Heterocyclic building blocks possessing ethylene spacer and amine functionality such as 1-(2-aminoethyl)piperidine (1,2-AEPi), 2-(2-aminoethyl)pyridine (2,2-AEPy) and 1-(2-aminoethyl)pyrrolidine (1,2-AEPr) were reacted with tetracyanoquinodimethane (TCNQ) to give disubstituted compounds namely bis-(1-(2-aminoethyl)piperidino)dicyanoquinodimethane (1), bis-(2-(2-aminoethyl)pyridino)dicyanoquinodimethane (2) and bis-(1-(2-aminoethyl)pyrrolidino)dicyanoquinodimethane (3). Utilization of 1,2-AEPi, 2,2-AEPy and 1,2-AEPr as disubstituents on TCNQ has resulted in interesting crystal structures. Inter- and intramolecular hydrogen-bond mediated and expanded supramolecular structures were observed in the lattices of the crystals. Strong fluorescence was observed in solids and solutions. (2) showed a strong second harmonic generation (SHG) whereas (1) and (3) were found to be SHG inactive. All compounds possess good thermal stabilities.
Supporting information
CCDC references: 1484948; 1484949; 1484950
Data collection: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) for AEPiDQ, AEPyDQ; Bruker SMART for AEPrDQ. Cell refinement: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) for AEPiDQ, AEPyDQ; Bruker SMART for AEPrDQ. Data reduction: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) for AEPiDQ, AEPyDQ; Bruker SAINT for AEPrDQ. For all compounds, program(s) used to solve structure: SHELXL2013 (Sheldrick, 2013); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013).
Crystal data top
C24H34N6 | Z = 2 |
Mr = 406.57 | F(000) = 440 |
Triclinic, P1 | Dx = 1.151 Mg m−3 |
a = 8.7977 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.3488 (10) Å | Cell parameters from 1536 reflections |
c = 13.4887 (10) Å | θ = 3.2–25.5° |
α = 84.101 (7)° | µ = 0.07 mm−1 |
β = 87.035 (7)° | T = 293 K |
γ = 73.903 (9)° | Block, pale yellow |
V = 1173.34 (19) Å3 | 0.42 × 0.34 × 0.32 mm |
Data collection top
Xcalibur, Eos, Gemini diffractometer | 4780 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2796 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ω scans | θmax = 26.4°, θmin = 2.9° |
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb 1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | h = −10→10 |
Tmin = 0.971, Tmax = 0.978 | k = −12→11 |
8002 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.059 | H-atom parameters constrained |
wR(F2) = 0.158 | w = 1/[σ2(Fo2) + (0.061P)2 + 0.0759P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.005 |
4780 reflections | Δρmax = 0.25 e Å−3 |
271 parameters | Δρmin = −0.16 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | −0.0374 (2) | 1.0484 (2) | 0.22265 (13) | 0.0429 (5) | |
C2 | 0.0572 (2) | 1.0010 (2) | 0.13981 (14) | 0.0454 (5) | |
H2 | 0.0504 | 1.0577 | 0.0811 | 0.054* | |
C3 | 0.1588 (2) | 0.8745 (2) | 0.14267 (13) | 0.0450 (5) | |
H3 | 0.2183 | 0.8465 | 0.0859 | 0.054* | |
C4 | 0.1751 (2) | 0.7862 (2) | 0.22965 (13) | 0.0449 (5) | |
C5 | 0.0834 (3) | 0.8332 (2) | 0.31276 (14) | 0.0520 (6) | |
H5 | 0.0921 | 0.7770 | 0.3718 | 0.062* | |
C6 | −0.0187 (3) | 0.9599 (2) | 0.30956 (14) | 0.0511 (5) | |
H6 | −0.0774 | 0.9879 | 0.3666 | 0.061* | |
C7 | −0.1462 (2) | 1.1801 (2) | 0.21789 (14) | 0.0486 (5) | |
C8 | −0.2319 (3) | 1.2327 (2) | 0.30279 (17) | 0.0582 (6) | |
C9 | −0.1675 (3) | 1.2633 (2) | 0.12842 (17) | 0.0592 (6) | |
C10 | 0.2735 (2) | 0.6475 (2) | 0.23155 (14) | 0.0465 (5) | |
C11 | 0.4196 (3) | 0.6444 (2) | 0.38231 (14) | 0.0628 (7) | |
H11A | 0.4115 | 0.6025 | 0.4494 | 0.075* | |
H11B | 0.3646 | 0.7397 | 0.3817 | 0.075* | |
C12 | 0.5904 (3) | 0.6281 (2) | 0.35371 (16) | 0.0683 (7) | |
H12A | 0.6367 | 0.6717 | 0.3997 | 0.082* | |
H12B | 0.6464 | 0.5328 | 0.3594 | 0.082* | |
C13 | 0.5784 (3) | 0.8314 (3) | 0.24415 (19) | 0.0787 (8) | |
H13A | 0.6553 | 0.8563 | 0.2817 | 0.094* | |
H13B | 0.4742 | 0.8704 | 0.2727 | 0.094* | |
C14 | 0.5851 (4) | 0.8875 (3) | 0.1377 (2) | 0.0948 (9) | |
H14A | 0.5680 | 0.9845 | 0.1349 | 0.114* | |
