(2R)-Ethyl 2-(5-bromo-2,3-dioxoindolin-1-yl)propanoate.

The title compound, C(13)H(12)BrNO(4), was obtained from an optically active aniline derivative. The structure was characterized by (1)H NMR, (13)C NMR, MS and X-ray diffraction techniques. 86% of the atoms of the two independent mol-ecules in the asymmetric unit show non-crystallographic inversion symmetry.

Related literature

For related structures, see: Akkurt et al. (2006 ▶); Miehe et al. (1991 ▶); Robeyns et al. (2007 ▶). For general background, see: Sandmeyer (1919 ▶); Silva et al. (2001 ▶); Spek (2003 ▶).

Experimental

Crystal data

C13H12BrNO4

M = 326.14

Monoclinic,

a = 9.7390 (13) Å

b = 14.355 (2) Å

c = 9.8361 (10) Å

β = 95.779 (9)°

V = 1368.1 (3) Å3

Z = 4

Cu Kα radiation

μ = 4.20 mm−1

T = 293 (2) K

0.20 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.385, T max = 0.432

6047 measured reflections

5502 independent reflections

3935 reflections with I > 2σ(I)

R int = 0.020

1 standard reflection frequency: 60 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.140

S = 1.02

5502 reflections

348 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.38 e Å−3

Absolute structure: Flack (1983 ▶), 2566 Friedel pairs

Flack parameter: −0.06 (3)

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020588/bt2723sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020588/bt2723Isup2.hkl

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

C13H12BrNO4	F000 = 656
Mr = 326.14	Dx = 1.583 Mg m−3
Monoclinic, P21	Melting point: 404.5 K
Hall symbol: P 2yb	Cu Kα radiation λ = 1.54184 Å
a = 9.7390 (13) Å	Cell parameters from 25 reflections
b = 14.355 (2) Å	θ = 32.2–34.4º
c = 9.8361 (10) Å	µ = 4.20 mm−1
β = 95.779 (9)º	T = 293 (2) K
V = 1368.1 (3) Å3	Prism, red
Z = 4	0.20 × 0.20 × 0.20 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.020
Radiation source: Fine–focus sealed tube	θmax = 74.9º
Monochromator: graphite	θmin = 4.5º
T = 293(2) K	h = −12→12
Non–profiled ω scans	k = −17→17
Absorption correction: ψ scan(North et al., 1968)	l = −12→12
Tmin = 0.385, Tmax = 0.432	1 standard reflections
6047 measured reflections	every 60 min
5502 independent reflections	intensity decay: 2%
3935 reflections with I > 2σ(I)

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.051	w = 1/[σ2(Fo2) + (0.0642P)2 + 0.5869P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.140	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.45 e Å−3
5502 reflections	Δρmin = −0.38 e Å−3
348 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.0039 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Flack parameter: −0.06 (3)

