Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806041067/ob2076sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806041067/ob2076Isup2.hkl |
CCDC reference: 628030
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.009 Å
- Disorder in main residue
- R factor = 0.060
- wR factor = 0.145
- Data-to-parameter ratio = 17.0
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.20 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.17 Ratio PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C17
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.78 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.23 PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc. PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT480_ALERT_4_C Long H...A H-Bond Reported H11 .. O2 .. 2.72 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 33.60 Deg. C152 -C13 -C15 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 18.40 Deg. C152 -C13 -H131 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 31.10 Deg. C151 -C13 -H132 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 22.70 Deg. H13 -C13 -H132 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 40.40 Deg. C13 -C15 -H131 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 37.60 Deg. C13 -C151 -H132 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 28.70 Deg. C13 -C152 -H131 1.555 1.555 1.555
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.780 Tmax scaled 0.776 Tmin scaled 0.756 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 11 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL/PC (Bruker, 2000); program(s) used to refine structure: SHELXTL/PC; molecular graphics: SHELXTL/PC and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL/PC.
C20H30BrNO2 | F(000) = 832 |
Mr = 396.36 | Dx = 1.243 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 14.258 (2) Å | θ = 10.1–13.3° |
b = 12.210 (4) Å | µ = 1.95 mm−1 |
c = 12.911 (3) Å | T = 293 K |
β = 109.55 (2)° | Block, colourless |
V = 2118.0 (9) Å3 | 0.18 × 0.16 × 0.13 mm |
Z = 4 |
MACH3-Nonius diffractometer | 1762 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.066 |
Graphite monochromator | θmax = 25.0°, θmin = 2.3° |
ω–2θ scans | h = −16→15 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→14 |
Tmin = 0.968, Tmax = 0.994 | l = 0→15 |
3893 measured reflections | 3 standard reflections every 60 min |
3713 independent reflections | intensity decay: none |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0661P)2 + 0.6621P] where P = (Fo2 + 2Fc2)/3 |
