3,3'-Dibromo-5,5'-bis-[(S)-l-menth-yloxy]-4,4'-(hexane-1,6-diyldiimino)difuran-2(5H)-one.

The title compound, C(34)H(54)Br(2)N(2)O(6), was obtained by the Michael addition-elimination reaction of (5S)-5-(l-menthyl-oxy)-3,4-dibromo-furan-2(5H)-one with 1,6-hexa-nediamine in the presence of triethyl-amine. The crystal structure contains two chiral five-membered furan-one rings, in twist and envelope conformations, and two six-membered cyclo-hexane rings in chair conformations.

Related literature

For general background, see: Boukouvalas et al. (2007 ▶); Carter et al. (2002 ▶); Feringa & de Lange (1988 ▶); Pal et al. (2003 ▶).

Experimental

Crystal data

C34H54Br2N2O6

M = 746.61

Triclinic,

a = 8.2302 (2) Å

b = 9.1319 (2) Å

c = 12.7193 (3) Å

α = 105.0370 (10)°

β = 93.214 (2)°

γ = 100.499 (2)°

V = 902.37 (4) Å3

Z = 1

Mo Kα radiation

μ = 2.29 mm−1

T = 298 (2) K

0.28 × 0.25 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.567, T max = 0.645

11045 measured reflections

5935 independent reflections

4414 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.090

S = 0.97

5935 reflections

403 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 2587 Friedel pairs

Flack parameter: 0.001 (8)

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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/S1600536808020333/kp2170sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020333/kp2170Isup2.hkl

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

C34H54Br2N2O6	Z = 1
Mr = 746.61	F000 = 390
Triclinic, P1	Dx = 1.374 Mg m−3
Hall symbol: P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.2302 (2) Å	Cell parameters from 2819 reflections
b = 9.1319 (2) Å	θ = 2.0–23.7º
c = 12.7193 (3) Å	µ = 2.29 mm−1
α = 105.0370 (10)º	T = 298 (2) K
β = 93.214 (2)º	Block, colourless
γ = 100.499 (2)º	0.28 × 0.25 × 0.21 mm
V = 902.37 (4) Å3

Bruker SMART CCD area-detector diffractometer	5935 independent reflections
Radiation source: fine-focus sealed tube	4414 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.032
T = 298(2) K	θmax = 25.5º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.567, Tmax = 0.645	k = −11→11
11045 measured reflections	l = −15→15

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039	w = 1/[σ2(Fo2) + (0.0205P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.090	(Δ/σ)max < 0.001
S = 0.98	Δρmax = 0.50 e Å−3
5935 reflections	Δρmin = −0.25 e Å−3
403 parameters	Extinction correction: none
3 restraints	Absolute structure: Flack (1983), 2587 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.001 (8)
Secondary atom site location: difference Fourier map

