Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617017260/cu3120sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017260/cu31207asup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017260/cu31207bsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017260/cu31207csup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017260/cu31208asup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017260/cu31208bsup6.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229617017260/cu3120sup7.pdf |
CCDC references: 1588691; 1588690; 1588689; 1588688; 1588687
For all structures, data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).
C16H16ClN3 | Dx = 1.271 Mg m−3 |
Mr = 285.77 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbcm | Cell parameters from 8043 reflections |
a = 8.8317 (14) Å | θ = 4.0–28.0° |
b = 24.261 (3) Å | µ = 0.25 mm−1 |
c = 6.9706 (14) Å | T = 298 K |
V = 1493.6 (4) Å3 | Parallelepiped, yellow |
Z = 4 | 0.19 × 0.14 × 0.11 mm |
F(000) = 600 |
Agilent SuperNova Dual Source diffractometer with an Atlas detector | 1658 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 1417 reflections with I > 2σ(I) |
Detector resolution: 5.3072 pixels mm-1 | Rint = 0.060 |
ω scans | θmax = 26.4°, θmin = 2.9° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −11→11 |
Tmin = 0.828, Tmax = 1.000 | k = −30→30 |
29057 measured reflections | l = −8→8 |
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: mixed |
wR(F2) = 0.139 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0667P)2 + 0.5084P] where P = (Fo2 + 2Fc2)/3 |
1658 reflections | (Δ/σ)max < 0.001 |
124 parameters | Δρmax = 0.16 e Å−3 |
15 restraints | Δρmin = −0.29 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Cl4 | 0.86106 (9) | 0.04937 (3) | 0.750000 | 0.0877 (4) | |
C524 | 0.8268 (3) | 0.11940 (10) | 0.750000 | 0.0526 (6) | |
C525 | 0.9478 (3) | 0.15465 (10) | 0.750000 | 0.0564 (6) | |
H525 | 1.046360 | 0.141182 | 0.750000 | 0.068* | |
C526 | 0.9201 (3) | 0.21091 (10) | 0.750000 | 0.0565 (7) | |
H526 | 1.001353 | 0.235280 | 0.750000 | 0.068* | |
C521 | 0.7739 (3) | 0.23155 (9) | 0.750000 | 0.0417 (5) | |
C522 | 0.6541 (3) | 0.19449 (10) | 0.750000 | 0.0507 (6) | |
H522 | 0.555139 | 0.207616 | 0.750000 | 0.061* | |
C523 | 0.6800 (3) | 0.13859 (10) | 0.750000 | 0.0585 (7) | |
H523 | 0.599257 | 0.113988 | 0.750000 | 0.070* | |
C52 | 0.7474 (3) | 0.29093 (9) | 0.750000 | 0.0472 (6) | |
H52 | 0.830509 | 0.314479 | 0.750000 | 0.057* | |
N51 | 0.6172 (2) | 0.31146 (8) | 0.750000 | 0.0479 (5) | |
C5 | 0.5981 (3) | 0.36838 (9) | 0.750000 | 0.0455 (5) | |
N1 | 0.4523 (2) | 0.39007 (7) | 0.750000 | 0.0472 (5) | |
C11 | 0.3066 (3) | 0.35837 (9) | 0.750000 | 0.0534 (6) | |
C12 | 0.1732 (3) | 0.39860 (12) | 0.750000 | 0.0702 (9) | |
H12B | 0.172 (3) | 0.4216 (12) | 0.624 (4) | 0.105* | |
H12A | 0.083 (4) | 0.3774 (17) | 0.750000 | 0.105* | |
C13 | 0.3003 (2) | 0.32337 (7) | 0.5675 (3) | 0.0663 (6) | |
H13A | 0.309936 | 0.346819 | 0.457270 | 0.100* | |
H13B | 0.205339 | 0.304180 | 0.562117 | 0.100* | |
H13C | 0.381713 | 0.297150 | 0.568733 | 0.100* | |
C2 | 0.4636 (3) | 0.44565 (9) | 0.750000 | 0.0536 (6) | |
H2 | 0.382738 | 0.470218 | 0.750000 | 0.064* | |
C3 | 0.6145 (3) | 0.45988 (10) | 0.750000 | 0.0519 (6) | |
C4 | 0.6996 (3) | 0.41106 (10) | 0.750000 | 0.0522 (6) | |
H4 | 0.804606 | 0.408227 | 0.750000 | 0.063* | |
C31 | 0.6689 (3) | 0.51488 (11) | 0.750000 | 0.0616 (7) | |
N32 | 0.7127 (4) | 0.55906 (10) | 0.750000 | 0.0859 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl4 | 0.0744 (5) | 0.0333 (4) | 0.1552 (9) | 0.0047 (3) | 0.000 | 0.000 |
C524 | 0.0525 (12) | 0.0331 (11) | 0.0721 (15) | 0.0018 (9) | 0.000 | 0.000 |
C525 | 0.0426 (12) | 0.0408 (12) | 0.0856 (17) | 0.0061 (9) | 0.000 | 0.000 |
C526 | 0.0409 (12) | 0.0392 (12) | 0.0893 (19) | −0.0015 (10) | 0.000 | 0.000 |
C521 | 0.0446 (12) | 0.0345 (11) | 0.0462 (11) | 0.0005 (9) | 0.000 | 0.000 |
C522 | 0.0388 (11) | 0.0413 (13) | 0.0720 (16) | 0.0023 (9) | 0.000 | 0.000 |
C523 | 0.0472 (12) | 0.0409 (13) | 0.0873 (18) | −0.0058 (10) | 0.000 | 0.000 |
C52 | 0.0447 (12) | 0.0359 (11) | 0.0610 (14) | −0.0004 (9) | 0.000 | 0.000 |
N51 | 0.0469 (11) | 0.0319 (9) | 0.0649 (12) | 0.0035 (8) | 0.000 | 0.000 |
C5 | 0.0448 (12) | 0.0327 (11) | 0.0590 (13) | 0.0017 (9) | 0.000 | 0.000 |
N1 | 0.0419 (10) | 0.0272 (9) | 0.0726 (13) | −0.0002 (7) | 0.000 | 0.000 |
C11 | 0.0412 (12) | 0.0316 (11) | 0.0874 (18) | −0.0019 (9) | 0.000 | 0.000 |
C12 | 0.0434 (13) | 0.0432 (14) | 0.124 (3) | 0.0012 (11) | 0.000 | 0.000 |
C13 | 0.0548 (10) | 0.0458 (10) | 0.0983 (16) | −0.0041 (7) | −0.0129 (10) | −0.0109 (10) |
C2 | 0.0512 (13) | 0.0289 (11) | 0.0808 (17) | 0.0007 (9) | 0.000 | 0.000 |
C3 | 0.0524 (13) | 0.0332 (11) | 0.0701 (15) | −0.0052 (10) | 0.000 | 0.000 |
C4 | 0.0438 (12) | 0.0404 (12) | 0.0723 (16) | −0.0028 (9) | 0.000 | 0.000 |
C31 | 0.0607 (15) | 0.0399 (14) | 0.0842 (19) | −0.0078 (11) | 0.000 | 0.000 |
N32 | 0.0908 (19) | 0.0425 (13) | 0.124 (2) | −0.0189 (13) | 0.000 | 0.000 |
Cl4—C524 | 1.726 (2) | N1—C2 | 1.352 (3) |
C524—C525 | 1.368 (4) | N1—C11 | 1.499 (3) |
C524—C523 | 1.378 (4) | C11—C12 | 1.530 (4) |
C525—C526 | 1.387 (3) | C11—C13 | 1.530 (2) |
C525—H525 | 0.9300 | C11—C13i | 1.530 (2) |
C526—C521 | 1.384 (3) | C12—H12B | 1.04 (3) |
C526—H526 | 0.9300 | C12—H12A | 0.95 (4) |
C521—C522 | 1.389 (3) | C13—H13A | 0.9600 |
C521—C52 | 1.459 (3) | C13—H13B | 0.9600 |
C522—C523 | 1.375 (3) | C13—H13C | 0.9600 |
C522—H522 | 0.9300 | C2—C3 | 1.377 (4) |
C523—H523 | 0.9300 | C2—H2 | 0.9300 |