H14B | 0.5012 | 0.8704 | 0.1016 | 0.114* | |
C15 | 0.7426 (4) | 0.8250 (4) | 0.0881 (2) | 0.0979 (10) | |
H15A | 0.7386 | 0.8537 | 0.0173 | 0.117* | |
H15B | 0.8248 | 0.8551 | 0.1162 | 0.117* | |
C16 | 0.7808 (4) | 0.6736 (4) | 0.1037 (2) | 0.1061 (11) | |
H16A | 0.8873 | 0.6345 | 0.0787 | 0.127* | |
H16B | 0.7083 | 0.6430 | 0.0662 | 0.127* | |
C17 | 0.7683 (3) | 0.6253 (3) | 0.2125 (2) | 0.0867 (9) | |
H17A | 0.7899 | 0.5277 | 0.2199 | 0.104* | |
H17B | 0.8464 | 0.6495 | 0.2495 | 0.104* | |
C18 | 0.3939 (3) | 0.4551 (2) | 0.13282 (15) | 0.0599 (6) | |
H18A | 0.4900 | 0.4471 | 0.1681 | 0.072* | |
H18B | 0.4209 | 0.4560 | 0.0622 | 0.072* | |
C19 | 0.3369 (3) | 0.3329 (2) | 0.16403 (15) | 0.0676 (7) | |
H19A | 0.2400 | 0.3410 | 0.1297 | 0.081* | |
H19B | 0.4154 | 0.2535 | 0.1436 | 0.081* | |
C20 | 0.1396 (3) | 0.3632 (2) | 0.29706 (17) | 0.0652 (6) | |
H20A | 0.0818 | 0.3103 | 0.2673 | 0.078* | |
H20B | 0.1003 | 0.4565 | 0.2698 | 0.078* | |
C21 | 0.1108 (3) | 0.3539 (3) | 0.40868 (18) | 0.0798 (8) | |
H21A | 0.1629 | 0.4114 | 0.4382 | 0.096* | |
H21B | −0.0018 | 0.3854 | 0.4234 | 0.096* | |
C22 | 0.1729 (4) | 0.2115 (3) | 0.45301 (19) | 0.0865 (9) | |
H22A | 0.1096 | 0.1567 | 0.4316 | 0.104* | |
H22B | 0.1645 | 0.2088 | 0.5251 | 0.104* | |
C23 | 0.3432 (4) | 0.1543 (3) | 0.42152 (17) | 0.0818 (8) | |
H23A | 0.3769 | 0.0588 | 0.4440 | 0.098* | |
H23B | 0.4088 | 0.1989 | 0.4531 | 0.098* | |
C24 | 0.3668 (3) | 0.1724 (2) | 0.30946 (16) | 0.0662 (7) | |
H24A | 0.4786 | 0.1407 | 0.2924 | 0.079* | |
H24B | 0.3119 | 0.1187 | 0.2781 | 0.079* | |
N1 | −0.2989 (3) | 1.2740 (2) | 0.37300 (17) | 0.0897 (8) | |
N2 | −0.1808 (3) | 1.3275 (2) | 0.05323 (15) | 0.0895 (8) | |
N3 | 0.3458 (2) | 0.58211 (17) | 0.31300 (11) | 0.0535 (5) | |
H3A | 0.3495 | 0.4982 | 0.3258 | 0.064* | |
N4 | 0.6107 (2) | 0.68575 (18) | 0.25270 (13) | 0.0565 (5) | |
N5 | 0.2814 (2) | 0.58337 (17) | 0.15090 (11) | 0.0517 (5) | |
H5A | 0.2143 | 0.6206 | 0.1052 | 0.062* | |
N6 | 0.3069 (2) | 0.31415 (16) | 0.27187 (11) | 0.0489 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0453 (13) | 0.0423 (12) | 0.0450 (11) | −0.0184 (10) | 0.0020 (9) | −0.0056 (9) |
C2 | 0.0539 (13) | 0.0427 (12) | 0.0401 (10) | −0.0159 (10) | 0.0012 (9) | −0.0006 (9) |
C3 | 0.0506 (13) | 0.0443 (12) | 0.0401 (10) | −0.0143 (10) | 0.0062 (9) | −0.0043 (9) |
C4 | 0.0504 (13) | 0.0415 (12) | 0.0416 (11) | −0.0131 (10) | 0.0037 (9) | 0.0002 (9) |
C5 | 0.0607 (15) | 0.0480 (13) | 0.0441 (11) | −0.0143 (12) | 0.0099 (10) | 0.0037 (10) |
C6 | 0.0553 (14) | 0.0502 (13) | 0.0474 (12) | −0.0159 (11) | 0.0124 (10) | −0.0050 (10) |
C7 | 0.0505 (14) | 0.0449 (12) | 0.0492 (12) | −0.0098 (11) | −0.0005 (10) | −0.0086 (10) |
C8 | 0.0583 (15) | 0.0486 (14) | 0.0655 (14) | −0.0110 (12) | 0.0045 (12) | −0.0089 (12) |
C9 | 0.0694 (16) | 0.0457 (14) | 0.0549 (14) | 0.0024 (12) | −0.0100 (11) | −0.0161 (11) |
C10 | 0.0563 (14) | 0.0418 (12) | 0.0406 (11) | −0.0155 (11) | 0.0056 (9) | 0.0029 (9) |
C11 | 0.089 (2) | 0.0550 (14) | 0.0378 (11) | −0.0081 (13) | −0.0089 (11) | −0.0022 (10) |
C12 | 0.081 (2) | 0.0554 (15) | 0.0612 (14) | −0.0013 (13) | −0.0276 (13) | −0.0082 (11) |
C13 | 0.077 (2) | 0.0580 (17) | 0.0947 (19) | −0.0093 (14) | 0.0126 (15) | −0.0116 (14) |
C14 | 0.090 (2) | 0.085 (2) | 0.109 (2) | −0.0342 (19) | 0.0106 (18) | 0.0142 (17) |
C15 | 0.093 (2) | 0.130 (3) | 0.094 (2) | −0.069 (2) | 0.0180 (17) | −0.021 (2) |
C16 | 0.095 (3) | 0.126 (3) | 0.109 (3) | −0.042 (2) | 0.0354 (19) | −0.048 (2) |
C17 | 0.066 (2) | 0.077 (2) | 0.114 (2) | −0.0063 (15) | 0.0021 (16) | −0.0365 (17) |
C18 | 0.0763 (17) | 0.0506 (14) | 0.0448 (12) | −0.0062 (12) | 0.0106 (11) | −0.0049 (10) |
C19 | 0.103 (2) | 0.0474 (14) | 0.0500 (13) | −0.0157 (14) | 0.0006 (12) | −0.0077 (11) |
C20 | 0.0600 (17) | 0.0604 (15) | 0.0749 (16) | −0.0155 (13) | −0.0120 (12) | −0.0023 (12) |
C21 | 0.0629 (18) | 0.096 (2) | 0.0850 (18) | −0.0310 (17) | 0.0184 (14) | −0.0136 (16) |