Experimental. Number of ψ–scan sets used was 8. The θ correction was applied. Averaged transmission function was used. No Fourier smoothing was applied.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
N1a	0.0320 (4)	0.0742 (3)	0.5522 (4)	0.0519 (9)
C2a	0.0599 (5)	−0.0181 (3)	0.5310 (6)	0.0558 (11)
O21a	0.1299 (4)	−0.0683 (3)	0.6073 (5)	0.0748 (11)
C3a	−0.0156 (6)	−0.0421 (3)	0.3892 (6)	0.0599 (13)
O31a	−0.0148 (5)	−0.1195 (2)	0.3406 (5)	0.0838 (13)
C4a	−0.0793 (5)	0.0440 (3)	0.3390 (5)	0.0536 (12)
C5a	−0.1571 (6)	0.0641 (4)	0.2187 (6)	0.0655 (14)
H5a	−0.1750	0.0188	0.1517	0.079*
C6a	−0.2075 (6)	0.1520 (4)	0.1997 (6)	0.0683 (15)
Br6a	−0.31241 (9)	0.18369 (7)	0.03306 (8)	0.1113 (3)
C7a	−0.1789 (6)	0.2207 (4)	0.2980 (6)	0.0603 (13)
H7a	−0.2141	0.2804	0.2822	0.072*
C8a	−0.1000 (5)	0.2019 (3)	0.4175 (5)	0.0542 (12)
H8a	−0.0799	0.2482	0.4827	0.065*
C9a	−0.0506 (5)	0.1117 (3)	0.4392 (5)	0.0468 (10)
C10a	0.0842 (5)	0.1204 (3)	0.6760 (5)	0.0524 (11)
H10a	0.1315	0.0724	0.7341	0.063*
C11a	−0.0284 (6)	0.1595 (4)	0.7571 (5)	0.0663 (15)
H11a	−0.0726	0.2112	0.7085	0.099*
H11b	0.0119	0.1801	0.8450	0.099*
H11c	−0.0954	0.1119	0.7687	0.099*
C12a	0.1957 (5)	0.1904 (4)	0.6456 (5)	0.0539 (11)
O12a	0.2353 (4)	0.2019 (3)	0.5372 (4)	0.0787 (12)
O13a	0.2439 (4)	0.2352 (3)	0.7588 (4)	0.0654 (10)
C14a	0.3501 (6)	0.3044 (5)	0.7423 (6)	0.0764 (17)
H14a	0.4308	0.2749	0.7111	0.092*
H14b	0.3160	0.3506	0.6753	0.092*
C15A	0.3859 (7)	0.3487 (5)	0.8757 (7)	0.089 (2)
H15A	0.3052	0.3772	0.9060	0.133*
H15B	0.4552	0.3954	0.8675	0.133*
H15C	0.4208	0.3026	0.9408	0.133*
N1b	0.5010 (4)	0.5226 (3)	0.4543 (4)	0.0580 (10)
C2b	0.4556 (6)	0.6130 (4)	0.4568 (7)	0.0662 (15)
O21b	0.3847 (5)	0.6536 (3)	0.3690 (6)	0.0947 (15)
C3b	0.5115 (6)	0.6509 (4)	0.5989 (7)	0.0671 (15)
O31b	0.4928 (5)	0.7288 (3)	0.6363 (6)	0.0896 (15)
C4b	0.5872 (5)	0.5728 (4)	0.6681 (5)	0.0567 (12)
C5b	0.6581 (6)	0.5656 (5)	0.7945 (6)	0.0692 (15)
H5b	0.6639	0.6155	0.8551	0.083*
C6b	0.7207 (5)	0.4817 (5)	0.8295 (5)	0.0689 (14)
Br6b	0.82477 (10)	0.46814 (8)	1.00249 (8)	0.1231 (4)
C7b	0.7096 (6)	0.4070 (4)	0.7425 (6)	0.0671 (14)
H7b	0.7517	0.3510	0.7701	0.080*
C8b	0.6371 (5)	0.4131 (4)	0.6151 (5)	0.0553 (12)
H8b	0.6295	0.3623	0.5560	0.066*
C9b	0.5761 (5)	0.4980 (3)	0.5786 (5)	0.0459 (10)
C10b	0.4649 (5)	0.4574 (4)	0.3427 (5)	0.0596 (12)
H10b	0.5158	0.3999	0.3665	0.072*
C11b	0.5102 (7)	0.4896 (7)	0.2087 (7)	0.106 (3)
H11d	0.4538	0.5411	0.1747	0.159*
H11e	0.5008	0.4394	0.1440	0.159*
H11f	0.6050	0.5090	0.2219	0.159*
C12b	0.3120 (5)	0.4334 (4)	0.3396 (5)	0.0559 (12)
O12b	0.2423 (4)	0.4511 (3)	0.4281 (4)	0.0780 (11)
O13b	0.2720 (4)	0.3850 (3)	0.2285 (4)	0.0750 (11)
C14b	0.1338 (7)	0.3446 (7)	0.2229 (9)	0.105 (3)
H14c	0.1250	0.3089	0.3054	0.126*
H14d	0.0654	0.3940	0.2178	0.126*
C15b	0.1098 (8)	0.2856 (6)	0.1066 (9)	0.114 (3)
H15d	0.1309	0.3188	0.0265	0.171*
H15e	0.0147	0.2668	0.0959	0.171*
H15f	0.1676	0.2315	0.1189	0.171*

