Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805010676/lh6401sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805010676/lh6401Isup2.hkl |
CCDC reference: 272020
Data collection: Picker Software (Picker, 1967); cell refinement: Picker Software; data reduction: Picker Software; 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.
C15H12N2O2 | Dx = 1.380 Mg m−3 |
Mr = 252.27 | Melting point: not measured K |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 5.276 (2) Å | Cell parameters from 32 reflections |
b = 9.307 (4) Å | θ = 30–54° |
c = 24.841 (7) Å | µ = 0.76 mm−1 |
β = 95.64 (2)° | T = 294 K |
V = 1213.9 (8) Å3 | Needle, colorless |
Z = 4 | 0.49 × 0.15 × 0.11 mm |
F(000) = 528 |
Picker FACS-1 4-circle diffractometer | 1761 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Ni-filtered radiation monochromator | θmax = 65.0°, θmin = 3.6° |
θ/2θ scan | h = 0→6 |
Absorption correction: ψ scan (North et al., 1968) | k = −10→0 |
Tmin = 0.867, Tmax = 0.917 | l = −29→28 |
2072 measured reflections | 3 standard reflections every 100 reflections |
2072 independent reflections | intensity decay: 0.7% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | All H-atom parameters refined |
wR(F2) = 0.124 | w = 1/[σ2(Fo2) + (0.1065P)2 + 0.235P] where P = (Fo2 + 2Fc2)/3 |
S = 0.81 | (Δ/σ)max = 0.001 |
2072 reflections | Δρmax = 0.16 e Å−3 |
221 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0115 (12) |
Experimental. PICKER FACS-1 mechanical limit does not allow for data collection above θ = 65° Data were collected on a crystal mounted along its long axis. |
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 | 0.3037 (3) | 0.32591 (19) | 0.59887 (7) | 0.0494 (4) | |
C2 | 0.1629 (3) | 0.23151 (19) | 0.62724 (8) | 0.0520 (5) | |
C3 | 0.0329 (3) | 0.28049 (18) | 0.66915 (8) | 0.0490 (4) | |
C4 | 0.0439 (3) | 0.42400 (17) | 0.68372 (6) | 0.0417 (4) | |
N5 | 0.1992 (2) | 0.66760 (13) | 0.66889 (5) | 0.0361 (3) | |
C6 | −0.1250 (3) | 0.85135 (16) | 0.65407 (7) | 0.0413 (4) | |
C7 | −0.2780 (3) | 0.94051 (19) | 0.62071 (8) | 0.0510 (4) | |
C8 | −0.2541 (4) | 0.9437 (2) | 0.56571 (8) | 0.0569 (5) | |
C9 | −0.0790 (4) | 0.8566 (2) | 0.54463 (7) | 0.0529 (5) | |
C10 | 0.2732 (4) | 0.6800 (2) | 0.54995 (7) | 0.0500 (4) | |
C11 | 0.4531 (3) | 0.57875 (18) | 0.58142 (7) | 0.0470 (4) | |
C12 | 0.1871 (3) | 0.51694 (16) | 0.65566 (6) | 0.0356 (4) | |
C13 | 0.3158 (3) | 0.47037 (17) | 0.61289 (6) | 0.0403 (4) | |
C14 | 0.0547 (3) | 0.76342 (15) | 0.63302 (6) | 0.0361 (4) | |
C15 | 0.0821 (3) | 0.76539 (17) | 0.57731 (6) | 0.0419 (4) | |
C16 | 0.3440 (3) | 0.72171 (15) | 0.71368 (6) | 0.0355 (4) | |
O17 | 0.3538 (2) | 0.85078 (11) | 0.72298 (5) | 0.0450 (3) | |
N18 | 0.4735 (3) | 0.62560 (17) | 0.74566 (6) | 0.0521 (4) | |
O19 | 0.2846 (4) | 0.6952 (2) | 0.50180 (6) | 0.0858 (5) | |
H1 | 0.395 (4) | 0.295 (2) | 0.5693 (9) | 0.070 (6)* | |
H2 | 0.152 (4) | 0.127 (2) | 0.6187 (8) | 0.053 (5)* | |
