2)	0.032 (2)	0.0244 (18)	−0.0025 (17)	−0.0023 (16)	−0.0034 (16)
C25	0.030 (2)	0.025 (2)	0.030 (2)	0.0005 (17)	−0.0045 (17)	0.0018 (16)
C26	0.041 (3)	0.033 (2)	0.037 (2)	−0.006 (2)	−0.001 (2)	0.0034 (19)
C27	0.070 (4)	0.037 (3)	0.047 (3)	−0.011 (3)	−0.004 (3)	0.014 (2)
C28	0.083 (5)	0.027 (3)	0.065 (4)	−0.001 (3)	−0.008 (3)	0.007 (2)
C29	0.077 (4)	0.035 (3)	0.062 (4)	0.014 (3)	0.005 (3)	−0.006 (3)
C30	0.053 (3)	0.034 (3)	0.040 (3)	0.004 (2)	0.006 (2)	0.001 (2)
C31	0.024 (2)	0.030 (2)	0.0184 (16)	−0.0045 (16)	0.0006 (15)	0.0008 (14)
C32	0.034 (2)	0.031 (2)	0.0174 (16)	−0.0042 (17)	−0.0048 (16)	−0.0022 (15)
C33	0.030 (2)	0.035 (2)	0.033 (2)	−0.0017 (18)	−0.0027 (18)	−0.0037 (18)
C34	0.045 (3)	0.035 (3)	0.057 (3)	0.006 (2)	−0.007 (2)	−0.009 (2)
C35	0.059 (3)	0.028 (2)	0.045 (3)	−0.002 (2)	−0.015 (2)	−0.001 (2)
C36	0.061 (3)	0.034 (3)	0.032 (2)	−0.018 (2)	−0.003 (2)	0.0016 (19)
C37	0.040 (3)	0.035 (2)	0.0243 (19)	−0.0103 (19)	0.0014 (18)	−0.0029 (17)
C38	0.036 (2)	0.032 (2)	0.0212 (18)	−0.0010 (18)	−0.0029 (16)	−0.0013 (16)
C39	0.036 (3)	0.059 (3)	0.026 (2)	0.007 (2)	−0.0081 (19)	−0.001 (2)
C40	0.043 (3)	0.080 (4)	0.043 (3)	0.011 (3)	−0.012 (2)	−0.006 (3)
C41	0.069 (4)	0.066 (4)	0.037 (3)	0.012 (3)	−0.023 (3)	0.002 (3)
C42	0.095 (5)	0.048 (3)	0.028 (2)	−0.002 (3)	−0.003 (3)	0.010 (2)
C43	0.052 (3)	0.035 (2)	0.027 (2)	−0.008 (2)	0.002 (2)	0.0039 (17)
N1	0.144 (14)	0.180 (17)	0.069 (10)	0.070 (12)	0.038 (10)	0.010 (11)
C44	0.093 (12)	0.176 (17)	0.063 (10)	0.079 (12)	0.017 (8)	0.014 (11)
C45	0.061 (10)	0.187 (17)	0.134 (17)	0.076 (11)	−0.004 (9)	0.038 (12)
N2	0.110 (16)	0.24 (2)	0.215 (19)	−0.058 (16)	−0.026 (14)	0.105 (19)
C47	0.034 (6)	0.063 (8)	0.120 (11)	0.006 (5)	−0.013 (7)	−0.013 (7)
C46	0.047 (8)	0.089 (10)	0.131 (12)	−0.010 (7)	−0.008 (8)	−0.011 (8)

