Tetra­kis(tert-butyl isocyanide)copper(I) chloride monohydrate

The title compound, [Cu(C₅H₉N)₄]Cl·H₂O, was obtained from the reaction of copper(II) chloride hydrate with KCN in the presence of two equivalents of tert-butyl­isocyanide. The reaction proceeds via the reduction of copper and the formation of (CN)₂. The compound shows a tetra­hedrally surrounded Cu^I centre, with the Cu^I ion and the water O atom being situated on crystallographic twofold axes. The crystal structure contains infinite chains of alternating solvent mol­ecules and Cl⁻ anions, with additional weak C—H...Cl or C—H...O inter­actions with the [Cu(CN^tBu)₄] cations.

Key indicators

• Single-crystal X-ray study
• T = 183 K
• Mean [sigma](N-C) = 0.006 Å
• Disorder in main residue
• R factor = 0.070
• wR factor = 0.231
• Data-to-parameter ratio = 26.1

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level A
PLAT432_ALERT_2_A Short Inter X...Y Contact  C3A    ..  C3A     ..       2.81 Ang.

Author Response: These short intermolecular contacts are due to the disorder of the tert. butyl groups. The same is true for all level B alerts.

PLAT432_ALERT_2_A Short Inter X...Y Contact  C10A   ..  C10A    ..       2.86 Ang.

Author Response: These short intermolecular contacts are due to the disorder of the tert. butyl groups. The same is true for all level B alerts.

PLAT726_ALERT_1_A H...A   Calc    11.23000, Rep     2.55000 Dev...       8.68 Ang.
              H14# -O1W     1.555   5.656
PLAT727_ALERT_1_A D...A   Calc    10.66(3), Rep     3.46700 Dev...       7.19 Ang.
              C9A  -O1W     1.555   5.656
PLAT728_ALERT_1_A D-H..A  Calc       53.00, Rep      156.00 Dev...     103.00 Deg.
              C9A  -H14# -O1W     1.555   1.555   5.656

Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          6
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.33 Ratio
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         C2
PLAT301_ALERT_3_B Main Residue  Disorder .........................      32.00 Perc.

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.108
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         16
PLAT746_ALERT_1_C H...A   Calc     2.39(6), Rep     2.38500 ......    Missing su
              H16# -CL1     1.555   8.635
PLAT747_ALERT_1_C D...A   Calc    3.264(2), Rep     3.26300 ......    Missing su
              O1W  -CL1     1.555   8.635
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      36.90 Deg.
              C3   -C2   -C5A     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      39.20 Deg.
              C10  -C7   -C8A     1.555   1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O

   5 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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S1. Comment

In connection with our studies of cyanide bridged coordination polymers, we recently reported the facile synthesis of cis- and trans-[Ru(CNtBu)₄(CN)₂] from Ru₃(CO)₁₂ and tert-butylisocyanide (Imhof & Dönnecke, 2003). Unfortunately, this reaction principle is limited to a small number of transition metal carbonyls. In order to enlarge our repertoire of cyano complexes which may be utilized in the synthesis of cyanide-bridged coordination polymers with a well defined steric arrangement of the metal centres with respect to each other, we are currently looking for a generalizable methodology to obtain trans-[M(CNR)₄(CN)₂] complexes.

The reaction of CuCl₂.xH₂O with tert-butylisocyanide in the presence of stoichiometric amounts of KCN leads to the almost quantitative formation of the title compound, (I), and the concomitant production of (CN)₂. The reduction of Cu^II in solutions containing cyanide ions is a well known phenomenon, which we unsuccessfully tried to avoid by adding the isocyanide before the corresponding amount of KCN.

