Anion–anion one-dimensional chain formation within cationic channels in tetra­butyl­ammonium di­hydrogenphosphate di­chloro­methane solvate

Light, M.E.; Camiolo, S.; Gale, P.A.; Hursthouse, M.B.

doi:10.1107/S1600536801011746

Anion-anion one-dimensional chain formation within cationic channels in tetrabutylammonium dihydrogenphosphate dichloromethane solvate

M. E. Light, S. Camiolo, P. A. Gale and M. B. Hursthouse

The title compound, C₁₆H₃₆N⁺.H₂PO₄^-.1.33CH₂Cl₂, exists as infinite one-dimensional dihydrogen phosphate chains within cationic tetrabutylammonium channels.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801011746/bt6060sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801011746/bt6060Isup2.hkl Contains datablock I

CCDC reference: 170907

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.013 Å
R factor = 0.156
wR factor = 0.393
Data-to-parameter ratio = 15.7

checkCIF results

No syntax errors found


 Alert Level A:



SHFSU_01  Alert A The absolute value of parameter shift to su ratio > 0.20
          Absolute value of the parameter shift to su ratio given   2.834
          Additional refinement cycles may be required.


 Alert Level B:



DIFMX_01  Alert B The maximum difference density is > 0.1*ZMAX*1.00
          _refine_diff_density_max given =      2.659
          Test value =      1.700

RFACG_01  Alert B The value of the R factor is > 0.15
          R factor given   0.156

RFACR_01  Alert B The value of the weighted R factor is > 0.35
          Weighted R factor given   0.393

THETM_01  Alert B The value of sine(theta_max)/wavelength is less than 0.575
          Calculated sin(theta_max)/wavelength =    0.5747

PLAT_112  Alert B ADDSYM Detects Additional (Pseudo) Symm. Elem.          Z

PLAT_214  Alert B Atom  O23    (Anion/Solvent) ADP max/min Ratio       5.80

PLAT_360  Alert B Short  C(sp3)-C(sp3) Bond  C91    -   C92    =       1.33 Ang.


 Alert Level C:



DIFMN_02  Alert C The minimum difference density is < -0.1*ZMAX*0.75
          _refine_diff_density_min given =     -1.474
          Test value =     -1.275

DIFMN_03  Alert C The minimum difference density is < -0.1*ZMAX*0.75
          The relevant atom site should be identified.

DIFMX_02  Alert C The minimum difference density is > 0.1*ZMAX*0.75
          The relevant atom site should be identified.

PLAT_213  Alert C Atom  N1     has ADP max/min Ratio ...........       3.10

PLAT_213  Alert C Atom  C84    has ADP max/min Ratio ...........       3.10

PLAT_213  Alert C Atom  C91    has ADP max/min Ratio ...........       3.40

PLAT_360  Alert C Short  C(sp3)-C(sp3) Bond  C11    -   C12    =       1.38 Ang.

PLAT_360  Alert C Short  C(sp3)-C(sp3) Bond  C47    -   C48    =       1.41 Ang.

General Notes



ABSTY_01  Extra text has been found in the _exptl_absorpt_correction_type
          field, which should be only a single keyword. A literature
          citation should be included in the _exptl_absorpt_process_details
          field.

CELLZ_01
         From the CIF: _cell_formula_units_Z   12
         From the CIF: _chemical_formula_sum  C17.33 H40.67 Cl2.67 N O4 P
         TEST: Compare cell contents of formula and atom_site data

         atom    Z*formula  cif sites diff
         C        207.96    208.00   -0.04
         H        488.04    488.00    0.04
         Cl        32.04     32.00    0.04
         N         12.00     12.00    0.00
         O         48.00     48.00    0.00
         P         12.00     12.00    0.00
          Difference between formula and atom_site contents detected.
          ALERT: check formula stoichiometry or atom site occupancies.


 1 Alert Level A = Potentially serious problem

 7 Alert Level B = Potential problem

 8 Alert Level C = Please check

Comment top

The development of receptors and sensors for anions is a rapidly developing area in supramolecular chemistry (Atwood et al., 1996; Beer & Gale, 2001; Beer & Smith, 1997; Bianchi et al., 1997; Davis et al., 1996; Kavallieratos et al., 1997; Schmidtchen & Berger, 1997; Sessler & Allen, 1999). In addition, anions have recently been exploited as templates for the formation of self-assembled supramolecular architectures in both organic and inorganic systems (Gale, 2000, 2001). It is possible to imagine how dihydrogenphosphate would oligomerize to form a coordination polymer. Tetrabutylammonium anion salts are frequently used as sources of anions, however the crystal structure of tetrabutylammonium dihydrogenphosphate has not, to the best of our knowledge, previously been elucidated. Anion chain assembly has been observed in other crystal structures (e.g. Karle & Karle, 1988), including the hydrated tetramethylammonium dihydrogenphosphate (Ohama et al., 1987) but not in the tetrabutylammonium salts that are commonly used in anion complexation studies.

The title compound, (I), crystallizes in a large triclinic cell with six tetrabutylammonium ions, six dihydrogenphosphate ions and eight dichloromethanes in the asymmetric unit. The dihydrogenphosphate ions donate and accept two hydrogen bonds to form an infinite chain and, although there are six independent ions in the asymmetric unit, the repeat length of the chain is 12 (Fig. 2). The tetrabutylammonium molecules can be seen to form cationic channels within which reside the infinite dihydrogenphosphate chains (Fig. 3).

Experimental top

The title compound was obtained from the Aldrich Chemical Company and recrystallized in a dry atmosphere via slow evaporation from dichloromethane.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: SCALEPACK (Otwinoski & Minor, 1997), COLLECT; data reduction: DENZO (Otwinoski & Minor, 1997), COLLECT, maXus (Mackay et al., 1998); program(s) used to solve structure: SHELXS 97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL 97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1998).

Figures top

	Fig. 1. Displacement ellipsoid plot of the tetrabutylammonium cations. The ellipses are drawn at the 30% probablity level and the H atoms have been omitted for clarity.
	Fig. 2. One repeating unit of the infinite hydrogen-bonded dihydrogenphosphate chain; P5 = Orange, P4 = Blue, P3 = Yellow, P6 = Purple, P2 = Red, P1 = Green.
	Fig. 3. Packing diagram showing the sheath-like nature of the tetrabutylammonium ions around the dihydrogenphosphate chains.

Tetrabutylammonium dihydrogenphosphate dichloromethane solvate top

Crystal data top

C_17.33H_40.67Cl_2.67NO₄P	Z = 12
M_r = 452.68	F(000) = 2928
Triclinic, P1	D_x = 1.233 Mg m⁻³
a = 16.1733 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 17.8443 (3) Å	Cell parameters from 58198 reflections
c = 26.7000 (5) Å	θ = 2.9–24.1°
α = 77.520 (3)°	µ = 0.43 mm⁻¹
β = 77.237 (3)°	T = 120 K
γ = 83.124 (3)°	Block, colourless
V = 7316.7 (2) Å³	0.50 × 0.15 × 0.10 mm

Data collection top

Nonius Kappa CCD Area-detector diffractometer	22291 independent reflections
Radiation source: Nonius FR591 Rotating anode	10322 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.100
Detector resolution: 9.091 pixels mm¹ pixels mm^-1	θ_max = 24.1°, θ_min = 2.9°
ϕ and ω scans to fill the Ewald sphere	h = −18→18
Absorption correction: multi-scans (SORTAV; Blessing, 1997)	k = −20→20
T_min = 0.816, T_max = 0.959	l = −30→30
58198 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.156	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.393	H-atom parameters constrained
S = 1.93	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
22291 reflections	(Δ/σ)_max = 2.834
1417 parameters	Δρ_max = 2.66 e Å⁻³
878 restraints	Δρ_min = −1.47 e Å⁻³

Crystal data top

C_17.33H_40.67Cl_2.67NO₄P	γ = 83.124 (3)°
M_r = 452.68	V = 7316.7 (2) Å³
Triclinic, P1	Z = 12
a = 16.1733 (3) Å	Mo Kα radiation
b = 17.8443 (3) Å	µ = 0.43 mm⁻¹
c = 26.7000 (5) Å	T = 120 K
α = 77.520 (3)°	0.50 × 0.15 × 0.10 mm
β = 77.237 (3)°

Data collection top

Nonius Kappa CCD Area-detector diffractometer	22291 independent reflections
Absorption correction: multi-scans (SORTAV; Blessing, 1997)	10322 reflections with I > 2σ(I)
T_min = 0.816, T_max = 0.959	R_int = 0.100
58198 measured reflections	θ_max = 24.1°

Refinement top

R[F² > 2σ(F²)] = 0.156	878 restraints
wR(F²) = 0.393	H-atom parameters constrained
S = 1.93	(Δ/σ)_max = 2.834
22291 reflections	Δρ_max = 2.66 e Å⁻³
1417 parameters	Δρ_min = −1.47 e Å⁻³

Special details top

Experimental. The crystals were extremely hygroscopic and it was necessary to mount and place them on the diffractometer under a constant stream of cold nitrogen.

