Absolute configurations of Emycin D, E and F; mimicry of centrosymmetric space groups by mixtures of chiral stereoisomers

The crystal structures of Emycin E (1), di-o-bromobenzoyl-Emycin F (2) and o-bromobenzoyl-Emycin D (3) have been determined by X-ray analysis at low temperature. Emycin E and o-bromobenzoyl-Emycin D both crystallize with two molecules in a triclinic unit cell. These two structures can be solved and refined either in the centrosymmetric space group , with apparent disorder localized at or around the expected chiral centre, or in the non-centrosymmetric space group P1 as mixtures of two diastereomers without disorder. Only the latter interpretation is consistent with the chemical and spectroscopic evidence. Refinements in the centrosymmetric and non-centrosymmetric space groups are compared in this paper and are shown to favour the chemically correct interpretation, more decisively so in the case of the bromo derivative as a result of the anomalous dispersion of bromine. Structures (1) and (3) provide a dramatic warning of the dangers inherent in the conventional wisdom that if a structure can be refined satisfactorarily in both centrosymmetric and non-centrosymmetric space groups, the former should always be chosen. In these two cases, despite apparently acceptable intensity statistics and R factors (5.87 and 3.55%), the choice of the centrosymmetric space group leads to the serious chemical error that the triclinic unit cell contains a racemate rather than two chiral diastereomers! The weakest reflections are shown to be most sensitive to the correct choice of space group, underlining the importance of refining against all data rather than against intensities greater than a specified threshold. The use of similar-distance restraints is shown to be beneficial in both P1 refinements. Di-o-bromobenzoyl-Emycin F crystallizes in the monoclinic space group P2₁ with one molecule in the asymmetric unit and so does not give rise to these problems of interpretation. The absolute configuration of the two bromo derivatives, and hence the Emycins in general, was determined unambiguously as S at the chiral centre C3.

Computing details

For all compounds, data collection: DIF4 (Stoe & Cie, 1988a); cell refinement: DIF4 (Stoe & Cie, 1988a); data reduction: REDU4 (Stoe & Cie, 1988b); program(s) used to solve structure: SHELXS90 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL 5.1 (Sheldrick, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

(ende3)

Crystal data

C19H18O4	Z = 2
Mr = 310.33	F(000) = 328
Triclinic, P1	Dx = 1.372 Mg m^−3
a = 8.075 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.871 (2) Å	Cell parameters from 50 reflections
c = 11.606 (2) Å	θ = 10–12.5°
α = 72.69 (3)°	µ = 0.10 mm^−1
β = 80.07 (3)°	T = 153 K
γ = 71.84 (3)°	Blocks, colourless
V = 751.3 (3) Å^3	0.4 × 0.2 × 0.2 mm

Data collection

Stoe-Siemens-Huber AED2 four-circle diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 25.1°, θmin = 3.1°
Graphite monochromator	h = −9→9
profile data from 2θ/ω scans	k = −10→10
5336 measured reflections	l = −13→13
5336 independent reflections	3 standard reflections every 90 min
4018 reflections with I > 2σ(I)

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)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.030P)^2 + 0.8P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
5336 reflections	Δρmax = 0.19 e Å^−3
421 parameters	Δρmin = −0.22 e Å^−3
68 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −3 (2)

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.

