Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803026977/na6273sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803026977/na6273Isup2.hkl |
CCDC reference: 227921
Key indicators
- Single-crystal X-ray study
- T = 223 K
- R factor = 0.042
- wR factor = 0.096
- Data-to-parameter ratio = 13.9
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 37 Perc.
Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.725 RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.132 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.13 PLAT480_ALERT_4_C Long H...A H-Bond Reported H12 .. C1G = 2.81 Ang. PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... C1G H12 C1G PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... C1G C12 C1G PLAT718_ALERT_1_C D-H..A Unknown or Inconsistent Label .......... C1G C12 H12 C1G
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 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 1 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: EXPOSE (Stoe, 2000); cell refinement: CELL (Stoe, 2000); data reduction: INTEGRATE (Stoe, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON99 (Spek, 1990); software used to prepare material for publication: SHELXL97.
C36H22N8 | F(000) = 588 |
Mr = 566.62 | Dx = 1.325 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2327 reflections |
a = 6.8892 (6) Å | θ = 2.3–25.9° |
b = 7.7255 (6) Å | µ = 0.08 mm−1 |
c = 26.895 (2) Å | T = 223 K |
β = 97.024 (11)° | Plate, orange |
V = 1420.7 (2) Å3 | 0.35 × 0.30 × 0.10 mm |
Z = 2 |
STOE IPDS diffractometer | 1024 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.133 |
Graphite monochromator | θmax = 25.9°, θmin = 2.7° |
Detector resolution: 0.81Å pixels mm-1 | h = −8→8 |
φ oscillation scans | k = −9→9 |
10763 measured reflections | l = −32→33 |
2771 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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.096 | H-atom parameters constrained |
S = 0.73 | w = 1/[σ2(Fo2) + (0.0319P)2] where P = (Fo2 + 2Fc2)/3 |
2771 reflections | (Δ/σ)max < 0.001 |
199 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.16 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 | ||
C1 | 0.0978 (3) | 0.4588 (3) | 0.00588 (9) | 0.0391 (6) | |
C2 | 0.2028 (3) | 0.4709 (3) | 0.05264 (9) | 0.0419 (7) | |
H2 | 0.1514 | 0.5353 | 0.0777 | 0.050* | |
C3 | 0.3844 (3) | 0.3894 (3) | 0.06381 (8) | 0.0386 (6) | |
