Structural investigations of phosphorus–nitrogen compounds. 4. Steric and electronic effects in dibenzylamino derivatives of hexachlorocyclotriphosphazatriene and 4,4,6,6-tetrachloro-2,2-di­phenylcyclotriphosphazatriene

A systematic study is presented on the products of aminolysis of N₃P₃Cl₆ (1) and N₃P₃Ph₂Cl₄ (4) with dibenzylamine. Two series of mono- and disubstituted derivatives of compounds (1) and (4), namely N₃P₃Cl₅[N(CH₂Ph)₂] (2) and N₃P₃Cl₄[N(CH₂Ph)₂]₂ (3) and N₃P₃Ph₂Cl₃[N(CH₂Ph)₂] (5) and N₃P₃Ph₂Cl₂[N(CH₂Ph)₂]₂ (6) [where (2), (3), (5) and (6) are new structures], are investigated in order to determine whether steric or electronic effects prevail in the formation of dibenzylamino-substituted cyclophosphazenes. The influence of an electron-releasing group (i.e. phenyl) on the stereochemistry and degree of substitution of the product is analysed by comparison of the above two series. The difference in unsymmetrically substituted endocyclic P—N bond lengths, Δ, is used as a measure of the degree of the electronic contribution, in combination with basicity constants, to quantify the degree of the electron-releasing capacity of the R group. In order to compare geminal versus non-geminal substitution, a difunctional secondary amine was used to form the compound N₃P₃Cl₄[NMe(CH₂)₃NMe] (7) (a reinvestigation) for inclusion in this study. It is shown that electron-releasing groups have a greater effect on the lengthening of P—Cl bonds as opposed to endocyclic P—N bonds and that this effect is greater in the non-geminal PRCl case than for geminal PCl₂. However, steric effects are shown to be dominant in the reactions of dibenzylamine with N₃P₃ derivatives, with a disposition to a trans stereochemistry in bisdibenzylamino derivatives.

Computing details

Data collection: DENZO, COLLECT for (2), (5); DENZO and COLLECT for (3), (6), (7). Cell refinement: DENZO, COLLECT for (2), (5); DENZO and COLLECT for (3), (6), (7). Data reduction: DENZO, COLLECT for (2), (5); DENZO and COLLECT for (3), (6), (7). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990).

(2)

Crystal data

C14H14Cl5N4P3	F(000) = 1024
Mr = 508.45	Dx = 1.598 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.125 (2) Å	Cell parameters from 8236 reflections
b = 8.1671 (16) Å	θ = 2.9–27.5°
c = 23.585 (5) Å	µ = 0.92 mm^−1
β = 99.61 (3)°	T = 120 K
V = 2112.9 (7) Å^3	Block, colourless
Z = 4	0.35 × 0.20 × 0.16 mm

Data collection

Nonius KappaCCD Area Detector diffractometer	4790 independent reflections
Radiation source: Nonius FR591 rotating anode	4054 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
φ and ω scans	h = −14→14
Absorption correction: multi-scans SORTAV (Blessing, 1997)	k = −8→10
Tmin = 0.739, Tmax = 0.867	l = −30→23
11630 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0394P)^2 + 0.4555P] where P = (Fo^2 + 2Fc^2)/3
4790 reflections	(Δ/σ)max = 0.056
236 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.76657 (15)	0.1008 (2)	0.15008 (7)	0.0192 (3)
H1A	0.8329	0.0353	0.1725	0.023*
H1B	0.7179	0.0267	0.1219	0.023*
C2	0.68555 (16)	0.1665 (2)	0.19059 (7)	0.0214 (4)
C3	0.57300 (17)	0.2344 (2)	0.16923 (8)	0.0288 (4)
H3	0.5466	0.2405	0.1288	0.035*
C4	0.49853 (19)	0.2935 (3)	0.20631 (10)	0.0373 (5)
H4	0.4214	0.3395	0.1913	0.045*
C5	0.5365 (2)	0.2854 (3)	0.26490 (10)	0.0380 (5)
H5	0.4854	0.3256	0.2902	0.046*
C6	0.6482 (2)	0.2191 (2)	0.28675 (8)	0.0332 (5)
H6	0.6742	0.2142	0.3272	0.040*
C7	0.72368 (17)	0.1589 (2)	0.24985 (7)	0.0250 (4)
H7	0.8007	0.1128	0.2651	0.030*
C8	0.90080 (15)	0.3471 (2)	0.15478 (7)	0.0186 (3)
H8A	0.8542	0.3999	0.1821	0.022*
H8B	0.9268	0.4338	0.1301	0.022*
C9	1.01218 (15)	0.2647 (2)	0.18810 (7)	0.0183 (3)
C10	1.08764 (16)	0.1675 (2)	0.16033 (7)	0.0224 (4)
H10	1.0685	0.1514	0.1199	0.027*
C11	1.18983 (16)	0.0946 (2)	0.19120 (7)	0.0259 (4)
H11	1.2409	0.0292	0.1719	0.031*
C12	1.21870 (16)	0.1162 (2)	0.25063 (7)	0.0264 (4)
H12	1.2889	0.0653	0.2718	0.032*
C13	1.14404 (17)	0.2126 (2)	0.27841 (7)	0.0252 (4)
H13	1.1630	0.2279	0.3188	0.030*
C14	1.04173 (16)	0.2867 (2)	0.24725 (7)	0.0214 (4)
H14	0.9913	0.3532	0.2665	0.026*
N1	0.77940 (13)	0.1479 (2)	−0.07210 (6)	0.0246 (3)
N2	0.87591 (14)	0.3321 (2)	0.02008 (6)	0.0279 (4)
N3	0.67593 (13)	0.1426 (2)	0.02445 (6)	0.0261 (3)
N4	0.82110 (12)	0.22991 (17)	0.11852 (5)	0.0180 (3)
P1	0.67448 (4)	0.08730 (6)	−0.039398 (17)	0.01989 (12)
P2	0.87231 (4)	0.28465 (6)	−0.044403 (17)	0.02209 (12)
P3	0.76721 (4)	0.28101 (6)	0.052933 (17)	0.02011 (12)
Cl1	0.66928 (4)	−0.15591 (6)	−0.04240 (2)	0.03100 (13)
Cl2	0.51442 (4)	0.14795 (6)	−0.087255 (18)	0.02753 (12)
Cl3	0.84497 (5)	0.48458 (6)	−0.094215 (19)	0.03344 (13)
Cl4	1.03912 (4)	0.21748 (7)	−0.05544 (2)	0.03996 (14)
Cl5	0.66856 (5)	0.49056 (6)	0.05622 (2)	0.03840 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0214 (8)	0.0186 (9)	0.0171 (7)	−0.0042 (7)	0.0014 (6)	0.0019 (7)
C2	0.0227 (9)	0.0192 (9)	0.0232 (8)	−0.0069 (7)	0.0060 (7)	0.0000 (7)
C3	0.0217 (9)	0.0338 (11)	0.0299 (9)	−0.0055 (8)	0.0020 (7)	−0.0020 (8)
C4	0.0237 (10)	0.0358 (12)	0.0544 (13)	−0.0035 (9)	0.0122 (9)	−0.0074 (10)
C5	0.0410 (12)	0.0294 (11)	0.0508 (13)	−0.0120 (9)	0.0289 (10)	−0.0135 (10)
C6	0.0529 (13)	0.0232 (10)	0.0274 (10)	−0.0114 (9)	0.0185 (9)	−0.0043 (8)
C7	0.0323 (10)	0.0211 (9)	0.0220 (8)	−0.0050 (8)	0.0057 (7)	0.0023 (7)
C8	0.0215 (8)	0.0182 (8)	0.0155 (7)	−0.0026 (7)	0.0013 (6)	−0.0013 (6)
C9	0.0175 (8)	0.0190 (8)	0.0177 (7)	−0.0043 (7)	0.0013 (6)	0.0009 (6)
C10	0.0250 (9)	0.0267 (10)	0.0161 (8)	−0.0035 (7)	0.0050 (6)	−0.0023 (7)
C11	0.0233 (9)	0.0297 (10)	0.0257 (9)	0.0023 (8)	0.0071 (7)	−0.0015 (8)
C12	0.0188 (9)	0.0337 (11)	0.0255 (9)	0.0001 (8)	−0.0001 (7)	0.0014 (8)
C13	0.0260 (9)	0.0318 (10)	0.0161 (8)	−0.0029 (8)	−0.0013 (6)	−0.0029 (7)
C14	0.0218 (9)	0.0250 (9)	0.0174 (8)	−0.0032 (7)	0.0032 (6)	−0.0036 (7)
N1	0.0226 (8)	0.0331 (9)	0.0183 (7)	−0.0095 (7)	0.0039 (5)	−0.0030 (6)
N2	0.0269 (8)	0.0387 (10)	0.0175 (7)	−0.0166 (7)	0.0016 (6)	−0.0011 (6)
N3	0.0231 (8)	0.0389 (9)	0.0164 (7)	−0.0132 (7)	0.0030 (5)	−0.0018 (6)
N4	0.0188 (7)	0.0197 (7)	0.0147 (6)	−0.0042 (6)	0.0006 (5)	−0.0004 (5)
P1	0.0169 (2)	0.0257 (3)	0.0160 (2)	−0.00652 (17)	−0.00026 (15)	−0.00009 (17)
P2	0.0171 (2)	0.0332 (3)	0.0154 (2)	−0.00861 (19)	0.00118 (16)	0.00068 (18)
P3	0.0193 (2)	0.0258 (3)	0.0144 (2)	−0.00533 (18)	0.00035 (16)	0.00096 (17)
Cl1	0.0309 (3)	0.0255 (2)	0.0339 (2)	−0.00407 (19)	−0.00267 (18)	0.00194 (19)
Cl2	0.0208 (2)	0.0342 (3)	0.0250 (2)	−0.00284 (18)	−0.00374 (16)	0.00330 (18)
Cl3	0.0353 (3)	0.0393 (3)	0.0235 (2)	−0.0130 (2)	−0.00135 (18)	0.00832 (19)
Cl4	0.0194 (2)	0.0598 (4)	0.0412 (3)	−0.0035 (2)	0.00659 (19)	−0.0020 (2)
Cl5	0.0391 (3)	0.0333 (3)	0.0402 (3)	0.0103 (2)	−0.0009 (2)	0.0092 (2)

Geometric parameters (Å, º)

