{4,4',6,6'-Tetra-chloro-2,2'-[(spiro-[4.4]nonane-1,6-di-yl)bis-(nitrilo-methyl-idyne)]diphenolato-κO,N,N',O'}nickel(II).

The title compound, [Ni(C(23)H(20)Cl(4)N(2)O(2))], has an Ni(II) ion in a square-planar coordination formed by two imine N and two phenolato O atoms.

Related literature

For related literature, see: Gaetani Manfredotti et al. (1983 ▶), de Castro et al. (2001 ▶); Lutz (2003 ▶); Hoshina et al. (2000 ▶); Gosden et al. (1978 ▶, 1981 ▶); Healy & Pletcher (1980 ▶); Dahm & Peters (1996 ▶).

Experimental

Crystal data

[Ni(C23H20Cl4N2O2)]

M = 556.92

Monoclinic,

a = 13.344 (2) Å

b = 12.073 (2) Å

c = 14.081 (2) Å

β = 97.181 (3)°

V = 2250.6 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.36 mm−1

T = 294 (2) K

0.22 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.761, T max = 1.000 (expected range = 0.646–0.849)

20414 measured reflections

5196 independent reflections

3731 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.113

S = 1.01

5196 reflections

289 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.40 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808013792/im2062sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013792/im2062Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C23H20Cl4N2O2)]	F000 = 1136
Mr = 556.92	Dx = 1.644 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 10509 reflections
a = 13.344 (2) Å	θ = 1–27.5º
b = 12.073 (2) Å	µ = 1.36 mm−1
c = 14.081 (2) Å	T = 294 (2) K
β = 97.181 (3)º	Prism, black
V = 2250.6 (6) Å3	0.22 × 0.20 × 0.12 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	5196 independent reflections
Radiation source: fine-focus sealed tube	3731 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.055
T = 294(2) K	θmax = 27.6º
φ and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −17→17
Tmin = 0.761, Tmax = 1.000	k = −15→15
20414 measured reflections	l = −18→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.065P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
5196 reflections	Δρmax = 0.55 e Å−3
289 parameters	Δρmin = −0.39 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
Ni1	0.42863 (2)	0.43913 (3)	0.65679 (2)	0.02559 (11)
Cl1	0.10295 (6)	0.32950 (8)	0.53445 (7)	0.0554 (2)
Cl2	−0.05657 (6)	0.63477 (9)	0.75125 (8)	0.0661 (3)
Cl3	0.41217 (6)	0.10984 (6)	0.47916 (6)	0.0453 (2)
Cl4	0.78080 (7)	0.18824 (7)	0.37495 (7)	0.0568 (2)
O1	0.29376 (14)	0.39968 (17)	0.63812 (14)	0.0377 (5)
O2	0.43951 (13)	0.32517 (15)	0.57124 (13)	0.0327 (4)
N1	0.41147 (15)	0.52722 (18)	0.76468 (15)	0.0276 (5)
N2	0.55652 (15)	0.49892 (17)	0.64347 (15)	0.0267 (5)
C1	0.49859 (19)	0.5405 (2)	0.84037 (18)	0.0306 (6)
H1A	0.4785	0.5892	0.8904	0.037*
C2	0.5314 (2)	0.4293 (3)	0.8853 (2)	0.0416 (7)
H2A	0.5236	0.3704	0.8382	0.050*
H2B	0.4928	0.4110	0.9372	0.050*
C3	0.6429 (2)	0.4480 (3)	0.9227 (2)	0.0441 (8)
H3A	0.6505	0.4916	0.9810	0.053*
H3B	0.6786	0.3784	0.9344	0.053*
C4	0.6798 (2)	0.5111 (3)	0.8402 (2)	0.0410 (7)
H4A	0.6944	0.4605	0.7902	0.049*
H4B	0.7405	0.5526	0.8622	0.049*
C5	0.59263 (19)	0.5905 (2)	0.80250 (18)	0.0285 (6)
C6	0.58053 (19)	0.6042 (2)	0.69372 (18)	0.0274 (5)
H6A	0.5229	0.6537	0.6767	0.033*
C7	0.6754 (2)	0.6688 (2)	0.6779 (2)	0.0366 (6)
H7A	0.6677	0.7045	0.6157	0.044*
H7B	0.7343	0.6210	0.6833	0.044*
C8	0.6830 (2)	0.7548 (3)	0.7596 (2)	0.0480 (8)
H8A	0.6586	0.8264	0.7355	0.058*
H8B	0.7525	0.7627	0.7886	0.058*
C9	0.6165 (2)	0.7099 (3)	0.8331 (2)	0.0431 (7)
H9A	0.6526	0.7124	0.8973	0.052*
H9B	0.5549	0.7529	0.8317	0.052*
C10	0.32576 (19)	0.5653 (2)	0.78429 (19)	0.0295 (6)
H10A	0.3273	0.6123	0.8368	0.035*
C11	0.22883 (19)	0.5419 (2)	0.73250 (19)	0.0302 (6)
C12	0.21902 (19)	0.4569 (2)	0.66395 (19)	0.0304 (6)
C13	0.1189 (2)	0.4320 (2)	0.6213 (2)	0.0367 (6)
C14	0.0362 (2)	0.4869 (3)	0.6479 (2)	0.0421 (7)
H14A	−0.0285	0.4692	0.6193	0.051*
C15	0.0498 (2)	0.5684 (3)	0.7173 (2)	0.0397 (7)
C16	0.1439 (2)	0.5968 (2)	0.7601 (2)	0.0354 (6)
H16A	0.1517	0.6517	0.8068	0.043*
C17	0.6168 (2)	0.4638 (2)	0.58462 (18)	0.0290 (6)
H17A	0.6717	0.5085	0.5757	0.035*
C18	0.6061 (2)	0.3617 (2)	0.53205 (18)	0.0280 (6)
C19	0.51800 (19)	0.2961 (2)	0.53137 (18)	0.0278 (5)
C20	0.5172 (2)	0.1946 (2)	0.4804 (2)	0.0321 (6)
C21	0.5954 (2)	0.1621 (2)	0.4321 (2)	0.0355 (6)
H21A	0.5921	0.0955	0.3988	0.043*
C22	0.6801 (2)	0.2305 (2)	0.4335 (2)	0.0359 (6)
C23	0.6860 (2)	0.3287 (2)	0.48250 (19)	0.0324 (6)
H23A	0.7428	0.3734	0.4829	0.039*

