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
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.124
- Data-to-parameter ratio = 9.4
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 64.99 Deg.
Author Response: ...'see _exptl_special_details' |
Alert level C REFNR01_ALERT_3_C Ratio of reflections to parameters is < 10 for a centrosymmetric structure sine(theta)/lambda 0.5878 Proportion of unique data used 1.0000 Ratio reflections to parameters 9.3756 THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5878 PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]..... 64.99 Deg. PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.38 PLAT420_ALERT_2_C D-H Without Acceptor N18 - H182 ... ?
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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: 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. |
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