Geometric parameters (Å, º) top

I1—C8	2.012 (4)	C24—H24A	0.9500
I2—C10	2.013 (5)	C25—C26	1.389 (6)
I3—C12	2.024 (5)	C25—C30	1.394 (7)
P1—C13	1.796 (4)	C26—C27	1.387 (7)
P1—C25	1.800 (4)	C26—H26A	0.9500
P1—C19	1.804 (4)	C27—C28	1.372 (9)
P1—C31	1.848 (4)	C27—H27A	0.9500
F1—C2	1.342 (5)	C28—C29	1.381 (9)
F2—C4	1.339 (5)	C28—H28A	0.9500
F3—C6	1.336 (5)	C29—C30	1.383 (7)
F4—C35	1.355 (6)	C29—H29A	0.9500
F5—C41	1.343 (6)	C30—H30A	0.9500
C1—C6	1.388 (6)	C31—C32	1.528 (6)
C1—C2	1.390 (6)	C31—C38	1.528 (5)
C1—C7	1.438 (6)	C31—H31A	1.0000
C2—C3	1.384 (6)	C32—C33	1.388 (6)
C3—C4	1.385 (6)	C32—C37	1.393 (6)
C3—C9	1.441 (6)	C33—C34	1.385 (7)
C4—C5	1.379 (6)	C33—H33A	0.9500
C5—C6	1.390 (6)	C34—C35	1.374 (8)
C5—C11	1.429 (6)	C34—H34A	0.9500
C7—C8	1.180 (6)	C35—C36	1.358 (8)
C9—C10	1.176 (7)	C36—C37	1.391 (7)
C11—C12	1.187 (7)	C36—H36A	0.9500
C13—C18	1.382 (6)	C37—H37A	0.9500
C13—C14	1.395 (6)	C38—C39	1.383 (7)
C14—C15	1.384 (6)	C38—C43	1.393 (6)
C14—H14A	0.9500	C39—C40	1.382 (7)
C15—C16	1.369 (7)	C39—H39A	0.9500
C15—H15A	0.9500	C40—C41	1.355 (9)
C16—C17	1.382 (7)	C40—H40A	0.9500
C16—H16A	0.9500	C41—C42	1.360 (9)
C17—C18	1.381 (7)	C42—C43	1.404 (7)
C17—H17A	0.9500	C42—H42A	0.9500
C18—H18A	0.9500	C43—H43A	0.9500
C19—C24	1.376 (6)	N1—C44	1.120 (16)
C19—C20	1.398 (6)	C44—C45	1.422 (16)
C20—C21	1.376 (6)	C45—H45A	0.9800
C20—H20A	0.9500	C45—H45B	0.9800
C21—C22	1.375 (7)	C45—H45C	0.9800
C21—H21A	0.9500	N2—C46	1.090 (15)
C22—C23	1.387 (6)	C47—C46	1.383 (15)
C22—H22A	0.9500	C47—H47A	0.9800
C23—C24	1.385 (6)	C47—H47B	0.9800
C23—H23A	0.9500	C47—H47C	0.9800