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
O1	1.2807 (5)	0.4671 (5)	0.0429 (4)	0.0295 (11)
C1	1.4036 (7)	0.4809 (6)	−0.0336 (5)	0.0201 (14)
C2	1.5307 (8)	0.3314 (7)	−0.0646 (6)	0.0276 (16)
H2A	1.4707	0.2868	−0.1088	0.033*
H2B	1.5636	0.2469	0.0118	0.033*
C3	1.6965 (7)	0.3589 (6)	−0.1404 (5)	0.0241 (14)
H3	1.7667	0.3876	−0.0913	0.029*
C4	1.6411 (8)	0.5043 (6)	−0.2485 (5)	0.0252 (15)
H4A	1.7464	0.5264	−0.3002	0.030*
H4B	1.5708	0.4772	−0.2974	0.030*
C4A	1.5353 (7)	0.6555 (6)	−0.2088 (5)	0.0205 (14)
C5	1.5472 (8)	0.8096 (7)	−0.2795 (5)	0.0249 (15)
H5	1.6196	0.8180	−0.3536	0.030*
C6	1.4557 (8)	0.9505 (7)	−0.2437 (5)	0.0268 (16)
H6	1.4647	1.0547	−0.2934	0.032*
C6A	1.3507 (7)	0.9398 (6)	−0.1355 (5)	0.0224 (14)
O6A	1.2669 (6)	1.0860 (5)	−0.1085 (4)	0.0302 (11)
H6A	1.2355	1.0691	−0.0340	0.045*
O7	1.2253 (5)	0.9084 (5)	0.1095 (4)	0.0230 (10)
C7	1.0646 (7)	0.9451 (7)	0.1866 (5)	0.0234 (15)
H7A	1.0273	1.0623	0.1871	0.028*
H7B	1.0791	0.8763	0.2707	0.028*
C7A	0.9356 (6)	0.9053 (7)	0.1304 (5)	0.0198 (14)
C8	0.7563 (7)	0.9394 (7)	0.1510 (5)	0.0224 (14)
O8	0.6749 (5)	1.0339 (5)	0.2297 (4)	0.0271 (11)
H8	0.5873	1.0035	0.2673	0.041*
C9	0.6665 (7)	0.8842 (7)	0.0879 (5)	0.0233 (14)
H9	0.5424	0.9103	0.0990	0.028*
C10	0.7589 (7)	0.7904 (7)	0.0081 (5)	0.0233 (15)
H10	0.6962	0.7534	−0.0350	0.028*
C11	0.9392 (7)	0.7496 (7)	−0.0099 (5)	0.0207 (14)
H11	1.0014	0.6827	−0.0625	0.025*
C11A	1.0262 (7)	0.8097 (6)	0.0515 (5)	0.0194 (14)
C12	1.2195 (7)	0.7798 (6)	0.0567 (5)	0.0220 (14)
H12	1.2656	0.6702	0.1140	0.026*
C12A	1.3320 (7)	0.7887 (6)	−0.0617 (5)	0.0179 (13)
C12B	1.4251 (7)	0.6461 (6)	−0.1007 (5)	0.0197 (14)
C13	1.8066 (6)	0.2064 (5)	−0.1797 (4)	0.0375 (10)
H13A	1.8426	0.1161	−0.1079	0.056*
H13B	1.9107	0.2294	−0.2306	0.056*
H13C	1.7377	0.1752	−0.2258	0.056*
O1'	0.4082 (5)	0.9157 (5)	0.3601 (4)	0.0307 (12)
C1'	0.2874 (7)	0.9032 (6)	0.4390 (5)	0.0227 (15)
C2'	0.1687 (8)	1.0571 (7)	0.4683 (6)	0.0289 (15)
H2'1	0.1362	1.1401	0.3912	0.035*
H2'2	0.2355	1.1001	0.5089	0.035*
C3'	0.0010 (8)	1.0407 (7)	0.5484 (5)	0.0290 (15)
H3'	−0.0473	1.1394	0.5815	0.035*
C4'	0.0481 (8)	0.8894 (6)	0.6540 (5)	0.0294 (16)
H4'1	0.1197	0.9095	0.7061	0.035*
H4'2	−0.0607	0.8722	0.7032	0.035*
C4A'	0.1476 (7)	0.7354 (6)	0.6153 (5)	0.0232 (14)
C5'	0.1312 (8)	0.5834 (6)	0.6852 (5)	0.0254 (15)
H5'	0.0546	0.5779	0.7573	0.030*
C6'	0.2213 (7)	0.4417 (7)	0.6538 (5)	0.0241 (15)
H6'	0.2095	0.3392	0.7051	0.029*
C6A'	0.3311 (7)	0.4465 (6)	0.5467 (5)	0.0230 (15)
O6A'	0.4175 (6)	0.2993 (5)	0.5210 (4)	0.0312 (11)
H6A'	0.4616	0.3161	0.4488	0.047*
O7'	0.4586 (5)	0.4714 (5)	0.3001 (4)	0.0248 (11)
C7'	0.6191 (7)	0.4354 (8)	0.2212 (5)	0.0235 (15)
H7'1	0.6034	0.5042	0.1371	0.028*
H7'2	0.6577	0.3181	0.2208	0.028*
C7A'	0.7461 (6)	0.4774 (7)	0.2773 (5)	0.0194 (14)
C8'	0.9270 (7)	0.4403 (7)	0.2552 (5)	0.0210 (14)
O8'	1.0052 (5)	0.3514 (5)	0.1721 (4)	0.0297 (11)
H8'	1.1052	0.3645	0.1477	0.045*
C9'	1.0184 (8)	0.4946 (7)	0.3180 (6)	0.0271 (16)
H9'	1.1421	0.4709	0.3041	0.033*
C10'	0.9298 (7)	0.5836 (8)	0.4010 (6)	0.0268 (15)
H10'	0.9936	0.6182	0.4450	0.032*
C11'	0.7483 (7)	0.6224 (7)	0.4203 (5)	0.0230 (14)
H11'	0.6871	0.6843	0.4764	0.028*
C1A'	0.6598 (6)	0.5693 (7)	0.3566 (5)	0.0182 (14)
C12'	0.4650 (6)	0.6015 (6)	0.3522 (5)	0.0184 (13)
H12'	0.4200	0.7106	0.2941	0.022*
C2A'	0.3508 (7)	0.5956 (6)	0.4709 (5)	0.0211 (14)
C2B'	0.2613 (7)	0.7408 (6)	0.5084 (5)	0.0193 (13)
C13'	−0.1375 (5)	1.0327 (5)	0.4774 (4)	0.0336 (10)
H13D	−0.2477	1.0364	0.5289	0.050*
H13E	−0.0980	0.9302	0.4522	0.050*
H13F	−0.1556	1.1264	0.4056	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.023 (2)	0.027 (2)	0.037 (3)	−0.012 (2)	0.007 (2)	−0.007 (2)
C1	0.016 (3)	0.025 (3)	0.019 (3)	−0.006 (3)	−0.004 (3)	−0.003 (3)
C2	0.035 (4)	0.015 (3)	0.027 (3)	−0.004 (3)	0.004 (3)	−0.005 (2)
C3	0.025 (3)	0.024 (3)	0.022 (3)	−0.005 (2)	0.005 (2)	−0.010 (2)
C4	0.029 (4)	0.023 (3)	0.020 (3)	−0.008 (3)	0.001 (3)	−0.001 (2)
C4A	0.017 (3)	0.025 (3)	0.019 (3)	−0.006 (3)	−0.002 (3)	−0.005 (3)
C5	0.027 (4)	0.032 (4)	0.018 (3)	−0.015 (3)	0.005 (3)	−0.006 (3)
C6	0.025 (3)	0.021 (3)	0.032 (4)	−0.008 (3)	−0.001 (3)	−0.003 (3)
C6A	0.018 (3)	0.020 (3)	0.029 (4)	−0.004 (3)	−0.007 (3)	−0.006 (3)
O6A	0.031 (3)	0.023 (2)	0.032 (3)	−0.0052 (19)	−0.003 (2)	−0.003 (2)
O7	0.025 (2)	0.026 (2)	0.025 (2)	−0.010 (2)	−0.003 (2)	−0.0131 (19)
C7	0.023 (4)	0.022 (3)	0.029 (4)	−0.009 (3)	0.003 (3)	−0.011 (3)
C7A	0.022 (3)	0.019 (3)	0.017 (3)	−0.005 (3)	−0.001 (3)	−0.004 (3)
C8	0.019 (3)	0.018 (3)	0.028 (4)	−0.005 (3)	−0.003 (3)	−0.003 (3)
O8	0.020 (2)	0.029 (2)	0.034 (3)	−0.0098 (19)	0.008 (2)	−0.013 (2)
C9	0.016 (3)	0.030 (4)	0.021 (3)	−0.009 (3)	−0.003 (3)	0.001 (3)
C10	0.026 (3)	0.025 (3)	0.022 (3)	−0.013 (3)	−0.006 (3)	−0.001 (3)
C11	0.026 (3)	0.019 (3)	0.019 (3)	−0.009 (3)	−0.002 (3)	−0.007 (3)
C11A	0.023 (4)	0.014 (3)	0.019 (3)	−0.005 (3)	−0.002 (3)	0.001 (3)
C12	0.023 (4)	0.018 (3)	0.023 (4)	−0.005 (3)	−0.001 (3)	−0.005 (3)
C12A	0.017 (3)	0.020 (3)	0.018 (3)	−0.007 (3)	−0.005 (3)	−0.003 (3)
C12B	0.016 (3)	0.023 (3)	0.021 (3)	−0.006 (3)	−0.004 (3)	−0.005 (3)
C13	0.036 (2)	0.028 (2)	0.038 (2)	−0.0018 (19)	0.0075 (19)	−0.0074 (19)
O1'	0.030 (3)	0.025 (2)	0.034 (3)	−0.011 (2)	0.008 (2)	−0.006 (2)
C1'	0.021 (3)	0.028 (4)	0.024 (4)	−0.010 (3)	−0.003 (3)	−0.008 (3)
C2'	0.027 (3)	0.029 (3)	0.031 (4)	−0.011 (3)	0.004 (3)	−0.009 (3)
C3'	0.031 (3)	0.025 (3)	0.029 (3)	−0.006 (2)	0.001 (3)	−0.007 (2)
C4'	0.030 (4)	0.037 (4)	0.024 (4)	−0.009 (3)	0.005 (3)	−0.016 (3)
C4A'	0.024 (3)	0.027 (3)	0.021 (4)	−0.009 (3)	−0.006 (3)	−0.007 (3)
C5'	0.024 (3)	0.027 (3)	0.021 (4)	−0.006 (3)	−0.002 (3)	0.000 (3)
C6'	0.028 (3)	0.027 (3)	0.017 (3)	−0.013 (3)	−0.006 (3)	0.003 (3)
C6A'	0.020 (3)	0.020 (3)	0.026 (4)	−0.004 (3)	−0.003 (3)	−0.002 (3)
O6A'	0.037 (3)	0.018 (2)	0.033 (3)	−0.006 (2)	0.008 (2)	−0.005 (2)
O7'	0.014 (2)	0.031 (3)	0.031 (3)	−0.009 (2)	0.004 (2)	−0.012 (2)
C7'	0.018 (3)	0.034 (4)	0.018 (3)	−0.005 (3)	0.004 (3)	−0.010 (3)
C7A'	0.018 (3)	0.016 (3)	0.023 (3)	−0.007 (3)	−0.002 (3)	0.000 (3)
C8'	0.022 (3)	0.014 (3)	0.022 (3)	−0.003 (3)	0.003 (3)	−0.002 (3)
O8'	0.021 (2)	0.024 (2)	0.045 (3)	−0.008 (2)	0.011 (2)	−0.016 (2)
C9'	0.017 (3)	0.018 (3)	0.044 (4)	−0.006 (3)	−0.002 (3)	−0.001 (3)
C10'	0.023 (3)	0.030 (3)	0.029 (4)	−0.009 (3)	−0.007 (3)	−0.005 (3)
C11'	0.021 (3)	0.022 (3)	0.023 (3)	−0.006 (3)	−0.003 (3)	0.000 (3)
C1A'	0.013 (3)	0.021 (3)	0.019 (3)	−0.005 (3)	0.001 (3)	−0.003 (3)
C12'	0.014 (3)	0.019 (3)	0.023 (4)	−0.004 (3)	−0.003 (3)	−0.008 (3)
C2A'	0.011 (3)	0.027 (3)	0.023 (4)	−0.004 (3)	−0.001 (3)	−0.007 (3)
C2B'	0.015 (3)	0.021 (3)	0.020 (3)	−0.005 (3)	−0.003 (3)	−0.003 (3)
C13'	0.028 (2)	0.034 (2)	0.032 (2)	−0.0066 (18)	0.0002 (18)	−0.0026 (18)

Geometric parameters (Å, º)

