Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807011853/pk2003sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807011853/pk2003Isup2.hkl |
CCDC reference: 643074
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.004 Å
- Disorder in solvent or counterion
- R factor = 0.061
- wR factor = 0.140
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT128_ALERT_4_C Non-standard setting of Space group P2/c .... P2/n PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 H2 O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 0 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C14H11N5·0.5H2O | F(000) = 540 |
Mr = 258.29 | Dx = 1.257 Mg m−3 |
Monoclinic, P2/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yac | Cell parameters from 676 reflections |
a = 12.973 (3) Å | θ = 2.6–23.1° |
b = 7.7999 (14) Å | µ = 0.08 mm−1 |
c = 13.569 (2) Å | T = 291 K |
β = 96.300 (4)° | Block, colorless |
V = 1364.7 (4) Å3 | 0.26 × 0.22 × 0.15 mm |
Z = 4 |
Bruker SMART APEX CCD diffractometer | 2688 independent reflections |
Radiation source: sealed tube | 1706 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
φ and ω scans | θmax = 26.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −14→16 |
Tmin = 0.98, Tmax = 0.99 | k = −6→9 |
7118 measured reflections | l = −16→16 |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0658P)2] where P = (Fo2 + 2Fc2)/3 |
2680 reflections | (Δ/σ)max = 0.003 |
181 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
Experimental. Analyses for C, H and N were made on a Perkin–Elmer 240 C elemental analyser. 1H NMR spectroscopic measurements were carried out on a Bruker AM-500 NMR spectrometer, using TMS (SiMe4) as an internal reference. The solid infared spectra (IR) were obtained from a Bruker IFS66V vacuum-type FT–IR spectrophotometer using KBr pellets. 1-Chloromethylacetic acid benzotriazole (3.66 g, 0.02 mol) and o-phenylenediamine (2.16 g, 0.02 mol) in phosphoric acid was heated and magnetically stirred at 403 K for 2 h. After cooling to room temperature, the resulting green mixture was adjusted to pH 7–8 with 5 M NaOH. The precipitate was filtered and washed with water three times, then the collected solid was recrystallized from ethanol and colorless block-shaped crystals were obtained (yield: 3.83 g, 74.30%). Anal calculated (%) for C28H24N10O: C 65.04, H 4.68, N 27.10; found: C 65.05, H 4.64, N 27.13. IR (KBr pellet, cm-1): 3480, 3033, 2775, 1591, 1536, 1493, 1458, 1440, 1336, 1275, 1224, 1102, 1030. 955, 742. 1H NMR (d6-DMSO): 6.35 (s, 2H), 7.28 (s, 2H), 7.53 (t, 1H), 7.62 (s, 2H), 7.67 (t, 3H), 7.95 (d, 0.5H), 8.19 (d, 0.5H). |
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 | Occ. (<1) | |
O1 | −0.19173 (16) | 0.6126 (3) | 0.17340 (16) | 0.0278 (5) | 0.50 |
H1A | −0.1736 | 0.5208 | 0.2043 | 0.042* | 0.50 |
H1C | −0.2140 | 0.5889 | 0.1137 | 0.042* | 0.50 |
C1 | 0.12251 (19) | 0.6722 (3) | 0.52813 (17) | 0.0570 (6) | |
