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The regio-, relative, and absolute stereochemistry of the title compound, C38H40BrNO6, have been established. There are two independent mol­ecules in the asymmetric unit.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802006499/na6147sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802006499/na6147Isup2.hkl
Contains datablock I

CCDC reference: 185791

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.060
  • wR factor = 0.150
  • Data-to-parameter ratio = 12.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 10534 Count of symmetry unique reflns 5818 Completeness (_total/calc) 181.06% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 4716 Fraction of Friedel pairs measured 0.811 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.

Comment top

Recently, we reported a new rhodium-catalyzed ring opening reaction of a variety of oxabicyclic alkenes with a wide range of nucleophiles (Lautens & Fagnou, 2001). In particular, we found that N-methylaniline could be used to induce the enantioselective ring opening of 5,6-bis(4-methoxybenzyloxymethyl)-7-oxabicyclo[2.2.1]hept-2-ene. The 1,2-regio-, trans and relative stereochemistry, as well as the absolute stereochemistry, for this reaction were established by the X-ray diffraction analysis of the title compound, (I), when (R)-(-)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine [(R)-(S)-PPF-PtBu2] is used as the chiral ligand.

There are two independent molecules (A and B) in the asymmetric unit of the structure (see Figs. 1 and 2). An analysis (Cremer & Pople, 1975) of the puckering of the central cyclohexene ring (C1–C6) gives the total puckering amplitudes QT = 0.478 (6) Å for molecule A and QT = 0.480 (6) Å for molecule B. The conformation analysis of that ring (Duax et al., 1976) shows that the conformation is a half-chair, with a local pseudo-twofold axis running along the midpoints of the C1—C2 and C4—C5 bonds in both molecules.

Experimental top

The title compound was obtained as a white crystalline solid in 90% yield and 97% enantiomeric excess by treatment of (1R,2R,5R,6S)-5,6-bis-(4-methoxybenzyloxymethyl)-2-(methylphenylamino)- cyclohex-3-enol with 4-bromobenzoic acid chloride, pyridine and catalytic 4-(N,N-dimethylamino)pyridine in dichloromethane. Enantiomerically pure crystals were grown from pentane.

Refinement top

All H atoms were included in calculated positions, with C—H distances ranging from 0.95 to 1.00 Å, and then included in the refinement in riding-motion approximation, with Uiso = 1.2Ueq (1.5Ueq for methyl groups) of the carrier atom. 4722 Friedel pairs were used to determine the absolute stereochemistry.

Computing details top

Data collection: COLLECT (Nonius, 1997-2001); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXTL (Sheldrick, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. View of molecule A of (I) showing the crystallographic labelling scheme. Ellipsoids are at the 30% probability level.
[Figure 2] Fig. 2. View of molecule B of (I) showing the crystallographic labelling scheme. Ellipsoids are at the 30% probability level.
(1R,2R,5R,6S)-5,6-Bis(4-methoxybenzyloxymethyl)-2-(methylphenylamino)cyclohex- 3-enyl 4-bromobenzoate top
Crystal data top
C38H40BrNO6Z = 2
Mr = 686.62F(000) = 716
Triclinic, P1Dx = 1.384 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71070 Å
a = 7.8180 (2) ÅCell parameters from 5733 reflections
b = 11.2850 (3) Åθ = 2.5–25.0°
c = 18.6830 (5) ŵ = 1.30 mm1
α = 90.906 (1)°T = 150 K
β = 91.9660 (11)°Plate, colourless
γ = 90.0940 (14)°0.26 × 0.12 × 0.06 mm
V = 1647.15 (8) Å3
Data collection top
Nonius KappaCCD
diffractometer
10534 independent reflections
Radiation source: fine-focus sealed tube8339 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.081
Detector resolution: 9 pixels mm-1θmax = 25.0°, θmin = 2.6°
ϕ scans, and ω scans with κ offsetsh = 99
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
k = 1313
Tmin = 0.729, Tmax = 0.926l = 2222
19157 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.060 w = 1/[σ2(Fo2) + (0.0675P)2 + 0.8421P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.150(Δ/σ)max = 0.001
S = 1.03Δρmax = 1.85 e Å3
10534 reflectionsΔρmin = 0.41 e Å3
836 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
3 restraintsExtinction coefficient: 0.0064 (10)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.010 (9)
Crystal data top
C38H40BrNO6γ = 90.0940 (14)°
Mr = 686.62V = 1647.15 (8) Å3
Triclinic, P1Z = 2
a = 7.8180 (2) ÅMo Kα radiation
b = 11.2850 (3) ŵ = 1.30 mm1
c = 18.6830 (5) ÅT = 150 K
α = 90.906 (1)°0.26 × 0.12 × 0.06 mm
β = 91.9660 (11)°
Data collection top
Nonius KappaCCD
diffractometer
10534 independent reflections
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
8339 reflections with I > 2σ(I)
Tmin = 0.729, Tmax = 0.926Rint = 0.081
19157 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.150Δρmax = 1.85 e Å3
S = 1.03Δρmin = 0.41 e Å3
10534 reflectionsAbsolute structure: Flack (1983)
836 parametersAbsolute structure parameter: 0.010 (9)
3 restraints
Special details top

