Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804001254/ob6346sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804001254/ob6346Isup2.hkl |
CCDC reference: 234905
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.054
- wR factor = 0.142
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
Data collection: SMART-W2K/NT (Bruker, 2003); cell refinement: SMART-W2K/NT; data reduction: SAINT-W2K/NT (Bruker, 2003); program(s) used to solve structure: SHELXTL-NT (Bruker, 2003); program(s) used to refine structure: SHELXTL-NT; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL-NT.
C26H28N6 | Z = 1 |
Mr = 424.54 | F(000) = 226 |
Triclinic, P1 | Dx = 1.179 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.228 (1) Å | Cell parameters from 954 reflections |
b = 9.482 (2) Å | θ = 2.7–22.9° |
c = 10.760 (2) Å | µ = 0.07 mm−1 |
α = 77.66 (3)° | T = 298 K |
β = 87.74 (3)° | Prism, colourless |
γ = 74.47 (3)° | 0.48 × 0.45 × 0.35 mm |
V = 598.0 (2) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 2824 independent reflections |
Radiation source: fine-focus sealed tube | 1800 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
Detector resolution: 8.366 pixels mm-1 | θmax = 27.9°, θmin = 1.9° |
φ and ω scans | h = −8→8 |
Absorption correction: empirical (using intensity measurements) (SADABS; Scheldrick, 1996) | k = −12→10 |
Tmin = 0.966, Tmax = 0.977 | l = −14→13 |
4392 measured 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)] = 0.054 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.142 | Only H-atom coordinates refined |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0689P)2 + 0.0224P] where P = (Fo2 + 2Fc2)/3 |
2824 reflections | (Δ/σ)max < 0.001 |
187 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.12 e Å−3 |
Experimental. ? #Insert any special details here. |
Geometry. Mean-plane data from final SHELXL refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 0.5024 (0.0057) x - 3.2819 (0.0072) y + 8.8452 (0.0066) z = 2.9039 (0.0028) * 0.0023 (0.0011) C3 * -0.0006 (0.0008) C4 * -0.0013 (0.0009) C6 * 0.0032 (0.0012) C7 * -0.0037 (0.0010) N2 Rms deviation of fitted atoms = 0.0025 0.9886 (0.0045) x + 6.3156 (0.0066) y + 9.3717 (0.0065) z = 5.0488 (0.0044) Angle to previous plane (with approximate e.s.d.) = 63.11 (0.06) * -0.0044 (0.0011) C9 * 0.0025 (0.0012) C10 * 0.0023 (0.0013) C11 * -0.0053 (0.0013) C12 * 0.0036 (0.0013) C13 * 0.0013 (0.0011) N3 Rms deviation of fitted atoms = 0.0035 |
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 | 0.0300 (2) | 0.39675 (13) | 0.36619 (12) | 0.0538 (4) | |
N2 | 0.0892 (2) | 0.02657 (14) | 0.33271 (13) | 0.0577 (4) | |
N3 | −0.1486 (2) | 0.68340 (15) | 0.09403 (13) | 0.0643 (4) | |
C1 | −0.0729 (3) | 0.50526 (19) | 0.44404 (17) | 0.0588 (4) | |
C2 | 0.0152 (3) | 0.24517 (17) | 0.42498 (18) | 0.0599 (4) | |