H3 | −0.064 (4) | 0.214 (2) | 0.6893 (8) | 0.057 (5)* | |
H4 | −0.054 (3) | 0.4616 (19) | 0.7118 (7) | 0.044 (4)* | |
H6 | −0.146 (4) | 0.848 (2) | 0.6927 (8) | 0.051 (5)* | |
H7 | −0.403 (5) | 1.003 (3) | 0.6361 (8) | 0.074 (6)* | |
H8 | −0.360 (4) | 1.007 (2) | 0.5420 (8) | 0.064 (6)* | |
H9 | −0.063 (4) | 0.857 (2) | 0.5074 (10) | 0.071 (7)* | |
H111 | 0.565 (4) | 0.635 (2) | 0.6066 (7) | 0.045 (5)* | |
H112 | 0.561 (4) | 0.533 (2) | 0.5551 (9) | 0.063 (5)* | |
H181 | 0.473 (4) | 0.534 (2) | 0.7402 (8) | 0.060 (6)* | |
H182 | 0.572 (5) | 0.668 (2) | 0.7737 (10) | 0.069 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0553 (10) | 0.0436 (9) | 0.0505 (9) | −0.0044 (7) | 0.0117 (8) | −0.0149 (7) |
C2 | 0.0594 (11) | 0.0356 (9) | 0.0605 (11) | −0.0080 (7) | 0.0031 (8) | −0.0086 (8) |
C3 | 0.0513 (9) | 0.0399 (9) | 0.0559 (10) | −0.0104 (7) | 0.0057 (8) | 0.0046 (8) |
C4 | 0.0445 (8) | 0.0422 (9) | 0.0395 (8) | −0.0014 (6) | 0.0093 (7) | 0.0016 (6) |
N5 | 0.0464 (7) | 0.0300 (6) | 0.0320 (6) | 0.0002 (5) | 0.0038 (5) | −0.0033 (5) |
C6 | 0.0429 (8) | 0.0371 (8) | 0.0439 (9) | −0.0012 (6) | 0.0047 (7) | −0.0019 (6) |
C7 | 0.0474 (9) | 0.0415 (9) | 0.0629 (11) | 0.0026 (7) | −0.0003 (8) | −0.0008 (8) |
C8 | 0.0582 (10) | 0.0489 (10) | 0.0601 (11) | 0.0003 (8) | −0.0121 (9) | 0.0100 (9) |
C9 | 0.0636 (11) | 0.0551 (11) | 0.0384 (9) | −0.0117 (8) | −0.0021 (8) | 0.0099 (8) |
C10 | 0.0596 (10) | 0.0550 (10) | 0.0373 (8) | −0.0118 (8) | 0.0149 (7) | −0.0011 (7) |
C11 | 0.0486 (9) | 0.0474 (10) | 0.0479 (9) | −0.0067 (7) | 0.0192 (8) | −0.0075 (8) |
C12 | 0.0403 (8) | 0.0316 (7) | 0.0348 (7) | −0.0015 (6) | 0.0027 (6) | −0.0031 (6) |
C13 | 0.0426 (8) | 0.0385 (9) | 0.0407 (8) | −0.0036 (6) | 0.0077 (6) | −0.0050 (6) |
C14 | 0.0404 (8) | 0.0325 (7) | 0.0354 (8) | −0.0066 (6) | 0.0037 (6) | 0.0003 (6) |
C15 | 0.0481 (9) | 0.0415 (8) | 0.0362 (8) | −0.0106 (7) | 0.0044 (6) | 0.0019 (6) |
C16 | 0.0401 (8) | 0.0349 (8) | 0.0324 (7) | −0.0002 (6) | 0.0078 (6) | −0.0026 (6) |
O17 | 0.0544 (7) | 0.0348 (6) | 0.0450 (6) | −0.0011 (5) | 0.0005 (5) | −0.0087 (5) |
N18 | 0.0659 (10) | 0.0402 (8) | 0.0466 (8) | 0.0038 (7) | −0.0122 (7) | −0.0030 (6) |
O19 | 0.1080 (12) | 0.1127 (14) | 0.0412 (7) | 0.0169 (10) | 0.0292 (8) | 0.0072 (8) |
C1—C13 | 1.389 (2) | C8—C9 | 1.371 (3) |
C1—C2 | 1.387 (3) | C8—H8 | 0.97 (2) |
C1—H1 | 0.96 (2) | C9—C15 | 1.402 (2) |
C2—C3 | 1.379 (3) | C9—H9 | 0.94 (2) |
C2—H2 | 0.99 (2) | C10—O19 | 1.212 (2) |
C3—C4 | 1.384 (2) | C10—C15 | 1.499 (2) |
C3—H3 | 0.97 (2) | C10—C11 | 1.501 (3) |
C4—C12 | 1.381 (2) | C11—C13 | 1.505 (2) |
C4—H4 | 0.974 (19) | C11—H111 | 0.971 (19) |
N5—C16 | 1.3812 (19) | C11—H112 | 1.00 (2) |
N5—C14 | 1.4271 (19) | C12—C13 | 1.385 (2) |
N5—C12 | 1.4402 (19) | C14—C15 | 1.406 (2) |
C6—C7 | 1.377 (2) | C16—O17 | 1.2234 (18) |
C6—C14 | 1.393 (2) | C16—N18 | 1.338 (2) |
C6—H6 | 0.98 (2) | N18—H181 | 0.86 (2) |
C7—C8 | 1.385 (3) | N18—H182 | 0.92 (2) |
C7—H7 | 0.99 (2) | ||