	U11	U22	U33	U12	U13	U23
N1a	0.059 (2)	0.0364 (19)	0.059 (2)	0.0009 (17)	−0.0007 (18)	−0.0023 (17)
C2a	0.052 (3)	0.038 (2)	0.079 (3)	−0.001 (2)	0.015 (2)	0.002 (2)
O21a	0.074 (2)	0.045 (2)	0.104 (3)	0.0080 (18)	0.006 (2)	0.008 (2)
C3a	0.065 (3)	0.041 (3)	0.075 (3)	−0.006 (2)	0.016 (3)	−0.012 (3)
O31a	0.094 (3)	0.0413 (19)	0.116 (4)	−0.0057 (19)	0.011 (3)	−0.027 (2)
C4a	0.062 (3)	0.040 (3)	0.059 (3)	−0.008 (2)	0.008 (2)	−0.008 (2)
C5a	0.076 (4)	0.056 (3)	0.064 (3)	−0.021 (3)	0.003 (3)	−0.009 (3)
C6a	0.065 (3)	0.073 (4)	0.065 (3)	−0.015 (3)	−0.003 (3)	0.000 (3)
Br6A	0.1135 (6)	0.1265 (7)	0.0846 (5)	−0.0145 (5)	−0.0355 (4)	0.0150 (5)
C7a	0.059 (3)	0.048 (3)	0.074 (3)	−0.002 (2)	0.005 (3)	0.008 (2)
C8a	0.059 (3)	0.035 (2)	0.067 (3)	−0.004 (2)	−0.002 (2)	−0.004 (2)
C9a	0.047 (2)	0.040 (2)	0.053 (2)	−0.0066 (19)	0.005 (2)	−0.005 (2)
C10a	0.059 (3)	0.042 (2)	0.054 (3)	−0.003 (2)	0.000 (2)	0.006 (2)
C11a	0.069 (3)	0.075 (4)	0.057 (3)	−0.014 (3)	0.017 (3)	−0.006 (3)
C12a	0.048 (2)	0.053 (3)	0.062 (3)	−0.002 (2)	0.009 (2)	−0.003 (3)
O12a	0.074 (2)	0.100 (3)	0.066 (2)	−0.025 (2)	0.0229 (19)	−0.011 (2)
O13a	0.062 (2)	0.073 (2)	0.061 (2)	−0.0174 (18)	0.0030 (17)	−0.0111 (18)
C14a	0.061 (3)	0.091 (4)	0.078 (4)	−0.031 (3)	0.013 (3)	−0.021 (3)
C15a	0.071 (4)	0.102 (5)	0.092 (5)	−0.023 (4)	0.006 (3)	−0.029 (4)
N1b	0.058 (2)	0.051 (2)	0.063 (3)	0.000 (2)	−0.003 (2)	−0.0029 (19)
C2b	0.055 (3)	0.050 (3)	0.093 (4)	0.003 (2)	0.004 (3)	0.010 (3)
O21b	0.077 (3)	0.078 (3)	0.125 (4)	0.009 (2)	−0.011 (3)	0.035 (3)
C3b	0.057 (3)	0.048 (3)	0.099 (4)	−0.006 (2)	0.018 (3)	−0.002 (3)
O31b	0.085 (3)	0.044 (2)	0.142 (4)	−0.002 (2)	0.022 (3)	−0.016 (2)
C4b	0.054 (3)	0.051 (3)	0.066 (3)	−0.007 (2)	0.009 (2)	−0.012 (2)
C5b	0.060 (3)	0.076 (4)	0.071 (3)	−0.011 (3)	0.003 (3)	−0.027 (3)
C6b	0.056 (3)	0.093 (4)	0.057 (3)	0.004 (3)	−0.001 (2)	−0.006 (3)
Br6b	0.1132 (6)	0.1801 (10)	0.0686 (4)	0.0217 (6)	−0.0264 (4)	−0.0147 (6)
C7b	0.058 (3)	0.077 (4)	0.066 (3)	0.010 (3)	0.005 (3)	0.003 (3)
C8b	0.056 (3)	0.055 (3)	0.055 (3)	0.000 (2)	0.005 (2)	−0.003 (2)
C9b	0.042 (2)	0.045 (2)	0.051 (2)	−0.0056 (19)	0.0017 (18)	−0.0036 (19)
C10b	0.052 (3)	0.071 (3)	0.054 (2)	−0.002 (3)	−0.003 (2)	−0.006 (3)
C11b	0.088 (5)	0.164 (8)	0.069 (4)	−0.043 (5)	0.022 (3)	−0.027 (5)
C12b	0.058 (3)	0.059 (3)	0.051 (3)	0.000 (2)	0.003 (2)	−0.001 (2)
O12b	0.072 (2)	0.084 (3)	0.082 (3)	−0.013 (2)	0.027 (2)	−0.018 (2)
O13b	0.054 (2)	0.099 (3)	0.072 (2)	−0.013 (2)	0.0042 (18)	−0.018 (2)
C14b	0.061 (4)	0.143 (7)	0.112 (6)	−0.028 (4)	0.016 (4)	−0.037 (5)
C15b	0.086 (5)	0.117 (6)	0.140 (7)	−0.035 (5)	0.017 (5)	−0.049 (6)