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 (Å2) top
xyzUiso*/Ueq
Br1A0.42758 (8)0.12021 (5)0.99509 (4)0.0492 (2)
C1A0.0218 (7)0.5099 (5)0.6636 (3)0.0248 (12)
H1AA0.04090.44680.63510.030*
C2A0.1431 (7)0.5734 (5)0.6145 (3)0.0266 (12)
H2AA0.21250.50990.59150.032*
C3A0.0339 (7)0.6298 (5)0.5528 (3)0.0278 (13)
H3AA0.00300.56310.51990.033*
C4A0.1281 (7)0.6866 (6)0.5788 (3)0.0288 (15)
H4AA0.18730.73910.54740.035*
C5A0.1932 (7)0.6683 (5)0.6422 (3)0.0265 (12)
H5AA0.29810.70590.65290.032*
C6A0.1091 (7)0.5909 (5)0.6983 (3)0.0233 (13)
H6AA0.04590.64390.73350.028*
N7A0.2374 (6)0.5255 (4)0.7371 (2)0.0251 (10)
C8A0.3391 (7)0.4408 (6)0.6934 (3)0.0334 (14)
H8AA0.45410.43490.71230.050*
H8AB0.28400.36290.69470.050*
H8AC0.34730.46810.64380.050*
C9A0.2076 (7)0.4994 (5)0.8100 (3)0.0283 (13)
C10A0.2763 (8)0.3981 (5)0.8399 (3)0.0319 (14)
H10A0.33810.34310.80990.038*
C11A0.2562 (9)0.3762 (6)0.9127 (4)0.0434 (17)
H11A0.30610.30740.93200.052*
C12A0.1632 (8)0.4545 (6)0.9572 (3)0.0380 (15)
H12A0.14740.43891.00680.046*
C13A0.0949 (8)0.5541 (6)0.9289 (4)0.0338 (15)
H13A0.03100.60730.95930.041*
C14A0.1165 (7)0.5794 (5)0.8565 (3)0.0271 (14)
H14A0.07010.65020.83830.033*
C15A0.2706 (7)0.6548 (5)0.6536 (3)0.0290 (13)
H15A0.32720.61100.69330.035*
H15B0.35980.67800.62020.035*
O16A0.1930 (5)0.7595 (3)0.6820 (2)0.0317 (9)
C17A0.3116 (8)0.8250 (5)0.7280 (3)0.0341 (14)
H17A0.27810.90960.72840.041*
H17B0.42720.81940.70820.041*
C18A0.3183 (7)0.7812 (5)0.8033 (3)0.0288 (13)
C19A0.4231 (8)0.6881 (6)0.8256 (4)0.0310 (15)
H19A0.49690.65290.79200.037*
C20A0.4245 (8)0.6449 (6)0.8941 (4)0.0345 (16)
H20A0.49670.58070.90730.041*
C21A0.3185 (9)0.6970 (7)0.9435 (3)0.0435 (17)
C22A0.2162 (9)0.7923 (7)0.9234 (4)0.0464 (18)
H22A0.14620.82980.95760.056*
C23A0.2157 (8)0.8322 (6)0.8549 (4)0.0428 (17)
H23A0.14340.89660.84190.051*
O24A0.3046 (7)0.6618 (6)1.0125 (3)0.0673 (16)
C25A0.4154 (14)0.5709 (10)1.0377 (5)0.074 (3)
H25A0.40470.56291.08950.111*
H25B0.53390.59121.02730.111*
H25C0.38420.49581.01350.111*
C26A0.1343 (7)0.7138 (5)0.5086 (3)0.0307 (13)
H26A0.06310.74080.46720.037*
H26B0.16970.78410.53790.037*
O27A0.2811 (5)0.6528 (4)0.4843 (2)0.0382 (11)
C28A0.3958 (8)0.7281 (7)0.4467 (4)0.0405 (18)
H28A0.51070.69120.44750.049*
H28B0.40590.80510.47260.049*
C29A0.3412 (7)0.7501 (5)0.3709 (3)0.0311 (14)
C30A0.3790 (8)0.6677 (6)0.3176 (4)0.0386 (18)
H30A0.43170.59470.33020.046*
C31A0.3406 (9)0.6912 (6)0.2467 (4)0.0417 (17)
H31A0.36830.63410.21100.050*
C32A0.2624 (8)0.7966 (6)0.2261 (3)0.0337 (14)
C33A0.2156 (7)0.8764 (5)0.2782 (3)0.0310 (13)
H33A0.15490.94640.26570.037*
C34A0.2587 (7)0.8533 (5)0.3504 (3)0.0317 (14)
H34A0.23050.91020.38610.038*
O35A0.2404 (6)0.8124 (4)0.1544 (2)0.0473 (12)
C36A0.1474 (12)0.9126 (7)0.1323 (4)0.058 (2)
H36A0.13440.91180.08000.086*
H36B0.20880.98450.14840.086*
H36C0.03420.91130.15320.086*
O37A0.1136 (5)0.4548 (3)0.7229 (2)0.0262 (9)
C38A0.1886 (7)0.3490 (5)0.7131 (3)0.0260 (13)
O39A0.2001 (6)0.3012 (4)0.6540 (2)0.0394 (11)
C40A0.2543 (7)0.2985 (5)0.7814 (3)0.0280 (13)
C41A0.2114 (7)0.3490 (5)0.8472 (3)0.0297 (13)
H41A0.14630.41990.84850.036*
C42A0.2636 (7)0.2957 (5)0.9105 (3)0.0321 (14)
H42A0.23530.32990.95540.039*
C43A0.3575 (8)0.1919 (5)0.9077 (3)0.0345 (14)
C44A0.4039 (8)0.1412 (6)0.8427 (4)0.0332 (16)
H44A0.47130.07130.84150.040*
C45A0.3505 (7)0.1942 (5)0.7806 (3)0.0317 (14)
H45A0.37940.15940.73600.038*
Br1B0.87576 (8)0.64358 (5)0.15048 (4)0.0500 (2)
C1B0.5075 (7)0.2554 (5)0.4790 (3)0.0247 (12)
H1BA0.44980.31850.50750.030*
C2B0.6358 (7)0.1910 (5)0.5283 (3)0.0242 (12)
H2BA0.70930.25420.55160.029*
C3B0.5363 (7)0.1346 (5)0.5892 (3)0.0265 (12)
H3BA0.50580.20120.62230.032*
C4B0.3690 (7)0.0783 (5)0.5638 (3)0.0271 (14)
H4BA0.31430.02650.59550.032*
C5B0.2935 (7)0.0962 (5)0.5005 (3)0.0290 (13)
H5BA0.18650.05870.48990.035*
C6B0.3688 (7)0.1729 (5)0.4442 (3)0.0234 (13)
H6BA0.42680.11930.40960.028*
N7B0.2367 (6)0.2389 (4)0.4036 (3)0.0272 (10)
C8B0.1419 (8)0.3239 (6)0.4470 (4)0.0377 (16)
H8BA0.02660.33410.42580.057*
H8BB0.20190.40020.44860.057*
H8BC0.13380.29410.49580.057*
C9B0.2558 (7)0.2631 (5)0.3319 (3)0.0256 (12)
C10B0.1820 (8)0.3649 (5)0.3005 (4)0.0349 (14)
H10B0.12290.41990.32960.042*
C11B0.1942 (9)0.3860 (6)0.2282 (4)0.0426 (16)
H11B0.14320.45550.20900.051*
C12B0.2781 (8)0.3095 (6)0.1830 (3)0.0355 (14)
H12B0.28450.32460.13320.043*
C13B0.3529 (8)0.2094 (6)0.2131 (4)0.0337 (15)
H13B0.41180.15540.18330.040*
