Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804020574/hg6074sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804020574/hg6074Isup2.hkl |
CCDC reference: 251749
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.116
- Data-to-parameter ratio = 12.2
checkCIF/PLATON results
No syntax errors found
Alert level C RADNW01_ALERT_1_C The radiation wavelength lies outside the expected range for the supplied radiation type. Expected range 0.71065-0.71075 Wavelength given = 0.70930 PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C1 .. 5.27 su
Alert level G RADNW01_ALERT_1_G The radiation wavelength given implies that Mo Kalpha1 has been used. Please check that this is correct. Wavelength given = 0.70930
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 PC Software (Enraf–Nonius, 1993); cell refinement: CAD-4 PC Software; data reduction: DATRD2 in NRCVAX (Gabe et al., 1989); program(s) used to solve structure: NRCVAX SOLVER; program(s) used to refine structure: NRCVAX LSTSQ and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) in NRCVAX; software used to prepare material for publication: SHELXL97.
C15H13N3O4 | F(000) = 312 |
Mr = 299.28 | ? #Insert any comments here. |
Triclinic, P1 | Dx = 1.442 Mg m−3 |
Hall symbol: -P 1 | Melting point: 429 K |
a = 6.7094 (4) Å | Mo Kα radiation, λ = 0.70930 Å |
b = 8.8147 (6) Å | Cell parameters from 25 reflections |
c = 12.2004 (9) Å | θ = 6.1–14.0° |
α = 72.908 (6)° | µ = 0.11 mm−1 |
β = 87.720 (6)° | T = 293 K |
γ = 88.718 (6)° | Needle, yellow |
V = 689.09 (8) Å3 | 0.51 × 0.20 × 0.12 mm |
Z = 2 |
Nonius CAD-4 diffractometer | Rint = 0.007 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 1.7° |
Graphite monochromator | h = −7→7 |
ω scans | k = 0→10 |
2698 measured reflections | l = −13→14 |
2442 independent reflections | 3 standard reflections every 120 min |
1692 reflections with Inet > 2σ(Inet) | intensity decay: 1.2% |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0515P)2 + 0.1899P] where P = (Fo2 + 2Fc2)/3 |
2442 reflections | (Δ/σ)max = 0.001 |
