trans-(2-Benzoyl­pyridine-κ²N,O)dichloro[2-(pyridine-2-carbon­yl)phenyl-κ²C¹,N]rhodium(III)

The title organometallic complex, trans-[Rh(C₁₂H₈NO)Cl₂(C₁₂H₉NO)], which was obtained from the reaction of rhodium(III) chloride and 2-benzoyl­pyridine, features an Rh^III atom coordinated by two N, one O, one C and two Cl atoms in a distorted octa­hedral environment.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.030
• wR factor = 0.090
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

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Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

trans-(2-Benzoylpyridine-κ²N,O)dichloro[2-(pyridine-2-carbonyl)phenyl- κ²C¹,N]rhodium(III)

Crystal data

[Rh(C12H8NO)Cl2(C12H9NO)]	F(000) = 1080
Mr = 539.21	Dx = 1.677 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.5492 (2) Å	Cell parameters from 18110 reflections
b = 8.2515 (1) Å	θ = 2.0–25.4°
c = 19.2229 (3) Å	µ = 1.08 mm^−1
β = 96.521 (1)°	T = 200 K
V = 2135.24 (5) Å^3	Prism, orange
Z = 4	0.45 × 0.24 × 0.08 mm

Data collection

Nonius KappaCCD area-detector diffractometer	3894 independent reflections
Radiation source: fine-focus sealed tube	3560 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
Detector resolution: 9 pixels mm^-1	θmax = 25.3°, θmin = 2.1°
CCD rotation images, thick slices scans	h = −16→16
Absorption correction: multi-scan (Blessing, 1995)	k = −9→9
Tmin = 0.729, Tmax = 0.918	l = −23→23
20293 measured reflections

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)] = 0.030	H-atom parameters constrained
wR(F^2) = 0.090	w = 1/[σ^2(Fo^2) + (0.0556P)^2 + 0.8456P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max = 0.002
3894 reflections	Δρmax = 0.90 e Å^−3
281 parameters	Δρmin = −1.18 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0129 (7)

Special details

Experimental. Rhodium(III) chloride trihydrate (0.132 g, 0.5 mmol) and 2-pyridyl phenone (0.549 g, 3.0 mmol) were placed in a ceramic boat (10 cm, 1.3 cm in length and in width, respectively) and heated in an oven at 150 °C for 15 h. After cooling, the resulting reaction mixture was washed with 20 ml of methanol and orange single crystals, (I), were isolated by suction filtration (yield 78%). Spectroscopic analysis: IR (KBr, cm^-1): ν(C═O) 1677, 1612; ¹H NMR (400 MHz, [(CD₃)₂SO], δ, p.p.m.): 9.53 (d, 1H, H(C24), J = 5.7 Hz), 8.77 (d, 1H, H(C1), J = 5.4 Hz), 8.42 (d, 1H, H(C4), J = 8.5 Hz), 8.35 (t, 1H, H(C3), J = 7.6 Hz), 8.31 (t, 1H, H(C22), J = 7.5 Hz), 8.24 (d, 1H, H(C21), J = 7.7 Hz), 8.15 (d, 2H, H(C8) + H(C12), J = 7.7 Hz), 8.05 (t, 1H, H(C2), J = 6.6 Hz), 7.94–7.89 (m, 2H, H(C23) + H(C10)), 7.80–7.75 (m, 4H, H(C17) + H(C9) + H(C11) + H(C14)), 7.46 (t, 1H, H(C16), J = 7.7 Hz), 7.29 (t, 1H, H(C15), J = 7.3 Hz); ¹³C NMR (500 MHz, [(CD₃)₂SO], δ, p.p.m.): 201.5, 187.7, 156.8, 156.5, 155.4, 155.3, 153.7, 153.5, 140.2, 140.0, 139.3, 135.1, 135.1, 133.6, 131.1, 130.8, 130.8, 130.7, 129.6, 128.4, 128.0, 127.5, 125.9, 124.1; analysis, calculated for C₂₄H₁₇Cl₂N₂O₂Rh: C 53.46, H 3.18, Cl 13.15, N 5.20%; found: C 53.41, H 3.32, Cl 13.29, N 5.35%.

