Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043467/gg2005sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043467/gg2005Isup2.hkl |
CCDC reference: 627663
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000b); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C16H14N3+·C24H20B− | F(000) = 1200 |
Mr = 567.51 | Dx = 1.20 Mg m−3 |
Monoclinic, P21/c | Melting point: 425 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0635 (2) Å | Cell parameters from 22839 reflections |
b = 16.7776 (1) Å | θ = 1.6–25.4° |
c = 20.8156 (4) Å | µ = 0.07 mm−1 |
β = 97.096 (1)° | T = 273 K |
V = 3141.05 (9) Å3 | Block, yellow |
Z = 4 | 0.50 × 0.35 × 0.25 mm |
Siemens SMART CCD area-detector diffractometer | 5722 independent reflections |
Radiation source: fine-focus sealed tube | 4154 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ω scans | θmax = 25.4°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000a) | h = −10→10 |
Tmin = 0.879, Tmax = 0.983 | k = −20→20 |
16573 measured reflections | l = −21→25 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0481P)2 + 0.729P] where P = (Fo2 + 2Fc2)/3 |
5722 reflections | (Δ/σ)max < 0.001 |
401 parameters | Δρmax = 0.15 e Å−3 |
1 restraint | Δρmin = −0.16 e Å−3 |
Experimental. IR (KBr, cm-1): 3057, 1660, 1589, 1470; UV/Vis (solid; λmax) 406, 620, 804 nm. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.5855 (2) | 0.62758 (12) | 0.01106 (9) | 0.0844 (6) | |
N2 | 0.5948 (2) | 0.70772 (11) | 0.10420 (8) | 0.0632 (5) | |
N3 | 0.45317 (16) | 0.81534 (9) | 0.13029 (7) | 0.0513 (4) | |
C1 | 0.6428 (4) | 0.56506 (17) | −0.01832 (12) | 0.1017 (9) | |
H1 | 0.6002 | 0.5522 | −0.0600 | 0.122* | |
C2 | 0.7581 (3) | 0.51946 (15) | 0.00860 (12) | 0.0932 (8) | |
H2 | 0.7924 | 0.4768 | −0.0140 | 0.112* | |
C3 | 0.8228 (3) | 0.53785 (13) | 0.06992 (11) | 0.0747 (6) | |
H3 | 0.9029 | 0.5084 | 0.0895 | 0.090* | |
C4 | 0.7671 (2) | 0.60033 (12) | 0.10166 (10) | 0.0630 (5) | |
H4 | 0.8074 | 0.6135 | 0.1436 | 0.076* | |
C5 | 0.6503 (2) | 0.64326 (12) | 0.07046 (9) | 0.0579 (5) | |
C6 | 0.4899 (2) | 0.76300 (12) | 0.08464 (8) | 0.0541 (5) | |
C7 | 0.4155 (2) | 0.77065 (13) | 0.02154 (9) | 0.0626 (5) | |
H7 | 0.4388 | 0.7367 | −0.0111 | 0.075* | |