C52—N51 | 1.254 (3) | C3—C4 | 1.403 (3) |
C52—H52 | 0.9300 | C3—C31 | 1.418 (3) |
N51—C5 | 1.391 (3) | C4—H4 | 0.9300 |
C5—C4 | 1.369 (3) | C31—N32 | 1.140 (3) |
C5—N1 | 1.391 (3) | ||
C525—C524—C523 | 121.6 (2) | C5—N1—C11 | 126.92 (18) |
C525—C524—Cl4 | 118.60 (19) | N1—C11—C12 | 109.50 (19) |
C523—C524—Cl4 | 119.84 (19) | N1—C11—C13 | 108.40 (13) |
C524—C525—C526 | 118.5 (2) | C12—C11—C13 | 109.04 (13) |
C524—C525—H525 | 120.7 | N1—C11—C13i | 108.40 (13) |
C526—C525—H525 | 120.7 | C12—C11—C13i | 109.04 (13) |
C521—C526—C525 | 121.4 (2) | C13—C11—C13i | 112.4 (2) |
C521—C526—H526 | 119.3 | C11—C12—H12B | 110.5 (15) |
C525—C526—H526 | 119.3 | C11—C12—H12A | 107 (2) |
C526—C521—C522 | 118.4 (2) | H12B—C12—H12A | 106.6 (18) |
C526—C521—C52 | 120.4 (2) | C11—C13—H13A | 109.5 |
C522—C521—C52 | 121.1 (2) | C11—C13—H13B | 109.5 |
C523—C522—C521 | 120.8 (2) | H13A—C13—H13B | 109.5 |
C523—C522—H522 | 119.6 | C11—C13—H13C | 109.5 |
C521—C522—H522 | 119.6 | H13A—C13—H13C | 109.5 |
C522—C523—C524 | 119.3 (2) | H13B—C13—H13C | 109.5 |
C522—C523—H523 | 120.3 | N1—C2—C3 | 108.7 (2) |
C524—C523—H523 | 120.3 | N1—C2—H2 | 125.6 |
N51—C52—C521 | 122.7 (2) | C3—C2—H2 | 125.6 |
N51—C52—H52 | 118.7 | C2—C3—C4 | 107.9 (2) |
C521—C52—H52 | 118.7 | C2—C3—C31 | 124.3 (2) |
C52—N51—C5 | 120.4 (2) | C4—C3—C31 | 127.8 (2) |
C4—C5—N51 | 132.2 (2) | C5—C4—C3 | 106.7 (2) |
C4—C5—N1 | 108.65 (19) | C5—C4—H4 | 126.6 |
N51—C5—N1 | 119.17 (19) | C3—C4—H4 | 126.6 |
C2—N1—C5 | 108.00 (18) | N32—C31—C3 | 179.9 (3) |
C2—N1—C11 | 125.08 (19) | ||
C523—C524—C525—C526 | 0.0 | C4—C5—N1—C11 | 180.0 |
Cl4—C524—C525—C526 | 180.0 | N51—C5—N1—C11 | 0.0 |
C524—C525—C526—C521 | 0.0 | C2—N1—C11—C12 | 0.0 |
C525—C526—C521—C522 | 0.0 | C5—N1—C11—C12 | 180.0 |
C525—C526—C521—C52 | 180.0 | C2—N1—C11—C13 | 118.85 (13) |
C526—C521—C522—C523 | 0.0 | C5—N1—C11—C13 | −61.15 (13) |
C52—C521—C522—C523 | 180.0 | C2—N1—C11—C13i | −118.85 (13) |
C521—C522—C523—C524 | 0.0 | C5—N1—C11—C13i | 61.15 (13) |
C525—C524—C523—C522 | 0.0 | C5—N1—C2—C3 | 0.0 |
Cl4—C524—C523—C522 | 180.0 | C11—N1—C2—C3 | 180.0 |
C526—C521—C52—N51 | 180.0 | N1—C2—C3—C4 | 0.0 |
C522—C521—C52—N51 | 0.0 | N1—C2—C3—C31 | 180.0 |
C521—C52—N51—C5 | 180.0 | N51—C5—C4—C3 | 180.0 |
C52—N51—C5—C4 | 0.0 | N1—C5—C4—C3 | 0.0 |
C52—N51—C5—N1 | 180.0 | C2—C3—C4—C5 | 0.0 |
C4—C5—N1—C2 | 0.0 | C31—C3—C4—C5 | 180.0 |
N51—C5—N1—C2 | 180.0 |
Symmetry code: (i) x, y, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13C···N51 | 0.96 | 2.46 | 3.088 (3) | 123 |
C13—H13A···N32ii | 0.96 | 2.71 | 3.612 (3) | 157 |
C2—H2···Cl4iii | 0.93 | 2.89 | 3.815 (3) | 178 |
Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) −x+1, y+1/2, z. |
C16H15Cl2N3 | F(000) = 664 |
Mr = 320.21 | Dx = 1.345 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 6.5428 (7) Å | Cell parameters from 4572 reflections |
b = 7.9586 (11) Å | θ = 4.2–27.4° |
c = 30.415 (5) Å | µ = 0.41 mm−1 |
β = 92.987 (13)° | T = 298 K |
V = 1581.6 (4) Å3 | Parallelepiped, yellow |
Z = 4 | 0.29 × 0.15 × 0.11 mm |
Agilent SuperNova Dual Source diffractometer with an Atlas detector | 3206 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 2577 reflections with I > 2σ(I) |
Detector resolution: 5.3072 pixels mm-1 | Rint = 0.063 |
ω scans | θmax = 26.4°, θmin = 2.9° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −8→8 |
Tmin = 0.425, Tmax = 1.000 | k = −9→9 |
16620 measured reflections | l = −37→36 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.152 | w = 1/[σ2(Fo2) + (0.0692P)2 + 0.5679P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3206 reflections | Δρmax = 0.30 e Å−3 |
194 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Extinction correction: SHELXL2016 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.012 (2) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Cl4 | 0.03393 (12) | 0.27165 (12) | 0.50311 (3) | 0.1005 (3) | |
C524 | 0.2456 (4) | 0.2442 (4) | 0.47138 (9) | 0.0666 (7) | |
C525 | 0.3505 (4) | 0.3820 (4) | 0.45781 (9) | 0.0727 (7) | |
H525 | 0.309572 | 0.489756 | 0.465247 | 0.087* | |
C526 | 0.5187 (4) | 0.3577 (3) | 0.43283 (9) | 0.0665 (7) | |
H526 | 0.590837 | 0.450933 | 0.423662 | 0.080* | |
C521 | 0.5831 (3) | 0.1988 (3) | 0.42101 (7) | 0.0510 (5) | |
C522 | 0.4701 (3) | 0.0640 (3) | 0.43527 (7) | 0.0553 (5) | |
C523 | 0.3015 (3) | 0.0851 (4) | 0.46058 (8) | 0.0654 (7) | |
H523 | 0.228285 | −0.007213 | 0.469952 | 0.079* | |
Cl2 | 0.53068 (11) | −0.13911 (9) | 0.42043 (3) | 0.0821 (3) | |
C52 | 0.7592 (3) | 0.1784 (3) | 0.39353 (7) | 0.0523 (5) | |
H52 | 0.805700 | 0.071026 | 0.387308 | 0.063* | |
N51 | 0.8487 (3) | 0.3046 (2) | 0.37821 (6) | 0.0523 (5) | |
C5 | 1.0160 (3) | 0.2813 (3) | 0.35257 (7) | 0.0467 (5) | |
N1 | 1.0828 (2) | 0.4132 (2) | 0.32711 (6) | 0.0477 (4) | |
C2 | 1.2493 (3) | 0.3597 (3) | 0.30603 (7) | 0.0513 (5) | |
H2 | 1.322469 | 0.423055 | 0.286539 | 0.062* | |
C3 | 1.2912 (3) | 0.1975 (3) | 0.31820 (7) | 0.0498 (5) | |
C4 | 1.1429 (3) | 0.1476 (3) | 0.34734 (7) | 0.0509 (5) | |
H4 | 1.133051 | 0.042866 | 0.360606 | 0.061* | |
C31 | 1.4582 (3) | 0.0989 (3) | 0.30407 (8) | 0.0578 (6) | |
N32 | 1.5904 (3) | 0.0178 (3) | 0.29370 (8) | 0.0779 (7) | |
C11 | 0.9860 (3) | 0.5830 (3) | 0.32291 (8) | 0.0561 (6) | |
C12 | 1.0988 (5) | 0.6875 (3) | 0.28982 (11) | 0.0811 (8) | |
H12A | 1.087322 | 0.634141 | 0.261486 | 0.122* | |
H12B | 1.240566 | 0.696318 | 0.299372 | 0.122* | |
H12C | 1.039524 | 0.797714 | 0.287768 | 0.122* | |
C13 | 0.7630 (4) | 0.5615 (4) | 0.30588 (10) | 0.0774 (8) | |
H13A | 0.704093 | 0.669864 | 0.299540 | 0.116* | |