N1a—C2a	1.372 (6)	N1b—C2b	1.373 (7)
N1a—C9a	1.412 (6)	N1b—C9b	1.405 (6)
N1a—C10a	1.434 (6)	N1b—C10b	1.457 (6)
C2a—O21a	1.202 (6)	C2b—O21b	1.201 (7)
C2a—C3a	1.548 (7)	C2b—C3b	1.547 (9)
C3a—O31a	1.209 (6)	C3b—O31b	1.197 (6)
C3a—C4a	1.447 (7)	C3b—C4b	1.471 (8)
C4a—C5a	1.370 (7)	C4b—C5b	1.364 (8)
C4a—C9a	1.392 (6)	C4b—C9b	1.386 (7)
C5a—C6a	1.361 (8)	C5b—C6b	1.378 (9)
C5a—H5a	0.9300	C5b—H5b	0.9300
C6a—C7a	1.390 (8)	C6b—C7b	1.369 (8)
C6a—Br6a	1.897 (6)	C6b—Br6b	1.901 (5)
C7a—C8a	1.365 (7)	C7b—C8b	1.378 (7)
C7a—H7a	0.9300	C7b—H7b	0.9300
C8a—C9a	1.391 (7)	C8b—C9b	1.388 (7)
C8a—H8a	0.9300	C8b—H8b	0.9300
C10a—C11a	1.526 (7)	C10b—C11b	1.504 (8)
C10a—C12a	1.531 (7)	C10b—C12b	1.526 (7)
C10a—H10a	0.9800	C10b—H10b	0.9800
C11a—H11a	0.9600	C11b—H11d	0.9600
C11a—H11b	0.9600	C11b—H11e	0.9600
C11a—H11c	0.9600	C11b—H11f	0.9600
C12a—O12a	1.182 (6)	C12b—O12b	1.185 (6)
C12a—O13a	1.329 (6)	C12b—O13b	1.321 (6)
O13a—C14a	1.455 (6)	O13b—C14b	1.462 (7)
C14a—C15a	1.469 (8)	C14b—C15b	1.424 (10)
C14a—H14a	0.9700	C14b—H14c	0.9700
C14a—H14b	0.9700	C14b—H14d	0.9700
C15a—H15a	0.9600	C15b—H15d	0.9600
C15a—H15b	0.9600	C15b—H15e	0.9600
C15a—H15c	0.9600	C15b—H15f	0.9600
C2a—N1a—C9a	110.7 (4)	C2b—N1b—C9b	111.2 (4)
C2a—N1a—C10a	121.2 (4)	C2b—N1b—C10b	124.5 (5)
C9a—N1a—C10a	128.1 (4)	C9b—N1b—C10b	124.0 (4)
O21a—C2a—N1a	126.3 (5)	O21b—C2b—N1b	127.5 (6)
O21a—C2a—C3a	128.1 (5)	O21b—C2b—C3b	127.1 (6)
N1a—C2a—C3a	105.6 (4)	N1b—C2b—C3b	105.3 (5)
O31a—C3a—C4a	132.0 (5)	O31b—C3b—C4b	130.9 (7)
O31a—C3a—C2a	122.6 (5)	O31b—C3b—C2b	123.8 (6)
C4a—C3a—C2a	105.4 (4)	C4b—C3b—C2b	105.3 (5)
C5a—C4a—C9a	121.2 (5)	C5b—C4b—C9b	121.4 (5)
C5a—C4a—C3a	131.0 (5)	C5b—C4b—C3b	131.6 (5)
C9a—C4a—C3a	107.8 (4)	C9b—C4b—C3b	107.0 (5)
C4a—C5a—C6a	118.4 (5)	C4b—C5b—C6b	117.7 (5)
C4a—C5a—H5a	120.8	C4b—C5b—H5b	121.2
C6a—C5a—H5a	120.8	C6b—C5b—H5b	121.2
C5a—C6a—C7a	121.2 (5)	C5b—C6b—C7b	121.6 (5)
C5a—C6a—Br6a	119.8 (4)	C5b—C6b—Br6b	119.7 (5)