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

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

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

	x	y	z	U_iso*/U_eq
N1	0.2200 (4)	0.5218 (4)	0.3025 (2)	0.047 (2)
C1	0.2035 (5)	0.4383 (4)	0.3053 (3)	0.041 (3)
H1A	0.1914	0.4336	0.2714	0.049*
H1B	0.2558	0.4051	0.3104	0.049*
C2	0.1313 (5)	0.4091 (4)	0.3482 (3)	0.036 (3)
H2A	0.0781	0.4405	0.3427	0.043*
H2B	0.1422	0.4142	0.3823	0.043*
C3	0.1209 (5)	0.3243 (4)	0.3492 (4)	0.048 (3)
H3A	0.1155	0.3188	0.3139	0.058*
H3B	0.1724	0.2927	0.3577	0.058*
C4	0.0426 (6)	0.2943 (5)	0.3894 (3)	0.057 (3)
H4A	0.0383	0.2402	0.3886	0.085*
H4B	−0.0087	0.3249	0.3808	0.085*
H4C	0.0482	0.2986	0.4244	0.085*
C5	0.1401 (5)	0.5740 (5)	0.2932 (3)	0.043 (3)
H5A	0.0956	0.5637	0.3254	0.052*
H5B	0.1537	0.6281	0.2883	0.052*
C6	0.1030 (6)	0.5671 (5)	0.2480 (3)	0.065 (3)
H6A	0.0783	0.5166	0.2558	0.078*
H6B	0.1491	0.5681	0.2167	0.078*
C7	0.0351 (6)	0.6298 (5)	0.2358 (4)	0.074 (4)
H7A	−0.0069	0.6334	0.2685	0.089*
H7B	0.0052	0.6151	0.2112	0.089*
C8	0.0675 (8)	0.7080 (5)	0.2122 (4)	0.086 (4)
H8A	0.0195	0.7456	0.2064	0.129*
H8B	0.1067	0.7060	0.1788	0.129*
H8C	0.0972	0.7233	0.2362	0.129*
C9	0.2917 (6)	0.5418 (5)	0.2559 (3)	0.064 (3)
H9A	0.2776	0.5267	0.2253	0.076*
H9B	0.3438	0.5104	0.2634	0.076*
C10	0.3117 (7)	0.6274 (6)	0.2404 (4)	0.119 (5)
H10A	0.2629	0.6585	0.2275	0.143*
H10B	0.3182	0.6450	0.2719	0.143*
C11	0.3895 (6)	0.6413 (8)	0.1996 (4)	0.134 (6)
H11A	0.3918	0.6081	0.1740	0.161*
H11B	0.3849	0.6955	0.1808	0.161*
C12	0.4655 (7)	0.6282 (11)	0.2170 (6)	0.188 (8)
H12A	0.5129	0.6385	0.1871	0.283*
H12B	0.4718	0.5745	0.2351	0.283*
H12C	0.4654	0.6624	0.2413	0.283*
C13	0.2421 (5)	0.5335 (5)	0.3517 (3)	0.040 (3)
H13A	0.1919	0.5227	0.3804	0.048*
H13B	0.2510	0.5887	0.3471	0.048*
C14	0.3181 (6)	0.4876 (5)	0.3700 (3)	0.053 (3)
H14A	0.3702	0.5015	0.3436	0.063*
H14B	0.3122	0.4321	0.3732	0.063*
C15	0.3263 (5)	0.5028 (5)	0.4228 (3)	0.056 (3)
H15A	0.3298	0.5587	0.4198	0.067*
H15B	0.2748	0.4873	0.4493	0.067*
C16	0.4036 (6)	0.4597 (6)	0.4414 (4)	0.073 (4)
H16A	0.4063	0.4715	0.4752	0.110*
H16B	0.4550	0.4754	0.4157	0.110*
H16C	0.3998	0.4043	0.4454	0.110*
N2	0.9857 (4)	0.8744 (3)	0.4275 (2)	0.040 (2)
C17	0.9985 (5)	0.9610 (4)	0.4101 (4)	0.048 (3)
H17A	0.9536	0.9858	0.3907	0.057*
H17B	0.9909	0.9835	0.4417	0.057*
C18	1.0836 (5)	0.9802 (4)	0.3760 (4)	0.060 (4)
H18A	1.0898	0.9631	0.3424	0.072*
H18B	1.1296	0.9528	0.3937	0.072*
C19	1.0914 (5)	1.0679 (5)	0.3655 (4)	0.064 (4)
H19A	1.0464	1.0946	0.3469	0.077*
H19B	1.0820	1.0848	0.3995	0.077*
C20	1.1765 (6)	1.0911 (5)	0.3336 (4)	0.077 (4)
H20A	1.1778	1.1471	0.3279	0.116*
H20B	1.1859	1.0751	0.2998	0.116*
H20C	1.2213	1.0661	0.3524	0.116*
C21	1.0566 (5)	0.8311 (5)	0.4544 (3)	0.042 (3)
H21A	1.0452	0.7760	0.4652	0.051*
H21B	1.1110	0.8347	0.4285	0.051*
C22	1.0676 (5)	0.8595 (5)	0.5021 (3)	0.042 (3)
H22A	1.0130	0.8592	0.5277	0.051*
H22B	1.0849	0.9129	0.4915	0.051*
C23	1.1357 (5)	0.8069 (5)	0.5273 (3)	0.051 (3)
H23A	1.1189	0.7533	0.5367	0.061*
H23B	1.1903	0.8081	0.5016	0.061*
C24	1.1479 (6)	0.8316 (5)	0.5760 (4)	0.066 (3)
H24A	1.1927	0.7976	0.5905	0.099*
H24B	1.0946	0.8282	0.6021	0.099*
H24C	1.1641	0.8847	0.5669	0.099*
C25	0.8996 (5)	0.8668 (4)	0.4629 (3)	0.040 (3)
H25A	0.8580	0.9023	0.4455	0.048*
H25B	0.9015	0.8845	0.4953	0.048*
C26	0.8658 (5)	0.7863 (4)	0.4789 (3)	0.041 (3)
H26A	0.8516	0.7720	0.4481	0.049*
H26B	0.9104	0.7481	0.4910	0.049*
C27	0.7871 (5)	0.7848 (4)	0.5223 (3)	0.044 (3)
H27A	0.8024	0.7967	0.5535	0.053*
H27B	0.7441	0.8254	0.5107	0.053*
C28	0.7496 (6)	0.7100 (5)	0.5369 (4)	0.073 (4)
H28A	0.7005	0.7115	0.5658	0.110*
H28B	0.7921	0.6695	0.5479	0.110*
H28C	0.7314	0.6993	0.5067	0.110*
C29	0.9904 (5)	0.8392 (5)	0.3799 (3)	0.047 (3)
H29A	1.0486	0.8434	0.3584	0.056*
H29B	0.9819	0.7837	0.3922	0.056*
C30	0.9278 (6)	0.8734 (5)	0.3447 (3)	0.062 (3)
H30A	0.9443	0.9249	0.3250	0.074*
H30B	0.8703	0.8797	0.3665	0.074*
C31	0.9258 (6)	0.8221 (5)	0.3063 (4)	0.070 (4)
H31A	0.8954	0.8514	0.2789	0.084*
H31B	0.9849	0.8092	0.2889	0.084*
C32	0.8839 (7)	0.7489 (5)	0.3307 (4)	0.081 (4)
H32A	0.8868	0.7184	0.3038	0.122*
H32B	0.8243	0.7609	0.3462	0.122*
H32C	0.9133	0.7194	0.3580	0.122*
N3	0.7577 (4)	0.4926 (3)	0.1900 (2)	0.038 (2)
C33	0.8323 (5)	0.4376 (4)	0.2054 (3)	0.034 (3)
H33A	0.8151	0.3842	0.2130	0.041*
H33B	0.8803	0.4420	0.1749	0.041*
C34	0.8634 (6)	0.4506 (5)	0.2519 (3)	0.052 (3)
H34A	0.8152	0.4498	0.2822	0.063*
H34B	0.8862	0.5020	0.2435	0.063*
C35	0.9330 (6)	0.3885 (4)	0.2664 (4)	0.049 (3)
H35A	0.9777	0.3853	0.2348	0.059*
H35B	0.9595	0.4038	0.2924	0.059*
C36	0.9004 (7)	0.3116 (5)	0.2884 (4)	0.068 (4)
H36A	0.9473	0.2743	0.2968	0.101*
H36B	0.8751	0.2957	0.2626	0.101*
H36C	0.8572	0.3140	0.3203	0.101*
C37	0.7788 (5)	0.5765 (4)	0.1821 (3)	0.041 (3)
H37A	0.7309	0.6106	0.1704	0.050*
H37B	0.7833	0.5869	0.2163	0.050*
C38	0.8598 (5)	0.5975 (4)	0.1430 (3)	0.044 (3)
H38A	0.8564	0.5878	0.1084	0.053*
H38B	0.9088	0.5651	0.1547	0.053*
C39	0.8727 (5)	0.6827 (4)	0.1383 (4)	0.050 (3)
H39A	0.8250	0.7151	0.1252	0.060*
H39B	0.8734	0.6928	0.1733	0.060*
C40	0.9558 (6)	0.7036 (5)	0.1012 (4)	0.062 (3)
H40A	0.9627	0.7584	0.0980	0.093*
H40B	0.9553	0.6933	0.0667	0.093*
H40C	1.0032	0.6727	0.1149	0.093*
C41	0.7422 (5)	0.4745 (5)	0.1408 (3)	0.038 (3)
H41A	0.7347	0.4187	0.1474	0.045*
