Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229621011232/vp3019sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229621011232/vp3019Isup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229621011232/vp3019sup3.pdf | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229621011232/vp3019Isup4.cml |
CCDC reference: 2071327
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).
C19H15N3O | F(000) = 1264 |
Mr = 301.34 | Dx = 1.321 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 5.7626 (4) Å | Cell parameters from 22699 reflections |
b = 36.693 (2) Å | θ = 1.5–26.4° |
c = 14.3279 (10) Å | µ = 0.08 mm−1 |
β = 90.07 (1)° | T = 296 K |
V = 3029.6 (3) Å3 | Platy, colorless |
Z = 8 | 0.3 × 0.1 × 0.01 mm |
Bruker APEX CCD diffractometer | Rint = 0.064 |
Radiation source: Fine-focus sealed tube | θmax = 26.4°, θmin = 1.5° |
ω scans | h = −7→7 |
22699 measured reflections | k = −45→44 |
5727 independent reflections | l = −17→17 |
2694 reflections with I > 2σ(I) |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.046 | w = 1/[σ2(Fo2) + (0.0478P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.120 | (Δ/σ)max < 0.001 |
S = 0.85 | Δρmax = 0.19 e Å−3 |
5727 reflections | Δρmin = −0.18 e Å−3 |
416 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0033 (4) |
Primary atom site location: structure-invariant direct methods |
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 | ||
O1 | 0.8487 (3) | 0.20497 (4) | 0.23238 (10) | 0.0598 (4) | |
C30 | 1.3534 (4) | 0.22899 (6) | 0.98529 (14) | 0.0454 (5) | |
N4 | 1.1510 (3) | 0.39648 (5) | 0.94352 (12) | 0.0518 (5) | |
O2 | 1.3545 (3) | 0.19176 (4) | 0.98453 (10) | 0.0579 (4) | |
N2 | 0.6303 (3) | 0.37302 (5) | 0.29945 (12) | 0.0522 (5) | |
N5 | 1.1258 (3) | 0.36008 (5) | 0.92836 (12) | 0.0511 (5) | |
C27 | 1.3143 (4) | 0.30474 (6) | 0.98104 (14) | 0.0466 (5) | |
C26 | 1.2927 (4) | 0.34452 (6) | 0.98067 (14) | 0.0484 (5) | |
C7 | 0.8123 (3) | 0.31784 (6) | 0.24246 (13) | 0.0473 (5) | |
C6 | 0.7922 (4) | 0.35763 (6) | 0.24576 (14) | 0.0498 (5) | |
C29 | 1.5272 (4) | 0.25042 (6) | 1.02269 (14) | 0.0531 (6) | |
H011 | 1.6574 | 0.2397 | 1.0495 | 0.064* | |
C10 | 0.8499 (4) | 0.24230 (6) | 0.23371 (14) | 0.0465 (5) | |
C11 | 0.6588 (4) | 0.25829 (6) | 0.27470 (14) | 0.0498 (5) | |
H013 | 0.5420 | 0.2437 | 0.2996 | 0.060* | |
N1 | 0.6557 (3) | 0.40952 (5) | 0.28593 (12) | 0.0547 (5) | |