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
Br1	0.81496 (5)	0.16597 (5)	0.19540 (3)	0.0760 (2)
Br2	−0.34832 (6)	−0.19512 (5)	−0.08054 (3)	0.0817 (2)
O1	0.6471 (4)	0.2464 (3)	0.5844 (3)	0.0488 (9)
O2	0.9096 (4)	0.2804 (4)	0.5257 (2)	0.0628 (8)
O3	1.0762 (5)	0.1927 (5)	0.4010 (4)	0.0813 (12)
O4	−0.1811 (4)	−0.2781 (3)	−0.4703 (3)	0.0416 (8)
O5	−0.3972 (4)	−0.1676 (3)	−0.3926 (2)	0.0535 (7)
O6	−0.5937 (5)	−0.1698 (4)	−0.2778 (3)	0.0754 (11)
N1	0.5276 (5)	0.2891 (4)	0.3820 (3)	0.0567 (10)
H1	0.4719	0.3169	0.4363	0.068*
N2	−0.0273 (5)	−0.2212 (4)	−0.2574 (3)	0.0583 (10)
H2A	0.0307	−0.2360	−0.3120	0.070*
C1	0.3035 (7)	0.4220 (6)	0.6869 (6)	0.0815 (19)
H1A	0.2956	0.4654	0.7633	0.122*
H1B	0.2016	0.4191	0.6451	0.122*
H1C	0.3938	0.4848	0.6640	0.122*
C2	0.3345 (6)	0.2579 (5)	0.6683 (4)	0.0491 (13)
H2	0.3483	0.2190	0.5907	0.059*
C3	0.1811 (6)	0.1539 (6)	0.6920 (4)	0.0591 (13)
H3A	0.2041	0.0533	0.6877	0.089*
H3B	0.0892	0.1444	0.6390	0.089*
H3C	0.1536	0.1987	0.7641	0.089*
C4	0.4919 (6)	0.2472 (5)	0.7355 (4)	0.0421 (11)
H4	0.4936	0.1367	0.7207	0.051*
C5	0.4948 (7)	0.3092 (6)	0.8604 (4)	0.0534 (13)
H5A	0.4883	0.4177	0.8783	0.064*
H5B	0.3976	0.2537	0.8837	0.064*
C6	0.6485 (9)	0.2925 (7)	0.9225 (5)	0.0574 (13)
H6A	0.6451	0.3364	1.0003	0.069*
H6B	0.6497	0.1834	0.9103	0.069*
C7	0.8034 (5)	0.3711 (5)	0.8886 (3)	0.0500 (10)
H7	0.8011	0.4816	0.9046	0.060*
C8	0.9614 (8)	0.3565 (7)	0.9516 (5)	0.0807 (19)
H8A	0.9573	0.3971	1.0288	0.121*
H8B	1.0570	0.4137	0.9296	0.121*
H8C	0.9688	0.2494	0.9359	0.121*
C9	0.8047 (6)	0.3094 (5)	0.7646 (4)	0.0477 (11)
H9A	0.9017	0.3668	0.7424	0.057*
H9B	0.8141	0.2016	0.7473	0.057*
C10	0.6510 (5)	0.3221 (5)	0.6998 (3)	0.0412 (9)
H10	0.6504	0.4319	0.7090	0.049*
C11	0.7495 (5)	0.3225 (5)	0.5261 (3)	0.0450 (9)
H11	0.7621	0.4347	0.5558	0.054*
C12	0.9450 (7)	0.2278 (6)	0.4195 (4)	0.0560 (12)
C13	0.8051 (7)	0.2291 (5)	0.3483 (4)	0.0527 (12)
C14	0.6817 (6)	0.2727 (5)	0.4052 (3)	0.0434 (10)
C15	0.4440 (7)	0.2641 (5)	0.2717 (4)	0.0557 (13)
H15A	0.5250	0.3006	0.2268	0.067*
H15B	0.3600	0.3269	0.2771	0.067*
