Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806053773/ez2057sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806053773/ez2057Isup2.hkl |
CCDC reference: 628486
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.053
- wR factor = 0.159
- Data-to-parameter ratio = 12.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.60 PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc. PLAT432_ALERT_2_C Short Inter X...Y Contact O2 .. C8 .. 2.99 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 5.60 Deg. C10 -C9 -H9B 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 12.10 Deg. C9 -C10 -H9B 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
C19H18N2O4 | F(000) = 356 |
Mr = 338.35 | Dx = 1.317 Mg m−3 |
Monoclinic, P21/c | Melting point: 401 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 14.325 (3) Å | Cell parameters from 1376 reflections |
b = 5.058 (2) Å | θ = 2.5–23.6° |
c = 12.250 (2) Å | µ = 0.09 mm−1 |
β = 105.968 (2)° | T = 298 K |
V = 853.3 (4) Å3 | Block, yellow |
Z = 2 | 0.56 × 0.50 × 0.41 mm |
Siemens SMART 1000 CCD area-detector diffractometer | 1490 independent reflections |
Radiation source: fine-focus sealed tube | 1011 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
φ and ω scans | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→16 |
Tmin = 0.950, Tmax = 0.963 | k = −6→5 |
4114 measured reflections | l = −12→14 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.159 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0871P)2 + 0.186P] where P = (Fo2 + 2Fc2)/3 |
1490 reflections | (Δ/σ)max < 0.001 |
118 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.29 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) | |
N1 | 0.61853 (17) | 0.8866 (5) | 0.59208 (19) | 0.0816 (8) | |
O1 | 0.90116 (12) | 0.2061 (3) | 0.74854 (12) | 0.0621 (6) | |
O2 | 0.92816 (13) | 0.2010 (4) | 0.94279 (13) | 0.0672 (6) | |
C1 | 0.64363 (19) | 0.8817 (6) | 0.6983 (2) | 0.0700 (8) | |
H1 | 0.6131 | 0.9965 | 0.7369 | 0.084* | |
C2 | 0.71890 (17) | 0.7037 (5) | 0.76508 (19) | 0.0556 (6) | |
C3 | 0.77210 (15) | 0.5400 (4) | 0.71201 (17) | 0.0500 (6) | |
H3 | 0.7614 | 0.5403 | 0.6336 | 0.060* | |
C4 | 0.83968 (14) | 0.3817 (4) | 0.77966 (17) | 0.0440 (6) | |
C5 | 0.85645 (15) | 0.3766 (5) | 0.89600 (17) | 0.0479 (6) | |
C6 | 0.8056 (2) | 0.5290 (6) | 0.9499 (2) | 0.0674 (8) | |
H6 | 0.8165 | 0.5230 | 1.0282 | 0.081* | |
C7 | 0.73595 (19) | 0.6961 (6) | 0.8818 (2) | 0.0688 (8) | |
H7 | 0.7000 | 0.8055 | 0.9159 | 0.083* | |
C8 | 0.95755 (19) | 0.0902 (6) | 0.8514 (2) | 0.0644 (7) | |
H8A | 0.9478 | −0.0997 | 0.8493 | 0.077* | |
H8B | 1.0259 | 0.1249 | 0.8611 | 0.077* | |
C9 | 0.5423 (2) | 1.0743 (7) | 0.5358 (3) | 0.0874 (11) | |
H9A | 0.5230 | 1.1805 | 0.5918 | 0.105* | |
H9B | 0.5674 | 1.1924 | 0.4881 | 0.105* | 0.50 |
C10 | 0.5746 (4) | 1.2285 (12) | 0.4580 (6) | 0.0843 (19) | 0.50 |
H10A | 0.6314 | 1.3256 | 0.4975 | 0.126* | 0.50 |
H10B | 0.5243 | 1.3497 | 0.4208 | 0.126* | 0.50 |
H10C | 0.5901 | 1.1154 | 0.4025 | 0.126* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0829 (16) | 0.1007 (18) | 0.0613 (14) | 0.0529 (14) | 0.0200 (12) | 0.0320 (13) |
O1 | 0.0653 (10) | 0.0739 (12) | 0.0459 (9) | 0.0287 (9) | 0.0133 (8) | 0.0112 (8) |