C4 | 0.8340 (4) | 0.41691 (7) | 0.22376 (17) | 0.0630 (6) | |
C28 | 1.5065 (4) | 0.28785 (6) | 1.02011 (14) | 0.0540 (6) | |
H016 | 1.6244 | 0.3021 | 1.0452 | 0.065* | |
C24 | 1.3332 (4) | 0.40365 (7) | 1.00459 (16) | 0.0575 (6) | |
C12 | 0.6402 (4) | 0.29544 (6) | 0.27897 (13) | 0.0497 (5) | |
H018 | 0.5104 | 0.3059 | 0.3067 | 0.060* | |
C14 | 0.3436 (4) | 0.42863 (6) | 0.39638 (16) | 0.0552 (6) | |
C34 | 0.8304 (4) | 0.41607 (6) | 0.83628 (15) | 0.0519 (6) | |
N6 | 1.0639 (4) | 0.45767 (5) | 0.92405 (15) | 0.0688 (6) | |
C31 | 1.1611 (4) | 0.24536 (6) | 0.94523 (14) | 0.0480 (5) | |
H022 | 1.0441 | 0.2311 | 0.9195 | 0.058* | |
C8 | 1.0031 (4) | 0.30128 (6) | 0.20213 (14) | 0.0534 (6) | |
H023 | 1.1210 | 0.3157 | 0.1778 | 0.064* | |
C1 | 0.5307 (4) | 0.43665 (6) | 0.32902 (17) | 0.0605 (6) | |
C32 | 1.1426 (4) | 0.28256 (6) | 0.94333 (14) | 0.0473 (5) | |
H025 | 1.0125 | 0.2932 | 0.9162 | 0.057* | |
C33 | 1.5527 (5) | 0.17394 (7) | 1.02316 (18) | 0.0757 (7) | |
H02A | 1.5330 | 0.1480 | 1.0186 | 0.114* | |
H02B | 1.6889 | 0.1811 | 0.9893 | 0.114* | |
H02C | 1.5694 | 0.1807 | 1.0875 | 0.114* | |
C18 | 0.0503 (4) | 0.39145 (7) | 0.46527 (19) | 0.0750 (8) | |
H027 | −0.0259 | 0.3691 | 0.4686 | 0.090* | |
C5 | 0.9207 (4) | 0.38373 (6) | 0.19765 (16) | 0.0610 (6) | |
H028 | 1.0415 | 0.3794 | 0.1561 | 0.073* | |
C17 | −0.0167 (5) | 0.41912 (8) | 0.52192 (19) | 0.0788 (8) | |
H029 | −0.1396 | 0.4160 | 0.5632 | 0.095* | |
C39 | 0.7222 (4) | 0.38254 (6) | 0.82604 (16) | 0.0578 (6) | |
H030 | 0.7712 | 0.3628 | 0.8619 | 0.069* | |
C9 | 1.0225 (4) | 0.26386 (6) | 0.19722 (14) | 0.0530 (6) | |
H031 | 1.1517 | 0.2533 | 0.1694 | 0.064* | |
C25 | 1.4248 (4) | 0.37056 (6) | 1.02895 (16) | 0.0589 (6) | |
H032 | 1.5487 | 0.3662 | 1.0691 | 0.071* | |
C36 | 0.5723 (5) | 0.43964 (7) | 0.71826 (19) | 0.0778 (8) | |
H033 | 0.5237 | 0.4591 | 0.6815 | 0.093* | |
C19 | 0.2287 (4) | 0.39592 (6) | 0.40316 (17) | 0.0620 (6) | |
H034 | 0.2725 | 0.3766 | 0.3651 | 0.074* | |
C35 | 0.7492 (5) | 0.44448 (7) | 0.78109 (19) | 0.0712 (7) | |
H035 | 0.8167 | 0.4674 | 0.7869 | 0.085* | |
C21 | 1.0200 (4) | 0.42381 (6) | 0.90320 (16) | 0.0549 (6) | |
C3 | 0.8788 (5) | 0.45372 (7) | 0.20540 (19) | 0.0820 (8) | |
H037 | 0.9957 | 0.4606 | 0.1643 | 0.098* | |
C15 | 0.2757 (5) | 0.45661 (7) | 0.4554 (2) | 0.0842 (8) | |
H038 | 0.3514 | 0.4790 | 0.4526 | 0.101* | |
C13 | 1.0464 (4) | 0.18693 (7) | 0.19591 (18) | 0.0768 (8) | |
