Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805031260/jh6020sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805031260/jh6020Isup2.hkl |
CCDC reference: 289788
Key indicators
- Single-crystal X-ray study
- T = 288 K
- Mean (C-C) = 0.003 Å
- R factor = 0.052
- wR factor = 0.124
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C11 - C16 .. 5.18 su PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C9 - C14 ... 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C11 - C16 ... 1.43 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C12 - C15 ... 1.44 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H1 .. N2 .. 2.73 Ang.
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 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
C16H9N3 | F(000) = 504 |
Mr = 243.26 | Dx = 1.272 Mg m−3 |
Monoclinic, P21/c | Melting point: 421.2 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 11.289 (2) Å | Cell parameters from 25 reflections |
b = 8.6380 (17) Å | θ = 10–13° |
c = 14.193 (3) Å | µ = 0.08 mm−1 |
β = 113.42 (3)° | T = 288 K |
V = 1270.0 (4) Å3 | Block, colourless |
Z = 4 | 0.40 × 0.33 × 0.30 mm |
Enraf–Nonius CAD-4 diffractometer | 1560 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 26.0°, θmin = 2.0° |
ω/2θ scans | h = 0→13 |
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995) | k = 0→10 |
Tmin = 0.954, Tmax = 0.977 | l = −16→16 |
2622 measured reflections | 3 standard reflections every 200 reflections |
2493 independent reflections | intensity decay: none |
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) = 0.124 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0301P)2 + 0.8P] where P = (Fo2 + 2Fc2)/3 |
2493 reflections | (Δ/σ)max = 0.006 |
174 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.25 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 | ||
N1 | 0.5853 (2) | 0.8025 (3) | 0.02270 (18) | 0.0766 (7) | |
N2 | 0.9076 (2) | 1.1853 (3) | 0.57250 (17) | 0.0727 (7) | |
N3 | 1.0586 (2) | 1.2572 (3) | 0.36706 (18) | 0.0682 (6) | |
C1 | 0.1781 (2) | 1.0524 (3) | 0.1829 (3) | 0.0692 (8) | |
H1 | 0.1038 | 1.1111 | 0.1683 | 0.083* | |
C2 | 0.2198 (2) | 1.0170 (3) | 0.1066 (2) | 0.0662 (8) | |
H2 | 0.1732 | 1.0514 | 0.0399 | 0.079* | |
C3 | 0.3306 (2) | 0.9307 (3) | 0.12879 (18) | 0.0514 (6) | |
H3 | 0.3578 | 0.9070 | 0.0766 | 0.062* | |
C4 | 0.4014 (2) | 0.8791 (2) | 0.22713 (17) | 0.0387 (5) | |
C5 | 0.3574 (2) | 0.9142 (3) | 0.30277 (19) | 0.0504 (6) | |
H5 | 0.4030 | 0.8792 | 0.3695 | 0.060* | |
C6 | 0.2471 (2) | 1.0001 (3) | 0.2806 (2) | 0.0641 (7) | |