O1—C1	1.222 (6)	O1'—C1'	1.226 (6)
C1—C12B	1.489 (6)	C1'—C2B'	1.485 (6)
C1—C2	1.499 (6)	C1'—C2'	1.499 (7)
C2—C3	1.516 (7)	C2'—C3'	1.526 (7)
C3—C13	1.518 (6)	C3'—C4'	1.520 (7)
C3—C4	1.519 (7)	C3'—C13'	1.529 (7)
C4—C4A	1.503 (6)	C4'—C4A'	1.507 (6)
C4A—C5	1.393 (6)	C4A'—C5'	1.385 (7)
C4A—C12B	1.404 (6)	C4A'—C2B'	1.408 (6)
C5—C6	1.381 (7)	C5'—C6'	1.362 (7)
C6—C6A	1.385 (7)	C6'—C6A'	1.395 (6)
C6A—O6A	1.364 (6)	C6A'—O6A'	1.369 (6)
C6A—C12A	1.397 (6)	C6A'—C2A'	1.393 (6)
O7—C7	1.449 (6)	O7'—C7'	1.459 (6)
O7—C12	1.462 (6)	O7'—C12'	1.471 (6)
C7—C7A	1.495 (7)	C7'—C7A'	1.492 (7)
C7A—C8	1.376 (6)	C7A'—C1A'	1.367 (6)
C7A—C11A	1.392 (6)	C7A'—C8'	1.389 (6)
C8—O8	1.369 (6)	C8'—O8'	1.373 (6)
C8—C9	1.386 (6)	C8'—C9'	1.387 (7)
C9—C10	1.393 (7)	C9'—C10'	1.387 (7)
C10—C11	1.380 (7)	C10'—C11'	1.391 (7)
C11—C11A	1.385 (6)	C11'—C1A'	1.370 (7)
C11A—C12	1.509 (6)	C1A'—C12'	1.516 (6)
C12—C12A	1.507 (6)	C12'—C2A'	1.516 (6)
C12A—C12B	1.414 (6)	C2A'—C2B'	1.420 (6)
O1—C1—C12B	120.6 (5)	O1'—C1'—C2B'	121.8 (5)
O1—C1—C2	120.2 (5)	O1'—C1'—C2'	118.1 (5)
C12B—C1—C2	119.1 (4)	C2B'—C1'—C2'	120.1 (5)
C1—C2—C3	115.4 (5)	C1'—C2'—C3'	116.3 (5)
C2—C3—C13	111.6 (4)	C4'—C3'—C2'	108.0 (5)
C2—C3—C4	107.0 (5)	C4'—C3'—C13'	111.9 (5)
C13—C3—C4	111.7 (4)	C2'—C3'—C13'	111.9 (5)
C4A—C4—C3	111.3 (5)	C4A'—C4'—C3'	113.5 (5)
C5—C4A—C12B	118.5 (5)	C5'—C4A'—C2B'	118.0 (5)
C5—C4A—C4	119.8 (5)	C5'—C4A'—C4'	120.6 (5)
C12B—C4A—C4	121.7 (5)	C2B'—C4A'—C4'	121.4 (5)
C6—C5—C4A	121.2 (5)	C6'—C5'—C4A'	122.1 (5)
C5—C6—C6A	120.0 (5)	C5'—C6'—C6A'	120.2 (5)
O6A—C6A—C6	115.2 (5)	O6A'—C6A'—C2A'	122.4 (5)
O6A—C6A—C12A	123.4 (5)	O6A'—C6A'—C6'	117.0 (5)
C6—C6A—C12A	121.4 (5)	C2A'—C6A'—C6'	120.6 (5)
C7—O7—C12	107.4 (4)	C7'—O7'—C12'	107.3 (4)
O7—C7—C7A	103.9 (4)	O7'—C7'—C7A'	102.8 (4)
C8—C7A—C11A	120.3 (5)	C1A'—C7A'—C8'	120.6 (5)
C8—C7A—C7	130.8 (5)	C1A'—C7A'—C7'	110.5 (4)
C11A—C7A—C7	108.8 (4)	C8'—C7A'—C7'	128.8 (5)
O8—C8—C7A	117.5 (5)	O8'—C8'—C9'	123.7 (5)
O8—C8—C9	123.2 (5)	O8'—C8'—C7A'	117.8 (5)
C7A—C8—C9	119.3 (5)	C9'—C8'—C7A'	118.5 (5)
C8—C9—C10	119.7 (5)	C10'—C9'—C8'	120.3 (5)
C11—C10—C9	121.7 (5)	C9'—C10'—C11'	120.5 (6)
C10—C11—C11A	117.7 (5)	C1A'—C11'—C10'	118.5 (5)
C11—C11A—C7A	121.3 (5)	C7A'—C1A'—C11'	121.5 (5)
C11—C11A—C12	130.3 (5)	C7A'—C1A'—C12'	108.0 (4)
C7A—C11A—C12	108.2 (4)	C11'—C1A'—C12'	130.4 (5)
O7—C12—C12A	110.0 (4)	O7'—C12'—C1A'	102.3 (4)
O7—C12—C11A	103.0 (4)	O7'—C12'—C2A'	110.2 (4)
C12A—C12—C11A	116.8 (5)	C1A'—C12'—C2A'	117.5 (5)
C6A—C12A—C12B	117.8 (5)	C6A'—C2A'—C2B'	118.0 (5)
C6A—C12A—C12	120.4 (4)	C6A'—C2A'—C12'	120.7 (4)
C12B—C12A—C12	121.8 (4)	C2B'—C2A'—C12'	121.3 (5)
C4A—C12B—C12A	121.2 (5)	C4A'—C2B'—C2A'	121.0 (5)
C4A—C12B—C1	116.8 (4)	C4A'—C2B'—C1'	117.3 (4)
C12A—C12B—C1	122.0 (4)	C2A'—C2B'—C1'	121.7 (5)

(gelb)

Crystal data

C33H24Br2O6	F(000) = 680
Mr = 676.34	Dx = 1.638 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 7.796 (2) Å	Cell parameters from 54 reflections
b = 7.914 (2) Å	θ = 10–12.5°
c = 22.243 (2) Å	µ = 3.00 mm^−1
β = 92.12 (2)°	T = 153 K
V = 1371.4 (5) Å^3	Blocks, yellow
Z = 2	0.4 × 0.2 × 0.2 mm

Data collection

Stoe-Siemes-Huber AED2 four-circle diffractometer	4144 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
Graphite monochromator	θmax = 25.1°, θmin = 3.1°
profile data from 2theata/ω scans	h = −9→9
Absorption correction: ψ scan SHEXTL 5.1 (Sheldrick, 1998)	k = −9→9
Tmin = 0.203, Tmax = 0.273	l = −26→26
6184 measured reflections	3 standard reflections every 90 min
4870 independent 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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0439P)^2 + 1.0045P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
4870 reflections	Δρmax = 0.37 e Å^−3
371 parameters	Δρmin = −0.61 e Å^−3
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.017 (10)

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.