C1—N4	1.478 (2)	C12—C13	1.386 (3)
C1—C2	1.517 (2)	C13—C14	1.386 (3)
C2—C3	1.385 (3)	N1—P1	1.5820 (15)
C2—C7	1.393 (2)	N1—P2	1.5868 (15)
C3—C4	1.388 (3)	N2—P2	1.5634 (15)
C4—C5	1.377 (3)	N2—P3	1.5969 (15)
C5—C6	1.375 (3)	N3—P1	1.5696 (14)
C6—C7	1.396 (3)	N3—P3	1.5915 (16)
C8—N4	1.477 (2)	N4—P3	1.6177 (14)
C8—C9	1.510 (2)	P1—Cl1	1.9881 (8)
C9—C14	1.391 (2)	P1—Cl2	2.0048 (8)
C9—C10	1.396 (2)	P2—Cl4	1.9935 (8)
C10—C11	1.379 (3)	P2—Cl3	2.0049 (7)
C11—C12	1.396 (2)	P3—Cl5	2.0415 (8)
N4—C1—C2	113.68 (14)	C8—N4—C1	115.36 (12)
C3—C2—C7	119.23 (16)	C8—N4—P3	118.51 (11)
C3—C2—C1	120.58 (15)	C1—N4—P3	123.21 (11)
C7—C2—C1	120.19 (16)	N3—P1—N1	119.18 (8)
C2—C3—C4	120.57 (18)	N3—P1—Cl1	108.50 (7)
C5—C4—C3	120.0 (2)	N1—P1—Cl1	108.33 (7)
C6—C5—C4	120.09 (18)	N3—P1—Cl2	109.57 (7)
C5—C6—C7	120.36 (18)	N1—P1—Cl2	107.85 (6)
C2—C7—C6	119.73 (19)	Cl1—P1—Cl2	102.06 (3)
N4—C8—C9	111.93 (14)	N2—P2—N1	118.97 (8)
C14—C9—C10	118.97 (16)	N2—P2—Cl4	108.78 (7)
C14—C9—C8	120.03 (15)	N1—P2—Cl4	108.01 (6)
C10—C9—C8	121.00 (14)	N2—P2—Cl3	110.16 (7)
C11—C10—C9	120.36 (15)	N1—P2—Cl3	107.90 (6)
C10—C11—C12	120.45 (16)	Cl4—P2—Cl3	101.60 (3)
C13—C12—C11	119.40 (17)	N3—P3—N2	117.55 (8)
C12—C13—C14	120.08 (16)	N3—P3—N4	109.20 (8)
C13—C14—C9	120.73 (16)	N2—P3—N4	109.97 (8)
P1—N1—P2	120.15 (9)	N3—P3—Cl5	107.59 (7)
P2—N2—P3	120.57 (10)	N2—P3—Cl5	104.76 (7)
P1—N3—P3	120.86 (9)	N4—P3—Cl5	107.20 (6)

(3)

Crystal data

C28H28Cl4N5P3	Dx = 1.465 Mg m^−3
Mr = 669.26	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 12469 reflections
a = 18.294 (4) Å	θ = 2.5–27.5°
b = 17.411 (4) Å	µ = 0.58 mm^−1
c = 19.047 (4) Å	T = 150 K
V = 6067 (2) Å^3	Block, colourless
Z = 8	0.63 × 0.63 × 0.33 mm
F(000) = 2752

Data collection

Nonius KappaCCD diffractometer	5347 independent reflections
Radiation source: Nonius FR591 rotating anode	3833 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
Detector resolution: 9.091 pixels mm^-1	θmax = 25.0°, θmin = 3.1°
φ and ω scans	h = −21→21
Absorption correction: multi-scans SORTAV (Blessing, 1997)	k = −20→20
Tmin = 0.714, Tmax = 0.835	l = −22→14
22246 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 0.87	w = 1/[σ^2(Fo^2) + (0.0695P)^2 + 0.6558P] where P = (Fo^2 + 2Fc^2)/3
5347 reflections	(Δ/σ)max = 0.023
466 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
H1B	0.0439 (16)	0.5184 (15)	0.3072 (13)	0.023 (7)*
H15A	0.0241 (14)	0.5946 (15)	0.0797 (12)	0.021 (7)*
H15B	−0.0132 (13)	0.6442 (14)	0.0188 (13)	0.017 (7)*
H11	0.1231 (15)	0.7714 (16)	0.5313 (13)	0.026 (8)*
H22B	−0.1556 (15)	0.6720 (15)	0.0722 (13)	0.028 (7)*
H22A	−0.1432 (15)	0.7324 (15)	0.1319 (13)	0.028 (7)*
H10	0.1400 (15)	0.7409 (16)	0.4142 (14)	0.032 (8)*
H3	0.1795 (13)	0.4160 (13)	0.3910 (12)	0.013 (7)*
H8B	0.2127 (14)	0.6537 (14)	0.3326 (12)	0.020 (7)*
H8A	0.2231 (14)	0.5661 (15)	0.3572 (11)	0.020 (7)*
H19	−0.2037 (17)	0.3890 (18)	−0.0019 (14)	0.048 (9)*
H24	−0.1897 (15)	0.7432 (15)	−0.0266 (13)	0.022 (8)*
H7	0.1104 (16)	0.4671 (16)	0.1970 (14)	0.035 (8)*
H28	−0.0173 (16)	0.8187 (16)	0.0814 (15)	0.035 (8)*
H12	0.1412 (19)	0.6883 (19)	0.6196 (17)	0.063 (11)*
H1A	0.0875 (15)	0.5077 (15)	0.3780 (14)	0.033 (8)*
H14	0.2012 (16)	0.5275 (17)	0.4728 (14)	0.039 (8)*
H4	0.2515 (19)	0.3174 (19)	0.3437 (16)	0.056 (10)*
H21	−0.1023 (14)	0.5866 (16)	−0.0564 (13)	0.026 (7)*
H5	0.2586 (19)	0.2981 (19)	0.2243 (15)	0.051 (10)*
H27	0.0035 (18)	0.9110 (19)	−0.0013 (15)	0.044 (10)*
H18	−0.1429 (16)	0.3921 (17)	0.1099 (15)	0.043 (9)*
H26	−0.076 (2)	0.931 (2)	−0.0926 (17)	0.069 (11)*
H17	−0.0627 (16)	0.4920 (16)	0.1308 (14)	0.035 (9)*
H6	0.1903 (18)	0.3730 (18)	0.1521 (17)	0.056 (11)*
H20	−0.1790 (15)	0.4870 (15)	−0.0825 (15)	0.036 (8)*
P3	0.02720 (4)	0.78213 (4)	0.27086 (4)	0.02553 (19)
P2	−0.03604 (4)	0.66534 (4)	0.19576 (4)	0.02503 (19)
Cl1	0.18897 (4)	0.64233 (4)	0.18449 (3)	0.0318 (2)
P1	0.10201 (4)	0.64748 (4)	0.25162 (3)	0.02082 (18)
Cl4	−0.00870 (4)	0.80337 (4)	0.36838 (3)	0.0362 (2)
Cl3	0.05210 (5)	0.88825 (4)	0.23858 (4)	0.0402 (2)
Cl2	−0.12249 (4)	0.61134 (5)	0.24201 (4)	0.0444 (2)
N5	−0.05445 (12)	0.66765 (12)	0.11239 (10)	0.0220 (5)
N1	0.03379 (12)	0.61421 (12)	0.21090 (11)	0.0241 (5)
N4	0.12332 (12)	0.59309 (12)	0.31764 (11)	0.0226 (5)
N2	−0.03759 (13)	0.75048 (14)	0.22567 (12)	0.0371 (6)
C8	0.19002 (16)	0.61142 (18)	0.35839 (14)	0.0267 (7)
C15	−0.02273 (15)	0.61383 (16)	0.06038 (15)	0.0224 (6)
C14	0.18438 (18)	0.57924 (19)	0.48732 (15)	0.0382 (8)
N3	0.10024 (12)	0.73572 (12)	0.27497 (11)	0.0246 (5)
C9	0.17412 (15)	0.63205 (16)	0.43396 (14)	0.0257 (6)
C7	0.14215 (17)	0.43827 (16)	0.22749 (15)	0.0306 (7)
C2	0.13935 (14)	0.45193 (15)	0.29905 (13)	0.0240 (6)
C1	0.09250 (16)	0.51563 (16)	0.32832 (15)	0.0245 (6)
C10	0.15049 (16)	0.70495 (16)	0.45107 (15)	0.0273 (7)
C11	0.13789 (16)	0.72465 (18)	0.52064 (15)	0.0313 (7)
C23	−0.10666 (15)	0.76955 (15)	0.03595 (13)	0.0258 (6)
C22	−0.12108 (16)	0.70825 (17)	0.09024 (15)	0.0264 (7)
C16	−0.07343 (15)	0.54942 (15)	0.04178 (12)	0.0219 (6)
C20	−0.15745 (18)	0.48828 (17)	−0.03819 (17)	0.0355 (8)
C21	−0.10946 (16)	0.54741 (17)	−0.02208 (14)	0.0290 (7)
C18	−0.13401 (18)	0.43125 (17)	0.07303 (18)	0.0388 (8)
C28	−0.04837 (18)	0.81973 (18)	0.04301 (16)	0.0355 (8)
C3	0.18183 (17)	0.40607 (16)	0.34279 (16)	0.0315 (7)
C12	0.14932 (18)	0.67203 (19)	0.57307 (17)	0.0371 (8)
C17	−0.08619 (17)	0.48987 (17)	0.08889 (16)	0.0318 (7)
C4	0.22572 (18)	0.34942 (17)	0.31491 (19)	0.0385 (8)
C19	−0.16989 (18)	0.43053 (18)	0.00997 (17)	0.0378 (8)
C6	0.18633 (18)	0.38153 (18)	0.20015 (18)	0.0399 (8)
C5	0.22855 (19)	0.33686 (18)	0.24447 (18)	0.0396 (8)
C24	−0.15325 (19)	0.7785 (2)	−0.02065 (16)	0.0389 (8)
C25	−0.14195 (19)	0.8371 (2)	−0.06840 (17)	0.0533 (10)
H25	−0.1739	0.8430	−0.1060	0.064*
C27	−0.0370 (2)	0.8778 (2)	−0.00496 (17)	0.0433 (9)
C26	−0.0840 (2)	0.8866 (2)	−0.06109 (19)	0.0493 (10)
C13	0.17199 (19)	0.59916 (19)	0.55651 (16)	0.0443 (9)
H13	0.1790	0.5631	0.5919	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P3	0.0283 (4)	0.0221 (4)	0.0262 (4)	0.0052 (3)	−0.0025 (3)	−0.0064 (3)
P2	0.0208 (4)	0.0289 (4)	0.0254 (4)	0.0021 (3)	−0.0029 (3)	−0.0057 (3)
Cl1	0.0309 (4)	0.0324 (4)	0.0320 (4)	−0.0026 (3)	0.0083 (3)	−0.0070 (3)
P1	0.0195 (4)	0.0203 (4)	0.0226 (4)	0.0010 (3)	−0.0017 (3)	−0.0036 (3)
Cl4	0.0366 (5)	0.0435 (5)	0.0286 (4)	0.0036 (4)	0.0042 (3)	−0.0092 (3)
Cl3	0.0510 (5)	0.0255 (4)	0.0442 (5)	0.0090 (4)	0.0047 (4)	0.0039 (3)
Cl2	0.0302 (5)	0.0705 (6)	0.0326 (4)	−0.0050 (4)	0.0065 (3)	0.0046 (4)
N5	0.0191 (13)	0.0230 (12)	0.0240 (12)	0.0035 (10)	−0.0001 (9)	−0.0019 (9)
N1	0.0224 (13)	0.0217 (12)	0.0282 (13)	0.0004 (10)	−0.0072 (10)	−0.0059 (10)
N4	0.0197 (13)	0.0214 (12)	0.0268 (12)	−0.0016 (10)	−0.0055 (9)	−0.0028 (9)
N2	0.0317 (15)	0.0372 (15)	0.0425 (15)	0.0151 (13)	−0.0130 (11)	−0.0188 (12)
C8	0.0192 (16)	0.0288 (16)	0.0320 (17)	0.0021 (14)	−0.0034 (12)	−0.0039 (13)
C15	0.0200 (16)	0.0246 (15)	0.0225 (15)	0.0006 (13)	0.0022 (12)	0.0024 (12)
C14	0.049 (2)	0.0320 (18)	0.0335 (19)	0.0101 (16)	−0.0157 (15)	−0.0040 (14)
N3	0.0233 (13)	0.0218 (12)	0.0287 (13)	0.0000 (11)	−0.0054 (10)	−0.0060 (10)
C9	0.0226 (16)	0.0282 (16)	0.0263 (16)	−0.0003 (13)	−0.0081 (12)	−0.0020 (12)
C7	0.0318 (19)	0.0237 (16)	0.0363 (18)	0.0033 (14)	−0.0013 (14)	0.0034 (13)
C2	0.0225 (16)	0.0204 (14)	0.0290 (16)	−0.0036 (13)	−0.0009 (12)	0.0045 (12)
C1	0.0238 (17)	0.0265 (16)	0.0233 (17)	−0.0003 (13)	−0.0030 (12)	0.0014 (12)
C10	0.0280 (17)	0.0233 (16)	0.0306 (17)	−0.0018 (14)	−0.0018 (13)	0.0022 (13)
C11	0.0283 (18)	0.0278 (17)	0.0379 (19)	−0.0017 (15)	0.0027 (13)	−0.0077 (14)
C23	0.0250 (16)	0.0272 (16)	0.0251 (16)	0.0074 (13)	−0.0015 (12)	−0.0042 (12)
C22	0.0182 (16)	0.0304 (17)	0.0306 (17)	0.0022 (14)	−0.0054 (12)	−0.0053 (13)
C16	0.0182 (15)	0.0254 (15)	0.0222 (14)	0.0028 (13)	0.0022 (11)	−0.0030 (12)
C20	0.0349 (19)	0.0365 (19)	0.0350 (19)	0.0001 (16)	−0.0068 (14)	−0.0129 (15)
C21	0.0342 (19)	0.0277 (16)	0.0250 (16)	−0.0006 (15)	0.0028 (13)	−0.0023 (13)
C18	0.040 (2)	0.0244 (17)	0.052 (2)	−0.0024 (15)	0.0072 (16)	0.0085 (15)
C28	0.036 (2)	0.0358 (18)	0.0343 (19)	−0.0006 (16)	−0.0082 (15)	−0.0008 (15)
C3	0.0346 (19)	0.0252 (16)	0.0349 (19)	−0.0034 (15)	−0.0106 (14)	0.0025 (14)
C12	0.040 (2)	0.044 (2)	0.0272 (18)	−0.0072 (17)	−0.0051 (14)	−0.0056 (15)
C17	0.0362 (19)	0.0286 (17)	0.0307 (18)	0.0009 (15)	−0.0037 (14)	0.0027 (14)
C4	0.0297 (19)	0.0205 (17)	0.065 (3)	0.0014 (15)	−0.0159 (16)	0.0054 (16)
C19	0.0283 (19)	0.0235 (17)	0.062 (2)	−0.0024 (15)	0.0005 (16)	−0.0127 (16)
C6	0.045 (2)	0.0334 (19)	0.041 (2)	0.0068 (16)	0.0079 (16)	−0.0042 (15)
C5	0.035 (2)	0.0252 (17)	0.059 (2)	0.0054 (16)	0.0036 (16)	−0.0030 (16)
C24	0.0262 (18)	0.054 (2)	0.0368 (19)	0.0058 (18)	−0.0042 (14)	−0.0013 (16)
C25	0.037 (2)	0.085 (3)	0.038 (2)	0.017 (2)	−0.0050 (16)	0.0198 (19)
C27	0.041 (2)	0.038 (2)	0.050 (2)	−0.0002 (18)	0.0034 (17)	0.0063 (16)
C26	0.045 (2)	0.048 (2)	0.055 (2)	0.0153 (19)	0.0089 (18)	0.0242 (18)
C13	0.059 (2)	0.040 (2)	0.0340 (19)	0.0021 (18)	−0.0159 (16)	0.0016 (15)

