Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806036774/ci2154sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806036774/ci2154Isup2.hkl |
CCDC reference: 624166
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- H-atom completeness 99%
- Disorder in solvent or counterion
- R factor = 0.052
- wR factor = 0.147
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O1 .. O3 .. 2.77 Ang.
Alert level C PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 3.17 Sigma PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.74 mm PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms .. ? PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 14.00 Perc. PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........ O1 PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ..... <O3
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C14 H13.14 N1 O2.07 Atom count from the _atom_site data: C14 H13 N1 O2.07 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 8 From the CIF: _chemical_formula_sum C14 H13.14 N O2.07 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 112.00 112.00 0.00 H 105.12 104.00 1.12 N 8.00 8.00 0.00 O 16.56 16.56 0.00
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); 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: WinGX (Farrugia, 1999).
C14H13NO2·0.07H2O | F(000) = 966 |
Mr = 228.52 | Dx = 1.314 Mg m−3 |
Monoclinic, C2/c | Melting point = 384–385 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 23.9334 (14) Å | Cell parameters from 16009 reflections |
b = 7.2265 (5) Å | θ = 2.7–27.3° |
c = 13.9798 (10) Å | µ = 0.09 mm−1 |
β = 107.135 (5)° | T = 296 K |
V = 2310.6 (3) Å3 | Prism, colourless |
Z = 8 | 0.74 × 0.55 × 0.31 mm |
Stoe IPDS-2 diffractometer | 2571 independent reflections |
Radiation source: fine-focus sealed tube | 1917 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.091 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.3°, θmin = 3.0° |
ω scans | h = −30→30 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −9→9 |
Tmin = 0.945, Tmax = 0.975 | l = −17→17 |
17777 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.147 | w = 1/[σ2(Fo2) + (0.12P)2 + 0.2796P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
2571 reflections | Δρmax = 0.17 e Å−3 |
168 parameters | Δρmin = −0.17 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0019 (6) |
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) | |
C1 | 0.49961 (6) | 0.4542 (2) | 0.12132 (9) | 0.0564 (4) | |
C2 | 0.51704 (6) | 0.2776 (2) | 0.09788 (10) | 0.0584 (4) | |
C3 | 0.57502 (7) | 0.2563 (3) | 0.09266 (11) | 0.0700 (5) | |
C4 | 0.61333 (7) | 0.4015 (3) | 0.11587 (12) | 0.0775 (5) | |
H4 | 0.6518 | 0.3841 | 0.1156 | 0.093* | |
C5 | 0.59593 (8) | 0.5740 (3) | 0.13977 (12) | 0.0772 (5) | |
H5 | 0.6226 | 0.6710 | 0.1548 | 0.093* | |