H41B	0.7942	0.4842	0.1135	0.045*
C42	0.6664 (5)	0.5178 (5)	0.1182 (3)	0.039 (3)
H42A	0.6127	0.5037	0.1428	0.047*
H42B	0.6699	0.5740	0.1138	0.047*
C43	0.6665 (5)	0.4982 (5)	0.0663 (3)	0.049 (3)
H43A	0.7209	0.5115	0.0421	0.059*
H43B	0.6630	0.4420	0.0711	0.059*
C44	0.5945 (6)	0.5394 (6)	0.0420 (4)	0.071 (4)
H44A	0.5967	0.5233	0.0088	0.106*
H44B	0.5993	0.5950	0.0354	0.106*
H44C	0.5404	0.5267	0.0658	0.106*
C45	0.6798 (5)	0.4804 (5)	0.2334 (3)	0.050 (3)
H45A	0.6923	0.4941	0.2648	0.060*
H45B	0.6331	0.5171	0.2226	0.060*
C46	0.6483 (6)	0.4034 (5)	0.2489 (4)	0.084 (4)
H46A	0.6910	0.3665	0.2643	0.100*
H46B	0.6394	0.3865	0.2176	0.100*
C47	0.5613 (7)	0.4044 (7)	0.2904 (6)	0.123 (5)
H47A	0.5732	0.4108	0.3240	0.147*
H47B	0.5240	0.4496	0.2780	0.147*
C48	0.5177 (13)	0.3375 (10)	0.2993 (10)	0.308 (16)
H48A	0.4642	0.3425	0.3245	0.461*
H48B	0.5530	0.2927	0.3133	0.461*
H48C	0.5056	0.3307	0.2663	0.461*
N4	0.5386 (4)	0.2220 (3)	0.0609 (2)	0.030 (2)
C49	0.6085 (5)	0.1581 (4)	0.0733 (3)	0.033 (3)
H49A	0.6608	0.1826	0.0724	0.039*
H49B	0.5900	0.1292	0.1094	0.039*
C50	0.6299 (5)	0.1017 (4)	0.0365 (3)	0.044 (3)
H50A	0.6542	0.1285	0.0007	0.053*
H50B	0.5779	0.0784	0.0354	0.053*
C51	0.6949 (6)	0.0389 (5)	0.0570 (4)	0.054 (3)
H51A	0.7463	0.0630	0.0581	0.065*
H51B	0.6703	0.0135	0.0932	0.065*
C52	0.7195 (7)	−0.0204 (5)	0.0233 (4)	0.086 (4)
H52A	0.7598	−0.0599	0.0380	0.129*
H52B	0.7462	0.0042	−0.0122	0.129*
H52C	0.6687	−0.0442	0.0219	0.129*
C53	0.5632 (5)	0.2688 (5)	0.0060 (3)	0.042 (3)
H53A	0.5663	0.2347	−0.0192	0.051*
H53B	0.5171	0.3095	0.0001	0.051*
C54	0.6459 (5)	0.3066 (5)	−0.0068 (3)	0.046 (3)
H54A	0.6927	0.2679	0.0011	0.056*
H54B	0.6419	0.3464	0.0145	0.056*
C55	0.6633 (6)	0.3433 (6)	−0.0648 (3)	0.062 (3)
H55A	0.6625	0.3035	−0.0853	0.075*
H55B	0.6169	0.3832	−0.0716	0.075*
C56	0.7462 (6)	0.3793 (6)	−0.0835 (4)	0.077 (4)
H56A	0.7535	0.4008	−0.1211	0.115*
H56B	0.7927	0.3402	−0.0772	0.115*
H56C	0.7467	0.4205	−0.0645	0.115*
C57	0.4557 (4)	0.1888 (4)	0.0646 (3)	0.036 (3)
H57A	0.4128	0.2322	0.0577	0.043*
H57B	0.4634	0.1597	0.0360	0.043*
C58	0.4190 (5)	0.1363 (5)	0.1154 (3)	0.053 (3)
H58A	0.4116	0.1638	0.1447	0.064*
H58B	0.4592	0.0906	0.1219	0.064*
C59	0.3338 (5)	0.1103 (6)	0.1134 (4)	0.074 (4)
H59A	0.2938	0.1561	0.1067	0.088*
H59B	0.3414	0.0829	0.0840	0.088*
C60	0.2973 (7)	0.0598 (6)	0.1618 (4)	0.104 (5)
H60A	0.2434	0.0434	0.1584	0.156*
H60B	0.2870	0.0875	0.1908	0.156*
H60C	0.3368	0.0145	0.1688	0.156*
C61	0.5317 (5)	0.2712 (4)	0.1023 (3)	0.040 (3)
H61A	0.5212	0.2371	0.1373	0.048*
H61B	0.5872	0.2927	0.0976	0.048*
C62	0.4643 (6)	0.3362 (5)	0.1020 (3)	0.055 (3)
H62A	0.4074	0.3162	0.1094	0.066*
H62B	0.4726	0.3711	0.0673	0.066*
C63	0.4716 (6)	0.3794 (5)	0.1447 (4)	0.072 (4)
H63A	0.4683	0.3425	0.1785	0.086*
H63B	0.5278	0.4011	0.1357	0.086*
C64	0.4058 (8)	0.4408 (7)	0.1506 (5)	0.134 (7)
H64A	0.4137	0.4672	0.1775	0.201*
H64B	0.3501	0.4194	0.1609	0.201*
H64C	0.4087	0.4775	0.1172	0.201*
N5	0.0225 (4)	0.1350 (3)	0.0887 (3)	0.040 (2)
C65	0.0126 (5)	0.0487 (4)	0.1089 (4)	0.048 (3)
H65A	0.0128	0.0244	0.0788	0.058*
H65B	0.0623	0.0255	0.1243	0.058*
C66	−0.0682 (6)	0.0302 (5)	0.1498 (4)	0.078 (4)
H66A	−0.1177	0.0605	0.1375	0.094*
H66B	−0.0639	0.0445	0.1829	0.094*
C67	−0.0812 (7)	−0.0557 (5)	0.1598 (4)	0.082 (4)
H67A	−0.0264	−0.0862	0.1621	0.098*
H67B	−0.1214	−0.0704	0.1935	0.098*
C68	−0.1146 (8)	−0.0724 (6)	0.1177 (5)	0.125 (6)
H68A	−0.1219	−0.1276	0.1240	0.188*
H68B	−0.0749	−0.0576	0.0844	0.188*
H68C	−0.1697	−0.0433	0.1161	0.188*
C69	0.1101 (5)	0.1418 (4)	0.0526 (3)	0.041 (3)
H69A	0.1523	0.1094	0.0712	0.049*
H69B	0.1094	0.1203	0.0215	0.049*
C70	0.1401 (5)	0.2213 (4)	0.0339 (3)	0.041 (3)
H70A	0.1545	0.2392	0.0633	0.049*
H70B	0.0940	0.2571	0.0214	0.049*
C71	0.2175 (5)	0.2216 (5)	−0.0101 (4)	0.055 (3)
H71A	0.2616	0.1822	0.0015	0.066*
H71B	0.2017	0.2083	−0.0407	0.066*
C72	0.2531 (6)	0.2995 (5)	−0.0259 (4)	0.071 (4)
H72A	0.3025	0.2987	−0.0547	0.106*
H72B	0.2706	0.3120	0.0041	0.106*
H72C	0.2095	0.3385	−0.0373	0.106*
C73	0.0152 (6)	0.1756 (5)	0.1337 (3)	0.054 (3)
H73A	−0.0428	0.1708	0.1553	0.064*
H73B	0.0217	0.2310	0.1192	0.064*
C74	0.0799 (6)	0.1460 (5)	0.1696 (3)	0.064 (4)
H74A	0.0692	0.0925	0.1879	0.076*
H74B	0.1381	0.1455	0.1479	0.076*
C75	0.0740 (7)	0.1957 (5)	0.2097 (4)	0.075 (4)
H75A	0.0143	0.2012	0.2286	0.089*
H75B	0.1090	0.1703	0.2356	0.089*
C76	0.1029 (8)	0.2711 (6)	0.1855 (5)	0.094 (5)
H76A	0.0978	0.3019	0.2124	0.141*
H76B	0.0679	0.2966	0.1601	0.141*
H76C	0.1624	0.2659	0.1675	0.141*
C77	−0.0481 (5)	0.1714 (5)	0.0601 (3)	0.041 (3)
H77A	−0.1029	0.1665	0.0855	0.050*
H77B	−0.0402	0.2271	0.0481	0.050*
C78	−0.0554 (5)	0.1391 (5)	0.0135 (3)	0.047 (3)
H78A	−0.0669	0.0841	0.0247	0.056*
H78B	−0.0013	0.1431	−0.0127	0.056*
C79	−0.1278 (6)	0.1847 (5)	−0.0108 (3)	0.054 (3)
H79A	−0.1805	0.1832	0.0165	0.065*
H79B	−0.1143	0.2391	−0.0230	0.065*
C80	−0.1435 (6)	0.1545 (6)	−0.0560 (4)	0.065 (4)
H80A	−0.1906	0.1857	−0.0698	0.098*
H80B	−0.1580	0.1009	−0.0440	0.098*
H80C	−0.0921	0.1572	−0.0836	0.098*
N6	0.4709 (4)	0.7650 (4)	0.4390 (2)	0.043 (2)
C81	0.5503 (5)	0.8023 (5)	0.4425 (3)	0.045 (3)
H81A	0.5353	0.8292	0.4724	0.054*
H81B	0.5949	0.7609	0.4500	0.054*
C82	0.5872 (5)	0.8594 (5)	0.3936 (3)	0.057 (3)
H82A	0.5442	0.9021	0.3852	0.068*
H82B	0.6055	0.8335	0.3632	0.068*
C83	0.6636 (6)	0.8902 (6)	0.4057 (4)	0.085 (4)
H83A	0.6445	0.9141	0.4370	0.102*