C22 | 0.100 (2) | 0.102 (2) | 0.0688 (16) | −0.053 (2) | 0.0063 (15) | 0.0043 (16) |
C23 | 0.112 (3) | 0.0641 (17) | 0.0661 (16) | −0.0236 (17) | −0.0220 (15) | 0.0157 (13) |
C24 | 0.0847 (19) | 0.0428 (13) | 0.0656 (14) | −0.0082 (13) | −0.0128 (13) | 0.0005 (11) |
N1 | 0.0970 (19) | 0.0830 (17) | 0.0848 (15) | −0.0157 (14) | 0.0296 (14) | −0.0285 (13) |
N2 | 0.128 (2) | 0.0617 (15) | 0.0560 (12) | 0.0143 (14) | −0.0160 (13) | −0.0060 (11) |
N3 | 0.0768 (14) | 0.0411 (10) | 0.0413 (9) | −0.0173 (10) | −0.0019 (9) | 0.0055 (8) |
N4 | 0.0536 (12) | 0.0535 (12) | 0.0603 (11) | −0.0072 (9) | −0.0064 (9) | −0.0133 (9) |
N5 | 0.0640 (13) | 0.0443 (10) | 0.0421 (9) | −0.0082 (9) | −0.0009 (8) | −0.0010 (8) |
N6 | 0.0566 (12) | 0.0387 (10) | 0.0476 (9) | −0.0074 (9) | −0.0028 (8) | −0.0013 (8) |
Geometric parameters (Å, º) top
C1—C6 | 1.399 (3) | C15—H15A | 0.9700 |
C1—C2 | 1.405 (3) | C15—H15B | 0.9700 |
C1—C7 | 1.429 (3) | C16—C17 | 1.509 (4) |
C2—C3 | 1.363 (3) | C16—H16A | 0.9700 |
C2—H2 | 0.9300 | C16—H16B | 0.9700 |
C3—C4 | 1.399 (3) | C17—N4 | 1.456 (3) |
C3—H3 | 0.9300 | C17—H17A | 0.9700 |
C4—C5 | 1.394 (3) | C17—H17B | 0.9700 |
C4—C10 | 1.455 (3) | C18—N5 | 1.454 (3) |
C5—C6 | 1.366 (3) | C18—C19 | 1.500 (3) |
C5—H5 | 0.9300 | C18—H18A | 0.9700 |
C6—H6 | 0.9300 | C18—H18B | 0.9700 |
C7—C9 | 1.397 (3) | C19—N6 | 1.468 (2) |
C7—C8 | 1.409 (3) | C19—H19A | 0.9700 |
C8—N1 | 1.146 (3) | C19—H19B | 0.9700 |
C9—N2 | 1.147 (3) | C20—N6 | 1.452 (3) |
C10—N5 | 1.321 (2) | C20—C21 | 1.511 (3) |
C10—N3 | 1.323 (2) | C20—H20A | 0.9700 |
C11—N3 | 1.460 (3) | C20—H20B | 0.9700 |
C11—C12 | 1.499 (3) | C21—C22 | 1.495 (4) |
C11—H11A | 0.9700 | C21—H21A | 0.9700 |
C11—H11B | 0.9700 | C21—H21B | 0.9700 |
C12—N4 | 1.453 (3) | C22—C23 | 1.507 (4) |
C12—H12A | 0.9700 | C22—H22A | 0.9700 |
C12—H12B | 0.9700 | C22—H22B | 0.9700 |
C13—N4 | 1.447 (3) | C23—C24 | 1.514 (3) |
C13—C14 | 1.497 (3) | C23—H23A | 0.9700 |
C13—H13A | 0.9700 | C23—H23B | 0.9700 |
C13—H13B | 0.9700 | C24—N6 | 1.461 (3) |
C14—C15 | 1.510 (4) | C24—H24A | 0.9700 |
C14—H14A | 0.9700 | C24—H24B | 0.9700 |
C14—H14B | 0.9700 | N3—H3A | 0.8600 |
C15—C16 | 1.504 (4) | N5—H5A | 0.8600 |
| | | |
C6—C1—C2 | 116.28 (19) | H16A—C16—H16B | 108.0 |
C6—C1—C7 | 122.19 (17) | N4—C17—C16 | 110.4 (2) |
C2—C1—C7 | 121.54 (18) | N4—C17—H17A | 109.6 |
C3—C2—C1 | 122.13 (18) | C16—C17—H17A | 109.6 |
C3—C2—H2 | 118.9 | N4—C17—H17B | 109.6 |
C1—C2—H2 | 118.9 | C16—C17—H17B | 109.6 |
C2—C3—C4 | 121.06 (18) | H17A—C17—H17B | 108.1 |
C2—C3—H3 | 119.5 | N5—C18—C19 | 114.91 (19) |
C4—C3—H3 | 119.5 | N5—C18—H18A | 108.5 |
C5—C4—C3 | 117.21 (19) | C19—C18—H18A | 108.5 |
C5—C4—C10 | 121.01 (17) | N5—C18—H18B | 108.5 |
C3—C4—C10 | 121.60 (17) | C19—C18—H18B | 108.5 |
C6—C5—C4 | 121.59 (19) | H18A—C18—H18B | 107.5 |
C6—C5—H5 | 119.2 | N6—C19—C18 | 113.25 (17) |
C4—C5—H5 | 119.2 | N6—C19—H19A | 108.9 |
C5—C6—C1 | 121.71 (18) | C18—C19—H19A | 108.9 |
C5—C6—H6 | 119.1 | N6—C19—H19B | 108.9 |
C1—C6—H6 | 119.1 | C18—C19—H19B | 108.9 |
C9—C7—C8 | 117.6 (2) | H19A—C19—H19B | 107.7 |
C9—C7—C1 | 120.59 (18) | N6—C20—C21 | 111.23 (19) |
C8—C7—C1 | 121.83 (18) | N6—C20—H20A | 109.4 |
N1—C8—C7 | 178.6 (3) | C21—C20—H20A | 109.4 |
N2—C9—C7 | 177.3 (3) | N6—C20—H20B | 109.4 |
N5—C10—N3 | 119.60 (19) | C21—C20—H20B | 109.4 |
N5—C10—C4 | 118.21 (18) | H20A—C20—H20B | 108.0 |
N3—C10—C4 | 122.04 (18) | C22—C21—C20 | 110.6 (2) |
N3—C11—C12 | 110.41 (17) | C22—C21—H21A | 109.5 |
N3—C11—H11A | 109.6 | C20—C21—H21A | 109.5 |
C12—C11—H11A | 109.6 | C22—C21—H21B | 109.5 |
N3—C11—H11B | 109.6 | C20—C21—H21B | 109.5 |
C12—C11—H11B | 109.6 | H21A—C21—H21B | 108.1 |
H11A—C11—H11B | 108.1 | C21—C22—C23 | 110.7 (2) |
N4—C12—C11 | 112.23 (18) | C21—C22—H22A | 109.5 |
N4—C12—H12A | 109.2 | C23—C22—H22A | 109.5 |
C11—C12—H12A | 109.2 | C21—C22—H22B | 109.5 |
N4—C12—H12B | 109.2 | C23—C22—H22B | 109.5 |
C11—C12—H12B | 109.2 | H22A—C22—H22B | 108.1 |