200 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.17 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. TABLE of LEAST SQUARES PLANES ——- Plane No. 1 ——— Equation of the plane: 3.4329 (15)X + 4.087 (4)Y + 10.3793 (21)Z = 3.4664 (9) Distances(A) to the plane from the atoms in the plane. N9 - 0.0091 (18) C1 0.0074 (22) C2 - 0.0407 (24) C3 - 0.0330 (24) C4 0.0069 (22) C4a 0.0339 (20) C4b 0.0332 (19) C5 0.0122 (22) C6 - 0.0266 (22) C7 - 0.0258 (23) C8 - 0.0083 (22) C8a 0.0118 (20) C9a 0.0220 (21) Chi squared for this plane 1568.151 Distances(A) to the plane from the atoms out of the plane. N1 0.1750 (24) N6 - 0.0950 (25) C10 - 0.279 (3) C12 - 0.027 (3) ——- Plane No. 2 ——— Equation of the plane: 5.368 (12)X - 0.713 (24)Y + 6.931 (16)Z = 4.078 (13) Distances(A) to the plane from the atoms in the plane. N1 0.000 (3) O1a 0.0000 (22) O1b 0.0000 (22) ——- Plane No. 3 ——— Equation of the plane: 3.472 (17)X + 3.382 (17)Y + 10.562 (21)Z = 3.633 (21) Distances(A) to the plane from the atoms in the plane. N6 0.000 (3) O6a 0.0000 (23) O6b 0.0000 (23) ——- Plane No. 4 ——— Equation of the plane: 6.336 (7)X - 0.662 (11)Y - 3.55 (4)Z = 1.026 (10) Distances(A) to the plane from the atoms in the plane. N9 0.0000 (22) C10 0.000 (3) C11 0.000 (4) ———————————————————————- Dihedral angle between planes A and B A B Angle(°) 1 2 37.24 (9) 1 3 5.27 (15) 1 4 77.86 (17) 2 3 33.58 (10) 2 4 54.63 (23) 3 4 77.85 (25) |
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) | |
O1A | 0.6810 (3) | 0.2723 (2) | 0.08878 (15) | 0.0680 (5) | |
O1B | 0.8095 (3) | 0.1447 (2) | −0.02367 (16) | 0.0776 (6) | |
O6A | −0.4115 (3) | −0.1958 (2) | 0.54203 (16) | 0.0796 (6) | |
O6B | −0.2239 (3) | −0.3960 (2) | 0.54437 (17) | 0.0837 (6) | |
N1 | 0.7038 (3) | 0.1512 (3) | 0.05920 (16) | 0.0542 (5) | |
N6 | −0.2610 (3) | −0.2535 (2) | 0.51102 (16) | 0.0557 (5) | |
N9 | 0.2828 (3) | 0.11477 (19) | 0.19406 (14) | 0.0431 (4) | |
C1 | 0.6113 (3) | 0.0053 (2) | 0.13046 (17) | 0.0441 (5) | |
C2 | 0.7224 (3) | −0.1326 (3) | 0.14370 (19) | 0.0503 (6) | |
H2 | 0.8401 | −0.1286 | 0.1000 | 0.060* | |
C3 | 0.6650 (3) | −0.2765 (3) | 0.2196 (2) | 0.0495 (6) | |
C4 | 0.4884 (3) | −0.2814 (2) | 0.28391 (19) | 0.0463 (5) | |
H4 | 0.4472 | −0.3764 | 0.3360 | 0.056* | |
C4A | 0.3738 (3) | −0.1452 (2) | 0.27068 (17) | 0.0406 (5) | |
C4B | 0.1846 (3) | −0.1191 (2) | 0.32324 (17) | 0.0400 (5) | |
C5 | 0.0552 (3) | −0.2172 (2) | 0.40242 (17) | 0.0430 (5) | |
H5 | 0.0853 | −0.3240 | 0.4355 | 0.052* | |
C6 | −0.1196 (3) | −0.1510 (2) | 0.43046 (17) | 0.0435 (5) | |
C7 | −0.1698 (3) | 0.0091 (3) | 0.38410 (18) | 0.0467 (5) | |
H7 | −0.2888 | 0.0491 | 0.4067 | 0.056* | |