C4 | 0.6583 (4) | 0.3353 (4) | 0.11898 (8) | 0.0437 (7) | |
C5 | 0.7861 (4) | 0.3882 (4) | 0.16548 (9) | 0.0482 (7) | |
C6 | 0.7130 (4) | 0.4224 (4) | 0.20948 (10) | 0.0667 (9) | |
H6 | 0.5787 | 0.4097 | 0.2118 | 0.080* | |
C7 | 0.8399 (5) | 0.4762 (5) | 0.25066 (11) | 0.0813 (11) | |
H7 | 0.7941 | 0.4984 | 0.2816 | 0.098* | |
C8 | 1.0331 (6) | 0.4958 (5) | 0.24508 (12) | 0.0829 (11) | |
H8 | 1.1232 | 0.5319 | 0.2722 | 0.099* | |
C9 | 1.0935 (5) | 0.4622 (5) | 0.19948 (12) | 0.0761 (10) | |
H9 | 1.2265 | 0.4773 | 0.1960 | 0.091* | |
C10 | 0.7227 (4) | 0.2137 (4) | 0.08426 (9) | 0.0428 (7) | |
C11 | 0.8921 (4) | 0.0958 (4) | 0.09789 (9) | 0.0451 (7) | |
C12 | 1.0261 (4) | 0.0629 (4) | 0.06535 (9) | 0.0484 (7) | |
H12 | 1.0125 | 0.1143 | 0.0334 | 0.058* | |
C13 | 1.1805 (4) | −0.0458 (4) | 0.07982 (12) | 0.0623 (9) | |
H13 | 1.2764 | −0.0671 | 0.0585 | 0.075* | |
C14 | 1.1914 (5) | −0.1225 (4) | 0.12600 (12) | 0.0708 (10) | |
H14 | 1.2953 | −0.1972 | 0.1373 | 0.085* | |
C15 | 1.0480 (5) | −0.0878 (5) | 0.15514 (11) | 0.0752 (10) | |
H15 | 1.0547 | −0.1441 | 0.1863 | 0.090* | |
C16 | 0.4602 (4) | 0.2882 (3) | 0.02761 (9) | 0.0389 (6) | |
C17 | 0.3557 (4) | 0.2787 (4) | −0.02080 (9) | 0.0460 (7) | |
H17 | 0.4061 | 0.2145 | −0.0460 | 0.055* | |
C18 | 0.1821 (4) | 0.3625 (4) | −0.03095 (9) | 0.0442 (7) | |
H18 | 0.1154 | 0.3564 | −0.0636 | 0.053* | |
N1 | 0.4891 (3) | 0.4161 (3) | 0.11010 (7) | 0.0460 (6) | |
N2 | 0.6291 (3) | 0.1949 (3) | 0.03847 (7) | 0.0450 (6) | |
N3 | 0.9736 (3) | 0.4090 (3) | 0.15973 (8) | 0.0611 (7) | |
N4 | 0.8983 (3) | 0.0200 (3) | 0.14284 (8) | 0.0639 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0349 (14) | 0.0432 (17) | 0.0390 (14) | 0.0000 (13) | 0.0040 (11) | 0.0013 (12) |
C2 | 0.0390 (15) | 0.0474 (19) | 0.0396 (14) | 0.0056 (14) | 0.0065 (12) | −0.0041 (13) |
C3 | 0.0355 (15) | 0.0437 (17) | 0.0364 (13) | 0.0001 (14) | 0.0029 (11) | 0.0000 (13) |
C4 | 0.0386 (16) | 0.0561 (19) | 0.0368 (13) | 0.0059 (15) | 0.0063 (12) | −0.0002 (13) |
C5 | 0.0412 (16) | 0.060 (2) | 0.0423 (15) | 0.0094 (15) | 0.0008 (12) | 0.0025 (14) |
C6 | 0.0536 (18) | 0.098 (3) | 0.0498 (17) | 0.0084 (19) | 0.0107 (15) | −0.0113 (17) |
C7 | 0.083 (2) | 0.113 (3) | 0.0485 (18) | 0.008 (2) | 0.0073 (18) | −0.0163 (19) |
C8 | 0.080 (3) | 0.104 (3) | 0.057 (2) | 0.009 (2) | −0.0206 (19) | −0.010 (2) |
C9 | 0.0503 (18) | 0.102 (3) | 0.073 (2) | 0.004 (2) | −0.0071 (17) | −0.011 (2) |