C3 | 0.1732 (3) | 0.12822 (16) | 0.36635 (14) | 0.0510 (4) | |
C4 | 0.3953 (3) | 0.1250 (2) | 0.35211 (18) | 0.0678 (5) | |
C5 | 0.5366 (3) | 0.0118 (2) | 0.30220 (19) | 0.0778 (6) | |
C6 | 0.4514 (4) | −0.0928 (2) | 0.26823 (19) | 0.0753 (6) | |
C7 | 0.2295 (4) | −0.0819 (2) | 0.28548 (18) | 0.0690 (5) | |
C8 | −0.0708 (3) | 0.4430 (2) | 0.23878 (16) | 0.0605 (5) | |
C9 | 0.0080 (3) | 0.56677 (16) | 0.15541 (14) | 0.0505 (4) | |
C10 | 0.2310 (3) | 0.5580 (2) | 0.13853 (18) | 0.0671 (5) | |
C11 | 0.2958 (4) | 0.6699 (2) | 0.05638 (19) | 0.0743 (5) | |
C12 | 0.1363 (4) | 0.7884 (2) | −0.00757 (18) | 0.0729 (5) | |
C13 | −0.0814 (4) | 0.7915 (2) | 0.01424 (19) | 0.0756 (5) | |
H1A | −0.221 (3) | 0.4906 (17) | 0.4768 (16) | 0.071* | |
H1B | −0.093 (3) | 0.6066 (19) | 0.3876 (16) | 0.071* | |
H2A | −0.142 (3) | 0.2319 (18) | 0.4227 (16) | 0.072* | |
H2B | 0.054 (3) | 0.2263 (18) | 0.5172 (19) | 0.072* | |
H4 | 0.451 (3) | 0.199 (2) | 0.3766 (18) | 0.081* | |
H5 | 0.685 (4) | 0.015 (2) | 0.2968 (19) | 0.093* | |
H6 | 0.539 (3) | −0.172 (2) | 0.2275 (18) | 0.090* | |
H7 | 0.164 (3) | −0.153 (2) | 0.2563 (17) | 0.083* | |
H8A | −0.238 (3) | 0.4707 (19) | 0.2416 (17) | 0.073* | |
H8B | −0.031 (3) | 0.353 (2) | 0.1993 (16) | 0.073* | |
H10 | 0.332 (3) | 0.472 (2) | 0.1842 (17) | 0.081* | |
H11 | 0.446 (4) | 0.663 (2) | 0.0446 (19) | 0.089* | |
H12 | 0.175 (3) | 0.873 (2) | −0.0652 (19) | 0.088* | |
H13 | −0.196 (3) | 0.877 (2) | −0.0311 (19) | 0.091* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0673 (9) | 0.0435 (7) | 0.0520 (8) | −0.0148 (6) | −0.0001 (6) | −0.0129 (6) |
N2 | 0.0650 (9) | 0.0502 (8) | 0.0616 (8) | −0.0190 (7) | 0.0087 (7) | −0.0164 (6) |
N3 | 0.0602 (9) | 0.0640 (9) | 0.0610 (9) | −0.0061 (7) | −0.0020 (7) | −0.0095 (7) |
C1 | 0.0636 (11) | 0.0503 (9) | 0.0626 (10) | −0.0099 (8) | −0.0019 (8) | −0.0184 (8) |
C2 | 0.0700 (12) | 0.0489 (9) | 0.0626 (11) | −0.0188 (8) | 0.0128 (9) | −0.0140 (8) |
C3 | 0.0589 (10) | 0.0433 (8) | 0.0485 (9) | −0.0132 (7) | 0.0016 (7) | −0.0049 (6) |
C4 | 0.0576 (11) | 0.0677 (12) | 0.0796 (13) | −0.0201 (9) | 0.0004 (9) | −0.0145 (9) |
C5 | 0.0526 (11) | 0.0844 (14) | 0.0809 (14) | −0.0043 (11) | 0.0043 (10) | −0.0024 (11) |
C6 | 0.0812 (15) | 0.0612 (12) | 0.0690 (12) | 0.0024 (10) | 0.0136 (10) | −0.0116 (9) |
C7 | 0.0876 (14) | 0.0563 (10) | 0.0671 (11) | −0.0200 (10) | 0.0135 (10) | −0.0222 (9) |
C8 | 0.0699 (12) | 0.0578 (10) | 0.0588 (10) | −0.0207 (9) | −0.0070 (9) | −0.0171 (8) |
C9 | 0.0563 (10) | 0.0510 (9) | 0.0452 (8) | −0.0092 (7) | −0.0036 (7) | −0.0180 (7) |
C10 | 0.0577 (11) | 0.0645 (11) | 0.0751 (12) | −0.0099 (9) | −0.0054 (9) | −0.0131 (9) |
C11 | 0.0649 (12) | 0.0892 (14) | 0.0769 (13) | −0.0280 (12) | 0.0112 (10) | −0.0274 (11) |
C12 | 0.0936 (16) | 0.0729 (13) | 0.0568 (11) | −0.0335 (12) | 0.0051 (10) | −0.0097 (9) |