C14B0.3436 (8)0.1868 (6)0.2850 (3)0.0317 (14)
H14B0.39770.11800.30360.038*
C15B0.7563 (7)0.1098 (5)0.4890 (3)0.0265 (12)
H15C0.80660.15380.44930.032*
H15D0.85100.08630.52230.032*
O16B0.6729 (5)0.0051 (3)0.4604 (2)0.0267 (9)
C17B0.7833 (7)0.0616 (5)0.4150 (3)0.0302 (13)
H17C0.74790.14590.41460.036*
H17D0.90200.05680.43500.036*
C18B0.7800 (7)0.0180 (5)0.3391 (3)0.0238 (12)
C19B0.8826 (8)0.0765 (6)0.3180 (3)0.0276 (14)
H19B0.96060.11280.35180.033*
C20B0.8715 (9)0.1174 (6)0.2488 (4)0.0333 (15)
H20B0.94160.18140.23520.040*
C21B0.7573 (8)0.0647 (6)0.1989 (3)0.0330 (14)
C22B0.6588 (8)0.0300 (6)0.2185 (3)0.0361 (15)
H22B0.58330.06740.18410.043*
C23B0.6694 (8)0.0707 (6)0.2878 (3)0.0340 (14)
H23B0.60020.13570.30070.041*
O24B0.7365 (6)0.0991 (4)0.1282 (2)0.0421 (11)
C25B0.8477 (11)0.1877 (7)0.1034 (4)0.049 (2)
H25D0.81720.20520.05340.073*
H25E0.96610.15940.10690.073*
H25F0.83670.25990.13280.073*
C26B0.6440 (7)0.0491 (5)0.6336 (3)0.0309 (13)
H26C0.57920.02160.67480.037*
H26D0.67470.02080.60410.037*
O27B0.7950 (5)0.1108 (4)0.6582 (2)0.0342 (10)
C28B0.9146 (8)0.0359 (6)0.6945 (4)0.0348 (16)
H28C1.02960.07270.69360.042*
H28D0.91960.04080.66830.042*
C29B0.8720 (7)0.0129 (5)0.7718 (3)0.0274 (13)
C30B0.9225 (8)0.0961 (6)0.8256 (4)0.0331 (16)
H30B0.97550.16800.81250.040*
C31B0.8967 (8)0.0751 (6)0.8969 (4)0.0333 (15)
H31B0.93290.13160.93250.040*
C32B0.8176 (7)0.0290 (5)0.9164 (3)0.0296 (13)
C33B0.7622 (7)0.1109 (5)0.8649 (3)0.0310 (13)
H33B0.70530.18120.87830.037*
C34B0.7912 (8)0.0889 (5)0.7928 (3)0.0331 (14)
H34B0.75420.14560.75740.040*
O35B0.8076 (6)0.0440 (4)0.9888 (2)0.0375 (10)
C36B0.7122 (10)0.1436 (6)1.0116 (4)0.0474 (18)
H36D0.71620.14601.06410.071*
H36E0.76190.21660.99230.071*
H36F0.59300.13680.99420.071*
O37B0.5885 (5)0.3099 (3)0.4195 (2)0.0278 (9)
C38B0.6652 (7)0.4168 (5)0.4309 (3)0.0291 (13)
O39B0.6840 (6)0.4646 (4)0.4888 (2)0.0381 (10)
C40B0.7215 (7)0.4668 (5)0.3620 (3)0.0271 (12)
C41B0.6731 (7)0.4152 (5)0.2960 (3)0.0310 (14)
H41B0.61010.34310.29400.037*
C42B0.7179 (8)0.4702 (5)0.2332 (3)0.0331 (14)
H42B0.68220.43740.18800.040*
C43B0.8149 (8)0.5729 (5)0.2371 (4)0.0347 (15)
C44B0.8648 (8)0.6242 (6)0.3014 (4)0.0330 (16)
H44B0.93090.69500.30280.040*
C45B0.8179 (7)0.5717 (5)0.3649 (4)0.0333 (14)
H45B0.85090.60690.40980.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br1A0.0582 (5)0.0503 (5)0.0395 (4)0.0114 (4)0.0021 (3)0.0167 (3)
C1A0.026 (3)0.024 (3)0.024 (3)0.002 (2)0.002 (2)0.004 (2)
C2A0.024 (3)0.028 (3)0.029 (3)0.003 (2)0.003 (2)0.003 (2)
C3A0.026 (3)0.028 (3)0.030 (3)0.001 (2)0.002 (2)0.007 (2)
C4A0.020 (3)0.039 (4)0.028 (3)0.004 (3)0.003 (2)0.008 (3)
C5A0.024 (3)0.022 (3)0.034 (3)0.000 (2)0.003 (2)0.002 (2)
C6A0.018 (3)0.027 (3)0.025 (3)0.001 (2)0.002 (2)0.000 (3)
N7A0.023 (2)0.028 (3)0.024 (3)0.007 (2)0.0039 (19)0.003 (2)
C8A0.027 (3)0.035 (3)0.039 (4)0.004 (3)0.003 (3)0.000 (3)
C9A0.028 (3)0.022 (3)0.035 (3)0.004 (2)0.007 (2)0.002 (2)
C10A0.032 (3)0.024 (3)0.040 (4)0.004 (3)0.000 (3)0.007 (3)
C11A0.046 (4)0.037 (4)0.048 (4)0.002 (3)0.006 (3)0.018 (3)
C12A0.046 (4)0.040 (4)0.029 (3)0.005 (3)0.003 (3)0.005 (3)
C13A0.034 (4)0.031 (4)0.036 (4)0.007 (3)0.003 (3)0.001 (3)
C14A0.021 (3)0.030 (3)0.030 (3)0.004 (3)0.005 (2)0.001 (3)
C15A0.017 (3)0.033 (3)0.037 (3)0.005 (2)0.000 (2)0.002 (3)
O16A0.025 (2)0.028 (2)0.041 (3)0.0009 (17)0.0073 (18)0.0007 (19)
C17A0.028 (3)0.026 (3)0.047 (4)0.007 (3)0.012 (3)0.001 (3)
C18A0.022 (3)0.027 (3)0.037 (3)0.005 (2)0.006 (2)0.004 (3)
C19A0.029 (3)0.028 (4)0.036 (4)0.000 (3)0.003 (3)0.003 (3)
C20A0.030 (4)0.033 (4)0.040 (4)0.004 (3)0.005 (3)0.002 (3)
C21A0.048 (4)0.053 (4)0.029 (4)0.006 (3)0.000 (3)0.010 (3)
C22A0.037 (4)0.064 (5)0.039 (4)0.010 (3)0.004 (3)0.018 (4)
C23A0.032 (4)0.039 (4)0.056 (5)0.007 (3)0.002 (3)0.017 (3)
O24A0.065 (4)0.104 (5)0.032 (3)0.002 (3)0.001 (2)0.002 (3)
C25A0.100 (8)0.086 (8)0.036 (5)0.020 (6)0.006 (5)0.008 (5)
C26A0.024 (3)0.033 (3)0.036 (3)0.007 (2)0.006 (2)0.008 (3)
O27A0.029 (2)0.041 (3)0.046 (3)0.0063 (19)0.0103 (19)0.018 (2)
C28A0.029 (4)0.041 (4)0.053 (5)0.000 (3)0.012 (3)0.017 (4)
C29A0.020 (3)0.032 (3)0.042 (4)0.007 (3)0.008 (3)0.010 (3)
C30A0.029 (3)0.028 (4)0.060 (5)0.000 (3)0.006 (3)0.001 (4)
C31A0.038 (4)0.039 (4)0.048 (4)0.000 (3)0.000 (3)0.008 (3)
C32A0.030 (3)0.038 (4)0.033 (3)0.008 (3)0.002 (3)0.002 (3)
C33A0.031 (3)0.029 (3)0.033 (3)0.004 (2)0.007 (3)0.000 (3)
C34A0.032 (3)0.028 (3)0.035 (3)0.001 (3)0.010 (3)0.001 (3)