H03A | 1.0233 | 0.1610 | 0.1990 | 0.115* | |
H03B | 1.0690 | 0.1941 | 0.1321 | 0.115* | |
H03C | 1.1807 | 0.1934 | 0.2319 | 0.115* | |
N3 | 0.5776 (4) | 0.47053 (5) | 0.31016 (16) | 0.0820 (7) | |
C23 | 1.3771 (5) | 0.44045 (7) | 1.02523 (18) | 0.0726 (7) | |
H041 | 1.4960 | 0.4472 | 1.0657 | 0.087* | |
C38 | 0.5423 (4) | 0.37807 (6) | 0.76320 (18) | 0.0678 (7) | |
H042 | 0.4713 | 0.3554 | 0.7574 | 0.081* | |
C37 | 0.4672 (5) | 0.40661 (7) | 0.70919 (19) | 0.0744 (7) | |
H043 | 0.3461 | 0.4034 | 0.6670 | 0.089* | |
C22 | 1.2402 (5) | 0.46567 (7) | 0.9842 (2) | 0.0795 (8) | |
H044 | 1.2680 | 0.4901 | 0.9979 | 0.095* | |
C16 | 0.0984 (6) | 0.45174 (8) | 0.5178 (2) | 0.0919 (9) | |
H045 | 0.0561 | 0.4706 | 0.5575 | 0.110* | |
C2 | 0.7485 (6) | 0.47879 (7) | 0.2488 (2) | 0.0951 (10) | |
H049 | 0.7770 | 0.5032 | 0.2361 | 0.114* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0581 (9) | 0.0594 (10) | 0.0619 (10) | 0.0064 (8) | 0.0054 (8) | −0.0076 (8) |
C30 | 0.0482 (12) | 0.0494 (14) | 0.0387 (11) | 0.0055 (11) | 0.0044 (10) | −0.0005 (10) |
N4 | 0.0539 (11) | 0.0452 (12) | 0.0563 (12) | −0.0066 (9) | 0.0075 (10) | −0.0054 (9) |
O2 | 0.0597 (9) | 0.0549 (10) | 0.0592 (10) | 0.0099 (8) | −0.0029 (8) | 0.0028 (8) |
N2 | 0.0524 (11) | 0.0470 (11) | 0.0572 (11) | 0.0007 (9) | 0.0059 (9) | 0.0057 (9) |
N5 | 0.0554 (11) | 0.0431 (11) | 0.0548 (11) | −0.0019 (9) | 0.0041 (9) | −0.0020 (9) |
C27 | 0.0450 (12) | 0.0550 (14) | 0.0397 (12) | −0.0005 (11) | 0.0031 (10) | −0.0029 (10) |
C26 | 0.0466 (12) | 0.0566 (15) | 0.0419 (12) | −0.0032 (11) | 0.0032 (10) | −0.0030 (11) |
C7 | 0.0437 (12) | 0.0598 (14) | 0.0384 (12) | 0.0012 (10) | 0.0002 (10) | 0.0012 (10) |
C6 | 0.0478 (12) | 0.0587 (15) | 0.0429 (13) | 0.0014 (11) | −0.0003 (10) | 0.0049 (10) |
C29 | 0.0467 (13) | 0.0660 (16) | 0.0464 (13) | 0.0129 (12) | −0.0069 (11) | −0.0023 (11) |
C10 | 0.0484 (12) | 0.0530 (14) | 0.0379 (11) | 0.0060 (11) | −0.0040 (10) | −0.0067 (10) |
C11 | 0.0435 (12) | 0.0627 (15) | 0.0433 (12) | −0.0035 (11) | 0.0043 (10) | −0.0040 (11) |
N1 | 0.0563 (11) | 0.0515 (12) | 0.0564 (12) | −0.0022 (10) | 0.0067 (10) | 0.0096 (9) |
C4 | 0.0626 (15) | 0.0637 (17) | 0.0627 (15) | −0.0063 (13) | 0.0095 (13) | 0.0150 (13) |
C28 | 0.0453 (12) | 0.0674 (17) | 0.0494 (13) | 0.0020 (12) | −0.0067 (10) | −0.0094 (12) |
C24 | 0.0577 (14) | 0.0593 (16) | 0.0556 (14) | −0.0135 (12) | 0.0059 (12) | −0.0091 (12) |