H12A—C12—H12B | 107.9 | C22—C23—C24 | 111.8 (2) |
N4—C13—C14 | 111.5 (2) | C22—C23—H23A | 109.3 |
N4—C13—H13A | 109.3 | C24—C23—H23A | 109.3 |
C14—C13—H13A | 109.3 | C22—C23—H23B | 109.3 |
N4—C13—H13B | 109.3 | C24—C23—H23B | 109.3 |
C14—C13—H13B | 109.3 | H23A—C23—H23B | 107.9 |
H13A—C13—H13B | 108.0 | N6—C24—C23 | 110.84 (18) |
C13—C14—C15 | 111.5 (3) | N6—C24—H24A | 109.5 |
C13—C14—H14A | 109.3 | C23—C24—H24A | 109.5 |
C15—C14—H14A | 109.3 | N6—C24—H24B | 109.5 |
C13—C14—H14B | 109.3 | C23—C24—H24B | 109.5 |
C15—C14—H14B | 109.3 | H24A—C24—H24B | 108.1 |
H14A—C14—H14B | 108.0 | C10—N3—C11 | 123.69 (17) |
C16—C15—C14 | 109.9 (2) | C10—N3—H3A | 118.2 |
C16—C15—H15A | 109.7 | C11—N3—H3A | 118.2 |
C14—C15—H15A | 109.7 | C13—N4—C12 | 113.35 (18) |
C16—C15—H15B | 109.7 | C13—N4—C17 | 110.1 (2) |
C14—C15—H15B | 109.7 | C12—N4—C17 | 111.2 (2) |
H15A—C15—H15B | 108.2 | C10—N5—C18 | 125.53 (18) |
C15—C16—C17 | 111.5 (2) | C10—N5—H5A | 117.2 |
C15—C16—H16A | 109.3 | C18—N5—H5A | 117.2 |
C17—C16—H16A | 109.3 | C20—N6—C24 | 110.12 (18) |
C15—C16—H16B | 109.3 | C20—N6—C19 | 111.45 (18) |
C17—C16—H16B | 109.3 | C24—N6—C19 | 110.93 (16) |
Crystal data top
C24H22N6 | Dx = 1.241 Mg m−3 |
Mr = 394.47 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 536 reflections |
a = 8.2134 (11) Å | θ = 3.4–20.6° |
b = 12.2105 (11) Å | µ = 0.08 mm−1 |
c = 21.052 (3) Å | T = 293 K |
V = 2111.3 (4) Å3 | Plate, pale brown |
Z = 4 | 0.32 × 0.24 × 0.12 mm |
F(000) = 832 | |
Data collection top
Xcalibur, Eos, Gemini diffractometer | 4005 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2093 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
ω scans | θmax = 26.4°, θmin = 2.7° |
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb 1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | h = −4→10 |
Tmin = 0.976, Tmax = 0.991 | k = −9→15 |
5955 measured reflections | l = −26→15 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.071 | w = 1/[σ2(Fo2) + (0.0233P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.123 | (Δ/σ)max = 0.008 |
S = 0.95 | Δρmax = 0.17 e Å−3 |
4005 reflections | Δρmin = −0.18 e Å−3 |
271 parameters | Absolute structure: Flack x determined using 529 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61). |
0 restraints | Absolute structure parameter: −2.7 (10) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.5301 (7) | 0.4747 (3) | 0.6105 (2) | 0.0336 (12) | |
C2 | 0.4614 (7) | 0.4895 (4) | 0.5501 (2) | 0.0392 (13) | |
H2 | 0.3496 | 0.4808 | 0.5450 | 0.047* | |
C3 | 0.5552 (7) | 0.5165 (4) | 0.4981 (2) | 0.0397 (14) | |
H3 | 0.5064 | 0.5248 | 0.4585 | 0.048* | |
C4 | 0.7213 (7) | 0.5313 (4) | 0.5044 (2) | 0.0337 (13) | |
C5 | 0.7932 (7) | 0.5145 (3) | 0.5636 (2) | 0.0376 (13) | |
H5 | 0.9051 | 0.5224 | 0.5684 | 0.045* | |
C6 | 0.6984 (7) | 0.4861 (4) | 0.6151 (2) | 0.0407 (14) | |
H6 | 0.7484 | 0.4743 | 0.6542 | 0.049* | |
C7 | 0.4280 (7) | 0.4473 (4) | 0.6641 (3) | 0.0393 (14) | |
C8 | 0.4965 (7) | 0.4215 (4) | 0.7232 (3) | 0.0427 (15) | |
C9 | 0.2613 (9) | 0.4381 (5) | 0.6582 (3) | 0.0509 (17) | |
C10 | 0.8197 (7) | 0.5706 (4) | 0.4508 (2) | 0.0342 (12) | |
C11 | 1.0455 (7) | 0.6969 (4) | 0.4195 (2) | 0.0410 (14) | |
H11A | 1.0741 | 0.7709 | 0.4320 | 0.049* | |
H11B | 1.0042 | 0.6993 | 0.3764 | 0.049* | |
C12 | 1.1938 (7) | 0.6258 (4) | 0.4220 (3) | 0.0528 (16) | |
H12A | 1.1658 | 0.5537 | 0.4061 | 0.063* | |
H12B | 1.2272 | 0.6178 | 0.4659 | 0.063* | |
C13 | 1.3351 (7) | 0.6692 (4) | 0.3842 (3) | 0.0411 (13) | |
C14 | 1.3696 (8) | 0.6335 (5) | 0.3231 (3) | 0.0588 (18) | |
H14 | 1.3029 | 0.5823 | 0.3033 | 0.071* | |
C15 | 1.5030 (10) | 0.6747 (6) | 0.2923 (3) | 0.073 (2) | |
H15 | 1.5268 | 0.6521 | 0.2511 | 0.088* | |
C16 | 1.6006 (8) | 0.7483 (5) | 0.3219 (3) | 0.0651 (19) | |
H16 | 1.6928 | 0.7761 | 0.3019 | 0.078* | |
C17 | 1.5592 (8) | 0.7807 (4) | 0.3820 (3) | 0.0535 (16) | |
H17 | 1.6247 | 0.8323 | 0.4020 | 0.064* | |
C18 | 0.7317 (7) | 0.4234 (4) | 0.3780 (2) | 0.0503 (15) | |