H83B	0.7059	0.8469	0.4139	0.102*
C84	0.7038 (7)	0.9479 (7)	0.3611 (5)	0.126 (6)
H84A	0.7523	0.9663	0.3700	0.189*
H84B	0.6623	0.9913	0.3534	0.189*
H84C	0.7235	0.9241	0.3303	0.189*
C85	0.4005 (5)	0.8281 (4)	0.4265 (3)	0.042 (3)
H85A	0.4200	0.8583	0.3909	0.050*
H85B	0.3496	0.8029	0.4258	0.050*
C86	0.3741 (6)	0.8837 (5)	0.4642 (3)	0.050 (3)
H86A	0.4239	0.9095	0.4662	0.060*
H86B	0.3500	0.8556	0.4998	0.060*
C87	0.3074 (6)	0.9428 (5)	0.4432 (4)	0.058 (3)
H87A	0.3320	0.9689	0.4072	0.070*
H87B	0.2584	0.9159	0.4414	0.070*
C88	0.2768 (7)	1.0024 (5)	0.4769 (4)	0.086 (4)
H88A	0.2341	1.0389	0.4620	0.129*
H88B	0.3249	1.0301	0.4781	0.129*
H88C	0.2515	0.9770	0.5124	0.129*
C89	0.4446 (6)	0.7150 (5)	0.4930 (3)	0.064 (4)
H89A	0.4938	0.6795	0.5013	0.077*
H89B	0.4296	0.7486	0.5193	0.077*
C90	0.3695 (7)	0.6678 (7)	0.4980 (4)	0.103 (4)
H90A	0.3177	0.7030	0.4957	0.123*
H90B	0.3804	0.6404	0.4683	0.123*
C91	0.3543 (8)	0.6104 (9)	0.5483 (5)	0.198 (9)
H91A	0.3469	0.5599	0.5409	0.238*
H91B	0.4048	0.6044	0.5645	0.238*
C92	0.2860 (11)	0.6311 (11)	0.5820 (5)	0.221 (11)
H92A	0.2908	0.6052	0.6177	0.332*
H92B	0.2349	0.6162	0.5737	0.332*
H92C	0.2820	0.6870	0.5795	0.332*
C93	0.4892 (6)	0.7204 (5)	0.3947 (3)	0.059 (3)
H93A	0.4359	0.6995	0.3934	0.070*
H93B	0.5063	0.7568	0.3612	0.070*
C94	0.5574 (7)	0.6549 (6)	0.3986 (4)	0.089 (4)
H94A	0.5426	0.6191	0.4326	0.107*
H94B	0.6123	0.6754	0.3970	0.107*
C95	0.5663 (9)	0.6106 (6)	0.3532 (4)	0.111 (6)
H95A	0.5987	0.5602	0.3609	0.133*
H95B	0.5095	0.6016	0.3484	0.133*
C96	0.6138 (11)	0.6615 (8)	0.3036 (5)	0.183 (9)
H96A	0.6192	0.6368	0.2736	0.275*
H96B	0.6706	0.6685	0.3085	0.275*
H96C	0.5820	0.7118	0.2973	0.275*
P1	0.06399 (15)	0.59852 (12)	0.45673 (9)	0.0325 (7)
O1	0.0795 (4)	0.5160 (3)	0.4511 (2)	0.056 (2)
O2	0.1356 (3)	0.6232 (3)	0.4785 (2)	0.0506 (19)
H02	0.1703	0.6470	0.4537	0.076*
O3	0.0532 (3)	0.6557 (3)	0.40727 (19)	0.0410 (17)
O4	−0.0176 (3)	0.6052 (3)	0.4990 (2)	0.0374 (17)
H04	−0.0360	0.5615	0.5111	0.056*
P2	0.24443 (15)	0.75041 (13)	0.36257 (9)	0.0325 (7)
O5	0.2377 (4)	0.7147 (4)	0.4191 (2)	0.067 (2)
O6	0.3274 (3)	0.7278 (3)	0.3285 (2)	0.053 (2)
O7	0.2323 (3)	0.8388 (3)	0.3564 (2)	0.0428 (18)
H07	0.2718	0.8588	0.3332	0.064*
O8	0.1709 (3)	0.7255 (3)	0.34183 (19)	0.0330 (16)
H08	0.1392	0.6984	0.3666	0.049*
P3	0.93061 (14)	0.40520 (12)	0.04497 (9)	0.0291 (7)
O9	0.8619 (3)	0.3734 (3)	0.0238 (2)	0.0433 (18)
H09	0.8287	0.3485	0.0490	0.065*
O10	0.9100 (4)	0.4894 (3)	0.0453 (2)	0.050 (2)
O11	1.0150 (3)	0.3935 (3)	0.0057 (2)	0.0375 (18)
H011	1.0314	0.4365	−0.0108	0.056*
O12	0.9367 (3)	0.3566 (3)	0.09825 (19)	0.0403 (17)
P4	0.75276 (15)	0.24823 (13)	0.14253 (9)	0.0308 (7)
O13	0.7467 (3)	0.2976 (3)	0.0897 (2)	0.0483 (19)
O14	0.8252 (3)	0.2760 (3)	0.16352 (19)	0.0330 (16)
H014	0.8578	0.3017	0.1384	0.049*
O15	0.7681 (3)	0.1635 (3)	0.1424 (2)	0.0415 (18)
O16	0.6712 (3)	0.2629 (3)	0.1831 (2)	0.0440 (19)
H016	0.6525	0.2207	0.1995	0.066*
P5	0.59158 (17)	0.07376 (16)	0.22572 (11)	0.0525 (9)
O17	0.6890 (3)	0.0588 (3)	0.2097 (2)	0.054 (2)
H017	0.7088	0.0964	0.1871	0.081*
O18	0.5698 (4)	0.1577 (4)	0.2186 (3)	0.098 (3)
O19	0.5631 (4)	0.0285 (4)	0.2811 (2)	0.068 (2)
O20	0.5492 (5)	0.0447 (5)	0.1889 (2)	0.138 (3)
H020	0.5070	0.0209	0.2063	0.207*
P6	0.42634 (18)	0.89779 (19)	0.26767 (12)	0.0750 (11)
O21	0.4540 (4)	0.9405 (4)	0.2131 (2)	0.069 (2)
O22	0.4973 (5)	0.8959 (5)	0.2965 (3)	0.122 (3)
H022	0.5366	0.9214	0.2769	0.183*
O23	0.4301 (5)	0.8113 (4)	0.2672 (4)	0.160 (5)
H023	0.3826	0.7944	0.2819	0.240*
O24	0.3378 (4)	0.9237 (3)	0.2920 (2)	0.076 (3)
C97	0.5136 (8)	0.1379 (5)	0.8849 (3)	0.146 (7)
H97A	0.4754	0.1221	0.8654	0.175*
H97B	0.5670	0.1520	0.8598	0.175*
Cl1	0.5364 (3)	0.0613 (3)	0.93200 (15)	0.1443 (17)
Cl2	0.4660 (3)	0.2184 (3)	0.90948 (16)	0.1478 (17)
C98	0.8684 (5)	0.5455 (5)	0.4221 (3)	0.056 (3)
H98A	0.8691	0.5007	0.4513	0.067*
H98B	0.9109	0.5800	0.4236	0.067*
Cl3	0.76786 (19)	0.59430 (17)	0.42954 (13)	0.0851 (11)
Cl4	0.8960 (2)	0.51379 (18)	0.36262 (11)	0.0825 (11)
C99	0.3317 (8)	0.1445 (7)	0.7840 (4)	0.144 (6)
H99A	0.3876	0.1538	0.7605	0.172*
H99B	0.3262	0.0883	0.7930	0.172*
Cl5	0.2520 (3)	0.1891 (2)	0.75182 (17)	0.1362 (16)
Cl6	0.3268 (3)	0.1794 (2)	0.84170 (17)	0.1353 (15)
C100	0.4927 (8)	0.1275 (5)	0.3888 (4)	0.090 (4)
H10C	0.4356	0.1221	0.3828	0.108*
H10D	0.5346	0.1236	0.3561	0.108*
Cl7	0.5158 (3)	0.0571 (2)	0.43734 (15)	0.1303 (16)
Cl8	0.4948 (4)	0.2166 (3)	0.40473 (18)	0.182 (2)
C101	0.2125 (6)	0.8662 (5)	0.2282 (3)	0.060 (3)
H10E	0.2575	0.8915	0.2367	0.072*
H10F	0.2032	0.8174	0.2540	0.072*
Cl9	0.2456 (3)	0.8463 (2)	0.16603 (14)	0.1248 (15)
Cl10	0.1168 (2)	0.9271 (2)	0.23329 (15)	0.1117 (14)
C102	0.1250 (5)	0.4538 (6)	0.0830 (3)	0.059 (3)
H10P	0.0871	0.4154	0.0810	0.071*
H10Q	0.1246	0.4963	0.0523	0.071*
Cl11	0.2285 (2)	0.41080 (19)	0.08117 (14)	0.0958 (12)
Cl12	0.08617 (17)	0.49015 (15)	0.14085 (10)	0.0626 (9)
C103	0.2175 (6)	0.8624 (6)	0.7237 (3)	0.077 (4)
H10G	0.2041	0.8212	0.7550	0.093*
H10H	0.2475	0.9012	0.7329	0.093*
Cl13	0.1239 (2)	0.90537 (18)	0.70507 (12)	0.0871 (11)
Cl14	0.2840 (2)	0.8231 (2)	0.67235 (15)	0.1053 (13)
C104	0.3699 (7)	0.1944 (8)	0.2630 (4)	0.138 (7)
H10I	0.4290	0.1987	0.2430	0.165*
H10J	0.3585	0.1393	0.2722	0.165*
Cl15	0.2993 (3)	0.2458 (3)	0.22479 (18)	0.1446 (18)