C8 | −0.0423 (3) | 0.1072 (2) | 0.30493 (18) | 0.0463 (5) | |
H8 | −0.0734 | 0.2141 | 0.2730 | 0.056* | |
C8A | 0.1347 (3) | 0.0423 (2) | 0.27372 (17) | 0.0409 (5) | |
C9A | 0.4304 (3) | 0.0021 (2) | 0.19297 (17) | 0.0409 (5) | |
C10 | 0.2544 (4) | 0.2749 (3) | 0.1143 (2) | 0.0551 (6) | |
H10A | 0.1179 | 0.2864 | 0.0895 | 0.066* | |
H10B | 0.3415 | 0.2868 | 0.0470 | 0.066* | |
C11 | 0.2973 (4) | 0.4046 (3) | 0.1671 (2) | 0.0719 (8) | |
H11A | 0.2752 | 0.5061 | 0.1121 | 0.108* | |
H11B | 0.4335 | 0.3961 | 0.1896 | 0.108* | |
H11C | 0.2104 | 0.3943 | 0.2333 | 0.108* | |
C12 | 0.7964 (4) | −0.4229 (3) | 0.2344 (2) | 0.0685 (7) | |
H12A | 0.7346 | −0.5116 | 0.2898 | 0.103* | 0.50 |
H12B | 0.9241 | −0.4043 | 0.2606 | 0.103* | 0.50 |
H12C | 0.8137 | −0.4455 | 0.1623 | 0.103* | 0.50 |
H12D | 0.9136 | −0.3960 | 0.1853 | 0.103* | 0.50 |
H12E | 0.7242 | −0.5033 | 0.2145 | 0.103* | 0.50 |
H12F | 0.8346 | −0.4621 | 0.3128 | 0.103* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0670 (12) | 0.0528 (10) | 0.0792 (12) | −0.0106 (9) | 0.0062 (9) | −0.0119 (9) |
O1B | 0.0636 (12) | 0.0942 (14) | 0.0665 (11) | −0.0116 (10) | 0.0259 (10) | −0.0130 (10) |
O6A | 0.0573 (12) | 0.0864 (13) | 0.0840 (13) | 0.0101 (10) | 0.0310 (10) | −0.0129 (10) |
O6B | 0.0825 (14) | 0.0548 (11) | 0.0975 (15) | −0.0010 (10) | 0.0400 (11) | −0.0026 (10) |
N1 | 0.0390 (11) | 0.0673 (14) | 0.0512 (11) | −0.0076 (10) | 0.0029 (9) | −0.0096 (10) |
N6 | 0.0489 (13) | 0.0616 (13) | 0.0530 (11) | −0.0010 (10) | 0.0117 (10) | −0.0128 (10) |
N9 | 0.0395 (10) | 0.0387 (9) | 0.0477 (10) | −0.0008 (8) | 0.0031 (8) | −0.0079 (8) |
C1 | 0.0372 (12) | 0.0493 (13) | 0.0455 (12) | −0.0075 (10) | 0.0030 (10) | −0.0137 (10) |
C2 | 0.0371 (12) | 0.0624 (15) | 0.0570 (14) | −0.0021 (11) | 0.0050 (10) | −0.0271 (12) |
C3 | 0.0394 (13) | 0.0525 (13) | 0.0628 (14) | 0.0037 (10) | −0.0015 (11) | −0.0269 (11) |
C4 | 0.0419 (13) | 0.0413 (12) | 0.0566 (13) | −0.0004 (10) | 0.0015 (11) | −0.0161 (10) |
C4A | 0.0361 (11) | 0.0402 (11) | 0.0468 (12) | −0.0013 (9) | 0.0010 (9) | −0.0150 (9) |
C4B | 0.0362 (12) | 0.0406 (11) | 0.0434 (11) | −0.0002 (9) | 0.0012 (9) | −0.0130 (9) |
C5 | 0.0429 (13) | 0.0390 (12) | 0.0457 (12) | 0.0005 (10) | 0.0018 (10) | −0.0107 (9) |
C6 | 0.0383 (12) | 0.0484 (12) | 0.0429 (11) | −0.0014 (10) | 0.0048 (9) | −0.0128 (10) |
C7 | 0.0364 (12) | 0.0545 (13) | 0.0510 (12) | 0.0059 (10) | 0.0012 (10) | −0.0192 (10) |
