Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805023287/hg6205sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805023287/hg6205Isup2.hkl |
CCDC reference: 282374
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.004 Å
- R factor = 0.047
- wR factor = 0.109
- Data-to-parameter ratio = 9.1
checkCIF/PLATON results
No syntax errors found
Alert level C STRVA01_ALERT_4_C Flack test results are meaningless. From the CIF: _refine_ls_abs_structure_Flack 0.200 From the CIF: _refine_ls_abs_structure_Flack_su 2.100 PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 2.00 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 2.00
Alert level G REFLT03_ALERT_4_G 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. From the CIF: _diffrn_reflns_theta_max 26.00 From the CIF: _reflns_number_total 1613 Count of symmetry unique reflns 1613 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 1999); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO–SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1995); software used to prepare material for publication: SHELX97-2 (Sheldrick, 1997) and local procedures.
C16H22N2O | F(000) = 560 |
Mr = 258.36 | Dx = 1.212 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 7956 reflections |
a = 7.2196 (5) Å | θ = 1.0–27.5° |
b = 12.9481 (9) Å | µ = 0.08 mm−1 |
c = 15.1436 (9) Å | T = 173 K |
V = 1415.63 (16) Å3 | Block, colorless |
Z = 4 | 0.30 × 0.16 × 0.09 mm |
Nonius KappaCCD diffractometer | 1115 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.069 |
Graphite monochromator | θmax = 26.0°, θmin = 2.1° |
Detector resolution: 18 pixels mm-1 | h = −8→8 |
ω scans at fixed χ = 55° | k = −13→15 |
7664 measured reflections | l = −18→18 |
1613 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.047 | w = 1/[σ2(Fo2) + (0.0541P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.109 | (Δ/σ)max = 0.006 |
S = 1.02 | Δρmax = 0.22 e Å−3 |
1613 reflections | Δρmin = −0.18 e Å−3 |
177 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.009 (2) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.2 (21) |
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. The model was refined as the R,R,R enantiomer as this was known from the synthesis and starting materials of known chirality. All refinement except the final cycles of least-squares were done using unmerged Friedel pairs (Flack and Bernardinelli, 1999, section 4.4). To conform to Acta E editorial policy the Friedel pairs were merged for the final cycles. The Flack parameter was refined using unmerged data, and is given here merely to indicate that the inversion distinguishing power of the data are very weak, as expected. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.2677 (3) | 0.07790 (17) | −0.06021 (14) | 0.0351 (6) | |