	U11	U22	U33	U12	U13	U23
Ni1	0.02081 (18)	0.02942 (19)	0.02673 (19)	0.00060 (13)	0.00379 (13)	−0.00226 (14)
Cl1	0.0407 (4)	0.0607 (6)	0.0629 (5)	−0.0066 (4)	−0.0008 (4)	−0.0221 (4)
Cl2	0.0264 (4)	0.0838 (7)	0.0887 (7)	0.0125 (4)	0.0095 (4)	−0.0225 (6)
Cl3	0.0416 (4)	0.0319 (4)	0.0620 (5)	−0.0045 (3)	0.0044 (4)	−0.0038 (3)
Cl4	0.0631 (5)	0.0467 (5)	0.0688 (6)	0.0084 (4)	0.0402 (5)	−0.0077 (4)
O1	0.0227 (10)	0.0430 (11)	0.0477 (12)	−0.0003 (8)	0.0057 (8)	−0.0123 (9)
O2	0.0251 (9)	0.0325 (10)	0.0416 (11)	−0.0006 (8)	0.0077 (8)	−0.0089 (8)
N1	0.0216 (11)	0.0342 (12)	0.0274 (11)	−0.0005 (9)	0.0044 (9)	0.0002 (9)
N2	0.0244 (11)	0.0294 (12)	0.0262 (11)	0.0014 (9)	0.0030 (9)	0.0002 (9)
C1	0.0239 (13)	0.0420 (16)	0.0258 (13)	0.0021 (11)	0.0023 (10)	−0.0030 (11)
C2	0.0359 (16)	0.0485 (18)	0.0393 (17)	−0.0031 (13)	0.0006 (13)	0.0122 (14)
C3	0.0333 (16)	0.059 (2)	0.0385 (17)	0.0051 (14)	−0.0034 (13)	0.0139 (15)
C4	0.0268 (15)	0.0538 (19)	0.0418 (17)	0.0066 (13)	0.0012 (12)	0.0058 (15)
C5	0.0217 (12)	0.0345 (15)	0.0287 (14)	0.0004 (10)	0.0003 (10)	−0.0017 (11)
C6	0.0236 (13)	0.0274 (13)	0.0308 (14)	−0.0008 (10)	0.0020 (10)	−0.0008 (11)
C7	0.0332 (15)	0.0364 (16)	0.0406 (16)	−0.0072 (12)	0.0065 (12)	0.0014 (13)
C8	0.0472 (19)	0.0435 (18)	0.054 (2)	−0.0134 (15)	0.0088 (15)	−0.0082 (15)
C9	0.0445 (18)	0.0451 (18)	0.0392 (17)	−0.0112 (14)	0.0030 (13)	−0.0129 (14)
C10	0.0271 (13)	0.0315 (14)	0.0306 (14)	0.0006 (11)	0.0059 (11)	−0.0010 (11)
C11	0.0232 (13)	0.0360 (15)	0.0323 (14)	0.0008 (11)	0.0067 (11)	0.0031 (11)
C12	0.0239 (13)	0.0332 (15)	0.0350 (15)	−0.0011 (11)	0.0069 (11)	0.0024 (12)
C13	0.0312 (15)	0.0387 (16)	0.0393 (16)	−0.0040 (12)	0.0007 (12)	−0.0018 (13)
C14	0.0224 (14)	0.0531 (19)	0.0500 (18)	−0.0021 (13)	0.0015 (12)	−0.0004 (15)
C15	0.0233 (14)	0.0472 (18)	0.0493 (18)	0.0057 (12)	0.0077 (12)	0.0011 (14)
C16	0.0306 (15)	0.0394 (16)	0.0368 (16)	0.0069 (12)	0.0067 (12)	0.0010 (12)
C17	0.0269 (13)	0.0313 (14)	0.0292 (14)	−0.0031 (11)	0.0055 (11)	0.0014 (11)
C18	0.0301 (14)	0.0283 (14)	0.0259 (13)	0.0054 (11)	0.0043 (11)	0.0020 (11)
C19	0.0284 (13)	0.0278 (13)	0.0275 (13)	0.0039 (11)	0.0042 (11)	0.0019 (11)
C20	0.0324 (14)	0.0295 (14)	0.0339 (15)	0.0015 (11)	0.0017 (11)	0.0028 (11)
C21	0.0465 (17)	0.0272 (14)	0.0338 (15)	0.0060 (13)	0.0093 (13)	0.0000 (12)
C22	0.0398 (16)	0.0356 (16)	0.0348 (15)	0.0108 (13)	0.0146 (12)	0.0024 (12)
C23	0.0325 (15)	0.0343 (15)	0.0321 (15)	0.0014 (12)	0.0109 (12)	0.0052 (12)

