Di-μ-iodo-bis­{[N,N-bis­(diphenyl­phosphinometh­yl)-2-pyridinamine-κ²P,P′]copper(I)} dichloro­methane solvate

The title complex, [Cu₂I₂(C₃₁H₂₈N₂P₂)₂]·CH₂Cl₂, has a dimeric structure where two Cu^I atoms are doubly bridged by two I atoms. An inversion center is located midway between the two Cu atoms. The coordination geometry around the Cu atom is distorted tetra­hedral, formed by two P atoms from a bidentate N,N-bis­(diphenyl­phosphinometh­yl)-2-pyridinamine ligand and two iodine atoms. The complex has a metal–metal inter­action with a Cu...Cu distance of 3.068 (3) Å.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.008 Å
• Disorder in solvent or counterion
• R factor = 0.037
• wR factor = 0.095
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C16
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT410_ALERT_2_C Short Intra H...H Contact  H2A    ..  H4      ..       1.99 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      39.90 Deg.
              C32  -CL1  -C32     2.556   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      44.10 Deg.
              CL1  -CL2  -C32     2.556   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      38.00 Deg.
              C32  -CL2  -C32     2.556   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      31.60 Deg.
              CL2  -C32  -CL1     2.556   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      29.90 Deg.
              CL1  -C32  -CL2     2.556   1.555   1.555

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL (Bruker, 1998).

Di-µ-iodo-bis{[N,N-bis(diphenylphosphinomethyl)-2-pyridinamine- κ²P,P']copper(I)} dichloromethane solvate

Crystal data

[Cu2I2(C31H28N2P2)2]·CH2Cl2	Z = 1
Mr = 1446.79	F(000) = 722
Triclinic, P1	Dx = 1.583 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.510 (4) Å	Cell parameters from 3425 reflections
b = 11.879 (4) Å	θ = 2.4–27.4°
c = 12.935 (4) Å	µ = 1.95 mm^−1
α = 72.992 (4)°	T = 298 K
β = 81.788 (5)°	Block, colorless
γ = 81.119 (5)°	0.55 × 0.47 × 0.42 mm
V = 1517.6 (9) Å^3

Data collection

Bruker SMART APEX CCD diffractometer	5288 independent reflections
Radiation source: fine-focus sealed tube	4019 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→6
Tmin = 0.343, Tmax = 0.444	k = −13→14
7973 measured reflections	l = −15→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0366P)^2 + 0.656P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
5288 reflections	Δρmax = 0.64 e Å^−3
362 parameters	Δρmin = −0.59 e Å^−3
27 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0052 (6)