C2 | 0.0871 (3) | 0.7282 (4) | 0.6187 (2) | 0.0809 (8) | |
H2 | 0.1291 | 0.7194 | 0.6785 | 0.097* | |
C3 | −0.0060 (3) | 0.7922 (4) | 0.6147 (2) | 0.0857 (9) | |
H3 | −0.0291 | 0.8305 | 0.6734 | 0.103* | |
C4 | −0.0734 (2) | 0.8065 (4) | 0.5268 (2) | 0.0801 (8) | |
H4 | −0.1397 | 0.8510 | 0.5284 | 0.096* | |
C5 | −0.0414 (2) | 0.7549 (3) | 0.43853 (19) | 0.0601 (6) | |
H5 | −0.0838 | 0.7657 | 0.3790 | 0.072* | |
C6 | 0.05735 (16) | 0.6858 (3) | 0.44253 (14) | 0.0426 (5) | |
C7 | 0.08326 (19) | 0.6003 (3) | 0.26753 (16) | 0.0549 (6) | |
H7A | 0.0194 | 0.5351 | 0.2564 | 0.066* | |
H7B | 0.1369 | 0.5365 | 0.2390 | 0.066* | |
C8 | 0.06875 (16) | 0.7687 (3) | 0.21683 (14) | 0.0412 (5) | |
C9 | 0.09968 (15) | 1.0206 (3) | 0.15950 (14) | 0.0417 (5) | |
C10 | 0.14196 (19) | 1.1732 (3) | 0.13090 (16) | 0.0553 (6) | |
H10 | 0.2124 | 1.1963 | 0.1444 | 0.066* | |
C11 | 0.0753 (2) | 1.2890 (3) | 0.08170 (18) | 0.0615 (6) | |
H11 | 0.1020 | 1.3909 | 0.0595 | 0.074* | |
C12 | −0.0307 (2) | 1.2593 (3) | 0.06384 (18) | 0.0660 (7) | |
H12 | −0.0737 | 1.3423 | 0.0320 | 0.079* | |
C13 | −0.07297 (19) | 1.1057 (3) | 0.09327 (17) | 0.0582 (6) | |
H13 | −0.1437 | 1.0839 | 0.0814 | 0.070* | |
C14 | −0.00583 (15) | 0.9874 (3) | 0.14065 (14) | 0.0433 (5) | |
N1 | 0.11183 (14) | 0.6186 (2) | 0.37273 (12) | 0.0478 (4) | |
N2 | 0.20516 (16) | 0.5661 (3) | 0.41380 (16) | 0.0636 (6) | |
N3 | 0.21176 (17) | 0.5978 (3) | 0.50681 (16) | 0.0709 (6) | |
N4 | 0.14468 (13) | 0.8790 (2) | 0.20897 (13) | 0.0478 (4) | |
H4A | 0.2091 | 0.8656 | 0.2303 | 0.057* | 0.50 |
N5 | −0.02400 (14) | 0.8270 (2) | 0.17675 (12) | 0.0476 (4) | |
H5A | −0.0826 | 0.7747 | 0.1742 | 0.057* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0270 (13) | 0.0291 (12) | 0.0276 (11) | −0.0019 (9) | 0.0039 (9) | −0.0014 (9) |
C1 | 0.0606 (15) | 0.0553 (14) | 0.0551 (14) | −0.0015 (11) | 0.0067 (11) | 0.0016 (11) |
C2 | 0.085 (2) | 0.077 (2) | 0.080 (2) | −0.0024 (16) | 0.0073 (16) | −0.0022 (15) |
C3 | 0.090 (2) | 0.084 (2) | 0.084 (2) | 0.0009 (18) | 0.0158 (18) | 0.0027 (17) |
C4 | 0.080 (2) | 0.0788 (19) | 0.0822 (19) | −0.0005 (16) | 0.0105 (16) | 0.0027 (16) |
C5 | 0.0639 (17) | 0.0604 (14) | 0.0568 (14) | 0.0016 (11) | 0.0099 (12) | 0.0007 (12) |
C6 | 0.0437 (12) | 0.0434 (11) | 0.0411 (11) | −0.0008 (9) | 0.0060 (9) | 0.0011 (9) |
C7 | 0.0559 (14) | 0.0522 (14) | 0.0568 (13) | 0.0000 (10) | 0.0068 (11) | −0.0010 (11) |
C8 | 0.0406 (12) | 0.0417 (11) | 0.0412 (11) | −0.0011 (8) | 0.0045 (9) | 0.0005 (9) |
C9 | 0.0422 (11) | 0.0426 (11) | 0.0403 (11) | 0.0025 (9) | 0.0044 (8) | 0.0019 (9) |
C10 | 0.0556 (14) | 0.0554 (14) | 0.0552 (13) | −0.0017 (11) | 0.0078 (10) | −0.0004 (11) |
C11 | 0.0615 (16) | 0.0601 (15) | 0.0630 (14) | −0.0005 (12) | 0.0071 (12) | 0.0012 (12) |
C12 | 0.0677 (18) | 0.0656 (16) | 0.0649 (15) | −0.0024 (12) | 0.0088 (13) | −0.0005 (13) |
C13 | 0.0554 (14) | 0.0600 (15) | 0.0589 (14) | 0.0012 (11) | 0.0051 (11) | 0.0008 (11) |