C13—P1—C25	109.9 (2)	C27—C26—H26A	120.3
C13—P1—C19	106.11 (18)	C25—C26—H26A	120.3
C25—P1—C19	108.29 (19)	C28—C27—C26	120.5 (5)
C13—P1—C31	113.23 (18)	C28—C27—H27A	119.8
C25—P1—C31	109.11 (19)	C26—C27—H27A	119.8
C19—P1—C31	110.09 (19)	C27—C28—C29	120.1 (5)
C6—C1—C2	116.0 (4)	C27—C28—H28A	119.9
C6—C1—C7	122.2 (4)	C29—C28—H28A	119.9
C2—C1—C7	121.8 (4)	C28—C29—C30	120.4 (5)
F1—C2—C3	118.2 (4)	C28—C29—H29A	119.8
F1—C2—C1	117.9 (4)	C30—C29—H29A	119.8
C3—C2—C1	123.9 (4)	C29—C30—C25	119.5 (5)
C2—C3—C4	115.9 (4)	C29—C30—H30A	120.3
C2—C3—C9	122.9 (4)	C25—C30—H30A	120.3
C4—C3—C9	121.3 (4)	C32—C31—C38	113.0 (3)
F2—C4—C5	118.0 (4)	C32—C31—P1	114.4 (3)
F2—C4—C3	117.5 (4)	C38—C31—P1	113.6 (3)
C5—C4—C3	124.5 (4)	C32—C31—H31A	104.8
C4—C5—C6	115.9 (4)	C38—C31—H31A	104.8
C4—C5—C11	121.6 (4)	P1—C31—H31A	104.8
C6—C5—C11	122.5 (4)	C33—C32—C37	118.7 (4)
F3—C6—C1	118.1 (4)	C33—C32—C31	117.5 (4)
F3—C6—C5	118.2 (4)	C37—C32—C31	123.7 (4)
C1—C6—C5	123.8 (4)	C34—C33—C32	121.4 (5)
C8—C7—C1	177.1 (6)	C34—C33—H33A	119.3
C7—C8—I1	172.3 (5)	C32—C33—H33A	119.3
C10—C9—C3	175.4 (5)	C35—C34—C33	117.8 (5)
C9—C10—I2	175.2 (4)	C35—C34—H34A	121.1
C12—C11—C5	177.0 (5)	C33—C34—H34A	121.1
C11—C12—I3	176.3 (5)	F4—C35—C36	118.9 (5)
C18—C13—C14	120.3 (4)	F4—C35—C34	118.2 (5)
C18—C13—P1	121.9 (3)	C36—C35—C34	122.9 (5)
C14—C13—P1	117.7 (3)	C35—C36—C37	118.9 (5)
C15—C14—C13	119.2 (4)	C35—C36—H36A	120.5
C15—C14—H14A	120.4	C37—C36—H36A	120.5
C13—C14—H14A	120.4	C36—C37—C32	120.2 (5)
C16—C15—C14	120.3 (4)	C36—C37—H37A	119.9
C16—C15—H15A	119.9	C32—C37—H37A	119.9
C14—C15—H15A	119.9	C39—C38—C43	118.9 (4)
C15—C16—C17	120.6 (5)	C39—C38—C31	122.6 (4)
C15—C16—H16A	119.7	C43—C38—C31	118.3 (4)
C17—C16—H16A	119.7	C40—C39—C38	120.7 (5)
C16—C17—C18	119.9 (5)	C40—C39—H39A	119.6
C16—C17—H17A	120.1	C38—C39—H39A	119.6
C18—C17—H17A	120.1	C41—C40—C39	119.4 (6)
C13—C18—C17	119.7 (4)	C41—C40—H40A	120.3
C13—C18—H18A	120.1	C39—C40—H40A	120.3
C17—C18—H18A	120.1	F5—C41—C40	119.8 (6)
C24—C19—C20	120.2 (4)	F5—C41—C42	118.1 (6)
C24—C19—P1	122.7 (3)	C40—C41—C42	122.2 (5)
C20—C19—P1	117.0 (3)	C41—C42—C43	119.0 (5)
C21—C20—C19	119.8 (4)	C41—C42—H42A	120.5
C21—C20—H20A	120.1	C43—C42—H42A	120.5
C19—C20—H20A	120.1	C38—C43—C42	119.7 (5)
C22—C21—C20	120.2 (4)	C38—C43—H43A	120.1
C22—C21—H21A	119.9	C42—C43—H43A	120.1
C20—C21—H21A	119.9	N1—C44—C45	178 (2)
C21—C22—C23	119.9 (4)	C44—C45—H45A	109.5
C21—C22—H22A	120.1	C44—C45—H45B	109.5
C23—C22—H22A	120.1	H45A—C45—H45B	109.5
C24—C23—C22	120.5 (4)	C44—C45—H45C	109.5
C24—C23—H23A	119.7	H45A—C45—H45C	109.5
C22—C23—H23A	119.7	H45B—C45—H45C	109.5
C19—C24—C23	119.4 (4)	C46—C47—H47A	109.5
C19—C24—H24A	120.3	C46—C47—H47B	109.5
C23—C24—H24A	120.3	H47A—C47—H47B	109.5
C26—C25—C30	120.0 (4)	C46—C47—H47C	109.5
C26—C25—P1	121.0 (3)	H47A—C47—H47C	109.5
C30—C25—P1	118.7 (3)	H47B—C47—H47C	109.5
C27—C26—C25	119.5 (5)	N2—C46—C47	180 (3)

