Di-μ-hydroxo-bis{(aceto­nitrile)dibenzyl(6-methyl-2-pyridylmethyl)amine-κ²N,N]copper(II)} bis(perchlorate)

The title compound corresponds to a copper(II) dimer, [Cu₂(OH)₂(C₂H₃N)₂(C₂₁H₂₂N₂)₂](ClO₄)₂, where the metal centres are μ₂-bridged by hydroxo groups. The coordination of each copper(II) centre is a slightly distorted square-based pyramid, with two N atoms from dibenzyl(6-methyl-2-pyridylmethyl)amine (BiBzMePMA) and two hydroxo O atoms occupying the basal positions, and the aceto­nitrile N atom at the apical position. The dimer is centrosymmetric, with a crystallographic inversion centre midway between the two Cu atoms [Cu...Cu = 2.9522 (9) Å]

S1. Comment

The coordination chemistry of copper complexes is a subject of continuing importance, mainly in relation to the structure and reactivity of the active site in copper-containing metalloproteins. The reactivity of copper(I) complexes towards molecular oxygen is also relevant to the utilization of atmospheric oxygen in stoichiometric or catalytic oxidations of organic substrates mediated by copper complexes (Karlin et al., 1999), as well as to understanding the mechanism of dioxygen utilization by copper proteins (Karlin & Zuberbuhler, 1999; Kopf & Karlin, 2000; Solomon et al., 1996). Recent advances (Kitajima & Moro-oka, 1994; Suzuki et al., 2000) have shown that the structure and reactivity of copper(I) complexes are significantly modified by slight perturbations in the supporting ligands.

Recently, we reported that the oxygenation of a methanol solution of the copper(I) complex with the bidentate ligand dibenzyl-(6-methyl-2-pyridylmethyl)amine (BiBzMePMA) at room temperature leads to the bis-methoxo-bridged copper(II) complex [Cu(BiBzMePMA)]₂-µ₂(OCH₃)₂, which has been fully characterized, both magnetically and structurally (Rojas et al., 2004). Here, we report the crystal structure of the analogous bis-hydroxo-bridged compound, [Cu(BiBzMePMA)]₂-µ₂(OH)₂, (I), resulting from the same synthetic procedure, but in the presence of traces of water in the solvent.

The molecular structure of complex (I) is defined by two [CuL]²⁺ units [where L is dibenzyl-(6-methyl-2-pyridylmethyl)amine], µ₂-bridged by two hydroxyl groups, in such a way as to define a central N₂CuO₂CuN₂ core. Additionally, there is an acetonitrile (CH₃C≡N) molecule completing pentacoordination of each Cu atom, thus defining a slightly distorted square-based pyramidal coordination for the metal centres. The basal square of the pyramid is defined by two amine N atoms (N1 and N2) and two hydroxyl O atoms [O1 and O1ⁱ; symmetry code: (i) 1 - x, -y, 2 - z Please check added symmetry code], while the acetonitrile atom N3 occupies the apical position. This N atom deviates by 3.7° from the perpendicular to the basal-plane position.

The Cu—N_acetonitrile distance is 2.476 (5) Å, a rather long value for this kind of bond, which is usually in the range 2.00–2.50 Å. A shorter value of about 2 Å has been described for [Cu₂(L₂)(CH₃CN)₂]⁴⁺, where L is tetrakis(1-methylimidazol-2-ylmethyl)-2-hydroxy-1,3-diaminopropane (Gentschev et al., 2000), while a distance of 2.322 (6) Å has been described for [Cu₂(µ-oxalato)(dipyridylamino)₂(CH₃CN)₂](ClO₄)₂ (Du et al., 2003). The linear acetonitrile molecule defines an angle of 24.8° with the Cu—N3 line [Cu—N3—C22 155.2 (4)°], which can probably be ascribed to packing effects (Murthy et al., 2001).