The molecular structure of the [Cu(CN^tBu)₄] cation of (I) is presented in Fig. 1, and the most important bond lengths and angles are summarized in Table 1. The Cu^I atom and the water O atom are situated on a crystallographic twofold axis, resulting in a virtually ideal tetrahedral coordination sphere around the Cu^I ion. Bond lengths and angles are typical for tetrahedrally coordinated transition metal isocyanide complexes (Standard reference?). The isocyanide moieties show only a slight deviation from linearity. A search of the Cambridge Structural Database (CSD, Version 5.26, November 2004; Allen, 2002) found 36 structures in which a transition metal is surrounded by four isonitrile ligands. Most of these structurally characterized compounds are mononuclear complexes similar to (I) (Gordon et al., 1978; Spek, 1982; Matsubayashi et al., 1982; Plummer et al., 1984; Yamamoto & Yamazaki, 1984; Ashworth et al., 1984; Krause, 1979; Goldberg et al., 1976; Kanters et al., 1989; Bois et al., 1998; Connelly et al., 1992; Ojima et al., 1991; Leach et al., 1994; Deicas et al., 1997; Crossley & Orpen, 1995), but there are also reports of transition metal complexes of diisocyanides yielding either discrete dinuclear compounds (Mann 1981; Exstrom et al., 1996) or coordination polymers (Fortin et al., 1998). Three complexes are also copper(I) compounds, with methylisocyanide (Spek, 1982), 2-methoxyisobutylisocyanide or 2-methoxycarbonyl-2-methylethylisocyanide (Deicas et al., 1997) coordinating the central metal ion. The latter compounds also show a nearly undistorted tetrahedral ligand environment of the Cu atoms. The methylisocyanide derivative (Spek, 1982) with three independent molecules in the asymmetric unit of the unit cell shows Cu—C bond lengths from 1.941 to 2.014 Å, whereas the compounds published by Deicas et al. (1997) exhibit Cu—C bond lengths from 1.940 to 1.972 Å. Thus, the Cu—C bond lengths observed in the molecular structure of the title compound [1.952 (4) and 1.950 (4) Å] are in the same range as those reported previously. The same is true for the Cu—C—N bond angles, although values down to 169° have been observed earlier (Deicas et al., 1997), most probably due to steric interactions of the 2-methoxycarbonyl-2-methylethylisocyanide ligands, which are even bulkier than the tert-butyl groups of the title compound.

The crystal structure of the title compound is depicted in Fig. 2 and the shortest intermolecular contacts are presented in Table 2. Along the b axis of the unit cell, infinite chains consisting of Cl⁻ anions and solvent molecules are observed. These chains are held together by quite strong hydrogen bonds between the water H atoms and the Cl⁻ anions. In addition, the Cl⁻–water chains are connected by weak C—H···O and C—H···Cl contacts (Desiraju & Steiner, 1999) from methyl groups of the isocyanide ligands, building up an infinite three-dimensional network. In Fig. 2, only one plane of the network is shown for clarity.

S2. Experimental

CuCl₂.xH₂O (100 mg, 0.587 mmol) was dissolved in anhydrous ethanol (Volume?), resulting in a green solution. tert-Butylisocyanide (0.27 ml (2.348 mmol) was added to the solution using a syringe. After adding KCN (76 mg, 1.174 mmol), the colour of the solution slowly changed from green to colourless and a white precipitate of KCl was formed. The suspension was stirred for 4 h at room temperature. Filtration from the precipitated KCl and evaporation of the solvent in vacuo yielded a white solid. Recrystallization of the crude reaction product from acetone produced colourless prisms of (I) which were suitable for this X-ray diffraction study. Spectroscopic analysis: IR (KBr, cm⁻¹): ν(CH) 2984 (s), 2936 (m), ν(CN) 2177 (vs), δ(CH) 1467 (m), δ(CCH₃) 1395 (w), 1370 (s), 1240 (m), 1193 (s); MS (FAB in nitrobenzylalcohol, m/z, %): 413 {32, [Cu(CN^tBu)₄]H₂O}, 395 {10, [Cu(CN^tBu)₄]}, 330 {9, [Cu(CN^tBu)₃]H₂O}, 312 {62, [Cu(CN^tBu)₃]}, 229 {100, [Cu(CN^tBu)₂]}.