C6—C1—C2—F1	−179.7 (4)	P1—C19—C24—C23	−178.3 (3)
C7—C1—C2—F1	−0.4 (8)	C22—C23—C24—C19	0.5 (7)
C6—C1—C2—C3	−0.1 (8)	C13—P1—C25—C26	149.8 (4)
C7—C1—C2—C3	179.2 (5)	C19—P1—C25—C26	−94.7 (4)
F1—C2—C3—C4	179.9 (4)	C31—P1—C25—C26	25.1 (4)
C1—C2—C3—C4	0.4 (8)	C13—P1—C25—C30	−36.2 (4)
F1—C2—C3—C9	0.5 (8)	C19—P1—C25—C30	79.3 (4)
C1—C2—C3—C9	−179.1 (5)	C31—P1—C25—C30	−160.9 (4)
C2—C3—C4—F2	178.0 (4)	C30—C25—C26—C27	2.0 (7)
C9—C3—C4—F2	−2.5 (7)	P1—C25—C26—C27	176.0 (4)
C2—C3—C4—C5	−1.2 (7)	C25—C26—C27—C28	−1.8 (8)
C9—C3—C4—C5	178.2 (5)	C26—C27—C28—C29	0.2 (10)
F2—C4—C5—C6	−177.5 (4)	C27—C28—C29—C30	1.2 (10)
C3—C4—C5—C6	1.8 (7)	C28—C29—C30—C25	−1.0 (9)
F2—C4—C5—C11	2.7 (7)	C26—C25—C30—C29	−0.7 (8)
C3—C4—C5—C11	−178.0 (5)	P1—C25—C30—C29	−174.7 (4)
C2—C1—C6—F3	−178.6 (4)	C13—P1—C31—C32	57.3 (3)
C7—C1—C6—F3	2.1 (7)	C25—P1—C31—C32	−179.9 (3)
C2—C1—C6—C5	0.7 (8)	C19—P1—C31—C32	−61.2 (3)
C7—C1—C6—C5	−178.6 (5)	C13—P1—C31—C38	−74.5 (3)
C4—C5—C6—F3	177.8 (4)	C25—P1—C31—C38	48.2 (3)
C11—C5—C6—F3	−2.4 (7)	C19—P1—C31—C38	166.9 (3)
C4—C5—C6—C1	−1.5 (7)	C38—C31—C32—C33	−106.1 (4)
C11—C5—C6—C1	178.3 (5)	P1—C31—C32—C33	121.8 (3)
C25—P1—C13—C18	−34.4 (4)	C38—C31—C32—C37	69.3 (5)
C19—P1—C13—C18	−151.2 (4)	P1—C31—C32—C37	−62.8 (5)
C31—P1—C13—C18	87.9 (4)	C37—C32—C33—C34	2.7 (6)
C25—P1—C13—C14	148.9 (3)	C31—C32—C33—C34	178.3 (4)
C19—P1—C13—C14	32.0 (4)	C32—C33—C34—C35	−0.9 (7)
C31—P1—C13—C14	−88.9 (4)	C33—C34—C35—F4	178.0 (4)
C18—C13—C14—C15	−0.2 (6)	C33—C34—C35—C36	−0.6 (8)
P1—C13—C14—C15	176.6 (3)	F4—C35—C36—C37	−178.4 (4)
C13—C14—C15—C16	0.4 (7)	C34—C35—C36—C37	0.3 (8)
C14—C15—C16—C17	−0.1 (8)	C35—C36—C37—C32	1.6 (7)
C15—C16—C17—C18	−0.5 (8)	C33—C32—C37—C36	−3.0 (6)
C14—C13—C18—C17	−0.4 (7)	C31—C32—C37—C36	−178.3 (4)
P1—C13—C18—C17	−177.1 (4)	C32—C31—C38—C39	−70.0 (5)
C16—C17—C18—C13	0.7 (8)	P1—C31—C38—C39	62.5 (5)
C13—P1—C19—C24	−124.2 (4)	C32—C31—C38—C43	106.7 (5)
C25—P1—C19—C24	117.9 (4)	P1—C31—C38—C43	−120.7 (4)
C31—P1—C19—C24	−1.3 (4)	C43—C38—C39—C40	1.5 (8)
C13—P1—C19—C20	57.2 (4)	C31—C38—C39—C40	178.3 (5)
C25—P1—C19—C20	−60.7 (4)	C38—C39—C40—C41	−1.2 (9)
C31—P1—C19—C20	−179.9 (3)	C39—C40—C41—F5	180.0 (6)
C24—C19—C20—C21	−0.6 (7)	C39—C40—C41—C42	0.2 (10)
P1—C19—C20—C21	178.0 (4)	F5—C41—C42—C43	−179.4 (5)
C19—C20—C21—C22	0.2 (7)	C40—C41—C42—C43	0.4 (10)
C20—C21—C22—C23	0.6 (7)	C39—C38—C43—C42	−1.0 (7)
C21—C22—C23—C24	−1.0 (7)	C31—C38—C43—C42	−177.8 (4)
C20—C19—C24—C23	0.3 (6)	C41—C42—C43—C38	0.0 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C30—H30A···N1ⁱ	0.95	2.66	3.535 (18)	153
C31—H31A···Br1ⁱⁱ	1.00	3.08	4.067 (4)	168
C45—H45B···N2ⁱⁱⁱ	0.98	2.62	3.38 (3)	134
C30—H30A···N1ⁱ	0.95	2.66	3.535 (18)	153
C31—H31A···Br1ⁱⁱ	1.00	3.08	4.067 (4)	168
C45—H45B···N2ⁱⁱⁱ	0.98	2.62	3.38 (3)	134

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x−1/2, −y+1/2, z−1/2.