Geometric parameters (Å, º)

P3—N3	1.563 (2)	C7—C2	1.385 (4)
P3—N2	1.565 (2)	C2—C3	1.391 (4)
P3—Cl3	2.0000 (11)	C2—C1	1.508 (4)
P3—Cl4	2.0044 (10)	C10—C11	1.388 (4)
P2—N1	1.584 (2)	C11—C12	1.371 (4)
P2—N2	1.588 (2)	C23—C24	1.383 (4)
P2—N5	1.624 (2)	C23—C28	1.385 (4)
P2—Cl2	2.0400 (11)	C23—C22	1.509 (4)
Cl1—P1	2.0430 (10)	C16—C21	1.384 (4)
P1—N1	1.579 (2)	C16—C17	1.391 (4)
P1—N3	1.600 (2)	C20—C19	1.380 (4)
P1—N4	1.622 (2)	C20—C21	1.387 (4)
N5—C22	1.471 (3)	C18—C19	1.369 (4)
N5—C15	1.482 (3)	C18—C17	1.378 (4)
N4—C1	1.476 (3)	C28—C27	1.379 (4)
N4—C8	1.481 (3)	C3—C4	1.378 (4)
C8—C9	1.512 (4)	C12—C13	1.372 (4)
C15—C16	1.498 (4)	C4—C5	1.360 (4)
C14—C13	1.381 (4)	C6—C5	1.383 (5)
C14—C9	1.384 (4)	C24—C25	1.382 (5)
C9—C10	1.380 (4)	C25—C26	1.374 (5)
C7—C6	1.379 (4)	C27—C26	1.381 (5)
N3—P3—N2	119.52 (12)	C14—C9—C8	121.0 (3)
N3—P3—Cl3	107.35 (9)	C6—C7—C2	121.1 (3)
N2—P3—Cl3	109.19 (11)	C7—C2—C3	118.1 (3)
N3—P3—Cl4	109.21 (9)	C7—C2—C1	120.7 (2)
N2—P3—Cl4	109.06 (10)	C3—C2—C1	121.2 (3)
Cl3—P3—Cl4	100.89 (4)	N4—C1—C2	113.8 (2)
N1—P2—N2	118.28 (12)	C9—C10—C11	120.3 (3)
N1—P2—N5	111.06 (11)	C12—C11—C10	120.3 (3)
N2—P2—N5	108.91 (12)	C24—C23—C28	118.6 (3)
N1—P2—Cl2	106.72 (9)	C24—C23—C22	120.4 (3)
N2—P2—Cl2	105.16 (10)	C28—C23—C22	120.9 (2)
N5—P2—Cl2	105.83 (9)	N5—C22—C23	113.0 (2)
N1—P1—N3	118.22 (12)	C21—C16—C17	117.9 (3)
N1—P1—N4	110.89 (12)	C21—C16—C15	121.4 (2)
N3—P1—N4	110.49 (11)	C17—C16—C15	120.6 (2)
N1—P1—Cl1	106.97 (9)	C19—C20—C21	119.9 (3)
N3—P1—Cl1	103.41 (9)	C16—C21—C20	121.0 (3)
N4—P1—Cl1	105.81 (9)	C19—C18—C17	120.2 (3)
C22—N5—C15	115.9 (2)	C27—C28—C23	121.0 (3)
C22—N5—P2	117.67 (18)	C4—C3—C2	120.4 (3)
C15—N5—P2	123.84 (18)	C11—C12—C13	119.8 (3)
P1—N1—P2	121.37 (14)	C18—C17—C16	121.2 (3)
C1—N4—C8	116.1 (2)	C5—C4—C3	121.1 (3)
C1—N4—P1	123.28 (18)	C18—C19—C20	119.8 (3)
C8—N4—P1	118.60 (18)	C7—C6—C5	120.0 (3)
P3—N2—P2	120.82 (15)	C4—C5—C6	119.3 (3)
N4—C8—C9	113.1 (2)	C25—C24—C23	120.3 (3)
N5—C15—C16	112.9 (2)	C26—C25—C24	120.8 (3)
C13—C14—C9	120.8 (3)	C28—C27—C26	120.0 (4)
P3—N3—P1	119.98 (14)	C25—C26—C27	119.3 (3)
C10—C9—C14	118.7 (3)	C12—C13—C14	120.1 (3)
C10—C9—C8	120.3 (2)

(5)