C12 | 0.0445 (12) | 0.0619 (15) | 0.0428 (12) | 0.0054 (11) | 0.0069 (10) | −0.0058 (11) |
C14 | 0.0571 (13) | 0.0474 (14) | 0.0613 (15) | 0.0070 (12) | 0.0019 (12) | 0.0087 (11) |
C34 | 0.0542 (13) | 0.0422 (13) | 0.0593 (14) | 0.0029 (11) | 0.0104 (11) | 0.0002 (11) |
N6 | 0.0782 (14) | 0.0456 (13) | 0.0825 (15) | −0.0086 (11) | 0.0089 (12) | −0.0077 (11) |
C31 | 0.0443 (12) | 0.0523 (14) | 0.0473 (13) | −0.0019 (11) | −0.0016 (10) | 0.0027 (10) |
C8 | 0.0459 (12) | 0.0670 (16) | 0.0472 (13) | −0.0020 (11) | 0.0080 (10) | 0.0012 (11) |
C1 | 0.0639 (15) | 0.0458 (14) | 0.0719 (16) | 0.0045 (12) | 0.0047 (13) | 0.0051 (12) |
C32 | 0.0431 (11) | 0.0539 (14) | 0.0450 (13) | 0.0024 (10) | −0.0015 (10) | 0.0043 (10) |
C33 | 0.0801 (18) | 0.0672 (17) | 0.0797 (18) | 0.0252 (14) | −0.0122 (15) | 0.0064 (14) |
C18 | 0.0561 (15) | 0.0756 (19) | 0.093 (2) | −0.0097 (14) | 0.0114 (15) | −0.0090 (16) |
C5 | 0.0583 (14) | 0.0713 (17) | 0.0535 (14) | −0.0029 (13) | 0.0115 (12) | 0.0107 (12) |
C17 | 0.0667 (17) | 0.083 (2) | 0.086 (2) | 0.0124 (16) | 0.0194 (15) | 0.0018 (16) |
C39 | 0.0535 (14) | 0.0491 (14) | 0.0708 (16) | −0.0016 (11) | 0.0008 (13) | 0.0077 (11) |
C9 | 0.0425 (12) | 0.0695 (16) | 0.0471 (13) | 0.0057 (11) | 0.0060 (10) | −0.0041 (11) |
C25 | 0.0557 (14) | 0.0687 (17) | 0.0524 (14) | −0.0082 (13) | −0.0041 (11) | −0.0075 (12) |
C36 | 0.0819 (19) | 0.0644 (19) | 0.087 (2) | 0.0194 (15) | −0.0010 (17) | 0.0141 (15) |
C19 | 0.0505 (13) | 0.0611 (16) | 0.0745 (17) | −0.0022 (12) | 0.0037 (12) | −0.0065 (12) |
C35 | 0.0807 (18) | 0.0496 (16) | 0.0833 (18) | 0.0004 (14) | 0.0080 (16) | 0.0065 (14) |
C21 | 0.0621 (15) | 0.0410 (14) | 0.0617 (15) | −0.0033 (12) | 0.0152 (12) | −0.0007 (11) |
C3 | 0.086 (2) | 0.0701 (19) | 0.090 (2) | −0.0131 (16) | 0.0223 (17) | 0.0237 (16) |
C15 | 0.101 (2) | 0.0535 (16) | 0.099 (2) | 0.0023 (15) | 0.0240 (18) | −0.0045 (15) |
C13 | 0.0742 (17) | 0.0698 (17) | 0.0865 (19) | 0.0186 (14) | 0.0174 (15) | −0.0097 (14) |
N3 | 0.0906 (16) | 0.0501 (14) | 0.1053 (18) | −0.0009 (11) | 0.0233 (14) | 0.0178 (12) |
C23 | 0.0767 (18) | 0.0662 (19) | 0.0749 (18) | −0.0213 (15) | 0.0008 (15) | −0.0149 (14) |
C38 | 0.0613 (16) | 0.0593 (16) | 0.0828 (19) | −0.0014 (13) | −0.0047 (15) | 0.0023 (14) |
C37 | 0.0698 (17) | 0.0733 (19) | 0.0799 (19) | 0.0126 (15) | −0.0074 (15) | 0.0049 (15) |