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)
Cu2	0.56363 (5)	0.47231 (4)	0.10564 (4)	0.03834 (16)
I1	0.31082 (3)	0.49507 (3)	0.08996 (2)	0.04650 (14)
Cl1	−0.0492 (10)	0.0809 (9)	0.5577 (8)	0.196 (3)	0.50
Cl2	−0.0337 (7)	−0.0784 (9)	0.4328 (8)	0.168 (3)	0.50
N1	0.6210 (3)	0.4696 (3)	0.3744 (3)	0.0382 (8)
N2	0.7623 (4)	0.3854 (3)	0.5077 (3)	0.0500 (10)
P1	0.63471 (10)	0.31553 (9)	0.24065 (9)	0.0360 (3)
P2	0.57302 (10)	0.62458 (9)	0.17552 (8)	0.0337 (3)
C1	0.6010 (4)	0.3512 (4)	0.3741 (3)	0.0400 (10)
H1A	0.5118	0.3397	0.4017	0.048*
H1B	0.6554	0.2942	0.4247	0.048*
C2	0.5264 (4)	0.5658 (4)	0.3238 (3)	0.0388 (10)
H2A	0.5190	0.6293	0.3582	0.047*
H2B	0.4424	0.5373	0.3350	0.047*
C3	0.7006 (4)	0.4852 (4)	0.4457 (3)	0.0386 (10)
C4	0.7169 (5)	0.5961 (4)	0.4525 (4)	0.0527 (12)
H4	0.6763	0.6643	0.4074	0.063*
C5	0.7936 (6)	0.6039 (5)	0.5265 (4)	0.0680 (15)
H5	0.8037	0.6778	0.5332	0.082*
C6	0.8559 (6)	0.5031 (6)	0.5910 (4)	0.0714 (16)
H6	0.9079	0.5070	0.6421	0.086*
C7	0.8385 (5)	0.3980 (5)	0.5774 (4)	0.0650 (15)
H7	0.8826	0.3297	0.6193	0.078*
C8	0.5683 (4)	0.1722 (4)	0.2883 (3)	0.0426 (10)
C9	0.4402 (5)	0.1714 (5)	0.2778 (4)	0.0629 (14)
H9	0.3913	0.2409	0.2432	0.076*
C10	0.3837 (7)	0.0669 (6)	0.3188 (5)	0.086 (2)
H10	0.2968	0.0668	0.3120	0.103*
C11	0.4556 (8)	−0.0363 (5)	0.3694 (5)	0.0814 (19)
H11	0.4178	−0.1063	0.3968	0.098*
C12	0.5816 (7)	−0.0354 (5)	0.3791 (5)	0.0726 (17)
H12	0.6303	−0.1053	0.4131	0.087*
C13	0.6392 (5)	0.0680 (4)	0.3393 (4)	0.0568 (13)
H13	0.7261	0.0672	0.3469	0.068*
C14	0.8084 (4)	0.2729 (4)	0.2220 (3)	0.0414 (10)
C15	0.8972 (5)	0.2993 (5)	0.2751 (5)	0.0618 (14)
H15	0.8690	0.3350	0.3307	0.074*
C16	1.0292 (5)	0.2744 (6)	0.2483 (6)	0.086 (2)
H16	1.0880	0.2951	0.2848	0.103*
C17	1.0727 (5)	0.2199 (5)	0.1692 (5)	0.0739 (17)
H17	1.1611	0.2024	0.1517	0.089*
C18	0.9853 (6)	0.1913 (6)	0.1158 (5)	0.0790 (18)
H18	1.0146	0.1521	0.0628	0.095*
C19	0.8544 (5)	0.2195 (5)	0.1390 (4)	0.0661 (15)
H19	0.7964	0.2029	0.0991	0.079*
C20	0.7247 (4)	0.6830 (4)	0.1727 (3)	0.0389 (10)
C21	0.8378 (4)	0.6140 (5)	0.1525 (4)	0.0562 (13)
H21	0.8354	0.5431	0.1363	0.067*
C22	0.9563 (5)	0.6512 (6)	0.1564 (5)	0.0806 (19)
H22	1.0332	0.6046	0.1436	0.097*
C23	0.9593 (6)	0.7562 (7)	0.1790 (5)	0.0805 (19)
H23	1.0384	0.7804	0.1822	0.097*
C24	0.8469 (6)	0.8257 (5)	0.1968 (4)	0.0694 (16)
H24	0.8495	0.8976	0.2110	0.083*
C25	0.7301 (5)	0.7896 (4)	0.1938 (4)	0.0504 (12)
H25	0.6538	0.8372	0.2061	0.060*
C26	0.4590 (4)	0.7567 (3)	0.1322 (3)	0.0371 (10)
C27	0.3608 (4)	0.7974 (4)	0.1997 (4)	0.0498 (12)
H27	0.3514	0.7580	0.2734	0.060*
C28	0.2748 (5)	0.8978 (4)	0.1576 (5)	0.0602 (14)
H28	0.2093	0.9255	0.2037	0.072*
C29	0.2872 (5)	0.9550 (4)	0.0493 (5)	0.0638 (15)
H29	0.2299	1.0215	0.0215	0.077*
C30	0.3836 (5)	0.9146 (5)	−0.0183 (4)	0.0672 (15)
H30	0.3922	0.9541	−0.0920	0.081*
C31	0.4685 (5)	0.8153 (4)	0.0221 (4)	0.0559 (13)
H31	0.5326	0.7875	−0.0250	0.067*