H13B | 0.687146 | 0.506433 | 0.327891 | 0.116* | |
H13C | 0.758162 | 0.494840 | 0.279548 | 0.116* | |
C14 | 1.0010 (5) | 0.6677 (3) | 0.36761 (10) | 0.0770 (8) | |
H14A | 1.142340 | 0.684605 | 0.376579 | 0.115* | |
H14B | 0.937733 | 0.597860 | 0.388756 | 0.115* | |
H14C | 0.932350 | 0.774287 | 0.365803 | 0.115* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl4 | 0.0738 (5) | 0.1201 (7) | 0.1128 (7) | 0.0060 (4) | 0.0553 (5) | 0.0066 (5) |
C524 | 0.0513 (13) | 0.0881 (18) | 0.0623 (14) | −0.0009 (12) | 0.0213 (11) | 0.0019 (13) |
C525 | 0.0668 (15) | 0.0722 (17) | 0.0819 (18) | 0.0025 (13) | 0.0299 (13) | −0.0070 (14) |
C526 | 0.0613 (14) | 0.0606 (15) | 0.0802 (17) | −0.0061 (11) | 0.0281 (12) | −0.0025 (12) |
C521 | 0.0451 (11) | 0.0582 (13) | 0.0507 (11) | −0.0051 (9) | 0.0117 (9) | 0.0024 (10) |
C522 | 0.0524 (11) | 0.0607 (13) | 0.0536 (12) | −0.0034 (10) | 0.0118 (9) | 0.0085 (10) |
C523 | 0.0534 (13) | 0.0768 (17) | 0.0677 (15) | −0.0085 (12) | 0.0187 (11) | 0.0151 (13) |
Cl2 | 0.0864 (5) | 0.0578 (4) | 0.1053 (6) | −0.0051 (3) | 0.0349 (4) | 0.0081 (3) |
C52 | 0.0496 (11) | 0.0518 (12) | 0.0569 (12) | −0.0021 (9) | 0.0157 (9) | 0.0002 (10) |
N51 | 0.0471 (9) | 0.0541 (10) | 0.0571 (10) | −0.0024 (8) | 0.0179 (8) | −0.0007 (8) |
C5 | 0.0422 (10) | 0.0493 (11) | 0.0496 (11) | −0.0045 (8) | 0.0111 (8) | −0.0002 (9) |
N1 | 0.0445 (9) | 0.0458 (9) | 0.0538 (10) | −0.0027 (7) | 0.0137 (7) | 0.0011 (8) |
C2 | 0.0450 (11) | 0.0567 (13) | 0.0539 (12) | −0.0049 (9) | 0.0167 (9) | 0.0001 (10) |
C3 | 0.0440 (10) | 0.0549 (12) | 0.0513 (11) | 0.0004 (9) | 0.0117 (9) | −0.0059 (9) |
C4 | 0.0517 (11) | 0.0479 (11) | 0.0543 (12) | −0.0020 (9) | 0.0134 (9) | 0.0005 (9) |
C31 | 0.0546 (12) | 0.0633 (14) | 0.0567 (13) | 0.0033 (11) | 0.0142 (10) | −0.0041 (11) |
N32 | 0.0713 (13) | 0.0855 (16) | 0.0790 (14) | 0.0203 (12) | 0.0255 (11) | −0.0075 (12) |
C11 | 0.0529 (12) | 0.0465 (11) | 0.0703 (14) | 0.0005 (9) | 0.0178 (10) | 0.0039 (10) |
C12 | 0.0856 (19) | 0.0593 (15) | 0.102 (2) | 0.0056 (13) | 0.0365 (16) | 0.0230 (15) |
C13 | 0.0582 (14) | 0.0753 (17) | 0.099 (2) | 0.0083 (13) | 0.0018 (13) | 0.0176 (15) |
C14 | 0.0852 (18) | 0.0540 (14) | 0.094 (2) | −0.0080 (13) | 0.0267 (15) | −0.0155 (13) |
Cl4—C524 | 1.743 (2) | C2—C3 | 1.367 (3) |
C524—C523 | 1.363 (4) | C2—H2 | 0.9300 |
C524—C525 | 1.369 (4) | C3—C4 | 1.405 (3) |
C525—C526 | 1.383 (3) | C3—C31 | 1.429 (3) |
C525—H525 | 0.9300 | C4—H4 | 0.9300 |
C526—C521 | 1.386 (3) | C31—N32 | 1.137 (3) |
C526—H526 | 0.9300 | C11—C14 | 1.516 (4) |
C521—C522 | 1.386 (3) | C11—C12 | 1.525 (3) |
C521—C52 | 1.467 (3) | C11—C13 | 1.532 (3) |
C522—C523 | 1.388 (3) | C12—H12A | 0.9600 |
C522—Cl2 | 1.730 (3) | C12—H12B | 0.9600 |
C523—H523 | 0.9300 | C12—H12C | 0.9600 |
C52—N51 | 1.263 (3) | C13—H13A | 0.9600 |
C52—H52 | 0.9300 | C13—H13B | 0.9600 |
N51—C5 | 1.389 (3) | C13—H13C | 0.9600 |
C5—C4 | 1.364 (3) | C14—H14A | 0.9600 |
C5—N1 | 1.389 (3) | C14—H14B | 0.9600 |
N1—C2 | 1.361 (3) | C14—H14C | 0.9600 |
N1—C11 | 1.495 (3) | ||
C523—C524—C525 | 121.8 (2) | C2—C3—C4 | 107.56 (19) |
C523—C524—Cl4 | 118.7 (2) | C2—C3—C31 | 125.7 (2) |
C525—C524—Cl4 | 119.5 (2) | C4—C3—C31 | 126.8 (2) |
C524—C525—C526 | 118.7 (2) | C5—C4—C3 | 107.35 (19) |
C524—C525—H525 | 120.7 | C5—C4—H4 | 126.3 |
C526—C525—H525 | 120.7 | C3—C4—H4 | 126.3 |
C525—C526—C521 | 122.1 (2) | N32—C31—C3 | 178.3 (3) |
C525—C526—H526 | 118.9 | N1—C11—C14 | 108.5 (2) |
C521—C526—H526 | 118.9 | N1—C11—C12 | 109.38 (18) |
C526—C521—C522 | 116.8 (2) | C14—C11—C12 | 109.8 (2) |
C526—C521—C52 | 120.5 (2) | N1—C11—C13 | 108.65 (19) |
C522—C521—C52 | 122.7 (2) | C14—C11—C13 | 111.6 (2) |
C521—C522—C523 | 122.2 (2) | C12—C11—C13 | 108.8 (2) |
C521—C522—Cl2 | 120.57 (17) | C11—C12—H12A | 109.5 |
C523—C522—Cl2 | 117.24 (19) | C11—C12—H12B | 109.5 |
C524—C523—C522 | 118.5 (2) | H12A—C12—H12B | 109.5 |
C524—C523—H523 | 120.7 | C11—C12—H12C | 109.5 |
C522—C523—H523 | 120.7 | H12A—C12—H12C | 109.5 |
N51—C52—C521 | 121.0 (2) | H12B—C12—H12C | 109.5 |
N51—C52—H52 | 119.5 | C11—C13—H13A | 109.5 |
C521—C52—H52 | 119.5 | C11—C13—H13B | 109.5 |
C52—N51—C5 | 119.67 (19) | H13A—C13—H13B | 109.5 |
C4—C5—N51 | 132.22 (19) | C11—C13—H13C | 109.5 |
C4—C5—N1 | 108.26 (17) | H13A—C13—H13C | 109.5 |
N51—C5—N1 | 119.50 (18) | H13B—C13—H13C | 109.5 |
C2—N1—C5 | 108.00 (17) | C11—C14—H14A | 109.5 |
C2—N1—C11 | 126.06 (17) | C11—C14—H14B | 109.5 |
C5—N1—C11 | 125.93 (16) | H14A—C14—H14B | 109.5 |
N1—C2—C3 | 108.82 (18) | C11—C14—H14C | 109.5 |
N1—C2—H2 | 125.6 | H14A—C14—H14C | 109.5 |
C3—C2—H2 | 125.6 | H14B—C14—H14C | 109.5 |
C523—C524—C525—C526 | −0.6 (4) | C4—C5—N1—C2 | 0.6 (2) |
Cl4—C524—C525—C526 | 179.7 (2) | N51—C5—N1—C2 | 178.83 (18) |
C524—C525—C526—C521 | 0.3 (4) | C4—C5—N1—C11 | 179.39 (19) |
C525—C526—C521—C522 | 0.3 (4) | N51—C5—N1—C11 | −2.3 (3) |
C525—C526—C521—C52 | 178.5 (2) | C5—N1—C2—C3 | −1.0 (2) |
C526—C521—C522—C523 | −0.7 (3) | C11—N1—C2—C3 | −179.8 (2) |
C52—C521—C522—C523 | −178.8 (2) | N1—C2—C3—C4 | 1.1 (2) |
C526—C521—C522—Cl2 | 177.28 (19) | N1—C2—C3—C31 | −178.1 (2) |
C52—C521—C522—Cl2 | −0.9 (3) | N51—C5—C4—C3 | −177.9 (2) |
C525—C524—C523—C522 | 0.3 (4) | N1—C5—C4—C3 | 0.1 (2) |
Cl4—C524—C523—C522 | 179.93 (18) | C2—C3—C4—C5 | −0.7 (2) |
C521—C522—C523—C524 | 0.4 (4) | C31—C3—C4—C5 | 178.4 (2) |
Cl2—C522—C523—C524 | −177.6 (2) | C2—N1—C11—C14 | −117.9 (2) |
C526—C521—C52—N51 | −3.8 (3) | C5—N1—C11—C14 | 63.5 (3) |
C522—C521—C52—N51 | 174.3 (2) | C2—N1—C11—C12 | 1.9 (3) |
C521—C52—N51—C5 | 179.55 (19) | C5—N1—C11—C12 | −176.8 (2) |
C52—N51—C5—C4 | −17.9 (4) | C2—N1—C11—C13 | 120.5 (2) |
