5-(4-Chloro­phenyl)-3-oxa-4-aza­tri­cyclo­[5.2.1.0^2,6]­dec-4-ene

The asymmetric unit of the title compound, C₁₄H₁₄ClNO, contains two crystallographically independent mol­ecules related by a pseudo-inversion centre at (1.00, 0.65, 0.25). The isoxazoline rings of these two mol­ecules are planar and the structure analysis confirms the exo-orientation of the isoxazole ring to norbornane. The two mol­ecules in the asymmetric unit differ in the conformation of the chloro­phenyl rings.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.144
• Data-to-parameter ratio = 15.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: MolEN (Fair,1990); data reduction: MolEN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997).

(I)

Crystal data

C14H14ClNO	Dx = 1.348 Mg m^−3
Mr = 247.73	Melting point: 361 K
Monoclinic, P21/n	Cu Kα radiation, λ = 1.5418 Å
a = 11.782 (4) Å	Cell parameters from 25 reflections
b = 10.288 (3) Å	θ = 7–32°
c = 20.461 (3) Å	µ = 2.62 mm^−1
β = 100.20 (2)°	T = 298 K
V = 2440.9 (11) Å^3	Tiny block, colourless
Z = 8	0.2 × 0.12 × 0.1 mm
F(000) = 1040

Data collection

Enraf-Nonius CAD-4 diffractometer	θmax = 69.9°, θmin = 4.1°
ω–2θ scans	h = 0→14
4716 measured reflections	k = 0→12
4622 independent reflections	l = −24→24
3767 reflections with I > 2σ(I)	3 standard reflections every 100 reflections
Rint = 0.038	intensity decay: none

Refinement

Refinement on F^2	H-atom parameters not refined
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0849P)^2 + 0.537P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.047	(Δ/σ)max < 0.001
wR(F^2) = 0.144	Δρmax = 0.30 e Å^−3
S = 1.05	Δρmin = −0.38 e Å^−3
4622 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
308 parameters	Extinction coefficient: 0.0027 (3)
0 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.87573 (6)	0.18028 (7)	0.06041 (3)	0.0799 (2)
C1A	1.15819 (17)	0.6428 (2)	0.42491 (9)	0.0535 (5)
H1A	1.2312	0.686	0.4428	0.064*
C2A	1.16427 (16)	0.4950 (2)	0.42390 (9)	0.0524 (5)
H2A	1.1612	0.4574	0.4676	0.063*
O3A	1.26383 (11)	0.44902 (18)	0.39747 (7)	0.0682 (4)
N4A	1.22713 (14)	0.38859 (19)	0.33543 (9)	0.0613 (4)
C5A	1.11702 (15)	0.39068 (18)	0.32094 (9)	0.0476 (4)
C6A	1.05861 (15)	0.45587 (17)	0.37161 (8)	0.0446 (4)
H6A	1.0058	0.3978	0.3896	0.054*