Ni1—O2	1.8463 (18)	C6—H6A	0.9800
Ni1—O1	1.8484 (19)	C7—C8	1.544 (4)
Ni1—N2	1.884 (2)	C7—H7A	0.9700
Ni1—N1	1.892 (2)	C7—H7B	0.9700
Cl1—C13	1.734 (3)	C8—C9	1.544 (4)
Cl2—C15	1.747 (3)	C8—H8A	0.9700
Cl3—C20	1.733 (3)	C8—H8B	0.9700
Cl4—C22	1.739 (3)	C9—H9A	0.9700
O1—C12	1.302 (3)	C9—H9B	0.9700
O2—C19	1.297 (3)	C10—C11	1.432 (4)
N1—C10	1.294 (3)	C10—H10A	0.9300
N1—C1	1.484 (3)	C11—C12	1.403 (4)
N2—C17	1.296 (3)	C11—C16	1.409 (4)
N2—C6	1.470 (3)	C12—C13	1.426 (4)
C1—C2	1.525 (4)	C13—C14	1.379 (4)
C1—C5	1.546 (4)	C14—C15	1.383 (4)
C1—H1A	0.9800	C14—H14A	0.9300
C2—C3	1.532 (4)	C15—C16	1.366 (4)
C2—H2A	0.9700	C16—H16A	0.9300
C2—H2B	0.9700	C17—C18	1.436 (4)
C3—C4	1.522 (4)	C17—H17A	0.9300
C3—H3A	0.9700	C18—C23	1.403 (4)
C3—H3B	0.9700	C18—C19	1.416 (4)
C4—C5	1.548 (4)	C19—C20	1.420 (4)
C4—H4A	0.9700	C20—C21	1.372 (4)
C4—H4B	0.9700	C21—C22	1.397 (4)
C5—C9	1.527 (4)	C21—H21A	0.9300
C5—C6	1.529 (4)	C22—C23	1.368 (4)
C6—C7	1.526 (4)	C23—H23A	0.9300
O2—Ni1—O1	82.52 (8)	H7A—C7—H7B	109.2
O2—Ni1—N2	94.27 (8)	C7—C8—C9	105.9 (2)
O1—Ni1—N2	164.28 (9)	C7—C8—H8A	110.6
O2—Ni1—N1	165.98 (9)	C9—C8—H8A	110.6
O1—Ni1—N1	92.62 (9)	C7—C8—H8B	110.6
N2—Ni1—N1	93.82 (9)	C9—C8—H8B	110.6
C12—O1—Ni1	126.14 (18)	H8A—C8—H8B	108.7
C19—O2—Ni1	128.15 (17)	C5—C9—C8	105.0 (2)
C10—N1—C1	116.2 (2)	C5—C9—H9A	110.7
C10—N1—Ni1	124.76 (18)	C8—C9—H9A	110.7
C1—N1—Ni1	118.34 (16)	C5—C9—H9B	110.7
C17—N2—C6	118.3 (2)	C8—C9—H9B	110.7
C17—N2—Ni1	125.51 (19)	H9A—C9—H9B	108.8
C6—N2—Ni1	115.40 (15)	N1—C10—C11	126.0 (3)
N1—C1—C2	111.2 (2)	N1—C10—H10A	117.0
N1—C1—C5	113.0 (2)	C11—C10—H10A	117.0
C2—C1—C5	106.5 (2)	C12—C11—C16	121.6 (2)
N1—C1—H1A	108.7	C12—C11—C10	119.7 (2)
C2—C1—H1A	108.7	C16—C11—C10	118.2 (3)
C5—C1—H1A	108.7	O1—C12—C11	124.8 (2)
C1—C2—C3	103.2 (2)	O1—C12—C13	118.7 (2)
C1—C2—H2A	111.1	C11—C12—C13	116.5 (2)