C22 | 0.091 (2) | 0.0565 (18) | 0.091 (2) | −0.0224 (16) | 0.0099 (17) | −0.0175 (15) |
C16 | 0.111 (2) | 0.076 (2) | 0.089 (2) | 0.0215 (19) | 0.0279 (19) | −0.0090 (17) |
C2 | 0.108 (2) | 0.0565 (18) | 0.121 (3) | −0.0088 (18) | 0.026 (2) | 0.0243 (17) |
O1—C10 | 1.370 (2) | N6—C22 | 1.364 (3) |
O1—C13 | 1.418 (3) | C31—C32 | 1.369 (3) |
C30—O2 | 1.366 (2) | C31—H022 | 0.9300 |
C30—C29 | 1.381 (3) | C8—C9 | 1.379 (3) |
C30—C31 | 1.385 (3) | C8—H023 | 0.9300 |
N4—N5 | 1.361 (2) | C1—N3 | 1.301 (3) |
N4—C21 | 1.381 (3) | C32—H025 | 0.9300 |
N4—C24 | 1.391 (3) | C33—H02A | 0.9600 |
O2—C33 | 1.427 (3) | C33—H02B | 0.9600 |
N2—C6 | 1.335 (3) | C33—H02C | 0.9600 |
N2—N1 | 1.361 (2) | C18—C17 | 1.356 (3) |
N5—C26 | 1.346 (3) | C18—C19 | 1.370 (3) |
C27—C28 | 1.386 (3) | C18—H027 | 0.9300 |
C27—C32 | 1.390 (3) | C5—H028 | 0.9300 |
C27—C26 | 1.465 (3) | C17—C16 | 1.370 (4) |
C26—C25 | 1.403 (3) | C17—H029 | 0.9300 |
C7—C8 | 1.383 (3) | C39—C38 | 1.382 (3) |
C7—C12 | 1.391 (3) | C39—H030 | 0.9300 |
C7—C6 | 1.465 (3) | C9—H031 | 0.9300 |
C6—C5 | 1.394 (3) | C25—H032 | 0.9300 |
C29—C28 | 1.379 (3) | C36—C37 | 1.361 (3) |
C29—H011 | 0.9300 | C36—C35 | 1.371 (4) |
C10—C9 | 1.375 (3) | C36—H033 | 0.9300 |
C10—C11 | 1.380 (3) | C19—H034 | 0.9300 |
C11—C12 | 1.369 (3) | C35—H035 | 0.9300 |
C11—H013 | 0.9300 | C3—C2 | 1.341 (4) |
N1—C1 | 1.375 (3) | C3—H037 | 0.9300 |
N1—C4 | 1.388 (3) | C15—C16 | 1.370 (4) |
C4—C5 | 1.368 (3) | C15—H038 | 0.9300 |
C4—C3 | 1.400 (3) | C13—H03A | 0.9600 |
C28—H016 | 0.9300 | C13—H03B | 0.9600 |
C24—C25 | 1.369 (3) | C13—H03C | 0.9600 |
C24—C23 | 1.405 (3) | N3—C2 | 1.355 (3) |
C12—H018 | 0.9300 | C23—C22 | 1.350 (4) |
C14—C19 | 1.374 (3) | C23—H041 | 0.9300 |
C14—C15 | 1.387 (3) | C38—C37 | 1.372 (3) |
C14—C1 | 1.478 (3) | C38—H042 | 0.9300 |
C34—C39 | 1.387 (3) | C37—H043 | 0.9300 |
C34—C35 | 1.389 (3) | C22—H044 | 0.9300 |
C34—C21 | 1.480 (3) | C16—H045 | 0.9300 |
N6—C21 | 1.303 (3) | C2—H049 | 0.9300 |
C10—O1—C13 | 117.90 (18) | O2—C33—H02B | 109.5 |
O2—C30—C29 | 124.72 (19) | H02A—C33—H02B | 109.5 |
O2—C30—C31 | 115.72 (19) | O2—C33—H02C | 109.5 |
C29—C30—C31 | 119.6 (2) | H02A—C33—H02C | 109.5 |
N5—N4—C21 | 125.99 (18) | H02B—C33—H02C | 109.5 |
N5—N4—C24 | 111.48 (18) | C17—C18—C19 | 120.9 (3) |
C21—N4—C24 | 122.51 (19) | C17—C18—H027 | 119.6 |
C30—O2—C33 | 117.29 (18) | C19—C18—H027 | 119.6 |
C6—N2—N1 | 104.98 (17) | C4—C5—C6 | 106.4 (2) |
