Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807013992/dn2148sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807013992/dn2148Isup2.hkl |
CCDC reference: 647182
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.005 Å
- R factor = 0.041
- wR factor = 0.102
- Data-to-parameter ratio = 9.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.58 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.03 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C11 - C12 .. 5.20 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C12 - C13 .. 5.43 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 1215 Count of symmetry unique reflns 1222 Completeness (_total/calc) 99.43% 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 7 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 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED, (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) PLATON (Spek, 2003) WinGX (Farrugia, 1999).
C12H17NO | F(000) = 416 |
Mr = 191.27 | Dx = 1.084 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 2695 reflections |
a = 10.753 (1) Å | θ = 2.7–30.0° |
b = 10.8059 (10) Å | µ = 0.07 mm−1 |
c = 10.0883 (11) Å | T = 299 K |
V = 1172.2 (2) Å3 | Prism, colourless |
Z = 4 | 0.5 × 0.15 × 0.15 mm |
Xcalibur System, Oxford Diffraction, Ltd. diffractometer | 1215 independent reflections |
Graphite monochromator | 765 reflections with I > 2σ(I) |
Detector resolution: 8.4012 pixels mm-1 | Rint = 0.075 |
ω scan | θmax = 26°, θmin = 4.2° |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006) | h = −13→13 |
Tmin = 0.962, Tmax = 0.992 | k = −13→13 |
7344 measured reflections | l = −12→7 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 0.88 | w = 1/[σ2(Fo2) + (0.0648P)2] where P = (Fo2 + 2Fc2)/3 |
1271 reflections | (Δ/σ)max < 0.001 |
131 parameters | Δρmax = 0.11 e Å−3 |
1 restraint | Δρmin = −0.12 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 | ||
C1 | 0.0278 (2) | 0.1979 (3) | 0.0617 (4) | 0.0995 (11) | |
H11 | −0.0478 | 0.1530 | 0.0777 | 0.149* | |
H12 | 0.0096 | 0.2710 | 0.0111 | 0.149* | |
H13 | 0.0645 | 0.2211 | 0.1448 | 0.149* | |
C2 | 0.1555 (3) | 0.0049 (3) | 0.0700 (4) | 0.0930 (9) | |
H21 | 0.0848 | −0.0483 | 0.0817 | 0.139* | |
H22 | 0.1839 | 0.0333 | 0.1549 | 0.139* | |
H23 | 0.2210 | −0.0401 | 0.0269 | 0.139* | |
C3 | 0.0573 (3) | 0.0747 (4) | −0.1428 (3) | 0.1009 (12) | |
H31 | −0.0178 | 0.0305 | −0.1225 | 0.151* | |
H32 | 0.1129 | 0.0216 | −0.1906 | 0.151* | |
H33 | 0.0377 | 0.1458 | −0.1960 | 0.151* | |
C4 | 0.1184 (2) | 0.1162 (3) | −0.0155 (2) | 0.0637 (7) | |
C5 | 0.2357 (2) | 0.1914 (2) | −0.0479 (3) | 0.0545 (6) | |
C8 | 0.4116 (2) | 0.3049 (2) | 0.0536 (3) | 0.0538 (6) | |
C9 | 0.4995 (2) | 0.2904 (2) | −0.0432 (3) | 0.0669 (7) | |
H16A | 0.4856 | 0.2343 | −0.1115 | 0.080* | |
C10 | 0.6090 (3) | 0.3583 (3) | −0.0410 (4) | 0.0860 (10) | |
C11 | 0.6240 (4) | 0.4435 (4) | 0.0598 (5) | 0.1097 (14) | |
H14A | 0.6952 | 0.4924 | 0.0616 | 0.132* | |
C12 | 0.5365 (4) | 0.4576 (3) | 0.1570 (5) | 0.1045 (13) | |
H13A | 0.5494 | 0.5144 | 0.2249 | 0.125* | |
C13 | 0.4302 (3) | 0.3883 (3) | 0.1547 (3) | 0.0750 (9) | |
H12A | 0.3708 | 0.3975 | 0.2210 | 0.090* | |
C14 | 0.7062 (3) | 0.3377 (6) | −0.1442 (5) | 0.1393 (17) | |
H141 | 0.7672 | 0.4024 | −0.1391 | 0.209* | |
H142 | 0.6683 | 0.3382 | −0.2304 | 0.209* | |
H143 | 0.7456 | 0.2592 | −0.1294 | 0.209* | |
