Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805003855/lh6363sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805003855/lh6363Isup2.hkl |
CCDC reference: 269815
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.052
- wR factor = 0.156
- Data-to-parameter ratio = 9.7
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT725_ALERT_1_A D-H Calc 0.91(3), Rep 1.08000 Dev... 0.17 Ang. C1 -H1 1.555 1.555
Author Response: ...see _publ_section_exptl_refinement |
PLAT725_ALERT_1_A D-H Calc 0.88(3), Rep 1.08000 Dev... 0.20 Ang. C2 -H2 1.555 1.555
Author Response: ...see _publ_section_exptl_refinement |
PLAT725_ALERT_1_A D-H Calc 0.91(3), Rep 1.08000 Dev... 0.17 Ang. C3 -H3 1.555 1.555
Author Response: ...see _publ_section_exptl_refinement |
PLAT726_ALERT_1_A H...A Calc 2.57(3), Rep 2.46000 Dev... 0.11 Ang. H1 -O2 1.555 5.766
Author Response: ...see _publ_section_exptl_refinement |
PLAT726_ALERT_1_A H...A Calc 2.75(3), Rep 2.63000 Dev... 0.12 Ang. H2 -O2 1.555 5.766
Author Response: ...see _publ_section_exptl_refinement |
PLAT726_ALERT_1_A H...A Calc 2.51(3), Rep 2.34000 Dev... 0.17 Ang. H3 -O1 1.555 1.556
Author Response: ...see _publ_section_exptl_refinement |
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.72 PLAT355_ALERT_3_C Long O-H Bond (0.82A) O2 - H9 ... 1.01 Ang. PLAT355_ALERT_3_C Long O-H Bond (0.82A) O2 - H10 ... 1.01 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. O2 .. 2.63 Ang. PLAT707_ALERT_1_C D...A Calc 3.183(4), Rep 3.178(4), Dev.. 1.25 Sigma C1 -O2 1.555 5.766 PLAT707_ALERT_1_C D...A Calc 3.391(3), Rep 3.386(4), Dev.. 1.67 Sigma C3 -O1 1.555 1.556 PLAT728_ALERT_1_C D-H..A Calc 125(2), Rep 123.00 Dev... 2.00 Deg. C1 -H1 -O2 1.555 1.555 5.766 PLAT728_ALERT_1_C D-H..A Calc 121(2), Rep 119.00 Dev... 2.00 Deg. C2 -H2 -O2 1.555 1.555 5.766 PLAT731_ALERT_1_C Bond Calc 1.01(5), Rep 1.01(2) ...... 2.50 su-Rat O2 -H9 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 1.01(5), Rep 1.01(2) ...... 2.50 su-Rat O2 -H10 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 1.01(5), Rep 1.01(2) ...... 2.50 su-Rat O2 -H9 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 1.01(5), Rep 1.01(2) ...... 2.50 su-Rat O2 -H10 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.84(5), Rep 1.83(2) ...... 2.50 su-Rat H9 -O1 1.555 1.555 PLAT745_ALERT_1_C D-H Calc 0.91(3), Rep 1.08000 ...... Missing su C1 -H1 1.555 1.555 PLAT745_ALERT_1_C D-H Calc 0.88(3), Rep 1.08000 ...... Missing su C2 -H2 1.555 1.555 PLAT745_ALERT_1_C D-H Calc 0.91(3), Rep 1.08000 ...... Missing su C3 -H3 1.555 1.555 PLAT746_ALERT_1_C H...A Calc 2.57(3), Rep 2.46000 ...... Missing su H1 -O2 1.555 5.766 PLAT746_ALERT_1_C H...A Calc 2.75(3), Rep 2.63000 ...... Missing su H2 -O2 1.555 5.766 PLAT746_ALERT_1_C H...A Calc 2.51(3), Rep 2.34000 ...... Missing su H3 -O1 1.555 1.556
6 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 20 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 22 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Bruker, 1999); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: X-SEED.