Crystal data

C26H24Cl3N4P3	F(000) = 608
Mr = 591.75	Dx = 1.434 Mg m^−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
a = 11.657 (2) Å	Cell parameters from 10134 reflections
b = 8.5838 (17) Å	θ = 2.5–27.5°
c = 13.783 (3) Å	µ = 0.53 mm^−1
β = 96.41 (3)°	T = 150 K
V = 1370.5 (5) Å^3	Block, colourless
Z = 2	0.2 × 0.1 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer	4508 independent reflections
Radiation source: Nonius FR591 rotating anode	3152 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.101
Detector resolution: 9.091 pixels mm^-1	θmax = 24.7°, θmin = 3.0°
φ and ω scans	h = −13→13
Absorption correction: multi-scans SORTAV (Blessing, 1997)	k = −10→10
Tmin = 0.901, Tmax = 0.974	l = −16→16
13855 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.046	w = 1/[σ^2(Fo^2) + (0.P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.081	(Δ/σ)max = 0.003
S = 0.98	Δρmax = 0.23 e Å^−3
4508 reflections	Δρmin = −0.28 e Å^−3
414 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0037 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.04 (7)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
H15	0.359 (4)	−0.187 (5)	0.616 (3)	0.032 (14)*
H22	0.426 (3)	−0.124 (4)	1.037 (3)	0.013 (11)*
H12	0.691 (4)	−0.123 (5)	0.323 (4)	0.042 (15)*
H16	0.168 (4)	−0.083 (5)	0.579 (4)	0.044 (16)*
H17	0.047 (4)	−0.101 (5)	0.688 (3)	0.039 (15)*
H24	0.631 (4)	−0.454 (5)	1.202 (4)	0.041 (14)*
H2	0.581 (4)	−0.478 (5)	0.424 (3)	0.030 (13)*
H3	0.427 (4)	−0.617 (6)	0.328 (3)	0.049 (17)*
H6	0.380 (4)	−0.090 (6)	0.413 (4)	0.062 (19)*
H25	0.730 (5)	−0.476 (7)	1.075 (4)	0.08 (2)*
H4	0.258 (4)	−0.485 (5)	0.278 (4)	0.047 (15)*
H26	0.687 (4)	−0.360 (5)	0.932 (3)	0.030 (14)*
H19	0.277 (4)	−0.334 (5)	0.864 (4)	0.033 (16)*
H20B	0.589 (3)	−0.049 (4)	0.879 (3)	0.003 (10)*
H5	0.236 (4)	−0.223 (5)	0.332 (3)	0.030 (13)*
H10	1.013 (4)	−0.302 (6)	0.355 (4)	0.042 (16)*
H8	0.821 (4)	−0.337 (5)	0.582 (3)	0.034 (14)*
H18	0.102 (5)	−0.223 (7)	0.830 (4)	0.05 (2)*
H20A	0.447 (5)	−0.068 (6)	0.869 (4)	0.080 (19)*
H11	0.862 (4)	−0.187 (6)	0.262 (4)	0.044 (18)*
H9	0.976 (5)	−0.392 (6)	0.516 (4)	0.059 (18)*
H23	0.464 (5)	−0.257 (7)	1.175 (4)	0.07 (2)*
P1	0.57217 (11)	0.11239 (15)	0.58350 (10)	0.0303 (3)
P3	0.61440 (11)	−0.13660 (15)	0.70658 (9)	0.0302 (3)
Cl3	0.78045 (10)	−0.12956 (16)	0.77332 (10)	0.0432 (4)
Cl2	0.42429 (11)	0.23133 (17)	0.56084 (10)	0.0508 (4)
P2	0.60518 (10)	−0.18010 (16)	0.50623 (9)	0.0314 (3)
Cl1	0.68599 (11)	0.28886 (16)	0.58111 (10)	0.0486 (4)
C1	0.4919 (4)	−0.2769 (6)	0.4297 (4)	0.0316 (13)
N2	0.6099 (3)	−0.2476 (4)	0.6162 (3)	0.0290 (9)
N4	0.5436 (3)	−0.2153 (5)	0.7896 (3)	0.0316 (10)
C21	0.5580 (4)	−0.2267 (6)	0.9714 (3)	0.0316 (13)
C2	0.5042 (5)	−0.4301 (7)	0.4038 (4)	0.0395 (14)
C14	0.3353 (5)	−0.2690 (6)	0.7437 (4)	0.0377 (14)
N3	0.5819 (3)	0.0430 (4)	0.6900 (3)	0.0295 (10)
C20	0.5334 (5)	−0.1280 (7)	0.8804 (4)	0.0362 (14)
C19	0.2560 (6)	−0.2766 (8)	0.8112 (5)	0.0524 (18)
C5	0.3032 (5)	−0.2755 (8)	0.3435 (4)	0.0488 (17)
N1	0.5826 (3)	0.0043 (5)	0.4944 (3)	0.0329 (10)
C25	0.6703 (6)	−0.4159 (8)	1.0683 (5)	0.0501 (17)
C6	0.3896 (4)	−0.1991 (7)	0.3988 (4)	0.0423 (15)
C9	0.9312 (5)	−0.3254 (8)	0.4748 (6)	0.059 (2)
C13	0.4560 (4)	−0.3367 (6)	0.7653 (4)	0.0408 (14)
H13A	0.4572	−0.4091	0.8194	0.049*
H13B	0.4751	−0.3943	0.7087	0.049*
C15	0.3014 (6)	−0.1964 (8)	0.6547 (5)	0.0523 (18)
C7	0.7376 (4)	−0.2255 (6)	0.4583 (4)	0.0334 (13)
C11	0.8546 (6)	−0.2136 (7)	0.3251 (6)	0.0495 (17)
C3	0.4159 (5)	−0.5067 (8)	0.3466 (4)	0.0490 (16)
C18	0.1487 (6)	−0.2128 (8)	0.7920 (6)	0.0533 (18)
C12	0.7514 (5)	−0.1876 (7)	0.3627 (4)	0.0424 (15)
C26	0.6464 (5)	−0.3325 (7)	0.9825 (5)	0.0414 (15)
C24	0.6065 (6)	−0.3891 (8)	1.1446 (5)	0.0573 (18)
C8	0.8263 (5)	−0.2979 (7)	0.5150 (5)	0.0498 (17)
C22	0.4913 (5)	−0.2006 (8)	1.0476 (4)	0.0493 (17)
C4	0.3156 (5)	−0.4279 (7)	0.3185 (4)	0.0444 (15)
C16	0.1942 (6)	−0.1319 (9)	0.6352 (6)	0.0601 (19)
C23	0.5185 (7)	−0.2873 (8)	1.1339 (5)	0.0548 (18)
C10	0.9430 (6)	−0.2823 (8)	0.3835 (6)	0.055 (2)
C17	0.1185 (6)	−0.1436 (7)	0.7050 (6)	0.0570 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0307 (7)	0.0325 (9)	0.0276 (8)	0.0047 (6)	0.0035 (6)	0.0051 (7)
P3	0.0336 (7)	0.0353 (8)	0.0213 (8)	0.0014 (6)	0.0006 (6)	0.0047 (7)
Cl3	0.0382 (8)	0.0476 (9)	0.0419 (9)	0.0024 (6)	−0.0044 (7)	0.0055 (7)
Cl2	0.0483 (9)	0.0619 (11)	0.0433 (10)	0.0256 (7)	0.0096 (7)	0.0125 (8)
P2	0.0337 (8)	0.0365 (9)	0.0239 (8)	0.0025 (6)	0.0029 (6)	0.0021 (7)
Cl1	0.0581 (9)	0.0473 (9)	0.0399 (9)	−0.0149 (7)	0.0030 (7)	0.0063 (7)
C1	0.028 (3)	0.041 (4)	0.026 (3)	−0.002 (2)	0.001 (2)	0.001 (3)
N2	0.035 (2)	0.027 (2)	0.024 (2)	0.0032 (18)	0.0003 (17)	0.0051 (19)
N4	0.044 (3)	0.030 (3)	0.023 (3)	−0.0078 (19)	0.011 (2)	−0.002 (2)
C21	0.037 (3)	0.039 (4)	0.019 (3)	−0.004 (2)	0.001 (2)	0.005 (2)
C2	0.038 (3)	0.035 (4)	0.043 (4)	−0.002 (3)	−0.006 (3)	0.005 (3)
C14	0.037 (3)	0.038 (3)	0.036 (4)	−0.005 (3)	0.000 (3)	0.002 (3)
N3	0.044 (3)	0.026 (2)	0.019 (2)	0.0055 (18)	0.0048 (19)	0.0044 (19)
C20	0.041 (3)	0.038 (4)	0.029 (3)	−0.007 (3)	0.002 (3)	0.001 (3)
C19	0.054 (4)	0.059 (5)	0.044 (5)	−0.013 (3)	0.006 (4)	0.001 (4)
C5	0.028 (3)	0.067 (5)	0.052 (4)	0.003 (3)	0.002 (3)	0.003 (4)
N1	0.047 (3)	0.035 (3)	0.017 (2)	0.004 (2)	0.0050 (19)	0.003 (2)
C25	0.046 (4)	0.054 (5)	0.047 (5)	−0.011 (3)	−0.010 (3)	0.015 (4)
C6	0.043 (4)	0.046 (4)	0.038 (4)	0.011 (3)	0.002 (3)	−0.004 (3)
C9	0.052 (5)	0.064 (5)	0.061 (5)	0.018 (3)	0.004 (4)	−0.001 (4)
C13	0.054 (4)	0.042 (4)	0.027 (3)	−0.011 (3)	0.007 (3)	0.005 (3)
C15	0.048 (4)	0.076 (5)	0.036 (4)	−0.008 (3)	0.015 (3)	0.013 (3)
C7	0.041 (3)	0.032 (3)	0.028 (3)	−0.012 (2)	0.004 (3)	−0.001 (3)
C11	0.053 (4)	0.047 (4)	0.054 (5)	−0.007 (3)	0.028 (4)	−0.003 (4)
C3	0.052 (4)	0.044 (4)	0.048 (4)	−0.005 (3)	−0.007 (3)	0.004 (3)
C18	0.047 (4)	0.077 (5)	0.038 (5)	−0.013 (4)	0.015 (4)	−0.011 (4)
C12	0.053 (4)	0.041 (4)	0.033 (4)	0.001 (3)	0.007 (3)	−0.001 (3)
C26	0.037 (3)	0.054 (4)	0.034 (4)	−0.005 (3)	0.006 (3)	0.007 (3)
C24	0.070 (5)	0.068 (5)	0.032 (4)	−0.015 (4)	−0.004 (4)	0.017 (4)
C8	0.049 (4)	0.061 (4)	0.040 (4)	0.016 (3)	0.006 (3)	0.000 (4)
C22	0.047 (4)	0.070 (5)	0.033 (4)	−0.002 (3)	0.012 (3)	0.003 (4)
C4	0.042 (4)	0.047 (4)	0.043 (4)	−0.014 (3)	0.000 (3)	0.003 (3)
C16	0.042 (4)	0.089 (6)	0.048 (4)	0.001 (4)	−0.003 (3)	0.021 (4)
C23	0.073 (5)	0.063 (5)	0.033 (4)	−0.011 (4)	0.022 (4)	0.005 (4)
C10	0.040 (4)	0.049 (4)	0.082 (6)	−0.011 (3)	0.034 (4)	−0.026 (4)
C17	0.039 (4)	0.061 (4)	0.071 (5)	0.001 (3)	0.004 (4)	−0.015 (4)

Geometric parameters (Å, º)