The two edge-sharing pyramids have their apical acetonitrile N atoms lying on opposite sides of the CuO₂Cu plane, in a trans arrangement, as required by the inversion centre at the middle of the Cu···Cu distance. A cis arrangement was found in the macrocyclic complex [Cu₂L(CH₃C≡ N)₂], where L is 3,7,10,11,14,18,21,22-octaazatricyclo[18.2.2.2^9,12]-hexacosa- 1(22),2,7,9,11,13,18,20,23,25-decaene (Brooker et al., 1996).

The Cu···Cu distance is 2.9522 (9) Å, a rather short value for this kind of complex (Rojas et al., 2004). Consistently, the Cu—O—Cu angle is 100.24 (12)°. The atom sequence Cu—O1—Cuⁱ—O1ⁱ is a rather regular parallogram, with sides of about 1.92 Å. The Cu—O1 and Cu—O1ⁱ distances are 1.923 (3) and 1.920 (3) Å, respectively. The hydroxy H atoms deviate from the Cu–O plane by 45.5°, a value which can be affected by packing effects, i.e. interaction between the hydroxy H atoms and the O atoms of the perchlorate counteranion. The distances between atom H1 and the partially occupied perchlorate atoms O5A and O5B are 1.974 and 2.196 Å, respectively. The deviation of the hydroxy H atom from planarity has been described as an important factor which determines the magnetic coupling exchange of binuclear copper(II) complexes (Ruiz et al., 1997).

S2. Experimental

Cu(CH₃C≡N)₄(ClO₄) (1 mmol) was reacted with dibenzyl-(6-methyl-2-pyridylmethyl)amine (1 mmol) in moist methanol to give the copper(I) complex which, on reaction with oxygen, afforded the title dinuclear bis-hydroxo-bridged copper(II) complex. X-ray diffraction quality crystals of (I) were obtained by recrystallization from an acetonitrile–methanol mixture (Ratio?).

S3. Refinement

During the last stages of refinement, a certain disorder of the perchlorate O atoms was evident. This was modelled considering two partially occupied positions for the perchlorate anion, with occupancy factors of 0.60 and 0.40, respectively. All the Cl—O distances in each perchlorate position were set equal to common parameters, which were refined and finally set as 1.39 and 1.43 Å, respectively. The H atoms of the organic amine were introduced in calculated positions and then refined using the riding model, with C—H distances of 0.93 Å and with U_iso(H) = 1.2U_eq(C). The hydroxy H atom was located by difference synthesis during the last stages of the structure completion. Its coordinates were not subsequently refined.

Computing details

Data collection: SMART-NT (Bruker, 2001); data reduction: SAINT-NT (Bruker, 1999); program(s) used to solve structure: SHELXTL-NT (Bruker, 1999); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.

Figures

Fig. 1. The molecular structure of (I), showing part of the atom-numbering scheme. Displacement ellipsoids are plotted at the 33% probability level and hydroxy H atoms are shown as small spheres of arbitrary radii. The remaining H atoms and the perchlorate counteranion have been omitted for clarity. [Symmetry code: (i) 1 - x, -y, 2 - z.]

Di-µ-hydroxo-bis{(acetonitrile)[N-benzyl-N-(6-methyl-2- pyridylmethyl)benzylamine-κ²N',N'']copper(II)} diperchlorate

Crystal data

[Cu2(OH)2(C2H3N)2(C21H22N2)2](ClO4)2	F(000) = 1084
Mr = 1046.94	Dx = 1.462 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3378 reflections
a = 10.1453 (10) Å	θ = 4.6–46.7°
b = 20.0868 (19) Å	µ = 1.07 mm^−1
c = 12.0925 (12) Å	T = 571 K
β = 105.193 (2)°	Prism, blue
V = 2378.2 (4) Å^3	0.55 × 0.55 × 0.45 mm
Z = 2

Data collection

Siemens SMART CCD area-detector diffractometer	4218 independent reflections
Radiation source: fine-focus sealed tube	3006 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 25.1°, θmin = 2.0°
Absorption correction: part of the refinement model (ΔF) (SADABS in SAINT-NT; Bruker, 1999)	h = −11→12
Tmin = 0.572, Tmax = 0.618	k = −23→23
12077 measured reflections	l = −14→12

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)] = 0.057	Hydrogen site location: mixed
wR(F^2) = 0.183	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.1158P)^2] where P = (Fo^2 + 2Fc^2)/3
4218 reflections	(Δ/σ)max < 0.001
299 parameters	Δρmax = 0.76 e Å^−3
8 restraints	Δρmin = −0.74 e Å^−3

Special details

Experimental. Each frame was mesured during 10 s, using 0.3 /% between frames.