(g) top

Crystal data top

C₃₁H₂₄BrF₂P	D_x = 1.378 Mg m⁻³ D_m = n/a Mg m⁻³ D_m measured by ?
M_r = 545.38	Melting point: 505 K
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.7103 (4) Å	Cell parameters from 9940 reflections
b = 18.0967 (6) Å	θ = 2.3–28.2°
c = 13.6486 (5) Å	µ = 1.66 mm⁻¹
β = 96.2767 (17)°	T = 200 K
V = 2629.53 (16) Å³	Block, colourless
Z = 4	0.31 × 0.20 × 0.12 mm
F(000) = 1112

Data collection top

Bruker APEX-II CCD diffractometer	5130 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.038
Absorption correction: multi-scan SADABS, Bruker (2003)	θ_max = 28.3°, θ_min = 1.9°
T_min = 0.540, T_max = 0.746	h = −14→13
23062 measured reflections	k = −22→24
6468 independent reflections	l = −18→15

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0496P)² + 0.0687P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
6468 reflections	Δρ_max = 0.74 e Å⁻³
316 parameters	Δρ_min = −0.23 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
Br1	0.22490 (2)	0.13487 (2)	0.43619 (2)	0.04784 (8)
P2	0.07493 (4)	0.22513 (2)	0.88779 (3)	0.03406 (10)
F1	0.03730 (16)	0.40892 (8)	0.46822 (10)	0.0914 (5)
F2	−0.41283 (13)	0.01830 (7)	0.69158 (12)	0.0824 (4)
C1	−0.06517 (15)	0.24476 (8)	0.80144 (12)	0.0345 (3)
H1A	−0.1159	0.2800	0.8373	0.041*
C2	−0.03418 (14)	0.28687 (8)	0.71026 (12)	0.0348 (3)
C3	0.00555 (17)	0.25307 (10)	0.62718 (13)	0.0437 (4)
H3A	0.0156	0.2009	0.6264	0.052*
C4	0.03064 (18)	0.29387 (11)	0.54581 (14)	0.0502 (4)
H4A	0.0597	0.2706	0.4902	0.060*
C5	0.0123 (2)	0.36875 (11)	0.54776 (15)	0.0545 (5)
C6	−0.0285 (2)	0.40439 (10)	0.62622 (15)	0.0539 (5)
H6A	−0.0411	0.4564	0.6249	0.065*
C7	−0.05125 (18)	0.36317 (9)	0.70815 (14)	0.0438 (4)
H7A	−0.0789	0.3874	0.7637	0.053*
C8	−0.15161 (16)	0.17846 (8)	0.77687 (12)	0.0369 (3)
C9	−0.27797 (17)	0.19013 (10)	0.78484 (15)	0.0491 (4)
H9A	−0.3041	0.2360	0.8097	0.059*
C10	−0.3666 (2)	0.13647 (12)	0.75734 (19)	0.0631 (6)
H10A	−0.4533	0.1448	0.7625	0.076*
C11	−0.3253 (2)	0.07062 (11)	0.72223 (16)	0.0571 (5)
C12	−0.2030 (2)	0.05595 (10)	0.71450 (16)	0.0561 (5)
H12A	−0.1781	0.0094	0.6911	0.067*
C13	−0.11431 (19)	0.11058 (10)	0.74164 (15)	0.0487 (4)
H13A	−0.0280	0.1015	0.7361	0.058*
C14	0.16143 (15)	0.30955 (9)	0.91195 (12)	0.0362 (3)
C15	0.09795 (18)	0.37143 (9)	0.94162 (15)	0.0456 (4)
H15A	0.0100	0.3695	0.9454	0.055*
C16	0.16417 (19)	0.43584 (10)	0.96559 (15)	0.0531 (5)
H16A	0.1212	0.4785	0.9849	0.064*
C17	0.2917 (2)	0.43838 (11)	0.96161 (15)	0.0535 (5)
H17A	0.3364	0.4828	0.9780	0.064*
C18	0.35559 (19)	0.37695 (11)	0.93400 (16)	0.0526 (5)
H18A	0.4440	0.3788	0.9324	0.063*
C19	0.29005 (16)	0.31247 (10)	0.90867 (14)	0.0452 (4)
H19A	0.3335	0.2702	0.8890	0.054*
C20	0.02941 (16)	0.19444 (9)	1.00369 (12)	0.0396 (4)
C21	−0.09399 (18)	0.19003 (11)	1.02372 (14)	0.0512 (4)
H21A	−0.1602	0.2041	0.9753	0.061*
C22	−0.1204 (2)	0.16487 (13)	1.11547 (17)	0.0644 (6)
H22A	−0.2051	0.1623	1.1299	0.077*
C23	−0.0258 (3)	0.14380 (13)	1.18501 (17)	0.0672 (6)
H23A	−0.0451	0.1248	1.2465	0.081*
C24	0.0970 (2)	0.14986 (14)	1.16656 (17)	0.0688 (6)
H24A	0.1628	0.1361	1.2156	0.083*
C25	0.1249 (2)	0.17610 (13)	1.07640 (15)	0.0591 (5)
H25A	0.2100	0.1816	1.0642	0.071*