C2 | 0.2678 (4) | 0.1813 (2) | −0.05621 (17) | 0.0347 (8) | |
H2 | 0.2826 | 0.2182 | −0.1100 | 0.042* | |
C3 | 0.2478 (4) | 0.2382 (2) | 0.02070 (16) | 0.0287 (7) | |
C4 | 0.2300 (4) | 0.1827 (2) | 0.09883 (16) | 0.0325 (7) | |
H4 | 0.2180 | 0.2178 | 0.1536 | 0.039* | |
C5 | 0.2299 (4) | 0.0757 (2) | 0.09612 (17) | 0.0335 (7) | |
H5 | 0.2173 | 0.0365 | 0.1488 | 0.040* | |
C6 | 0.2482 (4) | 0.0276 (2) | 0.01596 (18) | 0.0349 (7) | |
H6 | 0.2469 | −0.0457 | 0.0147 | 0.042* | |
C7 | 0.2508 (4) | 0.3544 (2) | 0.01833 (17) | 0.0321 (7) | |
H7A | 0.3760 | 0.3782 | 0.0012 | 0.039* | |
H7B | 0.1622 | 0.3791 | −0.0268 | 0.039* | |
N8 | 0.2020 (3) | 0.39826 (17) | 0.10371 (13) | 0.0313 (6) | |
C9 | 0.1907 (4) | 0.4960 (2) | 0.11154 (16) | 0.0276 (7) | |
C10 | 0.1248 (4) | 0.5379 (2) | 0.20174 (18) | 0.0299 (7) | |
C11 | 0.1416 (4) | 0.6551 (2) | 0.20237 (19) | 0.0299 (7) | |
H11 | 0.1080 | 0.6882 | 0.2598 | 0.036* | |
C12 | 0.0382 (4) | 0.6991 (2) | 0.12162 (18) | 0.0380 (8) | |
H12A | −0.0009 | 0.7720 | 0.1281 | 0.046* | |
H12B | −0.0649 | 0.6552 | 0.1003 | 0.046* | |
C13 | 0.2211 (4) | 0.6845 (2) | 0.07057 (18) | 0.0349 (8) | |
H13 | 0.2491 | 0.7383 | 0.0251 | 0.042* | |
C14 | 0.2306 (4) | 0.5731 (2) | 0.03871 (17) | 0.0328 (8) | |
H14A | 0.1398 | 0.5632 | −0.0096 | 0.039* | |
H14B | 0.3555 | 0.5595 | 0.0144 | 0.039* | |
C15 | 0.3248 (4) | 0.6966 (2) | 0.16003 (18) | 0.0336 (7) | |
C16 | 0.5086 (4) | 0.6406 (2) | 0.1701 (2) | 0.0438 (9) | |
H16A | 0.6003 | 0.6714 | 0.1304 | 0.066* | |
H16B | 0.4924 | 0.5675 | 0.1553 | 0.066* | |
H16C | 0.5516 | 0.6467 | 0.2313 | 0.066* | |
C17 | 0.3554 (5) | 0.8102 (2) | 0.1837 (2) | 0.0490 (9) | |
H17A | 0.4413 | 0.8413 | 0.1413 | 0.074* | |
H17B | 0.4078 | 0.8150 | 0.2433 | 0.074* | |
H17C | 0.2368 | 0.8469 | 0.1818 | 0.074* | |
C18 | 0.2261 (5) | 0.4880 (2) | 0.27828 (16) | 0.0420 (9) | |
H18A | 0.2170 | 0.4127 | 0.2733 | 0.063* | |
H18B | 0.1701 | 0.5105 | 0.3340 | 0.063* | |
H18C | 0.3567 | 0.5086 | 0.2770 | 0.063* | |
O19 | −0.0676 (3) | 0.51187 (17) | 0.21344 (12) | 0.0444 (6) | |
H19 | −0.1064 | 0.4808 | 0.1684 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0373 (16) | 0.0332 (15) | 0.0349 (14) | −0.0042 (13) | 0.0048 (13) | −0.0057 (11) |
C2 | 0.0359 (19) | 0.0397 (19) | 0.0285 (15) | −0.0066 (16) | 0.0051 (15) | 0.0007 (14) |
C3 | 0.0264 (16) | 0.0339 (17) | 0.0256 (15) | −0.0028 (14) | −0.0017 (15) | −0.0037 (13) |
C4 | 0.0349 (18) | 0.0375 (18) | 0.0252 (15) | 0.0032 (15) | 0.0034 (15) | −0.0006 (13) |
C5 | 0.0368 (18) | 0.0327 (18) | 0.0311 (16) | 0.0042 (15) | 0.0032 (16) | 0.0018 (13) |