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
Br1	0.53656 (7)	−0.26337 (10)	0.62293 (3)	0.0618 (2)
Br2	0.84803 (7)	0.38811 (8)	0.53382 (3)	0.05315 (18)
O1	0.8591 (4)	−0.0143 (4)	0.91404 (13)	0.0246 (7)
O7	1.0971 (4)	−0.0192 (4)	0.85444 (13)	0.0254 (7)
O6A	0.5546 (4)	−0.4198 (4)	0.82114 (13)	0.0242 (7)
O1'	0.6948 (4)	−0.3811 (6)	0.73638 (15)	0.0431 (10)
O8	0.9624 (4)	0.1616 (4)	0.69371 (14)	0.0286 (7)
O11'	0.8264 (5)	0.0459 (5)	0.61244 (16)	0.0475 (11)
C1	1.0182 (5)	−0.0994 (7)	0.90366 (19)	0.0223 (9)
C2	1.1465 (5)	−0.0968 (7)	0.95567 (19)	0.0278 (10)
H2A	1.0894	−0.1263	0.9933	0.033*
H2B	1.1963	0.0177	0.9603	0.033*
C3	1.2901 (5)	−0.2260 (6)	0.94372 (19)	0.0266 (11)
H3	1.3428	−0.1932	0.9051	0.032*
C13	1.4310 (6)	−0.2182 (7)	0.9931 (2)	0.0363 (12)
H13A	1.4753	−0.1026	0.9963	0.054*
H13B	1.5245	−0.2950	0.9831	0.054*
H13C	1.3840	−0.2522	1.0315	0.054*
C4	1.2220 (6)	−0.4080 (6)	0.9361 (2)	0.0262 (10)
H4A	1.3079	−0.4753	0.9148	0.031*
H4B	1.2108	−0.4585	0.9765	0.031*
C4A	1.0527 (6)	−0.4224 (6)	0.90237 (19)	0.0232 (10)
C5	0.9705 (6)	−0.5720 (6)	0.88573 (19)	0.0255 (11)
H5	1.0273	−0.6766	0.8929	0.031*
C6	0.8072 (6)	−0.5714 (6)	0.85882 (19)	0.0248 (10)
H6	0.7558	−0.6753	0.8465	0.030*
C6A	0.7185 (5)	−0.4229 (6)	0.84966 (19)	0.0231 (10)
C7	1.0241 (5)	−0.0468 (6)	0.79540 (19)	0.0264 (10)
H7A	1.0149	−0.1702	0.7888	0.032*
H7B	1.1051	−0.0024	0.7660	0.032*
C7A	0.8499 (5)	0.0307 (6)	0.78141 (19)	0.0218 (10)
C8	0.8213 (6)	0.1269 (6)	0.7295 (2)	0.0265 (10)
C9	0.6627 (6)	0.1978 (6)	0.7138 (2)	0.0295 (11)
H9	0.6498	0.2677	0.6792	0.035*
C10	0.5240 (6)	0.1655 (7)	0.7490 (2)	0.0315 (12)
H10	0.4139	0.2101	0.7382	0.038*
C11	0.5475 (6)	0.0670 (6)	0.8004 (2)	0.0270 (11)
H11	0.4525	0.0435	0.8247	0.032*
C11A	0.7071 (6)	0.0031 (6)	0.8165 (2)	0.0229 (10)
C12	0.7286 (5)	−0.0928 (6)	0.87512 (18)	0.0230 (10)
H12	0.6170	−0.0935	0.8959	0.028*
C12A	0.7930 (5)	−0.2728 (6)	0.86923 (17)	0.0198 (9)
C12B	0.9590 (5)	−0.2764 (6)	0.89062 (17)	0.0203 (9)
C1'	0.5601 (6)	−0.3978 (6)	0.7598 (2)	0.0258 (11)
C2'	0.3883 (5)	−0.3991 (6)	0.7300 (2)	0.0228 (10)
C3'	0.3591 (6)	−0.3446 (6)	0.6709 (2)	0.0285 (11)
C4'	0.1966 (6)	−0.3449 (7)	0.6446 (2)	0.0358 (13)
H4'	0.1784	−0.3055	0.6046	0.043*
C5'	0.0612 (6)	−0.4023 (7)	0.6763 (2)	0.0338 (12)
H5'	−0.0511	−0.4012	0.6582	0.041*
C6'	0.0860 (6)	−0.4615 (6)	0.7343 (2)	0.0306 (11)
H6'	−0.0077	−0.5042	0.7558	0.037*
C7'	0.2488 (6)	−0.4580 (6)	0.7605 (2)	0.0266 (11)
H7'	0.2658	−0.4971	0.8007	0.032*
C11'	0.9444 (6)	0.1224 (6)	0.6340 (2)	0.0293 (11)
C12'	1.0921 (6)	0.1860 (6)	0.6006 (2)	0.0273 (11)
C13'	1.0679 (6)	0.3003 (7)	0.5533 (2)	0.0318 (12)
C14'	1.2035 (7)	0.3562 (8)	0.5205 (2)	0.0421 (15)
H14'	1.1854	0.4352	0.4888	0.051*
C15'	1.3655 (7)	0.2954 (8)	0.5346 (2)	0.0443 (15)
H15'	1.4594	0.3320	0.5119	0.053*
C16'	1.3937 (6)	0.1837 (8)	0.5805 (2)	0.0459 (16)
H16'	1.5062	0.1425	0.5894	0.055*
C17'	1.2571 (6)	0.1302 (8)	0.6141 (2)	0.0373 (12)
H17'	1.2774	0.0544	0.6467	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0324 (3)	0.1028 (6)	0.0505 (4)	−0.0027 (3)	0.0055 (2)	0.0425 (4)
Br2	0.0428 (3)	0.0585 (4)	0.0576 (4)	0.0067 (3)	−0.0058 (3)	0.0178 (3)
O1	0.0250 (16)	0.0265 (18)	0.0222 (17)	−0.0002 (14)	−0.0006 (13)	−0.0055 (14)
O7	0.0271 (16)	0.0251 (18)	0.0240 (17)	−0.0048 (14)	0.0003 (13)	0.0059 (14)
O6A	0.0216 (15)	0.0275 (18)	0.0237 (16)	−0.0057 (13)	0.0028 (12)	−0.0023 (14)
O1'	0.0207 (16)	0.078 (3)	0.0302 (19)	−0.0004 (18)	0.0002 (14)	0.008 (2)
O8	0.0311 (16)	0.034 (2)	0.0211 (16)	−0.0055 (15)	0.0035 (13)	0.0022 (14)
O11'	0.045 (2)	0.066 (3)	0.0320 (19)	−0.026 (2)	0.0106 (16)	−0.015 (2)
C1	0.024 (2)	0.024 (2)	0.019 (2)	−0.002 (2)	0.0008 (16)	−0.002 (2)
C2	0.032 (2)	0.028 (2)	0.024 (2)	−0.004 (2)	−0.0002 (18)	−0.002 (2)
C3	0.026 (2)	0.035 (3)	0.019 (2)	−0.007 (2)	−0.0022 (17)	0.002 (2)
C13	0.031 (2)	0.042 (3)	0.036 (3)	−0.003 (2)	−0.004 (2)	0.001 (2)
C4	0.029 (2)	0.023 (3)	0.026 (2)	−0.001 (2)	−0.0006 (19)	−0.002 (2)
C4A	0.026 (2)	0.026 (3)	0.018 (2)	0.001 (2)	0.0042 (17)	0.004 (2)
C5	0.031 (2)	0.024 (3)	0.022 (2)	0.001 (2)	0.0003 (19)	−0.0022 (19)
C6	0.033 (2)	0.017 (3)	0.024 (2)	−0.0059 (19)	0.0010 (18)	0.0006 (18)
C6A	0.019 (2)	0.030 (3)	0.021 (2)	−0.005 (2)	0.0026 (17)	0.001 (2)
C7	0.027 (2)	0.029 (3)	0.024 (2)	−0.005 (2)	0.0064 (18)	−0.001 (2)
C7A	0.025 (2)	0.021 (3)	0.019 (2)	−0.0015 (19)	0.0028 (18)	−0.0059 (19)
C8	0.028 (2)	0.030 (3)	0.022 (2)	−0.002 (2)	0.0022 (18)	−0.001 (2)
C9	0.033 (2)	0.027 (3)	0.028 (3)	−0.001 (2)	−0.003 (2)	0.001 (2)
C10	0.035 (3)	0.034 (3)	0.025 (3)	0.008 (2)	−0.006 (2)	−0.004 (2)
C11	0.027 (2)	0.030 (3)	0.025 (2)	−0.002 (2)	0.0037 (19)	−0.004 (2)
C11A	0.027 (2)	0.018 (2)	0.024 (2)	−0.0010 (19)	0.0012 (18)	−0.0015 (19)
C12	0.021 (2)	0.027 (3)	0.021 (2)	−0.003 (2)	0.0031 (16)	0.003 (2)
C12A	0.0216 (19)	0.022 (2)	0.016 (2)	−0.0015 (19)	0.0035 (15)	0.0030 (19)
C12B	0.025 (2)	0.021 (2)	0.015 (2)	−0.007 (2)	0.0029 (16)	0.0005 (19)
C1'	0.026 (2)	0.026 (3)	0.025 (2)	−0.002 (2)	0.0025 (19)	−0.001 (2)
C2'	0.023 (2)	0.017 (2)	0.029 (2)	0.0020 (18)	0.0025 (18)	−0.003 (2)
C3'	0.028 (2)	0.028 (3)	0.030 (3)	0.000 (2)	0.0039 (19)	0.003 (2)
C4'	0.031 (3)	0.051 (4)	0.025 (3)	0.002 (2)	−0.003 (2)	0.002 (2)
C5'	0.029 (2)	0.040 (3)	0.032 (3)	0.002 (2)	−0.006 (2)	−0.008 (2)
C6'	0.021 (2)	0.038 (3)	0.033 (3)	0.000 (2)	0.0053 (19)	−0.008 (2)
C7'	0.024 (2)	0.032 (3)	0.023 (2)	0.003 (2)	0.0000 (19)	−0.002 (2)
C11'	0.034 (3)	0.030 (3)	0.024 (2)	−0.003 (2)	0.005 (2)	0.004 (2)
C12'	0.028 (2)	0.035 (3)	0.019 (2)	−0.006 (2)	0.0006 (18)	−0.004 (2)
C13'	0.032 (2)	0.041 (3)	0.023 (2)	−0.006 (2)	−0.0019 (19)	0.006 (2)
C14'	0.052 (3)	0.054 (4)	0.020 (2)	−0.015 (3)	0.000 (2)	0.006 (3)
C15'	0.037 (3)	0.073 (4)	0.023 (3)	−0.018 (3)	0.007 (2)	−0.004 (3)
C16'	0.025 (2)	0.074 (5)	0.039 (3)	−0.003 (3)	−0.001 (2)	−0.012 (3)
C17'	0.034 (3)	0.051 (3)	0.027 (3)	−0.002 (3)	−0.004 (2)	0.004 (2)