C26	0.17181 (16)	0.15494 (10)	0.84172 (14)	0.0436 (4)
C27	0.23129 (18)	0.16827 (13)	0.75753 (15)	0.0550 (5)
H27A	0.2296	0.2162	0.7290	0.066*
C28	0.2937 (2)	0.11005 (18)	0.71545 (17)	0.0734 (7)
H28A	0.3323	0.1179	0.6569	0.088*
C29	0.2987 (2)	0.04218 (15)	0.7591 (2)	0.0807 (8)
H29A	0.3417	0.0030	0.7307	0.097*
C30	0.2436 (2)	0.02966 (13)	0.8417 (2)	0.0794 (7)
H30A	0.2503	−0.0177	0.8719	0.095*
C31	0.1773 (2)	0.08517 (10)	0.88304 (18)	0.0595 (5)
H31A	0.1358	0.0753	0.9397	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.05151 (12)	0.04394 (11)	0.04840 (13)	−0.00252 (7)	0.00687 (9)	0.00800 (7)
P2	0.0360 (2)	0.0346 (2)	0.0314 (2)	0.00084 (15)	0.00276 (16)	0.00067 (15)
F1	0.1328 (13)	0.0846 (10)	0.0611 (9)	−0.0088 (9)	0.0306 (9)	0.0300 (7)
F2	0.0844 (9)	0.0650 (8)	0.0985 (11)	−0.0434 (7)	0.0139 (8)	−0.0182 (7)
C1	0.0356 (8)	0.0334 (7)	0.0339 (8)	−0.0006 (6)	0.0010 (6)	−0.0011 (6)
C2	0.0350 (8)	0.0356 (8)	0.0324 (8)	−0.0018 (6)	−0.0030 (6)	0.0010 (6)
C3	0.0487 (10)	0.0416 (9)	0.0396 (9)	0.0040 (7)	−0.0004 (8)	−0.0015 (7)
C4	0.0506 (10)	0.0642 (12)	0.0362 (9)	−0.0011 (9)	0.0065 (8)	−0.0021 (8)
C5	0.0610 (12)	0.0609 (12)	0.0420 (11)	−0.0085 (9)	0.0071 (9)	0.0142 (9)
C6	0.0709 (13)	0.0396 (9)	0.0510 (11)	−0.0026 (8)	0.0053 (10)	0.0095 (8)
C7	0.0539 (11)	0.0378 (9)	0.0393 (9)	−0.0019 (7)	0.0036 (8)	−0.0012 (7)
C8	0.0437 (9)	0.0347 (8)	0.0318 (8)	−0.0049 (6)	0.0012 (7)	−0.0003 (6)
C9	0.0462 (10)	0.0473 (10)	0.0547 (12)	−0.0057 (8)	0.0097 (9)	−0.0117 (8)
C10	0.0491 (12)	0.0684 (14)	0.0736 (16)	−0.0179 (9)	0.0154 (11)	−0.0152 (11)
C11	0.0693 (13)	0.0474 (10)	0.0545 (12)	−0.0285 (9)	0.0065 (10)	−0.0030 (9)
C12	0.0742 (14)	0.0342 (9)	0.0584 (12)	−0.0066 (8)	0.0005 (10)	−0.0057 (8)
C13	0.0536 (11)	0.0382 (9)	0.0533 (11)	0.0006 (8)	0.0015 (9)	−0.0057 (8)
C14	0.0370 (8)	0.0406 (8)	0.0298 (8)	−0.0044 (6)	−0.0016 (6)	0.0008 (6)
C15	0.0413 (9)	0.0493 (10)	0.0456 (10)	0.0002 (7)	0.0024 (8)	−0.0068 (8)
C16	0.0617 (12)	0.0449 (10)	0.0519 (12)	0.0002 (9)	0.0030 (9)	−0.0102 (8)
C17	0.0624 (12)	0.0493 (10)	0.0468 (11)	−0.0176 (9)	−0.0032 (9)	−0.0030 (8)
C18	0.0408 (10)	0.0667 (12)	0.0498 (11)	−0.0108 (9)	0.0024 (8)	−0.0015 (9)
C19	0.0396 (9)	0.0488 (10)	0.0465 (10)	0.0020 (7)	0.0017 (8)	−0.0008 (8)
C20	0.0461 (9)	0.0404 (8)	0.0322 (8)	−0.0025 (7)	0.0036 (7)	0.0013 (7)
C21	0.0499 (11)	0.0620 (11)	0.0425 (10)	0.0076 (9)	0.0085 (8)	0.0074 (9)
C22	0.0654 (14)	0.0783 (14)	0.0532 (13)	0.0013 (11)	0.0237 (11)	0.0083 (11)
C23	0.0856 (17)	0.0777 (15)	0.0397 (11)	−0.0040 (12)	0.0138 (11)	0.0146 (10)
C24	0.0719 (15)	0.0884 (16)	0.0426 (12)	−0.0040 (12)	−0.0083 (11)	0.0171 (11)
C25	0.0495 (11)	0.0805 (14)	0.0454 (11)	−0.0082 (10)	−0.0033 (9)	0.0116 (10)
C26	0.0387 (9)	0.0441 (9)	0.0469 (10)	0.0077 (7)	0.0001 (8)	−0.0053 (8)
C27	0.0452 (10)	0.0748 (13)	0.0444 (11)	0.0127 (9)	0.0025 (8)	−0.0023 (10)
C28	0.0504 (12)	0.122 (2)	0.0470 (12)	0.0174 (13)	0.0001 (10)	−0.0247 (14)
C29	0.0694 (16)	0.0782 (17)	0.091 (2)	0.0267 (13)	−0.0089 (14)	−0.0369 (15)
C30	0.0761 (16)	0.0502 (12)	0.110 (2)	0.0168 (11)	0.0015 (15)	−0.0166 (13)
C31	0.0598 (12)	0.0418 (10)	0.0770 (15)	0.0073 (8)	0.0077 (11)	−0.0035 (9)

