Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806020204/dn2041sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806020204/dn2041Isup2.hkl |
CCDC reference: 613661
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.074
- wR factor = 0.143
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level B RINTA01_ALERT_3_B The value of Rint is greater than 0.15 Rint given 0.181 PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.18 PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 35 Perc.
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.64 mm PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C12 - C16 ... 1.53 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C3 ... 1.43 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C4 ... 1.44 Ang.
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 5 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
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: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C17H12N2O3 | F(000) = 1216 |
Mr = 292.29 | Dx = 1.301 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 11205 reflections |
a = 8.3942 (7) Å | θ = 1.8–27.4° |
b = 22.426 (2) Å | µ = 0.09 mm−1 |
c = 15.855 (2) Å | T = 293 K |
V = 2984.6 (5) Å3 | Prism, colourless |
Z = 8 | 0.64 × 0.33 × 0.02 mm |
Stoe IPDS II diffractometer | 3260 independent reflections |
Radiation source: fine-focus sealed tube | 1152 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.181 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.0°, θmin = 1.8° |
φ scans | h = −10→10 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −28→27 |
Tmin = 0.971, Tmax = 0.998 | l = −20→20 |
17381 measured reflections |
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)] = 0.074 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0354P)2] where P = (Fo2 + 2Fc2)/3 |
3260 reflections | (Δ/σ)max < 0.001 |
201 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.14 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 | ||
C4 | 0.1483 (5) | 0.50281 (17) | 0.1250 (2) | 0.0544 (10) | |
O1 | −0.1193 (3) | 0.38448 (12) | 0.19682 (19) | 0.0728 (9) | |
C12 | 0.1553 (5) | 0.24147 (17) | 0.2787 (3) | 0.0579 (11) | |
C6 | −0.0592 (4) | 0.43634 (17) | 0.1642 (3) | 0.0539 (10) | |
C16 | 0.2424 (5) | 0.1874 (2) | 0.3145 (3) | 0.0675 (12) | |
C9 | −0.0152 (4) | 0.33839 (18) | 0.2220 (3) | 0.0584 (11) | |
C5 | 0.1016 (4) | 0.44875 (17) | 0.1597 (3) | 0.0562 (11) | |
H5 | 0.1766 | 0.4216 | 0.1795 | 0.067* | |
C13 | 0.1343 (5) | 0.24997 (19) | 0.1934 (3) | 0.0701 (12) | |