C13—C1—C2 | 119.96 (16) | O19—C10—C15 | 119.14 (18) |
C13—C1—H1 | 117.8 (14) | O19—C10—C11 | 119.80 (18) |
C2—C1—H1 | 122.2 (14) | C15—C10—C11 | 121.05 (14) |
C3—C2—C1 | 120.34 (16) | C10—C11—C13 | 112.29 (14) |
C3—C2—H2 | 117.4 (12) | C10—C11—H111 | 108.1 (11) |
C1—C2—H2 | 122.3 (12) | C13—C11—H111 | 108.6 (11) |
C2—C3—C4 | 120.35 (16) | C10—C11—H112 | 107.2 (12) |
C2—C3—H3 | 120.1 (12) | C13—C11—H112 | 112.8 (12) |
C4—C3—H3 | 119.6 (12) | H111—C11—H112 | 107.6 (16) |
C12—C4—C3 | 118.92 (15) | C4—C12—C13 | 121.63 (14) |
C12—C4—H4 | 119.5 (11) | C4—C12—N5 | 120.58 (13) |
C3—C4—H4 | 121.5 (11) | C13—C12—N5 | 117.75 (13) |
C16—N5—C14 | 119.62 (12) | C1—C13—C12 | 118.78 (14) |
C16—N5—C12 | 123.18 (12) | C1—C13—C11 | 122.08 (15) |
C14—N5—C12 | 117.20 (12) | C12—C13—C11 | 119.07 (14) |
C7—C6—C14 | 120.58 (16) | C6—C14—C15 | 120.10 (14) |
C7—C6—H6 | 119.5 (11) | C6—C14—N5 | 118.33 (13) |
C14—C6—H6 | 119.9 (11) | C15—C14—N5 | 121.50 (13) |
C8—C7—C6 | 120.13 (17) | C9—C15—C14 | 117.58 (16) |
C8—C7—H7 | 119.9 (13) | C9—C15—C10 | 117.06 (15) |
C6—C7—H7 | 120.0 (13) | C14—C15—C10 | 125.35 (15) |
C7—C8—C9 | 119.63 (17) | O17—C16—N18 | 122.31 (15) |
C7—C8—H8 | 120.6 (12) | O17—C16—N5 | 121.32 (13) |
C9—C8—H8 | 119.8 (12) | N18—C16—N5 | 116.37 (14) |
C8—C9—C15 | 121.96 (17) | C16—N18—H181 | 125.0 (14) |
C8—C9—H9 | 120.1 (14) | C16—N18—H182 | 112.6 (14) |
C15—C9—H9 | 118.0 (14) | H181—N18—H182 | 122 (2) |
C13—C1—C2—C3 | 0.5 (3) | C10—C11—C13—C12 | −67.2 (2) |
C1—C2—C3—C4 | −0.7 (3) | C7—C6—C14—C15 | 0.2 (2) |
C2—C3—C4—C12 | −0.1 (3) | C7—C6—C14—N5 | −176.79 (14) |
C14—C6—C7—C8 | −0.1 (3) | C16—N5—C14—C6 | −57.77 (19) |
C6—C7—C8—C9 | 0.6 (3) | C12—N5—C14—C6 | 122.83 (15) |
C7—C8—C9—C15 | −1.3 (3) | C16—N5—C14—C15 | 125.26 (15) |
O19—C10—C11—C13 | −126.31 (19) | C12—N5—C14—C15 | −54.15 (19) |
C15—C10—C11—C13 | 54.9 (2) | C8—C9—C15—C14 | 1.4 (3) |
C3—C4—C12—C13 | 1.1 (2) | C8—C9—C15—C10 | −177.44 (16) |
C3—C4—C12—N5 | 178.74 (14) | C6—C14—C15—C9 | −0.9 (2) |
C16—N5—C12—C4 | 76.37 (19) | N5—C14—C15—C9 | 176.07 (14) |
C14—N5—C12—C4 | −104.25 (16) | C6—C14—C15—C10 | 177.88 (15) |
C16—N5—C12—C13 | −105.92 (17) | N5—C14—C15—C10 | −5.2 (2) |
C14—N5—C12—C13 | 73.46 (18) | O19—C10—C15—C9 | 1.6 (3) |
C2—C1—C13—C12 | 0.6 (3) | C11—C10—C15—C9 | −179.64 (15) |
C2—C1—C13—C11 | −176.36 (17) | O19—C10—C15—C14 | −177.16 (18) |
C4—C12—C13—C1 | −1.4 (2) | C11—C10—C15—C14 | 1.6 (2) |
N5—C12—C13—C1 | −179.04 (14) | C14—N5—C16—O17 | −0.9 (2) |
C4—C12—C13—C11 | 175.65 (15) | C12—N5—C16—O17 | 178.42 (14) |
N5—C12—C13—C11 | −2.0 (2) | C14—N5—C16—N18 | 179.68 (14) |
C10—C11—C13—C1 | 109.72 (18) | C12—N5—C16—N18 | −1.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N18—H181···O17i | 0.86 (2) | 2.10 (2) | 2.800 (2) | 137.7 (18) |
C1—H1···O19ii | 0.96 (2) | 2.56 (2) | 3.475 (2) | 158.4 (18) |
C4—H4···O17iii | 0.974 (19) | 2.587 (18) | 3.346 (2) | 134.9 (13) |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) −x, y−1/2, −z+3/2. |