H6 | 0.2191 | 1.0231 | 0.3324 | 0.077* | |
C7 | 0.5250 (2) | 0.7900 (2) | 0.25312 (18) | 0.0438 (5) | |
H7A | 0.5164 | 0.7223 | 0.1963 | 0.053* | |
H7B | 0.5399 | 0.7258 | 0.3128 | 0.053* | |
C8 | 0.63948 (19) | 0.8949 (2) | 0.27495 (16) | 0.0380 (5) | |
C9 | 0.6903 (2) | 0.9284 (2) | 0.20166 (16) | 0.0414 (5) | |
C10 | 0.7962 (2) | 1.0245 (2) | 0.22337 (17) | 0.0446 (5) | |
H10 | 0.8280 | 1.0441 | 0.1733 | 0.053* | |
C11 | 0.85451 (19) | 1.0912 (2) | 0.31953 (17) | 0.0397 (5) | |
C12 | 0.8041 (2) | 1.0601 (2) | 0.39365 (16) | 0.0398 (5) | |
C13 | 0.6992 (2) | 0.9629 (2) | 0.37092 (16) | 0.0411 (5) | |
H13 | 0.6679 | 0.9425 | 0.4211 | 0.049* | |
C14 | 0.6327 (2) | 0.8583 (3) | 0.10160 (19) | 0.0523 (6) | |
C15 | 0.8625 (2) | 1.1302 (3) | 0.49359 (18) | 0.0486 (6) | |
C16 | 0.9668 (2) | 1.1868 (3) | 0.34467 (18) | 0.0489 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0936 (18) | 0.0821 (18) | 0.0559 (14) | −0.0190 (14) | 0.0318 (13) | −0.0210 (13) |
N2 | 0.0886 (17) | 0.0746 (16) | 0.0452 (13) | −0.0194 (14) | 0.0163 (12) | −0.0059 (12) |
N3 | 0.0593 (14) | 0.0664 (15) | 0.0825 (16) | −0.0152 (12) | 0.0320 (12) | −0.0097 (13) |
C1 | 0.0471 (15) | 0.0470 (15) | 0.113 (3) | 0.0033 (12) | 0.0308 (16) | 0.0089 (17) |
C2 | 0.0537 (15) | 0.0567 (16) | 0.0691 (18) | −0.0015 (13) | 0.0042 (14) | 0.0188 (14) |
C3 | 0.0553 (14) | 0.0455 (14) | 0.0486 (14) | −0.0060 (12) | 0.0156 (11) | 0.0021 (11) |
C4 | 0.0449 (12) | 0.0232 (10) | 0.0483 (13) | −0.0073 (9) | 0.0187 (10) | −0.0002 (9) |
C5 | 0.0563 (14) | 0.0425 (13) | 0.0559 (15) | −0.0033 (11) | 0.0261 (12) | 0.0046 (11) |
C6 | 0.0626 (16) | 0.0558 (16) | 0.086 (2) | 0.0009 (14) | 0.0426 (16) | −0.0002 (15) |
C7 | 0.0533 (14) | 0.0271 (10) | 0.0512 (13) | −0.0033 (10) | 0.0209 (11) | 0.0002 (10) |
C8 | 0.0409 (11) | 0.0265 (10) | 0.0454 (12) | 0.0066 (9) | 0.0160 (10) | 0.0022 (9) |
C9 | 0.0486 (12) | 0.0347 (11) | 0.0415 (12) | 0.0053 (10) | 0.0186 (10) | −0.0031 (10) |
C10 | 0.0519 (13) | 0.0410 (13) | 0.0484 (13) | 0.0026 (11) | 0.0280 (11) | 0.0005 (10) |
C11 | 0.0384 (11) | 0.0313 (11) | 0.0498 (13) | 0.0031 (9) | 0.0179 (10) | 0.0011 (10) |
C12 | 0.0416 (12) | 0.0339 (11) | 0.0407 (12) | 0.0054 (9) | 0.0131 (9) | 0.0028 (9) |
C13 | 0.0464 (12) | 0.0365 (12) | 0.0424 (13) | 0.0025 (10) | 0.0197 (10) | 0.0038 (10) |
C14 | 0.0619 (15) | 0.0476 (14) | 0.0520 (15) | −0.0044 (12) | 0.0274 (13) | −0.0053 (12) |
C15 | 0.0521 (14) | 0.0457 (13) | 0.0428 (13) | −0.0026 (11) | 0.0135 (11) | 0.0039 (11) |
C16 | 0.0462 (13) | 0.0471 (13) | 0.0563 (15) | 0.0021 (11) | 0.0235 (12) | −0.0017 (12) |