C52—N51—C5—N1 | 164.3 (2) | C5—N1—C11—C13 | −58.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13B···N51 | 0.96 | 2.42 | 3.034 (3) | 121 |
C14—H14B···N51 | 0.96 | 2.42 | 3.079 (3) | 125 |
C52—H52···Cl2 | 0.93 | 2.69 | 3.069 (2) | 105 |
C523—H523···Cl4i | 0.93 | 2.86 | 3.788 (3) | 174 |
C2—H2···N32ii | 0.93 | 2.64 | 3.495 (3) | 152 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+3, y+1/2, −z+1/2. |
C15H16N4 | Z = 2 |
Mr = 252.32 | F(000) = 268 |
Triclinic, P1 | Dx = 1.217 Mg m−3 |
a = 8.1494 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.0629 (10) Å | Cell parameters from 6196 reflections |
c = 9.4859 (9) Å | θ = 3.5–26.3° |
α = 92.465 (8)° | µ = 0.08 mm−1 |
β = 97.113 (8)° | T = 298 K |
γ = 97.136 (9)° | Parallelepiped, yellow |
V = 688.61 (12) Å3 | 0.31 × 0.28 × 0.19 mm |
Agilent SuperNova Dual Source diffractometer with an Atlas detector | 2807 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 2419 reflections with I > 2σ(I) |
Detector resolution: 5.3072 pixels mm-1 | Rint = 0.045 |
ω scans | θmax = 26.4°, θmin = 3.0° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −9→10 |
Tmin = 0.831, Tmax = 1.000 | k = −11→11 |
14493 measured reflections | l = −11→11 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.151 | w = 1/[σ2(Fo2) + (0.0646P)2 + 0.2783P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
2807 reflections | Δρmax = 0.23 e Å−3 |
176 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL2016 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.049 (7) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.61053 (16) | 0.72071 (15) | 0.16935 (14) | 0.0405 (4) | |
C5 | 0.7818 (2) | 0.75187 (19) | 0.20946 (17) | 0.0415 (4) | |
N51 | 0.84879 (17) | 0.72275 (16) | 0.34611 (15) | 0.0441 (4) | |
C52 | 0.9862 (2) | 0.7983 (2) | 0.39940 (18) | 0.0441 (4) | |
H52 | 1.039742 | 0.867236 | 0.344820 | 0.053* | |
C521 | 1.0622 (2) | 0.77937 (19) | 0.54474 (17) | 0.0407 (4) | |
C522 | 1.0027 (2) | 0.6685 (2) | 0.6283 (2) | 0.0539 (5) | |
H522 | 0.912991 | 0.597861 | 0.592067 | 0.065* | |
C523 | 1.0780 (3) | 0.6642 (3) | 0.7656 (2) | 0.0638 (6) | |
H523 | 1.037087 | 0.588644 | 0.820113 | 0.077* | |
N524 | 1.2068 (2) | 0.7622 (2) | 0.82561 (17) | 0.0614 (5) | |
C525 | 1.2629 (2) | 0.8670 (2) | 0.7440 (2) | 0.0543 (5) | |
H525 | 1.352426 | 0.936378 | 0.783235 | 0.065* | |
C526 | 1.1973 (2) | 0.8801 (2) | 0.60481 (19) | 0.0471 (4) | |
H526 | 1.242843 | 0.955235 | 0.552054 | 0.057* | |
C4 | 0.8526 (2) | 0.8119 (2) | 0.09749 (18) | 0.0477 (4) | |
H4 | 0.965593 | 0.841379 | 0.094746 | 0.057* | |
C3 | 0.7221 (2) | 0.8203 (2) | −0.01232 (17) | 0.0448 (4) | |
C2 | 0.5754 (2) | 0.76432 (19) | 0.03553 (17) | 0.0430 (4) | |
H2 | 0.469588 | 0.757594 | −0.015734 | 0.052* | |
C31 | 0.7340 (2) | 0.8783 (2) | −0.14841 (19) | 0.0518 (5) | |
N32 | 0.7428 (3) | 0.9256 (2) | −0.25738 (19) | 0.0730 (6) | |
C11 | 0.4845 (2) | 0.6527 (2) | 0.25875 (18) | 0.0449 (4) | |
C14 | 0.4869 (3) | 0.7555 (2) | 0.3906 (2) | 0.0573 (5) | |
H14A | 0.403992 | 0.714575 | 0.446723 | 0.086* | |
H14B | 0.463250 | 0.851904 | 0.362193 | 0.086* | |
H14C | 0.594983 | 0.764949 | 0.445949 | 0.086* | |
C12 | 0.3125 (3) | 0.6369 (3) | 0.1725 (2) | 0.0740 (7) | |
H12A | 0.230620 | 0.595492 | 0.229443 | 0.111* | |
H12B | 0.310401 | 0.572099 | 0.089351 | 0.111* | |
H12C | 0.287761 | 0.733002 | 0.144313 | 0.111* | |
C13 | 0.5274 (3) | 0.4994 (2) | 0.2981 (2) | 0.0575 (5) | |
H13A | 0.442234 | 0.451203 | 0.348188 | 0.086* | |
H13B | 0.632707 | 0.510129 | 0.357858 | 0.086* | |
H13C | 0.534114 | 0.440257 | 0.213104 | 0.086* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0352 (7) | 0.0496 (8) | 0.0336 (7) | −0.0013 (6) | −0.0019 (5) | 0.0073 (6) |
C5 | 0.0366 (9) | 0.0482 (9) | 0.0371 (8) | 0.0007 (7) | −0.0020 (6) | 0.0057 (7) |
N51 | 0.0369 (8) | 0.0544 (8) | 0.0383 (7) | 0.0034 (6) | −0.0039 (6) | 0.0062 (6) |
C52 | 0.0381 (9) | 0.0531 (10) | 0.0392 (9) | 0.0023 (7) | −0.0004 (7) | 0.0062 (7) |
C521 | 0.0319 (8) | 0.0492 (9) | 0.0401 (9) | 0.0069 (7) | −0.0012 (7) | 0.0028 (7) |
C522 | 0.0419 (10) | 0.0627 (11) | 0.0511 (10) | −0.0054 (8) | −0.0078 (8) | 0.0119 (9) |
C523 | 0.0575 (12) | 0.0761 (14) | 0.0518 (11) | −0.0049 (10) | −0.0086 (9) | 0.0212 (10) |
N524 | 0.0572 (10) | 0.0738 (11) | 0.0473 (9) | 0.0049 (8) | −0.0137 (7) | 0.0078 (8) |
C525 | 0.0475 (11) | 0.0562 (11) | 0.0525 (11) | 0.0008 (8) | −0.0121 (8) | −0.0027 (8) |
C526 | 0.0417 (9) | 0.0491 (9) | 0.0474 (10) | 0.0016 (7) | −0.0022 (7) | 0.0025 (7) |
C4 | 0.0363 (9) | 0.0618 (11) | 0.0426 (9) | −0.0010 (7) | 0.0017 (7) | 0.0080 (8) |
C3 | 0.0438 (9) | 0.0538 (10) | 0.0346 (8) | −0.0004 (7) | 0.0015 (7) | 0.0058 (7) |
C2 | 0.0400 (9) | 0.0513 (9) | 0.0344 (8) | −0.0002 (7) | −0.0039 (7) | 0.0058 (7) |
C31 | 0.0475 (10) | 0.0624 (11) | 0.0434 (10) | −0.0022 (8) | 0.0044 (8) | 0.0117 (8) |
N32 | 0.0728 (13) | 0.0933 (14) | 0.0525 (10) | 0.0008 (10) | 0.0091 (9) | 0.0281 (10) |
C11 | 0.0377 (9) | 0.0543 (10) | 0.0404 (9) | −0.0037 (7) | 0.0028 (7) | 0.0109 (7) |
C14 | 0.0607 (12) | 0.0613 (12) | 0.0537 (11) | 0.0094 (9) | 0.0182 (9) | 0.0100 (9) |
C12 | 0.0398 (11) | 0.1106 (19) | 0.0653 (13) | −0.0148 (11) | −0.0024 (9) | 0.0319 (13) |
C13 | 0.0664 (13) | 0.0492 (10) | 0.0535 (11) | −0.0056 (9) | 0.0057 (9) | 0.0083 (8) |
N1—C2 | 1.353 (2) | C4—C3 | 1.405 (2) |
N1—C5 | 1.391 (2) | C4—H4 | 0.9300 |
N1—C11 | 1.502 (2) | C3—C2 | 1.377 (2) |
C5—C4 | 1.371 (2) | C3—C31 | 1.424 (2) |
C5—N51 | 1.392 (2) | C2—H2 | 0.9300 |
N51—C52 | 1.272 (2) | C31—N32 | 1.143 (2) |
C52—C521 | 1.466 (2) | C11—C12 | 1.520 (3) |