C16	0.3626 (6)	0.0992 (5)	0.2142 (4)	0.0523 (12)
H16A	0.2760	0.0628	0.2555	0.063*
H16B	0.4442	0.0340	0.2097	0.063*
C17	0.2882 (7)	0.0881 (6)	0.1000 (4)	0.0598 (14)
H17A	0.2092	0.1560	0.1062	0.072*
H17B	0.3764	0.1267	0.0605	0.072*
C18	0.2019 (7)	−0.0710 (5)	0.0330 (4)	0.0575 (13)
H18A	0.1150	−0.1118	0.0723	0.069*
H18B	0.2811	−0.1388	0.0232	0.069*
C19	0.1264 (8)	−0.0707 (6)	−0.0781 (4)	0.0631 (14)
H19A	0.0414	−0.0088	−0.0677	0.076*
H19B	0.2120	−0.0212	−0.1142	0.076*
C20	0.0509 (7)	−0.2275 (6)	−0.1513 (4)	0.0580 (13)
H20A	0.1363	−0.2885	−0.1648	0.070*
H20B	−0.0324	−0.2790	−0.1147	0.070*
C21	−0.1792 (6)	−0.1947 (5)	−0.2765 (3)	0.0464 (10)
C22	−0.3149 (6)	−0.1883 (5)	−0.2240 (4)	0.0501 (12)
C23	−0.4531 (7)	−0.1733 (5)	−0.2942 (4)	0.0543 (12)
C24	−0.2224 (5)	−0.1659 (4)	−0.3874 (3)	0.0438 (9)
H24	−0.1615	−0.0637	−0.3886	0.053*
C25	−0.1587 (5)	−0.2389 (5)	−0.5739 (3)	0.0422 (9)
H25	−0.1167	−0.1271	−0.5583	0.051*
C26	−0.3272 (6)	−0.2820 (5)	−0.6436 (4)	0.0479 (12)
H26A	−0.3776	−0.3886	−0.6487	0.057*
H26B	−0.3998	−0.2169	−0.6074	0.057*
C27	−0.3136 (6)	−0.2637 (5)	−0.7591 (3)	0.0540 (11)
H27	−0.2764	−0.1533	−0.7531	0.065*
C28	−0.4850 (7)	−0.3194 (8)	−0.8265 (4)	0.0748 (17)
H28A	−0.4754	−0.3079	−0.8989	0.112*
H28B	−0.5608	−0.2588	−0.7918	0.112*
H28C	−0.5258	−0.4265	−0.8308	0.112*
C29	−0.1843 (9)	−0.3484 (8)	−0.8117 (5)	0.0659 (15)
H29A	−0.1695	−0.3286	−0.8823	0.079*
H29B	−0.2236	−0.4589	−0.8242	0.079*
C30	−0.0177 (7)	−0.2986 (7)	−0.7412 (4)	0.0651 (15)
H30A	0.0262	−0.1900	−0.7341	0.078*
H30B	0.0600	−0.3576	−0.7773	0.078*
C31	−0.0318 (6)	−0.3223 (5)	−0.6278 (4)	0.0465 (12)
H31	−0.0756	−0.4330	−0.6387	0.056*
C32	0.1388 (6)	−0.2838 (6)	−0.5590 (5)	0.0545 (13)
H32	0.1153	−0.2782	−0.4835	0.065*
C33	0.2355 (8)	−0.4138 (7)	−0.5922 (6)	0.0851 (18)
H33A	0.2692	−0.4188	−0.6639	0.128*
H33B	0.1659	−0.5107	−0.5930	0.128*
H33C	0.3320	−0.3933	−0.5406	0.128*
C34	0.2432 (7)	−0.1293 (6)	−0.5557 (5)	0.0677 (15)
H34A	0.2826	−0.1333	−0.6258	0.102*
H34B	0.3362	−0.1044	−0.5007	0.102*
H34C	0.1774	−0.0512	−0.5384	0.102*