C13 | 0.0845 (15) | 0.0632 (11) | 0.0664 (12) | −0.0080 (10) | −0.0071 (10) | 0.0003 (9) |
N1—C8 | 1.459 (2) | C2—H2A | 1.03 (2) |
N1—C1 | 1.464 (2) | C2—H2B | 1.00 (2) |
N1—C2 | 1.467 (2) | C4—C5 | 1.384 (3) |
N2—C3 | 1.330 (2) | C4—H4 | 0.95 (2) |
N2—C7 | 1.337 (2) | C7—C6 | 1.366 (3) |
N3—C9 | 1.331 (2) | C7—H7 | 0.99 (2) |
N3—C13 | 1.337 (2) | C13—C12 | 1.361 (3) |
C3—C4 | 1.379 (2) | C13—H13 | 0.98 (2) |
C3—C2 | 1.504 (2) | C10—C11 | 1.368 (3) |
C9—C10 | 1.376 (2) | C10—H10 | 0.94 (2) |
C9—C8 | 1.499 (2) | C5—C6 | 1.361 (3) |
C1—C1i | 1.507 (3) | C5—H5 | 0.93 (2) |
C1—H1A | 1.01 (2) | C11—C12 | 1.360 (3) |
C1—H1B | 1.00 (2) | C11—H11 | 0.92 (2) |
C8—H8A | 1.01 (2) | C6—H6 | 0.98 (2) |
C8—H8B | 1.00 (2) | C12—H12 | 0.98 (2) |
C8—N1—C1 | 110.61 (13) | C3—C2—H2B | 109.0 (10) |
C8—N1—C2 | 110.19 (13) | H2A—C2—H2B | 104.9 (14) |
C1—N1—C2 | 112.02 (13) | C3—C4—C5 | 119.23 (19) |
C3—N2—C7 | 117.41 (15) | C3—C4—H4 | 120.6 (12) |
C9—N3—C13 | 117.54 (16) | C5—C4—H4 | 120.1 (12) |
N2—C3—C4 | 122.11 (15) | N2—C7—C6 | 124.02 (19) |
N2—C3—C2 | 116.69 (14) | N2—C7—H7 | 116.9 (11) |
C4—C3—C2 | 121.18 (15) | C6—C7—H7 | 119.0 (11) |
N3—C9—C10 | 121.40 (16) | N3—C13—C12 | 123.81 (19) |
N3—C9—C8 | 116.65 (15) | N3—C13—H13 | 118.0 (12) |
C10—C9—C8 | 121.89 (16) | C12—C13—H13 | 118.2 (12) |
N1—C1—C1i | 112.30 (18) | C11—C10—C9 | 120.00 (18) |
N1—C1—H1A | 110.9 (9) | C11—C10—H10 | 123.1 (11) |
C1i—C1—H1A | 108.6 (10) | C9—C10—H10 | 116.9 (11) |
N1—C1—H1B | 106.3 (10) | C6—C5—C4 | 118.83 (19) |
C1i—C1—H1B | 108.3 (10) | C6—C5—H5 | 126.4 (13) |
H1A—C1—H1B | 110.4 (13) | C4—C5—H5 | 114.8 (13) |
N1—C8—C9 | 113.28 (13) | C12—C11—C10 | 118.8 (2) |
N1—C8—H8A | 111.7 (11) | C12—C11—H11 | 121.5 (12) |
C9—C8—H8A | 110.5 (10) | C10—C11—H11 | 119.8 (12) |
N1—C8—H8B | 107.2 (10) | C5—C6—C7 | 118.40 (19) |
C9—C8—H8B | 109.0 (10) | C5—C6—H6 | 123.4 (11) |
H8A—C8—H8B | 104.7 (14) | C7—C6—H6 | 118.2 (11) |
N1—C2—C3 | 111.91 (13) | C11—C12—C13 | 118.47 (18) |
N1—C2—H2A | 113.7 (9) | C11—C12—H12 | 121.6 (12) |
C3—C2—H2A | 109.2 (10) | C13—C12—H12 | 119.9 (12) |
N1—C2—H2B | 107.9 (10) | ||
C7—N2—C3—C4 | 0.9 (2) | C4—C3—C2—N1 | 50.3 (2) |
C7—N2—C3—C2 | −177.2 (1) | N2—C3—C4—C5 | −0.5 (3) |
C13—N3—C9—C10 | 0.6 (2) | C2—C3—C4—C5 | 177.5 (2) |
C13—N3—C9—C8 | −176.7 (2) | C3—N2—C7—C6 | −1.0 (3) |
C8—N1—C1—C1i | −159.6 (2) | C9—N3—C13—C12 | 0.2 (3) |
C2—N1—C1—C1i | 77.1 (2) | N3—C9—C10—C11 | −0.6 (3) |
C1—N1—C8—C9 | 76.8 (2) | C8—C9—C10—C11 | 176.5 (2) |
C2—N1—C8—C9 | −158.8 (1) | C3—C4—C5—C6 | 0.2 (3) |
N3—C9—C8—N1 | −130.8 (1) | C9—C10—C11—C12 | −0.1 (3) |
C10—C9—C8—N1 | 52.0 (2) | C4—C5—C6—C7 | −0.3 (3) |
C8—N1—C2—C3 | 72.5 (2) | N2—C7—C6—C5 | 0.7 (3) |
C1—N1—C2—C3 | −163.9 (1) | C10—C11—C12—C13 | 0.8 (3) |
N2—C3—C2—N1 | −131.5 (2) | N3—C13—C12—C11 | −0.9 (3) |
Symmetry code: (i) −x, −y+1, −z+1. |
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