N1—C14 | 1.138 (3) | C7—C8 | 1.506 (3) |
N2—C15 | 1.135 (3) | C7—H7A | 0.9700 |
N3—C16 | 1.133 (3) | C7—H7B | 0.9700 |
C1—C6 | 1.369 (4) | C8—C13 | 1.387 (3) |
C1—C2 | 1.376 (4) | C8—C9 | 1.403 (3) |
C1—H1 | 0.9300 | C9—C10 | 1.385 (3) |
C2—C3 | 1.381 (3) | C9—C14 | 1.440 (3) |
C2—H2 | 0.9300 | C10—C11 | 1.384 (3) |
C3—C4 | 1.378 (3) | C10—H10 | 0.9300 |
C3—H3 | 0.9300 | C11—C12 | 1.407 (3) |
C4—C5 | 1.384 (3) | C11—C16 | 1.434 (3) |
C4—C7 | 1.505 (3) | C12—C13 | 1.381 (3) |
C5—C6 | 1.374 (3) | C12—C15 | 1.439 (3) |
C5—H5 | 0.9300 | C13—H13 | 0.9300 |
C6—H6 | 0.9300 | ||
C6—C1—C2 | 119.3 (3) | H7A—C7—H7B | 107.9 |
C6—C1—H1 | 120.4 | C13—C8—C9 | 117.26 (19) |
C2—C1—H1 | 120.4 | C13—C8—C7 | 119.9 (2) |
C1—C2—C3 | 120.2 (3) | C9—C8—C7 | 122.80 (19) |
C1—C2—H2 | 119.9 | C10—C9—C8 | 122.0 (2) |
C3—C2—H2 | 119.9 | C10—C9—C14 | 118.9 (2) |
C4—C3—C2 | 121.0 (2) | C8—C9—C14 | 119.2 (2) |
C4—C3—H3 | 119.5 | C11—C10—C9 | 120.0 (2) |
C2—C3—H3 | 119.5 | C11—C10—H10 | 120.0 |
C3—C4—C5 | 118.2 (2) | C9—C10—H10 | 120.0 |
C3—C4—C7 | 121.5 (2) | C10—C11—C12 | 118.8 (2) |
C5—C4—C7 | 120.4 (2) | C10—C11—C16 | 120.8 (2) |
C6—C5—C4 | 120.8 (2) | C12—C11—C16 | 120.3 (2) |
C6—C5—H5 | 119.6 | C13—C12—C11 | 120.4 (2) |
C4—C5—H5 | 119.6 | C13—C12—C15 | 120.0 (2) |
C1—C6—C5 | 120.6 (3) | C11—C12—C15 | 119.6 (2) |
C1—C6—H6 | 119.7 | C12—C13—C8 | 121.6 (2) |
C5—C6—H6 | 119.7 | C12—C13—H13 | 119.2 |
C4—C7—C8 | 112.26 (17) | C8—C13—H13 | 119.2 |
C4—C7—H7A | 109.2 | N1—C14—C9 | 178.8 (3) |
C8—C7—H7A | 109.2 | N2—C15—C12 | 179.4 (3) |
C4—C7—H7B | 109.2 | N3—C16—C11 | 177.0 (3) |
C8—C7—H7B | 109.2 | ||
C6—C1—C2—C3 | −0.4 (4) | C13—C8—C9—C14 | 178.92 (19) |
C1—C2—C3—C4 | −0.3 (4) | C7—C8—C9—C14 | −1.0 (3) |
C2—C3—C4—C5 | 0.9 (3) | C8—C9—C10—C11 | −0.4 (3) |
C2—C3—C4—C7 | −177.7 (2) | C14—C9—C10—C11 | −178.9 (2) |
C3—C4—C5—C6 | −1.0 (3) | C9—C10—C11—C12 | −0.2 (3) |
C7—C4—C5—C6 | 177.7 (2) | C9—C10—C11—C16 | 177.9 (2) |
C2—C1—C6—C5 | 0.4 (4) | C10—C11—C12—C13 | 0.8 (3) |
C4—C5—C6—C1 | 0.3 (4) | C16—C11—C12—C13 | −177.3 (2) |
C3—C4—C7—C8 | 84.3 (3) | C10—C11—C12—C15 | −179.2 (2) |
C5—C4—C7—C8 | −94.3 (2) | C16—C11—C12—C15 | 2.7 (3) |
C4—C7—C8—C13 | 81.2 (2) | C11—C12—C13—C8 | −0.8 (3) |
C4—C7—C8—C9 | −98.9 (2) | C15—C12—C13—C8 | 179.2 (2) |
C13—C8—C9—C10 | 0.4 (3) | C9—C8—C13—C12 | 0.2 (3) |
C7—C8—C9—C10 | −179.6 (2) | C7—C8—C13—C12 | −179.79 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···N2i | 0.93 | 2.73 | 3.621 (3) | 161 |
Symmetry code: (i) x−1, −y+5/2, z−1/2. |
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