C26—N5—N4 | 104.55 (17) | C4—C5—H028 | 126.8 |
C28—C27—C32 | 117.6 (2) | C6—C5—H028 | 126.8 |
C28—C27—C26 | 121.0 (2) | C18—C17—C16 | 119.4 (3) |
C32—C27—C26 | 121.44 (19) | C18—C17—H029 | 120.3 |
N5—C26—C25 | 111.9 (2) | C16—C17—H029 | 120.3 |
N5—C26—C27 | 119.03 (19) | C38—C39—C34 | 120.7 (2) |
C25—C26—C27 | 129.1 (2) | C38—C39—H030 | 119.6 |
C8—C7—C12 | 117.7 (2) | C34—C39—H030 | 119.6 |
C8—C7—C6 | 120.95 (19) | C10—C9—C8 | 119.6 (2) |
C12—C7—C6 | 121.34 (19) | C10—C9—H031 | 120.2 |
N2—C6—C5 | 111.5 (2) | C8—C9—H031 | 120.2 |
N2—C6—C7 | 119.69 (19) | C24—C25—C26 | 105.6 (2) |
C5—C6—C7 | 128.8 (2) | C24—C25—H032 | 127.2 |
C28—C29—C30 | 119.62 (19) | C26—C25—H032 | 127.2 |
C28—C29—H011 | 120.2 | C37—C36—C35 | 120.6 (2) |
C30—C29—H011 | 120.2 | C37—C36—H033 | 119.7 |
O1—C10—C9 | 124.99 (19) | C35—C36—H033 | 119.7 |
O1—C10—C11 | 115.28 (19) | C18—C19—C14 | 120.8 (2) |
C9—C10—C11 | 119.7 (2) | C18—C19—H034 | 119.6 |
C12—C11—C10 | 120.3 (2) | C14—C19—H034 | 119.6 |
C12—C11—H013 | 119.8 | C36—C35—C34 | 121.8 (2) |
C10—C11—H013 | 119.8 | C36—C35—H035 | 119.1 |
N2—N1—C1 | 126.28 (18) | C34—C35—H035 | 119.1 |
N2—N1—C4 | 111.32 (18) | N6—C21—N4 | 119.4 (2) |
C1—N1—C4 | 122.37 (19) | N6—C21—C34 | 118.3 (2) |
C5—C4—N1 | 105.82 (19) | N4—C21—C34 | 122.27 (19) |
C5—C4—C3 | 137.7 (2) | C2—C3—C4 | 118.1 (3) |
N1—C4—C3 | 116.5 (2) | C2—C3—H037 | 120.9 |
C29—C28—C27 | 121.7 (2) | C4—C3—H037 | 120.9 |
C29—C28—H016 | 119.2 | C16—C15—C14 | 120.8 (3) |
C27—C28—H016 | 119.2 | C16—C15—H038 | 119.6 |
C25—C24—N4 | 106.5 (2) | C14—C15—H038 | 119.6 |
C25—C24—C23 | 136.8 (3) | O1—C13—H03A | 109.5 |
N4—C24—C23 | 116.7 (2) | O1—C13—H03B | 109.5 |
C11—C12—C7 | 121.1 (2) | H03A—C13—H03B | 109.5 |
C11—C12—H018 | 119.5 | O1—C13—H03C | 109.5 |
C7—C12—H018 | 119.5 | H03A—C13—H03C | 109.5 |
C19—C14—C15 | 117.8 (2) | H03B—C13—H03C | 109.5 |
C19—C14—C1 | 124.9 (2) | C1—N3—C2 | 120.0 (2) |
C15—C14—C1 | 117.2 (2) | C22—C23—C24 | 117.5 (2) |
C39—C34—C35 | 117.0 (2) | C22—C23—H041 | 121.2 |
C39—C34—C21 | 124.8 (2) | C24—C23—H041 | 121.2 |
C35—C34—C21 | 118.2 (2) | C37—C38—C39 | 120.9 (2) |
C21—N6—C22 | 119.6 (2) | C37—C38—H042 | 119.6 |
C32—C31—C30 | 120.2 (2) | C39—C38—H042 | 119.6 |
C32—C31—H022 | 119.9 | C36—C37—C38 | 119.1 (3) |
C30—C31—H022 | 119.9 | C36—C37—H043 | 120.5 |
C9—C8—C7 | 121.6 (2) | C38—C37—H043 | 120.5 |
C9—C8—H023 | 119.2 | C23—C22—N6 | 124.2 (2) |