C8 | 0.3096 (2) | 0.82764 (14) | 0.00823 (10) | 0.0668 (6) | |
H8 | 0.2606 | 0.8320 | −0.0336 | 0.080* | |
C9 | 0.2733 (2) | 0.87944 (14) | 0.05572 (10) | 0.0659 (6) | |
H9 | 0.2003 | 0.9181 | 0.0463 | 0.079* | |
C10 | 0.3472 (2) | 0.87219 (13) | 0.11632 (9) | 0.0587 (5) | |
H10 | 0.3248 | 0.9067 | 0.1488 | 0.070* | |
C11 | 0.5258 (2) | 0.81224 (11) | 0.19732 (8) | 0.0487 (4) | |
C12 | 0.4532 (2) | 0.77526 (11) | 0.24313 (9) | 0.0533 (5) | |
H12 | 0.3628 | 0.7497 | 0.2316 | 0.064* | |
C13 | 0.5176 (2) | 0.77678 (12) | 0.30685 (9) | 0.0622 (5) | |
H13 | 0.4697 | 0.7527 | 0.3388 | 0.075* | |
C14 | 0.6524 (3) | 0.81377 (12) | 0.32314 (10) | 0.0651 (6) | |
H14 | 0.6952 | 0.8144 | 0.3661 | 0.078* | |
C15 | 0.7242 (2) | 0.84976 (13) | 0.27660 (10) | 0.0649 (6) | |
H15 | 0.8157 | 0.8742 | 0.2881 | 0.078* | |
C16 | 0.6611 (2) | 0.84983 (12) | 0.21276 (10) | 0.0588 (5) | |
H16 | 0.7085 | 0.8746 | 0.1810 | 0.071* | |
C17 | 0.99158 (19) | 0.18285 (10) | 0.14014 (8) | 0.0443 (4) | |
C18 | 0.9087 (2) | 0.25310 (11) | 0.13963 (10) | 0.0613 (5) | |
H18 | 0.8453 | 0.2600 | 0.1711 | 0.074* | |
C19 | 0.9168 (3) | 0.31281 (14) | 0.09455 (13) | 0.0831 (7) | |
H19 | 0.8598 | 0.3587 | 0.0962 | 0.100* | |
C20 | 1.0080 (3) | 0.30469 (15) | 0.04765 (12) | 0.0844 (8) | |
H20 | 1.0145 | 0.3451 | 0.0176 | 0.101* | |
C21 | 1.0902 (3) | 0.23650 (15) | 0.04518 (10) | 0.0744 (7) | |
H21 | 1.1518 | 0.2302 | 0.0130 | 0.089* | |
C22 | 1.0815 (2) | 0.17664 (12) | 0.09085 (9) | 0.0575 (5) | |
H22 | 1.1379 | 0.1307 | 0.0883 | 0.069* | |
C23 | 0.85558 (19) | 0.04905 (10) | 0.14602 (8) | 0.0442 (4) | |
C24 | 0.9056 (2) | −0.01031 (13) | 0.10741 (9) | 0.0634 (5) | |
H24 | 1.0069 | −0.0210 | 0.1111 | 0.076* | |
C26 | 0.6597 (3) | −0.04038 (16) | 0.05743 (11) | 0.0848 (8) | |
H26 | 0.5952 | −0.0696 | 0.0282 | 0.102* | |
C25 | 0.8097 (3) | −0.05447 (14) | 0.06333 (10) | 0.0825 (7) | |
H25 | 0.8476 | −0.0933 | 0.0380 | 0.099* | |
C27 | 0.6061 (3) | 0.01679 (15) | 0.09470 (11) | 0.0744 (7) | |
H27 | 0.5043 | 0.0263 | 0.0911 | 0.089* | |
C28 | 0.7020 (2) | 0.06082 (12) | 0.13791 (9) | 0.0546 (5) | |
H28 | 0.6624 | 0.0998 | 0.1625 | 0.065* | |
C29 | 0.90892 (19) | 0.13791 (11) | 0.25691 (8) | 0.0472 (4) | |