Geometric parameters (Å, º) top

P2—C20	1.7936 (17)	C12—C13	1.393 (3)
P2—C26	1.7967 (17)	C14—C19	1.384 (2)
P2—C14	1.7984 (16)	C14—C15	1.393 (2)
P2—C1	1.8385 (16)	C15—C16	1.385 (2)
F1—C5	1.357 (2)	C16—C17	1.374 (3)
F2—C11	1.365 (2)	C17—C18	1.379 (3)
C1—C2	1.526 (2)	C18—C19	1.386 (3)
C1—C8	1.530 (2)	C20—C21	1.381 (2)
C2—C7	1.393 (2)	C20—C25	1.385 (3)
C2—C3	1.395 (2)	C21—C22	1.390 (3)
C3—C4	1.384 (3)	C22—C23	1.365 (3)
C4—C5	1.370 (3)	C23—C24	1.370 (4)
C5—C6	1.362 (3)	C24—C25	1.382 (3)
C6—C7	1.388 (3)	C26—C31	1.382 (3)
C8—C9	1.386 (2)	C26—C27	1.394 (3)
C8—C13	1.394 (2)	C27—C28	1.404 (3)
C9—C10	1.381 (3)	C28—C29	1.363 (4)
C10—C11	1.376 (3)	C29—C30	1.348 (4)
C11—C12	1.352 (3)	C30—C31	1.385 (3)

C20—P2—C26	108.23 (8)	C11—C12—C13	118.58 (18)
C20—P2—C14	106.60 (8)	C8—C13—C12	120.30 (18)
C26—P2—C14	111.05 (8)	C19—C14—C15	119.86 (15)
C20—P2—C1	110.10 (8)	C19—C14—P2	121.40 (13)
C26—P2—C1	111.98 (8)	C15—C14—P2	118.57 (13)
C14—P2—C1	108.75 (7)	C16—C15—C14	119.44 (17)
C2—C1—C8	113.15 (13)	C17—C16—C15	120.31 (17)
C2—C1—P2	112.59 (10)	C16—C17—C18	120.57 (17)
C8—C1—P2	114.89 (11)	C17—C18—C19	119.62 (18)
C7—C2—C3	117.96 (16)	C14—C19—C18	120.18 (17)
C7—C2—C1	118.17 (15)	C21—C20—C25	119.46 (17)
C3—C2—C1	123.82 (14)	C21—C20—P2	123.43 (14)
C4—C3—C2	121.43 (16)	C25—C20—P2	117.10 (14)
C5—C4—C3	118.11 (18)	C20—C21—C22	119.40 (19)
F1—C5—C6	118.92 (18)	C23—C22—C21	120.6 (2)
F1—C5—C4	118.23 (19)	C22—C23—C24	120.3 (2)
C6—C5—C4	122.85 (17)	C23—C24—C25	119.8 (2)
C5—C6—C7	118.60 (17)	C24—C25—C20	120.4 (2)
C6—C7—C2	121.02 (17)	C31—C26—C27	119.44 (18)
C9—C8—C13	118.73 (15)	C31—C26—P2	120.25 (15)
C9—C8—C1	115.86 (14)	C27—C26—P2	119.97 (15)
C13—C8—C1	125.27 (15)	C26—C27—C28	119.2 (2)
C10—C9—C8	121.33 (17)	C29—C28—C27	119.7 (2)
C11—C10—C9	117.8 (2)	C30—C29—C28	121.1 (2)
C12—C11—F2	118.59 (18)	C29—C30—C31	120.6 (2)
C12—C11—C10	123.29 (18)	C26—C31—C30	119.8 (2)
F2—C11—C10	118.1 (2)