C6 | 0.53988 (7) | 0.6022 (3) | 0.14133 (11) | 0.0673 (4) | |
H6 | 0.5282 | 0.7191 | 0.1556 | 0.081* | |
C7 | 0.44178 (6) | 0.4820 (2) | 0.12575 (9) | 0.0549 (4) | |
H7 | 0.4306 | 0.6001 | 0.1392 | 0.066* | |
C8 | 0.34574 (6) | 0.3702 (2) | 0.11492 (9) | 0.0512 (3) | |
C9 | 0.31695 (7) | 0.5377 (2) | 0.09384 (11) | 0.0618 (4) | |
H9 | 0.3356 | 0.6389 | 0.0756 | 0.074* | |
C10 | 0.26080 (8) | 0.5555 (3) | 0.09968 (13) | 0.0737 (5) | |
H10 | 0.2417 | 0.6689 | 0.0864 | 0.088* | |
C11 | 0.23302 (8) | 0.4056 (3) | 0.12511 (14) | 0.0767 (5) | |
H11 | 0.1951 | 0.4172 | 0.1294 | 0.092* | |
C12 | 0.26123 (8) | 0.2389 (3) | 0.14413 (13) | 0.0723 (5) | |
H12 | 0.2417 | 0.1379 | 0.1605 | 0.087* | |
C13 | 0.31800 (7) | 0.2156 (2) | 0.13976 (10) | 0.0584 (4) | |
C14 | 0.34870 (9) | 0.0330 (2) | 0.16143 (15) | 0.0791 (5) | |
H14A | 0.3234 | −0.0560 | 0.1785 | 0.119* | |
H14B | 0.3837 | 0.0465 | 0.2164 | 0.119* | |
H14C | 0.3587 | −0.0084 | 0.1033 | 0.119* | |
N1 | 0.40398 (5) | 0.34905 (17) | 0.11179 (8) | 0.0538 (3) | |
H1 | 0.4212 (11) | 0.243 (2) | 0.0977 (19) | 0.142 (10)* | |
O1 | 0.48180 (5) | 0.13363 (16) | 0.07991 (9) | 0.0681 (3) | |
O2 | 0.59204 (6) | 0.0894 (3) | 0.06620 (12) | 0.0950 (5) | |
H2 | 0.5634 (14) | 0.016 (5) | 0.032 (2) | 0.148 (12)* | |
O3 | 0.5000 | 0.9181 (18) | 0.2500 | 0.083 (4) | 0.14 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0536 (8) | 0.0719 (9) | 0.0444 (6) | −0.0061 (7) | 0.0154 (5) | 0.0025 (6) |
C2 | 0.0503 (8) | 0.0769 (10) | 0.0491 (7) | −0.0004 (7) | 0.0163 (6) | 0.0051 (6) |
C3 | 0.0528 (9) | 0.0978 (13) | 0.0599 (8) | 0.0073 (8) | 0.0175 (7) | 0.0043 (8) |
C4 | 0.0464 (9) | 0.1247 (17) | 0.0609 (9) | −0.0053 (9) | 0.0151 (7) | 0.0064 (9) |
C5 | 0.0621 (10) | 0.1081 (15) | 0.0602 (8) | −0.0267 (10) | 0.0161 (7) | 0.0011 (9) |
C6 | 0.0653 (10) | 0.0817 (11) | 0.0549 (8) | −0.0150 (8) | 0.0176 (7) | 0.0002 (7) |
C7 | 0.0593 (9) | 0.0581 (8) | 0.0491 (7) | −0.0014 (7) | 0.0189 (6) | −0.0019 (6) |
C8 | 0.0511 (8) | 0.0570 (8) | 0.0472 (6) | −0.0031 (6) | 0.0170 (5) | −0.0060 (5) |
C9 | 0.0615 (9) | 0.0583 (9) | 0.0692 (9) | 0.0003 (7) | 0.0250 (7) | −0.0011 (7) |
C10 | 0.0635 (10) | 0.0788 (11) | 0.0808 (10) | 0.0127 (8) | 0.0243 (8) | −0.0039 (8) |
C11 | 0.0564 (9) | 0.0979 (14) | 0.0812 (11) | −0.0009 (9) | 0.0284 (8) | −0.0056 (9) |
C12 | 0.0638 (10) | 0.0823 (12) | 0.0765 (10) | −0.0182 (9) | 0.0293 (8) | −0.0033 (8) |
C13 | 0.0616 (9) | 0.0619 (9) | 0.0536 (7) | −0.0083 (7) | 0.0201 (6) | −0.0056 (6) |
C14 | 0.0898 (13) | 0.0602 (10) | 0.0929 (12) | −0.0083 (9) | 0.0358 (10) | 0.0041 (8) |
N1 | 0.0544 (7) | 0.0573 (7) | 0.0532 (6) | −0.0003 (6) | 0.0213 (5) | −0.0020 (5) |
O1 | 0.0618 (7) | 0.0667 (7) | 0.0808 (7) | 0.0019 (5) | 0.0289 (5) | −0.0032 (5) |
O2 | 0.0580 (8) | 0.1184 (12) | 0.1093 (10) | 0.0143 (8) | 0.0260 (7) | −0.0173 (9) |
O3 | 0.125 (13) | 0.052 (7) | 0.081 (8) | 0.000 | 0.043 (8) | 0.000 |