C30 | 0.9645 (2) | 0.20690 (13) | 0.28954 (10) | 0.0662 (6) | |
H30 | 1.0267 | 0.2404 | 0.2696 | 0.079* | |
C31 | 0.9292 (3) | 0.22670 (19) | 0.35098 (13) | 0.0928 (9) | |
H31 | 0.9685 | 0.2727 | 0.3713 | 0.111* | |
C32 | 0.8378 (3) | 0.1791 (2) | 0.38134 (12) | 0.1045 (12) | |
H32 | 0.8147 | 0.1924 | 0.4223 | 0.125* | |
C33 | 0.7802 (3) | 0.11162 (19) | 0.35108 (11) | 0.0864 (8) | |
H33 | 0.7170 | 0.0791 | 0.3714 | 0.104* | |
C34 | 0.8156 (2) | 0.09122 (14) | 0.28995 (9) | 0.0602 (5) | |
H34 | 0.7756 | 0.0448 | 0.2705 | 0.072* | |
C35 | 1.12672 (18) | 0.06389 (10) | 0.21670 (7) | 0.0395 (4) | |
C36 | 1.26501 (19) | 0.10104 (11) | 0.22200 (9) | 0.0492 (4) | |
H36 | 1.2712 | 0.1519 | 0.2049 | 0.059* | |
C37 | 1.3942 (2) | 0.06560 (13) | 0.25168 (10) | 0.0614 (5) | |
H37 | 1.4841 | 0.0928 | 0.2539 | 0.074* | |
C38 | 1.3897 (2) | −0.00917 (14) | 0.27765 (10) | 0.0660 (6) | |
H38 | 1.4759 | −0.0331 | 0.2977 | 0.079* | |
C39 | 1.2555 (2) | −0.04827 (12) | 0.27364 (10) | 0.0637 (5) | |
H39 | 1.2506 | −0.0990 | 0.2912 | 0.076* | |
C40 | 1.1276 (2) | −0.01242 (11) | 0.24362 (9) | 0.0521 (5) | |
H40 | 1.0385 | −0.0403 | 0.2413 | 0.063* | |
B1 | 0.9704 (2) | 0.10865 (11) | 0.18979 (9) | 0.0400 (4) | |
H5 | 0.634 (2) | 0.7107 (13) | 0.1441 (8) | 0.078 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.1183 (17) | 0.0778 (13) | 0.0523 (11) | −0.0032 (12) | −0.0081 (10) | −0.0153 (10) |
N2 | 0.0762 (12) | 0.0689 (11) | 0.0411 (9) | 0.0044 (9) | −0.0066 (8) | −0.0067 (8) |
N3 | 0.0513 (9) | 0.0585 (10) | 0.0419 (8) | −0.0060 (7) | −0.0034 (7) | 0.0043 (7) |
C1 | 0.165 (3) | 0.0816 (18) | 0.0538 (14) | 0.0005 (19) | −0.0050 (16) | −0.0226 (13) |
C2 | 0.147 (3) | 0.0642 (15) | 0.0685 (16) | 0.0034 (16) | 0.0151 (16) | −0.0127 (13) |
C3 | 0.0959 (17) | 0.0599 (13) | 0.0697 (15) | −0.0020 (12) | 0.0160 (12) | −0.0038 (11) |
C4 | 0.0771 (14) | 0.0594 (13) | 0.0515 (12) | −0.0083 (11) | 0.0046 (10) | −0.0008 (10) |
C5 | 0.0764 (14) | 0.0562 (12) | 0.0415 (10) | −0.0150 (10) | 0.0093 (9) | −0.0043 (9) |
C6 | 0.0584 (12) | 0.0606 (12) | 0.0418 (10) | −0.0134 (10) | 0.0009 (8) | 0.0015 (9) |
C7 | 0.0691 (13) | 0.0746 (14) | 0.0413 (10) | −0.0171 (11) | −0.0051 (9) | 0.0071 (10) |