	U11	U22	U33	U12	U13	U23
Br1	0.1001 (5)	0.0902 (4)	0.0445 (3)	0.0276 (3)	0.0298 (3)	0.0200 (3)
Br2	0.1127 (5)	0.0972 (4)	0.0483 (4)	0.0293 (4)	0.0368 (4)	0.0320 (3)
O1	0.058 (2)	0.0498 (18)	0.0312 (18)	0.0000 (16)	0.0030 (17)	0.0068 (14)
O2	0.0488 (19)	0.100 (2)	0.0454 (17)	0.0176 (17)	0.0113 (14)	0.0272 (16)
O3	0.064 (3)	0.117 (3)	0.085 (3)	0.040 (2)	0.030 (2)	0.047 (2)
O4	0.0459 (19)	0.0449 (17)	0.0359 (19)	0.0083 (14)	0.0140 (16)	0.0129 (14)
O5	0.0533 (19)	0.0693 (19)	0.0458 (16)	0.0212 (15)	0.0161 (14)	0.0217 (14)
O6	0.075 (3)	0.086 (3)	0.085 (3)	0.037 (2)	0.042 (2)	0.037 (2)
N1	0.063 (3)	0.070 (3)	0.0352 (19)	0.021 (2)	0.0022 (18)	0.0063 (18)
N2	0.057 (3)	0.077 (3)	0.0358 (19)	0.003 (2)	0.0035 (18)	0.0146 (18)
C1	0.062 (4)	0.066 (3)	0.119 (5)	0.013 (3)	−0.009 (3)	0.034 (3)
C2	0.052 (3)	0.047 (3)	0.045 (3)	0.005 (2)	0.006 (3)	0.011 (2)
C3	0.051 (3)	0.062 (3)	0.067 (3)	0.011 (2)	0.014 (2)	0.021 (2)
C4	0.044 (3)	0.044 (2)	0.038 (2)	0.0074 (19)	0.006 (2)	0.0116 (19)
C5	0.055 (3)	0.064 (3)	0.037 (3)	0.002 (2)	0.012 (2)	0.011 (2)
C6	0.073 (4)	0.062 (3)	0.036 (3)	0.015 (3)	0.003 (3)	0.012 (2)
C7	0.057 (3)	0.054 (3)	0.037 (2)	0.015 (2)	0.002 (2)	0.0076 (18)
C8	0.070 (4)	0.113 (5)	0.055 (4)	0.038 (3)	−0.012 (3)	0.007 (3)
C9	0.037 (3)	0.061 (3)	0.043 (3)	0.010 (2)	0.008 (2)	0.011 (2)
C10	0.045 (3)	0.041 (2)	0.0334 (19)	0.0039 (18)	0.0076 (18)	0.0065 (16)
C11	0.045 (3)	0.050 (2)	0.041 (2)	0.0070 (19)	0.0072 (19)	0.0140 (18)
C12	0.056 (3)	0.068 (3)	0.055 (3)	0.022 (3)	0.024 (3)	0.028 (2)
C13	0.063 (3)	0.059 (3)	0.042 (2)	0.015 (2)	0.013 (2)	0.021 (2)
C14	0.054 (3)	0.041 (2)	0.036 (2)	0.008 (2)	0.007 (2)	0.0124 (17)
C15	0.066 (3)	0.062 (3)	0.039 (3)	0.019 (2)	−0.003 (2)	0.011 (2)
C16	0.054 (3)	0.068 (3)	0.037 (3)	0.013 (2)	0.005 (2)	0.019 (2)
C17	0.053 (3)	0.072 (3)	0.050 (3)	0.001 (2)	−0.002 (2)	0.018 (2)
C18	0.070 (4)	0.068 (3)	0.036 (3)	0.012 (3)	0.004 (3)	0.020 (2)
C19	0.078 (4)	0.063 (3)	0.046 (3)	0.006 (3)	−0.003 (3)	0.019 (2)
C20	0.064 (3)	0.064 (3)	0.047 (3)	0.009 (2)	0.001 (2)	0.021 (2)
C21	0.052 (3)	0.046 (2)	0.036 (2)	−0.001 (2)	0.004 (2)	0.0097 (18)
C22	0.064 (3)	0.053 (3)	0.034 (2)	0.010 (2)	0.018 (2)	0.0109 (19)
C23	0.072 (4)	0.043 (3)	0.053 (3)	0.017 (2)	0.025 (3)	0.015 (2)
C24	0.050 (3)	0.044 (2)	0.034 (2)	0.0030 (18)	0.0106 (18)	0.0090 (16)
C25	0.047 (3)	0.049 (2)	0.033 (2)	0.0101 (19)	0.0094 (18)	0.0146 (17)
C26	0.053 (3)	0.056 (3)	0.036 (2)	0.012 (2)	0.011 (2)	0.0127 (19)
C27	0.059 (3)	0.067 (3)	0.037 (2)	0.009 (2)	0.009 (2)	0.019 (2)
C28	0.068 (4)	0.124 (5)	0.037 (3)	0.022 (3)	0.005 (3)	0.029 (3)
C29	0.065 (4)	0.091 (4)	0.037 (3)	0.007 (3)	0.017 (3)	0.014 (3)
C30	0.061 (4)	0.087 (4)	0.042 (3)	0.012 (3)	0.016 (3)	0.010 (2)
C31	0.042 (3)	0.047 (3)	0.050 (3)	0.007 (2)	0.015 (2)	0.011 (2)
C32	0.044 (3)	0.071 (3)	0.057 (3)	0.017 (2)	0.015 (3)	0.028 (3)
C33	0.070 (4)	0.072 (4)	0.125 (5)	0.021 (3)	0.020 (4)	0.043 (3)
C34	0.056 (3)	0.064 (3)	0.074 (4)	0.015 (2)	−0.009 (3)	0.005 (3)