Cl16	0.3571 (4)	0.2316 (5)	0.3206 (3)	0.288 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.058 (5)	0.064 (5)	0.020 (4)	−0.038 (4)	0.019 (4)	−0.017 (4)
C1	0.051 (6)	0.039 (5)	0.026 (5)	−0.018 (5)	0.017 (5)	−0.010 (4)
C2	0.030 (5)	0.044 (5)	0.034 (5)	−0.019 (5)	−0.002 (5)	−0.006 (4)
C3	0.051 (7)	0.026 (5)	0.067 (7)	−0.012 (5)	−0.002 (6)	−0.011 (5)
C4	0.065 (7)	0.052 (6)	0.057 (7)	−0.030 (6)	−0.015 (6)	−0.002 (5)
C5	0.057 (7)	0.035 (5)	0.038 (6)	−0.009 (5)	0.002 (5)	−0.017 (5)
C6	0.095 (8)	0.066 (7)	0.040 (6)	−0.052 (7)	−0.007 (6)	−0.003 (6)
C7	0.085 (9)	0.086 (8)	0.056 (7)	−0.038 (7)	−0.022 (7)	0.003 (6)
C8	0.148 (12)	0.070 (8)	0.043 (7)	−0.036 (8)	−0.026 (7)	0.003 (6)
C9	0.059 (7)	0.083 (8)	0.043 (6)	−0.046 (6)	0.021 (6)	−0.008 (6)
C10	0.168 (11)	0.147 (10)	0.050 (7)	−0.126 (9)	0.034 (8)	−0.035 (7)
C11	0.138 (12)	0.190 (13)	0.073 (9)	−0.114 (11)	0.051 (9)	−0.043 (9)
C12	0.045 (10)	0.33 (2)	0.230 (18)	0.018 (13)	−0.018 (11)	−0.174 (17)
C13	0.043 (6)	0.042 (6)	0.032 (5)	−0.013 (5)	0.001 (5)	−0.004 (5)
C14	0.068 (7)	0.054 (6)	0.035 (6)	−0.028 (6)	0.008 (6)	−0.013 (5)
C15	0.044 (6)	0.056 (7)	0.064 (7)	−0.010 (6)	−0.017 (6)	0.005 (6)
C16	0.059 (8)	0.084 (8)	0.071 (8)	0.020 (7)	−0.021 (7)	−0.011 (7)
N2	0.041 (5)	0.031 (4)	0.040 (5)	0.006 (4)	−0.002 (4)	−0.002 (4)
C17	0.032 (6)	0.019 (5)	0.082 (7)	0.002 (5)	−0.006 (6)	0.003 (5)
C18	0.052 (7)	0.032 (6)	0.076 (8)	0.003 (5)	0.003 (6)	0.013 (5)
C19	0.040 (7)	0.044 (6)	0.092 (8)	−0.001 (6)	0.009 (6)	0.000 (6)
C20	0.067 (8)	0.048 (7)	0.093 (9)	−0.013 (6)	0.008 (7)	0.016 (6)
C21	0.029 (6)	0.047 (6)	0.045 (6)	0.017 (5)	−0.016 (5)	0.003 (5)
C22	0.049 (6)	0.034 (5)	0.038 (6)	−0.001 (5)	−0.003 (5)	0.001 (5)
C23	0.035 (6)	0.053 (6)	0.063 (7)	−0.006 (5)	−0.019 (5)	0.001 (6)
C24	0.075 (8)	0.060 (7)	0.074 (8)	−0.024 (6)	−0.029 (7)	−0.009 (6)
C25	0.028 (5)	0.037 (5)	0.047 (6)	0.005 (5)	−0.007 (5)	0.000 (5)
C26	0.031 (6)	0.043 (6)	0.042 (6)	0.001 (5)	−0.007 (5)	0.004 (5)
C27	0.046 (6)	0.035 (5)	0.038 (6)	−0.014 (5)	0.008 (5)	0.009 (5)
C28	0.067 (8)	0.067 (8)	0.077 (8)	−0.018 (7)	−0.007 (7)	0.003 (7)
C29	0.032 (6)	0.051 (6)	0.047 (6)	−0.005 (5)	−0.008 (5)	0.014 (5)
C30	0.051 (7)	0.061 (7)	0.065 (7)	0.006 (6)	−0.032 (6)	0.023 (6)
C31	0.058 (7)	0.072 (8)	0.078 (8)	−0.009 (6)	−0.041 (6)	0.016 (7)
C32	0.090 (9)	0.058 (8)	0.101 (9)	−0.007 (7)	−0.043 (8)	−0.001 (7)
N3	0.037 (5)	0.040 (5)	0.032 (4)	0.002 (4)	0.000 (4)	−0.007 (4)
C33	0.036 (6)	0.040 (5)	0.026 (5)	−0.004 (5)	0.004 (5)	−0.014 (4)
C34	0.068 (7)	0.048 (6)	0.042 (6)	−0.011 (6)	−0.011 (6)	−0.008 (5)
C35	0.055 (7)	0.047 (6)	0.046 (6)	0.001 (6)	−0.013 (5)	−0.012 (5)
C36	0.071 (8)	0.063 (7)	0.064 (7)	−0.008 (7)	−0.012 (7)	−0.003 (6)
C37	0.045 (6)	0.025 (5)	0.047 (6)	−0.006 (5)	−0.003 (5)	0.001 (5)
C38	0.058 (7)	0.036 (5)	0.035 (6)	−0.010 (5)	−0.001 (5)	−0.005 (5)
C39	0.048 (7)	0.031 (5)	0.065 (7)	−0.009 (5)	0.003 (6)	−0.006 (5)
C40	0.074 (8)	0.051 (6)	0.061 (7)	−0.039 (6)	−0.008 (6)	0.000 (5)
C41	0.035 (6)	0.046 (6)	0.034 (5)	0.002 (5)	−0.010 (5)	−0.013 (5)
C42	0.027 (5)	0.047 (6)	0.040 (6)	0.000 (5)	−0.009 (5)	−0.004 (5)
C43	0.037 (6)	0.047 (6)	0.063 (7)	0.004 (5)	−0.025 (5)	0.002 (5)
C44	0.046 (7)	0.066 (7)	0.087 (8)	−0.014 (6)	−0.031 (6)	0.036 (6)
C45	0.031 (6)	0.046 (6)	0.056 (7)	−0.012 (5)	0.021 (5)	0.003 (5)
C46	0.088 (7)	0.077 (6)	0.074 (7)	−0.033 (6)	0.022 (6)	−0.015 (6)
C47	0.085 (8)	0.100 (8)	0.163 (9)	−0.026 (7)	−0.017 (7)	0.020 (7)
C48	0.34 (3)	0.18 (2)	0.43 (4)	−0.06 (2)	−0.15 (3)	0.00 (2)
N4	0.019 (4)	0.038 (4)	0.029 (4)	−0.004 (4)	−0.012 (3)	0.008 (3)
C49	0.025 (5)	0.040 (5)	0.031 (5)	−0.005 (5)	−0.009 (4)	0.004 (4)
C50	0.039 (6)	0.047 (6)	0.044 (6)	−0.001 (5)	0.002 (5)	−0.015 (5)
C51	0.054 (7)	0.038 (6)	0.064 (7)	0.010 (6)	−0.007 (6)	−0.007 (5)
C52	0.083 (9)	0.067 (8)	0.097 (9)	0.022 (7)	0.004 (8)	−0.029 (7)
C53	0.034 (6)	0.050 (6)	0.034 (5)	0.002 (5)	−0.007 (5)	0.009 (5)
C54	0.037 (6)	0.064 (7)	0.028 (5)	−0.011 (5)	−0.001 (5)	0.009 (5)
C55	0.059 (7)	0.058 (7)	0.064 (7)	−0.010 (6)	−0.025 (6)	0.014 (6)
C56	0.075 (8)	0.079 (8)	0.070 (8)	−0.042 (7)	−0.012 (7)	0.016 (7)
C57	0.025 (5)	0.036 (5)	0.051 (6)	−0.001 (4)	−0.021 (5)	−0.006 (5)
C58	0.038 (6)	0.062 (7)	0.053 (6)	−0.011 (6)	−0.016 (5)	0.016 (5)
C59	0.025 (6)	0.067 (7)	0.113 (9)	−0.013 (6)	−0.022 (6)	0.031 (7)
C60	0.062 (8)	0.073 (8)	0.145 (11)	−0.019 (7)	−0.023 (8)	0.057 (8)
C61	0.022 (5)	0.051 (6)	0.043 (6)	0.003 (5)	−0.012 (5)	−0.001 (5)
C62	0.061 (7)	0.050 (6)	0.047 (6)	0.018 (6)	−0.006 (6)	−0.013 (5)
C63	0.046 (7)	0.049 (7)	0.126 (10)	0.012 (6)	−0.020 (7)	−0.036 (7)
C64	0.154 (15)	0.107 (11)	0.120 (12)	−0.036 (11)	0.024 (12)	−0.015 (10)
N5	0.028 (4)	0.028 (4)	0.056 (5)	0.001 (4)	−0.003 (4)	0.002 (4)
C65	0.029 (6)	0.030 (5)	0.074 (7)	0.000 (5)	0.002 (6)	0.000 (5)
C66	0.074 (8)	0.045 (7)	0.091 (9)	−0.029 (6)	0.021 (7)	0.013 (6)
C67	0.050 (7)	0.061 (8)	0.127 (11)	−0.013 (6)	−0.016 (8)	0.000 (8)
C68	0.111 (12)	0.052 (8)	0.212 (17)	−0.017 (8)	−0.040 (12)	−0.013 (10)
C69	0.038 (6)	0.031 (5)	0.047 (6)	0.006 (5)	−0.007 (5)	−0.001 (5)
C70	0.034 (6)	0.032 (5)	0.053 (6)	−0.003 (5)	0.001 (5)	−0.008 (5)
C71	0.044 (7)	0.047 (6)	0.060 (7)	0.005 (6)	−0.002 (6)	0.005 (5)
C72	0.060 (7)	0.040 (6)	0.093 (8)	−0.019 (6)	0.002 (7)	0.016 (6)
C73	0.049 (7)	0.052 (6)	0.054 (7)	0.014 (6)	−0.004 (6)	−0.011 (6)
C74	0.066 (8)	0.057 (7)	0.064 (7)	0.017 (6)	−0.028 (6)	0.001 (6)