C8 | 0.0444 (13) | 0.0401 (12) | 0.0545 (13) | 0.0069 (10) | −0.0026 (10) | −0.0142 (10) |
C8A | 0.0365 (12) | 0.0423 (11) | 0.0449 (12) | −0.0003 (9) | −0.0016 (9) | −0.0142 (9) |
C9A | 0.0366 (12) | 0.0446 (12) | 0.0435 (11) | −0.0011 (9) | −0.0016 (9) | −0.0157 (9) |
C10 | 0.0476 (14) | 0.0520 (14) | 0.0573 (14) | 0.0011 (11) | 0.0003 (11) | −0.0035 (11) |
C11 | 0.0808 (19) | 0.0473 (14) | 0.0827 (19) | −0.0008 (13) | 0.0083 (15) | −0.0131 (13) |
C12 | 0.0522 (15) | 0.0608 (16) | 0.099 (2) | 0.0120 (12) | 0.0028 (14) | −0.0350 (15) |
O1A—N1 | 1.228 (2) | C4B—C8A | 1.411 (3) |
O1B—N1 | 1.226 (2) | C5—C6 | 1.374 (3) |
O6A—N6 | 1.217 (2) | C5—H5 | 0.9300 |
O6B—N6 | 1.224 (2) | C6—C7 | 1.396 (3) |
N1—C1 | 1.460 (3) | C7—C8 | 1.374 (3) |
N6—C6 | 1.458 (3) | C7—H7 | 0.9300 |
N9—C8A | 1.388 (3) | C8—C8A | 1.395 (3) |
N9—C9A | 1.390 (3) | C8—H8 | 0.9300 |
N9—C10 | 1.473 (3) | C10—C11 | 1.505 (3) |
C1—C2 | 1.384 (3) | C10—H10A | 0.9700 |
C1—C9A | 1.404 (3) | C10—H10B | 0.9700 |
C2—C3 | 1.385 (3) | C11—H11A | 0.9600 |
C2—H2 | 0.9300 | C11—H11B | 0.9600 |
C3—C4 | 1.389 (3) | C11—H11C | 0.9600 |
C3—C12 | 1.516 (3) | C12—H12A | 0.9600 |
C4—C4A | 1.383 (3) | C12—H12B | 0.9600 |
C4—H4 | 0.9300 | C12—H12C | 0.9600 |
C4A—C9A | 1.414 (3) | C12—H12D | 0.9600 |
C4A—C4B | 1.444 (3) | C12—H12E | 0.9600 |
C4B—C5 | 1.382 (3) | C12—H12F | 0.9600 |
O1B—N1—O1A | 123.2 (2) | N9—C8A—C8 | 129.08 (19) |
O1B—N1—C1 | 118.3 (2) | N9—C8A—C4B | 109.70 (17) |
O1A—N1—C1 | 118.41 (19) | C8—C8A—C4B | 121.21 (19) |
O6A—N6—O6B | 122.3 (2) | N9—C9A—C1 | 133.76 (19) |
O6A—N6—C6 | 119.5 (2) | N9—C9A—C4A | 109.20 (17) |
O6B—N6—C6 | 118.22 (18) | C1—C9A—C4A | 117.00 (19) |
C8A—N9—C9A | 108.03 (16) | N9—C10—C11 | 112.8 (2) |
C8A—N9—C10 | 121.53 (17) | N9—C10—H10A | 109.0 |
C9A—N9—C10 | 129.51 (18) | C11—C10—H10A | 109.0 |
C2—C1—C9A | 120.07 (19) | N9—C10—H10B | 109.0 |
C2—C1—N1 | 116.07 (19) | C11—C10—H10B | 109.0 |
C9A—C1—N1 | 123.54 (19) | H10A—C10—H10B | 107.8 |
C1—C2—C3 | 122.4 (2) | C10—C11—H11A | 109.5 |
C1—C2—H2 | 118.8 | C10—C11—H11B | 109.5 |
C3—C2—H2 | 118.8 | H11A—C11—H11B | 109.5 |
C2—C3—C4 | 118.3 (2) | C10—C11—H11C | 109.5 |
C2—C3—C12 | 120.4 (2) | H11A—C11—H11C | 109.5 |
C4—C3—C12 | 121.3 (2) | H11B—C11—H11C | 109.5 |
C4A—C4—C3 | 120.1 (2) | C3—C12—H12A | 109.5 |
C4A—C4—H4 | 119.9 | C3—C12—H12B | 109.5 |