H18A | 0.6318 | 0.4357 | 0.3545 | 0.060* | |
H18B | 0.7045 | 0.3852 | 0.4170 | 0.060* | |
C19 | 0.8465 (8) | 0.3534 (4) | 0.3386 (3) | 0.0561 (18) | |
H19A | 0.7950 | 0.2833 | 0.3303 | 0.067* | |
H19B | 0.8650 | 0.3890 | 0.2981 | 0.067* | |
C20 | 1.0068 (9) | 0.3340 (4) | 0.3703 (3) | 0.0538 (18) | |
C21 | 1.1451 (11) | 0.3258 (5) | 0.3349 (4) | 0.087 (3) | |
H21 | 1.1416 | 0.3349 | 0.2910 | 0.104* | |
C22 | 1.2902 (14) | 0.3038 (8) | 0.3652 (6) | 0.126 (5) | |
H22 | 1.3855 | 0.2966 | 0.3417 | 0.151* | |
C23 | 1.2936 (15) | 0.2928 (6) | 0.4289 (6) | 0.119 (4) | |
H23 | 1.3899 | 0.2779 | 0.4504 | 0.142* | |
C24 | 1.1484 (13) | 0.3046 (6) | 0.4607 (4) | 0.096 (3) | |
H24 | 1.1501 | 0.2983 | 0.5047 | 0.116* | |
N1 | 0.5540 (7) | 0.3992 (4) | 0.7715 (2) | 0.0621 (15) | |
N2 | 0.1223 (7) | 0.4308 (5) | 0.6515 (3) | 0.0822 (19) | |
N3 | 0.9188 (5) | 0.6550 (3) | 0.46196 (18) | 0.0381 (11) | |
H3A | 0.9071 | 0.6881 | 0.4977 | 0.046* | |
N4 | 1.4309 (6) | 0.7425 (3) | 0.4133 (2) | 0.0441 (12) | |
N5 | 0.8069 (6) | 0.5288 (3) | 0.39332 (17) | 0.0398 (11) | |
H5A | 0.8458 | 0.5665 | 0.3623 | 0.048* | |
N6 | 1.0051 (8) | 0.3245 (4) | 0.4330 (3) | 0.0757 (18) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.036 (3) | 0.035 (3) | 0.030 (3) | 0.000 (3) | 0.000 (3) | 0.004 (2) |
C2 | 0.032 (3) | 0.046 (3) | 0.040 (3) | −0.001 (3) | −0.004 (3) | 0.006 (3) |
C3 | 0.042 (4) | 0.042 (3) | 0.035 (3) | 0.000 (3) | −0.005 (3) | 0.007 (3) |
C4 | 0.034 (3) | 0.038 (3) | 0.030 (3) | 0.000 (3) | 0.001 (3) | −0.002 (2) |
C5 | 0.031 (3) | 0.044 (3) | 0.038 (3) | −0.005 (3) | −0.003 (3) | 0.004 (2) |
C6 | 0.045 (4) | 0.046 (3) | 0.031 (3) | 0.000 (3) | −0.008 (3) | 0.008 (3) |
C7 | 0.038 (4) | 0.047 (3) | 0.032 (3) | 0.000 (3) | 0.000 (3) | 0.005 (2) |
C8 | 0.045 (4) | 0.050 (3) | 0.033 (3) | −0.006 (3) | 0.007 (3) | −0.002 (3) |
C9 | 0.049 (4) | 0.063 (4) | 0.040 (4) | 0.006 (3) | 0.007 (4) | 0.021 (3) |
C10 | 0.034 (3) | 0.036 (3) | 0.033 (3) | 0.007 (3) | 0.002 (3) | −0.002 (2) |
C11 | 0.046 (4) | 0.041 (3) | 0.035 (3) | −0.004 (3) | 0.005 (3) | −0.003 (2) |
C12 | 0.047 (4) | 0.053 (3) | 0.059 (4) | 0.003 (3) | 0.006 (4) | 0.009 (3) |
C13 | 0.034 (3) | 0.048 (3) | 0.042 (3) | 0.005 (3) | 0.001 (3) | 0.002 (3) |
C14 | 0.050 (5) | 0.082 (4) | 0.044 (4) | −0.014 (4) | −0.003 (4) | −0.016 (3) |
C15 | 0.073 (6) | 0.107 (5) | 0.039 (4) | −0.002 (5) | 0.010 (4) | −0.019 (4) |
C16 | 0.051 (5) | 0.089 (5) | 0.055 (4) | −0.008 (4) | 0.013 (4) | 0.001 (4) |
C17 | 0.051 (4) | 0.049 (3) | 0.061 (4) | −0.011 (3) | −0.001 (4) | −0.006 (3) |
C18 | 0.052 (4) | 0.050 (3) | 0.049 (3) | −0.013 (3) | 0.000 (4) | −0.010 (3) |
C19 | 0.069 (5) | 0.052 (3) | 0.048 (4) | −0.005 (3) | 0.004 (4) | −0.017 (3) |
C20 | 0.055 (5) | 0.041 (3) | 0.066 (5) | −0.007 (3) | 0.004 (4) | −0.016 (3) |
C21 | 0.070 (6) | 0.085 (5) | 0.105 (6) | −0.011 (5) | 0.012 (6) | −0.052 (5) |
C22 | 0.067 (7) | 0.118 (7) | 0.193 (12) | −0.008 (6) | 0.018 (10) | −0.090 (9) |
C23 | 0.073 (7) | 0.063 (5) | 0.220 (13) | 0.002 (5) | −0.036 (11) | −0.021 (7) |
C24 | 0.099 (7) | 0.077 (5) | 0.113 (7) | −0.017 (6) | −0.037 (7) | 0.028 (5) |
N1 | 0.064 (4) | 0.088 (3) | 0.034 (3) | −0.009 (3) | −0.004 (3) | 0.007 (3) |
N2 | 0.046 (4) | 0.129 (5) | 0.072 (4) | 0.001 (4) | −0.003 (4) | 0.046 (4) |
N3 | 0.043 (3) | 0.043 (2) | 0.029 (2) | −0.006 (2) | 0.005 (2) | −0.0062 (19) |
N4 | 0.046 (3) | 0.046 (2) | 0.041 (3) | −0.003 (3) | 0.007 (3) | 0.000 (2) |
N5 | 0.052 (3) | 0.037 (2) | 0.030 (2) | −0.007 (2) | 0.002 (3) | −0.0056 (19) |
N6 | 0.079 (5) | 0.075 (4) | 0.072 (4) | −0.009 (4) | −0.011 (4) | 0.016 (3) |
Geometric parameters (Å, º) top
C1—C6 | 1.393 (7) | C12—C13 | 1.502 (7) |
C1—C2 | 1.403 (6) | C13—N4 | 1.339 (6) |
C1—C7 | 1.445 (7) | C13—C14 | 1.389 (7) |
C2—C3 | 1.378 (6) | C14—C15 | 1.369 (8) |
C3—C4 | 1.383 (7) | C15—C16 | 1.356 (8) |
C4—C5 | 1.395 (6) | C16—C17 | 1.367 (7) |
C4—C10 | 1.468 (6) | C17—N4 | 1.328 (7) |
C5—C6 | 1.379 (6) | C18—N5 | 1.463 (5) |