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	0.39369 (5)	−0.00309 (2)	0.89022 (4)	0.0369 (2)
O1	0.5473 (3)	0.05049 (14)	0.9675 (2)	0.0431 (7)
H1	0.6163	0.0577	0.9285	0.10 (2)*
N1	0.2476 (4)	−0.06543 (16)	0.7961 (3)	0.0402 (8)
C1	0.3294 (6)	−0.1707 (2)	0.8914 (5)	0.0691 (15)
H1A	0.4164	−0.1487	0.9096	0.104*
H1B	0.3387	−0.2145	0.8626	0.104*
H1C	0.2973	−0.1740	0.9591	0.104*
C2	0.2299 (5)	−0.1318 (2)	0.8028 (4)	0.0490 (11)
C3	0.1183 (6)	−0.1628 (3)	0.7287 (5)	0.0651 (15)
H3	0.1071	−0.2086	0.7333	0.078*
C4	0.0259 (6)	−0.1268 (3)	0.6500 (5)	0.0709 (16)
H4	−0.0502	−0.1474	0.6026	0.085*
C5	0.0461 (5)	−0.0597 (3)	0.6412 (4)	0.0596 (14)
H5	−0.0156	−0.0341	0.5874	0.072*
C6	0.1585 (4)	−0.0310 (2)	0.7130 (4)	0.0430 (11)
C7	0.1885 (4)	0.0415 (2)	0.7032 (4)	0.0437 (11)
H7A	0.1569	0.0550	0.6237	0.052*
H7B	0.1387	0.0672	0.7469	0.052*
N2	0.3366 (3)	0.05635 (16)	0.7457 (3)	0.0383 (8)
C8	0.4144 (5)	0.0414 (2)	0.6595 (4)	0.0508 (12)
H8A	0.5031	0.0629	0.6834	0.061*
H8B	0.3661	0.0606	0.5865	0.061*
C9	0.4352 (5)	−0.0315 (3)	0.6428 (4)	0.0531 (12)
C10	0.3506 (6)	−0.0668 (3)	0.5540 (5)	0.0709 (16)
H10	0.2838	−0.0451	0.4982	0.085*
C11	0.3674 (8)	−0.1363 (4)	0.5493 (7)	0.096 (2)
H11	0.3098	−0.1606	0.4908	0.116*
C12	0.4658 (9)	−0.1681 (4)	0.6285 (8)	0.098 (2)
H12	0.4736	−0.2142	0.6259	0.117*
C13	0.5538 (7)	−0.1326 (3)	0.7123 (6)	0.0837 (19)
H13	0.6249	−0.1542	0.7642	0.100*
C14	0.5378 (6)	−0.0651 (3)	0.7204 (5)	0.0640 (14)
H14	0.5971	−0.0416	0.7790	0.077*
C15	0.3537 (4)	0.12901 (19)	0.7795 (4)	0.0434 (11)
H15A	0.3144	0.1362	0.8435	0.052*
H15B	0.4505	0.1387	0.8058	0.052*
C16	0.2899 (4)	0.1773 (2)	0.6862 (4)	0.0437 (11)
C17	0.1583 (5)	0.2006 (2)	0.6742 (4)	0.0511 (12)
H17	0.1092	0.1866	0.7249	0.061*
C18	0.0996 (5)	0.2446 (2)	0.5868 (5)	0.0580 (14)
H18	0.0103	0.2589	0.5782	0.070*
C19	0.1712 (6)	0.2671 (2)	0.5136 (4)	0.0588 (14)
H19	0.1316	0.2971	0.4559	0.071*
C20	0.3018 (6)	0.2453 (2)	0.5256 (5)	0.0654 (15)
H20	0.3506	0.2601	0.4751	0.078*
C21	0.3619 (5)	0.2013 (2)	0.6121 (5)	0.0558 (13)
H21	0.4516	0.1877	0.6206	0.067*
N3	0.2201 (4)	0.0519 (2)	0.9695 (4)	0.0599 (11)
C22	0.1587 (5)	0.0594 (2)	1.0321 (5)	0.0540 (13)
C23	0.0792 (7)	0.0684 (3)	1.1156 (6)	0.0842 (19)
H23A	0.0011	0.0957	1.0830	0.126*
H23B	0.1348	0.0896	1.1829	0.126*
H23C	0.0495	0.0258	1.1359	0.126*
ClA	0.81252 (13)	0.12494 (7)	0.80005 (13)	0.0693 (5)	0.60
O2A	0.7094 (8)	0.1640 (4)	0.7324 (9)	0.116 (4)*	0.60
O3A	0.9310 (7)	0.1617 (5)	0.8419 (11)	0.143 (4)*	0.60
O4A	0.8574 (11)	0.0838 (5)	0.7248 (8)	0.147 (4)*	0.60
O5A	0.7786 (10)	0.0821 (5)	0.8762 (9)	0.114 (3)*	0.60
ClB	0.81252 (13)	0.12494 (7)	0.80005 (13)	0.0693 (5)	0.40
O2B	0.6926 (11)	0.1652 (8)	0.7825 (17)	0.141 (7)*	0.40
O3B	0.8673 (19)	0.1548 (9)	0.9098 (8)	0.168 (7)*	0.40
O4B	0.910 (2)	0.1394 (15)	0.737 (2)	0.237 (11)*	0.40
O5B	0.7293 (16)	0.0725 (8)	0.7984 (15)	0.131 (5)*	0.40