3713 reflections | (Δ/σ)max < 0.001 |
218 parameters | Δρmax = 0.44 e Å−3 |
3 restraints | Δρmin = −0.38 e Å−3 |
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 | Occ. (<1) | |
Br1 | 0.23759 (5) | 0.07900 (5) | 0.27954 (5) | 0.0717 (3) | |
C1 | 0.1577 (4) | 0.1322 (4) | 0.4899 (4) | 0.0452 (13) | |
C2 | 0.1364 (3) | 0.2128 (4) | 0.3939 (4) | 0.0397 (12) | |
C3 | 0.2276 (4) | 0.2156 (4) | 0.3561 (4) | 0.0516 (14) | |
H3 | 0.2184 | 0.2760 | 0.3036 | 0.062* | |
C4 | 0.3255 (4) | 0.2349 (5) | 0.4494 (4) | 0.0594 (15) | |
H4A | 0.3240 | 0.3066 | 0.4811 | 0.071* | |
H4B | 0.3798 | 0.2342 | 0.4200 | 0.071* | |
C5 | 0.3449 (4) | 0.1481 (5) | 0.5396 (4) | 0.0572 (15) | |
H5 | 0.3479 | 0.0775 | 0.5047 | 0.069* | |
C6 | 0.2566 (4) | 0.1425 (5) | 0.5789 (4) | 0.0615 (16) | |
H6A | 0.2653 | 0.0803 | 0.6280 | 0.074* | |
H6B | 0.2560 | 0.2080 | 0.6212 | 0.074* | |
C7 | 0.0408 (4) | 0.1989 (4) | 0.2965 (4) | 0.0424 (12) | |
C8 | −0.0036 (4) | 0.2924 (4) | 0.2399 (4) | 0.0625 (16) | |
H8 | 0.0252 | 0.3604 | 0.2626 | 0.075* | |
C9 | −0.0900 (5) | 0.2857 (5) | 0.1501 (5) | 0.081 (2) | |
H9 | −0.1177 | 0.3495 | 0.1131 | 0.098* | |
C10 | −0.1364 (4) | 0.1868 (5) | 0.1138 (4) | 0.0636 (16) | |
C11 | −0.0903 (4) | 0.0946 (4) | 0.1669 (4) | 0.0573 (14) | |
H11 | −0.1180 | 0.0266 | 0.1421 | 0.069* | |
C12 | −0.0035 (4) | 0.0995 (4) | 0.2564 (4) | 0.0492 (13) | |
H12 | 0.0257 | 0.0349 | 0.2903 | 0.059* | |
C13 | −0.2359 (5) | 0.1844 (6) | 0.0171 (6) | 0.099 (2) | |
H13 | −0.2691 | 0.2519 | 0.0270 | 0.118* | 0.50 |
H131 | −0.2092 | 0.1383 | −0.0287 | 0.118* | 0.20 |
H132 | −0.2680 | 0.2560 | −0.0021 | 0.118* | 0.30 |
C14 | −0.3040 (6) | 0.0946 (8) | 0.0323 (8) | 0.164 (3) | |
H14A | −0.3654 | 0.0955 | −0.0284 | 0.246* | |
H14B | −0.3173 | 0.1068 | 0.0995 | 0.246* | |
H14C | −0.2722 | 0.0247 | 0.0354 | 0.246* | |
C15 | −0.2194 (15) | 0.2024 (14) | −0.0913 (10) | 0.114 (7) | 0.50 |
H15A | −0.1753 | 0.2633 | −0.0850 | 0.171* | 0.50 |
H15B | −0.2820 | 0.2173 | −0.1475 | 0.171* | 0.50 |
H15C | −0.1905 | 0.1378 | −0.1105 | 0.171* | 0.50 |
C151 | −0.255 (3) | 0.2844 (18) | −0.054 (2) | 0.114 (7) | 0.20 |
H15D | −0.1930 | 0.3216 | −0.0438 | 0.171* | 0.20 |
H15E | −0.2993 | 0.3324 | −0.0341 | 0.171* | 0.20 |
H15F | −0.2841 | 0.2634 | −0.1296 | 0.171* | 0.20 |
C152 | −0.221 (3) | 0.132 (3) | −0.0812 (18) | 0.114 (7) | 0.30 |
H15G | −0.1773 | 0.1766 | −0.1060 | 0.171* | 0.30 |