C7—C9 | 1.379 (9) | C18—C19 | 1.519 (7) |
C7—C8 | 1.401 (7) | C19—C20 | 1.495 (8) |
C8—N1 | 1.154 (6) | C20—N6 | 1.324 (8) |
C9—N2 | 1.154 (8) | C20—C21 | 1.362 (9) |
C10—N5 | 1.317 (5) | C21—C22 | 1.378 (12) |
C10—N3 | 1.334 (6) | C22—C23 | 1.349 (12) |
C11—N3 | 1.464 (6) | C23—C24 | 1.374 (12) |
C11—C12 | 1.497 (7) | C24—N6 | 1.336 (10) |
| | | |
C6—C1—C2 | 116.7 (5) | N4—C13—C14 | 120.9 (5) |
C6—C1—C7 | 123.0 (5) | N4—C13—C12 | 116.6 (5) |
C2—C1—C7 | 120.3 (5) | C14—C13—C12 | 122.5 (5) |
C3—C2—C1 | 121.7 (5) | C15—C14—C13 | 119.2 (6) |
C2—C3—C4 | 120.5 (5) | C16—C15—C14 | 119.9 (6) |
C3—C4—C5 | 118.9 (5) | C15—C16—C17 | 118.0 (6) |
C3—C4—C10 | 120.8 (5) | N4—C17—C16 | 123.7 (6) |
C5—C4—C10 | 120.2 (5) | N5—C18—C19 | 110.7 (5) |
C6—C5—C4 | 120.1 (5) | C20—C19—C18 | 113.1 (5) |
C5—C6—C1 | 122.0 (5) | N6—C20—C21 | 123.2 (8) |
C9—C7—C8 | 117.4 (6) | N6—C20—C19 | 116.6 (7) |
C9—C7—C1 | 121.6 (6) | C21—C20—C19 | 120.1 (7) |
C8—C7—C1 | 120.8 (5) | C20—C21—C22 | 118.8 (9) |
N1—C8—C7 | 179.1 (6) | C23—C22—C21 | 119.9 (13) |
N2—C9—C7 | 178.1 (8) | C22—C23—C24 | 117.1 (13) |
N5—C10—N3 | 120.7 (5) | N6—C24—C23 | 124.8 (9) |
N5—C10—C4 | 122.4 (5) | C10—N3—C11 | 126.6 (4) |
N3—C10—C4 | 116.9 (4) | C17—N4—C13 | 118.3 (5) |
N3—C11—C12 | 110.8 (4) | C10—N5—C18 | 125.2 (4) |
C11—C12—C13 | 113.9 (4) | C20—N6—C24 | 116.2 (7) |
Crystal data top
C22H30N6 | F(000) = 816 |
Mr = 378.52 | Dx = 1.168 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.1430 (12) Å | Cell parameters from 7115 reflections |
b = 10.3517 (9) Å | θ = 2.4–25.5° |
c = 16.1607 (15) Å | µ = 0.07 mm−1 |
β = 101.651 (1)° | T = 293 K |
V = 2153.4 (3) Å3 | Plate, pale yellow |
Z = 4 | 0.32 × 0.18 × 0.12 mm |
Data collection top
CCD area detector diffractometer | 4206 independent reflections |
Radiation source: sealed tube | 2879 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
phi and ω scans | θmax = 26.0°, θmin = 1.6° |
Absorption correction: multi-scan sadabs | h = −16→16 |
Tmin = 0.972, Tmax = 0.982 | k = −12→12 |
21689 measured reflections | l = −19→19 |
Refinement top
Refinement on F2 | 1 restraint |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.157 | w = 1/[σ2(Fo2) + (0.0841P)2 + 0.2303P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
4206 reflections | Δρmax = 0.16 e Å−3 |
253 parameters | Δρmin = −0.18 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 1.09780 (12) | 0.08555 (15) | 0.74299 (10) | 0.0517 (4) | |
C2 | 1.03813 (13) | 0.19874 (15) | 0.72666 (10) | 0.0565 (4) | |
H2 | 1.0515 | 0.2672 | 0.7646 | 0.068* | |
C3 | 0.96114 (13) | 0.21071 (15) | 0.65658 (10) | 0.0573 (4) | |
H3 | 0.9235 | 0.2873 | 0.6477 | 0.069* | |
C4 | 0.93754 (12) | 0.11085 (15) | 0.59788 (10) | 0.0530 (4) | |
C5 | 0.99641 (13) | −0.00194 (15) | 0.61344 (10) | 0.0557 (4) | |
H5 | 0.9824 | −0.0704 | 0.5756 | 0.067* | |
C6 | 1.07419 (13) | −0.01392 (15) | 0.68318 (11) | 0.0553 (4) | |
H6 | 1.1125 | −0.0900 | 0.6913 | 0.066* | |
C7 | 1.17782 (13) | 0.07278 (15) | 0.81767 (11) | 0.0581 (4) | |
C8 | 1.19386 (15) | 0.17185 (18) | 0.87777 (12) | 0.0692 (5) | |
C9 | 1.24025 (14) | −0.03791 (19) | 0.83272 (12) | 0.0671 (5) | |
C10 | 0.84906 (13) | 0.12057 (16) | 0.52686 (10) | 0.0546 (4) | |
C11 | 0.89483 (15) | 0.33843 (18) | 0.48346 (11) | 0.0678 (5) | |
H11A | 0.9650 | 0.3136 | 0.5100 | 0.081* | |
H11B | 0.8737 | 0.4085 | 0.5161 | 0.081* | |
C12 | 0.89369 (14) | 0.38437 (17) | 0.39536 (11) | 0.0644 (5) | |
H12A | 0.9490 | 0.4469 | 0.3969 | 0.077* | |
H12B | 0.9078 | 0.3117 | 0.3615 | 0.077* | |
C13 | 0.77946 (19) | 0.5709 (2) | 0.38667 (14) | 0.0870 (6) | |
H13A | 0.8441 | 0.6190 | 0.3994 | 0.104* | |
H13B | 0.7511 | 0.5652 | 0.4375 | 0.104* | |
C14 | 0.7033 (2) | 0.6350 (2) | 0.31651 (18) | 0.1098 (8) | |
H14A | 0.6348 | 0.6384 | 0.3302 | 0.132* | |
H14B | 0.7254 | 0.7224 | 0.3074 | 0.132* | |
C15 | 0.7014 (2) | 0.5539 (3) | 0.23924 (16) | 0.1098 (8) | |
H15A | 0.6361 | 0.5079 | 0.2236 | 0.132* | |