C7—C8—H023 | 119.2 | C23—C22—H044 | 117.9 |
N3—C1—N1 | 119.3 (2) | N6—C22—H044 | 117.9 |
N3—C1—C14 | 118.6 (2) | C17—C16—C15 | 120.2 (3) |
N1—C1—C14 | 122.1 (2) | C17—C16—H045 | 119.9 |
C31—C32—C27 | 121.38 (19) | C15—C16—H045 | 119.9 |
C31—C32—H025 | 119.3 | C3—C2—N3 | 123.7 (3) |
C27—C32—H025 | 119.3 | C3—C2—H049 | 118.1 |
O2—C33—H02A | 109.5 | N3—C2—H049 | 118.1 |
C29—C30—O2—C33 | −1.7 (3) | C30—C31—C32—C27 | 0.0 (3) |
C31—C30—O2—C33 | 178.50 (19) | C28—C27—C32—C31 | 0.5 (3) |
C21—N4—N5—C26 | 178.80 (18) | C26—C27—C32—C31 | −178.81 (18) |
C24—N4—N5—C26 | 0.3 (2) | N1—C4—C5—C6 | −0.4 (3) |
N4—N5—C26—C25 | −0.1 (2) | C3—C4—C5—C6 | 178.8 (3) |
N4—N5—C26—C27 | 179.67 (17) | N2—C6—C5—C4 | 0.4 (3) |
C28—C27—C26—N5 | 168.55 (19) | C7—C6—C5—C4 | 179.3 (2) |
C32—C27—C26—N5 | −12.2 (3) | C19—C18—C17—C16 | −1.0 (4) |
C28—C27—C26—C25 | −11.7 (3) | C35—C34—C39—C38 | 0.2 (3) |
C32—C27—C26—C25 | 167.6 (2) | C21—C34—C39—C38 | 178.4 (2) |
N1—N2—C6—C5 | −0.2 (2) | O1—C10—C9—C8 | 179.46 (19) |
N1—N2—C6—C7 | −179.24 (17) | C11—C10—C9—C8 | 0.1 (3) |
C8—C7—C6—N2 | −167.72 (19) | C7—C8—C9—C10 | −0.5 (3) |
C12—C7—C6—N2 | 12.8 (3) | N4—C24—C25—C26 | 0.2 (2) |
C8—C7—C6—C5 | 13.5 (3) | C23—C24—C25—C26 | −179.7 (3) |
C12—C7—C6—C5 | −166.0 (2) | N5—C26—C25—C24 | 0.0 (2) |
O2—C30—C29—C28 | −179.50 (19) | C27—C26—C25—C24 | −179.8 (2) |
C31—C30—C29—C28 | 0.3 (3) | C17—C18—C19—C14 | −0.3 (4) |
C13—O1—C10—C9 | 4.1 (3) | C15—C14—C19—C18 | 1.1 (4) |
C13—O1—C10—C11 | −176.52 (19) | C1—C14—C19—C18 | −177.2 (2) |
O1—C10—C11—C12 | −179.25 (17) | C37—C36—C35—C34 | 1.2 (4) |
C9—C10—C11—C12 | 0.2 (3) | C39—C34—C35—C36 | −0.9 (3) |
C6—N2—N1—C1 | −178.0 (2) | C21—C34—C35—C36 | −179.2 (2) |
C6—N2—N1—C4 | −0.1 (2) | C22—N6—C21—N4 | 0.9 (3) |
N2—N1—C4—C5 | 0.3 (2) | C22—N6—C21—C34 | −178.8 (2) |
C1—N1—C4—C5 | 178.3 (2) | N5—N4—C21—N6 | −179.84 (19) |
N2—N1—C4—C3 | −179.1 (2) | C24—N4—C21—N6 | −1.5 (3) |
C1—N1—C4—C3 | −1.1 (3) | N5—N4—C21—C34 | −0.1 (3) |
C30—C29—C28—C27 | 0.2 (3) | C24—N4—C21—C34 | 178.30 (19) |
C32—C27—C28—C29 | −0.6 (3) | C39—C34—C21—N6 | −161.8 (2) |
C26—C27—C28—C29 | 178.67 (18) | C35—C34—C21—N6 | 16.4 (3) |
N5—N4—C24—C25 | −0.3 (2) | C39—C34—C21—N4 | 18.5 (3) |
C21—N4—C24—C25 | −178.89 (18) | C35—C34—C21—N4 | −163.4 (2) |
N5—N4—C24—C23 | 179.65 (19) | C5—C4—C3—C2 | −179.0 (3) |
C21—N4—C24—C23 | 1.1 (3) | N1—C4—C3—C2 | 0.2 (4) |
C10—C11—C12—C7 | −0.1 (3) | C19—C14—C15—C16 | −0.5 (4) |