C32	0.0503 (19)	−0.017 (2)	0.504 (2)	0.196 (7)	0.50
H32	0.1178	0.0207	0.4568	0.235*	0.50
H33	0.0786	−0.0818	0.5625	0.235*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu2	0.0385 (3)	0.0402 (3)	0.0363 (3)	0.0004 (2)	−0.0053 (2)	−0.0126 (2)
I1	0.03115 (17)	0.0662 (2)	0.03980 (19)	−0.00239 (13)	0.00070 (12)	−0.01476 (15)
Cl1	0.237 (9)	0.187 (6)	0.165 (6)	−0.036 (8)	0.041 (6)	−0.074 (5)
Cl2	0.150 (6)	0.170 (5)	0.195 (6)	0.042 (5)	−0.089 (5)	−0.065 (4)
N1	0.049 (2)	0.0334 (19)	0.0302 (19)	0.0002 (16)	−0.0053 (16)	−0.0074 (15)
N2	0.051 (2)	0.057 (3)	0.039 (2)	0.0019 (19)	−0.0079 (18)	−0.0109 (19)
P1	0.0366 (6)	0.0343 (6)	0.0358 (6)	−0.0011 (5)	−0.0035 (5)	−0.0092 (5)
P2	0.0328 (6)	0.0340 (6)	0.0326 (6)	0.0011 (5)	−0.0032 (4)	−0.0091 (5)
C1	0.046 (2)	0.035 (2)	0.036 (2)	−0.0010 (19)	−0.0030 (19)	−0.0083 (19)
C2	0.040 (2)	0.040 (2)	0.035 (2)	−0.0017 (19)	0.0008 (18)	−0.0107 (19)
C3	0.041 (2)	0.047 (3)	0.027 (2)	−0.005 (2)	0.0030 (18)	−0.0112 (19)
C4	0.073 (3)	0.050 (3)	0.037 (3)	−0.013 (2)	−0.010 (2)	−0.010 (2)
C5	0.084 (4)	0.081 (4)	0.052 (3)	−0.027 (3)	−0.013 (3)	−0.026 (3)
C6	0.072 (4)	0.101 (5)	0.052 (3)	−0.023 (3)	−0.017 (3)	−0.026 (3)
C7	0.060 (3)	0.083 (4)	0.047 (3)	0.008 (3)	−0.016 (3)	−0.015 (3)
C8	0.050 (3)	0.040 (3)	0.040 (3)	−0.006 (2)	−0.004 (2)	−0.014 (2)
C9	0.069 (4)	0.050 (3)	0.066 (4)	−0.016 (3)	−0.017 (3)	−0.002 (3)
C10	0.097 (5)	0.075 (4)	0.092 (5)	−0.051 (4)	−0.021 (4)	−0.008 (4)
C11	0.125 (6)	0.056 (4)	0.070 (4)	−0.046 (4)	−0.006 (4)	−0.013 (3)
C12	0.116 (5)	0.035 (3)	0.063 (4)	−0.002 (3)	−0.016 (3)	−0.007 (3)
C13	0.071 (3)	0.037 (3)	0.061 (3)	−0.003 (2)	−0.014 (3)	−0.011 (2)
C14	0.044 (2)	0.037 (2)	0.037 (2)	0.000 (2)	−0.003 (2)	−0.0042 (19)
C15	0.048 (3)	0.067 (4)	0.077 (4)	0.001 (3)	−0.003 (3)	−0.036 (3)
C16	0.042 (3)	0.105 (5)	0.128 (6)	−0.004 (3)	−0.011 (3)	−0.061 (5)
C17	0.039 (3)	0.088 (4)	0.083 (4)	0.008 (3)	0.006 (3)	−0.019 (3)
C18	0.061 (4)	0.109 (5)	0.061 (4)	0.027 (3)	0.002 (3)	−0.037 (3)
C19	0.052 (3)	0.097 (4)	0.054 (3)	0.011 (3)	−0.010 (2)	−0.036 (3)
C20	0.036 (2)	0.044 (3)	0.033 (2)	−0.0044 (19)	−0.0051 (18)	−0.0038 (19)
C21	0.043 (3)	0.060 (3)	0.060 (3)	−0.002 (2)	−0.003 (2)	−0.011 (3)
C22	0.036 (3)	0.110 (5)	0.082 (4)	0.001 (3)	−0.003 (3)	−0.011 (4)
C23	0.061 (4)	0.112 (6)	0.064 (4)	−0.041 (4)	−0.018 (3)	0.004 (4)
C24	0.077 (4)	0.071 (4)	0.065 (4)	−0.031 (3)	−0.025 (3)	−0.007 (3)
C25	0.051 (3)	0.052 (3)	0.048 (3)	−0.009 (2)	−0.010 (2)	−0.009 (2)
C26	0.037 (2)	0.033 (2)	0.045 (3)	−0.0026 (18)	−0.0089 (19)	−0.014 (2)
C27	0.045 (3)	0.046 (3)	0.055 (3)	0.005 (2)	−0.004 (2)	−0.014 (2)
C28	0.045 (3)	0.057 (3)	0.079 (4)	0.014 (2)	−0.007 (3)	−0.030 (3)
C29	0.062 (3)	0.048 (3)	0.080 (4)	0.017 (3)	−0.030 (3)	−0.018 (3)
C30	0.082 (4)	0.058 (3)	0.052 (3)	0.018 (3)	−0.024 (3)	−0.007 (3)
C31	0.065 (3)	0.049 (3)	0.049 (3)	0.010 (2)	−0.007 (2)	−0.013 (2)
C32	0.195 (10)	0.198 (9)	0.199 (9)	−0.004 (8)	−0.026 (8)	−0.066 (7)