C3—C2—H2A	111.1	C14—C13—C12	121.6 (3)
C1—C2—H2B	111.1	C14—C13—Cl1	120.2 (2)
C3—C2—H2B	111.1	C12—C13—Cl1	118.3 (2)
H2A—C2—H2B	109.1	C13—C14—C15	119.7 (3)
C4—C3—C2	101.8 (2)	C13—C14—H14A	120.2
C4—C3—H3A	111.4	C15—C14—H14A	120.2
C2—C3—H3A	111.4	C16—C15—C14	121.5 (3)
C4—C3—H3B	111.4	C16—C15—Cl2	119.8 (2)
C2—C3—H3B	111.4	C14—C15—Cl2	118.7 (2)
H3A—C3—H3B	109.3	C15—C16—C11	119.1 (3)
C3—C4—C5	105.7 (2)	C15—C16—H16A	120.4
C3—C4—H4A	110.6	C11—C16—H16A	120.4
C5—C4—H4A	110.6	N2—C17—C18	125.5 (2)
C3—C4—H4B	110.6	N2—C17—H17A	117.3
C5—C4—H4B	110.6	C18—C17—H17A	117.3
H4A—C4—H4B	108.7	C23—C18—C19	121.3 (2)
C9—C5—C6	99.9 (2)	C23—C18—C17	117.9 (2)
C9—C5—C1	114.9 (2)	C19—C18—C17	120.9 (2)
C6—C5—C1	113.5 (2)	O2—C19—C18	124.0 (2)
C9—C5—C4	111.5 (2)	O2—C19—C20	119.8 (2)
C6—C5—C4	113.0 (2)	C18—C19—C20	116.1 (2)
C1—C5—C4	104.4 (2)	C21—C20—C19	122.6 (3)
N2—C6—C7	120.4 (2)	C21—C20—Cl3	119.4 (2)
N2—C6—C5	112.2 (2)	C19—C20—Cl3	118.0 (2)
C7—C6—C5	102.5 (2)	C20—C21—C22	119.2 (3)
N2—C6—H6A	107.0	C20—C21—H21A	120.4
C7—C6—H6A	107.0	C22—C21—H21A	120.4
C5—C6—H6A	107.0	C23—C22—C21	121.0 (2)
C6—C7—C8	102.3 (2)	C23—C22—Cl4	119.6 (2)
C6—C7—H7A	111.3	C21—C22—Cl4	119.4 (2)
C8—C7—H7A	111.3	C22—C23—C18	119.8 (3)
C6—C7—H7B	111.3	C22—C23—H23A	120.1
C8—C7—H7B	111.3	C18—C23—H23A	120.1
O2—Ni1—O1—C12	−167.0 (2)	C6—C5—C9—C8	−37.3 (3)
N2—Ni1—O1—C12	−87.9 (4)	C1—C5—C9—C8	−159.1 (2)
N1—Ni1—O1—C12	26.2 (2)	C4—C5—C9—C8	82.4 (3)
O1—Ni1—O2—C19	172.9 (2)	C7—C8—C9—C5	12.0 (3)
N2—Ni1—O2—C19	8.3 (2)	C1—N1—C10—C11	−165.9 (3)
N1—Ni1—O2—C19	−116.8 (4)	Ni1—N1—C10—C11	4.6 (4)
O2—Ni1—N1—C10	−88.5 (4)	N1—C10—C11—C12	11.5 (4)
O1—Ni1—N1—C10	−19.3 (2)	N1—C10—C11—C16	−175.7 (3)
N2—Ni1—N1—C10	146.4 (2)	Ni1—O1—C12—C11	−18.5 (4)
O2—Ni1—N1—C1	81.9 (4)	Ni1—O1—C12—C13	162.3 (2)
O1—Ni1—N1—C1	151.08 (19)	C16—C11—C12—O1	−177.0 (3)