C6 | 0.0318 (16) | 0.0320 (17) | 0.0408 (17) | −0.0004 (15) | 0.0021 (17) | −0.0013 (14) |
C7 | 0.0371 (17) | 0.0311 (16) | 0.0281 (15) | −0.0021 (15) | 0.0048 (17) | 0.0010 (12) |
N8 | 0.0370 (15) | 0.0314 (14) | 0.0254 (12) | −0.0020 (12) | 0.0005 (12) | −0.0028 (11) |
C9 | 0.0250 (16) | 0.0329 (17) | 0.0250 (14) | −0.0033 (13) | −0.0035 (13) | 0.0009 (14) |
C10 | 0.0299 (16) | 0.0328 (17) | 0.0271 (15) | −0.0038 (14) | −0.0004 (14) | −0.0026 (14) |
C11 | 0.0311 (18) | 0.0299 (17) | 0.0286 (15) | 0.0046 (13) | 0.0014 (14) | −0.0019 (14) |
C12 | 0.0360 (18) | 0.0374 (18) | 0.0407 (16) | 0.0082 (16) | 0.0007 (15) | −0.0005 (15) |
C13 | 0.043 (2) | 0.0288 (17) | 0.0333 (15) | 0.0026 (16) | 0.0035 (15) | 0.0017 (13) |
C14 | 0.0375 (19) | 0.0361 (18) | 0.0249 (14) | −0.0008 (15) | 0.0017 (15) | 0.0000 (12) |
C15 | 0.0348 (17) | 0.0280 (16) | 0.0381 (16) | −0.0046 (14) | 0.0041 (15) | −0.0028 (14) |
C16 | 0.0326 (19) | 0.051 (2) | 0.048 (2) | −0.0042 (15) | 0.0004 (17) | −0.0050 (16) |
C17 | 0.059 (2) | 0.0374 (19) | 0.050 (2) | −0.0104 (17) | 0.0097 (19) | −0.0011 (17) |
C18 | 0.063 (2) | 0.0371 (18) | 0.0255 (15) | −0.0016 (17) | −0.0004 (17) | 0.0026 (14) |
O19 | 0.0386 (14) | 0.0630 (16) | 0.0315 (11) | −0.0182 (10) | 0.0088 (10) | −0.0181 (11) |
N1—C6 | 1.332 (3) | C11—H11 | 1.0000 |
N1—C2 | 1.340 (3) | C12—C13 | 1.542 (4) |
C2—C3 | 1.386 (4) | C12—H12A | 0.9900 |
C2—H2 | 0.9500 | C12—H12B | 0.9900 |
C3—C4 | 1.390 (4) | C13—C14 | 1.522 (4) |
C3—C7 | 1.505 (4) | C13—C15 | 1.556 (4) |
C4—C5 | 1.386 (3) | C13—H13 | 1.0000 |
C4—H4 | 0.9500 | C14—H14A | 0.9900 |
C5—C6 | 1.371 (4) | C14—H14B | 0.9900 |
C5—H5 | 0.9500 | C15—C16 | 1.520 (4) |
C6—H6 | 0.9500 | C15—C17 | 1.530 (4) |
C7—N8 | 1.456 (3) | C16—H16A | 0.9800 |
C7—H7A | 0.9900 | C16—H16B | 0.9800 |
C7—H7B | 0.9900 | C16—H16C | 0.9800 |
N8—C9 | 1.274 (3) | C17—H17A | 0.9800 |
C9—C14 | 1.515 (3) | C17—H17B | 0.9800 |
C9—C10 | 1.544 (4) | C17—H17C | 0.9800 |
C10—O19 | 1.441 (3) | C18—H18A | 0.9800 |
C10—C18 | 1.515 (4) | C18—H18B | 0.9800 |
C10—C11 | 1.523 (3) | C18—H18C | 0.9800 |
C11—C12 | 1.542 (4) | O19—H19 | 0.8400 |
C11—C15 | 1.565 (4) | ||
C6—N1—C2 | 116.7 (2) | C11—C12—H12B | 114.2 |
N1—C2—C3 | 124.7 (3) | C13—C12—H12B | 114.2 |
N1—C2—H2 | 117.7 | H12A—C12—H12B | 111.4 |
C3—C2—H2 | 117.7 | C14—C13—C12 | 108.3 (3) |
C2—C3—C4 | 116.7 (2) | C14—C13—C15 | 110.5 (2) |
C2—C3—C7 | 120.7 (2) | C12—C13—C15 | 87.9 (2) |
C4—C3—C7 | 122.6 (2) | C14—C13—H13 | 115.6 |
C5—C4—C3 | 119.4 (2) | C12—C13—H13 | 115.6 |
C5—C4—H4 | 120.3 | C15—C13—H13 | 115.6 |
C3—C4—H4 | 120.3 | C9—C14—C13 | 112.6 (2) |
C6—C5—C4 | 118.7 (2) | C9—C14—H14A | 109.1 |
C6—C5—H5 | 120.6 | C13—C14—H14A | 109.1 |
C4—C5—H5 | 120.6 | C9—C14—H14B | 109.1 |