H15H | −0.2842 | 0.1256 | −0.1389 | 0.171* | 0.30 |
H15I | −0.1924 | 0.0608 | −0.0617 | 0.171* | 0.30 |
C16 | 0.0691 (5) | 0.3398 (5) | 0.4931 (5) | 0.0679 (17) | |
H16A | 0.0770 | 0.4129 | 0.5221 | 0.102* | |
H16B | 0.0783 | 0.2883 | 0.5518 | 0.102* | |
H16C | 0.0035 | 0.3315 | 0.4405 | 0.102* | |
C17 | 0.4466 (4) | 0.1623 (5) | 0.6339 (5) | 0.0708 (18) | |
C18 | 0.4562 (5) | 0.2710 (6) | 0.6918 (6) | 0.101 (2) | |
H18A | 0.4488 | 0.3292 | 0.6396 | 0.151* | |
H18B | 0.5205 | 0.2759 | 0.7477 | 0.151* | |
H18C | 0.4054 | 0.2771 | 0.7249 | 0.151* | |
C19 | 0.4581 (6) | 0.0687 (8) | 0.7181 (8) | 0.164 (3) | |
H19A | 0.4512 | −0.0007 | 0.6812 | 0.246* | |
H19B | 0.4076 | 0.0755 | 0.7516 | 0.246* | |
H19C | 0.5226 | 0.0730 | 0.7737 | 0.246* | |
C20 | 0.5327 (5) | 0.1524 (7) | 0.5847 (6) | 0.113 (3) | |
H20A | 0.5285 | 0.0829 | 0.5488 | 0.170* | |
H20B | 0.5957 | 0.1582 | 0.6428 | 0.170* | |
H20C | 0.5269 | 0.2102 | 0.5325 | 0.170* | |
N1 | 0.0873 (3) | 0.0694 (3) | 0.4938 (3) | 0.0504 (11) | |
O1 | 0.1133 (3) | 0.0060 (3) | 0.5895 (3) | 0.0704 (12) | |
H1 | 0.0643 | −0.0276 | 0.5919 | 0.106* | |
O2 | 0.1405 (2) | 0.3202 (3) | 0.4413 (3) | 0.0499 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0707 (4) | 0.0843 (5) | 0.0568 (4) | 0.0116 (4) | 0.0170 (3) | −0.0162 (4) |
C1 | 0.052 (3) | 0.046 (3) | 0.034 (3) | −0.005 (3) | 0.009 (3) | 0.002 (3) |
C2 | 0.046 (3) | 0.030 (3) | 0.038 (3) | −0.005 (2) | 0.009 (2) | −0.002 (2) |
C3 | 0.057 (3) | 0.055 (3) | 0.046 (3) | −0.002 (3) | 0.021 (3) | 0.001 (3) |
C4 | 0.047 (3) | 0.066 (4) | 0.064 (4) | −0.004 (3) | 0.017 (3) | 0.001 (3) |
C5 | 0.044 (3) | 0.060 (4) | 0.055 (3) | −0.005 (3) | 0.000 (3) | −0.004 (3) |
C6 | 0.054 (4) | 0.068 (4) | 0.052 (3) | −0.012 (3) | 0.004 (3) | 0.014 (3) |
C7 | 0.050 (3) | 0.036 (3) | 0.040 (3) | 0.000 (3) | 0.013 (3) | −0.002 (3) |
C8 | 0.078 (4) | 0.035 (3) | 0.052 (3) | −0.003 (3) | −0.008 (3) | 0.002 (3) |
C9 | 0.094 (5) | 0.050 (4) | 0.071 (4) | 0.010 (4) | −0.012 (4) | 0.007 (3) |
C10 | 0.064 (4) | 0.056 (4) | 0.053 (4) | 0.005 (3) | −0.004 (3) | −0.010 (3) |
C11 | 0.061 (4) | 0.045 (3) | 0.057 (3) | −0.010 (3) | 0.007 (3) | −0.005 (3) |
C12 | 0.053 (3) | 0.038 (3) | 0.047 (3) | −0.002 (3) | 0.004 (3) | 0.000 (3) |
C13 | 0.087 (5) | 0.087 (5) | 0.084 (5) | −0.012 (4) | −0.022 (4) | −0.004 (4) |
C14 | 0.095 (4) | 0.168 (6) | 0.160 (6) | −0.015 (5) | −0.051 (4) | 0.041 (5) |
C15 | 0.099 (8) | 0.139 (19) | 0.062 (7) | 0.040 (15) | −0.030 (6) | −0.038 (10) |