C7a—C6a—Br6a	118.9 (4)	C7b—C6b—Br6b	118.7 (5)
C8a—C7a—C6a	121.0 (5)	C8b—C7b—C6b	121.3 (6)
C8a—C7a—H7a	119.5	C8b—C7b—H7b	119.3
C6a—C7a—H7a	119.5	C6b—C7b—H7b	119.3
C7a—C8a—C9a	118.2 (4)	C7b—C8b—C9b	117.2 (5)
C7a—C8a—H8a	120.9	C7b—C8b—H8b	121.4
C9a—C8a—H8a	120.9	C9b—C8b—H8b	121.4
C8a—C9a—C4a	120.0 (4)	C8b—C9b—C4b	120.8 (4)
C8a—C9a—N1a	129.6 (4)	C8b—C9b—N1b	128.1 (4)
C4a—C9a—N1a	110.4 (4)	C4b—C9b—N1b	111.1 (4)
N1a—C10a—C11a	113.7 (4)	N1b—C10b—C11b	113.1 (5)
N1a—C10a—C12a	109.6 (4)	N1b—C10b—C12b	108.7 (4)
C11a—C10a—C12a	115.0 (4)	C11b—C10b—C12b	115.1 (5)
N1a—C10a—H10a	105.9	N1b—C10b—H10b	106.4
C11a—C10a—H10a	105.9	C11b—C10b—H10b	106.4
C12a—C10a—H10a	105.9	C12b—C10b—H10b	106.4
C10a—C11a—H11a	109.5	C10b—C11b—H11d	109.5
C10a—C11a—H11b	109.5	C10b—C11b—H11e	109.5
H11a—C11a—H11b	109.5	H11d—C11b—H11e	109.5
C10a—C11a—H11c	109.5	C10b—C11b—H11f	109.5
H11a—C11a—H11c	109.5	H11d—C11b—H11f	109.5
H11b—C11a—H11c	109.5	H11e—C11b—H11f	109.5
O12a—C12a—O13a	124.6 (5)	O12b—C12b—O13b	125.3 (5)
O12a—C12a—C10a	124.8 (5)	O12b—C12b—C10b	124.6 (5)
O13a—C12a—C10a	110.6 (4)	O13b—C12b—C10b	110.0 (5)
C12a—O13a—C14a	115.6 (4)	C12b—O13b—C14b	115.7 (5)
C15a—C14a—O13a	107.7 (5)	C15b—C14b—O13b	110.0 (6)
C15a—C14a—H14a	110.2	C15b—C14b—H14c	109.7
O13a—C14a—H14a	110.2	O13b—C14b—H14c	109.7
C15a—C14a—H14b	110.2	C15b—C14b—H14d	109.7
O13a—C14a—H14b	110.2	O13b—C14b—H14d	109.7
H14a—C14a—H14b	108.5	H14c—C14b—H14d	108.2
C14a—C15a—H15a	109.5	C14b—C15b—H15d	109.5
C14a—C15a—H15b	109.5	C14b—C15b—H15e	109.5
H15a—C15a—H15b	109.5	H15d—C15b—H15e	109.5
C14a—C15a—H15c	109.5	C14b—C15b—H15f	109.5
H15a—C15a—H15c	109.5	H15d—C15b—H15f	109.5
H15b—C15a—H15c	109.5	H15e—C15b—H15f	109.5
C9a—N1a—C2a—O21a	178.3 (5)	C9b—N1b—C2b—O21b	−176.9 (6)
C10a—N1a—C2a—O21a	−1.7 (8)	C10b—N1b—C2b—O21b	−2.6 (9)
C9a—N1a—C2a—C3a	−0.9 (5)	C9b—N1b—C2b—C3b	1.4 (6)
C10a—N1a—C2a—C3a	179.0 (4)	C10b—N1b—C2b—C3b	175.7 (4)
O21a—C2a—C3a—O31a	2.6 (9)	O21b—C2b—C3b—O31b	−2.5 (10)
