Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031757/sj6037sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031757/sj6037Isup2.hkl |
CCDC reference: 262437
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.105
- Data-to-parameter ratio = 7.0
checkCIF/PLATON results
No syntax errors found
Alert level A DIFF020_ALERT_1_A _diffrn_standards_interval_count and _diffrn_standards_interval_time are missing. Number of measurements between standards or time (min) between standards.
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.98 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C12 ... 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C3 - C11 ... 1.44 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.07 From the CIF: _reflns_number_total 1054 Count of symmetry unique reflns 1062 Completeness (_total/calc) 99.25% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2004); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
C12H6N2 | F(000) = 368 |
Mr = 178.19 | Dx = 1.355 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 6447 reflections |
a = 3.8144 (5) Å | θ = 1.7–26.1° |
b = 12.175 (2) Å | µ = 0.08 mm−1 |
c = 18.806 (3) Å | T = 153 K |
V = 873.4 (2) Å3 | Block, colourless |
Z = 4 | 0.45 × 0.25 × 0.15 mm |
Stoe IPDS-II diffractometer | 915 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.066 |
Graphite monochromator | θmax = 26.1°, θmin = 2.0° |
Detector resolution: 0.81Å pixels mm-1 | h = −4→4 |
φ or ω scans? | k = −15→15 |
6296 measured reflections | l = −23→21 |
1054 independent reflections |
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)] = 0.037 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.105 | All H-atom parameters refined |
S = 0.87 | w1/[σ2(Fo2) + (0.0678P)2] where P(Fo2 + 2Fc2)/3 |
1054 reflections | (Δ/σ)max < 0.001 |
151 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.14 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 | 0.5375 (5) | 0.36284 (13) | 0.31544 (8) | 0.0492 (5) | |
N2 | 0.2937 (5) | 0.67649 (13) | 0.33499 (9) | 0.0492 (4) | |
C1 | −0.0198 (5) | 0.62915 (14) | 0.16283 (9) | 0.0376 (4) | |
H1 | −0.093 (6) | 0.7065 (18) | 0.1693 (9) | 0.036 (5)* | |
C2 | 0.1440 (5) | 0.57532 (14) | 0.21771 (9) | 0.0363 (4) | |
C3 | 0.2388 (5) | 0.46213 (14) | 0.20996 (9) | 0.0367 (4) | |
C4 | 0.1722 (5) | 0.40828 (15) | 0.14776 (10) | 0.0387 (4) | |
H4 | 0.243 (6) | 0.3321 (17) | 0.1415 (10) | 0.039 (5)* | |
C5 | −0.0706 (6) | 0.40796 (17) | 0.02555 (10) | 0.0447 (5) | |
H5 | −0.016 (7) | 0.3286 (19) | 0.0198 (11) | 0.055 (6)* | |
C6 | −0.2324 (6) | 0.46300 (18) | −0.02889 (11) | 0.0502 (5) | |
H6 | −0.282 (8) | 0.427 (2) | −0.0739 (13) | 0.060 (7)* | |
C7 | −0.3309 (6) | 0.57365 (19) | −0.02107 (11) | 0.0485 (5) | |
H7 | −0.435 (7) | 0.610 (2) | −0.0627 (13) | 0.068 (7)* | |
C8 | −0.2647 (6) | 0.62829 (16) | 0.04127 (10) | 0.0427 (5) | |
H8 | −0.341 (6) | 0.7043 (19) | 0.0479 (10) | 0.044 (5)* | |
C9 | −0.0951 (5) | 0.57420 (14) | 0.09836 (9) | 0.0380 (4) | |
C10 | 0.0024 (5) | 0.46204 (15) | 0.09042 (9) | 0.0388 (4) | |
C11 | 0.4059 (5) | 0.40701 (14) | 0.26844 (10) | 0.0390 (4) | |
C12 | 0.2243 (6) | 0.63200 (14) | 0.28299 (9) | 0.0401 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0576 (11) | 0.0388 (8) | 0.0512 (9) | 0.0007 (8) | −0.0056 (9) | 0.0027 (7) |