S3. Refinement

The water H atom was refined freely. All other H atoms were placed in idealized positions, with C—H = 0.98 Å [Please check added text], and were refined using a riding model, with U_iso(H) = 1.5U_eq(C). The C atoms of the disordered methyl groups were refined isotropically.

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1990); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular structure of the [Cu(CN^tBu)4]^+ cation of (I). Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. A packing diagram for (I).

tetrakis(tert-butylisocyanide)copper(I) chloride monohydrate

Crystal data

[Cu(C5H9N)4]Cl·H2O	F(000) = 960
Mr = 449.53	Dx = 1.064 Mg m^−3
Orthorhombic, Pcca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2a2ac	Cell parameters from 1947 reflections
a = 22.3933 (9) Å	θ = 1.8–27.5°
b = 5.6174 (2) Å	µ = 0.89 mm^−1
c = 22.3033 (8) Å	T = 183 K
V = 2805.58 (18) Å^3	Prism, colourless
Z = 4	0.05 × 0.05 × 0.03 mm

Data collection

Nonius KappaCCD area-detector diffractometer	1947 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.108
Graphite monochromator	θmax = 27.5°, θmin = 1.8°
ϕ and ω scans	h = −29→23
25405 measured reflections	k = −7→7
3233 independent reflections	l = −28→28