C10 | 0.0373 (15) | 0.0475 (18) | 0.0446 (15) | 0.0026 (14) | 0.0090 (13) | 0.0036 (14) |
C11 | 0.0411 (15) | 0.0487 (19) | 0.0444 (15) | 0.0046 (15) | 0.0009 (13) | 0.0000 (14) |
C12 | 0.0455 (16) | 0.048 (2) | 0.0523 (15) | 0.0043 (16) | 0.0092 (13) | −0.0016 (14) |
C13 | 0.0504 (19) | 0.058 (2) | 0.080 (2) | 0.0107 (18) | 0.0140 (16) | −0.0104 (18) |
C14 | 0.064 (2) | 0.068 (2) | 0.076 (2) | 0.0267 (19) | −0.0114 (19) | −0.0063 (19) |
C15 | 0.090 (3) | 0.081 (3) | 0.0525 (18) | 0.030 (2) | 0.0016 (18) | 0.0119 (18) |
C16 | 0.0350 (15) | 0.0418 (17) | 0.0403 (14) | 0.0025 (14) | 0.0058 (12) | −0.0015 (13) |
C17 | 0.0407 (17) | 0.056 (2) | 0.0403 (15) | 0.0053 (15) | 0.0024 (13) | −0.0072 (13) |
C18 | 0.0364 (15) | 0.056 (2) | 0.0394 (14) | 0.0011 (15) | 0.0021 (12) | −0.0058 (14) |
N1 | 0.0386 (13) | 0.0571 (17) | 0.0421 (12) | 0.0076 (12) | 0.0038 (10) | −0.0030 (11) |
N2 | 0.0419 (14) | 0.0500 (16) | 0.0425 (12) | 0.0044 (12) | 0.0027 (10) | −0.0035 (11) |
N3 | 0.0442 (14) | 0.086 (2) | 0.0521 (14) | 0.0009 (15) | 0.0017 (11) | −0.0083 (14) |
N4 | 0.0683 (17) | 0.0724 (19) | 0.0514 (14) | 0.0244 (16) | 0.0084 (12) | 0.0103 (13) |
C1—C2 | 1.375 (3) | C9—H9 | 0.9400 |
C1—C18 | 1.419 (3) | C10—N2 | 1.326 (3) |
C1—C1i | 1.488 (5) | C10—C11 | 1.491 (3) |
C2—C3 | 1.400 (3) | C11—N4 | 1.339 (3) |
C2—H2 | 0.9400 | C11—C12 | 1.371 (3) |
C3—N1 | 1.376 (3) | C12—C13 | 1.374 (4) |
C3—C16 | 1.399 (3) | C12—H12 | 0.9400 |
C4—N1 | 1.318 (3) | C13—C14 | 1.370 (4) |
C4—C10 | 1.432 (3) | C13—H13 | 0.9400 |
C4—C5 | 1.496 (3) | C14—C15 | 1.361 (4) |
C5—N3 | 1.330 (3) | C14—H14 | 0.9400 |
C5—C6 | 1.367 (4) | C15—N4 | 1.335 (4) |
C6—C7 | 1.388 (4) | C15—H15 | 0.9400 |
C6—H6 | 0.9400 | C16—N2 | 1.370 (3) |
C7—C8 | 1.366 (4) | C16—C17 | 1.410 (3) |
C7—H7 | 0.9400 | C17—C18 | 1.358 (3) |
C8—C9 | 1.367 (4) | C17—H17 | 0.9400 |
C8—H8 | 0.9400 | C18—H18 | 0.9400 |
C9—N3 | 1.333 (3) | ||
C2—C1—C18 | 117.3 (2) | C4—C10—C11 | 122.4 (2) |
C2—C1—C1i | 121.8 (3) | N4—C11—C12 | 123.1 (2) |
C18—C1—C1i | 120.9 (3) | N4—C11—C10 | 115.3 (2) |
C1—C2—C3 | 121.5 (2) | C12—C11—C10 | 121.6 (2) |
C1—C2—H2 | 119.3 | C11—C12—C13 | 119.4 (3) |
C3—C2—H2 | 119.3 | C11—C12—H12 | 120.3 |
N1—C3—C16 | 121.0 (2) | C13—C12—H12 | 120.3 |
N1—C3—C2 | 118.9 (2) | C14—C13—C12 | 118.5 (3) |
C16—C3—C2 | 120.1 (2) | C14—C13—H13 | 120.8 |
N1—C4—C10 | 122.0 (2) | C12—C13—H13 | 120.8 |
N1—C4—C5 | 116.0 (2) | C15—C14—C13 | 118.3 (3) |