C15H11N3O2·2H2O | F(000) = 632 |
Mr = 301.30 | Dx = 1.435 Mg m−3 |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 22 reflections |
a = 7.2590 (6) Å | θ = 23.5–26.8° |
b = 25.872 (3) Å | µ = 0.11 mm−1 |
c = 7.4250 (15) Å | T = 298 K |
V = 1394.5 (3) Å3 | Transparent plate, colorless |
Z = 4 | 0.42 × 0.36 × 0.10 mm |
Siemens P4 diffractometer | Rint = 0.024 |
Radiation source: fine-focus sealed tube | θmax = 25.4°, θmin = 2.9° |
Graphite monochromator | h = −8→1 |
θ/2θ scans | k = −1→31 |
1830 measured reflections | l = −1→8 |
1302 independent reflections | 3 standard reflections every 97 reflections |
868 reflections with I > 2σ(I) | intensity decay: <3% |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.156 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0881P)2] where P = (Fo2 + 2Fc2)/3 |
1302 reflections | (Δ/σ)max < 0.001 |
134 parameters | Δρmax = 0.18 e Å−3 |
2 restraints | Δρmin = −0.23 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 | ||
O1 | 0.7717 (3) | 0.38951 (7) | 0.3949 (2) | 0.0510 (6) | |
O2 | 1.0139 (4) | 0.46391 (10) | 0.2452 (4) | 0.0747 (8) | |
N1 | 0.7551 (3) | 0.38574 (8) | 0.5712 (3) | 0.0352 (6) | |
N2 | 0.6973 (4) | 0.2500 | 0.6188 (4) | 0.0315 (7) | |
C1 | 0.7991 (4) | 0.42728 (11) | 0.6739 (4) | 0.0425 (7) | |
C2 | 0.7891 (4) | 0.42533 (12) | 0.8576 (4) | 0.0447 (8) | |
C3 | 0.7341 (4) | 0.38046 (11) | 0.9408 (4) | 0.0443 (7) | |
C4 | 0.6897 (4) | 0.33842 (11) | 0.8357 (4) | 0.0385 (7) | |
C5 | 0.7000 (3) | 0.34040 (9) | 0.6484 (3) | 0.0312 (6) | |
C6 | 0.6546 (3) | 0.29476 (9) | 0.5378 (3) | 0.0308 (6) | |
C7 | 0.5668 (4) | 0.29625 (11) | 0.3710 (4) | 0.0363 (7) | |
C8 | 0.5221 (5) | 0.2500 | 0.2901 (5) | 0.0361 (9) | |
H1 | 0.841 (4) | 0.4554 (11) | 0.612 (4) | 0.051 (9)* | |
H2 | 0.825 (4) | 0.4524 (12) | 0.921 (4) | 0.057 (9)* | |
H3 | 0.721 (4) | 0.3790 (11) | 1.062 (4) | 0.050 (9)* | |
H4 | 0.647 (4) | 0.3088 (11) | 0.884 (4) | 0.039 (7)* | |
H7 | 0.538 (4) | 0.3253 (12) | 0.318 (4) | 0.038 (8)* | |
H8 | 0.459 (5) | 0.2500 | 0.172 (5) | 0.035 (10)* | |
H9 | 0.941 (7) | 0.4358 (17) | 0.307 (7) | 0.16 (2)* | |
H10 | 1.097 (8) | 0.4380 (19) | 0.183 (7) | 0.16 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0737 (14) | 0.0468 (12) | 0.0325 (10) | −0.0149 (11) | 0.0008 (9) | 0.0064 (9) |
O2 | 0.0902 (19) | 0.0542 (14) | 0.0796 (19) | −0.0127 (14) | 0.0090 (16) | 0.0009 (15) |
N1 | 0.0384 (12) | 0.0345 (11) | 0.0328 (11) | −0.0002 (10) | −0.0023 (9) | 0.0008 (10) |
N2 | 0.0321 (15) | 0.0327 (16) | 0.0296 (15) | 0.000 | 0.0003 (13) | 0.000 |
C1 | 0.0477 (17) | 0.0323 (15) | 0.0474 (17) | −0.0038 (13) | −0.0027 (14) | 0.0008 (13) |