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.231	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.1248P)^2 + 3.6821P] where P = (Fo^2 + 2Fc^2)/3
3233 reflections	(Δ/σ)max = 0.004
124 parameters	Δρmax = 0.98 e Å^−3
0 restraints	Δρmin = −0.59 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	Occ. (<1)
Cu	0.5000	0.23848 (10)	0.7500	0.0265 (3)
Cl1	0.2500	1.0000	0.96677 (6)	0.0429 (4)
N1	0.41741 (16)	0.5455 (6)	0.83054 (15)	0.0427 (9)
N2	0.41861 (17)	−0.0642 (6)	0.66713 (16)	0.0446 (9)
C1	0.44895 (18)	0.4359 (7)	0.80045 (17)	0.0359 (9)
C2	0.3763 (2)	0.6776 (9)	0.8696 (2)	0.0481 (12)
C3	0.3484 (5)	0.5067 (18)	0.9118 (5)	0.075 (3)*	0.614 (9)
H3A	0.3744	0.4853	0.9468	0.112*	0.614 (9)
H3B	0.3427	0.3533	0.8917	0.112*	0.614 (9)
H3C	0.3096	0.5687	0.9250	0.112*	0.614 (9)
C4	0.3365 (5)	0.8233 (19)	0.8286 (4)	0.068 (3)*	0.614 (9)
H4A	0.3573	0.9694	0.8168	0.102*	0.614 (9)
H4B	0.2996	0.8645	0.8497	0.102*	0.614 (9)
H4C	0.3269	0.7301	0.7927	0.102*	0.614 (9)
C5	0.4146 (4)	0.8707 (16)	0.9049 (4)	0.063 (3)*	0.614 (9)
H5A	0.4568	0.8554	0.8937	0.094*	0.614 (9)
H5B	0.4103	0.8451	0.9482	0.094*	0.614 (9)
H5C	0.4004	1.0305	0.8946	0.094*	0.614 (9)
C3A	0.3111 (7)	0.555 (3)	0.8558 (8)	0.084 (6)*	0.386 (9)
H3AA	0.3162	0.4245	0.8269	0.125*	0.386 (9)
H3AB	0.2840	0.6743	0.8390	0.125*	0.386 (9)
H3AC	0.2943	0.4916	0.8931	0.125*	0.386 (9)
C4A	0.3803 (12)	0.894 (5)	0.8562 (12)	0.136 (10)*	0.386 (9)
H4AA	0.4202	0.9528	0.8667	0.204*	0.386 (9)
H4AB	0.3502	0.9848	0.8784	0.204*	0.386 (9)
H4AC	0.3737	0.9141	0.8131	0.204*	0.386 (9)
C5A	0.3831 (9)	0.566 (3)	0.9314 (8)	0.081 (5)*	0.386 (9)
H5AA	0.4208	0.6178	0.9494	0.122*	0.386 (9)
H5AB	0.3830	0.3921	0.9277	0.122*	0.386 (9)
H5AC	0.3498	0.6160	0.9570	0.122*	0.386 (9)
C6	0.44974 (18)	0.0415 (8)	0.69848 (17)	0.0370 (9)
C7	0.3778 (3)	−0.1888 (10)	0.6260 (2)	0.0581 (14)
C8	0.4173 (5)	−0.3892 (19)	0.5916 (5)	0.071 (3)*	0.548 (9)
H8A	0.4589	−0.3796	0.6051	0.107*	0.548 (9)
H8B	0.4155	−0.3615	0.5482	0.107*	0.548 (9)
H8C	0.4013	−0.5476	0.6007	0.107*	0.548 (9)
C9	0.3365 (6)	−0.340 (2)	0.6637 (5)	0.074 (3)*	0.548 (9)
H9A	0.3587	−0.4764	0.6799	0.112*	0.548 (9)
H9B	0.3035	−0.3980	0.6389	0.112*	0.548 (9)
H9C	0.3207	−0.2449	0.6969	0.112*	0.548 (9)
C10	0.3539 (6)	−0.020 (2)	0.5841 (6)	0.083 (4)*	0.548 (9)
H10A	0.3820	0.0016	0.5509	0.125*	0.548 (9)
H10B	0.3476	0.1330	0.6044	0.125*	0.548 (9)
H10C	0.3157	−0.0787	0.5686	0.125*	0.548 (9)
C8A	0.3897 (7)	−0.087 (3)	0.5636 (6)	0.077 (4)*	0.452 (9)
H8AA	0.4283	−0.1453	0.5489	0.116*	0.452 (9)
H8AB	0.3905	0.0873	0.5657	0.116*	0.452 (9)
H8AC	0.3580	−0.1376	0.5362	0.116*	0.452 (9)
C9A	0.3749 (11)	−0.421 (5)	0.6402 (11)	0.156 (10)*	0.452 (9)
H9AA	0.4139	−0.4956	0.6334	0.235*	0.452 (9)
H9AB	0.3448	−0.4994	0.6150	0.235*	0.452 (9)
H9AC	0.3638	−0.4383	0.6824	0.235*	0.452 (9)
C10A	0.3119 (5)	−0.061 (2)	0.6375 (6)	0.063 (4)*	0.452 (9)
H10D	0.3162	0.0658	0.6673	0.094*	0.452 (9)
H10E	0.2835	−0.1802	0.6521	0.094*	0.452 (9)
H10F	0.2972	0.0067	0.5998	0.094*	0.452 (9)
O1W	0.2500	−0.5000	0.5413 (2)	0.0594 (14)
H1OW	0.253 (3)	−0.622 (12)	0.516 (2)	0.10 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.0238 (4)	0.0328 (4)	0.0227 (4)	0.000	0.0005 (3)	0.000
Cl1	0.0560 (9)	0.0347 (7)	0.0380 (8)	0.0129 (7)	0.000	0.000
N1	0.047 (2)	0.042 (2)	0.0393 (19)	0.0037 (17)	0.0140 (17)	0.0003 (16)
N2	0.052 (2)	0.042 (2)	0.040 (2)	−0.0077 (18)	−0.0189 (18)	0.0000 (16)
C1	0.035 (2)	0.043 (2)	0.030 (2)	0.0038 (18)	0.0055 (17)	0.0007 (17)
C2	0.051 (3)	0.048 (3)	0.045 (3)	0.015 (2)	0.024 (2)	0.000 (2)
C6	0.036 (2)	0.044 (2)	0.031 (2)	−0.0032 (19)	−0.0022 (17)	0.0030 (18)
C7	0.071 (4)	0.054 (3)	0.049 (3)	−0.019 (3)	−0.028 (3)	−0.002 (3)
O1W	0.095 (4)	0.044 (3)	0.039 (3)	−0.022 (3)	0.000	0.000