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
Rh1	0.740042 (14)	0.23604 (2)	0.461802 (10)	0.01895 (12)
Cl1	0.61174 (5)	0.33261 (9)	0.38202 (3)	0.02823 (18)
Cl2	0.86288 (5)	0.15031 (9)	0.54994 (3)	0.02630 (18)
O1	0.68117 (13)	0.3691 (2)	0.55273 (9)	0.0247 (4)
O2	0.60440 (16)	−0.0616 (3)	0.28719 (11)	0.0434 (6)
N1	0.80511 (15)	0.4591 (3)	0.46074 (11)	0.0220 (5)
N2	0.66528 (15)	0.0243 (3)	0.46712 (11)	0.0224 (5)
C1	0.8453 (2)	0.5235 (4)	0.40658 (15)	0.0285 (6)
H1	0.8468	0.4633	0.3640	0.034*
C2	0.8867 (2)	0.6774 (4)	0.40994 (16)	0.0312 (7)
H2	0.9164	0.7197	0.3707	0.037*
C3	0.8846 (2)	0.7694 (3)	0.46909 (18)	0.0304 (7)
H3	0.9134	0.8758	0.4709	0.037*
C4	0.8397 (2)	0.7052 (4)	0.52485 (15)	0.0257 (6)
H4	0.8364	0.7679	0.5666	0.031*
C5	0.80109 (18)	0.5504 (3)	0.51934 (13)	0.0222 (6)
C6	0.74022 (18)	0.4777 (3)	0.57159 (14)	0.0229 (6)
C7	0.74851 (19)	0.5413 (3)	0.64403 (13)	0.0239 (6)
C8	0.8423 (2)	0.5700 (4)	0.68034 (15)	0.0325 (7)
H8	0.9004	0.5523	0.6570	0.039*
C9	0.8499 (2)	0.6200 (4)	0.74959 (16)	0.0406 (8)
H9	0.9144	0.6382	0.7745	0.049*
C10	0.7648 (3)	0.6459 (4)	0.78144 (16)	0.0407 (8)
H10	0.7698	0.6842	0.8289	0.049*
C11	0.6722 (2)	0.6177 (4)	0.74587 (16)	0.0376 (7)
H11	0.6133	0.6352	0.7683	0.045*
C12	0.6638 (2)	0.5620 (4)	0.67766 (15)	0.0293 (6)
H12	0.5998	0.5371	0.6532	0.035*
C13	0.81116 (19)	0.1367 (3)	0.38797 (13)	0.0230 (6)
C14	0.9120 (2)	0.1688 (4)	0.38579 (14)	0.0260 (6)
H14	0.9477	0.2334	0.4218	0.031*
C15	0.9612 (2)	0.1098 (4)	0.33145 (14)	0.0312 (7)
H15	1.0309	0.1300	0.3315	0.037*
C16	0.9104 (2)	0.0217 (4)	0.27779 (15)	0.0366 (7)
H16	0.9442	−0.0165	0.2397	0.044*
C17	0.8110 (2)	−0.0148 (4)	0.27968 (14)	0.0328 (7)
H17	0.7755	−0.0751	0.2421	0.039*
C18	0.76169 (19)	0.0406 (4)	0.33535 (14)	0.0261 (6)
C19	0.6599 (2)	−0.0225 (4)	0.33873 (15)	0.0297 (6)
C20	0.63119 (19)	−0.0646 (3)	0.40995 (15)	0.0266 (6)
C21	0.5744 (2)	−0.2037 (4)	0.41660 (18)	0.0352 (7)
H21	0.5540	−0.2682	0.3759	0.042*
C22	0.5500 (2)	−0.2497 (4)	0.4815 (2)	0.0384 (8)
H22	0.5094	−0.3438	0.4857	0.046*
C23	0.5835 (2)	−0.1564 (4)	0.53900 (17)	0.0348 (7)
H23	0.5675	−0.1850	0.5848	0.042*
C24	0.64091 (19)	−0.0209 (4)	0.53022 (15)	0.0280 (6)
H24	0.6638	0.0423	0.5708	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Rh1	0.02154 (16)	0.01741 (16)	0.01798 (16)	−0.00318 (7)	0.00263 (10)	0.00000 (7)