Geometric parameters (Å, º)

Br1—C3'	1.891 (5)	C7A—C8	1.393 (6)
Br2—C13'	1.885 (5)	C7A—C11A	1.401 (6)
O1—C1	1.437 (5)	C8—C9	1.391 (6)
O1—C12	1.451 (5)	C9—C10	1.382 (7)
O7—C1	1.424 (5)	C10—C11	1.391 (7)
O7—C7	1.428 (5)	C11—C11A	1.378 (6)
O6A—C1'	1.378 (5)	C11A—C12	1.512 (6)
O6A—C6A	1.405 (5)	C12—C12A	1.518 (7)
O1'—C1'	1.196 (5)	C12A—C12B	1.362 (5)
O8—C11'	1.367 (5)	C1'—C2'	1.472 (6)
O8—C8	1.409 (5)	C2'—C7'	1.384 (6)
O11'—C11'	1.187 (6)	C2'—C3'	1.395 (6)
C1—C12B	1.500 (7)	C3'—C4'	1.375 (6)
C1—C2	1.501 (6)	C4'—C5'	1.369 (7)
C2—C3	1.546 (7)	C5'—C6'	1.379 (7)
C3—C13	1.525 (6)	C6'—C7'	1.377 (6)
C3—C4	1.542 (7)	C11'—C12'	1.480 (6)
C4—C4A	1.498 (6)	C12'—C17'	1.382 (7)
C4A—C12B	1.387 (6)	C12'—C13'	1.395 (7)
C4A—C5	1.389 (6)	C13'—C14'	1.379 (7)
C5—C6	1.387 (6)	C14'—C15'	1.377 (8)
C6—C6A	1.375 (6)	C15'—C16'	1.361 (8)
C6A—C12A	1.385 (6)	C16'—C17'	1.390 (7)
C7—C7A	1.512 (6)
C1—O1—C12	107.1 (3)	O1—C12—C11A	110.6 (4)
C1—O7—C7	118.0 (3)	O1—C12—C12A	103.1 (3)
C1'—O6A—C6A	112.9 (3)	C11A—C12—C12A	115.1 (4)
C11'—O8—C8	116.9 (3)	C12B—C12A—C6A	118.3 (4)
O7—C1—O1	108.3 (4)	C12B—C12A—C12	107.6 (4)
O7—C1—C12B	113.9 (3)	C6A—C12A—C12	134.1 (4)
O1—C1—C12B	102.0 (3)	C12A—C12B—C4A	124.7 (4)
O7—C1—C2	107.0 (3)	C12A—C12B—C1	109.3 (4)
O1—C1—C2	115.1 (4)	C4A—C12B—C1	125.8 (4)
C12B—C1—C2	110.7 (4)	O1'—C1'—O6A	120.3 (4)
C1—C2—C3	108.9 (4)	O1'—C1'—C2'	127.2 (4)
C13—C3—C4	110.7 (4)	O6A—C1'—C2'	112.5 (4)
C13—C3—C2	110.9 (4)	C7'—C2'—C3'	117.5 (4)
C4—C3—C2	112.8 (4)	C7'—C2'—C1'	120.1 (4)
C4A—C4—C3	114.8 (4)	C3'—C2'—C1'	122.4 (4)
C12B—C4A—C5	115.2 (4)	C4'—C3'—C2'	121.0 (4)
C12B—C4A—C4	118.6 (4)	C4'—C3'—Br1	116.3 (4)
C5—C4A—C4	126.0 (4)	C2'—C3'—Br1	122.7 (3)
C6—C5—C4A	121.3 (4)	C5'—C4'—C3'	119.8 (5)
C6A—C6—C5	121.0 (4)	C4'—C5'—C6'	120.7 (4)
C6—C6A—C12A	118.9 (4)	C7'—C6'—C5'	119.0 (5)
C6—C6A—O6A	121.7 (4)	C6'—C7'—C2'	121.9 (4)
C12A—C6A—O6A	119.4 (4)	O11'—C11'—O8	123.9 (4)
O7—C7—C7A	116.8 (4)	O11'—C11'—C12'	125.2 (4)
C8—C7A—C11A	116.1 (4)	O8—C11'—C12'	110.9 (4)
C8—C7A—C7	120.5 (4)	C17'—C12'—C13'	118.0 (4)
C11A—C7A—C7	123.3 (4)	C17'—C12'—C11'	121.2 (4)
C9—C8—C7A	122.9 (4)	C13'—C12'—C11'	120.8 (4)
C9—C8—O8	118.9 (4)	C14'—C13'—C12'	121.5 (5)
C7A—C8—O8	118.1 (4)	C14'—C13'—Br2	117.9 (4)
C10—C9—C8	119.3 (5)	C12'—C13'—Br2	120.6 (3)
C9—C10—C11	119.2 (4)	C15'—C14'—C13'	118.8 (5)
C11A—C11—C10	120.7 (4)	C16'—C15'—C14'	121.3 (5)
C11—C11A—C7A	121.8 (4)	C15'—C16'—C17'	119.7 (5)
C11—C11A—C12	118.6 (4)	C12'—C17'—C16'	120.7 (5)
C7A—C11A—C12	119.6 (4)

(salbei)

Crystal data

C26H19BrO5	Z = 2
Mr = 491.32	F(000) = 500
Triclinic, P1	Dx = 1.565 Mg m^−3
a = 8.279 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.539 (3) Å	Cell parameters from 43 reflections
c = 11.962 (3) Å	θ = 10–12.5°
α = 101.32 (2)°	µ = 2.01 mm^−1
β = 110.25 (2)°	T = 153 K
γ = 92.76 (2)°	Blocks, colourless
V = 1042.9 (5) Å^3	0.4 × 0.2 × 0.2 mm

Data collection

Stoe-Siemens AED2 four-circle) diffractometer	5946 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 25.1°, θmin = 3.0°
profile data from 2θ/ω scans	h = −9→9
Absorption correction: ψ scan SHELXTL 5.1 (Sheldrick, 1998)	k = −13→13
Tmin = 0.376, Tmax = 0.426	l = −14→14
6304 measured reflections	3 standard reflections every 90 min
6304 independent 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)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.030P)^2 + 1.3P] where P = (Fo^2 + 2Fc^2)/3
S = 1.30	(Δ/σ)max < 0.001
6304 reflections	Δρmax = 0.41 e Å^−3
579 parameters	Δρmin = −0.41 e Å^−3
96 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.009 (11)

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.