Geometric parameters (Å, º)

Cu—C1	1.950 (4)	C5A—H5AA	0.9800
Cu—C1^i	1.950 (4)	C5A—H5AB	0.9800
Cu—C6^i	1.952 (4)	C5A—H5AC	0.9800
Cu—C6	1.952 (4)	C7—C9A	1.35 (2)
N1—C1	1.152 (5)	C7—C10	1.435 (13)
N1—C2	1.468 (5)	C7—C9	1.513 (13)
N2—C6	1.152 (5)	C7—C8A	1.528 (15)
N2—C7	1.472 (6)	C7—C8	1.624 (12)
C2—C4A	1.26 (3)	C7—C10A	1.661 (13)
C2—C3	1.484 (11)	C8—H8A	0.9800
C2—C4	1.518 (11)	C8—H8B	0.9800
C2—C5A	1.522 (17)	C8—H8C	0.9800
C2—C5	1.591 (10)	C9—H9A	0.9800
C2—C3A	1.646 (17)	C9—H9B	0.9800
C3—H3A	0.9800	C9—H9C	0.9800
C3—H3B	0.9800	C10—H10A	0.9800
C3—H3C	0.9800	C10—H10B	0.9800
C4—H4A	0.9800	C10—H10C	0.9800
C4—H4B	0.9800	C8A—H8AA	0.9800
C4—H4C	0.9800	C8A—H8AB	0.9800
C5—H5A	0.9800	C8A—H8AC	0.9800
C5—H5B	0.9800	C9A—H9AA	0.9800
C5—H5C	0.9800	C9A—H9AB	0.9800
C3A—H3AA	0.9800	C9A—H9AC	0.9800
C3A—H3AB	0.9800	C10A—H10D	0.9800
C3A—H3AC	0.9800	C10A—H10E	0.9800
C4A—H4AA	0.9800	C10A—H10F	0.9800
C4A—H4AB	0.9800	O1W—H1OW	0.90 (6)
C4A—H4AC	0.9800
C1—Cu—C1^i	110.7 (2)	H5AA—C5A—H5AB	109.5
C1—Cu—C6^i	108.71 (18)	C2—C5A—H5AC	109.5
C1^i—Cu—C6^i	108.90 (19)	H5AA—C5A—H5AC	109.5
C1—Cu—C6	108.90 (19)	H5AB—C5A—H5AC	109.5
C1^i—Cu—C6	108.71 (18)	N2—C6—Cu	176.5 (4)
C6^i—Cu—C6	110.9 (2)	C9A—C7—C10	140.9 (12)
C1—N1—C2	178.1 (4)	C9A—C7—N2	110.2 (11)
C6—N2—C7	177.4 (5)	C10—C7—N2	108.9 (6)
N1—C1—Cu	177.5 (4)	C9A—C7—C9	45.0 (11)
C4A—C2—N1	107.7 (12)	C10—C7—C9	120.4 (8)
C4A—C2—C3	143.9 (13)	N2—C7—C9	107.4 (6)
N1—C2—C3	108.3 (5)	C9A—C7—C8A	125.9 (13)
C4A—C2—C4	51.4 (12)	C10—C7—C8A	39.2 (7)
N1—C2—C4	106.4 (5)	N2—C7—C8A	106.3 (7)
C3—C2—C4	118.9 (7)	C9—C7—C8A	145.5 (8)
C4A—C2—C5A	127.4 (15)	C9A—C7—C8	57.6 (12)
N1—C2—C5A	105.5 (8)	C10—C7—C8	110.8 (8)
C3—C2—C5A	36.9 (7)	N2—C7—C8	106.7 (5)
C4—C2—C5A	145.8 (9)	C9—C7—C8	101.8 (7)
C4A—C2—C5	54.5 (13)	C8A—C7—C8	74.6 (8)