P1—N1	1.555 (4)	C14—C19	1.385 (8)
P1—N3	1.577 (4)	C14—C15	1.394 (8)
P1—Cl2	1.9978 (18)	C14—C13	1.520 (7)
P1—Cl1	2.0164 (19)	C19—C18	1.364 (9)
P3—N2	1.564 (4)	C5—C6	1.361 (7)
P3—N3	1.598 (4)	C5—C4	1.365 (8)
P3—N4	1.630 (4)	C25—C24	1.374 (9)
P3—Cl3	2.0491 (17)	C25—C26	1.384 (8)
P2—N1	1.610 (4)	C9—C10	1.334 (9)
P2—N2	1.618 (4)	C9—C8	1.418 (8)
P2—C7	1.789 (5)	C15—C16	1.366 (8)
P2—C1	1.799 (5)	C7—C8	1.373 (7)
C1—C2	1.375 (7)	C7—C12	1.385 (7)
C1—C6	1.391 (6)	C11—C10	1.368 (9)
N4—C13	1.472 (6)	C11—C12	1.381 (8)
N4—C20	1.476 (6)	C3—C4	1.369 (7)
C21—C26	1.369 (7)	C18—C17	1.348 (10)
C21—C22	1.393 (7)	C24—C23	1.343 (9)
C21—C20	1.514 (7)	C22—C23	1.409 (8)
C2—C3	1.390 (7)	C16—C17	1.380 (9)
N1—P1—N3	120.4 (2)	C19—C14—C15	117.9 (6)
N1—P1—Cl2	108.90 (16)	C19—C14—C13	121.6 (5)
N3—P1—Cl2	108.05 (16)	C15—C14—C13	120.5 (5)
N1—P1—Cl1	108.99 (17)	P1—N3—P3	119.3 (2)
N3—P1—Cl1	108.66 (16)	N4—C20—C21	113.1 (4)
Cl2—P1—Cl1	99.87 (8)	C18—C19—C14	121.1 (7)
N2—P3—N3	119.2 (2)	C6—C5—C4	120.7 (6)
N2—P3—N4	109.4 (2)	P1—N1—P2	122.2 (2)
N3—P3—N4	111.7 (2)	C24—C25—C26	119.6 (7)
N2—P3—Cl3	108.75 (16)	C5—C6—C1	119.7 (6)
N3—P3—Cl3	103.45 (15)	C10—C9—C8	120.5 (6)
N4—P3—Cl3	102.94 (15)	N4—C13—C14	112.2 (4)
N1—P2—N2	115.8 (2)	C16—C15—C14	121.1 (6)
N1—P2—C7	108.3 (2)	C8—C7—C12	119.2 (5)
N2—P2—C7	109.1 (2)	C8—C7—P2	121.0 (4)
N1—P2—C1	107.1 (2)	C12—C7—P2	119.8 (4)
N2—P2—C1	109.3 (2)	C10—C11—C12	118.7 (7)
C7—P2—C1	106.9 (2)	C4—C3—C2	118.8 (6)
C2—C1—C6	119.4 (5)	C17—C18—C19	119.5 (7)
C2—C1—P2	120.2 (4)	C11—C12—C7	121.2 (6)
C6—C1—P2	120.4 (4)	C21—C26—C25	121.0 (6)
P3—N2—P2	121.5 (2)	C23—C24—C25	119.7 (6)
C13—N4—C20	115.7 (4)	C7—C8—C9	118.7 (6)
C13—N4—P3	121.8 (3)	C21—C22—C23	117.4 (6)
C20—N4—P3	118.7 (3)	C5—C4—C3	120.9 (6)
C26—C21—C22	119.9 (5)	C15—C16—C17	118.4 (7)
C26—C21—C20	122.3 (5)	C24—C23—C22	122.3 (7)
C22—C21—C20	117.7 (5)	C9—C10—C11	121.6 (6)
C1—C2—C3	120.5 (5)	C18—C17—C16	121.9 (7)

(6)

Crystal data

C40H38Cl2N5P3	F(000) = 1568
Mr = 752.56	Dx = 1.348 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.2810 (1) Å	Cell parameters from 44308 reflections
b = 21.0219 (3) Å	θ = 2.9–27.5°
c = 17.3783 (2) Å	µ = 0.34 mm^−1
β = 99.047 (1)°	T = 120 K
V = 3709.18 (8) Å^3	Block, colourless
Z = 4	0.40 × 0.20 × 0.18 mm

Data collection

Nonius KappaCCD diffractometer	8451 independent reflections
Radiation source: Nonius FR591 rotating anode	7150 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
φ and ω scans	h = −13→13
Absorption correction: multi-scan SORTAV (Blessing, 1997)	k = −27→27
Tmin = 0.876, Tmax = 0.941	l = −22→20
42554 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0429P)^2 + 2.220P] where P = (Fo^2 + 2Fc^2)/3
8451 reflections	(Δ/σ)max = 0.003
452 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.41 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.00712 (15)	−0.14389 (7)	0.22105 (9)	0.0191 (3)
H1A	0.0860	−0.1395	0.2137	0.023*
H1B	−0.0603	−0.1503	0.1690	0.023*
C2	−0.01985 (15)	−0.20242 (7)	0.27018 (9)	0.0191 (3)
C3	−0.10711 (16)	−0.25074 (7)	0.24257 (9)	0.0227 (3)
H3	−0.1614	−0.2464	0.1933	0.027*
C4	−0.11567 (17)	−0.30556 (8)	0.28656 (10)	0.0271 (4)
H4	−0.1767	−0.3380	0.2676	0.033*
C5	−0.03554 (18)	−0.31280 (8)	0.35779 (10)	0.0289 (4)
H5	−0.0405	−0.3504	0.3875	0.035*
C6	0.05222 (17)	−0.26478 (8)	0.38565 (10)	0.0292 (4)
H6	0.1074	−0.2696	0.4345	0.035*
C7	0.05952 (16)	−0.20971 (8)	0.34220 (9)	0.0249 (3)
H7	0.1191	−0.1769	0.3618	0.030*
C8	−0.19179 (14)	−0.07589 (7)	0.25165 (9)	0.0195 (3)
H8A	−0.2077	−0.0373	0.2815	0.023*
H8B	−0.2277	−0.1129	0.2767	0.023*
C9	−0.26240 (14)	−0.06948 (7)	0.16896 (9)	0.0191 (3)
C10	−0.33372 (15)	−0.12012 (8)	0.13225 (9)	0.0235 (3)
H10	−0.3424	−0.1583	0.1603	0.028*
C11	−0.39248 (17)	−0.11539 (8)	0.05474 (10)	0.0272 (4)
H11	−0.4406	−0.1504	0.0301	0.033*
C12	−0.38116 (17)	−0.06005 (8)	0.01342 (10)	0.0274 (4)
H12	−0.4203	−0.0571	−0.0397	0.033*
C13	−0.31224 (17)	−0.00880 (8)	0.05008 (10)	0.0289 (4)
H13	−0.3054	0.0296	0.0221	0.035*
C14	−0.25326 (16)	−0.01341 (8)	0.12733 (10)	0.0249 (3)
H14	−0.2063	0.0219	0.1520	0.030*
C15	0.44777 (15)	−0.02950 (7)	0.39572 (8)	0.0198 (3)
H15A	0.3633	−0.0487	0.4043	0.024*
H15B	0.4774	−0.0007	0.4401	0.024*
C16	0.54837 (15)	−0.08205 (7)	0.39602 (9)	0.0211 (3)
C17	0.51804 (17)	−0.13597 (8)	0.35017 (10)	0.0265 (3)
H17	0.4358	−0.1386	0.3167	0.032*
C18	0.60659 (19)	−0.18584 (8)	0.35289 (11)	0.0336 (4)
H18	0.5852	−0.2223	0.3211	0.040*
C19	0.72624 (19)	−0.18256 (9)	0.40184 (11)	0.0343 (4)
H19	0.7865	−0.2170	0.4041	0.041*
C20	0.75814 (17)	−0.12936 (9)	0.44729 (11)	0.0329 (4)
H20	0.8405	−0.1271	0.4807	0.039*
C21	0.66947 (16)	−0.07876 (8)	0.44420 (10)	0.0252 (3)
H21	0.6921	−0.0420	0.4752	0.030*
C22	0.53422 (15)	0.04842 (7)	0.30831 (9)	0.0214 (3)
H22A	0.5102	0.0694	0.2570	0.026*
H22B	0.6119	0.0211	0.3058	0.026*
C23	0.57005 (16)	0.09872 (7)	0.37030 (9)	0.0228 (3)
C24	0.69858 (17)	0.10414 (9)	0.40912 (10)	0.0310 (4)
H24	0.7643	0.0755	0.3976	0.037*
C25	0.7311 (2)	0.15155 (10)	0.46493 (11)	0.0416 (5)
H25	0.8190	0.1551	0.4913	0.050*
C26	0.6359 (2)	0.19330 (10)	0.48197 (11)	0.0419 (5)
H26	0.6585	0.2256	0.5199	0.050*
C27	0.5078 (2)	0.18804 (9)	0.44386 (11)	0.0362 (4)
H27	0.4423	0.2167	0.4557	0.043*
C28	0.47482 (17)	0.14083 (8)	0.38825 (10)	0.0287 (4)