Geometric parameters (Å, º)

Cu2—P1	2.2620 (13)	C12—C13	1.382 (7)
Cu2—P2	2.2662 (13)	C12—H12	0.9300
Cu2—I1^i	2.6313 (9)	C13—H13	0.9300
Cu2—I1	2.6597 (10)	C14—C15	1.356 (7)
Cl1—Cl2^ii	0.892 (11)	C14—C19	1.394 (6)
Cl1—C32^ii	1.25 (2)	C15—C16	1.388 (7)
Cl1—C32	1.684 (16)	C15—H15	0.9300
Cl2—C32^ii	1.56 (2)	C16—C17	1.355 (8)
Cl2—C32	1.721 (17)	C16—H16	0.9300
N1—C3	1.397 (5)	C17—C18	1.360 (8)
N1—C1	1.455 (5)	C17—H17	0.9300
N1—C2	1.457 (5)	C18—C19	1.376 (7)
N2—C7	1.341 (6)	C18—H18	0.9300
N2—C3	1.351 (5)	C19—H19	0.9300
P1—C14	1.819 (4)	C20—C21	1.374 (6)
P1—C8	1.843 (4)	C20—C25	1.382 (6)
P1—C1	1.869 (4)	C21—C22	1.396 (7)
P2—C26	1.819 (4)	C21—H21	0.9300
P2—C20	1.826 (4)	C22—C23	1.367 (9)
P2—C2	1.860 (4)	C22—H22	0.9300
C1—H1A	0.9700	C23—C24	1.365 (8)
C1—H1B	0.9700	C23—H23	0.9300
C2—H2A	0.9700	C24—C25	1.370 (7)
C2—H2B	0.9700	C24—H24	0.9300
C3—C4	1.384 (6)	C25—H25	0.9300
C4—C5	1.367 (7)	C26—C27	1.378 (6)
C4—H4	0.9300	C26—C31	1.387 (6)
C5—C6	1.374 (8)	C27—C28	1.401 (6)
C5—H5	0.9300	C27—H27	0.9300
C6—C7	1.354 (7)	C28—C29	1.364 (7)
C6—H6	0.9300	C28—H28	0.9300
C7—H7	0.9300	C29—C30	1.366 (7)
C8—C9	1.374 (7)	C29—H29	0.9300
C8—C13	1.379 (6)	C30—C31	1.381 (7)
C9—C10	1.388 (7)	C30—H30	0.9300
C9—H9	0.9300	C31—H31	0.9300
C10—C11	1.375 (9)	C32—C32^ii	1.08 (4)
C10—H10	0.9300	C32—H32	0.9444
C11—C12	1.349 (9)	C32—H33	0.9520
C11—H11	0.9300
P1—Cu2—P2	101.06 (5)	C15—C14—P1	125.1 (4)
P1—Cu2—I1^i	118.65 (4)	C19—C14—P1	117.0 (4)
P2—Cu2—I1^i	111.47 (4)	C14—C15—C16	121.6 (5)
P1—Cu2—I1	114.38 (4)	C14—C15—H15	119.2
P2—Cu2—I1	100.28 (3)	C16—C15—H15	119.2
I1^i—Cu2—I1	109.13 (2)	C17—C16—C15	120.3 (6)
Cu2^i—I1—Cu2	70.87 (2)	C17—C16—H16	119.8
Cl2^ii—Cl1—C32^ii	106.0 (16)	C15—C16—H16	119.8
Cl2^ii—Cl1—C32	66.8 (13)	C16—C17—C18	119.1 (5)
C32^ii—Cl1—C32	39.9 (14)	C16—C17—H17	120.5
Cl1^ii—Cl2—C32^ii	81.6 (13)	C18—C17—H17	120.5
Cl1^ii—Cl2—C32	44.1 (12)	C17—C18—C19	121.1 (5)
C32^ii—Cl2—C32	38.0 (12)	C17—C18—H18	119.5
C3—N1—C1	120.6 (3)	C19—C18—H18	119.5
C3—N1—C2	120.8 (3)	C18—C19—C14	120.3 (5)
C1—N1—C2	116.0 (3)	C18—C19—H19	119.8
C7—N2—C3	117.3 (4)	C14—C19—H19	119.8
C14—P1—C8	103.3 (2)	C21—C20—C25	119.5 (4)
C14—P1—C1	106.3 (2)	C21—C20—P2	117.3 (4)
C8—P1—C1	95.80 (19)	C25—C20—P2	123.2 (3)