Cl1	0.0271 (3)	0.0305 (4)	0.0264 (4)	−0.0003 (3)	0.0001 (3)	0.0074 (3)
Cl2	0.0264 (3)	0.0292 (4)	0.0226 (3)	−0.0007 (3)	−0.0003 (3)	0.0003 (3)
O1	0.0254 (9)	0.0233 (11)	0.0260 (10)	−0.0048 (8)	0.0049 (8)	−0.0036 (8)
O2	0.0361 (11)	0.0561 (16)	0.0355 (12)	−0.0110 (11)	−0.0062 (9)	−0.0131 (11)
N1	0.0220 (10)	0.0217 (12)	0.0224 (11)	−0.0028 (9)	0.0026 (9)	0.0009 (9)
N2	0.0190 (10)	0.0202 (12)	0.0279 (12)	−0.0016 (9)	0.0028 (9)	0.0018 (9)
C1	0.0311 (14)	0.0287 (16)	0.0264 (14)	−0.0021 (12)	0.0061 (12)	0.0036 (12)
C2	0.0318 (15)	0.0258 (17)	0.0370 (16)	−0.0031 (13)	0.0080 (12)	0.0061 (13)
C3	0.0285 (16)	0.0201 (16)	0.0422 (18)	−0.0036 (11)	0.0021 (14)	0.0057 (12)
C4	0.0251 (14)	0.0213 (14)	0.0302 (15)	−0.0016 (11)	0.0004 (11)	−0.0036 (12)
C5	0.0222 (13)	0.0200 (14)	0.0239 (13)	−0.0011 (11)	0.0007 (10)	−0.0010 (11)
C6	0.0208 (12)	0.0213 (14)	0.0265 (14)	0.0026 (11)	0.0026 (10)	0.0002 (11)
C7	0.0285 (14)	0.0186 (14)	0.0248 (13)	−0.0002 (11)	0.0038 (11)	−0.0010 (11)
C8	0.0309 (15)	0.0337 (18)	0.0325 (15)	−0.0020 (13)	0.0020 (12)	−0.0027 (13)
C9	0.0444 (18)	0.044 (2)	0.0304 (16)	−0.0053 (15)	−0.0065 (14)	−0.0053 (14)
C10	0.064 (2)	0.0352 (19)	0.0225 (15)	−0.0033 (16)	0.0035 (14)	−0.0030 (13)
C11	0.0485 (18)	0.0351 (19)	0.0322 (16)	0.0023 (15)	0.0170 (14)	−0.0019 (13)
C12	0.0313 (14)	0.0262 (16)	0.0312 (15)	−0.0011 (12)	0.0070 (12)	0.0003 (12)
C13	0.0263 (13)	0.0245 (15)	0.0179 (13)	−0.0004 (11)	0.0012 (10)	0.0018 (11)
C14	0.0301 (14)	0.0247 (16)	0.0232 (13)	−0.0033 (12)	0.0028 (11)	−0.0006 (11)
C15	0.0277 (14)	0.0377 (18)	0.0291 (15)	−0.0018 (13)	0.0082 (12)	−0.0006 (13)
C16	0.0380 (16)	0.048 (2)	0.0245 (15)	0.0028 (14)	0.0085 (12)	−0.0082 (14)
C17	0.0368 (16)	0.0365 (18)	0.0248 (14)	−0.0006 (13)	0.0019 (12)	−0.0089 (13)
C18	0.0273 (14)	0.0274 (16)	0.0229 (13)	−0.0016 (12)	−0.0009 (11)	−0.0021 (11)
C19	0.0286 (14)	0.0277 (16)	0.0315 (15)	−0.0020 (12)	−0.0019 (12)	−0.0066 (12)
C20	0.0203 (12)	0.0215 (15)	0.0370 (15)	−0.0006 (11)	−0.0011 (11)	−0.0023 (12)
C21	0.0283 (15)	0.0233 (16)	0.053 (2)	−0.0046 (13)	−0.0011 (14)	−0.0061 (15)
C22	0.0247 (16)	0.0250 (18)	0.065 (2)	−0.0072 (11)	0.0016 (16)	0.0094 (14)
C23	0.0277 (14)	0.0305 (18)	0.0471 (18)	0.0024 (13)	0.0078 (13)	0.0169 (14)
C24	0.0248 (13)	0.0265 (16)	0.0327 (15)	0.0011 (11)	0.0039 (11)	0.0051 (12)