N1a—C2a—C3a—O31a	−178.2 (5)	N1b—C2b—C3b—O31b	179.2 (6)
O21a—C2a—C3a—C4a	−177.6 (5)	O21b—C2b—C3b—C4b	177.8 (6)
N1a—C2a—C3a—C4a	1.7 (5)	N1b—C2b—C3b—C4b	−0.5 (6)
O31a—C3a—C4a—C5a	−1.2 (11)	O31b—C3b—C4b—C5b	0.0 (11)
C2a—C3a—C4a—C5a	179.0 (6)	C2b—C3b—C4b—C5b	179.7 (6)
O31a—C3a—C4a—C9a	178.0 (6)	O31b—C3b—C4b—C9b	179.8 (6)
C2a—C3a—C4a—C9a	−1.8 (6)	C2b—C3b—C4b—C9b	−0.5 (6)
C9a—C4a—C5a—C6a	−0.7 (8)	C9b—C4b—C5b—C6b	1.3 (9)
C3a—C4a—C5a—C6a	178.4 (6)	C3b—C4b—C5b—C6b	−179.0 (6)
C4a—C5a—C6a—C7a	1.3 (9)	C4b—C5b—C6b—C7b	−1.9 (9)
C4a—C5a—C6a—Br6a	178.7 (4)	C4b—C5b—C6b—Br6b	178.5 (4)
C5a—C6a—C7a—C8a	−0.5 (9)	C5b—C6b—C7b—C8b	1.3 (9)
Br6a—C6a—C7a—C8a	−177.8 (4)	Br6b—C6b—C7b—C8b	−179.1 (4)
C6a—C7a—C8a—C9a	−1.0 (8)	C6b—C7b—C8b—C9b	0.0 (8)
C7a—C8a—C9a—C4a	1.5 (7)	C7b—C8b—C9b—C4b	−0.6 (8)
C7a—C8a—C9a—N1a	180.0 (5)	C7b—C8b—C9b—N1b	178.0 (5)
C5a—C4a—C9a—C8a	−0.7 (8)	C5b—C4b—C9b—C8b	−0.1 (8)
C3a—C4a—C9a—C8a	−180.0 (5)	C3b—C4b—C9b—C8b	−179.8 (5)
C5a—C4a—C9a—N1a	−179.4 (5)	C5b—C4b—C9b—N1b	−178.8 (5)
C3a—C4a—C9a—N1a	1.3 (6)	C3b—C4b—C9b—N1b	1.4 (6)
C2a—N1a—C9a—C8a	−178.8 (5)	C2b—N1b—C9b—C8b	179.5 (5)
C10a—N1a—C9a—C8a	1.3 (8)	C10b—N1b—C9b—C8b	5.1 (8)
C2a—N1a—C9a—C4a	−0.2 (6)	C2b—N1b—C9b—C4b	−1.8 (6)
C10a—N1a—C9a—C4a	179.9 (5)	C10b—N1b—C9b—C4b	−176.2 (5)
C2a—N1a—C10a—C11a	−119.8 (5)	C2b—N1b—C10b—C11b	60.4 (7)
C9a—N1a—C10a—C11a	60.1 (6)	C9b—N1b—C10b—C11b	−125.9 (6)
C2a—N1a—C10a—C12a	109.9 (5)	C2b—N1b—C10b—C12b	−68.7 (6)
C9a—N1a—C10a—C12a	−70.1 (6)	C9b—N1b—C10b—C12b	104.9 (5)
N1a—C10a—C12a—O12a	−2.3 (7)	N1b—C10b—C12b—O12b	−12.8 (8)
C11a—C10a—C12a—O12a	−131.8 (6)	C11b—C10b—C12b—O12b	−140.8 (7)
N1a—C10a—C12a—O13a	179.0 (4)	N1b—C10b—C12b—O13b	171.3 (4)
C11A—C10a—C12a—O13a	49.5 (6)	C11b—C10b—C12b—O13b	43.3 (7)
O12A—C12a—O13a—C14a	1.8 (8)	O12b—C12b—O13b—C14b	−5.3 (9)
C10A—C12a—O13a—C14a	−179.5 (5)	C10b—C12b—O13b—C14b	170.6 (6)
C12A—O13a—C14a—C15a	177.7 (5)	C12b—O13b—C14b—C15b	−173.2 (7)