H28	0.3866	0.1373	0.3623	0.034*
C29	0.09967 (14)	0.16154 (7)	0.27603 (9)	0.0186 (3)
C30	0.17894 (17)	0.21138 (8)	0.25771 (10)	0.0282 (4)
H30	0.2302	0.2065	0.2171	0.034*
C31	0.18280 (17)	0.26799 (8)	0.29888 (11)	0.0314 (4)
H31	0.2365	0.3020	0.2862	0.038*
C32	0.10922 (17)	0.27531 (8)	0.35822 (10)	0.0297 (4)
H32	0.1131	0.3140	0.3867	0.036*
C33	0.0299 (2)	0.22626 (9)	0.37616 (11)	0.0371 (4)
H33	−0.0216	0.2314	0.4166	0.045*
C34	0.02525 (19)	0.16920 (8)	0.33517 (10)	0.0305 (4)
H34	−0.0291	0.1355	0.3478	0.037*
C35	0.02153 (15)	0.10657 (7)	0.12463 (9)	0.0198 (3)
C36	0.07247 (18)	0.08092 (9)	0.06209 (10)	0.0323 (4)
H36	0.1501	0.0557	0.0711	0.039*
C37	0.0103 (2)	0.09202 (10)	−0.01363 (10)	0.0391 (5)
H37	0.0452	0.0744	−0.0564	0.047*
C38	−0.10266 (18)	0.12875 (8)	−0.02666 (10)	0.0301 (4)
H38	−0.1451	0.1363	−0.0785	0.036*
C39	−0.15385 (17)	0.15444 (8)	0.03507 (10)	0.0269 (4)
H39	−0.2312	0.1798	0.0258	0.032*
C40	−0.09260 (16)	0.14330 (7)	0.11082 (9)	0.0226 (3)
H40	−0.1285	0.1607	0.1534	0.027*
N1	0.19795 (12)	−0.04997 (6)	0.28457 (8)	0.0218 (3)
N2	0.24427 (12)	0.06497 (6)	0.22042 (8)	0.0212 (3)
N3	0.00312 (12)	0.03960 (6)	0.26023 (8)	0.0190 (3)
N4	−0.04894 (12)	−0.08440 (6)	0.25395 (7)	0.0179 (3)
N5	0.42421 (12)	0.00855 (6)	0.32370 (7)	0.0184 (3)
P1	0.05187 (4)	−0.028442 (18)	0.29051 (2)	0.01710 (9)
P2	0.29749 (4)	−0.001002 (17)	0.25573 (2)	0.01653 (9)
P3	0.09649 (4)	0.087992 (18)	0.22286 (2)	0.01683 (9)
Cl1	0.03584 (4)	−0.02720 (2)	0.40717 (2)	0.02988 (11)
Cl2	0.37236 (4)	−0.045214 (19)	0.16692 (2)	0.02718 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0213 (7)	0.0183 (7)	0.0182 (7)	0.0016 (6)	0.0042 (6)	0.0002 (6)
C2	0.0205 (7)	0.0178 (7)	0.0199 (7)	0.0038 (6)	0.0060 (6)	−0.0002 (6)
C3	0.0263 (8)	0.0204 (7)	0.0213 (8)	0.0019 (6)	0.0035 (6)	−0.0034 (6)
C4	0.0332 (9)	0.0181 (8)	0.0315 (9)	−0.0031 (6)	0.0096 (7)	−0.0047 (6)
C5	0.0372 (10)	0.0191 (8)	0.0321 (9)	0.0042 (7)	0.0104 (7)	0.0050 (7)
C6	0.0312 (9)	0.0291 (9)	0.0255 (9)	0.0042 (7)	−0.0009 (7)	0.0075 (7)
C7	0.0258 (8)	0.0236 (8)	0.0245 (8)	−0.0016 (6)	0.0013 (6)	0.0015 (6)
C8	0.0159 (7)	0.0214 (7)	0.0215 (7)	−0.0010 (6)	0.0044 (6)	0.0003 (6)
C9	0.0140 (7)	0.0215 (7)	0.0220 (7)	0.0022 (6)	0.0039 (6)	0.0005 (6)
C10	0.0235 (8)	0.0209 (8)	0.0262 (8)	−0.0003 (6)	0.0043 (6)	0.0008 (6)
C11	0.0264 (8)	0.0255 (8)	0.0286 (9)	−0.0024 (7)	0.0014 (7)	−0.0056 (7)
C12	0.0251 (8)	0.0336 (9)	0.0220 (8)	0.0026 (7)	−0.0006 (6)	0.0013 (7)
C13	0.0268 (9)	0.0279 (9)	0.0306 (9)	−0.0005 (7)	0.0003 (7)	0.0094 (7)
C14	0.0205 (8)	0.0241 (8)	0.0289 (9)	−0.0022 (6)	0.0004 (6)	0.0024 (6)
C15	0.0206 (7)	0.0244 (8)	0.0137 (7)	0.0014 (6)	0.0009 (6)	0.0032 (6)
C16	0.0222 (8)	0.0225 (8)	0.0192 (7)	0.0006 (6)	0.0048 (6)	0.0067 (6)
C17	0.0301 (9)	0.0228 (8)	0.0268 (8)	−0.0008 (7)	0.0048 (7)	0.0034 (6)
C18	0.0434 (11)	0.0212 (8)	0.0387 (10)	0.0033 (7)	0.0146 (8)	0.0046 (7)
C19	0.0362 (10)	0.0270 (9)	0.0443 (11)	0.0128 (7)	0.0208 (8)	0.0170 (8)
C20	0.0220 (8)	0.0432 (11)	0.0342 (10)	0.0067 (7)	0.0071 (7)	0.0167 (8)
C21	0.0226 (8)	0.0291 (9)	0.0238 (8)	0.0003 (6)	0.0035 (6)	0.0060 (6)
C22	0.0171 (7)	0.0244 (8)	0.0226 (8)	−0.0036 (6)	0.0034 (6)	0.0011 (6)
C23	0.0234 (8)	0.0236 (8)	0.0209 (8)	−0.0056 (6)	0.0017 (6)	0.0026 (6)
C24	0.0251 (9)	0.0357 (10)	0.0306 (9)	−0.0072 (7)	−0.0006 (7)	0.0035 (7)
C25	0.0366 (11)	0.0516 (12)	0.0329 (10)	−0.0200 (9)	−0.0062 (8)	−0.0009 (9)
C26	0.0542 (13)	0.0430 (11)	0.0290 (10)	−0.0230 (10)	0.0085 (9)	−0.0100 (8)
C27	0.0448 (11)	0.0315 (10)	0.0357 (10)	−0.0082 (8)	0.0163 (8)	−0.0071 (8)
C28	0.0257 (8)	0.0297 (9)	0.0306 (9)	−0.0036 (7)	0.0043 (7)	−0.0018 (7)
C29	0.0182 (7)	0.0166 (7)	0.0198 (7)	0.0009 (5)	−0.0011 (6)	0.0031 (5)
C30	0.0255 (8)	0.0247 (8)	0.0354 (9)	−0.0050 (7)	0.0077 (7)	−0.0003 (7)
C31	0.0268 (9)	0.0226 (8)	0.0438 (10)	−0.0082 (7)	0.0025 (7)	−0.0010 (7)
C32	0.0329 (9)	0.0198 (8)	0.0342 (9)	0.0006 (7)	−0.0020 (7)	−0.0038 (7)
C33	0.0516 (12)	0.0263 (9)	0.0374 (10)	−0.0028 (8)	0.0194 (9)	−0.0054 (8)
C34	0.0414 (10)	0.0195 (8)	0.0335 (9)	−0.0052 (7)	0.0148 (8)	−0.0009 (7)
C35	0.0204 (7)	0.0180 (7)	0.0208 (7)	0.0007 (6)	0.0027 (6)	0.0028 (6)
C36	0.0341 (10)	0.0391 (10)	0.0248 (9)	0.0171 (8)	0.0082 (7)	0.0067 (7)
C37	0.0468 (12)	0.0506 (12)	0.0217 (9)	0.0202 (9)	0.0104 (8)	0.0036 (8)
C38	0.0353 (10)	0.0335 (9)	0.0202 (8)	0.0062 (7)	0.0006 (7)	0.0051 (7)
C39	0.0265 (8)	0.0256 (8)	0.0269 (8)	0.0077 (7)	−0.0008 (7)	0.0029 (6)
C40	0.0245 (8)	0.0205 (7)	0.0225 (8)	0.0048 (6)	0.0031 (6)	−0.0016 (6)
N1	0.0169 (6)	0.0184 (6)	0.0290 (7)	−0.0001 (5)	0.0008 (5)	0.0066 (5)
N2	0.0172 (6)	0.0192 (6)	0.0276 (7)	0.0010 (5)	0.0050 (5)	0.0076 (5)
N3	0.0173 (6)	0.0160 (6)	0.0241 (7)	0.0004 (5)	0.0042 (5)	0.0024 (5)
N4	0.0156 (6)	0.0155 (6)	0.0224 (6)	−0.0002 (5)	0.0027 (5)	−0.0002 (5)
N5	0.0172 (6)	0.0211 (6)	0.0163 (6)	−0.0027 (5)	0.0004 (5)	0.0026 (5)
P1	0.01641 (19)	0.01680 (19)	0.01758 (19)	−0.00150 (14)	0.00110 (14)	0.00283 (14)
P2	0.01503 (18)	0.01626 (19)	0.01770 (19)	0.00059 (14)	0.00073 (14)	0.00223 (14)
P3	0.01616 (19)	0.01541 (18)	0.01867 (19)	0.00057 (14)	0.00196 (14)	0.00296 (14)
Cl1	0.0370 (2)	0.0355 (2)	0.01660 (19)	−0.00612 (18)	0.00264 (16)	0.00114 (15)
Cl2	0.0337 (2)	0.0270 (2)	0.02107 (19)	0.00300 (16)	0.00505 (16)	−0.00487 (15)