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
Br1	1.08650 (6)	1.05612 (4)	1.14244 (4)	0.0317 (2)
O1	1.2784 (7)	0.5963 (5)	0.3668 (5)	0.0329 (14)
C1	1.1493 (9)	0.5246 (6)	0.3032 (6)	0.0240 (16)
C2	1.1498 (7)	0.4276 (5)	0.1996 (5)	0.0282 (13)
H2A	1.1453	0.3498	0.2223	0.034*
H2B	1.2590	0.4405	0.1847	0.034*
C3	0.9955 (7)	0.4248 (5)	0.0826 (4)	0.0251 (11)
H3	1.0062	0.5023	0.0587	0.030*
C16	0.9931 (12)	0.3249 (7)	−0.0228 (7)	0.0314 (19)
H16A	0.9070	0.3351	−0.0994	0.047*
H16B	0.9627	0.2478	−0.0077	0.047*
H16C	1.1081	0.3276	−0.0291	0.047*
C4	0.8257 (9)	0.4121 (6)	0.1044 (6)	0.0261 (17)
H4A	0.7341	0.4371	0.0383	0.031*
H4B	0.7928	0.3268	0.0983	0.031*
C4A	0.8290 (9)	0.4829 (7)	0.2264 (6)	0.0231 (18)
C5	0.6716 (9)	0.4943 (7)	0.2440 (6)	0.0254 (18)
H5	0.5651	0.4648	0.1778	0.030*
C6	0.6708 (10)	0.5485 (6)	0.3579 (6)	0.0264 (19)
H6	0.5635	0.5546	0.3696	0.032*
C6A	0.8235 (9)	0.5935 (6)	0.4539 (5)	0.0201 (16)
O6A	0.8105 (7)	0.6445 (5)	0.5645 (4)	0.0247 (12)
C7	0.9762 (9)	0.6934 (6)	0.6610 (6)	0.0247 (17)
H7	0.9658	0.7088	0.7433	0.030*
O7	1.0988 (7)	0.6159 (4)	0.6545 (4)	0.0258 (13)
C7A	1.0475 (10)	0.8052 (5)	0.6376 (6)	0.0234 (17)
C8	1.0233 (10)	0.9238 (5)	0.6652 (7)	0.0254 (18)
O8	0.9113 (7)	0.9580 (5)	0.7270 (5)	0.0280 (13)
C9	1.1014 (11)	1.0080 (6)	0.6261 (7)	0.0288 (19)
H9	1.0855	1.0895	0.6455	0.035*
C10	1.2038 (11)	0.9717 (6)	0.5580 (7)	0.0277 (19)
H10	1.2567	1.0292	0.5302	0.033*
C11	1.2302 (11)	0.8538 (6)	0.5299 (7)	0.0287 (19)
H11	1.3006	0.8296	0.4836	0.034*
C12	1.1507 (10)	0.7720 (5)	0.5713 (6)	0.0242 (18)
C13	1.1407 (10)	0.6378 (6)	0.5511 (6)	0.0269 (19)
H13	1.2496	0.6065	0.5470	0.032*
C14	0.9823 (9)	0.5859 (6)	0.4391 (5)	0.0212 (17)
C15	0.9843 (8)	0.5306 (6)	0.3232 (5)	0.0202 (16)
C1'	0.9692 (9)	0.9577 (8)	0.8488 (6)	0.033 (2)
O1'	1.1139 (8)	0.9454 (9)	0.9035 (6)	0.086 (3)
C2'	0.8275 (9)	0.9766 (6)	0.8961 (6)	0.0272 (19)
C3'	0.8583 (8)	1.0134 (6)	1.0215 (5)	0.0237 (18)
C4'	0.7245 (9)	1.0224 (6)	1.0646 (6)	0.0260 (19)
H4'	0.7482	1.0476	1.1498	0.031*
C5'	0.5563 (11)	0.9946 (7)	0.9834 (7)	0.033 (2)
H5'	0.4635	1.0002	1.0130	0.040*
C6'	0.5205 (10)	0.9585 (7)	0.8592 (6)	0.0278 (18)
H6'	0.4038	0.9395	0.8035	0.033*
C7'	0.6549 (10)	0.9503 (7)	0.8169 (7)	0.033 (2)
H7'	0.6296	0.9262	0.7314	0.040*
Br2	1.51559 (5)	0.21961 (4)	0.27707 (4)	0.03030 (19)
O101	1.3171 (8)	0.6661 (5)	1.0570 (5)	0.0364 (15)
C101	1.4451 (9)	0.7321 (6)	1.1265 (6)	0.0234 (16)
C102	1.4442 (7)	0.8068 (5)	1.2456 (5)	0.0278 (13)
H10A	1.3356	0.8441	1.2283	0.033*
H10B	1.4429	0.7534	1.3008	0.033*
C103	1.5955 (7)	0.9032 (5)	1.3113 (4)	0.0265 (12)
H103	1.5847	0.9645	1.2613	0.032*
C116	1.5946 (12)	0.9642 (7)	1.4375 (7)	0.035 (2)
H11A	1.6976	1.0234	1.4804	0.052*
H11B	1.5956	0.9043	1.4855	0.052*
H11C	1.4899	1.0038	1.4270	0.052*
C104	1.7621 (9)	0.8508 (6)	1.3217 (6)	0.0251 (17)
H10C	1.8609	0.9151	1.3616	0.030*
H10D	1.7772	0.7927	1.3743	0.030*
C14A	1.7649 (8)	0.7896 (6)	1.1995 (6)	0.0203 (17)
C105	1.9175 (9)	0.7805 (6)	1.1787 (6)	0.0217 (17)
H105	2.0235	0.8109	1.2452	0.026*
C106	1.9249 (9)	0.7296 (6)	1.0665 (6)	0.0211 (17)
H106	2.0327	0.7247	1.0552	0.025*
C16A	1.7680 (9)	0.6855 (6)	0.9701 (5)	0.0218 (17)
O16A	1.7810 (7)	0.6349 (4)	0.8580 (4)	0.0275 (13)
C107	1.6162 (9)	0.5877 (6)	0.7616 (6)	0.0286 (19)
H107	1.6266	0.5749	0.6793	0.034*
O107	1.4950 (7)	0.6647 (5)	0.7704 (5)	0.0282 (13)
C17A	1.5445 (10)	0.4742 (5)	0.7813 (6)	0.0233 (17)
C108	1.5701 (10)	0.3572 (6)	0.7519 (7)	0.0264 (18)
O108	1.6827 (8)	0.3238 (5)	0.6899 (5)	0.0316 (14)
C109	1.4904 (11)	0.2714 (6)	0.7883 (7)	0.0304 (19)
H109	1.5056	0.1900	0.7665	0.037*
C110	1.3881 (11)	0.3047 (6)	0.8568 (7)	0.033 (2)
H110	1.3341	0.2455	0.8821	0.040*
C111	1.3629 (10)	0.4229 (6)	0.8893 (6)	0.0245 (17)
H111	1.2953	0.4455	0.9381	0.029*
C112	1.4391 (9)	0.5069 (6)	0.8484 (6)	0.0234 (17)
C113	1.4505 (9)	0.6398 (5)	0.8716 (5)	0.0205 (16)
H113	1.3416	0.6712	0.8757	0.025*
C114	1.6100 (8)	0.6906 (6)	0.9855 (5)	0.0210 (17)
C115	1.6096 (8)	0.7387 (6)	1.1025 (5)	0.0197 (16)
C11'	1.6287 (9)	0.3264 (8)	0.5693 (6)	0.032 (2)
O11'	1.4891 (8)	0.3521 (6)	0.5165 (6)	0.0445 (15)
C12'	1.7702 (8)	0.3051 (6)	0.5219 (5)	0.0222 (17)
C13'	1.7410 (9)	0.2635 (6)	0.3976 (5)	0.0244 (19)
C14'	1.8795 (10)	0.2505 (7)	0.3597 (7)	0.030 (2)
H14'	1.8585	0.2222	0.2752	0.035*
C15'	2.0476 (9)	0.2776 (6)	0.4417 (6)	0.0260 (18)
H15'	2.1415	0.2665	0.4139	0.031*
C16'	2.0798 (10)	0.3211 (7)	0.5643 (7)	0.0305 (19)