C3—C4—H4 | 119.9 | H12A—C12—H12B | 109.5 |
C4—C4A—C9A | 122.05 (19) | C3—C12—H12C | 109.5 |
C4—C4A—C4B | 131.18 (19) | H12A—C12—H12C | 109.5 |
C9A—C4A—C4B | 106.74 (18) | H12B—C12—H12C | 109.5 |
C5—C4B—C8A | 120.16 (18) | C3—C12—H12D | 109.5 |
C5—C4B—C4A | 133.50 (19) | H12A—C12—H12D | 141.1 |
C8A—C4B—C4A | 106.30 (18) | H12B—C12—H12D | 56.3 |
C6—C5—C4B | 117.50 (19) | H12C—C12—H12D | 56.3 |
C6—C5—H5 | 121.3 | C3—C12—H12E | 109.5 |
C4B—C5—H5 | 121.3 | H12A—C12—H12E | 56.3 |
C5—C6—C7 | 123.19 (19) | H12B—C12—H12E | 141.1 |
C5—C6—N6 | 118.38 (19) | H12C—C12—H12E | 56.3 |
C7—C6—N6 | 118.42 (19) | H12D—C12—H12E | 109.5 |
C8—C7—C6 | 119.64 (19) | C3—C12—H12F | 109.5 |
C8—C7—H7 | 120.2 | H12A—C12—H12F | 56.3 |
C6—C7—H7 | 120.2 | H12B—C12—H12F | 56.3 |
C7—C8—C8A | 118.28 (19) | H12C—C12—H12F | 141.1 |
C7—C8—H8 | 120.9 | H12D—C12—H12F | 109.5 |
C8A—C8—H8 | 120.9 | H12E—C12—H12F | 109.5 |
O1B—N1—C1—C2 | 34.9 (3) | C6—C7—C8—C8A | −0.1 (3) |
O1A—N1—C1—C2 | −141.1 (2) | C9A—N9—C8A—C8 | 179.9 (2) |
O1B—N1—C1—C9A | −151.7 (2) | C10—N9—C8A—C8 | −10.1 (3) |
O1A—N1—C1—C9A | 32.3 (3) | C9A—N9—C8A—C4B | −1.1 (2) |
C9A—C1—C2—C3 | −1.7 (3) | C10—N9—C8A—C4B | 168.90 (18) |
N1—C1—C2—C3 | 172.0 (2) | C7—C8—C8A—N9 | 177.8 (2) |
C1—C2—C3—C4 | 0.3 (3) | C7—C8—C8A—C4B | −1.1 (3) |
C1—C2—C3—C12 | −177.5 (2) | C5—C4B—C8A—N9 | −177.66 (18) |
C2—C3—C4—C4A | 0.6 (3) | C4A—C4B—C8A—N9 | 0.2 (2) |
C12—C3—C4—C4A | 178.4 (2) | C5—C4B—C8A—C8 | 1.4 (3) |
C3—C4—C4A—C9A | −0.2 (3) | C4A—C4B—C8A—C8 | 179.30 (19) |
C3—C4—C4A—C4B | 177.8 (2) | C8A—N9—C9A—C1 | 179.2 (2) |
C4—C4A—C4B—C5 | −0.1 (4) | C10—N9—C9A—C1 | 10.3 (4) |
C9A—C4A—C4B—C5 | 178.2 (2) | C8A—N9—C9A—C4A | 1.5 (2) |
C4—C4A—C4B—C8A | −177.6 (2) | C10—N9—C9A—C4A | −167.38 (19) |
C9A—C4A—C4B—C8A | 0.7 (2) | C2—C1—C9A—N9 | −175.6 (2) |
C8A—C4B—C5—C6 | −0.4 (3) | N1—C1—C9A—N9 | 11.2 (4) |
C4A—C4B—C5—C6 | −177.6 (2) | C2—C1—C9A—C4A | 2.0 (3) |
C4B—C5—C6—C7 | −0.8 (3) | N1—C1—C9A—C4A | −171.21 (18) |
C4B—C5—C6—N6 | 178.08 (19) | C4—C4A—C9A—N9 | 177.09 (19) |
O6A—N6—C6—C5 | 175.9 (2) | C4B—C4A—C9A—N9 | −1.4 (2) |
O6B—N6—C6—C5 | −4.7 (3) | C4—C4A—C9A—C1 | −1.1 (3) |
O6A—N6—C6—C7 | −5.2 (3) | C4B—C4A—C9A—C1 | −179.53 (18) |
O6B—N6—C6—C7 | 174.2 (2) | C8A—N9—C10—C11 | 83.1 (3) |
C5—C6—C7—C8 | 1.1 (3) | C9A—N9—C10—C11 | −109.3 (3) |
N6—C6—C7—C8 | −177.8 (2) |
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