C151 | 0.099 (8) | 0.139 (19) | 0.062 (7) | 0.040 (15) | −0.030 (6) | −0.038 (10) |
C152 | 0.099 (8) | 0.139 (19) | 0.062 (7) | 0.040 (15) | −0.030 (6) | −0.038 (10) |
C16 | 0.085 (5) | 0.061 (4) | 0.056 (4) | 0.004 (3) | 0.022 (4) | −0.013 (3) |
C17 | 0.053 (4) | 0.076 (5) | 0.068 (4) | 0.003 (3) | −0.002 (3) | −0.011 (4) |
C18 | 0.063 (4) | 0.123 (6) | 0.093 (5) | −0.006 (4) | −0.004 (4) | −0.048 (5) |
C19 | 0.095 (4) | 0.168 (6) | 0.160 (6) | −0.015 (5) | −0.051 (4) | 0.041 (5) |
C20 | 0.051 (4) | 0.158 (8) | 0.118 (6) | 0.016 (4) | 0.010 (4) | −0.046 (6) |
N1 | 0.057 (3) | 0.047 (3) | 0.042 (2) | −0.005 (2) | 0.010 (2) | 0.013 (2) |
O1 | 0.072 (3) | 0.079 (3) | 0.052 (2) | −0.017 (2) | 0.009 (2) | 0.033 (2) |
O2 | 0.054 (2) | 0.037 (2) | 0.054 (2) | −0.0030 (17) | 0.0129 (19) | −0.0075 (17) |
Br1—C3 | 1.968 (5) | C13—H132 | 0.9800 |
C1—N1 | 1.277 (6) | C14—H14A | 0.9600 |
C1—C6 | 1.497 (7) | C14—H14B | 0.9600 |
C1—C2 | 1.531 (6) | C14—H14C | 0.9600 |
C2—O2 | 1.440 (5) | C15—H131 | 1.0990 |
C2—C7 | 1.524 (7) | C15—H15A | 0.9600 |
C2—C3 | 1.535 (7) | C15—H15B | 0.9600 |
C3—C4 | 1.527 (7) | C15—H15C | 0.9600 |
C3—H3 | 0.9800 | C151—H132 | 0.8298 |
C4—C5 | 1.529 (7) | C151—H15D | 0.9600 |
C4—H4A | 0.9700 | C151—H15E | 0.9600 |
C4—H4B | 0.9700 | C151—H15F | 0.9600 |
C5—C6 | 1.509 (7) | C152—H131 | 0.6462 |
C5—C17 | 1.560 (7) | C152—H15G | 0.9600 |
C5—H5 | 0.9800 | C152—H15H | 0.9600 |
C6—H6A | 0.9700 | C152—H15I | 0.9600 |
C6—H6B | 0.9700 | C16—O2 | 1.412 (6) |
C7—C12 | 1.386 (6) | C16—H16A | 0.9600 |
C7—C8 | 1.389 (7) | C16—H16B | 0.9600 |
C8—C9 | 1.383 (8) | C16—H16C | 0.9600 |
C8—H8 | 0.9300 | C17—C18 | 1.507 (8) |
C9—C10 | 1.381 (8) | C17—C19 | 1.548 (10) |
C9—H9 | 0.9300 | C17—C20 | 1.564 (8) |
C10—C11 | 1.367 (7) | C18—H18A | 0.9600 |
C10—C13 | 1.545 (8) | C18—H18B | 0.9600 |
C11—C12 | 1.382 (7) | C18—H18C | 0.9600 |
C11—H11 | 0.9300 | C19—H19A | 0.9600 |
C12—H12 | 0.9300 | C19—H19B | 0.9600 |
C13—C151 | 1.496 (10) | C19—H19C | 0.9600 |
C13—C152 | 1.497 (10) | C20—H20A | 0.9600 |
C13—C15 | 1.510 (9) | C20—H20B | 0.9600 |
C13—C14 | 1.521 (10) | C20—H20C | 0.9600 |
C13—H13 | 0.9800 | N1—O1 | 1.399 (5) |
C13—H131 | 0.9800 | O1—H1 | 0.8200 |
N1—C1—C6 | 124.8 (4) | C15—C13—H132 | 80.9 |
N1—C1—C2 | 118.2 (4) | C14—C13—H132 | 114.3 |
C6—C1—C2 | 116.6 (4) | C10—C13—H132 | 114.4 |
O2—C2—C7 | 110.5 (4) | H13—C13—H132 | 22.7 |
O2—C2—C1 | 105.8 (4) | H131—C13—H132 | 127.1 |
C7—C2—C1 | 118.4 (4) | C13—C14—H14A | 109.5 |