C52—H52 | 0.9300 | C11—C14 | 1.524 (3) |
C521—C522 | 1.385 (3) | C11—C13 | 1.525 (3) |
C521—C526 | 1.385 (2) | C14—H14A | 0.9600 |
C522—C523 | 1.373 (3) | C14—H14B | 0.9600 |
C522—H522 | 0.9300 | C14—H14C | 0.9600 |
C523—N524 | 1.338 (3) | C12—H12A | 0.9600 |
C523—H523 | 0.9300 | C12—H12B | 0.9600 |
N524—C525 | 1.324 (3) | C12—H12C | 0.9600 |
C525—C526 | 1.378 (3) | C13—H13A | 0.9600 |
C525—H525 | 0.9300 | C13—H13B | 0.9600 |
C526—H526 | 0.9300 | C13—H13C | 0.9600 |
C2—N1—C5 | 108.18 (14) | C2—C3—C31 | 124.78 (16) |
C2—N1—C11 | 125.40 (14) | C4—C3—C31 | 127.59 (17) |
C5—N1—C11 | 126.41 (13) | N1—C2—C3 | 108.83 (15) |
C4—C5—N1 | 108.36 (14) | N1—C2—H2 | 125.6 |
C4—C5—N51 | 132.38 (15) | C3—C2—H2 | 125.6 |
N1—C5—N51 | 119.25 (14) | N32—C31—C3 | 179.5 (2) |
C52—N51—C5 | 117.94 (15) | N1—C11—C12 | 108.79 (14) |
N51—C52—C521 | 121.62 (16) | N1—C11—C14 | 108.93 (14) |
N51—C52—H52 | 119.2 | C12—C11—C14 | 109.19 (18) |
C521—C52—H52 | 119.2 | N1—C11—C13 | 108.73 (15) |
C522—C521—C526 | 117.55 (16) | C12—C11—C13 | 109.60 (17) |
C522—C521—C52 | 123.47 (16) | C14—C11—C13 | 111.55 (15) |
C526—C521—C52 | 118.93 (16) | C11—C14—H14A | 109.5 |
C523—C522—C521 | 119.04 (18) | C11—C14—H14B | 109.5 |
C523—C522—H522 | 120.5 | H14A—C14—H14B | 109.5 |
C521—C522—H522 | 120.5 | C11—C14—H14C | 109.5 |
N524—C523—C522 | 124.00 (19) | H14A—C14—H14C | 109.5 |
N524—C523—H523 | 118.0 | H14B—C14—H14C | 109.5 |
C522—C523—H523 | 118.0 | C11—C12—H12A | 109.5 |
C525—N524—C523 | 116.20 (16) | C11—C12—H12B | 109.5 |
N524—C525—C526 | 124.30 (17) | H12A—C12—H12B | 109.5 |
N524—C525—H525 | 117.8 | C11—C12—H12C | 109.5 |
C526—C525—H525 | 117.8 | H12A—C12—H12C | 109.5 |
C525—C526—C521 | 118.88 (17) | H12B—C12—H12C | 109.5 |
C525—C526—H526 | 120.6 | C11—C13—H13A | 109.5 |
C521—C526—H526 | 120.6 | C11—C13—H13B | 109.5 |
C5—C4—C3 | 106.99 (15) | H13A—C13—H13B | 109.5 |
C5—C4—H4 | 126.5 | C11—C13—H13C | 109.5 |
C3—C4—H4 | 126.5 | H13A—C13—H13C | 109.5 |
C2—C3—C4 | 107.62 (15) | H13B—C13—H13C | 109.5 |
C2—N1—C5—C4 | −1.5 (2) | C52—C521—C526—C525 | 176.50 (16) |
C11—N1—C5—C4 | 179.40 (16) | N1—C5—C4—C3 | 1.1 (2) |
C2—N1—C5—N51 | 177.32 (15) | N51—C5—C4—C3 | −177.47 (18) |
C11—N1—C5—N51 | −1.8 (3) | C5—C4—C3—C2 | −0.3 (2) |
C4—C5—N51—C52 | 24.2 (3) | C5—C4—C3—C31 | 178.36 (18) |
N1—C5—N51—C52 | −154.26 (17) | C5—N1—C2—C3 | 1.3 (2) |
C5—N51—C52—C521 | 177.45 (15) | C11—N1—C2—C3 | −179.61 (15) |
N51—C52—C521—C522 | 7.6 (3) | C4—C3—C2—N1 | −0.6 (2) |
N51—C52—C521—C526 | −170.00 (17) | C31—C3—C2—N1 | −179.32 (17) |
C526—C521—C522—C523 | 0.6 (3) | C2—N1—C11—C12 | 1.7 (3) |
C52—C521—C522—C523 | −177.03 (19) | C5—N1—C11—C12 | −179.35 (19) |
C521—C522—C523—N524 | 0.4 (4) | C2—N1—C11—C14 | −117.26 (18) |
C522—C523—N524—C525 | −0.8 (4) | C5—N1—C11—C14 | 61.7 (2) |
C523—N524—C525—C526 | 0.1 (3) | C2—N1—C11—C13 | 120.98 (18) |
N524—C525—C526—C521 | 0.9 (3) | C5—N1—C11—C13 | −60.0 (2) |
C522—C521—C526—C525 | −1.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14C···N51 | 0.96 | 2.44 | 3.079 (3) | 123 |
C13—H13B···N51 | 0.96 | 2.46 | 3.078 (2) | 122 |
C2—H2···N524i | 0.93 | 2.47 | 3.390 (2) | 172 |
C52—H52···N32ii | 0.93 | 2.65 | 3.551 (3) | 163 |
C525—H525···Cg1iii | 0.93 | 2.93 | 3.486 (2) | 120 |
Symmetry codes: (i) x−1, y, z−1; (ii) −x+2, −y+2, −z; (iii) −x+2, −y+2, −z+1. |
C16H18ClN3 | F(000) = 608 |
Mr = 287.78 | Dx = 1.231 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2422 (10) Å | Cell parameters from 8656 reflections |
b = 9.2361 (10) Å | θ = 4.1–27.1° |
c = 20.623 (2) Å | µ = 0.24 mm−1 |
β = 98.521 (11)° | T = 298 K |
V = 1552.6 (3) Å3 | Parallelepiped, yellow |
Z = 4 | 0.30 × 0.17 × 0.13 mm |
Agilent SuperNova Dual Source diffractometer with an Atlas detector | 4416 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 2938 reflections with I > 2σ(I) |
Detector resolution: 5.3072 pixels mm-1 | Rint = 0.053 |
ω scans | θmax = 30.6°, θmin = 3.0° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −11→11 |
Tmin = 0.663, Tmax = 1.000 | k = −13→12 |
36135 measured reflections | l = −28→28 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.067 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.198 | w = 1/[σ2(Fo2) + (0.0678P)2 + 0.6772P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
4416 reflections | Δρmax = 0.43 e Å−3 |
188 parameters | Δρmin = −0.36 e Å−3 |
15 restraints | Extinction correction: SHELXL2016 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.012 (2) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Cl4 | 1.15686 (10) | −0.31760 (11) | 0.50375 (5) | 0.1107 (4) | |
H51 | 0.640 (5) | 0.064 (4) | 0.644 (2) | 0.133* | |
C524 | 0.9855 (3) | −0.2574 (3) | 0.53619 (13) | 0.0684 (5) | |
C525 | 0.9558 (3) | −0.3102 (3) | 0.59510 (14) | 0.0720 (5) | |
H525 | 1.026427 | −0.377368 | 0.617961 | 0.086* | |
C526 | 0.8191 (3) | −0.2623 (3) | 0.62024 (13) | 0.0674 (6) | |
H526 | 0.798278 | −0.297728 | 0.660405 | 0.081* | |
C521 | 0.7129 (2) | −0.1630 (2) | 0.58688 (10) | 0.0497 (5) | |
C52 | 0.5601 (3) | −0.1174 (2) | 0.61352 (12) | 0.0565 (5) | |
H52A | 0.464500 | −0.152522 | 0.584675 | 0.068* | |
H52B | 0.559862 | −0.161050 | 0.656291 | 0.068* | |
N51 | 0.5496 (2) | 0.03900 (19) | 0.61932 (9) | 0.0518 (4) | |
C5 | 0.4117 (2) | 0.0863 (2) | 0.64573 (9) | 0.0448 (4) | |
N1 | 0.3873 (2) | 0.23093 (17) | 0.66020 (8) | 0.0459 (4) | |
C11 | 0.4908 (3) | 0.3581 (2) | 0.64722 (10) | 0.0501 (5) | |
C12 | 0.4250 (3) | 0.4941 (3) | 0.67646 (15) | 0.0735 (7) | |
H12A | 0.494831 | 0.574754 | 0.670576 | 0.110* | |
H12B | 0.422788 | 0.479470 | 0.722403 | 0.110* | |