N1—C2—C5	107.5 (5)	C9A—C7—C10A	109.9 (13)
C3—C2—C5	110.7 (6)	C10—C7—C10A	58.8 (7)
C4—C2—C5	104.3 (6)	N2—C7—C10A	104.4 (6)
C5A—C2—C5	77.3 (9)	C9—C7—C10A	67.3 (7)
C4A—C2—C3A	115.2 (14)	C8A—C7—C10A	97.7 (8)
N1—C2—C3A	103.4 (7)	C8—C7—C10A	148.9 (6)
C3—C2—C3A	58.2 (8)	C7—C8—H8A	109.5
C4—C2—C3A	65.9 (8)	C7—C8—H8B	109.5
C5A—C2—C3A	94.9 (10)	H8A—C8—H8B	109.5
C5—C2—C3A	149.1 (7)	C7—C8—H8C	109.5
C2—C3—H3A	109.5	H8A—C8—H8C	109.5
C2—C3—H3B	109.5	H8B—C8—H8C	109.5
H3A—C3—H3B	109.5	C7—C9—H9A	109.5
C2—C3—H3C	109.5	C7—C9—H9B	109.5
H3A—C3—H3C	109.5	H9A—C9—H9B	109.5
H3B—C3—H3C	109.5	C7—C9—H9C	109.5
C2—C4—H4A	109.5	H9A—C9—H9C	109.5
C2—C4—H4B	109.5	H9B—C9—H9C	109.5
H4A—C4—H4B	109.5	C7—C10—H10A	109.5
C2—C4—H4C	109.5	C7—C10—H10B	109.5
H4A—C4—H4C	109.5	H10A—C10—H10B	109.5
H4B—C4—H4C	109.5	C7—C10—H10C	109.5
C2—C5—H5A	109.5	H10A—C10—H10C	109.5
C2—C5—H5B	109.5	H10B—C10—H10C	109.5
H5A—C5—H5B	109.5	C7—C8A—H8AA	109.5
C2—C5—H5C	109.5	C7—C8A—H8AB	109.5
H5A—C5—H5C	109.5	H8AA—C8A—H8AB	109.5
H5B—C5—H5C	109.5	C7—C8A—H8AC	109.5
C2—C3A—H3AA	109.5	H8AA—C8A—H8AC	109.5
C2—C3A—H3AB	109.5	H8AB—C8A—H8AC	109.5
H3AA—C3A—H3AB	109.5	C7—C9A—H9AA	109.5
C2—C3A—H3AC	109.5	C7—C9A—H9AB	109.5
H3AA—C3A—H3AC	109.5	H9AA—C9A—H9AB	109.5
H3AB—C3A—H3AC	109.5	C7—C9A—H9AC	109.5
C2—C4A—H4AA	109.5	H9AA—C9A—H9AC	109.5
C2—C4A—H4AB	109.5	H9AB—C9A—H9AC	109.5
H4AA—C4A—H4AB	109.5	C7—C10A—H10D	109.5
C2—C4A—H4AC	109.5	C7—C10A—H10E	109.5
H4AA—C4A—H4AC	109.5	H10D—C10A—H10E	109.5
H4AB—C4A—H4AC	109.5	C7—C10A—H10F	109.5
C2—C5A—H5AA	109.5	H10D—C10A—H10F	109.5
C2—C5A—H5AB	109.5	H10E—C10A—H10F	109.5

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	H···A	D···A	D—H···A
C9A—H9AB···O1W^ii	2.55	3.467	156
C10—H10C···Cl1^iii	2.74	3.503	135
O1W—H1OW···Cl1^iv	2.385	3.263	166

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