C14—P1—Cu2	112.98 (14)	C20—C21—C22	119.5 (5)
C8—P1—Cu2	125.43 (15)	C20—C21—H21	120.3
C1—P1—Cu2	110.56 (14)	C22—C21—H21	120.3
C26—P2—C20	103.83 (19)	C23—C22—C21	120.0 (5)
C26—P2—C2	104.85 (19)	C23—C22—H22	120.0
C20—P2—C2	102.32 (19)	C21—C22—H22	120.0
C26—P2—Cu2	116.81 (14)	C24—C23—C22	120.3 (5)
C20—P2—Cu2	122.20 (15)	C24—C23—H23	119.8
C2—P2—Cu2	104.68 (14)	C22—C23—H23	119.8
N1—C1—P1	116.8 (3)	C23—C24—C25	120.1 (6)
N1—C1—H1A	108.1	C23—C24—H24	120.0
P1—C1—H1A	108.1	C25—C24—H24	120.0
N1—C1—H1B	108.1	C24—C25—C20	120.6 (5)
P1—C1—H1B	108.1	C24—C25—H25	119.7
H1A—C1—H1B	107.3	C20—C25—H25	119.7
N1—C2—P2	111.6 (3)	C27—C26—C31	118.6 (4)
N1—C2—H2A	109.3	C27—C26—P2	124.5 (3)
P2—C2—H2A	109.3	C31—C26—P2	116.7 (3)
N1—C2—H2B	109.3	C26—C27—C28	120.2 (5)
P2—C2—H2B	109.3	C26—C27—H27	119.9
H2A—C2—H2B	108.0	C28—C27—H27	119.9
N2—C3—C4	121.4 (4)	C29—C28—C27	120.1 (5)
N2—C3—N1	116.2 (4)	C29—C28—H28	119.9
C4—C3—N1	122.4 (4)	C27—C28—H28	119.9
C5—C4—C3	118.9 (5)	C28—C29—C30	120.0 (5)
C5—C4—H4	120.6	C28—C29—H29	120.0
C3—C4—H4	120.6	C30—C29—H29	120.0
C4—C5—C6	120.4 (5)	C29—C30—C31	120.4 (5)
C4—C5—H5	119.8	C29—C30—H30	119.8
C6—C5—H5	119.8	C31—C30—H30	119.8
C7—C6—C5	117.3 (5)	C30—C31—C26	120.6 (5)
C7—C6—H6	121.3	C30—C31—H31	119.7
C5—C6—H6	121.3	C26—C31—H31	119.7
N2—C7—C6	124.6 (5)	C32^ii—C32—Cl1^ii	92 (2)
N2—C7—H7	117.7	C32^ii—C32—Cl2^ii	78.9 (19)
C6—C7—H7	117.7	Cl1^ii—C32—Cl2^ii	170 (2)
C9—C8—C13	119.1 (4)	C32^ii—C32—Cl1	47.7 (15)
C9—C8—P1	118.0 (3)	Cl1^ii—C32—Cl1	140.1 (14)
C13—C8—P1	122.9 (4)	Cl2^ii—C32—Cl1	31.6 (5)
C8—C9—C10	120.1 (5)	C32^ii—C32—Cl2	63.1 (18)
C8—C9—H9	120.0	Cl1^ii—C32—Cl2	29.9 (7)
C10—C9—H9	120.0	Cl2^ii—C32—Cl2	142.0 (12)
C11—C10—C9	120.2 (6)	Cl1—C32—Cl2	110.6 (10)
C11—C10—H10	119.9	C32^ii—C32—H32	121.8
C9—C10—H10	119.9	Cl1^ii—C32—H32	90.1
C12—C11—C10	119.6 (5)	Cl2^ii—C32—H32	89.6
C12—C11—H11	120.2	Cl1—C32—H32	109.7
C10—C11—H11	120.2	Cl2—C32—H32	109.7
C11—C12—C13	121.0 (5)	C32^ii—C32—H33	123.3
C11—C12—H12	119.5	Cl1^ii—C32—H33	94.3
C13—C12—H12	119.5	Cl2^ii—C32—H33	95.3
C8—C13—C12	120.1 (5)	Cl1—C32—H33	107.2
C8—C13—H13	119.9	Cl2—C32—H33	105.1
C12—C13—H13	119.9	H32—C32—H33	114.4
C15—C14—C19	117.5 (4)

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