C8 | 0.0662 (13) | 0.0857 (16) | 0.0446 (11) | −0.0244 (12) | −0.0089 (10) | 0.0189 (11) |
C9 | 0.0559 (12) | 0.0780 (15) | 0.0605 (13) | −0.0060 (11) | −0.0060 (10) | 0.0210 (11) |
C10 | 0.0535 (11) | 0.0663 (13) | 0.0547 (12) | −0.0008 (10) | −0.0001 (9) | 0.0099 (10) |
C11 | 0.0523 (11) | 0.0498 (10) | 0.0412 (10) | 0.0038 (8) | −0.0050 (8) | −0.0013 (8) |
C12 | 0.0581 (11) | 0.0521 (11) | 0.0477 (10) | 0.0030 (9) | −0.0014 (9) | 0.0023 (9) |
C13 | 0.0798 (15) | 0.0574 (12) | 0.0474 (11) | 0.0134 (11) | 0.0003 (10) | 0.0055 (9) |
C14 | 0.0817 (15) | 0.0573 (12) | 0.0494 (12) | 0.0247 (11) | −0.0188 (11) | −0.0056 (10) |
C15 | 0.0582 (12) | 0.0638 (13) | 0.0666 (14) | 0.0063 (10) | −0.0166 (10) | −0.0070 (11) |
C16 | 0.0531 (11) | 0.0629 (13) | 0.0579 (12) | −0.0006 (9) | −0.0035 (9) | −0.0011 (10) |
C17 | 0.0480 (10) | 0.0424 (10) | 0.0390 (9) | −0.0049 (8) | −0.0080 (7) | −0.0031 (7) |
C18 | 0.0680 (13) | 0.0472 (11) | 0.0652 (13) | 0.0009 (10) | −0.0054 (10) | 0.0030 (10) |
C19 | 0.105 (2) | 0.0523 (13) | 0.0844 (18) | 0.0008 (13) | −0.0186 (15) | 0.0147 (12) |
C20 | 0.121 (2) | 0.0600 (15) | 0.0625 (15) | −0.0318 (15) | −0.0287 (15) | 0.0218 (12) |
C21 | 0.0999 (18) | 0.0787 (16) | 0.0421 (11) | −0.0298 (14) | −0.0009 (11) | 0.0048 (11) |
C22 | 0.0750 (13) | 0.0556 (11) | 0.0409 (10) | −0.0111 (10) | 0.0027 (9) | −0.0011 (9) |
C23 | 0.0480 (10) | 0.0475 (10) | 0.0365 (9) | −0.0082 (8) | 0.0028 (7) | 0.0016 (8) |
C24 | 0.0678 (13) | 0.0676 (13) | 0.0551 (12) | −0.0121 (11) | 0.0081 (10) | −0.0187 (10) |
C26 | 0.107 (2) | 0.0850 (18) | 0.0541 (14) | −0.0517 (16) | −0.0244 (13) | 0.0105 (13) |
C25 | 0.119 (2) | 0.0727 (15) | 0.0550 (13) | −0.0295 (15) | 0.0097 (13) | −0.0209 (11) |
C27 | 0.0652 (14) | 0.0817 (16) | 0.0693 (15) | −0.0276 (12) | −0.0197 (11) | 0.0215 (13) |
C28 | 0.0514 (11) | 0.0587 (12) | 0.0505 (11) | −0.0079 (9) | −0.0059 (8) | 0.0096 (9) |
C29 | 0.0418 (9) | 0.0587 (11) | 0.0385 (9) | 0.0151 (8) | −0.0048 (7) | −0.0046 (8) |
C30 | 0.0576 (12) | 0.0786 (15) | 0.0579 (12) | 0.0142 (10) | −0.0117 (9) | −0.0268 (11) |
C31 | 0.0800 (17) | 0.125 (2) | 0.0659 (16) | 0.0426 (17) | −0.0221 (13) | −0.0502 (16) |