C75	0.082 (9)	0.076 (8)	0.060 (7)	0.001 (7)	−0.016 (7)	−0.001 (7)
C76	0.125 (11)	0.072 (8)	0.101 (10)	0.012 (8)	−0.058 (9)	−0.025 (7)
C77	0.029 (6)	0.039 (6)	0.052 (6)	0.000 (5)	−0.007 (5)	−0.003 (5)
C78	0.030 (6)	0.046 (6)	0.065 (7)	−0.003 (5)	−0.009 (5)	−0.013 (5)
C79	0.053 (7)	0.064 (7)	0.046 (6)	−0.014 (6)	−0.008 (6)	−0.011 (5)
C80	0.058 (7)	0.069 (7)	0.073 (8)	−0.015 (6)	−0.002 (6)	−0.027 (6)
N6	0.031 (5)	0.054 (5)	0.040 (5)	−0.007 (4)	−0.009 (4)	0.006 (4)
C81	0.032 (6)	0.059 (6)	0.046 (6)	−0.007 (5)	−0.012 (5)	−0.007 (5)
C82	0.035 (6)	0.060 (7)	0.063 (7)	−0.013 (6)	−0.001 (6)	0.010 (6)
C83	0.031 (6)	0.066 (7)	0.129 (10)	−0.014 (6)	−0.019 (7)	0.053 (7)
C84	0.061 (8)	0.084 (10)	0.238 (17)	0.007 (8)	−0.085 (10)	0.008 (11)
C85	0.033 (6)	0.042 (6)	0.052 (6)	0.006 (5)	−0.019 (5)	−0.004 (5)
C86	0.045 (6)	0.049 (6)	0.058 (6)	0.010 (5)	−0.023 (5)	−0.009 (5)
C87	0.038 (6)	0.064 (7)	0.076 (8)	−0.007 (6)	−0.011 (6)	−0.022 (6)
C88	0.091 (10)	0.061 (7)	0.100 (9)	0.006 (7)	0.016 (8)	−0.046 (7)
C89	0.050 (7)	0.084 (8)	0.044 (6)	−0.015 (6)	−0.017 (6)	0.034 (6)
C90	0.081 (7)	0.117 (8)	0.096 (7)	−0.031 (6)	−0.032 (6)	0.038 (6)
C91	0.087 (11)	0.255 (19)	0.174 (14)	−0.046 (12)	−0.041 (11)	0.161 (14)
C92	0.23 (2)	0.29 (2)	0.070 (11)	0.176 (18)	0.003 (13)	−0.020 (13)
C93	0.085 (8)	0.055 (6)	0.057 (6)	−0.001 (6)	−0.034 (6)	−0.037 (5)
C94	0.110 (10)	0.082 (8)	0.074 (8)	0.059 (8)	−0.040 (8)	−0.024 (7)
C95	0.152 (14)	0.065 (9)	0.108 (11)	0.011 (9)	−0.030 (11)	−0.005 (8)
C96	0.26 (2)	0.090 (11)	0.144 (14)	0.051 (13)	0.049 (15)	−0.040 (11)
P1	0.0351 (15)	0.0244 (13)	0.0355 (14)	−0.0097 (12)	−0.0041 (13)	0.0005 (11)
O1	0.066 (5)	0.029 (4)	0.054 (4)	−0.011 (3)	0.033 (4)	−0.006 (3)
O2	0.048 (4)	0.058 (4)	0.042 (4)	−0.023 (3)	−0.022 (3)	0.020 (3)
O3	0.050 (4)	0.038 (3)	0.036 (3)	−0.021 (3)	−0.022 (3)	0.014 (3)
O4	0.040 (4)	0.015 (3)	0.050 (4)	−0.007 (3)	0.003 (3)	−0.002 (3)
P2	0.0265 (14)	0.0259 (13)	0.0440 (15)	−0.0068 (11)	−0.0068 (12)	−0.0025 (12)
O5	0.073 (5)	0.082 (5)	0.054 (4)	−0.051 (4)	−0.040 (4)	0.021 (4)
O6	0.027 (4)	0.031 (3)	0.100 (5)	−0.002 (3)	0.002 (4)	−0.023 (4)
O7	0.028 (4)	0.031 (3)	0.062 (4)	−0.009 (3)	0.016 (3)	−0.015 (3)
O8	0.030 (3)	0.037 (3)	0.033 (3)	−0.014 (3)	−0.011 (3)	0.003 (3)
P3	0.0270 (14)	0.0228 (13)	0.0348 (14)	−0.0084 (11)	−0.0026 (12)	0.0000 (11)
O9	0.046 (4)	0.053 (4)	0.030 (3)	−0.017 (3)	−0.014 (3)	0.009 (3)
O10	0.046 (4)	0.031 (4)	0.057 (4)	−0.003 (3)	0.016 (4)	0.002 (3)
O11	0.040 (4)	0.015 (3)	0.048 (4)	−0.001 (3)	0.007 (3)	−0.001 (3)
O12	0.035 (4)	0.049 (4)	0.039 (4)	−0.020 (3)	−0.016 (3)	0.005 (3)
P4	0.0263 (14)	0.0293 (13)	0.0337 (14)	−0.0096 (12)	−0.0042 (12)	0.0023 (11)
O13	0.039 (4)	0.058 (4)	0.046 (4)	−0.025 (3)	−0.016 (3)	0.011 (3)
O14	0.025 (3)	0.044 (4)	0.027 (3)	−0.015 (3)	−0.001 (3)	0.003 (3)
O15	0.033 (4)	0.033 (3)	0.054 (4)	−0.002 (3)	0.004 (3)	−0.011 (3)
O16	0.031 (4)	0.027 (3)	0.068 (4)	−0.009 (3)	0.007 (3)	−0.011 (3)
P5	0.0366 (16)	0.0589 (18)	0.0601 (18)	−0.0238 (15)	−0.0208 (15)	0.0146 (15)
O17	0.047 (4)	0.041 (4)	0.072 (5)	−0.020 (3)	−0.011 (4)	−0.001 (3)
O18	0.024 (4)	0.082 (6)	0.160 (8)	0.006 (4)	0.021 (5)	−0.007 (6)
O19	0.062 (5)	0.094 (5)	0.046 (4)	−0.030 (4)	−0.024 (4)	0.018 (4)
O20	0.120 (6)	0.209 (8)	0.088 (5)	−0.133 (6)	−0.080 (5)	0.092 (5)
P6	0.0465 (17)	0.106 (2)	0.070 (2)	−0.0578 (17)	−0.0348 (16)	0.0417 (18)
O21	0.057 (4)	0.105 (5)	0.046 (4)	−0.053 (4)	−0.027 (4)	0.027 (4)
O22	0.118 (6)	0.158 (7)	0.088 (5)	−0.065 (5)	−0.039 (5)	0.030 (5)
O23	0.032 (5)	0.128 (8)	0.233 (11)	−0.014 (5)	0.045 (6)	0.080 (8)
O24	0.132 (7)	0.039 (4)	0.051 (4)	−0.033 (4)	0.011 (5)	−0.014 (3)
C97	0.107 (12)	0.269 (19)	0.067 (9)	0.076 (13)	−0.044 (8)	−0.064 (11)
Cl1	0.195 (4)	0.171 (4)	0.082 (2)	−0.050 (3)	−0.051 (3)	−0.017 (3)
Cl2	0.128 (3)	0.226 (4)	0.119 (3)	0.023 (3)	−0.038 (3)	−0.102 (3)
C98	0.058 (7)	0.075 (7)	0.033 (6)	−0.008 (6)	−0.016 (5)	0.000 (5)
Cl3	0.059 (2)	0.078 (2)	0.110 (2)	0.0012 (18)	0.0025 (19)	−0.0235 (19)
Cl4	0.094 (2)	0.095 (2)	0.0618 (18)	0.006 (2)	−0.0076 (18)	−0.0380 (17)
C99	0.149 (12)	0.152 (12)	0.182 (12)	0.086 (10)	−0.140 (10)	−0.092 (10)
Cl5	0.130 (3)	0.140 (3)	0.149 (3)	0.014 (3)	−0.075 (3)	−0.016 (3)
Cl6	0.129 (3)	0.149 (3)	0.159 (3)	0.051 (3)	−0.076 (3)	−0.083 (3)
C100	0.112 (10)	0.063 (8)	0.109 (10)	−0.003 (8)	−0.039 (9)	−0.032 (7)
Cl7	0.176 (4)	0.127 (3)	0.098 (3)	−0.035 (3)	−0.039 (3)	−0.018 (2)
Cl8	0.275 (5)	0.160 (4)	0.140 (3)	0.038 (4)	−0.104 (4)	−0.057 (3)
C101	0.070 (8)	0.060 (7)	0.051 (6)	−0.007 (6)	−0.030 (6)	0.007 (5)
Cl9	0.183 (4)	0.122 (3)	0.081 (2)	−0.058 (3)	−0.023 (3)	−0.023 (2)
Cl10	0.072 (2)	0.101 (2)	0.135 (3)	−0.016 (2)	−0.026 (2)	0.044 (2)
C102	0.056 (7)	0.082 (8)	0.046 (6)	−0.004 (6)	−0.025 (6)	−0.014 (6)
Cl11	0.074 (2)	0.096 (2)	0.109 (3)	0.002 (2)	0.002 (2)	−0.027 (2)
Cl12	0.0565 (18)	0.0666 (17)	0.0636 (18)	−0.0097 (15)	0.0024 (15)	−0.0223 (15)
C103	0.109 (9)	0.083 (8)	0.045 (6)	−0.018 (8)	−0.045 (7)	0.016 (6)
Cl13	0.090 (2)	0.074 (2)	0.089 (2)	0.0000 (19)	−0.0295 (19)	0.0091 (18)
Cl14	0.091 (3)	0.112 (3)	0.122 (3)	−0.010 (2)	−0.034 (2)	−0.029 (2)
C104	0.078 (11)	0.276 (19)	0.064 (8)	0.007 (12)	−0.016 (8)	−0.055 (11)
Cl15	0.106 (3)	0.171 (4)	0.154 (4)	−0.001 (3)	−0.013 (3)	−0.044 (3)
Cl16	0.195 (5)	0.484 (7)	0.265 (5)	0.099 (6)	−0.107 (4)	−0.252 (5)