Geometric parameters (Å, º)

C1—N4	1.4674 (18)	C22—H22A	0.9900
C1—C2	1.515 (2)	C22—H22B	0.9900
C1—H1A	0.9900	C23—C28	1.391 (2)
C1—H1B	0.9900	C23—C24	1.391 (2)
C2—C3	1.390 (2)	C24—C25	1.394 (3)
C2—C7	1.391 (2)	C24—H24	0.9500
C3—C4	1.393 (2)	C25—C26	1.381 (3)
C3—H3	0.9500	C25—H25	0.9500
C4—C5	1.383 (2)	C26—C27	1.383 (3)
C4—H4	0.9500	C26—H26	0.9500
C5—C6	1.389 (2)	C27—C28	1.389 (2)
C5—H5	0.9500	C27—H27	0.9500
C6—C7	1.390 (2)	C28—H28	0.9500
C6—H6	0.9500	C29—C34	1.384 (2)
C7—H7	0.9500	C29—C30	1.395 (2)
C8—N4	1.4738 (19)	C29—P3	1.7989 (15)
C8—C9	1.511 (2)	C30—C31	1.386 (2)
C8—H8A	0.9900	C30—H30	0.9500
C8—H8B	0.9900	C31—C32	1.380 (3)
C9—C10	1.390 (2)	C31—H31	0.9500
C9—C14	1.394 (2)	C32—C33	1.380 (3)
C10—C11	1.390 (2)	C32—H32	0.9500
C10—H10	0.9500	C33—C34	1.392 (2)
C11—C12	1.382 (2)	C33—H33	0.9500
C11—H11	0.9500	C34—H34	0.9500
C12—C13	1.388 (2)	C35—C36	1.388 (2)
C12—H12	0.9500	C35—C40	1.394 (2)
C13—C14	1.387 (2)	C35—P3	1.8017 (15)
C13—H13	0.9500	C36—C37	1.389 (2)
C14—H14	0.9500	C36—H36	0.9500
C15—N5	1.4729 (18)	C37—C38	1.383 (2)
C15—C16	1.513 (2)	C37—H37	0.9500
C15—H15A	0.9900	C38—C39	1.377 (2)
C15—H15B	0.9900	C38—H38	0.9500
C16—C21	1.389 (2)	C39—C40	1.387 (2)
C16—C17	1.392 (2)	C39—H39	0.9500
C17—C18	1.384 (2)	C40—H40	0.9500
C17—H17	0.9500	N1—P2	1.5873 (13)
C18—C19	1.383 (3)	N1—P1	1.5875 (13)
C18—H18	0.9500	N2—P2	1.5791 (13)
C19—C20	1.379 (3)	N2—P3	1.6015 (13)
C19—H19	0.9500	N3—P1	1.5784 (13)
C20—C21	1.396 (2)	N3—P3	1.6044 (13)
C20—H20	0.9500	N4—P1	1.6292 (13)
C21—H21	0.9500	N5—P2	1.6276 (12)
C22—N5	1.4657 (19)	P1—Cl1	2.0599 (5)
C22—C23	1.513 (2)	P2—Cl2	2.0522 (5)
N4—C1—C2	114.59 (12)	C24—C23—C22	120.60 (15)
N4—C1—H1A	108.6	C23—C24—C25	120.10 (18)
C2—C1—H1A	108.6	C23—C24—H24	119.9
N4—C1—H1B	108.6	C25—C24—H24	119.9
C2—C1—H1B	108.6	C26—C25—C24	120.21 (18)
H1A—C1—H1B	107.6	C26—C25—H25	119.9
C3—C2—C7	119.06 (14)	C24—C25—H25	119.9
C3—C2—C1	120.48 (14)	C25—C26—C27	120.02 (18)
C7—C2—C1	120.41 (14)	C25—C26—H26	120.0
C2—C3—C4	120.54 (15)	C27—C26—H26	120.0
C2—C3—H3	119.7	C26—C27—C28	120.00 (19)
C4—C3—H3	119.7	C26—C27—H27	120.0
C5—C4—C3	120.12 (15)	C28—C27—H27	120.0
C5—C4—H4	119.9	C27—C28—C23	120.47 (17)
C3—C4—H4	119.9	C27—C28—H28	119.8
C4—C5—C6	119.65 (15)	C23—C28—H28	119.8
C4—C5—H5	120.2	C34—C29—C30	119.56 (15)
C6—C5—H5	120.2	C34—C29—P3	120.93 (12)
C5—C6—C7	120.22 (16)	C30—C29—P3	119.51 (12)
C5—C6—H6	119.9	C31—C30—C29	119.84 (16)
C7—C6—H6	119.9	C31—C30—H30	120.1
C6—C7—C2	120.41 (15)	C29—C30—H30	120.1
C6—C7—H7	119.8	C32—C31—C30	120.46 (16)
C2—C7—H7	119.8	C32—C31—H31	119.8
N4—C8—C9	111.37 (12)	C30—C31—H31	119.8
N4—C8—H8A	109.4	C33—C32—C31	119.88 (16)
C9—C8—H8A	109.4	C33—C32—H32	120.1
N4—C8—H8B	109.4	C31—C32—H32	120.1
C9—C8—H8B	109.4	C32—C33—C34	120.14 (17)
H8A—C8—H8B	108.0	C32—C33—H33	119.9
C10—C9—C14	118.90 (14)	C34—C33—H33	119.9
C10—C9—C8	120.55 (14)	C29—C34—C33	120.12 (16)
C14—C9—C8	120.51 (14)	C29—C34—H34	119.9
C9—C10—C11	120.50 (15)	C33—C34—H34	119.9
C9—C10—H10	119.7	C36—C35—C40	119.45 (14)
C11—C10—H10	119.7	C36—C35—P3	120.00 (12)
C12—C11—C10	120.29 (15)	C40—C35—P3	120.42 (12)
C12—C11—H11	119.9	C35—C36—C37	120.16 (16)
C10—C11—H11	119.9	C35—C36—H36	119.9
C11—C12—C13	119.59 (15)	C37—C36—H36	119.9
C11—C12—H12	120.2	C38—C37—C36	119.89 (17)
C13—C12—H12	120.2	C38—C37—H37	120.1
C14—C13—C12	120.26 (15)	C36—C37—H37	120.1
C14—C13—H13	119.9	C39—C38—C37	120.34 (16)
C12—C13—H13	119.9	C39—C38—H38	119.8
C13—C14—C9	120.44 (15)	C37—C38—H38	119.8
C13—C14—H14	119.8	C38—C39—C40	120.06 (15)
C9—C14—H14	119.8	C38—C39—H39	120.0
N5—C15—C16	114.86 (12)	C40—C39—H39	120.0
N5—C15—H15A	108.6	C39—C40—C35	120.09 (15)
C16—C15—H15A	108.6	C39—C40—H40	120.0
N5—C15—H15B	108.6	C35—C40—H40	120.0
C16—C15—H15B	108.6	P2—N1—P1	119.94 (8)
H15A—C15—H15B	107.5	P2—N2—P3	121.83 (8)
C21—C16—C17	118.97 (15)	P1—N3—P3	122.05 (8)
C21—C16—C15	120.89 (14)	C1—N4—C8	116.40 (12)
C17—C16—C15	120.07 (14)	C1—N4—P1	124.05 (10)
C18—C17—C16	120.66 (17)	C8—N4—P1	119.54 (10)
C18—C17—H17	119.7	C22—N5—C15	115.92 (12)
C16—C17—H17	119.7	C22—N5—P2	119.38 (10)
C17—C18—C19	119.99 (17)	C15—N5—P2	123.76 (10)
C17—C18—H18	120.0	N3—P1—N1	119.39 (7)
C19—C18—H18	120.0	N3—P1—N4	112.03 (7)
C20—C19—C18	120.09 (16)	N1—P1—N4	108.61 (7)
C20—C19—H19	120.0	N3—P1—Cl1	104.26 (5)
C18—C19—H19	120.0	N1—P1—Cl1	106.89 (5)
C19—C20—C21	120.05 (17)	N4—P1—Cl1	104.39 (5)
C19—C20—H20	120.0	N2—P2—N1	119.41 (7)
C21—C20—H20	120.0	N2—P2—N5	111.26 (7)
C16—C21—C20	120.23 (16)	N1—P2—N5	109.45 (7)
C16—C21—H21	119.9	N2—P2—Cl2	104.69 (5)
C20—C21—H21	119.9	N1—P2—Cl2	106.29 (5)
N5—C22—C23	112.22 (13)	N5—P2—Cl2	104.45 (5)
N5—C22—H22A	109.2	N2—P3—N3	116.72 (7)
C23—C22—H22A	109.2	N2—P3—C29	109.43 (7)
N5—C22—H22B	109.2	N3—P3—C29	107.50 (7)
C23—C22—H22B	109.2	N2—P3—C35	107.86 (7)
H22A—C22—H22B	107.9	N3—P3—C35	109.08 (7)
C28—C23—C24	119.18 (16)	C29—P3—C35	105.72 (7)
C28—C23—C22	120.21 (14)
N4—C1—C2—C3	115.19 (16)	C38—C39—C40—C35	0.6 (3)
N4—C1—C2—C7	−67.43 (19)	C36—C35—C40—C39	−0.5 (2)
C7—C2—C3—C4	0.4 (2)	P3—C35—C40—C39	−176.40 (13)
C1—C2—C3—C4	177.80 (14)	C2—C1—N4—C8	−72.48 (16)
C2—C3—C4—C5	−1.0 (2)	C2—C1—N4—P1	108.54 (14)
C3—C4—C5—C6	0.8 (3)	C9—C8—N4—C1	−66.69 (16)
C4—C5—C6—C7	0.0 (3)	C9—C8—N4—P1	112.34 (13)
C5—C6—C7—C2	−0.7 (3)	C23—C22—N5—C15	−62.85 (17)
C3—C2—C7—C6	0.5 (2)	C23—C22—N5—P2	127.84 (12)
C1—C2—C7—C6	−176.96 (15)	C16—C15—N5—C22	−67.50 (17)
N4—C8—C9—C10	103.41 (16)	C16—C15—N5—P2	101.28 (15)
N4—C8—C9—C14	−74.34 (18)	P3—N3—P1—N1	0.40 (13)
C14—C9—C10—C11	1.4 (2)	P3—N3—P1—N4	−128.14 (9)
C8—C9—C10—C11	−176.35 (14)	P3—N3—P1—Cl1	119.56 (8)
C9—C10—C11—C12	−0.4 (2)	P2—N1—P1—N3	5.63 (13)
C10—C11—C12—C13	−0.9 (3)	P2—N1—P1—N4	135.72 (9)
C11—C12—C13—C14	1.0 (3)	P2—N1—P1—Cl1	−112.17 (8)
C12—C13—C14—C9	0.1 (3)	C1—N4—P1—N3	133.60 (12)
C10—C9—C14—C13	−1.3 (2)	C8—N4—P1—N3	−45.35 (13)
C8—C9—C14—C13	176.50 (15)	C1—N4—P1—N1	−0.42 (14)
N5—C15—C16—C21	111.20 (16)	C8—N4—P1—N1	−179.37 (11)
N5—C15—C16—C17	−71.66 (19)	C1—N4—P1—Cl1	−114.18 (11)
C21—C16—C17—C18	0.5 (2)	C8—N4—P1—Cl1	66.87 (11)
C15—C16—C17—C18	−176.68 (15)	P3—N2—P2—N1	8.10 (14)
C16—C17—C18—C19	0.4 (3)	P3—N2—P2—N5	−120.92 (10)
C17—C18—C19—C20	−0.8 (3)	P3—N2—P2—Cl2	126.82 (8)
C18—C19—C20—C21	0.2 (3)	P1—N1—P2—N2	−9.80 (13)
C17—C16—C21—C20	−1.0 (2)	P1—N1—P2—N5	120.03 (9)
C15—C16—C21—C20	176.13 (14)	P1—N1—P2—Cl2	−127.70 (8)
C19—C20—C21—C16	0.7 (2)	C22—N5—P2—N2	−50.11 (13)
N5—C22—C23—C28	−55.11 (19)	C15—N5—P2—N2	141.48 (12)
N5—C22—C23—C24	125.92 (16)	C22—N5—P2—N1	175.77 (11)
C28—C23—C24—C25	−0.4 (3)	C15—N5—P2—N1	7.35 (14)
C22—C23—C24—C25	178.60 (16)	C22—N5—P2—Cl2	62.30 (12)
C23—C24—C25—C26	0.0 (3)	C15—N5—P2—Cl2	−106.11 (12)
C24—C25—C26—C27	0.2 (3)	P2—N2—P3—N3	−2.14 (13)
C25—C26—C27—C28	−0.2 (3)	P2—N2—P3—C29	120.17 (10)
C26—C27—C28—C23	−0.2 (3)	P2—N2—P3—C35	−125.28 (10)
C24—C23—C28—C27	0.5 (3)	P1—N3—P3—N2	−2.15 (13)
C22—C23—C28—C27	−178.53 (15)	P1—N3—P3—C29	−125.46 (9)
C34—C29—C30—C31	0.2 (2)	P1—N3—P3—C35	120.36 (9)
P3—C29—C30—C31	−179.43 (13)	C34—C29—P3—N2	−130.14 (14)
C29—C30—C31—C32	0.3 (3)	C30—C29—P3—N2	49.44 (14)
C30—C31—C32—C33	−0.8 (3)	C34—C29—P3—N3	−2.48 (15)
C31—C32—C33—C34	0.8 (3)	C30—C29—P3—N3	177.10 (12)
C30—C29—C34—C33	−0.2 (3)	C34—C29—P3—C35	113.94 (14)
P3—C29—C34—C33	179.39 (15)	C30—C29—P3—C35	−66.48 (14)
C32—C33—C34—C29	−0.3 (3)	C36—C35—P3—N2	21.31 (16)
C40—C35—C36—C37	0.2 (3)	C40—C35—P3—N2	−162.84 (12)
P3—C35—C36—C37	176.12 (16)	C36—C35—P3—N3	−106.38 (15)
C35—C36—C37—C38	0.0 (3)	C40—C35—P3—N3	69.48 (14)
C36—C37—C38—C39	0.0 (3)	C36—C35—P3—C29	138.29 (14)
C37—C38—C39—C40	−0.3 (3)	C40—C35—P3—C29	−45.86 (14)

(7)

Crystal data

C5H12Cl4N5P3	Dx = 1.693 Mg m^−3
Mr = 376.91	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 4103 reflections
a = 7.8379 (2) Å	θ = 2.9–27.5°
b = 13.4076 (3) Å	µ = 1.11 mm^−1
c = 14.0752 (4) Å	T = 150 K
V = 1479.13 (7) Å^3	Plate, colourless
Z = 4	0.30 × 0.18 × 0.05 mm
F(000) = 760