C1—C2 | 1.411 (2) | C8—N1 | 1.4157 (19) |
C1—C6 | 1.412 (2) | C9—C10 | 1.376 (2) |
C1—C7 | 1.418 (2) | C9—H9 | 0.93 |
C2—O1 | 1.3160 (19) | C10—C11 | 1.372 (3) |
C2—C3 | 1.419 (2) | C10—H10 | 0.93 |
C3—O2 | 1.359 (2) | C11—C12 | 1.368 (3) |
C3—C4 | 1.368 (3) | C11—H11 | 0.93 |
C4—C5 | 1.386 (3) | C12—C13 | 1.388 (2) |
C4—H4 | 0.93 | C12—H12 | 0.93 |
C5—C6 | 1.363 (3) | C13—C14 | 1.497 (2) |
C5—H5 | 0.93 | C14—H14A | 0.96 |
C6—H6 | 0.93 | C14—H14B | 0.96 |
C7—N1 | 1.2946 (19) | C14—H14C | 0.96 |
C7—H7 | 0.93 | N1—H1 | 0.918 (10) |
C8—C9 | 1.381 (2) | O2—H2 | 0.89 (3) |
C8—C13 | 1.395 (2) | ||
C2—C1—C6 | 120.01 (14) | C10—C9—H9 | 119.9 |
C2—C1—C7 | 119.87 (13) | C8—C9—H9 | 119.9 |
C6—C1—C7 | 120.12 (15) | C11—C10—C9 | 119.87 (17) |
O1—C2—C1 | 122.86 (13) | C11—C10—H10 | 120.1 |
O1—C2—C3 | 119.08 (15) | C9—C10—H10 | 120.1 |
C1—C2—C3 | 118.06 (14) | C12—C11—C10 | 119.78 (16) |
O2—C3—C4 | 120.75 (16) | C12—C11—H11 | 120.1 |
O2—C3—C2 | 119.08 (16) | C10—C11—H11 | 120.1 |
C4—C3—C2 | 120.15 (17) | C11—C12—C13 | 122.11 (16) |
C3—C4—C5 | 121.24 (16) | C11—C12—H12 | 118.9 |
C3—C4—H4 | 119.4 | C13—C12—H12 | 118.9 |
C5—C4—H4 | 119.4 | C12—C13—C8 | 117.23 (15) |
C6—C5—C4 | 120.36 (17) | C12—C13—C14 | 121.77 (15) |
C6—C5—H5 | 119.8 | C8—C13—C14 | 121.00 (14) |
C4—C5—H5 | 119.8 | C13—C14—H14A | 109.5 |
C5—C6—C1 | 120.05 (18) | C13—C14—H14B | 109.5 |
C5—C6—H6 | 120.0 | H14A—C14—H14B | 109.5 |
C1—C6—H6 | 120.0 | C13—C14—H14C | 109.5 |
N1—C7—C1 | 122.39 (14) | H14A—C14—H14C | 109.5 |
N1—C7—H7 | 118.8 | H14B—C14—H14C | 109.5 |
C1—C7—H7 | 118.8 | C7—N1—C8 | 124.48 (13) |
C9—C8—C13 | 120.74 (14) | C7—N1—H1 | 108.2 (18) |
C9—C8—N1 | 121.45 (13) | C8—N1—H1 | 127.3 (18) |
C13—C8—N1 | 117.81 (13) | C3—O2—H2 | 115 (2) |
C10—C9—C8 | 120.24 (16) | ||
C6—C1—C2—O1 | 179.02 (13) | C6—C1—C7—N1 | −177.29 (13) |
C7—C1—C2—O1 | −0.3 (2) | C13—C8—C9—C10 | 1.7 (2) |
C6—C1—C2—C3 | −1.6 (2) | N1—C8—C9—C10 | −178.50 (14) |
C7—C1—C2—C3 | 179.02 (12) | C8—C9—C10—C11 | −1.0 (3) |
O1—C2—C3—O2 | 2.0 (2) | C9—C10—C11—C12 | −0.3 (3) |
C1—C2—C3—O2 | −177.33 (14) | C10—C11—C12—C13 | 0.8 (3) |
O1—C2—C3—C4 | −176.75 (14) | C11—C12—C13—C8 | 0.0 (2) |
C1—C2—C3—C4 | 3.9 (2) | C11—C12—C13—C14 | 179.54 (16) |
O2—C3—C4—C5 | 177.86 (16) | C9—C8—C13—C12 | −1.2 (2) |
C2—C3—C4—C5 | −3.4 (2) | N1—C8—C13—C12 | 179.00 (12) |
C3—C4—C5—C6 | 0.5 (3) | C9—C8—C13—C14 | 179.23 (14) |
C4—C5—C6—C1 | 1.8 (2) | N1—C8—C13—C14 | −0.6 (2) |
C2—C1—C6—C5 | −1.2 (2) | C1—C7—N1—C8 | −179.65 (12) |
C7—C1—C6—C5 | 178.18 (13) | C9—C8—N1—C7 | 26.2 (2) |
C2—C1—C7—N1 | 2.0 (2) | C13—C8—N1—C7 | −154.06 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.89 (3) | 1.95 (3) | 2.787 (2) | 157 (3) |
N1—H1···O1 | 0.92 (1) | 1.73 (2) | 2.5651 (16) | 149 (3) |
Symmetry code: (i) −x+1, −y, −z. |
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