C14 | 0.0448 (11) | 0.0431 (11) | 0.0421 (11) | 0.0020 (9) | 0.0053 (8) | 0.0003 (9) |
N1 | 0.0467 (10) | 0.0488 (10) | 0.0476 (10) | 0.0008 (8) | 0.0044 (8) | 0.0001 (8) |
N2 | 0.0623 (13) | 0.0630 (13) | 0.0649 (13) | 0.0003 (10) | 0.0046 (10) | 0.0024 (10) |
N3 | 0.0698 (16) | 0.0730 (15) | 0.0691 (14) | 0.0008 (11) | 0.0045 (12) | 0.0011 (11) |
N4 | 0.0474 (10) | 0.0464 (10) | 0.0495 (10) | −0.0003 (8) | 0.0054 (8) | −0.0016 (8) |
N5 | 0.0468 (10) | 0.0508 (11) | 0.0454 (9) | −0.0014 (8) | 0.0060 (8) | −0.0003 (8) |
O1—N5 | 2.741 (3) | C8—N4 | 1.321 (3) |
O1—H1A | 0.8500 | C8—N5 | 1.344 (3) |
O1—H1C | 0.8501 | C9—C10 | 1.384 (3) |
C1—N3 | 1.355 (3) | C9—N4 | 1.388 (3) |
C1—C6 | 1.364 (3) | C9—C14 | 1.389 (3) |
C1—C2 | 1.426 (4) | C10—C11 | 1.372 (3) |
C2—C3 | 1.303 (4) | C10—H10 | 0.9300 |
C2—H2 | 0.9300 | C11—C12 | 1.389 (4) |
C3—C4 | 1.404 (4) | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—C13 | 1.394 (3) |
C4—C5 | 1.370 (4) | C12—H12 | 0.9300 |
C4—H4 | 0.9300 | C13—C14 | 1.379 (3) |
C5—C6 | 1.386 (3) | C13—H13 | 0.9300 |
C5—H5 | 0.9300 | C14—N5 | 1.373 (3) |
C6—N1 | 1.349 (3) | N1—N2 | 1.340 (3) |
C7—N1 | 1.442 (3) | N2—N3 | 1.280 (3) |
C7—C8 | 1.486 (3) | N4—H4A | 0.8600 |
C7—H7A | 0.9700 | N5—H5A | 0.8600 |
C7—H7B | 0.9700 | ||
N5—O1—H1A | 109.3 | C10—C9—C14 | 121.44 (19) |
N5—O1—H1C | 109.6 | N4—C9—C14 | 107.12 (17) |
H1A—O1—H1C | 109.5 | C11—C10—C9 | 117.0 (2) |
N3—C1—C6 | 108.4 (2) | C11—C10—H10 | 121.5 |
N3—C1—C2 | 132.8 (2) | C9—C10—H10 | 121.5 |
C6—C1—C2 | 118.8 (2) | C10—C11—C12 | 122.3 (2) |
C3—C2—C1 | 117.8 (3) | C10—C11—H11 | 118.9 |
C3—C2—H2 | 121.1 | C12—C11—H11 | 118.9 |
C1—C2—H2 | 121.1 | C11—C12—C13 | 120.5 (3) |
C2—C3—C4 | 123.6 (3) | C11—C12—H12 | 119.8 |
C2—C3—H3 | 118.2 | C13—C12—H12 | 119.8 |
C4—C3—H3 | 118.2 | C14—C13—C12 | 117.4 (2) |
C5—C4—C3 | 119.9 (3) | C14—C13—H13 | 121.3 |
C5—C4—H4 | 120.0 | C12—C13—H13 | 121.3 |
C3—C4—H4 | 120.0 | N5—C14—C13 | 130.7 (2) |
C4—C5—C6 | 116.6 (2) | N5—C14—C9 | 107.97 (17) |
C4—C5—H5 | 121.7 | C13—C14—C9 | 121.4 (2) |
C6—C5—H5 | 121.7 | N2—N1—C6 | 110.24 (17) |
N1—C6—C1 | 104.13 (19) | N2—N1—C7 | 120.25 (19) |
N1—C6—C5 | 132.6 (2) | C6—N1—C7 | 129.50 (19) |
C1—C6—C5 | 123.2 (2) | N3—N2—N1 | 108.1 (2) |
N1—C7—C8 | 112.13 (17) | N2—N3—C1 | 109.1 (2) |
N1—C7—H7A | 109.2 | C8—N4—C9 | 106.23 (17) |
C8—C7—H7A | 109.2 | C8—N4—H4A | 126.9 |
N1—C7—H7B | 109.2 | C9—N4—H4A | 126.9 |
C8—C7—H7B | 109.2 | C8—N5—C14 | 105.75 (18) |
H7A—C7—H7B | 107.9 | C8—N5—O1 | 118.31 (14) |
N4—C8—N5 | 112.93 (18) | C14—N5—O1 | 135.80 (14) |
N4—C8—C7 | 123.75 (19) | C8—N5—H5A | 127.1 |
N5—C8—C7 | 123.29 (19) | C14—N5—H5A | 127.1 |
C10—C9—N4 | 131.44 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1C···N3i | 0.85 | 2.20 | 2.958 (3) | 148 |
N4—H4A···N4ii | 0.86 | 1.99 | 2.835 (3) | 169 |
N5—H5A···O1 | 0.86 | 1.90 | 2.741 (3) | 166 |
Symmetry codes: (i) x−1/2, −y+1, z−1/2; (ii) −x+1/2, y, −z+1/2. |
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