O35A0.052 (3)0.052 (3)0.037 (3)0.003 (2)0.004 (2)0.006 (2)
C36A0.089 (6)0.052 (5)0.031 (4)0.015 (4)0.001 (4)0.007 (3)
O37A0.030 (2)0.022 (2)0.027 (2)0.0060 (17)0.0024 (17)0.0032 (17)
C38A0.017 (3)0.022 (3)0.039 (4)0.002 (2)0.007 (2)0.003 (3)
O39A0.050 (3)0.035 (2)0.033 (3)0.015 (2)0.002 (2)0.001 (2)
C40A0.024 (3)0.024 (3)0.037 (3)0.000 (2)0.004 (2)0.006 (3)
C41A0.028 (3)0.025 (3)0.036 (3)0.004 (2)0.001 (3)0.002 (3)
C42A0.032 (3)0.035 (3)0.029 (3)0.001 (3)0.004 (3)0.003 (3)
C43A0.032 (3)0.032 (3)0.040 (4)0.005 (3)0.001 (3)0.007 (3)
C44A0.020 (3)0.036 (4)0.044 (4)0.002 (3)0.004 (3)0.000 (3)
C45A0.027 (3)0.030 (3)0.039 (4)0.001 (3)0.008 (3)0.006 (3)
Br1B0.0638 (5)0.0461 (4)0.0403 (4)0.0138 (3)0.0036 (3)0.0176 (3)
C1B0.023 (3)0.024 (3)0.027 (3)0.006 (2)0.004 (2)0.001 (2)
C2B0.022 (3)0.024 (3)0.027 (3)0.002 (2)0.001 (2)0.004 (2)
C3B0.024 (3)0.035 (3)0.021 (3)0.000 (2)0.004 (2)0.001 (2)
C4B0.022 (3)0.024 (3)0.035 (4)0.006 (2)0.007 (3)0.003 (3)
C5B0.025 (3)0.029 (3)0.034 (3)0.001 (2)0.009 (2)0.000 (3)
C6B0.024 (3)0.018 (3)0.028 (3)0.001 (2)0.000 (2)0.003 (3)
N7B0.022 (2)0.028 (3)0.032 (3)0.004 (2)0.001 (2)0.002 (2)
C8B0.035 (4)0.039 (4)0.040 (4)0.012 (3)0.002 (3)0.009 (3)
C9B0.024 (3)0.020 (3)0.031 (3)0.004 (2)0.005 (2)0.006 (2)
C10B0.034 (3)0.028 (3)0.043 (4)0.003 (3)0.001 (3)0.004 (3)
C11B0.051 (4)0.033 (4)0.044 (4)0.003 (3)0.000 (3)0.014 (3)
C12B0.037 (3)0.042 (4)0.028 (3)0.006 (3)0.007 (3)0.006 (3)
C13B0.035 (4)0.033 (4)0.032 (4)0.000 (3)0.002 (3)0.005 (3)
C14B0.036 (4)0.029 (3)0.030 (4)0.000 (3)0.006 (3)0.002 (3)
C15B0.028 (3)0.025 (3)0.027 (3)0.002 (2)0.003 (2)0.000 (2)
O16B0.026 (2)0.025 (2)0.029 (2)0.0008 (16)0.0060 (16)0.0016 (17)
C17B0.030 (3)0.029 (3)0.032 (3)0.002 (3)0.005 (3)0.005 (3)
C18B0.020 (3)0.029 (3)0.023 (3)0.003 (2)0.006 (2)0.002 (2)
C19B0.024 (3)0.032 (4)0.026 (4)0.005 (3)0.002 (3)0.002 (3)
C20B0.040 (4)0.030 (4)0.030 (4)0.004 (3)0.005 (3)0.002 (3)
C21B0.042 (4)0.038 (4)0.019 (3)0.000 (3)0.005 (3)0.001 (3)
C22B0.030 (3)0.044 (4)0.033 (4)0.009 (3)0.003 (3)0.004 (3)
C23B0.032 (3)0.032 (3)0.038 (4)0.003 (3)0.010 (3)0.002 (3)
O24B0.041 (3)0.056 (3)0.029 (2)0.011 (2)0.0006 (19)0.003 (2)
C25B0.079 (6)0.040 (4)0.028 (4)0.004 (4)0.006 (4)0.012 (3)
C26B0.027 (3)0.035 (3)0.031 (3)0.007 (3)0.007 (2)0.005 (3)
O27B0.033 (2)0.034 (2)0.035 (2)0.0015 (18)0.0035 (18)0.0080 (19)
C28B0.031 (4)0.046 (4)0.027 (4)0.003 (3)0.004 (3)0.006 (3)
C29B0.018 (3)0.029 (3)0.035 (3)0.002 (2)0.001 (2)0.001 (3)
C30B0.037 (4)0.024 (3)0.039 (4)0.005 (3)0.004 (3)0.003 (3)
C31B0.030 (3)0.029 (3)0.040 (4)0.008 (3)0.002 (3)0.010 (3)
C32B0.028 (3)0.034 (3)0.027 (3)0.003 (3)0.001 (2)0.000 (3)
C33B0.031 (3)0.027 (3)0.035 (3)0.000 (3)0.001 (3)0.001 (3)
C34B0.038 (3)0.026 (3)0.034 (3)0.002 (3)0.011 (3)0.003 (3)
O35B0.043 (3)0.038 (2)0.032 (2)0.001 (2)0.0026 (19)0.0007 (19)
C36B0.064 (5)0.040 (4)0.040 (4)0.004 (3)0.012 (3)0.013 (3)
O37B0.031 (2)0.026 (2)0.026 (2)0.0084 (17)0.0000 (17)0.0025 (17)
C38B0.026 (3)0.023 (3)0.038 (4)0.002 (2)0.000 (3)0.005 (3)
O39B0.048 (3)0.034 (2)0.032 (3)0.012 (2)0.005 (2)0.005 (2)
C40B0.028 (3)0.021 (3)0.032 (3)0.004 (2)0.002 (2)0.001 (2)
C41B0.032 (3)0.024 (3)0.037 (4)0.010 (3)0.003 (3)0.002 (3)
C42B0.038 (4)0.030 (3)0.031 (3)0.001 (3)0.000 (3)0.001 (3)
C43B0.029 (3)0.031 (3)0.045 (4)0.003 (3)0.002 (3)0.011 (3)
C44B0.041 (4)0.021 (3)0.037 (4)0.006 (3)0.007 (3)0.005 (3)
C45B0.026 (3)0.030 (3)0.044 (4)0.007 (3)0.004 (3)0.004 (3)
Geometric parameters (Å, º) top
Br1A—C43A1.898 (6)Br1B—C43B1.890 (6)
C1A—O37A1.448 (6)C1B—O37B1.444 (6)
C1A—C6A1.527 (8)C1B—C2B1.530 (7)
C1A—C2A1.528 (7)C1B—C6B1.547 (8)
C1A—H1AA1.0000C1B—H1BA1.0000
C2A—C15A1.515 (8)C2B—C15B1.515 (8)
C2A—C3A1.555 (8)C2B—C3B1.544 (7)
C2A—H2AA1.0000C2B—H2BA1.0000
C3A—C26A1.504 (8)C3B—C4B1.512 (8)
C3A—C4A1.512 (8)C3B—C26B1.520 (8)
C3A—H3AA1.0000C3B—H3BA1.0000
C4A—C5A1.324 (9)C4B—C5B1.323 (9)
C4A—H4AA0.9500C4B—H4BA0.9500
C5A—C6A1.509 (8)C5B—C6B1.507 (8)
C5A—H5AA0.9500C5B—H5BA0.9500
C6A—N7A1.464 (7)C6B—N7B1.471 (7)
C6A—H6AA1.0000C6B—H6BA1.0000
N7A—C9A1.409 (7)N7B—C9B1.385 (7)
N7A—C8A1.463 (8)N7B—C8B1.465 (8)
C8A—H8AA0.9800C8B—H8BA0.9800
C8A—H8AB0.9800C8B—H8BB0.9800
C8A—H8AC0.9800C8B—H8BC0.9800
C9A—C10A1.395 (8)C9B—C10B1.414 (8)
C9A—C14A1.417 (9)C9B—C14B1.414 (8)
C10A—C11A1.390 (9)C10B—C11B1.382 (9)
C10A—H10A0.9500C10B—H10B0.9500
C11A—C12A1.392 (10)C11B—C12B1.381 (9)
C11A—H11A0.9500C11B—H11B0.9500
C12A—C13A1.366 (9)C12B—C13B1.390 (9)