Geometric parameters (Å, º)

Rh1—Cl1	2.3246 (7)	C9—H9	0.9601
Rh1—Cl2	2.3454 (6)	C10—C11	1.378 (5)
Rh1—O1	2.2831 (18)	C10—H10	0.9599
Rh1—N1	2.042 (2)	C11—C12	1.382 (4)
Rh1—N2	2.028 (2)	C11—H11	0.9601
Rh1—C13	1.981 (3)	C12—H12	0.9600
O1—C6	1.229 (3)	C13—C14	1.397 (4)
O2—C19	1.217 (3)	C13—C18	1.396 (4)
N1—C1	1.339 (3)	C14—C15	1.389 (4)
N1—C5	1.361 (3)	C14—H14	0.9599
N2—C24	1.346 (4)	C15—C16	1.380 (4)
N2—C20	1.358 (3)	C15—H15	0.9600
C1—C2	1.387 (4)	C16—C17	1.385 (4)
C1—H1	0.9600	C16—H16	0.9600
C2—C3	1.370 (4)	C17—C18	1.401 (4)
C2—H2	0.9600	C17—H17	0.9600
C3—C4	1.396 (4)	C18—C19	1.482 (4)
C3—H3	0.9600	C19—C20	1.506 (4)
C4—C5	1.380 (4)	C20—C21	1.396 (4)
C4—H4	0.9600	C21—C22	1.380 (5)
C5—C6	1.496 (4)	C21—H21	0.9600
C6—C7	1.481 (4)	C22—C23	1.381 (5)
C7—C12	1.391 (4)	C22—H22	0.9600
C7—C8	1.399 (4)	C23—C24	1.383 (4)
C8—C9	1.387 (4)	C23—H23	0.9600
C8—H8	0.9600	C24—H24	0.9600
C9—C10	1.381 (5)
Cl1—Rh1—Cl2	175.00 (2)	C10—C11—H11	120.5
O1—Rh1—Cl1	92.30 (5)	C11—C10—C9	120.8 (3)
O1—Rh1—Cl2	82.70 (5)	C11—C10—H10	119.2
O1—C6—C7	120.9 (2)	C11—C12—C7	119.9 (3)
O1—C6—C5	119.0 (2)	C11—C12—H12	120.6
O2—C19—C18	123.3 (3)	C12—C7—C6	120.1 (2)
O2—C19—C20	118.7 (3)	C12—C7—C8	119.9 (2)
N1—Rh1—Cl1	88.61 (6)	C12—C11—H11	119.5
N1—Rh1—Cl2	90.42 (6)	C13—Rh1—Cl1	93.29 (7)
N1—Rh1—O1	76.29 (7)	C13—Rh1—Cl2	91.70 (7)
N1—C1—C2	121.7 (3)	C13—Rh1—O1	171.09 (8)
N1—C1—H1	120.5	C13—Rh1—N1	96.90 (10)
N1—C5—C4	121.7 (2)	C13—Rh1—N2	88.05 (10)
N1—C5—C6	114.2 (2)	C13—C14—H14	119.9
N2—Rh1—Cl1	89.32 (6)	C13—C18—C19	122.7 (2)
N2—Rh1—Cl2	91.22 (6)	C14—C13—C18	118.5 (2)
N2—Rh1—O1	98.96 (8)	C14—C13—Rh1	120.0 (2)
N2—Rh1—N1	174.74 (8)	C14—C15—H15	119.7