N1—C6—C5 | 123.7 (3) | C13—C14—H14B | 109.1 |
N1—C6—H6 | 118.1 | H14A—C14—H14B | 107.8 |
C5—C6—H6 | 118.1 | C16—C15—C17 | 108.0 (2) |
N8—C7—C3 | 111.4 (2) | C16—C15—C13 | 117.4 (2) |
N8—C7—H7A | 109.3 | C17—C15—C13 | 111.7 (2) |
C3—C7—H7A | 109.3 | C16—C15—C11 | 122.2 (2) |
N8—C7—H7B | 109.3 | C17—C15—C11 | 110.8 (2) |
C3—C7—H7B | 109.3 | C13—C15—C11 | 85.2 (2) |
H7A—C7—H7B | 108.0 | C15—C16—H16A | 109.5 |
C9—N8—C7 | 119.1 (2) | C15—C16—H16B | 109.5 |
N8—C9—C14 | 125.0 (2) | H16A—C16—H16B | 109.5 |
N8—C9—C10 | 116.8 (2) | C15—C16—H16C | 109.5 |
C14—C9—C10 | 118.1 (2) | H16A—C16—H16C | 109.5 |
O19—C10—C18 | 105.8 (2) | H16B—C16—H16C | 109.5 |
O19—C10—C11 | 108.0 (2) | C15—C17—H17A | 109.5 |
C18—C10—C11 | 112.4 (2) | C15—C17—H17B | 109.5 |
O19—C10—C9 | 108.9 (2) | H17A—C17—H17B | 109.5 |
C18—C10—C9 | 112.3 (2) | C15—C17—H17C | 109.5 |
C11—C10—C9 | 109.3 (2) | H17A—C17—H17C | 109.5 |
C10—C11—C12 | 108.9 (2) | H17B—C17—H17C | 109.5 |
C10—C11—C15 | 114.0 (2) | C10—C18—H18A | 109.5 |
C12—C11—C15 | 87.6 (2) | C10—C18—H18B | 109.5 |
C10—C11—H11 | 114.5 | H18A—C18—H18B | 109.5 |
C12—C11—H11 | 114.5 | C10—C18—H18C | 109.5 |
C15—C11—H11 | 114.5 | H18A—C18—H18C | 109.5 |
C11—C12—C13 | 86.4 (2) | H18B—C18—H18C | 109.5 |
C11—C12—H12A | 114.2 | C10—O19—H19 | 109.5 |
C13—C12—H12A | 114.2 | ||
C6—N1—C2—C3 | −0.5 (5) | C18—C10—C11—C15 | 83.0 (3) |
N1—C2—C3—C4 | 1.2 (5) | C9—C10—C11—C15 | −42.4 (3) |
N1—C2—C3—C7 | 179.7 (3) | C10—C11—C12—C13 | −87.8 (2) |
C2—C3—C4—C5 | −1.1 (4) | C15—C11—C12—C13 | 26.8 (2) |
C7—C3—C4—C5 | −179.5 (3) | C11—C12—C13—C14 | 83.9 (2) |
C3—C4—C5—C6 | 0.3 (4) | C11—C12—C13—C15 | −27.0 (2) |
C2—N1—C6—C5 | −0.4 (5) | N8—C9—C14—C13 | −175.0 (3) |
C4—C5—C6—N1 | 0.5 (5) | C10—C9—C14—C13 | 7.1 (4) |
C2—C3—C7—N8 | 172.0 (3) | C12—C13—C14—C9 | −49.6 (3) |
C4—C3—C7—N8 | −9.6 (4) | C15—C13—C14—C9 | 45.1 (4) |
C3—C7—N8—C9 | −177.1 (2) | C14—C13—C15—C16 | 41.8 (3) |
C7—N8—C9—C14 | −2.2 (4) | C12—C13—C15—C16 | 150.5 (3) |
C7—N8—C9—C10 | 175.7 (2) | C14—C13—C15—C17 | 167.3 (2) |
N8—C9—C10—O19 | −68.9 (3) | C12—C13—C15—C17 | −83.9 (3) |
C14—C9—C10—O19 | 109.2 (3) | C14—C13—C15—C11 | −82.1 (3) |
N8—C9—C10—C18 | 47.9 (3) | C12—C13—C15—C11 | 26.6 (2) |
C14—C9—C10—C18 | −134.0 (3) | C10—C11—C15—C16 | −36.4 (4) |
N8—C9—C10—C11 | 173.4 (2) | C12—C11—C15—C16 | −146.1 (3) |
C14—C9—C10—C11 | −8.6 (3) | C10—C11—C15—C17 | −165.5 (2) |
O19—C10—C11—C12 | −64.8 (3) | C12—C11—C15—C17 | 84.8 (3) |
C18—C10—C11—C12 | 178.9 (2) | C10—C11—C15—C13 | 83.1 (3) |
C9—C10—C11—C12 | 53.6 (3) | C12—C11—C15—C13 | −26.6 (2) |
O19—C10—C11—C15 | −160.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O19—H19···N1i | 0.84 | 2.02 | 2.855 (3) | 171 |
Symmetry code: (i) x−1/2, −y+1/2, −z. |