H15B | 0.7112 | 0.6069 | 0.1920 | 0.132* | |
C16 | 0.78976 (17) | 0.4620 (2) | 0.26457 (12) | 0.0779 (6) | |
H16A | 0.7760 | 0.3810 | 0.2342 | 0.093* | |
H16B | 0.8538 | 0.4984 | 0.2537 | 0.093* | |
C17 | 0.70982 (16) | −0.0019 (2) | 0.43182 (14) | 0.0828 (6) | |
H17A | 0.6996 | −0.0938 | 0.4217 | 0.099* | |
H17B | 0.7326 | 0.0348 | 0.3834 | 0.099* | |
C18 | 0.60789 (16) | 0.0581 (3) | 0.43856 (16) | 0.0967 (7) | |
H18A | 0.5526 | 0.0160 | 0.3989 | 0.116* | |
H18B | 0.5955 | 0.0438 | 0.4950 | 0.116* | |
C19 | 0.5722 (2) | 0.2275 (3) | 0.33234 (17) | 0.1097 (9) | |
H19A | 0.5345 | 0.1560 | 0.3015 | 0.132* | |
H19B | 0.6321 | 0.2467 | 0.3079 | 0.132* | |
C20 | 0.5037 (3) | 0.3432 (4) | 0.3279 (3) | 0.1646 (16) | |
H20A | 0.5265 | 0.4105 | 0.2940 | 0.198* | |
H20B | 0.4324 | 0.3209 | 0.3031 | 0.198* | |
C21 | 0.5123 (3) | 0.3862 (4) | 0.4145 (4) | 0.191 (2) | |
H21A | 0.4483 | 0.4265 | 0.4224 | 0.229* | |
H21B | 0.5689 | 0.4473 | 0.4302 | 0.229* | |
C22 | 0.5330 (3) | 0.2659 (4) | 0.4647 (2) | 0.1501 (13) | |
H22A | 0.5652 | 0.2844 | 0.5229 | 0.180* | |
H22B | 0.4695 | 0.2175 | 0.4634 | 0.180* | |
N1 | 1.20299 (18) | 0.25583 (18) | 0.92484 (12) | 0.1015 (7) | |
N2 | 1.28847 (15) | −0.13103 (19) | 0.84314 (13) | 0.1010 (6) | |
N3 | 0.82533 (11) | 0.22851 (13) | 0.48398 (9) | 0.0591 (4) | |
H3A | 0.7637 | 0.2347 | 0.4538 | 0.071* | |
N4 | 0.79633 (11) | 0.44279 (13) | 0.35509 (9) | 0.0600 (4) | |
N5 | 0.79115 (11) | 0.01659 (14) | 0.50634 (10) | 0.0663 (4) | |
H5A | 0.8029 | −0.0473 | 0.5410 | 0.080* | |
N6 | 0.60484 (12) | 0.19482 (19) | 0.42147 (11) | 0.0836 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0549 (9) | 0.0487 (9) | 0.0525 (9) | −0.0040 (7) | 0.0134 (7) | 0.0028 (7) |
C2 | 0.0696 (10) | 0.0481 (9) | 0.0517 (9) | 0.0023 (8) | 0.0119 (8) | −0.0024 (7) |
C3 | 0.0659 (10) | 0.0502 (9) | 0.0561 (10) | 0.0081 (8) | 0.0132 (8) | 0.0037 (7) |
C4 | 0.0579 (9) | 0.0526 (9) | 0.0489 (9) | −0.0003 (7) | 0.0117 (7) | 0.0035 (7) |
C5 | 0.0634 (10) | 0.0508 (9) | 0.0532 (9) | −0.0012 (7) | 0.0127 (8) | −0.0040 (7) |
C6 | 0.0587 (10) | 0.0468 (9) | 0.0596 (10) | 0.0041 (7) | 0.0103 (8) | 0.0001 (7) |
C7 | 0.0629 (10) | 0.0490 (9) | 0.0593 (10) | −0.0017 (8) | 0.0051 (8) | 0.0012 (7) |
C8 | 0.0848 (13) | 0.0571 (11) | 0.0583 (11) | 0.0011 (9) | −0.0031 (9) | 0.0063 (9) |
C9 | 0.0624 (11) | 0.0603 (11) | 0.0718 (12) | −0.0053 (9) | −0.0027 (9) | −0.0004 (9) |
C10 | 0.0558 (9) | 0.0543 (10) | 0.0545 (9) | −0.0006 (7) | 0.0133 (7) | 0.0025 (7) |
C11 | 0.0689 (11) | 0.0614 (11) | 0.0674 (11) | −0.0094 (9) | 0.0003 (9) | 0.0090 (9) |
C12 | 0.0664 (11) | 0.0564 (10) | 0.0706 (11) | −0.0041 (8) | 0.0147 (9) | 0.0055 (8) |
C13 | 0.1006 (16) | 0.0693 (13) | 0.0899 (15) | 0.0094 (11) | 0.0162 (12) | −0.0098 (11) |
C14 | 0.115 (2) | 0.0844 (16) | 0.129 (2) | 0.0318 (14) | 0.0199 (16) | 0.0228 (15) |
C15 | 0.114 (2) | 0.128 (2) | 0.0856 (17) | 0.0247 (17) | 0.0154 (14) | 0.0364 (16) |
C16 | 0.0930 (14) | 0.0794 (13) | 0.0614 (11) | 0.0021 (11) | 0.0160 (10) | 0.0084 (10) |
C17 | 0.0795 (14) | 0.0676 (12) | 0.0904 (15) | −0.0170 (10) | −0.0085 (11) | 0.0013 (10) |
C18 | 0.0653 (13) | 0.1104 (19) | 0.1083 (18) | −0.0213 (12) | 0.0031 (12) | 0.0266 (14) |
C19 | 0.0949 (17) | 0.116 (2) | 0.1028 (19) | −0.0192 (15) | −0.0172 (14) | 0.0185 (15) |
C20 | 0.138 (3) | 0.115 (3) | 0.209 (4) | −0.002 (2) | −0.040 (3) | 0.042 (3) |
C21 | 0.110 (3) | 0.143 (3) | 0.288 (6) | 0.033 (2) | −0.035 (3) | −0.057 (4) |
C22 | 0.093 (2) | 0.201 (4) | 0.151 (3) | 0.023 (2) | 0.0119 (19) | −0.043 (3) |
N1 | 0.1469 (18) | 0.0708 (11) | 0.0713 (11) | 0.0130 (11) | −0.0148 (11) | −0.0117 (9) |
N2 | 0.0875 (13) | 0.0760 (12) | 0.1235 (16) | 0.0184 (10) | −0.0164 (11) | −0.0050 (11) |
N3 | 0.0545 (8) | 0.0574 (8) | 0.0612 (8) | −0.0044 (6) | 0.0015 (6) | 0.0088 (6) |
N4 | 0.0691 (9) | 0.0523 (8) | 0.0573 (8) | −0.0004 (7) | 0.0097 (7) | 0.0026 (6) |
N5 | 0.0682 (9) | 0.0577 (9) | 0.0679 (9) | −0.0084 (7) | 0.0019 (7) | 0.0071 (7) |