C7A	1.00338 (15)	0.58780 (17)	0.34935 (9)	0.0459 (4)
H7A	0.9515	0.5865	0.3062	0.055*
C8A	0.95014 (17)	0.6434 (2)	0.40661 (10)	0.0574 (5)
H8A1	0.903	0.5791	0.4239	0.069*
H8A2	0.9034	0.7194	0.3925	0.069*
C9A	1.05741 (18)	0.6798 (2)	0.45907 (10)	0.0609 (5)
H9A1	1.0584	0.772	0.4692	0.073*
H9A2	1.0594	0.6308	0.4997	0.073*
C10A	1.11013 (17)	0.67396 (19)	0.35214 (9)	0.0523 (4)
H10A	1.1603	0.6452	0.3222	0.063*
H10B	1.0911	0.7652	0.3448	0.063*
C51A	1.05794 (16)	0.33754 (17)	0.25742 (9)	0.0469 (4)
C52A	1.11838 (17)	0.3077 (2)	0.20646 (10)	0.0585 (5)
H52A	1.1977	0.3209	0.2132	0.07*
C53A	1.06363 (19)	0.2594 (2)	0.14688 (10)	0.0643 (5)
H53A	1.1052	0.2404	0.1134	0.077*
C54A	0.94515 (18)	0.2391 (2)	0.13680 (10)	0.0555 (5)
C55A	0.88366 (17)	0.26549 (19)	0.18622 (11)	0.0569 (5)
H55A	0.8046	0.2505	0.1794	0.068*
C56A	0.93989 (16)	0.31461 (18)	0.24636 (10)	0.0525 (4)
H56A	0.898	0.3325	0.2798	0.063*
Cl2	1.15826 (6)	1.11364 (7)	0.45644 (3)	0.0858 (2)
C1B	0.83131 (17)	0.6838 (2)	0.08491 (11)	0.0594 (5)
H1B	0.7548	0.6503	0.0656	0.071*
C2B	0.83813 (16)	0.8308 (2)	0.09176 (10)	0.0554 (5)
H2B	0.8438	0.8728	0.0495	0.066*
O3B	0.74377 (12)	0.88295 (17)	0.12025 (9)	0.0735 (5)
N4B	0.78645 (14)	0.93644 (19)	0.18343 (10)	0.0669 (5)
C5B	0.89632 (15)	0.92208 (17)	0.19698 (10)	0.0485 (4)
C6B	0.94730 (14)	0.85366 (18)	0.14431 (8)	0.0457 (4)
H6B	1.005	0.9066	0.1274	0.055*
C7B	0.98968 (16)	0.71445 (19)	0.16209 (9)	0.0504 (4)
H7B	1.041	0.7061	0.2051	0.06*
C8B	1.03821 (19)	0.6589 (2)	0.10317 (11)	0.0660 (6)
H8B1	1.0776	0.5771	0.1147	0.079*
H8B2	1.0913	0.7194	0.0881	0.079*
C9B	0.92884 (19)	0.6392 (3)	0.04953 (11)	0.0704 (6)
H9B1	0.9319	0.692	0.0106	0.084*
H9B2	0.9195	0.5488	0.0363	0.084*
C10B	0.87574 (19)	0.6409 (2)	0.15656 (11)	0.0617 (5)
H10C	0.8282	0.6721	0.1874	0.074*
H10D	0.8861	0.5475	0.1609	0.074*
C51B	0.95988 (15)	0.96878 (17)	0.26066 (9)	0.0468 (4)
C52B	0.90520 (17)	0.9903 (2)	0.31505 (11)	0.0598 (5)
H52B	0.8264	0.975	0.3106	0.072*
C53B	0.9650 (2)	1.0333 (2)	0.37471 (11)	0.0655 (5)
H53B	0.9276	1.0456	0.4106	0.079*
C54B	1.08210 (18)	1.05827 (19)	0.38092 (10)	0.0560 (5)
C55B	1.13855 (17)	1.03884 (19)	0.32838 (10)	0.0536 (4)
H55B	1.217	1.0562	0.333	0.064*
C56B	1.07809 (15)	0.99349 (17)	0.26885 (9)	0.0469 (4)