H12C | 0.315898 | 0.513630 | 0.654760 | 0.110* | |
C14 | 0.4828 (3) | 0.3756 (3) | 0.57346 (13) | 0.0715 (7) | |
H14A | 0.518452 | 0.287662 | 0.555134 | 0.107* | |
H14B | 0.552876 | 0.453841 | 0.564541 | 0.107* | |
H14C | 0.371954 | 0.396275 | 0.554169 | 0.107* | |
C13 | 0.6682 (3) | 0.3361 (3) | 0.67952 (15) | 0.0705 (7) | |
H13A | 0.723910 | 0.274796 | 0.652354 | 0.106* | |
H13B | 0.669556 | 0.291631 | 0.721660 | 0.106* | |
H13C | 0.722679 | 0.428175 | 0.684832 | 0.106* | |
C2 | 0.2414 (3) | 0.2406 (2) | 0.68459 (10) | 0.0519 (5) | |
H2 | 0.196252 | 0.324937 | 0.698869 | 0.062* | |
C3 | 0.1740 (2) | 0.1057 (2) | 0.68435 (10) | 0.0498 (5) | |
C4 | 0.2815 (2) | 0.0071 (2) | 0.65935 (10) | 0.0492 (5) | |
H4 | 0.266113 | −0.092036 | 0.653439 | 0.059* | |
C31 | 0.0258 (3) | 0.0692 (3) | 0.70868 (11) | 0.0560 (5) | |
N32 | −0.0910 (3) | 0.0381 (3) | 0.72869 (12) | 0.0760 (6) | |
C522 | 0.7481 (3) | −0.1102 (3) | 0.52805 (11) | 0.0632 (6) | |
H522 | 0.678976 | −0.041770 | 0.505313 | 0.076* | |
C523 | 0.8841 (3) | −0.1573 (3) | 0.50226 (13) | 0.0675 (5) | |
H523 | 0.906526 | −0.121350 | 0.462399 | 0.081* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl4 | 0.0763 (5) | 0.1201 (7) | 0.1472 (8) | 0.0265 (5) | 0.0541 (5) | −0.0121 (6) |
C524 | 0.0576 (9) | 0.0735 (11) | 0.0769 (10) | 0.0129 (8) | 0.0194 (8) | −0.0049 (8) |
C525 | 0.0607 (10) | 0.0748 (12) | 0.0825 (11) | 0.0164 (9) | 0.0171 (9) | 0.0029 (9) |
C526 | 0.0637 (14) | 0.0653 (14) | 0.0759 (15) | 0.0128 (11) | 0.0198 (12) | 0.0128 (12) |
C521 | 0.0470 (10) | 0.0447 (10) | 0.0586 (11) | 0.0027 (8) | 0.0115 (8) | −0.0073 (8) |
C52 | 0.0544 (12) | 0.0453 (11) | 0.0736 (14) | 0.0025 (9) | 0.0216 (10) | −0.0039 (10) |
N51 | 0.0477 (9) | 0.0437 (9) | 0.0683 (11) | 0.0049 (7) | 0.0223 (8) | −0.0017 (8) |
C5 | 0.0437 (9) | 0.0447 (10) | 0.0481 (9) | 0.0047 (8) | 0.0131 (8) | 0.0030 (8) |
N1 | 0.0450 (8) | 0.0436 (8) | 0.0523 (9) | 0.0037 (7) | 0.0174 (7) | 0.0022 (7) |
C11 | 0.0497 (11) | 0.0419 (10) | 0.0616 (11) | −0.0002 (8) | 0.0175 (9) | 0.0012 (8) |
C12 | 0.0739 (16) | 0.0449 (12) | 0.108 (2) | 0.0025 (11) | 0.0345 (14) | −0.0033 (12) |
C14 | 0.0778 (17) | 0.0702 (16) | 0.0704 (15) | −0.0061 (13) | 0.0240 (13) | 0.0134 (12) |
C13 | 0.0583 (13) | 0.0546 (13) | 0.0962 (18) | −0.0027 (11) | 0.0032 (12) | −0.0106 (13) |
C2 | 0.0483 (11) | 0.0538 (11) | 0.0571 (11) | 0.0081 (9) | 0.0195 (9) | 0.0039 (9) |
C3 | 0.0430 (10) | 0.0560 (11) | 0.0525 (10) | 0.0034 (8) | 0.0138 (8) | 0.0054 (9) |
C4 | 0.0468 (10) | 0.0466 (10) | 0.0561 (11) | −0.0002 (8) | 0.0137 (8) | 0.0031 (8) |
C31 | 0.0468 (11) | 0.0601 (13) | 0.0636 (12) | 0.0040 (9) | 0.0164 (9) | 0.0062 (10) |
N32 | 0.0559 (11) | 0.0793 (15) | 0.0994 (16) | −0.0018 (10) | 0.0327 (11) | 0.0079 (12) |
C522 | 0.0577 (13) | 0.0749 (15) | 0.0575 (12) | 0.0174 (11) | 0.0098 (10) | 0.0035 (11) |
C523 | 0.0596 (10) | 0.0761 (12) | 0.0699 (11) | 0.0108 (9) | 0.0193 (8) | −0.0036 (8) |
Cl4—C524 | 1.741 (2) | C11—C13 | 1.528 (3) |
C524—C525 | 1.365 (4) | C12—H12A | 0.9600 |
C524—C523 | 1.368 (4) | C12—H12B | 0.9600 |
C525—C526 | 1.380 (3) | C12—H12C | 0.9600 |
C525—H525 | 0.9300 | C14—H14A | 0.9600 |
C526—C521 | 1.380 (3) | C14—H14B | 0.9600 |
C526—H526 | 0.9300 | C14—H14C | 0.9600 |
C521—C522 | 1.377 (3) | C13—H13A | 0.9600 |
C521—C52 | 1.507 (3) | C13—H13B | 0.9600 |
C52—N51 | 1.453 (3) | C13—H13C | 0.9600 |
C52—H52A | 0.9700 | C2—C3 | 1.364 (3) |
C52—H52B | 0.9700 | C2—H2 | 0.9300 |
N51—C5 | 1.401 (2) | C3—C4 | 1.420 (3) |
N51—H51 | 0.87 (4) | C3—C31 | 1.427 (3) |
C5—C4 | 1.361 (3) | C4—H4 | 0.9300 |
C5—N1 | 1.390 (2) | C31—N32 | 1.139 (3) |
N1—C2 | 1.373 (2) | C522—C523 | 1.381 (3) |
N1—C11 | 1.499 (3) | C522—H522 | 0.9300 |
C11—C14 | 1.521 (3) | C523—H523 | 0.9300 |
C11—C12 | 1.528 (3) | ||
C525—C524—C523 | 121.3 (2) | C11—C12—H12B | 109.5 |
C525—C524—Cl4 | 119.4 (2) | H12A—C12—H12B | 109.5 |
C523—C524—Cl4 | 119.2 (2) | C11—C12—H12C | 109.5 |
C524—C525—C526 | 119.0 (2) | H12A—C12—H12C | 109.5 |
C524—C525—H525 | 120.5 | H12B—C12—H12C | 109.5 |
C526—C525—H525 | 120.5 | C11—C14—H14A | 109.5 |
C521—C526—C525 | 121.2 (2) | C11—C14—H14B | 109.5 |
C521—C526—H526 | 119.4 | H14A—C14—H14B | 109.5 |
C525—C526—H526 | 119.4 | C11—C14—H14C | 109.5 |
C522—C521—C526 | 118.3 (2) | H14A—C14—H14C | 109.5 |
C522—C521—C52 | 121.3 (2) | H14B—C14—H14C | 109.5 |
C526—C521—C52 | 120.4 (2) | C11—C13—H13A | 109.5 |
N51—C52—C521 | 111.75 (17) | C11—C13—H13B | 109.5 |
N51—C52—H52A | 109.3 | H13A—C13—H13B | 109.5 |
C521—C52—H52A | 109.3 | C11—C13—H13C | 109.5 |
N51—C52—H52B | 109.3 | H13A—C13—H13C | 109.5 |
C521—C52—H52B | 109.3 | H13B—C13—H13C | 109.5 |
H52A—C52—H52B | 107.9 | C3—C2—N1 | 108.54 (18) |
C5—N51—C52 | 113.79 (17) | C3—C2—H2 | 125.7 |
C5—N51—H51 | 111 (3) | N1—C2—H2 | 125.7 |
C52—N51—H51 | 105 (3) | C2—C3—C4 | 108.11 (18) |
C4—C5—N1 | 109.20 (17) | C2—C3—C31 | 125.7 (2) |
C4—C5—N51 | 128.49 (19) | C4—C3—C31 | 126.1 (2) |
N1—C5—N51 | 122.28 (17) | C5—C4—C3 | 106.49 (19) |
C2—N1—C5 | 107.64 (16) | C5—C4—H4 | 126.8 |
C2—N1—C11 | 124.53 (17) | C3—C4—H4 | 126.8 |
C5—N1—C11 | 127.65 (16) | N32—C31—C3 | 178.8 (3) |
N1—C11—C14 | 108.68 (18) | C521—C522—C523 | 121.1 (2) |
N1—C11—C12 | 109.21 (17) | C521—C522—H522 | 119.4 |
C14—C11—C12 | 110.0 (2) | C523—C522—H522 | 119.4 |
N1—C11—C13 | 110.57 (17) | C524—C523—C522 | 119.0 (2) |
C14—C11—C13 | 110.3 (2) | C524—C523—H523 | 120.5 |
C12—C11—C13 | 108.1 (2) | C522—C523—H523 | 120.5 |
C11—C12—H12A | 109.5 | ||
C523—C524—C525—C526 | 0.8 (5) | C5—N1—C11—C12 | −175.4 (2) |
Cl4—C524—C525—C526 | −179.7 (2) | C2—N1—C11—C13 | 128.8 (2) |