C32 | 0.091 (2) | 0.179 (3) | 0.0408 (13) | 0.074 (2) | −0.0058 (13) | −0.0201 (18) |
C33 | 0.0808 (16) | 0.135 (2) | 0.0447 (13) | 0.0460 (16) | 0.0150 (11) | 0.0209 (14) |
C34 | 0.0603 (12) | 0.0777 (14) | 0.0426 (11) | 0.0200 (11) | 0.0066 (9) | 0.0082 (10) |
C35 | 0.0429 (9) | 0.0391 (9) | 0.0370 (9) | 0.0014 (7) | 0.0062 (7) | −0.0035 (7) |
C36 | 0.0435 (10) | 0.0495 (10) | 0.0549 (11) | 0.0009 (8) | 0.0069 (8) | 0.0050 (8) |
C37 | 0.0417 (10) | 0.0702 (14) | 0.0714 (13) | 0.0052 (9) | 0.0030 (9) | 0.0013 (11) |
C38 | 0.0571 (13) | 0.0719 (15) | 0.0668 (13) | 0.0279 (11) | −0.0001 (10) | 0.0018 (11) |
C39 | 0.0765 (15) | 0.0474 (11) | 0.0684 (13) | 0.0193 (10) | 0.0128 (11) | 0.0110 (10) |
C40 | 0.0538 (11) | 0.0439 (10) | 0.0594 (11) | 0.0006 (8) | 0.0097 (9) | 0.0024 (9) |
B1 | 0.0395 (10) | 0.0422 (11) | 0.0373 (10) | −0.0004 (8) | 0.0010 (8) | −0.0033 (8) |
N1—C1 | 1.350 (3) | C20—C21 | 1.369 (4) |
N1—C5 | 1.328 (2) | C20—H20 | 0.9300 |
N2—C5 | 1.415 (3) | C21—C22 | 1.392 (3) |
N2—C6 | 1.354 (3) | C21—H21 | 0.9300 |
N2—H5 | 0.864 (15) | C22—H22 | 0.9300 |
N3—C10 | 1.360 (2) | C23—C24 | 1.390 (3) |
N3—C6 | 1.365 (2) | C23—C28 | 1.396 (2) |
N3—C11 | 1.468 (2) | C23—B1 | 1.637 (2) |
C1—C2 | 1.359 (4) | C24—C25 | 1.396 (3) |
C1—H1 | 0.9300 | C24—H24 | 0.9300 |
C2—C3 | 1.372 (3) | C26—C27 | 1.361 (4) |
C2—H2 | 0.9300 | C26—C25 | 1.370 (4) |
C3—C4 | 1.369 (3) | C26—H26 | 0.9300 |
C3—H3 | 0.9300 | C25—H25 | 0.9300 |
C4—C5 | 1.375 (3) | C27—C28 | 1.385 (3) |
C4—H4 | 0.9300 | C27—H27 | 0.9300 |
C6—C7 | 1.406 (2) | C28—H28 | 0.9300 |
C7—C8 | 1.359 (3) | C29—C34 | 1.395 (3) |
C7—H7 | 0.9300 | C29—C30 | 1.404 (3) |
C8—C9 | 1.386 (3) | C29—B1 | 1.642 (3) |
C8—H8 | 0.9300 | C30—C31 | 1.396 (3) |
C9—C10 | 1.358 (3) | C30—H30 | 0.9300 |
C9—H9 | 0.9300 | C31—C32 | 1.361 (4) |
C10—H10 | 0.9300 | C31—H31 | 0.9300 |
C11—C12 | 1.372 (3) | C32—C33 | 1.368 (4) |
C11—C16 | 1.381 (3) | C32—H32 | 0.9300 |
C12—C13 | 1.382 (3) | C33—C34 | 1.393 (3) |
C12—H12 | 0.9300 | C33—H33 | 0.9300 |
C13—C14 | 1.374 (3) | C34—H34 | 0.9300 |
C13—H13 | 0.9300 | C35—C36 | 1.392 (2) |
C14—C15 | 1.372 (3) | C35—C40 | 1.397 (2) |
C14—H14 | 0.9300 | C35—B1 | 1.640 (2) |
C15—C16 | 1.380 (3) | C36—C37 | 1.388 (2) |
C15—H15 | 0.9300 | C36—H36 | 0.9300 |