O2—C2—C3 | 101.4 (4) | C13—C14—H14B | 109.5 |
C7—C2—C3 | 111.1 (4) | H14A—C14—H14B | 109.5 |
C1—C2—C3 | 108.2 (4) | C13—C14—H14C | 109.5 |
C4—C3—C2 | 113.6 (4) | H14A—C14—H14C | 109.5 |
C4—C3—Br1 | 109.1 (4) | H14B—C14—H14C | 109.5 |
C2—C3—Br1 | 110.6 (3) | C13—C15—H131 | 40.4 |
C4—C3—H3 | 107.8 | C13—C15—H15A | 109.5 |
C2—C3—H3 | 107.8 | H131—C15—H15A | 124.5 |
Br1—C3—H3 | 107.8 | C13—C15—H15B | 109.5 |
C3—C4—C5 | 112.3 (4) | H131—C15—H15B | 123.5 |
C3—C4—H4A | 109.2 | H15A—C15—H15B | 109.5 |
C5—C4—H4A | 109.2 | C13—C15—H15C | 109.5 |
C3—C4—H4B | 109.2 | H131—C15—H15C | 69.1 |
C5—C4—H4B | 109.2 | H15A—C15—H15C | 109.5 |
H4A—C4—H4B | 107.9 | H15B—C15—H15C | 109.5 |
C6—C5—C4 | 109.2 (4) | C13—C151—H132 | 37.6 |
C6—C5—C17 | 113.9 (5) | C13—C151—H15D | 109.5 |
C4—C5—C17 | 113.7 (5) | H132—C151—H15D | 122.3 |
C6—C5—H5 | 106.5 | C13—C151—H15E | 109.5 |
C4—C5—H5 | 106.5 | H132—C151—H15E | 71.9 |
C17—C5—H5 | 106.5 | H15D—C151—H15E | 109.5 |
C1—C6—C5 | 115.1 (4) | C13—C151—H15F | 109.5 |
C1—C6—H6A | 108.5 | H132—C151—H15F | 124.7 |
C5—C6—H6A | 108.5 | H15D—C151—H15F | 109.5 |
C1—C6—H6B | 108.5 | H15E—C151—H15F | 109.5 |
C5—C6—H6B | 108.5 | C13—C152—H131 | 28.7 |
H6A—C6—H6B | 107.5 | C13—C152—H15G | 109.5 |
C12—C7—C8 | 116.9 (5) | H131—C152—H15G | 108.2 |
C12—C7—C2 | 125.2 (4) | C13—C152—H15H | 109.5 |
C8—C7—C2 | 117.8 (4) | H131—C152—H15H | 132.4 |
C9—C8—C7 | 120.9 (5) | H15G—C152—H15H | 109.5 |
C9—C8—H8 | 119.5 | C13—C152—H15I | 109.5 |
C7—C8—H8 | 119.5 | H131—C152—H15I | 83.8 |
C10—C9—C8 | 121.8 (5) | H15G—C152—H15I | 109.5 |
C10—C9—H9 | 119.1 | H15H—C152—H15I | 109.5 |
C8—C9—H9 | 119.1 | O2—C16—H16A | 109.5 |
C11—C10—C9 | 117.0 (5) | O2—C16—H16B | 109.5 |
C11—C10—C13 | 123.2 (6) | H16A—C16—H16B | 109.5 |
C9—C10—C13 | 119.8 (6) | O2—C16—H16C | 109.5 |
C10—C11—C12 | 122.0 (5) | H16A—C16—H16C | 109.5 |
C10—C11—H11 | 119.0 | H16B—C16—H16C | 109.5 |
C12—C11—H11 | 119.0 | C18—C17—C19 | 109.3 (6) |
C11—C12—C7 | 121.2 (5) | C18—C17—C5 | 113.0 (5) |
C11—C12—H12 | 119.4 | C19—C17—C5 | 108.6 (5) |
C7—C12—H12 | 119.4 | C18—C17—C20 | 108.4 (6) |
C151—C13—C152 | 82.9 (17) | C19—C17—C20 | 108.4 (6) |
C151—C13—C15 | 50.6 (15) | C5—C17—C20 | 109.0 (5) |
C152—C13—C15 | 33.6 (14) | C17—C18—H18A | 109.5 |
C151—C13—C14 | 132.5 (15) | C17—C18—H18B | 109.5 |
C152—C13—C14 | 94.5 (16) | H18A—C18—H18B | 109.5 |
C15—C13—C14 | 121.9 (10) | C17—C18—H18C | 109.5 |
C151—C13—C10 | 114.1 (14) | H18A—C18—H18C | 109.5 |
C152—C13—C10 | 110.0 (16) | H18B—C18—H18C | 109.5 |