C10—C4—C5 | 121.8 (2) | C15—C14—H14 | 120.9 |
N3—C5—C6 | 122.9 (2) | C13—C14—H14 | 120.9 |
N3—C5—C4 | 114.6 (2) | N4—C15—C14 | 125.0 (3) |
C6—C5—C4 | 122.3 (2) | N4—C15—H15 | 117.5 |
C5—C6—C7 | 119.1 (3) | C14—C15—H15 | 117.5 |
C5—C6—H6 | 120.5 | N2—C16—C3 | 121.7 (2) |
C7—C6—H6 | 120.5 | N2—C16—C17 | 119.6 (2) |
C8—C7—C6 | 118.2 (3) | C3—C16—C17 | 118.7 (2) |
C8—C7—H7 | 120.9 | C18—C17—C16 | 119.9 (3) |
C6—C7—H7 | 120.9 | C18—C17—H17 | 120.1 |
C7—C8—C9 | 119.0 (3) | C16—C17—H17 | 120.1 |
C7—C8—H8 | 120.5 | C17—C18—C1 | 122.4 (2) |
C9—C8—H8 | 120.5 | C17—C18—H18 | 118.8 |
N3—C9—C8 | 123.4 (3) | C1—C18—H18 | 118.8 |
N3—C9—H9 | 118.3 | C4—N1—C3 | 116.6 (2) |
C8—C9—H9 | 118.3 | C10—N2—C16 | 116.4 (2) |
N2—C10—C4 | 121.5 (2) | C5—N3—C9 | 117.3 (2) |
N2—C10—C11 | 116.0 (2) | C15—N4—C11 | 115.8 (2) |
C18—C1—C2—C3 | −0.9 (4) | C13—C14—C15—N4 | −2.0 (5) |
C1i—C1—C2—C3 | 178.3 (3) | N1—C3—C16—N2 | 8.0 (4) |
C1—C2—C3—N1 | 175.4 (2) | C2—C3—C16—N2 | −174.4 (2) |
C1—C2—C3—C16 | −2.2 (4) | N1—C3—C16—C17 | −173.9 (3) |
N1—C4—C5—N3 | −136.2 (3) | C2—C3—C16—C17 | 3.7 (4) |
C10—C4—C5—N3 | 39.1 (4) | N2—C16—C17—C18 | 176.0 (2) |
N1—C4—C5—C6 | 40.1 (4) | C3—C16—C17—C18 | −2.1 (4) |
C10—C4—C5—C6 | −144.6 (3) | C16—C17—C18—C1 | −1.0 (4) |
N3—C5—C6—C7 | −2.0 (5) | C2—C1—C18—C17 | 2.6 (4) |
C4—C5—C6—C7 | −178.0 (3) | C1i—C1—C18—C17 | −176.7 (3) |
C5—C6—C7—C8 | 1.2 (5) | C10—C4—N1—C3 | −5.4 (4) |
C6—C7—C8—C9 | 0.0 (6) | C5—C4—N1—C3 | 169.9 (2) |
C7—C8—C9—N3 | −0.7 (6) | C16—C3—N1—C4 | −3.1 (4) |
N1—C4—C10—N2 | 9.8 (4) | C2—C3—N1—C4 | 179.4 (2) |
C5—C4—C10—N2 | −165.2 (2) | C4—C10—N2—C16 | −4.7 (4) |
N1—C4—C10—C11 | −167.3 (3) | C11—C10—N2—C16 | 172.6 (2) |
C5—C4—C10—C11 | 17.7 (4) | C3—C16—N2—C10 | −3.8 (4) |
N2—C10—C11—N4 | −133.7 (3) | C17—C16—N2—C10 | 178.1 (3) |
C4—C10—C11—N4 | 43.6 (4) | C6—C5—N3—C9 | 1.4 (5) |
N2—C10—C11—C12 | 43.7 (4) | C4—C5—N3—C9 | 177.7 (3) |
C4—C10—C11—C12 | −139.0 (3) | C8—C9—N3—C5 | 0.0 (5) |
N4—C11—C12—C13 | −3.3 (4) | C14—C15—N4—C11 | 0.9 (5) |
C10—C11—C12—C13 | 179.5 (3) | C12—C11—N4—C15 | 1.8 (4) |
C11—C12—C13—C14 | 2.1 (4) | C10—C11—N4—C15 | 179.1 (3) |
C12—C13—C14—C15 | 0.4 (5) |
Symmetry code: (i) −x, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···N4ii | 0.94 | 2.56 | 3.487 (4) | 167 |
C12—H12···C1giii | 0.94 | 2.81 | 3.343 (3) | 117 |
Symmetry codes: (ii) −x+3/2, y+1/2, −z+1/2; (iii) x+1, y, z. |
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