C12A—H12A0.9500C12B—H12B0.9500
C13A—C14A1.391 (9)C13B—C14B1.375 (9)
C13A—H13A0.9500C13B—H13B0.9500
C14A—H14A0.9500C14B—H14B0.9500
C15A—O16A1.432 (7)C15B—O16B1.436 (7)
C15A—H15A0.9900C15B—H15C0.9900
C15A—H15B0.9900C15B—H15D0.9900
O16A—C17A1.437 (7)O16B—C17B1.437 (7)
C17A—C18A1.499 (9)C17B—C18B1.507 (8)
C17A—H17A0.9900C17B—H17C0.9900
C17A—H17B0.9900C17B—H17D0.9900
C18A—C23A1.392 (9)C18B—C23B1.394 (8)
C18A—C19A1.394 (9)C18B—C19B1.403 (8)
C19A—C20A1.376 (10)C19B—C20B1.380 (9)
C19A—H19A0.9500C19B—H19B0.9500
C20A—C21A1.386 (10)C20B—C21B1.394 (9)
C20A—H20A0.9500C20B—H20B0.9500
C21A—O24A1.363 (8)C21B—C22B1.378 (9)
C21A—C22A1.390 (10)C21B—O24B1.387 (7)
C22A—C23A1.364 (10)C22B—C23B1.381 (9)
C22A—H22A0.9500C22B—H22B0.9500
C23A—H23A0.9500C23B—H23B0.9500
O24A—C25A1.419 (12)O24B—C25B1.418 (9)
C25A—H25A0.9800C25B—H25D0.9800
C25A—H25B0.9800C25B—H25E0.9800
C25A—H25C0.9800C25B—H25F0.9800
C26A—O27A1.423 (7)C26B—O27B1.428 (7)
C26A—H26A0.9900C26B—H26C0.9900
C26A—H26B0.9900C26B—H26D0.9900
O27A—C28A1.442 (8)O27B—C28B1.424 (7)
C28A—C29A1.491 (10)C28B—C29B1.519 (9)
C28A—H28A0.9900C28B—H28C0.9900
C28A—H28B0.9900C28B—H28D0.9900
C29A—C34A1.385 (8)C29B—C34B1.379 (8)
C29A—C30A1.391 (10)C29B—C30B1.411 (9)
C30A—C31A1.378 (11)C30B—C31B1.378 (10)
C30A—H30A0.9500C30B—H30B0.9500
C31A—C32A1.392 (9)C31B—C32B1.385 (9)
C31A—H31A0.9500C31B—H31B0.9500
C32A—O35A1.360 (8)C32B—O35B1.372 (7)
C32A—C33A1.375 (9)C32B—C33B1.382 (8)
C33A—C34A1.407 (9)C33B—C34B1.400 (9)
C33A—H33A0.9500C33B—H33B0.9500
C34A—H34A0.9500C34B—H34B0.9500
O35A—C36A1.404 (9)O35B—C36B1.428 (8)
C36A—H36A0.9800C36B—H36D0.9800
C36A—H36B0.9800C36B—H36E0.9800
C36A—H36C0.9800C36B—H36F0.9800
O37A—C38A1.345 (7)O37B—C38B1.357 (7)
C38A—O39A1.226 (7)C38B—O39B1.204 (7)
C38A—C40A1.482 (8)C38B—C40B1.493 (8)
C40A—C45A1.399 (8)C40B—C41B1.396 (8)
C40A—C41A1.399 (8)C40B—C45B1.402 (8)
C41A—C42A1.385 (8)C41B—C42B1.391 (8)
C41A—H41A0.9500C41B—H41B0.9500
C42A—C43A1.384 (9)C42B—C43B1.383 (9)
C42A—H42A0.9500C42B—H42B0.9500
C43A—C44A1.394 (9)C43B—C44B1.371 (9)
C44A—C45A1.365 (9)C44B—C45B1.394 (9)
C44A—H44A0.9500C44B—H44B0.9500
C45A—H45A0.9500C45B—H45B0.9500
O37A—C1A—C6A105.0 (4)O37B—C1B—C2B112.4 (4)
O37A—C1A—C2A111.7 (4)O37B—C1B—C6B104.8 (4)
C6A—C1A—C2A114.2 (5)C2B—C1B—C6B113.6 (4)
O37A—C1A—H1AA108.6O37B—C1B—H1BA108.6
C6A—C1A—H1AA108.6C2B—C1B—H1BA108.6
C2A—C1A—H1AA108.6C6B—C1B—H1BA108.6
C15A—C2A—C1A114.0 (5)C15B—C2B—C1B113.8 (5)
C15A—C2A—C3A116.2 (5)C15B—C2B—C3B116.2 (5)
C1A—C2A—C3A108.1 (4)C1B—C2B—C3B108.2 (4)
C15A—C2A—H2AA105.9C15B—C2B—H2BA105.9
C1A—C2A—H2AA105.9C1B—C2B—H2BA105.9
C3A—C2A—H2AA105.9C3B—C2B—H2BA105.9
C26A—C3A—C4A111.5 (5)C4B—C3B—C26B111.2 (5)
C26A—C3A—C2A113.1 (5)C4B—C3B—C2B113.3 (5)
C4A—C3A—C2A112.6 (5)C26B—C3B—C2B113.0 (4)
C26A—C3A—H3AA106.4C4B—C3B—H3BA106.2
C4A—C3A—H3AA106.4C26B—C3B—H3BA106.2
C2A—C3A—H3AA106.4C2B—C3B—H3BA106.2
C5A—C4A—C3A124.6 (6)C5B—C4B—C3B124.5 (5)
C5A—C4A—H4AA117.7C5B—C4B—H4BA117.8
C3A—C4A—H4AA117.7C3B—C4B—H4BA117.8
C4A—C5A—C6A123.3 (6)C4B—C5B—C6B123.3 (5)
C4A—C5A—H5AA118.3C4B—C5B—H5BA118.4
C6A—C5A—H5AA118.3C6B—C5B—H5BA118.4
N7A—C6A—C5A110.9 (5)N7B—C6B—C5B112.2 (5)
N7A—C6A—C1A112.8 (5)N7B—C6B—C1B112.4 (5)
C5A—C6A—C1A109.8 (5)C5B—C6B—C1B109.9 (5)
N7A—C6A—H6AA107.7N7B—C6B—H6BA107.4
C5A—C6A—H6AA107.7C5B—C6B—H6BA107.4
C1A—C6A—H6AA107.7C1B—C6B—H6BA107.4
C9A—N7A—C8A117.7 (5)C9B—N7B—C8B118.2 (5)
C9A—N7A—C6A120.0 (5)C9B—N7B—C6B120.8 (5)
C8A—N7A—C6A114.8 (5)C8B—N7B—C6B114.0 (5)
N7A—C8A—H8AA109.5N7B—C8B—H8BA109.5
N7A—C8A—H8AB109.5N7B—C8B—H8BB109.5
H8AA—C8A—H8AB109.5H8BA—C8B—H8BB109.5
N7A—C8A—H8AC109.5N7B—C8B—H8BC109.5
H8AA—C8A—H8AC109.5H8BA—C8B—H8BC109.5
H8AB—C8A—H8AC109.5H8BB—C8B—H8BC109.5
C10A—C9A—N7A121.2 (5)N7B—C9B—C10B121.3 (5)
C10A—C9A—C14A117.6 (6)N7B—C9B—C14B122.9 (5)
N7A—C9A—C14A121.0 (5)C10B—C9B—C14B115.8 (6)
C11A—C10A—C9A121.3 (6)C11B—C10B—C9B121.2 (6)
C11A—C10A—H10A119.3C11B—C10B—H10B119.4
C9A—C10A—H10A119.3C9B—C10B—H10B119.4
C10A—C11A—C12A120.2 (6)C12B—C11B—C10B122.2 (6)
C10A—C11A—H11A119.9C12B—C11B—H11B118.9
C12A—C11A—H11A119.9C10B—C11B—H11B118.9
C13A—C12A—C11A119.3 (6)C11B—C12B—C13B117.3 (6)
C13A—C12A—H12A120.4C11B—C12B—H12B121.3
C11A—C12A—H12A120.4C13B—C12B—H12B121.3
C12A—C13A—C14A121.6 (6)C14B—C13B—C12B121.6 (6)
C12A—C13A—H13A119.2C14B—C13B—H13B119.2
C14A—C13A—H13A119.2C12B—C13B—H13B119.2
C13A—C14A—C9A119.9 (6)C13B—C14B—C9B121.8 (6)
C13A—C14A—H14A120.0C13B—C14B—H14B119.1
C9A—C14A—H14A120.0C9B—C14B—H14B119.1