C524—C525—C526—C521 | 0.1 (4) | C5—N1—C11—C13 | −56.6 (3) |
C525—C526—C521—C522 | −1.1 (4) | C5—N1—C2—C3 | −1.1 (2) |
C525—C526—C521—C52 | 177.0 (2) | C11—N1—C2—C3 | 174.42 (18) |
C522—C521—C52—N51 | −55.6 (3) | N1—C2—C3—C4 | 0.4 (2) |
C526—C521—C52—N51 | 126.3 (2) | N1—C2—C3—C31 | 177.03 (19) |
C521—C52—N51—C5 | −178.24 (18) | N1—C5—C4—C3 | −1.1 (2) |
C52—N51—C5—C4 | −7.8 (3) | N51—C5—C4—C3 | −179.1 (2) |
C52—N51—C5—N1 | 174.49 (19) | C2—C3—C4—C5 | 0.4 (2) |
C4—C5—N1—C2 | 1.4 (2) | C31—C3—C4—C5 | −176.2 (2) |
N51—C5—N1—C2 | 179.51 (18) | C526—C521—C522—C523 | 1.2 (4) |
C4—C5—N1—C11 | −173.94 (18) | C52—C521—C522—C523 | −176.9 (2) |
N51—C5—N1—C11 | 4.2 (3) | C525—C524—C523—C522 | −0.7 (4) |
C2—N1—C11—C14 | −110.0 (2) | Cl4—C524—C523—C522 | 179.8 (2) |
C5—N1—C11—C14 | 64.6 (3) | C521—C522—C523—C524 | −0.3 (4) |
C2—N1—C11—C12 | 10.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13A···N51 | 0.96 | 2.64 | 3.109 (3) | 110 |
C14—H14A···N51 | 0.96 | 2.64 | 3.272 (3) | 123 |
N51—H51···N32i | 0.87 (4) | 2.62 (4) | 3.447 (3) | 159 (3) |
C2—H2···N32ii | 0.93 | 2.69 | 3.598 (3) | 165 |
Symmetry codes: (i) x+1, y, z; (ii) −x, y+1/2, −z+3/2. |
C16H17Cl2N3 | Z = 2 |
Mr = 322.22 | F(000) = 336 |
Triclinic, P1 | Dx = 1.319 Mg m−3 |
a = 8.9700 (12) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.3244 (12) Å | Cell parameters from 3822 reflections |
c = 10.4645 (14) Å | θ = 4.1–26.4° |
α = 105.057 (12)° | µ = 0.40 mm−1 |
β = 103.589 (12)° | T = 298 K |
γ = 95.078 (11)° | Parallelepiped, yellow |
V = 811.05 (19) Å3 | 0.25 × 0.11 × 0.10 mm |
Agilent SuperNova Dual Source diffractometer with an Atlas detector | 3302 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 2520 reflections with I > 2σ(I) |
Detector resolution: 5.3072 pixels mm-1 | Rint = 0.038 |
ω scans | θmax = 26.4°, θmin = 3.0° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −11→11 |
Tmin = 0.786, Tmax = 1.000 | k = −11→10 |
10849 measured reflections | l = −13→13 |
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: mixed |
wR(F2) = 0.131 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0519P)2 + 0.4113P] where P = (Fo2 + 2Fc2)/3 |
3302 reflections | (Δ/σ)max < 0.001 |
196 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Cl4 | 0.69422 (8) | 0.49248 (9) | 0.18116 (8) | 0.0732 (3) | |
H1 | 0.113 (4) | 0.109 (4) | 0.291 (4) | 0.088* | |
C524 | 0.5471 (3) | 0.4365 (3) | 0.2490 (2) | 0.0456 (5) | |
C523 | 0.4050 (3) | 0.4818 (2) | 0.2140 (2) | 0.0469 (5) | |
H523 | 0.387257 | 0.542512 | 0.155904 | 0.056* | |
C522 | 0.2892 (3) | 0.4344 (3) | 0.2681 (2) | 0.0472 (5) | |
Cl2 | 0.10932 (8) | 0.48852 (9) | 0.22039 (9) | 0.0783 (3) | |
C521 | 0.3137 (3) | 0.3468 (3) | 0.3583 (2) | 0.0463 (5) | |
C526 | 0.4590 (3) | 0.3047 (3) | 0.3891 (2) | 0.0508 (6) | |
H526 | 0.478101 | 0.244638 | 0.447741 | 0.061* | |
C525 | 0.5766 (3) | 0.3487 (3) | 0.3359 (2) | 0.0500 (6) | |
H525 | 0.673469 | 0.319480 | 0.358552 | 0.060* | |
C52 | 0.1907 (3) | 0.3006 (3) | 0.4227 (2) | 0.0561 (6) | |
H52A | 0.239053 | 0.269501 | 0.502065 | 0.067* | |
H52B | 0.140667 | 0.386169 | 0.453855 | 0.067* | |
N51 | 0.0744 (2) | 0.1780 (2) | 0.32601 (19) | 0.0463 (5) | |
C5 | −0.0481 (2) | 0.1339 (2) | 0.3766 (2) | 0.0401 (5) | |
N1 | −0.17814 (19) | 0.0318 (2) | 0.29286 (17) | 0.0390 (4) | |
C2 | −0.2757 (2) | 0.0127 (3) | 0.3715 (2) | 0.0418 (5) | |
H2 | −0.370514 | −0.051319 | 0.341052 | 0.050* | |
C3 | −0.2108 (2) | 0.1035 (3) | 0.5026 (2) | 0.0425 (5) | |
C4 | −0.0658 (2) | 0.1806 (3) | 0.5062 (2) | 0.0435 (5) | |
H4 | 0.003722 | 0.249602 | 0.582086 | 0.052* | |
C31 | −0.2807 (3) | 0.1135 (3) | 0.6128 (2) | 0.0492 (6) | |
N32 | −0.3377 (3) | 0.1186 (3) | 0.7001 (2) | 0.0722 (7) | |
C11 | −0.2132 (3) | −0.0412 (3) | 0.1416 (2) | 0.0460 (5) | |
C12 | −0.3764 (3) | −0.1323 (3) | 0.0908 (3) | 0.0606 (7) | |
H12A | −0.401479 | −0.176172 | −0.006929 | 0.091* | |
H12B | −0.449857 | −0.067449 | 0.112727 | 0.091* | |
H12C | −0.380665 | −0.210604 | 0.134553 | 0.091* | |
C13 | −0.2088 (3) | 0.0820 (4) | 0.0700 (3) | 0.0690 (8) | |
H13A | −0.233937 | 0.036828 | −0.027521 | 0.103* | |
H13B | −0.106670 | 0.140416 | 0.101246 | 0.103* | |
H13C | −0.283064 | 0.146062 | 0.091343 | 0.103* | |
C14 | −0.0968 (3) | −0.1470 (3) | 0.1142 (3) | 0.0679 (8) | |
H14A | −0.121486 | −0.197649 | 0.017687 | 0.102* | |
H14B | −0.101679 | −0.219814 | 0.163876 | 0.102* | |
H14C | 0.006008 | −0.090129 | 0.143956 | 0.102* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl4 | 0.0587 (4) | 0.0854 (5) | 0.0907 (6) | 0.0034 (3) | 0.0395 (4) | 0.0366 (4) |
C524 | 0.0406 (12) | 0.0457 (13) | 0.0485 (13) | −0.0019 (9) | 0.0163 (10) | 0.0093 (10) |
C523 | 0.0495 (13) | 0.0408 (12) | 0.0503 (13) | 0.0045 (10) | 0.0135 (10) | 0.0139 (10) |
C522 | 0.0372 (11) | 0.0434 (12) | 0.0525 (13) | 0.0051 (9) | 0.0103 (10) | 0.0016 (10) |
Cl2 | 0.0462 (4) | 0.0761 (5) | 0.1094 (6) | 0.0206 (3) | 0.0172 (4) | 0.0210 (4) |
C521 | 0.0419 (12) | 0.0474 (13) | 0.0407 (12) | −0.0072 (10) | 0.0125 (9) | 0.0011 (10) |
C526 | 0.0469 (13) | 0.0535 (14) | 0.0499 (14) | −0.0034 (10) | 0.0083 (10) | 0.0193 (11) |
C525 | 0.0365 (11) | 0.0527 (14) | 0.0584 (15) | 0.0028 (10) | 0.0092 (10) | 0.0166 (12) |
C52 | 0.0467 (13) | 0.0644 (16) | 0.0460 (13) | −0.0132 (11) | 0.0168 (11) | 0.0004 (12) |
N51 | 0.0378 (10) | 0.0546 (12) | 0.0401 (10) | −0.0059 (8) | 0.0148 (8) | 0.0033 (9) |
C5 | 0.0335 (10) | 0.0472 (12) | 0.0384 (11) | 0.0016 (9) | 0.0100 (8) | 0.0119 (9) |
N1 | 0.0330 (9) | 0.0475 (10) | 0.0355 (9) | 0.0020 (7) | 0.0100 (7) | 0.0109 (8) |