H56B	1.1167	0.9791	0.2336	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0890 (4)	0.0842 (4)	0.0601 (3)	−0.0167 (3)	−0.0045 (3)	0.0004 (3)
C1A	0.0493 (10)	0.0671 (12)	0.0410 (9)	−0.0107 (9)	−0.0002 (7)	0.0007 (8)
C2A	0.0469 (10)	0.0706 (12)	0.0390 (8)	0.0064 (9)	0.0059 (7)	0.0127 (8)
O3A	0.0430 (7)	0.1011 (12)	0.0568 (8)	0.0150 (7)	−0.0010 (6)	−0.0025 (8)
N4A	0.0442 (9)	0.0828 (12)	0.0559 (9)	0.0102 (8)	0.0061 (7)	0.0009 (8)
C5A	0.0422 (9)	0.0510 (10)	0.0507 (10)	0.0059 (7)	0.0110 (7)	0.0103 (8)
C6A	0.0431 (9)	0.0471 (9)	0.0444 (9)	−0.0006 (7)	0.0097 (7)	0.0080 (7)
C7A	0.0433 (9)	0.0477 (9)	0.0441 (9)	0.0022 (7)	0.0006 (7)	0.0051 (7)
C8A	0.0515 (11)	0.0594 (11)	0.0611 (11)	0.0044 (9)	0.0094 (9)	−0.0055 (9)
C9A	0.0671 (13)	0.0684 (13)	0.0460 (10)	0.0031 (10)	0.0066 (9)	−0.0037 (9)
C10A	0.0583 (11)	0.0518 (10)	0.0448 (9)	−0.0096 (8)	0.0040 (8)	0.0085 (8)
C51A	0.0468 (9)	0.0430 (9)	0.0517 (10)	0.0042 (7)	0.0113 (8)	0.0071 (7)
C52A	0.0466 (10)	0.0738 (13)	0.0572 (11)	−0.0019 (9)	0.0150 (8)	0.0018 (10)
C53A	0.0636 (12)	0.0794 (14)	0.0526 (11)	−0.0025 (11)	0.0179 (9)	0.0000 (10)
C54A	0.0616 (11)	0.0498 (10)	0.0524 (10)	−0.0016 (8)	0.0025 (9)	0.0062 (8)
C55A	0.0459 (10)	0.0496 (10)	0.0733 (13)	−0.0011 (8)	0.0058 (9)	0.0034 (9)
C56A	0.0464 (10)	0.0494 (10)	0.0639 (11)	0.0016 (8)	0.0159 (8)	0.0007 (8)
Cl2	0.0954 (5)	0.0990 (5)	0.0599 (3)	−0.0053 (4)	0.0049 (3)	−0.0191 (3)
C1B	0.0476 (10)	0.0624 (12)	0.0637 (12)	−0.0105 (9)	−0.0023 (9)	−0.0021 (9)
C2B	0.0450 (10)	0.0606 (11)	0.0552 (10)	−0.0016 (8)	−0.0055 (8)	0.0102 (9)
O3B	0.0400 (7)	0.0825 (10)	0.0885 (11)	0.0098 (7)	−0.0142 (7)	−0.0068 (8)
N4B	0.0401 (8)	0.0713 (11)	0.0855 (13)	0.0057 (8)	0.0006 (8)	−0.0054 (10)
C5B	0.0381 (8)	0.0456 (9)	0.0605 (11)	0.0018 (7)	0.0054 (8)	0.0085 (8)
C6B	0.0380 (8)	0.0518 (10)	0.0452 (9)	−0.0045 (7)	0.0015 (7)	0.0099 (7)
C7B	0.0458 (9)	0.0545 (10)	0.0474 (9)	0.0069 (8)	−0.0009 (7)	0.0051 (8)
C8B	0.0527 (11)	0.0785 (14)	0.0642 (12)	0.0074 (10)	0.0038 (9)	−0.0122 (11)
C9B	0.0636 (13)	0.0854 (16)	0.0591 (12)	−0.0017 (11)	0.0026 (10)	−0.0119 (11)
C10B	0.0676 (13)	0.0503 (11)	0.0668 (12)	−0.0079 (9)	0.0112 (10)	0.0092 (9)
C51B	0.0420 (9)	0.0415 (8)	0.0570 (10)	0.0036 (7)	0.0090 (7)	0.0064 (8)
C52B	0.0433 (10)	0.0668 (12)	0.0719 (13)	0.0027 (9)	0.0171 (9)	−0.0012 (10)