O16A—C15A—C2A112.9 (4)O16B—C15B—C2B112.7 (4)
O16A—C15A—H15A109.0O16B—C15B—H15C109.0
C2A—C15A—H15A109.0C2B—C15B—H15C109.0
O16A—C15A—H15B109.0O16B—C15B—H15D109.0
C2A—C15A—H15B109.0C2B—C15B—H15D109.0
H15A—C15A—H15B107.8H15C—C15B—H15D107.8
C15A—O16A—C17A111.3 (4)C15B—O16B—C17B111.5 (4)
O16A—C17A—C18A112.8 (5)O16B—C17B—C18B112.8 (4)
O16A—C17A—H17A109.0O16B—C17B—H17C109.0
C18A—C17A—H17A109.0C18B—C17B—H17C109.0
O16A—C17A—H17B109.0O16B—C17B—H17D109.0
C18A—C17A—H17B109.0C18B—C17B—H17D109.0
H17A—C17A—H17B107.8H17C—C17B—H17D107.8
C23A—C18A—C19A116.6 (6)C23B—C18B—C19B118.1 (5)
C23A—C18A—C17A120.5 (6)C23B—C18B—C17B119.7 (5)
C19A—C18A—C17A122.9 (6)C19B—C18B—C17B122.3 (5)
C20A—C19A—C18A122.9 (6)C20B—C19B—C18B120.8 (6)
C20A—C19A—H19A118.6C20B—C19B—H19B119.6
C18A—C19A—H19A118.6C18B—C19B—H19B119.6
C19A—C20A—C21A118.7 (6)C19B—C20B—C21B120.0 (6)
C19A—C20A—H20A120.6C19B—C20B—H20B120.0
C21A—C20A—H20A120.6C21B—C20B—H20B120.0
O24A—C21A—C20A124.9 (7)C22B—C21B—O24B115.7 (5)
O24A—C21A—C22A115.5 (6)C22B—C21B—C20B119.8 (6)
C20A—C21A—C22A119.6 (6)O24B—C21B—C20B124.5 (6)
C23A—C22A—C21A120.4 (6)C21B—C22B—C23B120.2 (6)
C23A—C22A—H22A119.8C21B—C22B—H22B119.9
C21A—C22A—H22A119.8C23B—C22B—H22B119.9
C22A—C23A—C18A121.8 (6)C22B—C23B—C18B121.1 (6)
C22A—C23A—H23A119.1C22B—C23B—H23B119.4
C18A—C23A—H23A119.1C18B—C23B—H23B119.4
C21A—O24A—C25A117.9 (7)C21B—O24B—C25B117.9 (5)
O24A—C25A—H25A109.5O24B—C25B—H25D109.5
O24A—C25A—H25B109.5O24B—C25B—H25E109.5
H25A—C25A—H25B109.5H25D—C25B—H25E109.5
O24A—C25A—H25C109.5O24B—C25B—H25F109.5
H25A—C25A—H25C109.5H25D—C25B—H25F109.5
H25B—C25A—H25C109.5H25E—C25B—H25F109.5
O27A—C26A—C3A108.1 (5)O27B—C26B—C3B107.6 (5)
O27A—C26A—H26A110.1O27B—C26B—H26C110.2
C3A—C26A—H26A110.1C3B—C26B—H26C110.2
O27A—C26A—H26B110.1O27B—C26B—H26D110.2
C3A—C26A—H26B110.1C3B—C26B—H26D110.2
H26A—C26A—H26B108.4H26C—C26B—H26D108.5
C26A—O27A—C28A113.1 (5)C28B—O27B—C26B112.7 (5)
O27A—C28A—C29A114.1 (6)O27B—C28B—C29B113.7 (5)
O27A—C28A—H28A108.7O27B—C28B—H28C108.8
C29A—C28A—H28A108.7C29B—C28B—H28C108.8
O27A—C28A—H28B108.7O27B—C28B—H28D108.8
C29A—C28A—H28B108.7C29B—C28B—H28D108.8
H28A—C28A—H28B107.6H28C—C28B—H28D107.7
C34A—C29A—C30A117.9 (6)C34B—C29B—C30B117.6 (6)
C34A—C29A—C28A122.2 (6)C34B—C29B—C28B123.0 (6)
C30A—C29A—C28A119.9 (6)C30B—C29B—C28B119.4 (6)
C31A—C30A—C29A120.4 (7)C31B—C30B—C29B121.3 (6)
C31A—C30A—H30A119.8C31B—C30B—H30B119.3
C29A—C30A—H30A119.8C29B—C30B—H30B119.3
C30A—C31A—C32A121.6 (7)C30B—C31B—C32B119.6 (6)
C30A—C31A—H31A119.2C30B—C31B—H31B120.2
C32A—C31A—H31A119.2C32B—C31B—H31B120.2
O35A—C32A—C33A125.1 (6)O35B—C32B—C33B124.6 (5)
O35A—C32A—C31A116.0 (6)O35B—C32B—C31B114.7 (5)
C33A—C32A—C31A118.9 (6)C33B—C32B—C31B120.6 (6)
C32A—C33A—C34A119.2 (6)C32B—C33B—C34B119.1 (5)
C32A—C33A—H33A120.4C32B—C33B—H33B120.5
C34A—C33A—H33A120.4C34B—C33B—H33B120.5
C29A—C34A—C33A121.9 (6)C29B—C34B—C33B121.7 (6)
C29A—C34A—H34A119.0C29B—C34B—H34B119.1
C33A—C34A—H34A119.0C33B—C34B—H34B119.1
C32A—O35A—C36A117.0 (5)C32B—O35B—C36B116.9 (5)
O35A—C36A—H36A109.5O35B—C36B—H36D109.5
O35A—C36A—H36B109.5O35B—C36B—H36E109.5
H36A—C36A—H36B109.5H36D—C36B—H36E109.5
O35A—C36A—H36C109.5O35B—C36B—H36F109.5
H36A—C36A—H36C109.5H36D—C36B—H36F109.5
H36B—C36A—H36C109.5H36E—C36B—H36F109.5
C38A—O37A—C1A119.6 (4)C38B—O37B—C1B118.0 (4)
O39A—C38A—O37A123.1 (5)O39B—C38B—O37B124.4 (5)
O39A—C38A—C40A124.8 (5)O39B—C38B—C40B125.0 (5)
O37A—C38A—C40A112.1 (5)O37B—C38B—C40B110.6 (5)
C45A—C40A—C41A119.0 (5)C41B—C40B—C45B120.2 (5)
C45A—C40A—C38A119.9 (5)C41B—C40B—C38B121.7 (5)
C41A—C40A—C38A120.9 (5)C45B—C40B—C38B118.1 (5)
C42A—C41A—C40A120.1 (5)C42B—C41B—C40B119.5 (5)
C42A—C41A—H41A119.9C42B—C41B—H41B120.3
C40A—C41A—H41A119.9C40B—C41B—H41B120.3
C43A—C42A—C41A119.2 (6)C43B—C42B—C41B119.5 (6)
C43A—C42A—H42A120.4C43B—C42B—H42B120.2
C41A—C42A—H42A120.4C41B—C42B—H42B120.2
C42A—C43A—C44A121.6 (6)C44B—C43B—C42B121.7 (6)
C42A—C43A—Br1A118.5 (5)C44B—C43B—Br1B120.0 (5)
C44A—C43A—Br1A119.9 (5)C42B—C43B—Br1B118.2 (5)
C45A—C44A—C43A118.6 (6)C43B—C44B—C45B119.5 (6)
C45A—C44A—H44A120.7C43B—C44B—H44B120.3
C43A—C44A—H44A120.7C45B—C44B—H44B120.3
C44A—C45A—C40A121.4 (6)C44B—C45B—C40B119.6 (6)
C44A—C45A—H45A119.3C44B—C45B—H45B120.2
C40A—C45A—H45A119.3C40B—C45B—H45B120.2
O37A—C1A—C2A—C15A49.1 (6)O37B—C1B—C2B—C15B48.4 (6)
C6A—C1A—C2A—C15A69.9 (6)C6B—C1B—C2B—C15B70.4 (6)
O37A—C1A—C2A—C3A179.9 (4)O37B—C1B—C2B—C3B179.2 (4)
C6A—C1A—C2A—C3A60.9 (6)C6B—C1B—C2B—C3B60.4 (6)
C15A—C2A—C3A—C26A39.6 (7)C15B—C2B—C3B—C4B88.0 (6)