Data collection

Nonius KappaCCD diffractometer	3272 independent reflections
Radiation source: Nonius FR591 rotating anode	3093 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
φ and ω scans	h = −8→10
Absorption correction: multi-scan SORTAV (Blessing, 1997)	k = −17→14
Tmin = 0.732, Tmax = 0.947	l = −18→17
7531 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.027	w = 1/[σ^2(Fo^2) + (0.0318P)^2 + 0.6613P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.065	(Δ/σ)max = 0.015
S = 0.91	Δρmax = 0.28 e Å^−3
3272 reflections	Δρmin = −0.38 e Å^−3
157 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0068 (10)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.03 (6)

Special details

Experimental. Robert Shaw

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.0480 (4)	1.07978 (18)	0.19839 (18)	0.0298 (6)
H1A	−0.0045	1.1209	0.1488	0.045*
H1B	−0.0413	1.0449	0.2340	0.045*
H1C	0.1245	1.0309	0.1691	0.045*
C2	0.2732 (3)	1.20580 (17)	0.21410 (15)	0.0215 (5)
H2A	0.2186	1.2400	0.1597	0.026*
H2B	0.3653	1.1627	0.1890	0.026*
C3	0.3488 (3)	1.28261 (16)	0.28084 (15)	0.0202 (5)
H3A	0.2577	1.3285	0.3022	0.024*
H3B	0.4352	1.3224	0.2463	0.024*
C4	0.4313 (3)	1.23468 (16)	0.36670 (16)	0.0202 (5)
H4A	0.5239	1.1896	0.3458	0.024*
H4B	0.4819	1.2869	0.4076	0.024*
C5	0.3571 (3)	1.15555 (17)	0.51901 (15)	0.0214 (5)
H5A	0.4550	1.1101	0.5180	0.032*
H5B	0.2623	1.1241	0.5532	0.032*
H5C	0.3892	1.2176	0.5512	0.032*
N1	0.0094 (2)	1.08542 (13)	0.42615 (13)	0.0179 (4)
N2	0.0191 (3)	0.88213 (13)	0.43282 (14)	0.0215 (4)
N3	0.2834 (2)	0.98818 (13)	0.35845 (12)	0.0152 (4)
N4	0.1460 (2)	1.14394 (13)	0.26345 (13)	0.0181 (4)
N5	0.3042 (3)	1.17780 (13)	0.42114 (12)	0.0163 (4)
P1	0.18552 (7)	1.09496 (4)	0.36809 (4)	0.01315 (13)
P2	−0.07214 (7)	0.98427 (4)	0.45699 (4)	0.01813 (14)
P3	0.19750 (7)	0.88565 (4)	0.37925 (4)	0.01324 (13)
Cl1	−0.31145 (8)	0.97709 (5)	0.40795 (6)	0.03717 (18)
Cl2	−0.11503 (10)	0.98686 (5)	0.59790 (4)	0.03549 (17)
Cl3	0.35779 (7)	0.79635 (4)	0.44965 (4)	0.02089 (13)
Cl4	0.16828 (8)	0.80635 (4)	0.25858 (4)	0.02247 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0403 (15)	0.0211 (12)	0.0281 (12)	−0.0054 (11)	−0.0160 (13)	−0.0006 (10)
C2	0.0276 (12)	0.0198 (11)	0.0172 (10)	−0.0003 (10)	0.0020 (10)	0.0041 (9)
C3	0.0209 (11)	0.0170 (10)	0.0228 (11)	−0.0052 (10)	0.0013 (10)	0.0051 (9)
C4	0.0182 (11)	0.0182 (11)	0.0240 (11)	−0.0055 (9)	0.0000 (10)	0.0013 (9)
C5	0.0251 (12)	0.0249 (12)	0.0142 (10)	−0.0029 (10)	−0.0034 (10)	0.0001 (8)
N1	0.0155 (9)	0.0104 (8)	0.0277 (10)	0.0022 (7)	0.0050 (8)	−0.0007 (7)
N2	0.0223 (10)	0.0114 (9)	0.0307 (10)	−0.0006 (8)	0.0115 (9)	0.0000 (8)
N3	0.0127 (8)	0.0143 (8)	0.0185 (8)	0.0001 (7)	0.0031 (7)	0.0020 (7)
N4	0.0229 (10)	0.0145 (9)	0.0168 (8)	−0.0028 (8)	−0.0050 (8)	0.0002 (7)
N5	0.0208 (9)	0.0148 (9)	0.0134 (8)	−0.0035 (7)	−0.0010 (8)	0.0011 (6)
P1	0.0134 (3)	0.0109 (2)	0.0151 (2)	−0.0010 (2)	0.0001 (2)	0.00049 (19)
P2	0.0147 (3)	0.0134 (3)	0.0263 (3)	−0.0013 (2)	0.0072 (2)	−0.0030 (2)
P3	0.0136 (3)	0.0114 (3)	0.0147 (2)	0.0004 (2)	0.0022 (2)	−0.00032 (19)
Cl1	0.0143 (3)	0.0296 (3)	0.0676 (5)	−0.0030 (2)	0.0000 (3)	−0.0114 (3)
Cl2	0.0514 (4)	0.0250 (3)	0.0301 (3)	−0.0014 (3)	0.0226 (3)	−0.0023 (2)
Cl3	0.0257 (3)	0.0169 (2)	0.0201 (2)	0.0049 (2)	−0.0018 (2)	0.0041 (2)
Cl4	0.0269 (3)	0.0217 (3)	0.0188 (2)	−0.0012 (2)	−0.0016 (2)	−0.0066 (2)

Geometric parameters (Å, º)

C1—N4	1.473 (3)	C5—H5A	0.9800
C1—H1A	0.9800	C5—H5B	0.9800
C1—H1B	0.9800	C5—H5C	0.9800
C1—H1C	0.9800	N1—P2	1.5607 (18)
C2—N4	1.471 (3)	N1—P1	1.6096 (19)
C2—C3	1.515 (3)	N2—P2	1.5821 (18)
C2—H2A	0.9900	N2—P3	1.589 (2)
C2—H2B	0.9900	N3—P3	1.5585 (19)
C3—C4	1.513 (3)	N3—P1	1.6300 (18)
C3—H3A	0.9900	N4—P1	1.6420 (18)
C3—H3B	0.9900	N5—P1	1.6297 (18)
C4—N5	1.470 (3)	P2—Cl1	2.0010 (8)
C4—H4A	0.9900	P2—Cl2	2.0119 (8)
C4—H4B	0.9900	P3—Cl3	1.9985 (7)
C5—N5	1.469 (3)	P3—Cl4	2.0168 (7)
N4—C1—H1A	109.5	H5B—C5—H5C	109.5
N4—C1—H1B	109.5	P2—N1—P1	124.15 (11)
H1A—C1—H1B	109.5	P2—N2—P3	118.30 (11)
N4—C1—H1C	109.5	P3—N3—P1	123.76 (11)
H1A—C1—H1C	109.5	C1—N4—C2	112.92 (19)
H1B—C1—H1C	109.5	C1—N4—P1	114.99 (15)
N4—C2—C3	110.83 (18)	C2—N4—P1	121.40 (15)
N4—C2—H2A	109.5	C5—N5—C4	113.76 (19)
C3—C2—H2A	109.5	C5—N5—P1	116.90 (14)
N4—C2—H2B	109.5	C4—N5—P1	120.09 (14)
C3—C2—H2B	109.5	N1—P1—N5	108.12 (10)
H2A—C2—H2B	108.1	N1—P1—N3	112.10 (9)
C2—C3—C4	111.93 (18)	N5—P1—N3	111.60 (10)
C2—C3—H3A	109.2	N1—P1—N4	108.99 (10)
C4—C3—H3A	109.2	N5—P1—N4	104.25 (9)
C2—C3—H3B	109.2	N3—P1—N4	111.43 (9)
C4—C3—H3B	109.2	N1—P2—N2	120.48 (10)
H3A—C3—H3B	107.9	N1—P2—Cl1	109.24 (8)
N5—C4—C3	110.32 (18)	N2—P2—Cl1	107.94 (8)
N5—C4—H4A	109.6	N1—P2—Cl2	109.12 (8)
C3—C4—H4A	109.6	N2—P2—Cl2	107.61 (8)
N5—C4—H4B	109.6	Cl1—P2—Cl2	100.62 (4)
C3—C4—H4B	109.6	N3—P3—N2	119.70 (9)
H4A—C4—H4B	108.1	N3—P3—Cl3	110.49 (7)
N5—C5—H5A	109.5	N2—P3—Cl3	107.46 (8)
N5—C5—H5B	109.5	N3—P3—Cl4	110.85 (7)
H5A—C5—H5B	109.5	N2—P3—Cl4	106.50 (8)
N5—C5—H5C	109.5	Cl3—P3—Cl4	99.97 (3)
H5A—C5—H5C	109.5
N4—C2—C3—C4	58.0 (3)	C1—N4—P1—N1	−68.38 (19)
C2—C3—C4—N5	−60.8 (2)	C2—N4—P1—N1	149.63 (16)
C3—C2—N4—C1	170.24 (19)	C1—N4—P1—N5	176.36 (17)
C3—C2—N4—P1	−47.1 (2)	C2—N4—P1—N5	34.37 (19)
C3—C4—N5—C5	−161.81 (18)	C1—N4—P1—N3	55.86 (19)
C3—C4—N5—P1	52.5 (2)	C2—N4—P1—N3	−86.13 (18)
P2—N1—P1—N5	−131.75 (14)	P1—N1—P2—N2	0.78 (19)
P2—N1—P1—N3	−8.33 (18)	P1—N1—P2—Cl1	−124.96 (12)
P2—N1—P1—N4	115.51 (14)	P1—N1—P2—Cl2	125.92 (12)
C5—N5—P1—N1	62.55 (19)	P3—N2—P2—N1	1.71 (19)
C4—N5—P1—N1	−152.77 (16)	P3—N2—P2—Cl1	128.06 (12)
C5—N5—P1—N3	−61.19 (19)	P3—N2—P2—Cl2	−124.13 (12)
C4—N5—P1—N3	83.49 (18)	P1—N3—P3—N2	−13.27 (19)
C5—N5—P1—N4	178.42 (17)	P1—N3—P3—Cl3	−138.85 (10)
C4—N5—P1—N4	−36.90 (19)	P1—N3—P3—Cl4	111.27 (11)
P3—N3—P1—N1	14.66 (17)	P2—N2—P3—N3	4.28 (19)
P3—N3—P1—N5	136.10 (12)	P2—N2—P3—Cl3	131.27 (12)
P3—N3—P1—N4	−107.81 (14)	P2—N2—P3—Cl4	−122.32 (12)