N2—C20—C19	120.8 (2)	C15—C14—C13	120.7 (3)
N2—C20—C21	120.7 (3)	C15—C14—H14	119.4
N2—C24—C23	122.2 (3)	C15—C16—C17	119.9 (3)
N2—C24—H24	119.5	C15—C16—H16	120.3
C1—N1—C5	118.8 (2)	C16—C15—C14	120.4 (3)
C1—N1—Rh1	125.45 (19)	C16—C15—H15	119.9
C1—C2—H2	120.0	C16—C17—C18	119.9 (3)
C2—C1—H1	117.8	C16—C17—H17	119.9
C2—C3—C4	118.6 (3)	C17—C16—H16	119.8
C2—C3—H3	119.4	C17—C18—C13	120.5 (2)
C3—C2—C1	119.9 (3)	C17—C18—C19	116.5 (2)
C3—C2—H2	120.0	C18—C17—H17	120.1
C3—C4—H4	120.2	C18—C13—Rh1	121.45 (19)
C4—C3—H3	122.0	C18—C19—C20	117.3 (2)
C4—C5—C6	123.6 (2)	C20—N2—Rh1	123.41 (18)
C5—N1—Rh1	115.64 (17)	C20—C21—H21	119.5
C5—C4—C3	119.1 (3)	C21—C20—C19	118.3 (3)
C5—C4—H4	120.6	C21—C22—H22	119.8
C6—O1—Rh1	107.72 (16)	C22—C21—C20	120.0 (3)
C7—C6—C5	120.0 (2)	C22—C21—H21	120.5
C7—C8—H8	119.2	C22—C23—H23	120.6
C7—C12—H12	119.6	C22—C23—C24	119.4 (3)
C8—C7—C6	119.8 (2)	C23—C22—C21	118.6 (3)
C8—C9—C10	119.8 (3)	C23—C22—H22	121.5
C8—C9—H9	119.3	C23—C24—H24	118.3
C9—C8—C7	119.5 (3)	C24—N2—C20	118.9 (2)
C9—C8—H8	121.2	C24—N2—C20	118.9 (2)
C9—C10—H10	120.0	C24—N2—Rh1	117.35 (19)
C10—C9—H9	120.9	C24—C23—H23	119.9
C10—C11—C12	120.0 (3)
Rh1—O1—C6—C5	28.0 (3)	C1—N1—C5—C4	−1.8 (4)
Rh1—O1—C6—C7	−154.6 (2)	C1—N1—C5—C6	170.4 (2)
Rh1—N1—C1—C2	179.0 (2)	C3—C4—C5—N1	−0.4 (4)
Rh1—N1—C5—C4	−178.2 (2)	C3—C4—C5—C6	−171.9 (3)
Rh1—N1—C5—C6	−6.0 (3)	N1—C5—C6—O1	−17.4 (3)
Rh1—N2—C20—C21	−175.6 (2)	C4—C5—C6—O1	154.7 (3)
Rh1—N2—C20—C19	8.8 (3)	N1—C5—C6—C7	165.2 (2)
Rh1—N2—C24—C23	175.0 (2)	C4—C5—C6—C7	−22.8 (4)
Rh1—C13—C14—C15	−175.2 (2)	O1—C6—C7—C12	−39.1 (4)
Rh1—C13—C18—C17	173.4 (2)	C5—C6—C7—C12	138.3 (3)
Rh1—C13—C18—C19	−13.3 (4)	O1—C6—C7—C8	136.5 (3)