C2 | 0.0324 (10) | 0.0516 (13) | 0.0451 (12) | 0.0035 (9) | 0.0127 (9) | 0.0190 (10) |
C3 | 0.0375 (11) | 0.0555 (13) | 0.0411 (12) | 0.0088 (9) | 0.0149 (9) | 0.0207 (10) |
C4 | 0.0374 (11) | 0.0549 (13) | 0.0353 (11) | 0.0016 (9) | 0.0099 (9) | 0.0101 (10) |
C31 | 0.0390 (12) | 0.0649 (15) | 0.0453 (13) | 0.0037 (10) | 0.0133 (10) | 0.0183 (11) |
N32 | 0.0591 (14) | 0.1044 (19) | 0.0547 (13) | −0.0047 (13) | 0.0272 (11) | 0.0209 (13) |
C11 | 0.0404 (11) | 0.0579 (14) | 0.0336 (11) | 0.0007 (10) | 0.0079 (9) | 0.0072 (10) |
C12 | 0.0469 (14) | 0.0711 (17) | 0.0483 (14) | −0.0064 (12) | 0.0031 (11) | 0.0049 (13) |
C13 | 0.0688 (17) | 0.090 (2) | 0.0438 (14) | −0.0053 (15) | 0.0045 (12) | 0.0284 (14) |
C14 | 0.0534 (15) | 0.0785 (19) | 0.0581 (16) | 0.0107 (13) | 0.0166 (12) | −0.0055 (14) |
Cl4—C524 | 1.740 (2) | N1—C11 | 1.496 (3) |
C524—C525 | 1.371 (3) | C2—C3 | 1.368 (3) |
C524—C523 | 1.376 (3) | C2—H2 | 0.9300 |
C523—C522 | 1.386 (3) | C3—C4 | 1.417 (3) |
C523—H523 | 0.9300 | C3—C31 | 1.424 (3) |
C522—C521 | 1.393 (3) | C4—H4 | 0.9300 |
C522—Cl2 | 1.733 (2) | C31—N32 | 1.140 (3) |
C521—C526 | 1.384 (3) | C11—C14 | 1.523 (4) |
C521—C52 | 1.508 (3) | C11—C12 | 1.526 (3) |
C526—C525 | 1.382 (3) | C11—C13 | 1.527 (4) |
C526—H526 | 0.9300 | C12—H12A | 0.9600 |
C525—H525 | 0.9300 | C12—H12B | 0.9600 |
C52—N51 | 1.453 (3) | C12—H12C | 0.9600 |
C52—H52A | 0.9700 | C13—H13A | 0.9600 |
C52—H52B | 0.9700 | C13—H13B | 0.9600 |
N51—C5 | 1.401 (3) | C13—H13C | 0.9600 |
N51—H1 | 0.80 (3) | C14—H14A | 0.9600 |
C5—C4 | 1.363 (3) | C14—H14B | 0.9600 |
C5—N1 | 1.388 (3) | C14—H14C | 0.9600 |
N1—C2 | 1.364 (3) | ||
C525—C524—C523 | 122.0 (2) | N1—C2—H2 | 125.7 |
C525—C524—Cl4 | 118.90 (18) | C3—C2—H2 | 125.7 |
C523—C524—Cl4 | 119.08 (18) | C2—C3—C4 | 107.84 (19) |
C524—C523—C522 | 118.0 (2) | C2—C3—C31 | 124.3 (2) |
C524—C523—H523 | 121.0 | C4—C3—C31 | 127.9 (2) |
C522—C523—H523 | 121.0 | C5—C4—C3 | 106.64 (19) |
C523—C522—C521 | 122.2 (2) | C5—C4—H4 | 126.7 |
C523—C522—Cl2 | 117.64 (19) | C3—C4—H4 | 126.7 |
C521—C522—Cl2 | 120.13 (18) | N32—C31—C3 | 178.7 (3) |
C526—C521—C522 | 117.0 (2) | N1—C11—C14 | 108.99 (18) |
C526—C521—C52 | 120.4 (2) | N1—C11—C12 | 108.95 (18) |
C522—C521—C52 | 122.6 (2) | C14—C11—C12 | 108.9 (2) |
C525—C526—C521 | 122.3 (2) | N1—C11—C13 | 108.52 (19) |
C525—C526—H526 | 118.9 | C14—C11—C13 | 112.8 (2) |
C521—C526—H526 | 118.9 | C12—C11—C13 | 108.6 (2) |
C524—C525—C526 | 118.5 (2) | C11—C12—H12A | 109.5 |
C524—C525—H525 | 120.8 | C11—C12—H12B | 109.5 |
C526—C525—H525 | 120.8 | H12A—C12—H12B | 109.5 |
N51—C52—C521 | 111.43 (18) | C11—C12—H12C | 109.5 |
N51—C52—H52A | 109.3 | H12A—C12—H12C | 109.5 |
C521—C52—H52A | 109.3 | H12B—C12—H12C | 109.5 |
N51—C52—H52B | 109.3 | C11—C13—H13A | 109.5 |
C521—C52—H52B | 109.3 | C11—C13—H13B | 109.5 |
H52A—C52—H52B | 108.0 | H13A—C13—H13B | 109.5 |
C5—N51—C52 | 114.63 (18) | C11—C13—H13C | 109.5 |
C5—N51—H1 | 114 (2) | H13A—C13—H13C | 109.5 |
C52—N51—H1 | 112 (3) | H13B—C13—H13C | 109.5 |
C4—C5—N1 | 108.88 (18) | C11—C14—H14A | 109.5 |
C4—C5—N51 | 129.11 (19) | C11—C14—H14B | 109.5 |
N1—C5—N51 | 121.99 (18) | H14A—C14—H14B | 109.5 |
C2—N1—C5 | 108.01 (17) | C11—C14—H14C | 109.5 |
C2—N1—C11 | 124.53 (17) | H14A—C14—H14C | 109.5 |
C5—N1—C11 | 127.40 (17) | H14B—C14—H14C | 109.5 |
N1—C2—C3 | 108.60 (18) | ||
C525—C524—C523—C522 | −0.9 (3) | C4—C5—N1—C2 | −1.2 (2) |
Cl4—C524—C523—C522 | 179.27 (17) | N51—C5—N1—C2 | −179.8 (2) |
C524—C523—C522—C521 | 1.8 (3) | C4—C5—N1—C11 | 176.0 (2) |
C524—C523—C522—Cl2 | −178.56 (17) | N51—C5—N1—C11 | −2.6 (3) |
C523—C522—C521—C526 | −1.9 (3) | C5—N1—C2—C3 | 1.3 (2) |
Cl2—C522—C521—C526 | 178.43 (17) | C11—N1—C2—C3 | −176.03 (19) |
C523—C522—C521—C52 | 177.1 (2) | N1—C2—C3—C4 | −0.9 (3) |
Cl2—C522—C521—C52 | −2.5 (3) | N1—C2—C3—C31 | 179.7 (2) |
C522—C521—C526—C525 | 1.2 (3) | N1—C5—C4—C3 | 0.6 (3) |
C52—C521—C526—C525 | −177.9 (2) | N51—C5—C4—C3 | 179.1 (2) |
C523—C524—C525—C526 | 0.2 (4) | C2—C3—C4—C5 | 0.2 (3) |
Cl4—C524—C525—C526 | −179.94 (18) | C31—C3—C4—C5 | 179.5 (2) |
C521—C526—C525—C524 | −0.4 (4) | C2—N1—C11—C14 | −116.1 (2) |
C526—C521—C52—N51 | −103.9 (3) | C5—N1—C11—C14 | 67.1 (3) |
C522—C521—C52—N51 | 77.2 (3) | C2—N1—C11—C12 | 2.6 (3) |
C521—C52—N51—C5 | −177.0 (2) | C5—N1—C11—C12 | −174.1 (2) |
C52—N51—C5—C4 | −6.5 (4) | C2—N1—C11—C13 | 120.7 (2) |
C52—N51—C5—N1 | 171.9 (2) | C5—N1—C11—C13 | −56.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13B···N51 | 0.96 | 2.44 | 3.096 (3) | 125 |
C14—H14C···N51 | 0.96 | 2.64 | 3.247 (3) | 122 |
C2—H2···N32i | 0.93 | 2.54 | 3.411 (3) | 155 |
C525—H525···Cg1ii | 0.93 | 2.81 | 3.630 (3) | 148 |
Symmetry codes: (i) −x−1, −y, −z+1; (ii) x+1, y, z. |
Entry | Solvent | T (K) | Time | Yield (%)b |
1 | EtOH | 353c | 3 h | 70 |
2d | – | 373 | 5 min | 46 |
3d | – | 373 | 10 min | 73 |
4d | – | 373 | 15 min | 64 |
5d | – | 373 | 20 min | 56 |
6e | – | 373 | 10 min | 49 |
7f | EtOH | 373 | 10 min | 38 |
Notes: (a) reaction conditions: (2a) (0.50 mmol) and (6) (0.50 mmol); (b) isolated yield; (c) conventional heating; (d) run in 10 ml sealed tubes at a power of 300 W in the absence of solvent; (e) conventional heating with a sand bath without solvent (fusion procedure); (f) run in 10 ml sealed tubes at a power of 300 W in anhydrous ethanol (2.0 ml). |
Contact | (7a) | (7b) | (7c) | (8a) | (8b) |
H···Cl/Cl···H | 14.1 | 23.4 | - | 15.1 | 21.5 |
H···N/N···H | 13.6 | 13.5 | 24.0 | 15.3 | 15.1 |
H···H | 43.1 | 32.2 | 45.3 | 42.2 | 34.0 |
C···H/H···C | 16.8 | 16.5 | 26.3 | 24.5 | 21.2 |
C···C | 6.4 | 5.7 | 1.8 | 1.0 | 3.2 |
Others | 6.0 | 8.7 | 2.6 | 1.9 | 5.0 |