C1A—C2A—C3A—C26A169.2 (5)C1B—C2B—C3B—C4B41.5 (6)
C15A—C2A—C3A—C4A87.9 (6)C15B—C2B—C3B—C26B39.7 (7)
C1A—C2A—C3A—C4A41.7 (7)C1B—C2B—C3B—C26B169.2 (5)
C26A—C3A—C4A—C5A143.3 (6)C26B—C3B—C4B—C5B143.0 (6)
C2A—C3A—C4A—C5A15.0 (9)C2B—C3B—C4B—C5B14.4 (8)
C3A—C4A—C5A—C6A2.4 (10)C3B—C4B—C5B—C6B2.0 (9)
C4A—C5A—C6A—N7A143.2 (6)C4B—C5B—C6B—N7B143.8 (6)
C4A—C5A—C6A—C1A17.9 (8)C4B—C5B—C6B—C1B18.1 (8)
O37A—C1A—C6A—N7A65.0 (6)O37B—C1B—C6B—N7B63.3 (6)
C2A—C1A—C6A—N7A172.3 (5)C2B—C1B—C6B—N7B173.7 (4)
O37A—C1A—C6A—C5A170.8 (4)O37B—C1B—C6B—C5B171.1 (4)
C2A—C1A—C6A—C5A48.1 (6)C2B—C1B—C6B—C5B48.1 (6)
C5A—C6A—N7A—C9A147.0 (5)C5B—C6B—N7B—C9B146.5 (5)
C1A—C6A—N7A—C9A89.4 (6)C1B—C6B—N7B—C9B89.1 (6)
C5A—C6A—N7A—C8A63.9 (6)C5B—C6B—N7B—C8B63.5 (6)
C1A—C6A—N7A—C8A59.7 (6)C1B—C6B—N7B—C8B60.9 (6)
C8A—N7A—C9A—C10A1.6 (8)C8B—N7B—C9B—C10B1.9 (8)
C6A—N7A—C9A—C10A149.9 (5)C6B—N7B—C9B—C10B150.7 (5)
C8A—N7A—C9A—C14A177.3 (5)C8B—N7B—C9B—C14B179.5 (5)
C6A—N7A—C9A—C14A34.4 (7)C6B—N7B—C9B—C14B31.7 (8)
N7A—C9A—C10A—C11A175.9 (5)N7B—C9B—C10B—C11B176.9 (6)
C14A—C9A—C10A—C11A0.0 (8)C14B—C9B—C10B—C11B0.9 (9)
C9A—C10A—C11A—C12A1.3 (9)C9B—C10B—C11B—C12B0.1 (10)
C10A—C11A—C12A—C13A1.2 (10)C10B—C11B—C12B—C13B0.7 (10)
C11A—C12A—C13A—C14A0.2 (10)C11B—C12B—C13B—C14B0.2 (10)
C12A—C13A—C14A—C9A1.6 (9)C12B—C13B—C14B—C9B0.8 (10)
C10A—C9A—C14A—C13A1.5 (8)N7B—C9B—C14B—C13B176.4 (6)
N7A—C9A—C14A—C13A177.3 (5)C10B—C9B—C14B—C13B1.4 (9)
C1A—C2A—C15A—O16A71.4 (6)C1B—C2B—C15B—O16B71.8 (6)
C3A—C2A—C15A—O16A55.3 (7)C3B—C2B—C15B—O16B54.9 (6)
C2A—C15A—O16A—C17A171.0 (5)C2B—C15B—O16B—C17B171.8 (4)
C15A—O16A—C17A—C18A84.9 (6)C15B—O16B—C17B—C18B84.8 (6)
O16A—C17A—C18A—C23A93.2 (7)O16B—C17B—C18B—C23B94.1 (6)
O16A—C17A—C18A—C19A85.9 (7)O16B—C17B—C18B—C19B84.5 (7)
C23A—C18A—C19A—C20A1.6 (9)C23B—C18B—C19B—C20B1.3 (9)
C17A—C18A—C19A—C20A177.4 (6)C17B—C18B—C19B—C20B177.4 (5)
C18A—C19A—C20A—C21A0.7 (10)C18B—C19B—C20B—C21B0.0 (9)
C19A—C20A—C21A—O24A178.7 (6)C19B—C20B—C21B—C22B1.5 (10)
C19A—C20A—C21A—C22A1.1 (10)C19B—C20B—C21B—O24B180.0 (6)
O24A—C21A—C22A—C23A177.8 (6)O24B—C21B—C22B—C23B179.6 (5)
C20A—C21A—C22A—C23A2.1 (11)C20B—C21B—C22B—C23B1.8 (10)
C21A—C22A—C23A—C18A1.1 (11)C21B—C22B—C23B—C18B0.4 (9)
C19A—C18A—C23A—C22A0.7 (9)C19B—C18B—C23B—C22B1.1 (9)
C17A—C18A—C23A—C22A178.4 (6)C17B—C18B—C23B—C22B177.6 (5)
C20A—C21A—O24A—C25A4.9 (11)C22B—C21B—O24B—C25B173.5 (6)
C22A—C21A—O24A—C25A175.3 (7)C20B—C21B—O24B—C25B5.1 (9)
C4A—C3A—C26A—O27A178.1 (5)C4B—C3B—C26B—O27B177.2 (4)
C2A—C3A—C26A—O27A53.9 (7)C2B—C3B—C26B—O27B54.0 (6)
C3A—C26A—O27A—C28A174.6 (5)C3B—C26B—O27B—C28B174.0 (5)
C26A—O27A—C28A—C29A79.5 (7)C26B—O27B—C28B—C29B80.1 (7)
O27A—C28A—C29A—C34A99.7 (7)O27B—C28B—C29B—C34B99.0 (7)
O27A—C28A—C29A—C30A83.0 (7)O27B—C28B—C29B—C30B83.7 (7)
C34A—C29A—C30A—C31A2.4 (9)C34B—C29B—C30B—C31B1.8 (9)
C28A—C29A—C30A—C31A175.1 (6)C28B—C29B—C30B—C31B175.6 (6)
C29A—C30A—C31A—C32A0.5 (10)C29B—C30B—C31B—C32B0.8 (10)
C30A—C31A—C32A—O35A176.2 (6)C30B—C31B—C32B—O35B176.3 (5)
C30A—C31A—C32A—C33A3.0 (10)C30B—C31B—C32B—C33B1.0 (10)
O35A—C32A—C33A—C34A174.7 (5)O35B—C32B—C33B—C34B175.3 (5)
C31A—C32A—C33A—C34A4.4 (9)C31B—C32B—C33B—C34B1.7 (9)
C30A—C29A—C34A—C33A0.8 (9)C30B—C29B—C34B—C33B1.1 (9)
C28A—C29A—C34A—C33A176.5 (5)C28B—C29B—C34B—C33B176.3 (6)
C32A—C33A—C34A—C29A2.6 (9)C32B—C33B—C34B—C29B0.6 (9)
C33A—C32A—O35A—C36A6.7 (9)C33B—C32B—O35B—C36B9.0 (8)
C31A—C32A—O35A—C36A174.1 (6)C31B—C32B—O35B—C36B173.8 (6)
C6A—C1A—O37A—C38A154.5 (5)C2B—C1B—O37B—C38B81.5 (6)
C2A—C1A—O37A—C38A81.2 (6)C6B—C1B—O37B—C38B154.7 (5)
C1A—O37A—C38A—O39A8.3 (8)C1B—O37B—C38B—O39B7.0 (8)
C1A—O37A—C38A—C40A171.7 (4)C1B—O37B—C38B—C40B172.6 (4)
O39A—C38A—C40A—C45A6.1 (9)O39B—C38B—C40B—C41B170.2 (6)
O37A—C38A—C40A—C45A173.9 (5)O37B—C38B—C40B—C41B9.4 (7)
O39A—C38A—C40A—C41A169.4 (6)O39B—C38B—C40B—C45B6.4 (9)
O37A—C38A—C40A—C41A10.7 (7)O37B—C38B—C40B—C45B174.0 (5)
C45A—C40A—C41A—C42A0.2 (8)C45B—C40B—C41B—C42B1.5 (9)
C38A—C40A—C41A—C42A175.3 (5)C38B—C40B—C41B—C42B175.1 (5)
C40A—C41A—C42A—C43A0.4 (9)C40B—C41B—C42B—C43B2.3 (9)
C41A—C42A—C43A—C44A1.4 (9)C41B—C42B—C43B—C44B1.7 (9)
C41A—C42A—C43A—Br1A179.9 (4)C41B—C42B—C43B—Br1B179.1 (5)
C42A—C43A—C44A—C45A1.9 (9)C42B—C43B—C44B—C45B0.3 (10)
Br1A—C43A—C44A—C45A179.5 (5)Br1B—C43B—C44B—C45B179.4 (5)
C43A—C44A—C45A—C40A1.4 (9)C43B—C44B—C45B—C40B0.5 (9)
C41A—C40A—C45A—C44A0.3 (8)C41B—C40B—C45B—C44B0.1 (9)
C38A—C40A—C45A—C44A175.9 (5)C38B—C40B—C45B—C44B176.6 (5)