H13 | 0.1783 | 0.2233 | 0.1550 | 0.084* | |
O2 | −0.0564 (4) | 0.37389 (13) | 0.3586 (2) | 0.0832 (9) | |
C2 | 0.3155 (6) | 0.51741 (19) | 0.1198 (3) | 0.0724 (13) | |
C7 | −0.1719 (5) | 0.47659 (19) | 0.1358 (3) | 0.0627 (11) | |
H7 | −0.2797 | 0.4675 | 0.1397 | 0.075* | |
C8 | −0.1246 (5) | 0.5301 (2) | 0.1018 (3) | 0.0638 (12) | |
H8 | −0.2010 | 0.5570 | 0.0829 | 0.077* | |
O3 | 0.2541 (5) | 0.18088 (15) | 0.3902 (2) | 0.1023 (12) | |
C3 | 0.0368 (5) | 0.54463 (17) | 0.0952 (3) | 0.0572 (11) | |
C1 | 0.0862 (6) | 0.5999 (2) | 0.0580 (3) | 0.0707 (13) | |
C11 | 0.0930 (4) | 0.28191 (17) | 0.3359 (3) | 0.0599 (11) | |
H11 | 0.1084 | 0.2760 | 0.3934 | 0.072* | |
N2 | 0.4481 (5) | 0.52921 (17) | 0.1165 (3) | 0.1011 (16) | |
C10 | 0.0073 (4) | 0.33154 (17) | 0.3078 (3) | 0.0575 (11) | |
N1 | 0.1280 (6) | 0.64428 (19) | 0.0293 (3) | 0.0973 (14) | |
C14 | 0.0457 (5) | 0.29921 (19) | 0.1649 (3) | 0.0718 (13) | |
H14 | 0.0289 | 0.3050 | 0.1075 | 0.086* | |
C17 | 0.3082 (6) | 0.14334 (18) | 0.2550 (3) | 0.0889 (16) | |
H17A | 0.3795 | 0.1629 | 0.2166 | 0.133* | |
H17B | 0.2228 | 0.1252 | 0.2239 | 0.133* | |
H17C | 0.3649 | 0.1132 | 0.2857 | 0.133* | |
C15 | −0.0489 (8) | 0.3646 (3) | 0.4476 (3) | 0.124 (2) | |
H15A | −0.1037 | 0.3283 | 0.4617 | 0.187* | |
H15B | −0.0984 | 0.3975 | 0.4761 | 0.187* | |
H15C | 0.0605 | 0.3616 | 0.4648 | 0.187* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C4 | 0.046 (2) | 0.050 (2) | 0.067 (3) | 0.0064 (19) | −0.004 (2) | 0.000 (2) |
O1 | 0.0455 (16) | 0.0671 (19) | 0.106 (2) | 0.0053 (15) | −0.0022 (17) | 0.0257 (17) |
C12 | 0.052 (2) | 0.051 (2) | 0.071 (3) | −0.002 (2) | 0.003 (2) | 0.003 (2) |
C6 | 0.045 (2) | 0.056 (2) | 0.061 (3) | 0.008 (2) | 0.000 (2) | 0.008 (2) |
C16 | 0.065 (3) | 0.057 (3) | 0.081 (3) | −0.003 (2) | 0.000 (3) | 0.007 (3) |
C9 | 0.046 (2) | 0.055 (3) | 0.074 (3) | −0.002 (2) | −0.004 (2) | 0.018 (2) |
C5 | 0.047 (2) | 0.053 (2) | 0.068 (3) | 0.0086 (19) | −0.006 (2) | 0.005 (2) |
C13 | 0.073 (3) | 0.062 (3) | 0.076 (3) | 0.001 (2) | 0.009 (3) | −0.005 (2) |
O2 | 0.085 (2) | 0.079 (2) | 0.086 (2) | 0.0229 (18) | −0.001 (2) | −0.0094 (19) |
C2 | 0.057 (3) | 0.053 (3) | 0.107 (4) | 0.005 (2) | −0.006 (3) | 0.014 (3) |
C7 | 0.043 (2) | 0.073 (3) | 0.072 (3) | 0.014 (2) | −0.005 (2) | 0.006 (2) |
C8 | 0.057 (3) | 0.076 (3) | 0.059 (3) | 0.017 (2) | −0.009 (2) | 0.006 (2) |
O3 | 0.128 (3) | 0.084 (2) | 0.095 (3) | 0.023 (2) | −0.012 (3) | 0.015 (2) |
C3 | 0.062 (3) | 0.047 (2) | 0.063 (3) | 0.010 (2) | 0.000 (2) | 0.000 (2) |
C1 | 0.077 (3) | 0.061 (3) | 0.074 (3) | 0.010 (3) | −0.009 (3) | 0.003 (3) |