O1—Rh1—N1—C1	−161.4 (2)	C5—C6—C7—C8	−46.2 (4)
O1—Rh1—N1—C5	14.67 (17)	C12—C7—C8—C9	−0.5 (5)
O1—Rh1—N2—C20	145.2 (2)	C6—C7—C8—C9	−176.0 (3)
O1—Rh1—N2—C24	−28.5 (2)	C7—C8—C9—C10	−1.9 (5)
N1—Rh1—O1—C6	−23.28 (17)	C8—C9—C10—C11	2.0 (5)
N1—Rh1—C13—C14	40.3 (2)	C9—C10—C11—C12	0.4 (5)
N1—Rh1—C13—C18	−136.5 (2)	C10—C11—C12—C7	−2.9 (5)
N2—Rh1—O1—C6	159.03 (17)	C8—C7—C12—C11	2.9 (4)
N2—Rh1—C13—C14	−141.5 (2)	C6—C7—C12—C11	178.4 (3)
N2—Rh1—C13—C18	41.7 (2)	C18—C13—C14—C15	1.7 (4)
Cl1—Rh1—N1—C1	−68.7 (2)	C13—C14—C15—C16	1.6 (5)
Cl1—Rh1—N1—C5	107.38 (17)	C14—C15—C16—C17	−3.0 (5)
Cl1—Rh1—N2—C20	53.0 (2)	C15—C16—C17—C18	1.3 (5)
Cl1—Rh1—N2—C24	−120.70 (19)	C14—C13—C18—C17	−3.4 (4)
Cl1—Rh1—O1—C6	−111.29 (17)	C14—C13—C18—C19	169.9 (3)
Cl1—Rh1—C13—C14	129.3 (2)	C16—C17—C18—C13	2.0 (5)
Cl1—Rh1—C13—C18	−47.5 (2)	C16—C17—C18—C19	−171.7 (3)
Cl2—Rh1—N2—C20	−132.0 (2)	C13—C18—C19—O2	156.5 (3)
Cl2—Rh1—N2—C24	54.32 (19)	C17—C18—C19—O2	−29.9 (4)
Cl2—Rh1—N1—C1	116.2 (2)	C13—C18—C19—C20	−33.5 (4)
Cl2—Rh1—N1—C5	−67.71 (17)	C17—C18—C19—C20	140.1 (3)
Cl2—Rh1—O1—C6	68.94 (16)	C24—N2—C20—C21	−2.0 (4)
Cl2—Rh1—C13—C14	−50.4 (2)	C24—N2—C20—C19	−177.5 (2)
Cl2—Rh1—C13—C18	132.8 (2)	O2—C19—C20—N2	−154.1 (3)
C13—Rh1—N1—C1	24.4 (2)	C18—C19—C20—N2	35.5 (4)
C13—Rh1—N1—C5	−159.48 (18)	O2—C19—C20—C21	30.3 (4)
C13—Rh1—N2—C20	−40.3 (2)	C18—C19—C20—C21	−140.1 (3)
C13—Rh1—N2—C24	146.0 (2)	N2—C20—C21—C22	1.9 (4)
C1—N1—C13—C14	53.9 (2)	C19—C20—C21—C22	177.5 (3)
C5—N1—C1—C2	3.0 (4)	C20—C21—C22—C23	−0.6 (5)
N1—C1—C2—C3	−1.9 (4)	C21—C22—C23—C24	−0.5 (4)
C1—C2—C3—C4	−0.4 (4)	C20—N2—C24—C23	1.0 (4)
C2—C3—C4—C5	1.5 (4)	C22—C23—C24—N2	0.3 (4)