Experimental details

Crystal data
Chemical formulaC38H40BrNO6
Mr686.62
Crystal system, space groupTriclinic, P1
Temperature (K)150
a, b, c (Å)7.8180 (2), 11.2850 (3), 18.6830 (5)
α, β, γ (°)90.906 (1), 91.9660 (11), 90.0940 (14)
V3)1647.15 (8)
Z2
Radiation typeMo Kα
µ (mm1)1.30
Crystal size (mm)0.26 × 0.12 × 0.06
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
Tmin, Tmax0.729, 0.926
No. of measured, independent and
observed [I > 2σ(I)] reflections
19157, 10534, 8339
Rint0.081
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.150, 1.03
No. of reflections10534
No. of parameters836
No. of restraints3
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.85, 0.41
Absolute structureFlack (1983)
Absolute structure parameter0.010 (9)

Computer programs: COLLECT (Nonius, 1997-2001), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXTL (Sheldrick, 1999), SHELXTL.

Selected geometric parameters (Å, º) top
C1A—C2A1.528 (7)C1B—C2B1.530 (7)
C2A—C3A1.555 (8)C2B—C3B1.544 (7)
C3A—C4A1.512 (8)C3B—C4B1.512 (8)
C4A—C5A1.324 (9)C4B—C5B1.323 (9)
C5A—C6A1.509 (8)C5B—C6B1.507 (8)
C6A—N7A1.464 (7)C6B—N7B1.471 (7)
N7A—C9A1.409 (7)N7B—C9B1.385 (7)
C6A—C1A—C2A114.2 (5)C2B—C1B—C6B113.6 (4)
C1A—C2A—C3A108.1 (4)C1B—C2B—C3B108.2 (4)
C4A—C3A—C2A112.6 (5)C4B—C3B—C2B113.3 (5)
C5A—C4A—C3A124.6 (6)C5B—C4B—C3B124.5 (5)
C4A—C5A—C6A123.3 (6)C4B—C5B—C6B123.3 (5)
C5A—C6A—C1A109.8 (5)C5B—C6B—C1B109.9 (5)
C9A—N7A—C8A117.7 (5)C9B—N7B—C8B118.2 (5)
C9A—N7A—C6A120.0 (5)C9B—N7B—C6B120.8 (5)
C8A—N7A—C6A114.8 (5)C8B—N7B—C6B114.0 (5)
C6A—N7A—C9A—C10A149.9 (5)C6B—N7B—C9B—C10B150.7 (5)
C1A—C2A—C15A—O16A71.4 (6)C1B—C2B—C15B—O16B71.8 (6)
O16A—C17A—C18A—C19A85.9 (7)O16B—C17B—C18B—C19B84.5 (7)
C2A—C3A—C26A—O27A53.9 (7)C2B—C3B—C26B—O27B54.0 (6)
O27A—C28A—C29A—C30A83.0 (7)O27B—C28B—C29B—C30B83.7 (7)
C1A—O37A—C38A—C40A171.7 (4)C1B—O37B—C38B—C40B172.6 (4)
O37A—C38A—C40A—C41A10.7 (7)O37B—C38B—C40B—C41B9.4 (7)
 

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