N7 | 0.30059 (18) | 0.23368 (18) | 0.0564 (2) | 0.0574 (6) | |
H7 | 0.2717 | 0.2156 | 0.1335 | 0.069* | |
O6 | 0.26821 (17) | 0.21176 (19) | −0.16102 (18) | 0.0791 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0604 (17) | 0.137 (3) | 0.101 (2) | −0.0147 (18) | 0.0071 (19) | −0.018 (3) |
C2 | 0.105 (2) | 0.0873 (18) | 0.086 (2) | −0.0325 (18) | −0.001 (2) | 0.012 (2) |
C3 | 0.099 (2) | 0.140 (3) | 0.0636 (18) | −0.062 (2) | −0.0054 (17) | −0.014 (2) |
C4 | 0.0614 (14) | 0.0847 (17) | 0.0451 (14) | −0.0223 (14) | 0.0006 (14) | −0.0025 (14) |
C5 | 0.0564 (14) | 0.0726 (14) | 0.0343 (12) | −0.0075 (13) | −0.0037 (13) | −0.0027 (15) |
C8 | 0.0539 (13) | 0.0555 (12) | 0.0520 (14) | −0.0048 (11) | −0.0147 (14) | 0.0079 (14) |
C9 | 0.0574 (14) | 0.0784 (16) | 0.0648 (16) | −0.0099 (14) | −0.0070 (15) | 0.0179 (17) |
C10 | 0.0577 (17) | 0.103 (2) | 0.097 (2) | −0.0157 (17) | −0.021 (2) | 0.046 (2) |
C11 | 0.078 (2) | 0.095 (2) | 0.156 (4) | −0.037 (2) | −0.056 (3) | 0.033 (3) |
C12 | 0.105 (3) | 0.085 (2) | 0.123 (3) | −0.011 (2) | −0.052 (3) | −0.014 (2) |
C13 | 0.0698 (18) | 0.0705 (17) | 0.085 (2) | 0.0010 (15) | −0.0323 (17) | −0.0105 (17) |
C14 | 0.0622 (19) | 0.211 (4) | 0.145 (4) | −0.015 (2) | 0.012 (3) | 0.067 (4) |
N7 | 0.0600 (11) | 0.0777 (13) | 0.0347 (11) | −0.0171 (10) | −0.0008 (10) | −0.0040 (11) |
O6 | 0.0694 (12) | 0.1308 (17) | 0.0371 (11) | −0.0288 (12) | 0.0009 (10) | −0.0006 (11) |
C1—C4 | 1.529 (4) | C8—C13 | 1.376 (4) |
C1—H11 | 0.9600 | C8—N7 | 1.421 (3) |
C1—H12 | 0.9600 | C9—C10 | 1.387 (3) |
C1—H13 | 0.9600 | C9—H16A | 0.9300 |
C2—C4 | 1.533 (4) | C10—C11 | 1.382 (6) |
C2—H21 | 0.9600 | C10—C14 | 1.492 (5) |
C2—H22 | 0.9600 | C11—C12 | 1.367 (6) |
C2—H23 | 0.9600 | C11—H14A | 0.9300 |
C3—C4 | 1.510 (4) | C12—C13 | 1.367 (5) |
C3—H31 | 0.9600 | C12—H13A | 0.9300 |
C3—H32 | 0.9600 | C13—H12A | 0.9300 |
C3—H33 | 0.9600 | C14—H141 | 0.9600 |
C4—C5 | 1.535 (3) | C14—H142 | 0.9600 |
C5—O6 | 1.214 (3) | C14—H143 | 0.9600 |
C5—N7 | 1.343 (3) | N7—H7 | 0.8600 |
C8—C9 | 1.368 (4) | ||
C4—C1—H11 | 109.5 | C9—C8—C13 | 120.3 (2) |
C4—C1—H12 | 109.5 | C9—C8—N7 | 122.2 (2) |
H11—C1—H12 | 109.5 | C13—C8—N7 | 117.5 (2) |
C4—C1—H13 | 109.5 | C8—C9—C10 | 120.9 (3) |
H11—C1—H13 | 109.5 | C8—C9—H16A | 119.5 |
H12—C1—H13 | 109.5 | C10—C9—H16A | 119.5 |
C4—C2—H21 | 109.5 | C11—C10—C9 | 117.6 (4) |
C4—C2—H22 | 109.5 | C11—C10—C14 | 122.1 (4) |
H21—C2—H22 | 109.5 | C9—C10—C14 | 120.3 (4) |
C4—C2—H23 | 109.5 | C12—C11—C10 | 121.4 (3) |
H21—C2—H23 | 109.5 | C12—C11—H14A | 119.3 |
H22—C2—H23 | 109.5 | C10—C11—H14A | 119.3 |
C4—C3—H31 | 109.5 | C13—C12—C11 | 120.1 (3) |
C4—C3—H32 | 109.5 | C13—C12—H13A | 119.9 |
H31—C3—H32 | 109.5 | C11—C12—H13A | 119.9 |
C4—C3—H33 | 109.5 | C12—C13—C8 | 119.6 (3) |
H31—C3—H33 | 109.5 | C12—C13—H12A | 120.2 |
H32—C3—H33 | 109.5 | C8—C13—H12A | 120.2 |
C3—C4—C1 | 109.1 (3) | C10—C14—H141 | 109.5 |
C3—C4—C2 | 111.0 (3) | C10—C14—H142 | 109.5 |
C1—C4—C2 | 109.4 (3) | H141—C14—H142 | 109.5 |
C3—C4—C5 | 109.5 (2) | C10—C14—H143 | 109.5 |
C1—C4—C5 | 109.1 (2) | H141—C14—H143 | 109.5 |
C2—C4—C5 | 108.8 (2) | H142—C14—H143 | 109.5 |
O6—C5—N7 | 121.7 (2) | C5—N7—C8 | 127.2 (2) |
O6—C5—C4 | 122.2 (2) | C5—N7—H7 | 116.4 |
N7—C5—C4 | 116.1 (2) | C8—N7—H7 | 116.4 |
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H7···O6i | 0.86 | 2.12 | 2.954 (3) | 164 |
Symmetry code: (i) −x+1/2, y, z+1/2. |
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