C15—C13—C10 | 111.2 (9) | C17—C19—H19A | 109.5 |
C14—C13—C10 | 111.2 (6) | C17—C19—H19B | 109.5 |
C151—C13—H13 | 53.0 | H19A—C19—H19B | 109.5 |
C152—C13—H13 | 132.9 | C17—C19—H19C | 109.5 |
C15—C13—H13 | 103.4 | H19A—C19—H19C | 109.5 |
C14—C13—H13 | 103.4 | H19B—C19—H19C | 109.5 |
C10—C13—H13 | 103.4 | C17—C20—H20A | 109.5 |
C151—C13—H131 | 97.2 | C17—C20—H20B | 109.5 |
C152—C13—H131 | 18.4 | H20A—C20—H20B | 109.5 |
C15—C13—H131 | 46.6 | C17—C20—H20C | 109.5 |
C14—C13—H131 | 93.3 | H20A—C20—H20C | 109.5 |
C10—C13—H131 | 93.5 | H20B—C20—H20C | 109.5 |
H13—C13—H131 | 149.8 | C1—N1—O1 | 112.8 (4) |
C151—C13—H132 | 31.1 | N1—O1—H1 | 109.5 |
C152—C13—H132 | 110.7 | C16—O2—C2 | 115.0 (4) |
N1—C1—C2—O2 | 112.3 (5) | C7—C8—C9—C10 | 0.8 (10) |
C6—C1—C2—O2 | −61.0 (5) | C8—C9—C10—C11 | −3.4 (10) |
N1—C1—C2—C7 | −12.2 (7) | C8—C9—C10—C13 | 176.7 (6) |
C6—C1—C2—C7 | 174.5 (5) | C9—C10—C11—C12 | 3.0 (9) |
N1—C1—C2—C3 | −139.7 (5) | C13—C10—C11—C12 | −177.1 (6) |
C6—C1—C2—C3 | 47.1 (6) | C10—C11—C12—C7 | 0.0 (9) |
O2—C2—C3—C4 | 59.9 (5) | C8—C7—C12—C11 | −2.7 (8) |
C7—C2—C3—C4 | 177.3 (4) | C2—C7—C12—C11 | −179.6 (5) |
C1—C2—C3—C4 | −51.2 (5) | C11—C10—C13—C151 | −159.1 (18) |
O2—C2—C3—Br1 | −177.1 (3) | C9—C10—C13—C151 | 20.8 (19) |
C7—C2—C3—Br1 | −59.7 (4) | C11—C10—C13—C152 | −68.1 (17) |
C1—C2—C3—Br1 | 71.9 (4) | C9—C10—C13—C152 | 111.9 (16) |
C2—C3—C4—C5 | 57.7 (6) | C11—C10—C13—C15 | −104.0 (10) |
Br1—C3—C4—C5 | −66.1 (5) | C9—C10—C13—C15 | 75.9 (11) |
C3—C4—C5—C6 | −54.2 (6) | C11—C10—C13—C14 | 35.3 (10) |
C3—C4—C5—C17 | 177.5 (5) | C9—C10—C13—C14 | −144.8 (8) |
N1—C1—C6—C5 | 138.2 (5) | C6—C5—C17—C18 | −66.3 (7) |
C2—C1—C6—C5 | −49.1 (7) | C4—C5—C17—C18 | 59.6 (7) |
C4—C5—C6—C1 | 50.0 (6) | C6—C5—C17—C19 | 55.2 (8) |
C17—C5—C6—C1 | 178.3 (5) | C4—C5—C17—C19 | −178.9 (6) |
O2—C2—C7—C12 | −156.6 (5) | C6—C5—C17—C20 | 173.0 (6) |
C1—C2—C7—C12 | −34.5 (7) | C4—C5—C17—C20 | −61.0 (7) |
C3—C2—C7—C12 | 91.6 (6) | C6—C1—N1—O1 | −2.5 (7) |
O2—C2—C7—C8 | 26.5 (6) | C2—C1—N1—O1 | −175.2 (4) |
C1—C2—C7—C8 | 148.6 (5) | C7—C2—O2—C16 | 67.4 (5) |
C3—C2—C7—C8 | −85.3 (6) | C1—C2—O2—C16 | −61.9 (5) |
C12—C7—C8—C9 | 2.3 (8) | C3—C2—O2—C16 | −174.8 (4) |
C2—C7—C8—C9 | 179.4 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.82 | 2.13 | 2.851 (5) | 146 |
C11—H11···O2ii | 0.93 | 2.72 | 3.608 (6) | 161 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x, y−1/2, −z+1/2. |
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