C16—H16 | 0.9300 | C37—C38 | 1.369 (3) |
C17—C22 | 1.391 (3) | C37—H37 | 0.9300 |
C17—C18 | 1.397 (3) | C38—C39 | 1.376 (3) |
C17—B1 | 1.644 (3) | C38—H38 | 0.9300 |
C18—C19 | 1.381 (3) | C39—C40 | 1.384 (3) |
C18—H18 | 0.9300 | C39—H39 | 0.9300 |
C19—C20 | 1.362 (4) | C40—H40 | 0.9300 |
C19—H19 | 0.9300 | ||
C5—N1—C1 | 115.2 (2) | C20—C21—C22 | 120.0 (2) |
C6—N2—C5 | 130.80 (17) | C20—C21—H21 | 120.0 |
C6—N2—H5 | 116.2 (15) | C22—C21—H21 | 120.0 |
C5—N2—H5 | 113.0 (15) | C17—C22—C21 | 122.5 (2) |
C10—N3—C6 | 121.95 (16) | C17—C22—H22 | 118.7 |
C10—N3—C11 | 116.76 (15) | C21—C22—H22 | 118.7 |
C6—N3—C11 | 121.29 (15) | C24—C23—C28 | 115.02 (17) |
N1—C1—C2 | 124.7 (2) | C24—C23—B1 | 121.96 (16) |
N1—C1—H1 | 117.6 | C28—C23—B1 | 122.48 (16) |
C2—C1—H1 | 117.6 | C23—C24—C25 | 122.6 (2) |
C1—C2—C3 | 118.4 (2) | C23—C24—H24 | 118.7 |
C1—C2—H2 | 120.8 | C25—C24—H24 | 118.7 |
C3—C2—H2 | 120.8 | C27—C26—C25 | 119.4 (2) |
C4—C3—C2 | 118.7 (2) | C27—C26—H26 | 120.3 |
C4—C3—H3 | 120.6 | C25—C26—H26 | 120.3 |
C2—C3—H3 | 120.6 | C26—C25—C24 | 119.8 (2) |
C3—C4—C5 | 118.8 (2) | C26—C25—H25 | 120.1 |
C3—C4—H4 | 120.6 | C24—C25—H25 | 120.1 |
C5—C4—H4 | 120.6 | C26—C27—C28 | 120.4 (2) |
N1—C5—C4 | 124.2 (2) | C26—C27—H27 | 119.8 |
N1—C5—N2 | 118.0 (2) | C28—C27—H27 | 119.8 |
C4—C5—N2 | 117.76 (17) | C27—C28—C23 | 122.7 (2) |
N2—C6—N3 | 116.99 (16) | C27—C28—H28 | 118.7 |
N2—C6—C7 | 125.52 (19) | C23—C28—H28 | 118.7 |
N3—C6—C7 | 117.48 (19) | C34—C29—C30 | 115.33 (18) |
C8—C7—C6 | 120.0 (2) | C34—C29—B1 | 122.81 (16) |
C8—C7—H7 | 120.0 | C30—C29—B1 | 121.27 (17) |
C6—C7—H7 | 120.0 | C31—C30—C29 | 122.0 (3) |
C7—C8—C9 | 121.32 (19) | C31—C30—H30 | 119.0 |
C7—C8—H8 | 119.3 | C29—C30—H30 | 119.0 |
C9—C8—H8 | 119.3 | C32—C31—C30 | 120.5 (3) |
C10—C9—C8 | 118.2 (2) | C32—C31—H31 | 119.8 |
C10—C9—H9 | 120.9 | C30—C31—H31 | 119.8 |
C8—C9—H9 | 120.9 | C31—C32—C33 | 119.4 (2) |
C9—C10—N3 | 121.0 (2) | C31—C32—H32 | 120.3 |
C9—C10—H10 | 119.5 | C33—C32—H32 | 120.3 |
N3—C10—H10 | 119.5 | C32—C33—C34 | 120.4 (3) |
C12—C11—C16 | 122.22 (17) | C32—C33—H33 | 119.8 |
C12—C11—N3 | 118.62 (16) | C34—C33—H33 | 119.8 |
C16—C11—N3 | 119.09 (16) | C33—C34—C29 | 122.3 (2) |
C11—C12—C13 | 118.49 (19) | C33—C34—H34 | 118.8 |