C53B	0.0681 (13)	0.0705 (13)	0.0629 (12)	0.0057 (11)	0.0256 (10)	−0.0056 (10)
C54B	0.0625 (12)	0.0505 (10)	0.0544 (10)	0.0039 (9)	0.0088 (9)	−0.0019 (8)
C55B	0.0466 (10)	0.0539 (10)	0.0594 (11)	−0.0002 (8)	0.0070 (8)	0.0016 (9)
C56B	0.0424 (9)	0.0475 (9)	0.0518 (9)	0.0009 (7)	0.0109 (7)	0.0034 (7)

Geometric parameters (Å, º)

Cl1—C54A	1.739 (2)	Cl2—C54B	1.740 (2)
C1A—C2A	1.523 (3)	C1B—C2B	1.519 (3)
C1A—C9A	1.529 (3)	C1B—C10B	1.532 (3)
C1A—C10A	1.530 (2)	C1B—C9B	1.533 (3)
C1A—H1A	0.98	C1B—H1B	0.98
C2A—O3A	1.455 (2)	C2B—O3B	1.447 (3)
C2A—C6A	1.544 (3)	C2B—C6B	1.541 (2)
C2A—H2A	0.98	C2B—H2B	0.98
O3A—N4A	1.411 (2)	O3B—N4B	1.413 (2)
N4A—C5A	1.279 (2)	N4B—C5B	1.283 (2)
C5A—C51A	1.467 (3)	C5B—C51B	1.464 (3)
C5A—C6A	1.500 (3)	C5B—C6B	1.499 (3)
C6A—C7A	1.539 (2)	C6B—C7B	1.539 (3)
C6A—H6A	0.98	C6B—H6B	0.98
C7A—C10A	1.531 (3)	C7B—C10B	1.528 (3)
C7A—C8A	1.534 (3)	C7B—C8B	1.533 (3)
C7A—H7A	0.98	C7B—H7B	0.98
C8A—C9A	1.552 (3)	C8B—C9B	1.551 (3)
C8A—H8A1	0.97	C8B—H8B1	0.97
C8A—H8A2	0.97	C8B—H8B2	0.97
C9A—H9A1	0.97	C9B—H9B1	0.97
C9A—H9A2	0.97	C9B—H9B2	0.97
C10A—H10A	0.97	C10B—H10C	0.97
C10A—H10B	0.97	C10B—H10D	0.97
C51A—C56A	1.389 (3)	C51B—C56B	1.396 (2)
C51A—C52A	1.397 (3)	C51B—C52B	1.399 (3)
C52A—C53A	1.368 (3)	C52B—C53B	1.370 (3)
C52A—H52A	0.93	C52B—H52B	0.93
C53A—C54A	1.390 (3)	C53B—C54B	1.387 (3)
C53A—H53A	0.93	C53B—H53B	0.93
C54A—C55A	1.372 (3)	C54B—C55B	1.375 (3)
C55A—C56A	1.386 (3)	C55B—C56B	1.379 (3)
C55A—H55A	0.93	C55B—H55B	0.93
C56A—H56A	0.93	C56B—H56B	0.93
C2A—C1A—C9A	107.27 (16)	C2B—C1B—C10B	101.26 (16)
C2A—C1A—C10A	101.89 (15)	C2B—C1B—C9B	108.02 (18)
C9A—C1A—C10A	102.08 (16)	C10B—C1B—C9B	102.00 (18)
C2A—C1A—H1A	114.7	C2B—C1B—H1B	114.7
C9A—C1A—H1A	114.7	C10B—C1B—H1B	114.7
C10A—C1A—H1A	114.7	C9B—C1B—H1B	114.7
O3A—C2A—C1A	111.88 (16)	O3B—C2B—C1B	112.00 (17)
O3A—C2A—C6A	105.17 (15)	O3B—C2B—C6B	105.54 (16)
C1A—C2A—C6A	103.63 (14)	C1B—C2B—C6B	103.92 (15)
O3A—C2A—H2A	111.9	O3B—C2B—H2B	111.7
C1A—C2A—H2A	111.9	C1B—C2B—H2B	111.7
C6A—C2A—H2A	111.9	C6B—C2B—H2B	111.7
N4A—O3A—C2A	109.81 (13)	N4B—O3B—C2B	109.80 (13)
C5A—N4A—O3A	109.75 (16)	C5B—N4B—O3B	109.56 (17)
N4A—C5A—C51A	120.12 (17)	N4B—C5B—C51B	119.46 (18)
N4A—C5A—C6A	114.71 (17)	N4B—C5B—C6B	114.58 (18)
C51A—C5A—C6A	125.10 (16)	C51B—C5B—C6B	125.94 (15)
C5A—C6A—C7A	114.30 (14)	C5B—C6B—C7B	114.93 (15)