C11 | 0.059 (3) | 0.056 (2) | 0.064 (3) | −0.007 (2) | −0.001 (2) | 0.009 (2) |
N2 | 0.061 (2) | 0.076 (3) | 0.166 (5) | −0.001 (2) | −0.001 (3) | 0.021 (3) |
C10 | 0.050 (2) | 0.043 (2) | 0.080 (3) | 0.0018 (19) | 0.001 (2) | −0.006 (2) |
N1 | 0.116 (4) | 0.073 (3) | 0.103 (3) | 0.003 (3) | −0.008 (3) | 0.024 (2) |
C14 | 0.069 (3) | 0.068 (3) | 0.079 (3) | 0.008 (2) | 0.003 (3) | −0.001 (3) |
C17 | 0.086 (4) | 0.062 (3) | 0.119 (4) | 0.014 (2) | 0.005 (3) | 0.001 (3) |
C15 | 0.154 (6) | 0.142 (5) | 0.077 (4) | 0.048 (5) | 0.000 (4) | −0.020 (3) |
C4—C5 | 1.388 (5) | O2—C15 | 1.427 (5) |
C4—C3 | 1.407 (5) | C2—N2 | 1.145 (5) |
C4—C2 | 1.444 (6) | C7—C8 | 1.375 (5) |
O1—C6 | 1.369 (4) | C7—H7 | 0.9300 |
O1—C9 | 1.411 (4) | C8—C3 | 1.397 (5) |
C12—C13 | 1.377 (5) | C8—H8 | 0.9300 |
C12—C11 | 1.385 (5) | C3—C1 | 1.433 (6) |
C12—C16 | 1.525 (6) | C1—N1 | 1.150 (5) |
C6—C5 | 1.380 (5) | C11—C10 | 1.399 (5) |
C6—C7 | 1.383 (5) | C11—H11 | 0.9300 |
C16—O3 | 1.213 (5) | C14—H14 | 0.9300 |
C16—C17 | 1.473 (6) | C17—H17A | 0.9600 |
C9—C14 | 1.361 (5) | C17—H17B | 0.9600 |
C9—C10 | 1.382 (5) | C17—H17C | 0.9600 |
C5—H5 | 0.9300 | C15—H15A | 0.9600 |
C13—C14 | 1.406 (6) | C15—H15B | 0.9600 |
C13—H13 | 0.9300 | C15—H15C | 0.9600 |
O2—C10 | 1.355 (4) | ||
C5—C4—C3 | 121.8 (4) | C7—C8—H8 | 119.6 |
C5—C4—C2 | 119.7 (4) | C3—C8—H8 | 119.6 |
C3—C4—C2 | 118.5 (4) | C8—C3—C4 | 117.7 (4) |
C6—O1—C9 | 120.1 (3) | C8—C3—C1 | 120.8 (4) |
C13—C12—C11 | 120.3 (4) | C4—C3—C1 | 121.4 (4) |
C13—C12—C16 | 122.5 (4) | N1—C1—C3 | 178.8 (5) |
C11—C12—C16 | 117.2 (4) | C12—C11—C10 | 120.4 (4) |
O1—C6—C5 | 123.4 (3) | C12—C11—H11 | 119.8 |
O1—C6—C7 | 115.2 (3) | C10—C11—H11 | 119.8 |
C5—C6—C7 | 121.4 (4) | O2—C10—C9 | 117.0 (4) |
O3—C16—C17 | 121.4 (5) | O2—C10—C11 | 124.8 (4) |
O3—C16—C12 | 120.2 (5) | C9—C10—C11 | 118.2 (4) |
C17—C16—C12 | 118.4 (4) | C9—C14—C13 | 119.5 (4) |
C14—C9—C10 | 122.1 (4) | C9—C14—H14 | 120.3 |
C14—C9—O1 | 121.2 (4) | C13—C14—H14 | 120.3 |
C10—C9—O1 | 116.4 (4) | C16—C17—H17A | 109.5 |
C6—C5—C4 | 118.2 (4) | C16—C17—H17B | 109.5 |
C6—C5—H5 | 120.9 | H17A—C17—H17B | 109.5 |
C4—C5—H5 | 120.9 | C16—C17—H17C | 109.5 |
C12—C13—C14 | 119.5 (4) | H17A—C17—H17C | 109.5 |
C12—C13—H13 | 120.3 | H17B—C17—H17C | 109.5 |
C14—C13—H13 | 120.3 | O2—C15—H15A | 109.5 |
C10—O2—C15 | 117.9 (4) | O2—C15—H15B | 109.5 |
N2—C2—C4 | 179.3 (6) | H15A—C15—H15B | 109.5 |
C8—C7—C6 | 120.0 (4) | O2—C15—H15C | 109.5 |
C8—C7—H7 | 120.0 | H15A—C15—H15C | 109.5 |
C6—C7—H7 | 120.0 | H15B—C15—H15C | 109.5 |
C7—C8—C3 | 120.9 (4) |