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.0420 (3)	0.0320 (3)	0.0337 (3)	−0.0029 (2)	0.0048 (2)	0.0042 (2)
O1	0.0433 (16)	0.0435 (18)	0.0391 (17)	−0.0092 (13)	0.0047 (14)	0.0085 (14)
N1	0.052 (2)	0.0341 (19)	0.037 (2)	−0.0056 (16)	0.0158 (17)	−0.0031 (16)
C1	0.097 (4)	0.035 (3)	0.074 (4)	0.000 (3)	0.020 (3)	−0.001 (3)
C2	0.068 (3)	0.034 (2)	0.050 (3)	−0.008 (2)	0.025 (2)	−0.007 (2)
C3	0.091 (4)	0.046 (3)	0.067 (4)	−0.023 (3)	0.035 (3)	−0.018 (3)
C4	0.083 (4)	0.061 (3)	0.062 (4)	−0.028 (3)	0.007 (3)	−0.018 (3)
C5	0.060 (3)	0.068 (3)	0.046 (3)	−0.017 (3)	0.004 (2)	−0.003 (3)
C6	0.050 (3)	0.042 (3)	0.035 (2)	−0.007 (2)	0.008 (2)	−0.005 (2)
C7	0.047 (2)	0.039 (2)	0.039 (2)	−0.0062 (19)	0.001 (2)	0.002 (2)
N2	0.048 (2)	0.0328 (18)	0.0327 (19)	−0.0032 (15)	0.0078 (15)	0.0013 (15)
C8	0.063 (3)	0.046 (3)	0.046 (3)	−0.001 (2)	0.019 (2)	0.007 (2)
C9	0.066 (3)	0.053 (3)	0.047 (3)	−0.001 (3)	0.028 (2)	−0.005 (2)
C10	0.092 (4)	0.072 (4)	0.052 (3)	−0.002 (3)	0.023 (3)	−0.013 (3)
C11	0.129 (6)	0.078 (5)	0.087 (5)	−0.006 (4)	0.038 (5)	−0.045 (4)
C12	0.127 (6)	0.065 (4)	0.116 (6)	0.021 (4)	0.059 (5)	−0.012 (4)
C13	0.084 (4)	0.065 (4)	0.103 (5)	0.020 (3)	0.027 (4)	−0.003 (4)
C14	0.066 (3)	0.062 (3)	0.066 (4)	0.012 (3)	0.020 (3)	−0.002 (3)
C15	0.052 (3)	0.032 (2)	0.042 (3)	−0.0047 (19)	0.006 (2)	0.0004 (19)
C16	0.055 (3)	0.031 (2)	0.043 (3)	−0.0048 (19)	0.010 (2)	0.0006 (19)
C17	0.058 (3)	0.047 (3)	0.053 (3)	0.005 (2)	0.024 (2)	0.000 (2)
C18	0.056 (3)	0.043 (3)	0.071 (4)	0.015 (2)	0.008 (3)	−0.001 (3)
C19	0.084 (4)	0.036 (3)	0.051 (3)	0.009 (2)	0.008 (3)	0.009 (2)
C20	0.084 (4)	0.051 (3)	0.068 (4)	0.003 (3)	0.032 (3)	0.023 (3)
C21	0.054 (3)	0.045 (3)	0.073 (3)	0.002 (2)	0.024 (3)	0.015 (3)
N3	0.066 (3)	0.059 (3)	0.060 (3)	0.008 (2)	0.027 (2)	0.008 (2)
C22	0.064 (3)	0.041 (3)	0.060 (3)	0.002 (2)	0.022 (3)	0.004 (2)
C23	0.099 (5)	0.080 (4)	0.092 (5)	0.002 (3)	0.060 (4)	−0.006 (3)
ClA	0.0505 (7)	0.0669 (9)	0.0814 (10)	−0.0146 (6)	0.0011 (6)	0.0250 (7)
ClB	0.0505 (7)	0.0669 (9)	0.0814 (10)	−0.0146 (6)	0.0011 (6)	0.0250 (7)