N6 | 0.0597 (10) | 0.0955 (13) | 0.0902 (12) | −0.0012 (9) | 0.0021 (9) | −0.0004 (10) |
Geometric parameters (Å, º) top
C1—C6 | 1.403 (2) | C14—H14A | 0.9700 |
C1—C2 | 1.405 (2) | C14—H14B | 0.9700 |
C1—C7 | 1.438 (2) | C15—C16 | 1.493 (3) |
C2—C3 | 1.363 (2) | C15—H15A | 0.9700 |
C2—H2 | 0.9300 | C15—H15B | 0.9700 |
C3—C4 | 1.395 (2) | C16—N4 | 1.461 (2) |
C3—H3 | 0.9300 | C16—H16A | 0.9700 |
C4—C5 | 1.395 (2) | C16—H16B | 0.9700 |
C4—C10 | 1.463 (2) | C17—N5 | 1.452 (2) |
C5—C6 | 1.366 (2) | C17—C18 | 1.500 (3) |
C5—H5 | 0.9300 | C17—H17A | 0.9700 |
C6—H6 | 0.9300 | C17—H17B | 0.9700 |
C7—C8 | 1.399 (3) | C18—N6 | 1.441 (3) |
C7—C9 | 1.402 (3) | C18—H18A | 0.9700 |
C8—N1 | 1.145 (2) | C18—H18B | 0.9700 |
C9—N2 | 1.147 (2) | C19—N6 | 1.457 (3) |
C10—N3 | 1.319 (2) | C19—C20 | 1.490 (4) |
C10—N5 | 1.321 (2) | C19—H19A | 0.9700 |
C11—N3 | 1.460 (2) | C19—H19B | 0.9700 |
C11—C12 | 1.498 (2) | C20—C21 | 1.452 (6) |
C11—H11A | 0.9700 | C20—H20A | 0.9700 |
C11—H11B | 0.9700 | C20—H20B | 0.9700 |
C12—N4 | 1.446 (2) | C21—C22 | 1.481 (6) |
C12—H12A | 0.9700 | C21—H21A | 0.9700 |
C12—H12B | 0.9700 | C21—H21B | 0.9700 |
C13—N4 | 1.454 (2) | C22—N6 | 1.480 (4) |
C13—C14 | 1.507 (3) | C22—H22A | 0.9700 |
C13—H13A | 0.9700 | C22—H22B | 0.9700 |
C13—H13B | 0.9700 | N3—H3A | 0.8600 |
C14—C15 | 1.501 (4) | N5—H5A | 0.8600 |
| | | |
C6—C1—C2 | 116.43 (14) | H15A—C15—H15B | 108.9 |
C6—C1—C7 | 122.22 (14) | N4—C16—C15 | 104.27 (18) |
C2—C1—C7 | 121.35 (14) | N4—C16—H16A | 110.9 |
C3—C2—C1 | 121.62 (15) | C15—C16—H16A | 110.9 |
C3—C2—H2 | 119.2 | N4—C16—H16B | 110.9 |
C1—C2—H2 | 119.2 | C15—C16—H16B | 110.9 |
C2—C3—C4 | 121.56 (15) | H16A—C16—H16B | 108.9 |
C2—C3—H3 | 119.2 | N5—C17—C18 | 113.8 (2) |
C4—C3—H3 | 119.2 | N5—C17—H17A | 108.8 |
C3—C4—C5 | 117.29 (14) | C18—C17—H17A | 108.8 |
C3—C4—C10 | 120.99 (14) | N5—C17—H17B | 108.8 |
C5—C4—C10 | 121.53 (14) | C18—C17—H17B | 108.8 |
C6—C5—C4 | 121.34 (15) | H17A—C17—H17B | 107.7 |
C6—C5—H5 | 119.3 | N6—C18—C17 | 112.53 (17) |
C4—C5—H5 | 119.3 | N6—C18—H18A | 109.1 |
C5—C6—C1 | 121.75 (15) | C17—C18—H18A | 109.1 |
C5—C6—H6 | 119.1 | N6—C18—H18B | 109.1 |
C1—C6—H6 | 119.1 | C17—C18—H18B | 109.1 |
C8—C7—C9 | 118.56 (15) | H18A—C18—H18B | 107.8 |
C8—C7—C1 | 119.83 (15) | N6—C19—C20 | 106.8 (3) |
C9—C7—C1 | 121.61 (15) | N6—C19—H19A | 110.4 |
N1—C8—C7 | 176.8 (2) | C20—C19—H19A | 110.4 |
N2—C9—C7 | 177.5 (2) | N6—C19—H19B | 110.4 |
N3—C10—N5 | 119.69 (15) | C20—C19—H19B | 110.4 |
N3—C10—C4 | 122.46 (14) | H19A—C19—H19B | 108.6 |
N5—C10—C4 | 117.85 (14) | C21—C20—C19 | 105.7 (3) |
N3—C11—C12 | 111.50 (14) | C21—C20—H20A | 110.6 |
N3—C11—H11A | 109.3 | C19—C20—H20A | 110.6 |
C12—C11—H11A | 109.3 | C21—C20—H20B | 110.6 |
N3—C11—H11B | 109.3 | C19—C20—H20B | 110.6 |
C12—C11—H11B | 109.3 | H20A—C20—H20B | 108.7 |
H11A—C11—H11B | 108.0 | C20—C21—C22 | 103.9 (3) |
N4—C12—C11 | 113.49 (15) | C20—C21—H21A | 111.0 |
N4—C12—H12A | 108.9 | C22—C21—H21A | 111.0 |
C11—C12—H12A | 108.9 | C20—C21—H21B | 111.0 |
N4—C12—H12B | 108.9 | C22—C21—H21B | 111.0 |
C11—C12—H12B | 108.9 | H21A—C21—H21B | 109.0 |
H12A—C12—H12B | 107.7 | N6—C22—C21 | 102.9 (3) |
N4—C13—C14 | 105.23 (18) | N6—C22—H22A | 111.2 |
N4—C13—H13A | 110.7 | C21—C22—H22A | 111.2 |
C14—C13—H13A | 110.7 | N6—C22—H22B | 111.2 |
N4—C13—H13B | 110.7 | C21—C22—H22B | 111.2 |
C14—C13—H13B | 110.7 | H22A—C22—H22B | 109.1 |
H13A—C13—H13B | 108.8 | C10—N3—C11 | 125.55 (14) |
C15—C14—C13 | 106.06 (19) | C10—N3—H3A | 117.2 |
C15—C14—H14A | 110.5 | C11—N3—H3A | 117.2 |
C13—C14—H14A | 110.5 | C12—N4—C13 | 114.05 (15) |
C15—C14—H14B | 110.5 | C12—N4—C16 | 112.04 (15) |
C13—C14—H14B | 110.5 | C13—N4—C16 | 104.19 (15) |
H14A—C14—H14B | 108.7 | C10—N5—C17 | 127.26 (16) |
C16—C15—C14 | 104.3 (2) | C10—N5—H5A | 116.4 |
C16—C15—H15A | 110.9 | C17—N5—H5A | 116.4 |
C14—C15—H15A | 110.9 | C18—N6—C19 | 114.1 (2) |
C16—C15—H15B | 110.9 | C18—N6—C22 | 113.2 (2) |
C14—C15—H15B | 110.9 | C19—N6—C22 | 105.2 (2) |