Br1—C13	1.890 (5)	C15—C16	1.502 (7)
Br2—C22	1.876 (5)	C15—H15A	0.9700
O1—C11	1.366 (5)	C15—H15B	0.9700
O1—C10	1.448 (5)	C16—C17	1.516 (7)
O2—C12	1.378 (6)	C16—H16A	0.9700
O2—C11	1.438 (5)	C16—H16B	0.9700
O3—C12	1.200 (6)	C17—C18	1.502 (6)
O4—C24	1.373 (5)	C17—H17A	0.9700
O4—C25	1.464 (5)	C17—H17B	0.9700
O5—C23	1.368 (5)	C18—C19	1.512 (6)
O5—C24	1.433 (5)	C18—H18A	0.9700
O6—C23	1.192 (6)	C18—H18B	0.9700
N1—C14	1.330 (5)	C19—C20	1.491 (7)
N1—C15	1.471 (6)	C19—H19A	0.9700
N1—H1	0.8600	C19—H19B	0.9700
N2—C21	1.337 (6)	C20—H20A	0.9700
N2—C20	1.482 (6)	C20—H20B	0.9700
N2—H2A	0.8600	C21—C22	1.335 (7)
C1—C2	1.526 (7)	C21—C24	1.535 (5)
C1—H1A	0.9600	C22—C23	1.454 (7)
C1—H1B	0.9600	C24—H24	0.9800
C1—H1C	0.9600	C25—C31	1.497 (6)
C2—C3	1.530 (7)	C25—C26	1.532 (6)
C2—C4	1.544 (7)	C25—H25	0.9800
C2—H2	0.9800	C26—C27	1.529 (6)
C3—H3A	0.9600	C26—H26A	0.9700
C3—H3B	0.9600	C26—H26B	0.9700
C3—H3C	0.9600	C27—C29	1.513 (9)
C4—C10	1.513 (6)	C27—C28	1.536 (7)
C4—C5	1.539 (7)	C27—H27	0.9800
C4—H4	0.9800	C28—H28A	0.9600
C5—C6	1.506 (9)	C28—H28B	0.9600
C5—H5A	0.9700	C28—H28C	0.9600
C5—H5B	0.9700	C29—C30	1.521 (9)
C6—C7	1.489 (8)	C29—H29A	0.9700
C6—H6A	0.9700	C29—H29B	0.9700
C6—H6B	0.9700	C30—C31	1.521 (7)
C7—C9	1.533 (6)	C30—H30A	0.9700
C7—C8	1.533 (7)	C30—H30B	0.9700
C7—H7	0.9800	C31—C32	1.544 (7)
C8—H8A	0.9600	C31—H31	0.9800
C8—H8B	0.9600	C32—C34	1.502 (7)
C8—H8C	0.9600	C32—C33	1.530 (7)
C9—C10	1.509 (6)	C32—H32	0.9800
C9—H9A	0.9700	C33—H33A	0.9600
C9—H9B	0.9700	C33—H33B	0.9600
C10—H10	0.9800	C33—H33C	0.9600
C11—C14	1.526 (5)	C34—H34A	0.9600
C11—H11	0.9800	C34—H34B	0.9600
C12—C13	1.429 (7)	C34—H34C	0.9600
C13—C14	1.339 (7)
C11—O1—C10	116.8 (3)	C18—C17—H17A	108.3
C12—O2—C11	109.9 (3)	C16—C17—H17A	108.3
C24—O4—C25	116.0 (3)	C18—C17—H17B	108.3
C23—O5—C24	109.9 (3)	C16—C17—H17B	108.3
C14—N1—C15	125.9 (4)	H17A—C17—H17B	107.4
C14—N1—H1	117.1	C17—C18—C19	112.2 (3)