Geometric parameters (Å, º)

Cu—O1^i	1.920 (3)	C10—C11	1.408 (8)
Cu—O1	1.923 (3)	C10—H10	0.9300
Cu—N1	2.044 (3)	C11—C12	1.350 (10)
Cu—N2	2.070 (3)	C11—H11	0.9300
Cu—N3	2.476 (5)	C12—C13	1.362 (9)
Cu—Cu^i	2.9522 (9)	C12—H12	0.9300
O1—Cu^i	1.920 (3)	C13—C14	1.372 (8)
O1—H1	0.952	C13—H13	0.9300
N1—C2	1.350 (5)	C14—H14	0.9300
N1—C6	1.352 (5)	C15—C16	1.500 (6)
C1—C2	1.487 (7)	C15—H15A	0.9700
C1—H1A	0.9600	C15—H15B	0.9700
C1—H1B	0.9600	C16—C21	1.382 (6)
C1—H1C	0.9600	C16—C17	1.386 (6)
C2—C3	1.393 (7)	C17—C18	1.387 (7)
C3—C4	1.356 (8)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.361 (7)
C4—C5	1.373 (7)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.367 (7)
C5—C6	1.366 (6)	C19—H19	0.9300
C5—H5	0.9300	C20—C21	1.384 (6)
C6—C7	1.500 (6)	C20—H20	0.9300
C7—N2	1.485 (5)	C21—H21	0.9300
C7—H7A	0.9700	N3—C22	1.109 (6)
C7—H7B	0.9700	C22—C23	1.459 (8)
N2—C8	1.494 (6)	C23—H23A	0.9600
N2—C15	1.513 (5)	C23—H23B	0.9600
C8—C9	1.501 (7)	C23—H23C	0.9600
C8—H8A	0.9700	ClA—O5A	1.369 (10)
C8—H8B	0.9700	ClA—O3A	1.3890 (10)
C9—C14	1.381 (7)	ClA—O2A	1.3900 (7)
C9—C10	1.382 (7)	ClA—O4A	1.3911 (10)
O1^i—Cu—O1	79.61 (13)	C10—C9—C8	121.7 (5)
O1^i—Cu—N1	101.86 (13)	C9—C10—C11	118.9 (6)
O1—Cu—N1	172.23 (14)	C9—C10—H10	120.6
O1^i—Cu—N2	174.44 (12)	C11—C10—H10	120.6
O1—Cu—N2	95.69 (12)	C12—C11—C10	121.0 (6)
N1—Cu—N2	83.20 (14)	C12—C11—H11	119.5
O1^i—Cu—N3	87.74 (14)	C10—C11—H11	119.5
O1—Cu—N3	97.49 (14)	C11—C12—C13	119.9 (6)
N1—Cu—N3	90.21 (14)	C11—C12—H12	120.1
N2—Cu—N3	89.97 (14)	C13—C12—H12	120.1
Cu^i—O1—Cu	100.39 (13)	C12—C13—C14	120.2 (6)
Cu^i—O1—H1	115.0	C12—C13—H13	119.9
Cu—O1—H1	116.9	C14—C13—H13	119.9