C8—C7—C12—C11 | −0.3 (3) | C1—C14—C15—C16 | 177.9 (2) |
C6—C7—C12—C11 | 179.23 (18) | N1—C1—N3—C2 | −0.2 (4) |
O2—C30—C31—C32 | 179.38 (17) | C14—C1—N3—C2 | 179.9 (2) |
C29—C30—C31—C32 | −0.5 (3) | C25—C24—C23—C22 | 179.7 (3) |
C12—C7—C8—C9 | 0.6 (3) | N4—C24—C23—C22 | −0.2 (3) |
C6—C7—C8—C9 | −178.95 (19) | C34—C39—C38—C37 | 0.3 (4) |
N2—N1—C1—N3 | 178.8 (2) | C35—C36—C37—C38 | −0.7 (4) |
C4—N1—C1—N3 | 1.1 (3) | C39—C38—C37—C36 | 0.0 (4) |
N2—N1—C1—C14 | −1.3 (3) | C24—C23—C22—N6 | −0.3 (4) |
C4—N1—C1—C14 | −178.9 (2) | C21—N6—C22—C23 | −0.1 (4) |
C19—C14—C1—N3 | 159.8 (2) | C18—C17—C16—C15 | 1.6 (4) |
C15—C14—C1—N3 | −18.5 (3) | C14—C15—C16—C17 | −0.8 (4) |
C19—C14—C1—N1 | −20.1 (4) | C4—C3—C2—N3 | 0.7 (5) |
C15—C14—C1—N1 | 161.6 (2) | C1—N3—C2—C3 | −0.8 (5) |
π–π interactions | |||||
Type | No. | Interaction | Cg···Cga,b (Å) | Interplanar angle γ (°) | Symmetry code |
Py···Ph | 1 | Cg1···Cg4 | 3.894 (2) | 19.6 (1) | x+1, y, z |
2 | Cg5···Cg8 | 3.849 (2) | 17.6 (1) | x+1, y, z | |
C—H···π/O interactions | |||||
Type | No. | Interaction | C···Cg/C···O (Å) | \angleC—H···Cg/O (°) | Symmetry code |
Ph···Ph | 1 | C17—H···Cg8 | 4.087 (3) | 136.1 | x-1, y, z |
2 | C37—H···Cg4 | 4.026 (3) | 144.1 | x, y, z | |
OPh···OPh | 3 | C11—H···Cg7 | 3.645 (3) | 136.1 | x-1, -y+1/2, z-1/2 |
4 | C12—H···O2 | 3.408 (3)b | 133.2 | x-1, -y+1/2, z-1/2 | |
5 | C31—H···Cg3 | 3.645 (3) | 137.6 | x, -y+1/2, z+1/2 | |
6 | C32—H···O2 | 3.493 (2)c | 132.4 | x, -y+1/2, z+1/2 | |
Py···Py | 7 | C5—H···Cg6 | 3.751 (4) | 156.6 | x, y, z-1 |
8 | C3—H···Cg5 | 4.007 (4) | 136.2 | x, y, z-1 | |
9 | C25—H···Cg2 | 3.795 (4) | 144.3 | x+1, y, z+1 | |
10 | C23—H···Cg1 | 3.943 (3) | 147.8 | x+1, y, z+1 |
Notes: (a) Cg = centroid and the centroids of the rings are labelled as follows: (MOL-1/MOL-2) Py (six-membered ring) = Cg1/Cg5, Py (five-memebred ring) = Cg2/Cg6, OPh = Cg3/Cg7, Ph = Cg4/Cg8. Atoms labels are as shown in Fig. 1. (b) H···O = 2.70 Å; (c) H···O = 2.79 Å. |
Calculations are performed using DFT GGA/BLYP with van der Waals correction (DFT-D3) implemented in Quantumwise (Schneider et al., 2017) top
Compound 1 | Energy of dimer (eV) | Energy of monomer (eV) | ΔE (eV) |
Dimer 1 | -8881.142 | -4440.508 | -0.128 |
Dimer 2 | -8881.566 | -4440.508 | -0.552 |
Dimer 3 | -8881.790 | -4440.508 | -0.776 |
Dimer 4 | -8882.941 | -4440.508 | -1.927 |
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