C5A—C6A—C2A	100.56 (14)	C5B—C6B—C2B	100.50 (15)
C7A—C6A—C2A	102.81 (15)	C7B—C6B—C2B	102.61 (15)
C5A—C6A—H6A	112.7	C5B—C6B—H6B	112.6
C7A—C6A—H6A	112.7	C7B—C6B—H6B	112.6
C2A—C6A—H6A	112.7	C2B—C6B—H6B	112.6
C10A—C7A—C8A	101.52 (15)	C10B—C7B—C8B	101.67 (17)
C10A—C7A—C6A	101.42 (14)	C10B—C7B—C6B	101.52 (15)
C8A—C7A—C6A	108.17 (15)	C8B—C7B—C6B	108.15 (16)
C10A—C7A—H7A	114.7	C10B—C7B—H7B	114.7
C8A—C7A—H7A	114.7	C8B—C7B—H7B	114.7
C6A—C7A—H7A	114.7	C6B—C7B—H7B	114.7
C7A—C8A—C9A	103.01 (16)	C7B—C8B—C9B	103.07 (17)
C7A—C8A—H8A1	111.2	C7B—C8B—H8B1	111.1
C9A—C8A—H8A1	111.2	C9B—C8B—H8B1	111.1
C7A—C8A—H8A2	111.2	C7B—C8B—H8B2	111.1
C9A—C8A—H8A2	111.2	C9B—C8B—H8B2	111.1
H8A1—C8A—H8A2	109.1	H8B1—C8B—H8B2	109.1
C1A—C9A—C8A	103.12 (15)	C1B—C9B—C8B	103.02 (17)
C1A—C9A—H9A1	111.1	C1B—C9B—H9B1	111.2
C8A—C9A—H9A1	111.1	C8B—C9B—H9B1	111.2
C1A—C9A—H9A2	111.1	C1B—C9B—H9B2	111.2
C8A—C9A—H9A2	111.1	C8B—C9B—H9B2	111.2
H9A1—C9A—H9A2	109.1	H9B1—C9B—H9B2	109.1
C1A—C10A—C7A	94.31 (14)	C7B—C10B—C1B	94.29 (15)
C1A—C10A—H10A	112.9	C7B—C10B—H10C	112.9
C7A—C10A—H10A	112.9	C1B—C10B—H10C	112.9
C1A—C10A—H10B	112.9	C7B—C10B—H10D	112.9
C7A—C10A—H10B	112.9	C1B—C10B—H10D	112.9
H10A—C10A—H10B	110.3	H10C—C10B—H10D	110.3
C56A—C51A—C52A	117.98 (18)	C56B—C51B—C52B	117.77 (18)
C56A—C51A—C5A	120.79 (17)	C56B—C51B—C5B	120.56 (17)
C52A—C51A—C5A	121.24 (17)	C52B—C51B—C5B	121.67 (17)
C53A—C52A—C51A	121.52 (19)	C53B—C52B—C51B	121.54 (18)
C53A—C52A—H52A	119.2	C53B—C52B—H52B	119.2
C51A—C52A—H52A	119.2	C51B—C52B—H52B	119.2
C52A—C53A—C54A	119.32 (19)	C52B—C53B—C54B	119.20 (19)
C52A—C53A—H53A	120.3	C52B—C53B—H53B	120.4
C54A—C53A—H53A	120.3	C54B—C53B—H53B	120.4
C55A—C54A—C53A	120.55 (19)	C55B—C54B—C53B	120.82 (19)
C55A—C54A—Cl1	120.39 (16)	C55B—C54B—Cl2	119.81 (16)
C53A—C54A—Cl1	119.06 (16)	C53B—C54B—Cl2	119.36 (16)
C54A—C55A—C56A	119.69 (18)	C54B—C55B—C56B	119.60 (18)
C54A—C55A—H55A	120.2	C54B—C55B—H55B	120.2
C56A—C55A—H55A	120.2	C56B—C55B—H55B	120.2
C55A—C56A—C51A	120.93 (18)	C55B—C56B—C51B	121.05 (17)
C55A—C56A—H56A	119.5	C55B—C56B—H56B	119.5
C51A—C56A—H56A	119.5	C51B—C56B—H56B	119.5
C9A—C1A—C2A—O3A	−175.03 (14)	C10B—C1B—C2B—O3B	−77.62 (19)
C10A—C1A—C2A—O3A	78.14 (18)	C9B—C1B—C2B—O3B	175.65 (16)
C9A—C1A—C2A—C6A	72.16 (17)	C10B—C1B—C2B—C6B	35.8 (2)
C10A—C1A—C2A—C6A	−34.66 (18)	C9B—C1B—C2B—C6B	−70.9 (2)