C2 | 0.0476 (17) | 0.0398 (16) | 0.0467 (17) | 0.0017 (13) | −0.0054 (14) | −0.0139 (14) |
C3 | 0.0504 (16) | 0.0507 (17) | 0.0317 (15) | 0.0058 (14) | −0.0003 (13) | −0.0058 (13) |
C4 | 0.0449 (16) | 0.0360 (15) | 0.0345 (14) | 0.0018 (12) | 0.0024 (12) | 0.0007 (13) |
C5 | 0.0303 (13) | 0.0325 (14) | 0.0307 (13) | 0.0028 (10) | −0.0002 (11) | 0.0013 (11) |
C6 | 0.0288 (12) | 0.0331 (13) | 0.0305 (13) | 0.0025 (11) | 0.0026 (11) | 0.0021 (11) |
C7 | 0.0381 (13) | 0.0365 (15) | 0.0345 (15) | 0.0036 (12) | −0.0018 (12) | 0.0059 (13) |
C8 | 0.0349 (19) | 0.044 (2) | 0.029 (2) | 0.000 | −0.0064 (16) | 0.000 |
O1—N1 | 1.318 (3) | C3—C4 | 1.377 (4) |
O2—H9 | 1.01 (2) | C3—H3 | 0.91 (3) |
O2—H10 | 1.01 (2) | C4—C5 | 1.394 (4) |
N1—C1 | 1.356 (3) | C4—H4 | 0.90 (3) |
N1—C5 | 1.365 (3) | C5—C6 | 1.476 (3) |
N2—C6i | 1.341 (3) | C6—C7 | 1.394 (4) |
N2—C6 | 1.341 (3) | C7—C8 | 1.378 (3) |
C1—C2 | 1.367 (4) | C7—H7 | 0.87 (3) |
C1—H1 | 0.91 (3) | C8—C7i | 1.378 (3) |
C2—C3 | 1.374 (4) | C8—H8 | 0.99 (4) |
C2—H2 | 0.88 (3) | ||
H9—O2—H10 | 92 (4) | C3—C4—H4 | 121.6 (17) |
O1—N1—C1 | 118.6 (2) | C5—C4—H4 | 116.7 (17) |
O1—N1—C5 | 120.5 (2) | N1—C5—C4 | 117.8 (2) |
C1—N1—C5 | 120.9 (2) | N1—C5—C6 | 121.3 (2) |
C6i—N2—C6 | 119.4 (3) | C4—C5—C6 | 120.9 (2) |
N1—C1—C2 | 121.3 (3) | N2—C6—C7 | 121.9 (2) |
N1—C1—H1 | 115.5 (18) | N2—C6—C5 | 112.9 (2) |
C2—C1—H1 | 123.2 (18) | C7—C6—C5 | 125.1 (2) |
C1—C2—C3 | 119.7 (3) | C8—C7—C6 | 118.1 (3) |
C1—C2—H2 | 119 (2) | C8—C7—H7 | 119.9 (18) |
C3—C2—H2 | 121 (2) | C6—C7—H7 | 122.0 (18) |
C2—C3—C4 | 118.7 (3) | C7—C8—C7i | 120.6 (3) |
C2—C3—H3 | 120.7 (19) | C7—C8—H8 | 119.70 (17) |
C4—C3—H3 | 120.5 (19) | C7i—C8—H8 | 119.70 (17) |
C3—C4—C5 | 121.6 (3) | ||
O1—N1—C1—C2 | −178.4 (3) | C3—C4—C5—C6 | 179.1 (2) |
C5—N1—C1—C2 | −0.3 (4) | C6i—N2—C6—C7 | 0.0 (4) |
N1—C1—C2—C3 | 0.3 (4) | C6i—N2—C6—C5 | 176.50 (19) |
C1—C2—C3—C4 | −0.2 (4) | N1—C5—C6—N2 | 147.0 (2) |
C2—C3—C4—C5 | 0.2 (4) | C4—C5—C6—N2 | −32.4 (3) |
O1—N1—C5—C4 | 178.3 (2) | N1—C5—C6—C7 | −36.6 (3) |
C1—N1—C5—C4 | 0.3 (4) | C4—C5—C6—C7 | 144.0 (3) |
O1—N1—C5—C6 | −1.0 (4) | N2—C6—C7—C8 | 0.6 (4) |
C1—N1—C5—C6 | −179.0 (2) | C5—C6—C7—C8 | −175.4 (3) |
C3—C4—C5—N1 | −0.3 (4) | C6—C7—C8—C7i | −1.3 (5) |
Symmetry code: (i) x, −y+1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H9···O1 | 1.01 (2) | 1.83 (2) | 2.837 (3) | 174 (6) |
O2—H10···O1ii | 1.01 (2) | 1.89 (3) | 2.878 (4) | 168 (7) |
C1—H1···O2iii | 1.08 | 2.46 | 3.178 (4) | 123 |
C2—H2···O2iii | 1.08 | 2.63 | 3.288 (4) | 119 |
C3—H3···O1iv | 1.08 | 2.34 | 3.386 (4) | 162 |
Symmetry codes: (ii) x+1/2, y, −z+1/2; (iii) −x+2, −y+1, −z+1; (iv) x, y, z+1. |