N2—Ni1—N1—C1	−43.26 (19)	C10—C11—C12—O1	−4.5 (4)
O2—Ni1—N2—C17	4.1 (2)	C16—C11—C12—C13	2.2 (4)
O1—Ni1—N2—C17	−73.4 (4)	C10—C11—C12—C13	174.7 (2)
N1—Ni1—N2—C17	172.7 (2)	O1—C12—C13—C14	177.7 (3)
O2—Ni1—N2—C6	174.05 (17)	C11—C12—C13—C14	−1.5 (4)
O1—Ni1—N2—C6	96.6 (4)	O1—C12—C13—Cl1	−2.0 (4)
N1—Ni1—N2—C6	−17.40 (18)	C11—C12—C13—Cl1	178.8 (2)
C10—N1—C1—C2	109.6 (3)	C12—C13—C14—C15	0.2 (5)
Ni1—N1—C1—C2	−61.6 (3)	Cl1—C13—C14—C15	179.9 (2)
C10—N1—C1—C5	−130.8 (2)	C13—C14—C15—C16	0.5 (5)
Ni1—N1—C1—C5	58.1 (3)	C13—C14—C15—Cl2	−178.8 (2)
N1—C1—C2—C3	154.6 (2)	C14—C15—C16—C11	0.2 (5)
C5—C1—C2—C3	31.1 (3)	Cl2—C15—C16—C11	179.5 (2)
C1—C2—C3—C4	−42.6 (3)	C12—C11—C16—C15	−1.6 (4)
C2—C3—C4—C5	38.5 (3)	C10—C11—C16—C15	−174.2 (3)
N1—C1—C5—C9	107.9 (3)	C6—N2—C17—C18	178.2 (2)
C2—C1—C5—C9	−129.7 (3)	Ni1—N2—C17—C18	−12.2 (4)
N1—C1—C5—C6	−6.2 (3)	N2—C17—C18—C23	−170.7 (2)
C2—C1—C5—C6	116.1 (3)	N2—C17—C18—C19	8.5 (4)
N1—C1—C5—C4	−129.7 (2)	Ni1—O2—C19—C18	−13.3 (4)
C2—C1—C5—C4	−7.4 (3)	Ni1—O2—C19—C20	169.04 (18)
C3—C4—C5—C9	105.1 (3)	C23—C18—C19—O2	−176.0 (2)
C3—C4—C5—C6	−143.2 (2)	C17—C18—C19—O2	4.8 (4)
C3—C4—C5—C1	−19.4 (3)	C23—C18—C19—C20	1.8 (4)
C17—N2—C6—C7	−1.1 (4)	C17—C18—C19—C20	−177.4 (2)
Ni1—N2—C6—C7	−171.80 (19)	O2—C19—C20—C21	176.2 (2)
C17—N2—C6—C5	−121.8 (2)	C18—C19—C20—C21	−1.7 (4)
Ni1—N2—C6—C5	67.5 (2)	O2—C19—C20—Cl3	−3.3 (3)
C9—C5—C6—N2	179.9 (2)	C18—C19—C20—Cl3	178.82 (19)
C1—C5—C6—N2	−57.2 (3)	C19—C20—C21—C22	0.7 (4)
C4—C5—C6—N2	61.4 (3)	Cl3—C20—C21—C22	−179.8 (2)
C9—C5—C6—C7	49.4 (3)	C20—C21—C22—C23	0.2 (4)
C1—C5—C6—C7	172.2 (2)	C20—C21—C22—Cl4	178.4 (2)
C4—C5—C6—C7	−69.2 (3)	C21—C22—C23—C18	−0.1 (4)
N2—C6—C7—C8	−167.4 (2)	Cl4—C22—C23—C18	−178.3 (2)
C5—C6—C7—C8	−42.0 (3)	C19—C18—C23—C22	−1.0 (4)
C6—C7—C8—C9	18.2 (3)	C17—C18—C23—C22	178.3 (2)