H16'	2.1956	0.3420	0.6212	0.037*
C17'	1.9412 (8)	0.3340 (7)	0.6036 (6)	0.0238 (17)
H17'	1.9634	0.3633	0.6881	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0304 (5)	0.0352 (4)	0.0218 (4)	−0.0032 (3)	0.0035 (3)	0.0016 (3)
O1	0.016 (3)	0.047 (3)	0.031 (3)	−0.001 (2)	0.008 (3)	−0.001 (2)
C1	0.017 (4)	0.026 (3)	0.028 (3)	0.005 (3)	0.006 (3)	0.009 (2)
C2	0.018 (3)	0.038 (3)	0.029 (3)	0.009 (2)	0.009 (2)	0.007 (2)
C3	0.023 (3)	0.028 (3)	0.024 (2)	0.004 (2)	0.008 (2)	0.009 (2)
C16	0.030 (5)	0.038 (4)	0.028 (4)	0.003 (3)	0.015 (4)	0.004 (3)
C4	0.018 (4)	0.038 (4)	0.019 (3)	0.005 (3)	0.003 (3)	0.006 (3)
C4A	0.021 (5)	0.028 (4)	0.021 (3)	0.006 (3)	0.007 (3)	0.009 (3)
C5	0.012 (5)	0.038 (4)	0.025 (4)	0.002 (3)	0.003 (3)	0.011 (3)
C6	0.025 (6)	0.028 (4)	0.035 (4)	0.012 (4)	0.017 (4)	0.012 (3)
C6A	0.018 (5)	0.021 (3)	0.021 (4)	0.000 (3)	0.008 (3)	0.003 (3)
O6A	0.013 (3)	0.036 (3)	0.023 (3)	0.001 (2)	0.006 (2)	0.004 (2)
C7	0.018 (5)	0.035 (4)	0.018 (4)	0.005 (3)	0.003 (3)	0.005 (3)
O7	0.026 (4)	0.033 (3)	0.018 (3)	0.002 (2)	0.008 (2)	0.007 (2)
C7A	0.016 (5)	0.035 (4)	0.014 (4)	−0.001 (3)	0.002 (3)	0.003 (3)
C8	0.025 (5)	0.033 (4)	0.018 (4)	0.005 (4)	0.009 (4)	0.001 (3)
O8	0.022 (3)	0.040 (3)	0.021 (3)	0.007 (2)	0.007 (2)	0.006 (2)
C9	0.034 (6)	0.032 (4)	0.019 (4)	0.001 (4)	0.007 (4)	0.007 (3)
C10	0.026 (5)	0.037 (4)	0.024 (4)	−0.001 (4)	0.012 (4)	0.010 (3)
C11	0.028 (6)	0.037 (4)	0.021 (4)	−0.004 (4)	0.014 (4)	−0.001 (3)
C12	0.026 (5)	0.026 (4)	0.016 (4)	0.002 (3)	0.005 (3)	0.001 (3)
C13	0.027 (5)	0.036 (4)	0.019 (4)	0.001 (4)	0.011 (4)	0.005 (3)
C14	0.021 (5)	0.023 (3)	0.019 (4)	0.005 (3)	0.007 (3)	0.005 (3)
C15	0.018 (4)	0.025 (3)	0.017 (3)	0.005 (3)	0.004 (3)	0.009 (3)
C1'	0.026 (6)	0.046 (5)	0.019 (4)	−0.005 (4)	0.005 (4)	−0.004 (3)
O1'	0.021 (4)	0.207 (9)	0.019 (3)	0.028 (4)	0.006 (3)	−0.002 (4)
C2'	0.032 (6)	0.024 (4)	0.023 (4)	0.004 (4)	0.009 (4)	0.001 (3)
C3'	0.020 (5)	0.026 (4)	0.020 (4)	−0.001 (3)	0.003 (4)	0.004 (3)
C4'	0.026 (5)	0.028 (4)	0.018 (4)	−0.005 (3)	0.004 (3)	0.001 (3)
C5'	0.038 (6)	0.037 (4)	0.037 (5)	0.011 (4)	0.021 (4)	0.019 (4)
C6'	0.017 (5)	0.033 (4)	0.026 (4)	0.001 (3)	0.001 (4)	0.004 (3)
C7'	0.041 (6)	0.037 (4)	0.024 (4)	0.010 (4)	0.012 (4)	0.011 (3)
Br2	0.0276 (5)	0.0321 (4)	0.0228 (4)	0.0027 (3)	0.0013 (3)	0.0019 (3)
O101	0.023 (4)	0.049 (3)	0.033 (3)	−0.001 (3)	0.012 (3)	−0.002 (3)
C101	0.020 (4)	0.028 (3)	0.021 (3)	0.004 (3)	0.007 (3)	0.005 (2)
C102	0.024 (3)	0.040 (3)	0.023 (3)	0.010 (3)	0.011 (2)	0.007 (2)
C103	0.032 (3)	0.029 (3)	0.023 (2)	0.008 (2)	0.012 (2)	0.009 (2)
C116	0.038 (6)	0.040 (4)	0.026 (4)	0.002 (4)	0.016 (4)	0.002 (3)
C104	0.028 (5)	0.026 (3)	0.021 (3)	0.001 (3)	0.008 (3)	0.005 (3)
C14A	0.018 (5)	0.020 (3)	0.023 (4)	0.001 (3)	0.005 (3)	0.007 (3)
C105	0.018 (5)	0.018 (3)	0.025 (4)	0.001 (3)	0.003 (3)	0.003 (3)
C106	0.009 (4)	0.024 (4)	0.026 (4)	−0.004 (3)	0.002 (3)	0.007 (3)
C16A	0.023 (5)	0.025 (3)	0.020 (4)	0.007 (3)	0.009 (3)	0.008 (3)
O16A	0.029 (4)	0.032 (3)	0.024 (3)	−0.001 (3)	0.015 (3)	0.003 (2)
C107	0.026 (5)	0.038 (4)	0.023 (4)	−0.001 (4)	0.012 (4)	0.007 (3)
O107	0.023 (4)	0.038 (3)	0.024 (3)	0.009 (3)	0.006 (3)	0.013 (2)
C17A	0.020 (5)	0.032 (4)	0.016 (4)	−0.001 (3)	0.006 (3)	0.004 (3)
C108	0.019 (5)	0.037 (4)	0.020 (4)	0.001 (3)	0.005 (3)	0.004 (3)
O108	0.034 (4)	0.043 (3)	0.020 (3)	0.013 (3)	0.014 (3)	0.005 (2)
C109	0.027 (6)	0.026 (4)	0.030 (4)	0.001 (4)	0.006 (4)	−0.002 (3)
C110	0.032 (6)	0.035 (4)	0.023 (4)	−0.011 (4)	0.002 (4)	0.005 (3)
C111	0.012 (5)	0.037 (4)	0.018 (4)	−0.005 (3)	0.001 (3)	0.002 (3)
C112	0.007 (4)	0.041 (4)	0.015 (3)	−0.002 (3)	−0.001 (3)	0.001 (3)
C113	0.009 (4)	0.032 (4)	0.021 (4)	0.005 (3)	0.004 (3)	0.008 (3)
C114	0.013 (4)	0.022 (3)	0.027 (4)	0.001 (3)	0.004 (3)	0.009 (3)
C115	0.019 (4)	0.016 (3)	0.025 (4)	0.004 (3)	0.008 (3)	0.004 (3)
C11'	0.026 (5)	0.046 (4)	0.023 (4)	0.013 (4)	0.009 (4)	0.006 (3)
O11'	0.037 (4)	0.068 (3)	0.030 (3)	0.022 (3)	0.011 (3)	0.015 (2)
C12'	0.018 (5)	0.029 (4)	0.021 (4)	0.008 (3)	0.005 (4)	0.009 (3)
C13'	0.030 (6)	0.017 (3)	0.023 (4)	0.004 (3)	0.007 (4)	0.004 (3)
C14'	0.039 (6)	0.029 (4)	0.026 (4)	0.013 (4)	0.019 (4)	0.005 (3)
C15'	0.020 (5)	0.027 (4)	0.029 (4)	0.006 (3)	0.009 (3)	0.000 (3)
C16'	0.026 (6)	0.036 (4)	0.030 (4)	0.007 (4)	0.009 (4)	0.011 (3)
C17'	0.017 (5)	0.032 (4)	0.016 (4)	0.000 (3)	0.001 (3)	0.000 (3)