Geometric parameters (Å, º) top

N1—C13	1.498 (9)	C65—C66	1.525 (10)
N1—C9	1.513 (8)	C66—C67	1.530 (11)
N1—C1	1.528 (9)	C67—C68	1.448 (13)
N1—C5	1.535 (9)	C69—C70	1.499 (9)
C1—C2	1.498 (9)	C70—C71	1.516 (10)
C2—C3	1.537 (9)	C71—C72	1.508 (10)
C3—C4	1.534 (10)	C73—C74	1.545 (10)
C5—C6	1.494 (10)	C74—C75	1.514 (11)
C6—C7	1.508 (11)	C75—C76	1.444 (11)
C7—C8	1.504 (10)	C77—C78	1.512 (10)
C9—C10	1.548 (11)	C78—C79	1.527 (10)
C10—C11	1.479 (11)	C79—C80	1.504 (11)
C11—C12	1.385 (13)	N6—C93	1.521 (9)
C13—C14	1.506 (10)	N6—C89	1.523 (8)
C14—C15	1.531 (10)	N6—C85	1.541 (9)
C15—C16	1.509 (11)	N6—C81	1.545 (9)
N2—C25	1.503 (8)	C81—C82	1.526 (9)
N2—C29	1.518 (9)	C82—C83	1.533 (11)
N2—C17	1.540 (8)	C83—C84	1.480 (11)
N2—C21	1.531 (9)	C85—C86	1.523 (10)
C17—C18	1.505 (10)	C86—C87	1.527 (10)
C18—C19	1.544 (10)	C87—C88	1.508 (11)
C19—C20	1.502 (10)	C89—C90	1.525 (11)
C21—C22	1.519 (10)	C90—C91	1.495 (12)
C22—C23	1.533 (10)	C91—C92	1.332 (14)
C23—C24	1.519 (11)	C93—C94	1.511 (11)
C25—C26	1.537 (9)	C94—C95	1.557 (12)
C26—C27	1.519 (9)	C95—C96	1.538 (13)
C27—C28	1.471 (10)	P1—O1	1.498 (5)
C29—C30	1.518 (10)	P1—O3	1.514 (5)
C30—C31	1.523 (11)	P1—O2	1.551 (6)
C31—C32	1.496 (11)	P1—O4	1.546 (5)
N3—C41	1.496 (9)	P2—O5	1.493 (6)
N3—C45	1.514 (8)	P2—O6	1.511 (6)
N3—C33	1.532 (9)	P2—O7	1.543 (5)
N3—C37	1.536 (8)	P2—O8	1.563 (5)
C33—C34	1.510 (10)	P3—O10	1.501 (5)
C34—C35	1.535 (10)	P3—O12	1.514 (5)
C35—C36	1.481 (10)	P3—O11	1.549 (5)
C37—C38	1.513 (9)	P3—O9	1.563 (6)
C38—C39	1.534 (9)	P4—O15	1.503 (5)
C39—C40	1.516 (10)	P4—O13	1.510 (5)
C41—C42	1.537 (9)	P4—O16	1.547 (5)
C42—C43	1.500 (10)	P4—O14	1.575 (5)
C43—C44	1.497 (10)	P5—O18	1.478 (7)
C45—C46	1.464 (10)	P5—O19	1.524 (6)
C46—C47	1.589 (12)	P5—O20	1.519 (7)
C47—C48	1.409 (14)	P5—O17	1.546 (6)
N4—C57	1.506 (8)	P6—O21	1.490 (6)
N4—C53	1.516 (8)	P6—O24	1.499 (7)
N4—C61	1.532 (9)	P6—O22	1.510 (7)
N4—C49	1.543 (8)	P6—O23	1.540 (8)
C49—C50	1.514 (10)	C97—Cl1	1.711 (7)
C50—C51	1.539 (10)	C97—Cl2	1.734 (8)
C51—C52	1.498 (11)	C98—Cl3	1.742 (9)
C53—C54	1.507 (10)	C98—Cl4	1.747 (8)
C54—C55	1.521 (10)	C99—Cl5	1.726 (10)
C55—C56	1.494 (10)	C99—Cl6	1.765 (11)
C57—C58	1.516 (9)	C100—Cl7	1.672 (10)
C58—C59	1.520 (10)	C100—Cl8	1.739 (9)
C59—C60	1.456 (11)	C101—Cl9	1.729 (9)
C61—C62	1.492 (10)	C101—Cl10	1.779 (9)
C62—C63	1.539 (11)	C102—Cl11	1.752 (9)
C63—C64	1.443 (12)	C102—Cl12	1.762 (9)
N5—C77	1.518 (9)	C103—Cl13	1.738 (9)
N5—C73	1.507 (9)	C103—Cl14	1.764 (9)
N5—C69	1.529 (8)	C104—Cl15	1.745 (11)
N5—C65	1.533 (8)	C104—Cl16	1.767 (11)