C15—N1—H1	117.1	C17—C18—H18A	109.2
C21—N2—C20	126.3 (4)	C19—C18—H18A	109.2
C21—N2—H2A	116.9	C17—C18—H18B	109.2
C20—N2—H2A	116.9	C19—C18—H18B	109.2
C2—C1—H1A	109.5	H18A—C18—H18B	107.9
C2—C1—H1B	109.5	C20—C19—C18	114.4 (4)
H1A—C1—H1B	109.5	C20—C19—H19A	108.7
C2—C1—H1C	109.5	C18—C19—H19A	108.7
H1A—C1—H1C	109.5	C20—C19—H19B	108.7
H1B—C1—H1C	109.5	C18—C19—H19B	108.7
C1—C2—C3	109.2 (5)	H19A—C19—H19B	107.6
C1—C2—C4	114.2 (4)	N2—C20—C19	112.5 (4)
C3—C2—C4	110.5 (4)	N2—C20—H20A	109.1
C1—C2—H2	107.6	C19—C20—H20A	109.1
C3—C2—H2	107.6	N2—C20—H20B	109.1
C4—C2—H2	107.6	C19—C20—H20B	109.1
C2—C3—H3A	109.5	H20A—C20—H20B	107.8
C2—C3—H3B	109.5	C22—C21—N2	136.9 (4)
H3A—C3—H3B	109.5	C22—C21—C24	106.2 (4)
C2—C3—H3C	109.5	N2—C21—C24	116.9 (4)
H3A—C3—H3C	109.5	C21—C22—C23	111.1 (4)
H3B—C3—H3C	109.5	C21—C22—Br2	130.3 (4)
C10—C4—C5	109.4 (4)	C23—C22—Br2	118.6 (4)
C10—C4—C2	112.9 (4)	O6—C23—O5	121.9 (5)
C5—C4—C2	114.8 (4)	O6—C23—C22	130.5 (5)
C10—C4—H4	106.4	O5—C23—C22	107.5 (4)
C5—C4—H4	106.4	O4—C24—O5	113.3 (3)
C2—C4—H4	106.4	O4—C24—C21	109.9 (3)
C6—C5—C4	112.9 (5)	O5—C24—C21	104.5 (3)
C6—C5—H5A	109.0	O4—C24—H24	109.7
C4—C5—H5A	109.0	O5—C24—H24	109.7
C6—C5—H5B	109.0	C21—C24—H24	109.7
C4—C5—H5B	109.0	O4—C25—C31	107.8 (3)
H5A—C5—H5B	107.8	O4—C25—C26	109.0 (3)
C7—C6—C5	112.1 (5)	C31—C25—C26	113.2 (4)
C7—C6—H6A	109.2	O4—C25—H25	108.9
C5—C6—H6A	109.2	C31—C25—H25	108.9
C7—C6—H6B	109.2	C26—C25—H25	108.9
C5—C6—H6B	109.2	C27—C26—C25	112.9 (4)
H6A—C6—H6B	107.9	C27—C26—H26A	109.0
C6—C7—C9	109.5 (4)	C25—C26—H26A	109.0
C6—C7—C8	112.9 (4)	C27—C26—H26B	109.0
C9—C7—C8	111.6 (4)	C25—C26—H26B	109.0
C6—C7—H7	107.5	H26A—C26—H26B	107.8
C9—C7—H7	107.5	C29—C27—C26	109.8 (4)
C8—C7—H7	107.5	C29—C27—C28	112.7 (4)
C7—C8—H8A	109.5	C26—C27—C28	109.9 (4)
C7—C8—H8B	109.5	C29—C27—H27	108.1
H8A—C8—H8B	109.5	C26—C27—H27	108.1
C7—C8—H8C	109.5	C28—C27—H27	108.1