Geometric parameters (Å, º)

Br1—C3'	1.908 (6)	Br2—C13'	1.892 (6)
O1—C1	1.229 (7)	O101—C101	1.207 (7)
C1—C15	1.468 (8)	C101—C115	1.488 (8)
C1—C2	1.499 (8)	C101—C102	1.516 (7)
C2—C3	1.527 (7)	C102—C103	1.505 (7)
C3—C4	1.521 (7)	C103—C104	1.509 (8)
C3—C16	1.526 (8)	C103—C116	1.538 (7)
C4—C4A	1.516 (8)	C104—C14A	1.501 (7)
C4A—C15	1.396 (8)	C14A—C105	1.374 (8)
C4A—C5	1.398 (8)	C14A—C115	1.405 (7)
C5—C6	1.385 (8)	C105—C106	1.380 (8)
C6—C6A	1.373 (8)	C106—C16A	1.395 (8)
C6A—O6A	1.380 (7)	C16A—C114	1.385 (8)
C6A—C14	1.391 (8)	C16A—O16A	1.396 (7)
O6A—C7	1.451 (7)	O16A—C107	1.442 (7)
C7—O7	1.397 (7)	C107—O107	1.389 (8)
C7—C7A	1.508 (7)	C107—C17A	1.506 (7)
O7—C13	1.458 (7)	O107—C113	1.456 (7)
C7A—C12	1.373 (8)	C17A—C108	1.373 (8)
C7A—C8	1.384 (7)	C17A—C112	1.394 (8)
C8—C9	1.382 (8)	C108—C109	1.382 (8)
C8—O8	1.399 (7)	C108—O108	1.403 (7)
O8—C1'	1.368 (7)	O108—C11'	1.362 (7)
C9—C10	1.391 (8)	C109—C110	1.388 (9)
C10—C11	1.383 (8)	C110—C111	1.389 (8)
C11—C12	1.385 (8)	C111—C112	1.384 (7)
C12—C13	1.513 (7)	C112—C113	1.497 (7)
C13—C14	1.506 (8)	C113—C114	1.520 (7)
C14—C15	1.414 (7)	C114—C115	1.402 (7)
C1'—O1'	1.181 (8)	C11'—O11'	1.193 (7)
C1'—C2'	1.476 (8)	C11'—C12'	1.479 (8)
C2'—C7'	1.393 (8)	C12'—C17'	1.393 (7)
C2'—C3'	1.404 (8)	C12'—C13'	1.400 (8)
C3'—C4'	1.374 (8)	C13'—C14'	1.375 (8)
C4'—C5'	1.372 (8)	C14'—C15'	1.374 (8)
C5'—C6'	1.382 (8)	C15'—C16'	1.379 (8)
C6'—C7'	1.373 (9)	C16'—C17'	1.386 (8)
O1—C1—C15	121.7 (6)	O101—C101—C115	122.0 (6)
O1—C1—C2	122.2 (6)	O101—C101—C102	120.0 (6)
C15—C1—C2	116.1 (5)	C115—C101—C102	117.9 (5)
C1—C2—C3	111.4 (5)	C103—C102—C101	114.8 (5)
C4—C3—C16	110.1 (5)	C102—C103—C104	109.3 (5)
C4—C3—C2	110.7 (4)	C102—C103—C116	110.9 (5)
C16—C3—C2	111.8 (5)	C104—C103—C116	111.6 (5)
C4A—C4—C3	115.3 (5)	C14A—C104—C103	112.5 (5)
C15—C4A—C5	119.4 (6)	C105—C14A—C115	117.8 (6)
C15—C4A—C4	121.9 (6)	C105—C14A—C104	121.8 (6)
C5—C4A—C4	118.6 (6)	C115—C14A—C104	120.4 (6)
C6—C5—C4A	120.0 (7)	C14A—C105—C106	123.4 (6)
C6A—C6—C5	120.7 (7)	C105—C106—C16A	117.4 (6)
C6—C6A—O6A	116.8 (6)	C114—C16A—C106	121.9 (6)
C6—C6A—C14	120.8 (6)	C114—C16A—O16A	122.4 (6)
O6A—C6A—C14	122.5 (6)	C106—C16A—O16A	115.6 (6)
C6A—O6A—C7	113.9 (5)	C16A—O16A—C107	113.9 (5)
O7—C7—O6A	109.3 (5)	O107—C107—O16A	109.1 (6)
O7—C7—C7A	103.3 (5)	O107—C107—C17A	103.6 (5)
O6A—C7—C7A	110.1 (5)	O16A—C107—C17A	110.3 (6)
C7—O7—C13	102.9 (5)	C107—O107—C113	103.5 (5)
C12—C7A—C8	119.4 (5)	C108—C17A—C112	120.2 (6)
C12—C7A—C7	107.3 (5)	C108—C17A—C107	133.2 (6)
C8—C7A—C7	133.3 (6)	C112—C17A—C107	106.5 (5)
C9—C8—C7A	120.4 (6)	C17A—C108—C109	119.9 (6)
C9—C8—O8	119.4 (6)	C17A—C108—O108	120.9 (6)
C7A—C8—O8	120.1 (6)	C109—C108—O108	119.2 (6)
C1'—O8—C8	116.5 (6)	C11'—O108—C108	117.4 (6)
C8—C9—C10	119.0 (6)	C108—C109—C110	119.6 (6)
C11—C10—C9	121.5 (6)	C109—C110—C111	121.4 (6)
C10—C11—C12	117.9 (6)	C112—C111—C110	118.1 (6)
C7A—C12—C11	121.9 (6)	C111—C112—C17A	120.8 (6)
C7A—C12—C13	105.8 (5)	C111—C112—C113	132.8 (6)
C11—C12—C13	132.2 (6)	C17A—C112—C113	106.0 (5)
O7—C13—C14	105.8 (5)	O107—C113—C112	102.3 (5)
O7—C13—C12	102.2 (5)	O107—C113—C114	105.2 (5)
C14—C13—C12	107.3 (6)	C112—C113—C114	107.6 (5)
C6A—C14—C15	118.9 (6)	C16A—C114—C115	118.6 (6)
C6A—C14—C13	115.9 (5)	C16A—C114—C113	115.7 (5)
C15—C14—C13	125.2 (6)	C115—C114—C113	125.7 (6)
C4A—C15—C14	120.1 (6)	C114—C115—C14A	120.6 (6)
C4A—C15—C1	119.5 (5)	C114—C115—C101	120.3 (6)
C14—C15—C1	120.3 (6)	C14A—C115—C101	119.1 (5)
O1'—C1'—O8	122.1 (6)	O11'—C11'—O108	121.9 (6)
O1'—C1'—C2'	127.8 (6)	O11'—C11'—C12'	127.2 (6)
O8—C1'—C2'	110.1 (6)	O108—C11'—C12'	110.7 (6)
C7'—C2'—C3'	117.0 (6)	C17'—C12'—C13'	118.1 (6)
C7'—C2'—C1'	120.4 (6)	C17'—C12'—C11'	118.6 (6)
C3'—C2'—C1'	122.4 (6)	C13'—C12'—C11'	123.2 (6)
C4'—C3'—C2'	121.6 (6)	C14'—C13'—C12'	119.9 (6)
C4'—C3'—Br1	115.8 (5)	C14'—C13'—Br2	117.6 (5)
C2'—C3'—Br1	122.6 (5)	C12'—C13'—Br2	122.5 (5)
C5'—C4'—C3'	119.5 (6)	C15'—C14'—C13'	121.3 (6)
C4'—C5'—C6'	120.7 (7)	C14'—C15'—C16'	119.9 (7)
C7'—C6'—C5'	119.5 (7)	C15'—C16'—C17'	119.2 (7)
C6'—C7'—C2'	121.7 (7)	C16'—C17'—C12'	121.5 (6)