C13—N1—C9	111.2 (6)	C73—N5—C65	110.5 (6)
C13—N1—C1	112.4 (6)	C69—N5—C65	106.4 (5)
C9—N1—C1	106.4 (6)	C66—C65—N5	114.3 (6)
C13—N1—C5	108.4 (6)	C65—C66—C67	110.4 (8)
C9—N1—C5	109.1 (6)	C68—C67—C66	109.9 (9)
C1—N1—C5	109.3 (6)	C70—C69—N5	116.4 (6)
C2—C1—N1	114.0 (6)	C69—C70—C71	110.3 (7)
C1—C2—C3	110.5 (6)	C72—C71—C70	110.9 (7)
C4—C3—C2	112.2 (7)	N5—C73—C74	115.7 (7)
C6—C5—N1	117.3 (7)	C75—C74—C73	111.7 (8)
C5—C6—C7	113.6 (8)	C76—C75—C74	111.5 (8)
C6—C7—C8	114.6 (8)	C78—C77—N5	116.8 (7)
N1—C9—C10	115.9 (7)	C77—C78—C79	108.8 (7)
C11—C10—C9	113.2 (9)	C80—C79—C78	113.2 (8)
C12—C11—C10	115.9 (11)	C93—N6—C89	113.7 (7)
N1—C13—C14	118.8 (7)	C93—N6—C85	106.0 (6)
C13—C14—C15	111.1 (7)	C89—N6—C85	111.3 (6)
C16—C15—C14	112.5 (8)	C93—N6—C81	111.8 (6)
C25—N2—C29	110.7 (6)	C89—N6—C81	104.4 (6)
C25—N2—C17	107.2 (6)	C85—N6—C81	109.7 (6)
C29—N2—C17	109.9 (6)	C82—C81—N6	115.2 (7)
C25—N2—C21	112.0 (6)	C81—C82—C83	106.6 (7)
C29—N2—C21	105.8 (6)	C84—C83—C82	111.4 (9)
C17—N2—C21	111.5 (6)	C86—C85—N6	115.9 (7)
C18—C17—N2	115.0 (6)	C85—C86—C87	107.0 (7)
C17—C18—C19	109.8 (7)	C88—C87—C86	112.3 (8)
C20—C19—C18	112.8 (7)	C90—C89—N6	113.9 (7)
C22—C21—N2	115.5 (6)	C91—C90—C89	112.5 (10)
C21—C22—C23	109.4 (7)	C92—C91—C90	112.4 (12)
C24—C23—C22	111.6 (7)	C94—C93—N6	115.4 (7)
N2—C25—C26	117.2 (6)	C93—C94—C95	110.6 (9)
C27—C26—C25	110.7 (6)	C96—C95—C94	106.5 (10)
C28—C27—C26	112.7 (7)	O1—P1—O3	115.3 (4)
C30—C29—N2	116.9 (7)	O1—P1—O2	111.3 (4)
C29—C30—C31	111.1 (7)	O3—P1—O2	108.5 (3)
C32—C31—C30	114.3 (8)	O1—P1—O4	107.5 (3)
C41—N3—C45	110.6 (6)	O3—P1—O4	108.5 (3)
C41—N3—C33	106.9 (6)	O2—P1—O4	105.3 (3)
C45—N3—C33	109.8 (6)	O5—P2—O6	113.4 (4)
C41—N3—C37	111.6 (6)	O5—P2—O7	109.3 (4)
C45—N3—C37	107.6 (6)	O6—P2—O7	109.8 (3)
C33—N3—C37	110.3 (6)	O5—P2—O8	109.5 (3)
C34—C33—N3	115.5 (6)	O6—P2—O8	107.7 (3)
C33—C34—C35	111.0 (7)	O7—P2—O8	106.8 (3)
C36—C35—C34	112.9 (8)	O10—P3—O12	113.8 (4)
C38—C37—N3	115.0 (6)	O10—P3—O11	109.7 (3)
C37—C38—C39	109.8 (6)	O12—P3—O11	109.5 (3)
C40—C39—C38	110.3 (7)	O10—P3—O9	110.2 (4)
N3—C41—C42	118.2 (6)	O12—P3—O9	108.3 (3)
C43—C42—C41	110.4 (7)	O11—P3—O9	105.0 (3)
C44—C43—C42	112.9 (8)	O15—P4—O13	114.1 (4)
C46—C45—N3	117.7 (7)	O15—P4—O16	109.5 (3)
C45—C46—C47	110.1 (8)	O13—P4—O16	110.0 (3)
C48—C47—C46	113.8 (13)	O15—P4—O14	110.0 (3)
C57—N4—C53	107.5 (6)	O13—P4—O14	109.0 (3)
C57—N4—C61	111.6 (6)	O16—P4—O14	103.9 (3)
C53—N4—C61	111.4 (6)	O18—P5—O19	115.3 (5)
C57—N4—C49	111.3 (5)	O18—P5—O20	106.6 (5)
C53—N4—C49	111.2 (5)	O19—P5—O20	108.7 (4)
C61—N4—C49	103.9 (5)	O18—P5—O17	108.9 (4)
C50—C49—N4	114.8 (6)	O19—P5—O17	108.2 (4)
C49—C50—C51	107.9 (7)	O20—P5—O17	109.1 (4)
C52—C51—C50	111.8 (8)	O21—P6—O24	112.5 (4)
C54—C53—N4	116.7 (6)	O21—P6—O22	107.8 (4)
C53—C54—C55	108.4 (7)	O24—P6—O22	119.0 (5)
C56—C55—C54	114.0 (8)	O21—P6—O23	108.9 (5)
C58—C57—N4	117.9 (6)	O24—P6—O23	108.8 (4)
C57—C58—C59	111.3 (7)	O22—P6—O23	98.6 (5)
C60—C59—C58	112.3 (8)	Cl1—C97—Cl2	113.8 (5)
C62—C61—N4	116.1 (7)	Cl3—C98—Cl4	111.4 (5)
C61—C62—C63	107.2 (7)	Cl5—C99—Cl6	111.2 (7)
C64—C63—C62	112.4 (10)	Cl7—C100—Cl8	109.9 (6)
C77—N5—C73	106.6 (6)	Cl9—C101—Cl10	111.4 (5)
C77—N5—C69	111.8 (6)	Cl11—C102—Cl12	111.3 (5)
C73—N5—C69	111.3 (6)	Cl13—C103—Cl14	110.4 (5)
C77—N5—C65	110.3 (6)	Cl15—C104—Cl16	109.3 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H02···O5	0.84	1.70	2.505 (7)	160
O4—H04···O1ⁱ	0.84	1.66	2.478 (7)	165
O7—H07···O24	0.84	1.71	2.521 (7)	163
O8—H08···O3	0.84	1.71	2.527 (6)	164
O9—H09···O13	0.84	1.73	2.553 (6)	167
O11—H011···O10ⁱⁱ	0.84	1.70	2.518 (7)	165
O14—H014···O12	0.84	1.73	2.551 (6)	167
O16—H016···O18	0.84	1.77	2.529 (8)	150
O17—H017···O15	0.84	1.71	2.541 (6)	169
O20—H020···O21ⁱⁱⁱ	0.84	1.71	2.443 (9)	144
O22—H022···O19^iv	0.84	2.04	2.625 (11)	126
O23—H023···O6	0.84	1.70	2.448 (8)	148

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

Experimental details

Crystal data
Chemical formula	C_17.33H_40.67Cl_2.67NO₄P
M_r	452.68
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	16.1733 (3), 17.8443 (3), 26.7000 (5)
α, β, γ (°)	77.520 (3), 77.237 (3), 83.124 (3)
V (Å³)	7316.7 (2)
Z	12
Radiation type	Mo Kα
µ (mm⁻¹)	0.43
Crystal size (mm)	0.50 × 0.15 × 0.10

Data collection
Diffractometer	Nonius Kappa CCD Area-detector diffractometer
Absorption correction	Multi-scans (SORTAV; Blessing, 1997)
T_min, T_max	0.816, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	58198, 22291, 10322
R_int	0.100
θ_max (°)	24.1
(sin θ/λ)_max (Å⁻¹)	0.575

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.156, 0.393, 1.93
No. of reflections	22291
No. of parameters	1417
No. of restraints	878
H-atom treatment	H-atom parameters constrained
(Δ/σ)_max	2.834
Δρ_max, Δρ_min (e Å⁻³)	2.66, −1.47

Computer programs: COLLECT (Hooft, 1998), SCALEPACK (Otwinoski & Minor, 1997), COLLECT, DENZO (Otwinoski & Minor, 1997), COLLECT, maXus (Mackay et al., 1998), SHELXS 97 (Sheldrick, 1990), SHELXL 97 (Sheldrick, 1997), CAMERON (Watkin et al., 1993), WinGX (Farrugia, 1998).