C11—C12—H12 | 120.8 | C29—C34—H34 | 118.8 |
C13—C12—H12 | 120.8 | C36—C35—C40 | 114.70 (16) |
C14—C13—C12 | 120.1 (2) | C36—C35—B1 | 123.62 (15) |
C14—C13—H13 | 119.9 | C40—C35—B1 | 121.24 (15) |
C12—C13—H13 | 119.9 | C37—C36—C35 | 123.03 (17) |
C15—C14—C13 | 120.60 (18) | C37—C36—H36 | 118.5 |
C15—C14—H14 | 119.7 | C35—C36—H36 | 118.5 |
C13—C14—H14 | 119.7 | C38—C37—C36 | 120.27 (19) |
C14—C15—C16 | 120.3 (2) | C38—C37—H37 | 119.9 |
C14—C15—H15 | 119.9 | C36—C37—H37 | 119.9 |
C16—C15—H15 | 119.9 | C37—C38—C39 | 118.82 (18) |
C15—C16—C11 | 118.3 (2) | C37—C38—H38 | 120.6 |
C15—C16—H16 | 120.9 | C39—C38—H38 | 120.6 |
C11—C16—H16 | 120.9 | C38—C39—C40 | 120.33 (19) |
C22—C17—C18 | 114.90 (17) | C38—C39—H39 | 119.8 |
C22—C17—B1 | 122.11 (16) | C40—C39—H39 | 119.8 |
C18—C17—B1 | 122.63 (16) | C39—C40—C35 | 122.84 (18) |
C19—C18—C17 | 122.9 (2) | C39—C40—H40 | 118.6 |
C19—C18—H18 | 118.5 | C35—C40—H40 | 118.6 |
C17—C18—H18 | 118.5 | C23—B1—C35 | 111.93 (14) |
C20—C19—C18 | 120.2 (2) | C23—B1—C29 | 113.40 (14) |
C20—C19—H19 | 119.9 | C35—B1—C29 | 102.48 (13) |
C18—C19—H19 | 119.9 | C23—B1—C17 | 103.19 (13) |
C19—C20—C21 | 119.4 (2) | C35—B1—C17 | 113.47 (14) |
C19—C20—H20 | 120.3 | C29—B1—C17 | 112.75 (14) |
C21—C20—H20 | 120.3 | ||
C5—N1—C1—C2 | 0.0 (4) | C23—C24—C25—C26 | −0.7 (3) |
N1—C1—C2—C3 | −0.4 (5) | C25—C26—C27—C28 | 0.5 (3) |
C1—C2—C3—C4 | 1.0 (4) | C26—C27—C28—C23 | −0.5 (3) |
C2—C3—C4—C5 | −1.2 (3) | C24—C23—C28—C27 | 0.0 (3) |
C1—N1—C5—C4 | −0.2 (3) | B1—C23—C28—C27 | 171.70 (17) |
C1—N1—C5—N2 | −179.5 (2) | C34—C29—C30—C31 | 0.5 (3) |
C3—C4—C5—N1 | 0.9 (3) | B1—C29—C30—C31 | −170.91 (18) |
C3—C4—C5—N2 | −179.84 (18) | C29—C30—C31—C32 | −0.4 (3) |
C6—N2—C5—N1 | −5.9 (3) | C30—C31—C32—C33 | −0.2 (4) |
C6—N2—C5—C4 | 174.8 (2) | C31—C32—C33—C34 | 0.5 (4) |
C5—N2—C6—N3 | 175.76 (18) | C32—C33—C34—C29 | −0.4 (3) |
C5—N2—C6—C7 | −3.9 (3) | C30—C29—C34—C33 | −0.1 (3) |
C10—N3—C6—N2 | −178.63 (17) | B1—C29—C34—C33 | 171.15 (17) |
C11—N3—C6—N2 | 0.8 (3) | C40—C35—C36—C37 | −0.1 (3) |
C10—N3—C6—C7 | 1.1 (3) | B1—C35—C36—C37 | 172.33 (17) |
C11—N3—C6—C7 | −179.53 (16) | C35—C36—C37—C38 | −0.2 (3) |
N2—C6—C7—C8 | 178.52 (19) | C36—C37—C38—C39 | 0.1 (3) |