C2—N1—C6	118.4 (4)	C13—C14—C9	121.1 (6)
C2—C1—H1A	109.5	C13—C14—H14	119.4
C2—C1—H1B	109.5	C9—C14—H14	119.4
H1A—C1—H1B	109.5	C16—C15—N2	115.1 (3)
C2—C1—H1C	109.5	C16—C15—H15A	108.5
H1A—C1—H1C	109.5	N2—C15—H15A	108.5
H1B—C1—H1C	109.5	C16—C15—H15B	108.5
N1—C2—C3	120.1 (5)	N2—C15—H15B	108.5
N1—C2—C1	119.1 (4)	H15A—C15—H15B	107.5
C3—C2—C1	120.8 (4)	C21—C16—C17	118.2 (4)
C4—C3—C2	120.6 (5)	C21—C16—C15	121.0 (4)
C4—C3—H3	119.7	C17—C16—C15	120.7 (4)
C2—C3—H3	119.7	C16—C17—C18	120.3 (5)
C3—C4—C5	119.2 (5)	C16—C17—H17	119.8
C3—C4—H4	120.4	C18—C17—H17	119.8
C5—C4—H4	120.4	C19—C18—C17	120.7 (5)
C6—C5—C4	118.8 (5)	C19—C18—H18	119.6
C6—C5—H5	120.6	C17—C18—H18	119.6
C4—C5—H5	120.6	C18—C19—C20	119.5 (5)
N1—C6—C5	122.8 (4)	C18—C19—H19	120.2
N1—C6—C7	116.4 (3)	C20—C19—H19	120.2
C5—C6—C7	120.8 (4)	C19—C20—C21	120.5 (5)
N2—C7—C6	112.1 (3)	C19—C20—H20	119.7
N2—C7—H7A	109.2	C21—C20—H20	119.7
C6—C7—H7A	109.2	C20—C21—C16	120.6 (5)
N2—C7—H7B	109.2	C20—C21—H21	119.7
C6—C7—H7B	109.2	C16—C21—H21	119.7
H7A—C7—H7B	107.9	C22—N3—Cu	155.2 (4)
C7—N2—C8	112.9 (3)	N3—C22—C23	179.2 (6)
C7—N2—C15	108.7 (3)	C22—C23—H23A	109.5
C8—N2—C15	109.7 (3)	C22—C23—H23B	109.5
C7—N2—Cu	102.1 (2)	H23A—C23—H23B	109.5
C8—N2—Cu	113.1 (3)	C22—C23—H23C	109.5
C15—N2—Cu	110.0 (2)	H23A—C23—H23C	109.5
N2—C8—C9	114.0 (4)	H23B—C23—H23C	109.5
N2—C8—H8A	108.7	O5A—ClA—O3A	115.8 (7)
C9—C8—H8A	108.7	O5A—ClA—O2A	117.9 (6)
N2—C8—H8B	108.7	O3A—ClA—O2A	111.1 (6)
C9—C8—H8B	108.7	O5A—ClA—O4A	104.5 (7)
H8A—C8—H8B	107.6	O3A—ClA—O4A	98.9 (7)
C14—C9—C10	118.7 (5)	O2A—ClA—O4A	106.0 (7)
C14—C9—C8	119.5 (4)

Symmetry code: (i) −x+1, −y, −z+2.