N2 | 0.0583 (11) | 0.0386 (8) | 0.0509 (9) | 0.0008 (8) | −0.0035 (9) | −0.0034 (7) |
C1 | 0.0365 (9) | 0.0295 (7) | 0.0469 (9) | −0.0003 (8) | 0.0038 (9) | 0.0020 (6) |
C2 | 0.0354 (9) | 0.0325 (8) | 0.0410 (9) | −0.0035 (7) | 0.0043 (7) | 0.0004 (7) |
C3 | 0.0355 (9) | 0.0320 (8) | 0.0427 (9) | −0.0008 (8) | 0.0017 (8) | 0.0034 (6) |
C4 | 0.0390 (10) | 0.0298 (8) | 0.0473 (10) | −0.0018 (8) | 0.0038 (8) | 0.0005 (7) |
C5 | 0.0439 (10) | 0.0427 (9) | 0.0476 (10) | −0.0005 (9) | 0.0018 (9) | −0.0057 (8) |
C6 | 0.0446 (11) | 0.0631 (13) | 0.0428 (10) | −0.0019 (11) | −0.0001 (9) | −0.0046 (8) |
C7 | 0.0427 (11) | 0.0590 (12) | 0.0438 (10) | 0.0005 (10) | 0.0028 (9) | 0.0064 (9) |
C8 | 0.0394 (11) | 0.0430 (10) | 0.0458 (10) | 0.0012 (9) | 0.0022 (9) | 0.0074 (8) |
C9 | 0.0357 (9) | 0.0355 (9) | 0.0429 (9) | −0.0010 (8) | 0.0047 (8) | 0.0031 (7) |
C10 | 0.0365 (10) | 0.0368 (9) | 0.0431 (9) | −0.0023 (9) | 0.0040 (8) | −0.0002 (7) |
C11 | 0.0401 (10) | 0.0307 (7) | 0.0463 (9) | −0.0026 (8) | 0.0003 (9) | 0.0011 (7) |
C12 | 0.0422 (11) | 0.0320 (8) | 0.0460 (10) | 0.0004 (8) | 0.0011 (9) | 0.0006 (7) |
N1—C11 | 1.150 (2) | C5—C6 | 1.371 (3) |
N2—C12 | 1.149 (2) | C5—C10 | 1.414 (3) |
C1—C2 | 1.373 (3) | C5—H5 | 1.00 (2) |
C1—C9 | 1.414 (2) | C6—C7 | 1.406 (3) |
C1—H1 | 0.99 (2) | C6—H6 | 0.97 (2) |
C2—C3 | 1.432 (2) | C7—C8 | 1.371 (3) |
C2—C12 | 1.441 (2) | C7—H7 | 0.98 (3) |
C3—C4 | 1.365 (3) | C8—C9 | 1.416 (3) |
C3—C11 | 1.437 (3) | C8—H8 | 0.98 (2) |
C4—C10 | 1.418 (3) | C9—C10 | 1.423 (2) |
C4—H4 | 0.97 (2) | ||
C2—C1—C9 | 120.74 (15) | C5—C6—H6 | 121.1 (15) |
C2—C1—H1 | 119.4 (11) | C7—C6—H6 | 118.2 (15) |
C9—C1—H1 | 119.9 (11) | C8—C7—C6 | 120.3 (2) |
C1—C2—C3 | 119.85 (16) | C8—C7—H7 | 122.6 (15) |
C1—C2—C12 | 120.56 (15) | C6—C7—H7 | 117.0 (15) |
C3—C2—C12 | 119.58 (17) | C7—C8—C9 | 120.45 (18) |
C4—C3—C2 | 120.16 (16) | C7—C8—H8 | 120.9 (12) |
C4—C3—C11 | 120.93 (15) | C9—C8—H8 | 118.6 (12) |
C2—C3—C11 | 118.91 (16) | C8—C9—C1 | 121.52 (16) |
C3—C4—C10 | 120.99 (15) | C8—C9—C10 | 119.09 (17) |
C3—C4—H4 | 120.6 (12) | C1—C9—C10 | 119.39 (16) |
C10—C4—H4 | 118.4 (12) | C5—C10—C4 | 122.08 (16) |
C6—C5—C10 | 120.37 (18) | C5—C10—C9 | 119.07 (17) |
C6—C5—H5 | 119.2 (12) | C4—C10—C9 | 118.85 (16) |
C10—C5—H5 | 120.3 (12) | N1—C11—C3 | 179.5 (2) |
C5—C6—C7 | 120.70 (19) | N2—C12—C2 | 178.9 (2) |
C9—C1—C2—C3 | −0.3 (3) | C7—C8—C9—C10 | −0.6 (3) |
C9—C1—C2—C12 | 179.22 (17) | C2—C1—C9—C8 | 179.82 (18) |
C1—C2—C3—C4 | 1.2 (3) | C2—C1—C9—C10 | −0.4 (3) |
C12—C2—C3—C4 | −178.34 (18) | C6—C5—C10—C4 | −179.41 (18) |
C1—C2—C3—C11 | −179.20 (18) | C6—C5—C10—C9 | 0.1 (3) |
C12—C2—C3—C11 | 1.3 (3) | C3—C4—C10—C5 | −179.76 (18) |
C2—C3—C4—C10 | −1.4 (3) | C3—C4—C10—C9 | 0.7 (3) |
C11—C3—C4—C10 | 179.00 (17) | C8—C9—C10—C5 | 0.4 (3) |
C10—C5—C6—C7 | −0.5 (3) | C1—C9—C10—C5 | −179.37 (18) |
C5—C6—C7—C8 | 0.3 (3) | C8—C9—C10—C4 | 179.98 (18) |
C6—C7—C8—C9 | 0.3 (3) | C1—C9—C10—C4 | 0.2 (3) |
C7—C8—C9—C1 | 179.15 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···N1i | 0.99 (2) | 2.57 (2) | 3.487 (2) | 154.7 (16) |
C4—H4···N2ii | 0.97 (2) | 2.63 (2) | 3.496 (3) | 148.6 (16) |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2. |