N3—C6—C7—C8 | −1.2 (3) | C37—C38—C39—C40 | 0.2 (3) |
C6—C7—C8—C9 | 0.5 (3) | C38—C39—C40—C35 | −0.5 (3) |
C7—C8—C9—C10 | 0.4 (3) | C36—C35—C40—C39 | 0.4 (3) |
C8—C9—C10—N3 | −0.5 (3) | B1—C35—C40—C39 | −172.20 (17) |
C6—N3—C10—C9 | −0.3 (3) | C24—C23—B1—C35 | −33.3 (2) |
C11—N3—C10—C9 | −179.69 (18) | C28—C23—B1—C35 | 155.58 (15) |
C10—N3—C11—C12 | 80.0 (2) | C24—C23—B1—C29 | −148.64 (17) |
C6—N3—C11—C12 | −99.5 (2) | C28—C23—B1—C29 | 40.2 (2) |
C10—N3—C11—C16 | −96.9 (2) | C24—C23—B1—C17 | 89.06 (19) |
C6—N3—C11—C16 | 83.6 (2) | C28—C23—B1—C17 | −82.05 (19) |
C16—C11—C12—C13 | 0.8 (3) | C36—C35—B1—C23 | 142.80 (16) |
N3—C11—C12—C13 | −176.00 (16) | C40—C35—B1—C23 | −45.2 (2) |
C11—C12—C13—C14 | −0.9 (3) | C36—C35—B1—C29 | −95.37 (18) |
C12—C13—C14—C15 | 0.2 (3) | C40—C35—B1—C29 | 76.59 (19) |
C13—C14—C15—C16 | 0.6 (3) | C36—C35—B1—C17 | 26.5 (2) |
C14—C15—C16—C11 | −0.7 (3) | C40—C35—B1—C17 | −161.54 (15) |
C12—C11—C16—C15 | 0.0 (3) | C34—C29—B1—C23 | 30.2 (2) |
N3—C11—C16—C15 | 176.77 (17) | C30—C29—B1—C23 | −159.04 (15) |
C22—C17—C18—C19 | −1.1 (3) | C34—C29—B1—C35 | −90.59 (18) |
B1—C17—C18—C19 | −174.36 (18) | C30—C29—B1—C35 | 80.13 (19) |
C17—C18—C19—C20 | 0.3 (3) | C34—C29—B1—C17 | 147.05 (16) |
C18—C19—C20—C21 | 0.7 (3) | C30—C29—B1—C17 | −42.2 (2) |
C19—C20—C21—C22 | −0.8 (3) | C22—C17—B1—C23 | −76.85 (19) |
C18—C17—C22—C21 | 1.1 (3) | C18—C17—B1—C23 | 95.89 (18) |
B1—C17—C22—C21 | 174.34 (17) | C22—C17—B1—C35 | 44.5 (2) |
C20—C21—C22—C17 | −0.1 (3) | C18—C17—B1—C35 | −142.78 (16) |
C28—C23—C24—C25 | 0.6 (3) | C22—C17—B1—C29 | 160.43 (15) |
B1—C23—C24—C25 | −171.16 (19) | C18—C17—B1—C29 | −26.8 (2) |
C27—C26—C25—C24 | 0.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···Cg7i | 0.93 | 2.78 | 3.408 (3) | 123 |
C8—H8···Cg4ii | 0.93 | 2.81 | 3.506 (2) | 131 |
C12—H12···Cg6 | 0.93 | 2.70 | 3.645 (2) | 167 |
C16—H16···Cg5iii | 0.93 | 2.72 | 3.642 (2) | 153 |
C26—H26···Cg2iv | 0.93 | 2.88 | 3.457 (2) | 120 |
C32—H32···Cg2 | 0.93 | 2.82 | 3.346 (3) | 114 |
C38—H38···Cg3v | 0.93 | 2.90 | 3.532 (2) | 125 |
Symmetry codes: (i) x−1, y, z; (ii) x, −y−1/2, z−1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) −x+1, y−1/2, −z+1/2; (v) −x+2, y−1/2, −z+1/2. |