C20—P2—C1—C2	167.32 (11)	C26—P2—C14—C15	175.59 (14)
C26—P2—C1—C2	−72.22 (13)	C1—P2—C14—C15	51.94 (16)
C14—P2—C1—C2	50.87 (13)	C19—C14—C15—C16	1.3 (3)
C20—P2—C1—C8	−61.19 (13)	P2—C14—C15—C16	176.61 (15)
C26—P2—C1—C8	59.27 (14)	C14—C15—C16—C17	−1.0 (3)
C14—P2—C1—C8	−177.64 (11)	C15—C16—C17—C18	−0.2 (3)
C8—C1—C2—C7	129.20 (16)	C16—C17—C18—C19	1.0 (3)
P2—C1—C2—C7	−98.45 (16)	C15—C14—C19—C18	−0.6 (3)
C8—C1—C2—C3	−48.2 (2)	P2—C14—C19—C18	−175.69 (15)
P2—C1—C2—C3	84.20 (17)	C17—C18—C19—C14	−0.6 (3)
C7—C2—C3—C4	1.7 (3)	C26—P2—C20—C21	−125.29 (16)
C1—C2—C3—C4	179.02 (16)	C14—P2—C20—C21	115.19 (16)
C2—C3—C4—C5	−1.6 (3)	C1—P2—C20—C21	−2.59 (18)
C3—C4—C5—F1	179.76 (18)	C26—P2—C20—C25	56.19 (17)
C3—C4—C5—C6	0.4 (3)	C14—P2—C20—C25	−63.33 (17)
F1—C5—C6—C7	−178.63 (19)	C1—P2—C20—C25	178.89 (15)
C4—C5—C6—C7	0.7 (3)	C25—C20—C21—C22	−2.2 (3)
C5—C6—C7—C2	−0.7 (3)	P2—C20—C21—C22	179.36 (16)
C3—C2—C7—C6	−0.5 (3)	C20—C21—C22—C23	−0.8 (3)
C1—C2—C7—C6	−178.01 (17)	C21—C22—C23—C24	2.5 (4)
C2—C1—C8—C9	−98.18 (18)	C22—C23—C24—C25	−1.2 (4)
P2—C1—C8—C9	130.60 (15)	C23—C24—C25—C20	−1.7 (4)
C2—C1—C8—C13	77.4 (2)	C21—C20—C25—C24	3.4 (3)
P2—C1—C8—C13	−53.9 (2)	P2—C20—C25—C24	−178.01 (19)
C13—C8—C9—C10	−0.9 (3)	C20—P2—C26—C31	13.73 (19)
C1—C8—C9—C10	174.91 (19)	C14—P2—C26—C31	130.40 (16)
C8—C9—C10—C11	0.4 (3)	C1—P2—C26—C31	−107.82 (17)
C9—C10—C11—C12	0.7 (4)	C20—P2—C26—C27	−173.04 (15)
C9—C10—C11—F2	−177.7 (2)	C14—P2—C26—C27	−56.37 (18)
F2—C11—C12—C13	177.17 (18)	C1—P2—C26—C27	65.41 (17)
C10—C11—C12—C13	−1.2 (3)	C31—C26—C27—C28	1.1 (3)
C9—C8—C13—C12	0.4 (3)	P2—C26—C27—C28	−172.16 (16)
C1—C8—C13—C12	−175.01 (17)	C26—C27—C28—C29	−2.0 (3)
C11—C12—C13—C8	0.6 (3)	C27—C28—C29—C30	0.6 (4)
C20—P2—C14—C19	108.46 (15)	C28—C29—C30—C31	1.8 (4)
C26—P2—C14—C19	−9.22 (17)	C27—C26—C31—C30	1.2 (3)
C1—P2—C14—C19	−132.87 (14)	P2—C26—C31—C30	174.47 (18)
C20—P2—C14—C15	−66.74 (16)	C29—C30—C31—C26	−2.7 (4)

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Format		BIBTeX
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		Text
		Plain Text