O2 | 0.0706 (11) | 0.0787 (12) | 0.0446 (9) | 0.0326 (10) | 0.0031 (8) | 0.0124 (8) |
C1 | 0.0680 (17) | 0.0793 (19) | 0.0627 (16) | 0.0315 (15) | 0.0179 (13) | 0.0141 (14) |
C2 | 0.0531 (13) | 0.0628 (15) | 0.0480 (13) | 0.0163 (12) | 0.0087 (10) | 0.0133 (12) |
C3 | 0.0499 (12) | 0.0620 (15) | 0.0353 (11) | 0.0104 (11) | 0.0069 (10) | 0.0124 (10) |
C4 | 0.0417 (11) | 0.0474 (12) | 0.0415 (11) | 0.0044 (10) | 0.0092 (9) | 0.0060 (10) |
C5 | 0.0456 (12) | 0.0532 (14) | 0.0394 (11) | 0.0095 (11) | 0.0028 (9) | 0.0099 (10) |
C6 | 0.0748 (16) | 0.085 (2) | 0.0381 (12) | 0.0257 (15) | 0.0083 (12) | 0.0078 (12) |
C7 | 0.0727 (16) | 0.084 (2) | 0.0497 (14) | 0.0314 (15) | 0.0168 (12) | 0.0034 (13) |
C8 | 0.0622 (15) | 0.0739 (17) | 0.0518 (14) | 0.0224 (14) | 0.0066 (12) | 0.0104 (13) |
C9 | 0.080 (2) | 0.103 (3) | 0.079 (2) | 0.0546 (19) | 0.0205 (15) | 0.0387 (19) |
C10 | 0.058 (3) | 0.071 (4) | 0.114 (5) | 0.011 (3) | 0.006 (3) | 0.041 (4) |
N1—C1 | 1.252 (3) | C6—C7 | 1.396 (3) |
N1—C9 | 1.468 (3) | C6—H6 | 0.9300 |
O1—C4 | 1.377 (3) | C7—H7 | 0.9300 |
O1—C8 | 1.423 (3) | C8—H8A | 0.9700 |
O2—C5 | 1.360 (3) | C8—H8B | 0.9700 |
O2—C8 | 1.416 (3) | C9—C10 | 1.404 (7) |
C1—C2 | 1.469 (3) | C9—C9i | 1.490 (7) |
C1—H1 | 0.9300 | C9—H9A | 0.9700 |
C2—C7 | 1.383 (3) | C9—H9B | 0.9700 |
C2—C3 | 1.401 (3) | C10—H9B | 0.4485 |
C3—C4 | 1.350 (3) | C10—H10A | 0.9600 |
C3—H3 | 0.9300 | C10—H10B | 0.9600 |
C4—C5 | 1.379 (3) | C10—H10C | 0.9600 |
C5—C6 | 1.351 (3) | ||
C1—N1—C9 | 117.7 (2) | O2—C8—H8A | 110.0 |
C4—O1—C8 | 105.74 (16) | O1—C8—H8A | 110.0 |
C5—O2—C8 | 106.24 (16) | O2—C8—H8B | 110.0 |
N1—C1—C2 | 123.2 (3) | O1—C8—H8B | 110.0 |
N1—C1—H1 | 118.4 | H8A—C8—H8B | 108.4 |
C2—C1—H1 | 118.4 | C10—C9—N1 | 109.7 (3) |
C7—C2—C3 | 120.0 (2) | C10—C9—C9i | 104.3 (4) |
C7—C2—C1 | 119.1 (2) | N1—C9—C9i | 109.2 (3) |
C3—C2—C1 | 120.9 (2) | C10—C9—H9A | 112.6 |
C4—C3—C2 | 117.1 (2) | N1—C9—H9A | 110.2 |
C4—C3—H3 | 121.5 | C9i—C9—H9A | 110.6 |
C2—C3—H3 | 121.5 | C10—C9—H9B | 5.6 |
C3—C4—O1 | 128.16 (19) | N1—C9—H9B | 109.3 |
C3—C4—C5 | 122.5 (2) | C9i—C9—H9B | 109.4 |
O1—C4—C5 | 109.35 (18) | H9A—C9—H9B | 108.0 |
C6—C5—O2 | 127.8 (2) | C9—C10—H9B | 12.1 |
C6—C5—C4 | 122.0 (2) | C9—C10—H10A | 109.5 |
O2—C5—C4 | 110.16 (19) | H9B—C10—H10A | 98.5 |
C5—C6—C7 | 116.5 (2) | C9—C10—H10B | 109.5 |
C5—C6—H6 | 121.7 | H9B—C10—H10B | 109.8 |
C7—C6—H6 | 121.7 | H10A—C10—H10B | 109.5 |
C2—C7—C6 | 121.9 (2) | C9—C10—H10C | 109.5 |
C2—C7—H7 | 119.1 | H9B—C10—H10C | 119.4 |
C6—C7—H7 | 119.1 | H10A—C10—H10C | 109.5 |
O2—C8—O1 | 108.50 (18) | H10B—C10—H10C | 109.5 |
C9—N1—C1—C2 | −180.0 (3) | O1—C4—C5—C6 | −179.6 (2) |
N1—C1—C2—C7 | −174.5 (3) | C3—C4—C5—O2 | −179.8 (2) |
N1—C1—C2—C3 | 4.5 (4) | O1—C4—C5—O2 | 0.1 (3) |
C7—C2—C3—C4 | −0.7 (4) | O2—C5—C6—C7 | 179.4 (2) |
C1—C2—C3—C4 | −179.8 (2) | C4—C5—C6—C7 | −1.0 (4) |
C2—C3—C4—O1 | −179.5 (2) | C3—C2—C7—C6 | 0.2 (4) |
C2—C3—C4—C5 | 0.4 (3) | C1—C2—C7—C6 | 179.2 (3) |
C8—O1—C4—C3 | 179.9 (2) | C5—C6—C7—C2 | 0.7 (4) |
C8—O1—C4—C5 | 0.0 (3) | C5—O2—C8—O1 | 0.2 (3) |
C8—O2—C5—C6 | 179.5 (3) | C4—O1—C8—O2 | −0.1 (3) |
C8—O2—C5—C4 | −0.2 (3) | C1—N1—C9—C10 | 127.4 (4) |
C3—C4—C5—C6 | 0.5 (4) | C1—N1—C9—C9i | −118.8 (4) |
Symmetry code: (i) −x+1, −y+2, −z+1. |