H8A—C8—H8C	109.5	C27—C28—H28A	109.5
H8B—C8—H8C	109.5	C27—C28—H28B	109.5
C10—C9—C7	113.1 (4)	H28A—C28—H28B	109.5
C10—C9—H9A	109.0	C27—C28—H28C	109.5
C7—C9—H9A	109.0	H28A—C28—H28C	109.5
C10—C9—H9B	109.0	H28B—C28—H28C	109.5
C7—C9—H9B	109.0	C27—C29—C30	112.2 (5)
H9A—C9—H9B	107.8	C27—C29—H29A	109.2
O1—C10—C9	111.5 (4)	C30—C29—H29A	109.2
O1—C10—C4	106.1 (3)	C27—C29—H29B	109.2
C9—C10—C4	112.8 (3)	C30—C29—H29B	109.2
O1—C10—H10	108.8	H29A—C29—H29B	107.9
C9—C10—H10	108.8	C29—C30—C31	112.2 (5)
C4—C10—H10	108.8	C29—C30—H30A	109.2
O1—C11—O2	111.5 (3)	C31—C30—H30A	109.2
O1—C11—C14	110.6 (3)	C29—C30—H30B	109.2
O2—C11—C14	103.8 (3)	C31—C30—H30B	109.2
O1—C11—H11	110.2	H30A—C30—H30B	107.9
O2—C11—H11	110.2	C25—C31—C30	109.6 (4)
C14—C11—H11	110.2	C25—C31—C32	114.7 (4)
O3—C12—O2	120.6 (5)	C30—C31—C32	112.5 (4)
O3—C12—C13	131.6 (5)	C25—C31—H31	106.5
O2—C12—C13	107.7 (4)	C30—C31—H31	106.5
C14—C13—C12	111.1 (4)	C32—C31—H31	106.5
C14—C13—Br1	130.3 (4)	C34—C32—C33	111.5 (5)
C12—C13—Br1	118.5 (4)	C34—C32—C31	114.3 (4)
N1—C14—C13	136.4 (4)	C33—C32—C31	112.0 (5)
N1—C14—C11	116.7 (4)	C34—C32—H32	106.1
C13—C14—C11	106.8 (4)	C33—C32—H32	106.1
N1—C15—C16	115.2 (4)	C31—C32—H32	106.1
N1—C15—H15A	108.5	C32—C33—H33A	109.5
C16—C15—H15A	108.5	C32—C33—H33B	109.5
N1—C15—H15B	108.5	H33A—C33—H33B	109.5
C16—C15—H15B	108.5	C32—C33—H33C	109.5
H15A—C15—H15B	107.5	H33A—C33—H33C	109.5
C15—C16—C17	110.0 (4)	H33B—C33—H33C	109.5
C15—C16—H16A	109.7	C32—C34—H34A	109.5
C17—C16—H16A	109.7	C32—C34—H34B	109.5
C15—C16—H16B	109.7	H34A—C34—H34B	109.5
C17—C16—H16B	109.7	C32—C34—H34C	109.5
H16A—C16—H16B	108.2	H34A—C34—H34C	109.5
C18—C17—C16	115.7 (4)	H34B—C34—H34C	109.5
C1—C2—C4—C10	−67.7 (6)	C17—C18—C19—C20	175.3 (5)
C3—C2—C4—C10	168.8 (4)	C21—N2—C20—C19	−82.3 (6)
C1—C2—C4—C5	58.7 (6)	C18—C19—C20—N2	177.8 (5)
C3—C2—C4—C5	−64.9 (5)	C20—N2—C21—C22	−11.8 (8)
C10—C4—C5—C6	−53.3 (5)	C20—N2—C21—C24	169.8 (4)