C1A—C2A—O3A—N4A	−111.37 (18)	C1B—C2B—O3B—N4B	113.62 (18)
C6A—C2A—O3A—N4A	0.5 (2)	C6B—C2B—O3B—N4B	1.2 (2)
C2A—O3A—N4A—C5A	−0.7 (2)	C2B—O3B—N4B—C5B	−0.4 (2)
O3A—N4A—C5A—C51A	177.83 (16)	O3B—N4B—C5B—C51B	−179.20 (16)
O3A—N4A—C5A—C6A	0.7 (2)	O3B—N4B—C5B—C6B	−0.6 (2)
N4A—C5A—C6A—C7A	109.02 (19)	N4B—C5B—C6B—C7B	−108.04 (19)
C51A—C5A—C6A—C7A	−68.0 (2)	C51B—C5B—C6B—C7B	70.4 (2)
N4A—C5A—C6A—C2A	−0.3 (2)	N4B—C5B—C6B—C2B	1.3 (2)
C51A—C5A—C6A—C2A	−177.35 (16)	C51B—C5B—C6B—C2B	179.76 (17)
O3A—C2A—C6A—C5A	−0.10 (18)	O3B—C2B—C6B—C5B	−1.39 (19)
C1A—C2A—C6A—C5A	117.49 (15)	C1B—C2B—C6B—C5B	−119.39 (17)
O3A—C2A—C6A—C7A	−118.25 (16)	O3B—C2B—C6B—C7B	117.34 (16)
C1A—C2A—C6A—C7A	−0.66 (17)	C1B—C2B—C6B—C7B	−0.7 (2)
C5A—C6A—C7A—C10A	−72.32 (18)	C5B—C6B—C7B—C10B	73.19 (19)
C2A—C6A—C7A—C10A	35.66 (16)	C2B—C6B—C7B—C10B	−34.86 (18)
C5A—C6A—C7A—C8A	−178.63 (15)	C5B—C6B—C7B—C8B	179.69 (15)
C2A—C6A—C7A—C8A	−70.64 (17)	C2B—C6B—C7B—C8B	71.64 (18)
C10A—C7A—C8A—C9A	−35.93 (19)	C10B—C7B—C8B—C9B	36.0 (2)
C6A—C7A—C8A—C9A	70.30 (19)	C6B—C7B—C8B—C9B	−70.4 (2)
C2A—C1A—C9A—C8A	−72.28 (19)	C2B—C1B—C9B—C8B	71.9 (2)
C10A—C1A—C9A—C8A	34.4 (2)	C10B—C1B—C9B—C8B	−34.4 (2)
C7A—C8A—C9A—C1A	1.0 (2)	C7B—C8B—C9B—C1B	−0.9 (2)
C2A—C1A—C10A—C7A	55.42 (17)	C8B—C7B—C10B—C1B	−55.85 (18)
C9A—C1A—C10A—C7A	−55.39 (18)	C6B—C7B—C10B—C1B	55.66 (18)
C8A—C7A—C10A—C1A	55.82 (17)	C2B—C1B—C10B—C7B	−56.06 (18)
C6A—C7A—C10A—C1A	−55.64 (17)	C9B—C1B—C10B—C7B	55.34 (19)
N4A—C5A—C51A—C56A	166.79 (18)	N4B—C5B—C51B—C56B	−159.29 (18)
C6A—C5A—C51A—C56A	−16.4 (3)	C6B—C5B—C51B—C56B	22.3 (3)
N4A—C5A—C51A—C52A	−12.8 (3)	N4B—C5B—C51B—C52B	20.6 (3)
C6A—C5A—C51A—C52A	164.09 (18)	C6B—C5B—C51B—C52B	−157.76 (18)
C56A—C51A—C52A—C53A	1.1 (3)	C56B—C51B—C52B—C53B	−0.4 (3)
C5A—C51A—C52A—C53A	−179.3 (2)	C5B—C51B—C52B—C53B	179.62 (19)
C51A—C52A—C53A—C54A	−0.3 (3)	C51B—C52B—C53B—C54B	1.2 (3)
C52A—C53A—C54A—C55A	−0.8 (3)	C52B—C53B—C54B—C55B	−0.8 (3)
C52A—C53A—C54A—Cl1	178.93 (17)	C52B—C53B—C54B—Cl2	179.69 (17)
C53A—C54A—C55A—C56A	0.9 (3)	C53B—C54B—C55B—C56B	−0.3 (3)
Cl1—C54A—C55A—C56A	−178.78 (15)	Cl2—C54B—C55B—C56B	179.24 (15)
C54A—C55A—C56A—C51A	0.0 (3)	C54B—C55B—C56B—C51B	1.0 (3)
C52A—C51A—C56A—C55A	−1.0 (3)	C52B—C51B—C56B—C55B	−0.7 (3)
C5A—C51A—C56A—C55A	179.44 (16)	C5B—C51B—C56B—C55B	179.28 (16)