C2—C4—C5—C6	178.5 (4)	N2—C21—C22—C23	−172.6 (5)
C4—C5—C6—C7	57.0 (6)	C24—C21—C22—C23	5.8 (5)
C5—C6—C7—C9	−55.4 (6)	N2—C21—C22—Br2	7.6 (9)
C5—C6—C7—C8	179.6 (5)	C24—C21—C22—Br2	−173.9 (3)
C6—C7—C9—C10	54.3 (5)	C24—O5—C23—O6	177.1 (4)
C8—C7—C9—C10	−179.9 (4)	C24—O5—C23—C22	−4.6 (4)
C11—O1—C10—C9	−75.9 (5)	C21—C22—C23—O6	177.0 (5)
C11—O1—C10—C4	160.9 (3)	Br2—C22—C23—O6	−3.2 (7)
C7—C9—C10—O1	−173.2 (3)	C21—C22—C23—O5	−1.1 (5)
C7—C9—C10—C4	−53.9 (5)	Br2—C22—C23—O5	178.7 (3)
C5—C4—C10—O1	174.0 (4)	C25—O4—C24—O5	84.4 (4)
C2—C4—C10—O1	−56.8 (5)	C25—O4—C24—C21	−159.1 (3)
C5—C4—C10—C9	51.6 (5)	C23—O5—C24—O4	127.4 (3)
C2—C4—C10—C9	−179.2 (4)	C23—O5—C24—C21	7.8 (4)
C10—O1—C11—O2	90.3 (4)	C22—C21—C24—O4	−130.1 (4)
C10—O1—C11—C14	−154.7 (3)	N2—C21—C24—O4	48.7 (5)
C12—O2—C11—O1	124.9 (4)	C22—C21—C24—O5	−8.3 (4)
C12—O2—C11—C14	5.8 (4)	N2—C21—C24—O5	170.5 (3)
C11—O2—C12—O3	176.9 (5)	C24—O4—C25—C31	149.2 (3)
C11—O2—C12—C13	−2.2 (5)	C24—O4—C25—C26	−87.5 (4)
O3—C12—C13—C14	178.0 (6)	O4—C25—C26—C27	−173.0 (3)
O2—C12—C13—C14	−3.0 (5)	C31—C25—C26—C27	−53.1 (5)
O3—C12—C13—Br1	0.0 (8)	C25—C26—C27—C29	51.6 (5)
O2—C12—C13—Br1	179.0 (3)	C25—C26—C27—C28	176.1 (4)
C15—N1—C14—C13	−2.3 (8)	C26—C27—C29—C30	−53.9 (6)
C15—N1—C14—C11	173.3 (4)	C28—C27—C29—C30	−176.8 (5)
C12—C13—C14—N1	−177.6 (5)	C27—C29—C30—C31	57.4 (7)
Br1—C13—C14—N1	0.1 (9)	O4—C25—C31—C30	174.1 (3)
C12—C13—C14—C11	6.5 (5)	C26—C25—C31—C30	53.4 (5)
Br1—C13—C14—C11	−175.8 (3)	O4—C25—C31—C32	−58.3 (5)
O1—C11—C14—N1	55.9 (5)	C26—C25—C31—C32	−179.0 (4)
O2—C11—C14—N1	175.7 (4)	C29—C30—C31—C25	−55.6 (6)
O1—C11—C14—C13	−127.3 (4)	C29—C30—C31—C32	175.6 (5)
O2—C11—C14—C13	−7.5 (4)	C25—C31—C32—C34	−76.0 (6)
C14—N1—C15—C16	84.6 (6)	C30—C31—C32—C34	50.1 (6)
N1—C15—C16—C17	−177.4 (4)	C25—C31—C32—C33	156.0 (5)
C15—C16—C17—C18	−179.8 (4)	C30—C31—C32—C33	−77.9 (6)
C16—C17—C18—C19	178.0 (6)